Founder Wisdom: the full audiobook (7 hours of quotes and stories from 600+ founders and CEOs)

This is Charles, the AI version of me. This is Founder Wisdom, the book, in full. I've interviewed more than 3,000 founders and CEOs on the Founder Wisdom podcast. At peak, it was 15 a day. No prep, no PR team, just a livestream and a stranger who built something. Most of what they said is sitting in YouTube auto-captions that nobody reads, so I had my agents read all of them. This book is the result. The quotes are their words, cleaned up, ums removed, punctuation added, nothing added. The stories are retold short, like a cold open. Every person in here gets a card at the back with their episode and LinkedIn. It's not finished. It grows every week as more episodes get processed. This is volume 1. Read it like a bar conversation. Open anywhere, steal what works, argue with the rest. The Wall. 100 one-liners, no context. Just listen. The best way to raise capital is to not need capital. And by the way, I received hundreds of rejections on our seed. Co-founder and CEO, Mozart Data. I accidentally raised $50 million from one investor for Formula 1 electric racing, and I didn't get a dollar out of the deal. General partner, Sacral Capital. If you want to lose weight quickly without a lot of effort, you can just get a chainsaw and take your leg off at the hip. Founder and director, True North Health Center. It makes no sense to do a startup. You work 3 times as much, you earn a tenth less, you're a lot more stressed. CEO and founder, Exorti. It's going to be absolutely everything, or it's going to be worth nothing. It's too revolutionary to fall in between. COO and co-founder, Dial. We got $24,000 for the book split between the two of us, and then agent fees and taxes. We spent all of our money on therapy. Founder, bestselling author, and book coach, The Finished Thought. There's not a feature in the platform that wasn't asked for by a customer. We don't build things that we think are cool. CEO and co-founder, ImproveOn Health. I actually got booed on stage once for basically telling people that I think we're all going to die. Physician, author, founder, Adamo. It's not that people don't want to come to work. It's that the way they're managed destroys their motivation at the core. Founder and CEO, Demand Metric, Commercial Excellence Consortium. Their punishment is they have to be them the rest of their life. And my reward is I get to be me. Co-founder and CEO, Humanaut Health. We're missing 100% of the people today. CEO and co-founder, Videra Health. The opposite of distraction is not focus. The opposite of distraction is traction. Author and behavioral designer, Hooked: Indistractable. 0.01% of the world has access to that, but 99% of the world has their eyes on it. CEO and co-founder, Current Group. In your career, you will hire someone whose best friend is not human. AI strategy consultant, co-founder, BIG. It's a tragedy that we prescribe so many drugs to people that simply don't work with their biology, and quite honestly, we're too lazy to test for it. Founder, Anto YCF25. After losing all my money 3 times because I was never smart enough to diversify, I decided to write a book. Co-founder, author and speaker, SalesBrain. The first human genome cost $3 billion to sequence. Today we can sequence a genome for $100 in an afternoon. General Partner, Future of Health, Pioneer Fund. Starting with a marketplace is like trying to do a double backflip on an extra-large jump on your first day of snowboarding. Michael Yagudayev, co-founder, CreativeFlow.ai. Out of 3 million accounts reached and 25,000 profile clicks, only 24 people clicked on an actual offer. Daniel Powers Jr., founder, Real Brave. Only in Silicon Valley can you sell your companies for a combined $250 million and feel like you haven't made it. Greg Shove, CEO, section. Our best month ever was January 2020, close to €1 million. 4 months later, we had exactly zero revenue. David Gunnarsson, CEO, Dohop. If we don't get to $2 million by the end of this year, I will sell the company or close it down. It's binary, and I feel nervous and scared for the first time in 10 years. Juan Luis Betancourt, CEO, Humantelligence. There was a period when I thought I was stronger than market cycles. No, gravity finally catches up to all of us. Rich Weidl, CEO, Princeton Mortgage. I fired every single vendor we had, and within 30 days we were profitable. Since then, we've tripled the business. Drew Donaldson, CEO, Grow House. Every time I would pull a trigger, there was a moment of sheer terror. Dear God, please don't let me have missed anything. Kate Van Dam, Head of Strategy, Skyfi. Bankruptcy was actually pretty funny. Now I call it funny. At that time, I was crying under my pillow. Prashant Mahajan, Co-Founder and CTO, Clicker. The person to grow a business from zero to a million is not the same person to grow it to a hundred million, and I'm not that person. John Lee Dumas, Founder and Host, Entrepreneurs on Fire. I graduated engineering with no high school diploma because after one semester they forgot to follow up on my transcripts. Lloyd Lobo, co-founder, Boast.ai. The very good doctor said, we cannot cure. I couldn't quite accept that. I thought, there must be a way to cure. Roy D'Souza, co-founder and CEO, Break BioCorp. When we were selling one thing, it was a glass of water. Then we added tea, coffee, beer, and eventually people see us as a bar. Koen van der Hooijdonk, founder and CEO, connector. In this case, we have to get to the point where we're saying, I'm happy to use it on my own child. CEO, Octus Surgical. I looked at those pouches of breast milk and thought, these are full of antibodies. What if they could become a new medicine for immunodeficient patients? Co-founder, Lactiga. I tell people I'm an alcoholic that opened a bar. I am a significant user of my own services. Founder, MD, Restore Medical Spa. We have a 1,000-year business plan, because a church that withstands the long term has to think generationally about how the finances pass down. Founder, Suivera. I told a VC I had written everything down and would do it for $5 million. They said, do you have an MVP? I said no. Founder and CEO, ex-Special Forces, RamrodXR. I don't care if a million people see my post. I care that one person sees it and spends $1 million with me. CEO, InFocus Brands. China deployed more solar last year than the entire United States did in the last 68 years. CEO, Tandem PV. We got rejected 115 times, and I kept a table that brings you to the ground every time you see it. Founder and CEO, iCover. We are giving these Ferraris to people and ripping out the steering wheel and the seatbelt, then saying drive at full speed. Manu Jagrawal, founder and CIO, Tetranoodle Technologies. The org chart is technical debt. Russell Sean Languedoc, 5x CEO, founder, AI for EBITDA, Outforce.ai. I woke up in the helicopter and grabbed the doctor and asked, was this blood transfusion checked? He said, yeah, don't worry. And I passed out. Ari Gargir, CEO and founder, Red Sea Biotech. Three out of ten words that go to ChatGPT are privileged information right now. Yagub Rahimov, founder and CEO, Polygraph AI. I've been put out of business many times by different governments. The Canadian federal government actually seized ten thousand of our books and burnt them. Ronald M. Bazaar, CEO and co-founder, Tasty Picks International. It's easy to jump on an ideological bandwagon. It's much harder to look in the mirror and ask, where am I violent towards other people? Katya Stepanov, co-founder, The Inheritance Project. Pick a sector where you can fail upwards, where the market is growing around you so fast it mitigates your execution. Niall Murphy, founder and managing partner, Morphosis. I talked with 150 exited founders in the last 2 years, and every single one said, I don't want to raise money anymore. Co-founder and CEO, Klaros Farm. The mayor wanted to make it illegal to do coding, and the first thing I did on city council was legalize software. CEO and founder, Percolata. On my family's farm, we can infiltrate 4 inches of rain in under 5 minutes. Founder and CEO, Continuum Ag. Serial entrepreneurs start stuff and never make any money. Professional entrepreneurs get paid while they're doing it and then have exits. Chief Executive Officer, Prospect Desk. There's actually a mathematical proof that shows that an algorithm cannot debug itself. General Partner, SOSV. The darkness was me attempting suicide 3 times. The darkness was me waking up in hospitals from ODs. High-performance life coach, ultra runner. Chad Weller High Performance Coaching. I kept spending money, and my husband despaired until finally I decided to jack it all in and become a vegan bodybuilder. Kim Constable, founder, The Sculpted Vegan. From sword I jump to the spatula, making dosas, and from the spatula I go into space after 18 years of being at home. Dr. Srimathi Kaysan, founder and CEO, Space Kids India. Humira's patent just expired, and the delta between last year's sales and this year's forecast is $20.5 million a day. Our family living room was more or less like a pharmacy. Everyone exchanged medications for diseases that are preventable. Making games is hard everywhere, but doing games in Africa is Elden Ring. It's the top of the top hardest thing. We created frustration and gave investors a button to solve it. Stefan Nasser, co-founder, OpenVC. I felt like we're just subscribing people to a lifelong prescription. That was not healthcare, that was sick care at its best. Joseph Antoun, chairman and CEO, L-Nutra. My father held my hand and said, Son, I regret so much in life. He died 2 days later with his dreams intact, and I'm not going out with regrets. Deryab John Llewellyn Davies, founder, The end of the world can only be a one-time event. It's either the end of the world or it's not. Founder and CEO, CFP, Endurance Wealth Partners. No one's ever like, Wow, you confused me so much, I'm cutting you a check. Co-founder, early-stage VC investor, Razy, Deco, Evolution VC Partners. Get close to dying and not die. I have not met a founder who either didn't go bankrupt or almost died in the process. Even in the operating room, the surgeon said I might lose both legs, and my question was, okay, but where can I go back racing? There are 525,600 minutes in a year. How many do you spend in front of a doctor? 200, at most. When pay becomes what people bring up, it means you failed on all the other areas you promised when you hired them. Principal, author of Toxicity, Clear Day Strategies. I didn't find Saddam. These prisoners took me over 5 months. 300 prisoners. I didn't know where Saddam was. Speaker, author, former Army interrogator, Ermatics. Never trade something anyone can do for something only you can do. I had a state trooper following me around 24/7 and protecting me from assassination attempts for 6 months. I want to produce gasoline for $2 a gallon and sell it for $2.20, take a 10% margin, and make trillions of gallons. Being willing and being able are two different things. If you can recognize it in someone else, you're able to do it. Whether you're willing is whether it happens. Chris J. Snook, founder and managing partner, Atomic Capital Virtual Family Office. I'll just delete a software and see if anybody says anything. Typically they don't. David Riggs, founder, Numa Media. Those therapies are sold at one-tenth of the US price. Half a million dollars in the US, $30,000 in India. Founder, East Ocean Bio. Billions without peace? You're the poorest man in the world. Founder and CEO, Warrior Sage and Accelerated Evolution Academy. AI will replace all how-to content. What it cannot replace is the emotional experience of being alive. Executive coach and writer, Good Work, former COO of ConvertKit. Being in a band is the best sales training you could ever have. Founder and CSO, The Sales Rebellion. If I had known what I was getting into, I arguably would have never started the business. Sometimes it's good to be a bit naive. Chairman of the Board, Brevo, formerly Sendinblue. Productivity is producing more, efficiency is producing more with less, but being effective is producing the right thing. Founder and business coach, Less Doing. I never applied for a job. I always wanted my own business, even though polio gave me an easy route to a reserved one. —Rishabh Bitola, founder, Infotyke. If your skill can be replaced by typing a sentence into a chatbot, you didn't have a skill to begin with. —Chris M. Walker, CEO, Leggett. Squatting is about courage, bench is about focus, and deadlift is about aggression, the part of your brain that could lift a car off a baby. General partner, Outset Ventures. The first business I tried on my own felt like watching paint dry, except I was the paint. CEO and founder, Focusmate. The product I sold for $61 million, I'd offered to sell one week after developing it for $360,000, and they turned me down. Founder, TruVideo. The ultimate skill of the human being is the ability to get loud in your head with the right words at the right moment. Founder, ex-SWAT sniper team leader. Shot IQ? Mind IQ? The answer is nobody knows, because nobody writes biographies of those guys. Probably 99 out of 100 never make it. Founding publisher, Skeptic Magazine. Every good founder is delusionally optimistic. They're not reasonable people. Founder and partner, FF Venture Capital. A truck driver in Mozambique will not buy a smartphone to play Angry Birds, but he will buy one if he can get more loads. General Partner, Reflect Ventures. If you solve for a million, you make a lot of money. If you solve for a billion, you change history. Serial Disruptor, Author, Keynote Speaker, jsomit.com. My business partner said, let's buy this thing back from them for a dollar. I said, you're crazy. We owe $2.2 million. CEO, Jetstream. I didn't have an identity crisis selling the business, because I already had one back in my late 20s. Derek Wilder, CEO, Hallmark Homes. I'm living fully knowing that I was always dying. From the moment you're born, the aging process begins. Author, coach, CEO, Academy for Coaching Excellence. Mosquitoes are super easy to kill. They're not hard to kill. You just don't know where they are. CEO, BZigo. I own a stair and railing company, one of the largest, but I have never, ever installed a railing before in my life. Kevin Halliday, podcast host, president, Shed Talk, Spindle Stairs and Railings. My job is to have the cell phone numbers of the top 500 CEOs and chairmen in Quebec. Roger T. Douguin, managing partner, practice leader, CEO and board services, Boyden. Instead of one treatment a year and then dying after 10 years, what if we could try 50 or 100 treatments before it's too late? James Hammett, Most people go from animals to humans. I'm going from humans to animals. CEO, Dog Years. Anyone can sell a dollar for 50 cents, but you just can't do it for long. CEO, Nine Zero. The mark of a great surgeon is knowing when not to operate. Founder, orthopedic surgeon, Victory in Motion. The man that shaped my life as an entrepreneur was willing to give up everything that he ever worked for just to extend his life. Charles Gaudet, CEO, Predictable Profits. Innovation is rewarded, but execution is worshipped. Ari Goldberg, founder and managing partner, RNMKR. Money doesn't solve all problems. Money solves money problems. Bala Kamalakaran, founder and managing director, Startup Iceland, Iceland Venture Studio. Chapter one: Where it started. Nobody starts with a plan; they start with a wound, a boring job, or a problem that wouldn't leave them alone. I woke up on Monday morning and put on a really nice suit and went down to the office and sat in one of the cubicles. I didn't even have a password. I pretended like I worked there. I lasted about twenty minutes until I was called into the CEO's office. He said, "What are you doing?" I looked right back at him and said. What are you doing? I'm making money. And I got the job. David Shadpour, founder and CEO, Social Native. 3 Failed Insurance Experts and 1 Big Excel Spreadsheet. Craig Carroll is a contractor at a property software company when the CEO hands him a problem. The CEO believes his clients have fewer insurance claims, so carriers should give them a discount. 3 insurance experts have already failed. Carroll asks for a year, interviews everyone in the chain, then returns with good news and bad. The idea won't work, because actuaries want 20 years of data. The better idea is a managing general agent. One night at a bar, with a giant spreadsheet, they score every task in the software against every type of claim. A roof inspection is a 6. A fire suppression test is a 26. 2 years later, the score predicts who will have claims. Carriers hand over the pen and pay about 14 cents on every premium dollar. Carol calls it an amazing business, very difficult. He builds it through a brutal divorce. That story is from: You could be on a crappy journey on the way to hell, but great companions make it memorable. Here I am on this refugee bus, and I'm like, this is my tribe. When we lived in the refugee camps, it was some of the best times of my life. Co-founder and author, Boast: AI and Traction. He injected himself on a livestream. Then a dog got better. Tristan Roberts is recruited by biohackers building a gene therapy for HIV. He knows that even if it works, nobody will believe him, so he livestreams his own injection. Netflix later covers it. The HIV therapy does not work, and the company collapses. But a spinoff, Mini-Circle, tests a follistatin plasmid gene therapy on 44 people on the island of Roatán in Honduras because a human study there is faster and cheaper than in the United States. 2 participants with rheumatoid arthritis lose their pain for months. Nobody promised them that. Roberts asks if he can give it to his family's dog, who is crying most nights and refusing walks. The dog recovers for about a year. That got me thinking, he says, and Dog Years begins. That story is from... I bought a book about how to roof your house. I read the book, put an ad in the Yellow Pages, which was the Google of my day, And my wife at the time was horrified that I was spending $800 a month on an ad for my new business while unemployed. Philip Ogilvie, founder and chairman, Stack Construction Technologies. A pop punk kid who could not afford a studio. Anshu Dwipashi is at Duke studying computer science and playing in a pop punk band, and he wants to record music. He cannot afford a studio and has no audio engineering skills, so he remotely enrolls at Berkeley College of Music to teach himself. Years later, after a stint in robotics at Amazon and a failed first startup, he builds Graysound, an AI production studio that does the engineering so musicians can focus on the art. At 13, he had wanted to build what is now Perplexity. At 16, he shipped a news app. He was pretty sure any day now he would be a billionaire. Today, Graysound is free, has about 190 users, and he is raising money. That story is from. When he told me he wanted to start this business, I said absolutely not. We need to buckle down and do one thing at a time, and he ignored me. When I went to bed, he built a website. Lena Phoenix, co-founder, Zero Shoes. A zero percent homework kid and a white BMW. Nick Hutchison is an athlete, not a student. In AP Calculus, he is famous for having a zero percent homework average. Capable but bored. Then, before senior year of college, he takes a sales internship at a software company. His boss, Kyle, drives a new white BMW, makes good money, and likes to party. Nick decides he wants to be like Kyle. If Kyle listens to podcasts, so will he. Podcast after podcast, successful people credit books. Nick realizes that not reading means forfeiting a better future. He puts his ego aside, walks into Barnes& Noble, and grabs a stack of 10 books. He starts posting what he reads, his following grows, and authors begin asking him to promote their work. Today, that hobby is BookThinkers, a 15-person marketing company serving hundreds of authors a year. That story is from— During COVID, I lost my job, and my wife said, either you start your own agency or you find something else to do. I didn't know what else to do. I got into advertising because I suck at everything else. Justin Oberman, founder, Oberman& Partners. From Railheads in Iraq to a Rail-Riding Truck. As a teenage Army recruit, Kevin DeMoa serves 2 tours in Iraq, moving tanks and Bradleys from road to rail. He sees how many touches it takes— cranes, forklifts, drayage trucks, an army of people for one container. Later, he joins SpaceX, where he builds the organization that ships rockets from site to site, becoming, he says, the first person in the world to commercially launch, ship, and eventually recover a rocket. Then come Northrop Grumman, electric truck startups, and Harley-Davidson's e-bike spinoff. Through all of it, the road-to-rail problem nags him. So he founds Glid, building an autonomous vehicle that drives onto railroad tracks carrying a container, and a certified box on wheels that does the same with a driver aboard. His pitch: Don't ship it, just glide it. That story is from: When I moved to the U.S., nobody cared. We'd sold MessageLabs for $700 million, and nobody had really heard about the company. I thought it would give me a lot of access. It was a rude awakening. I was back to zero. Duncan Logan, CEO, Nine Zero. $10,000 and a movie trailer obsession. Sahin Boydas leaves Turkey for Silicon Valley with about $10,000, enough to rent a place in San Francisco for a few months, A self-described movie trailer nerd, he builds a social network around upcoming films. It is acquired by Gfycat, which Snapchat then acquires. He builds again, a sticker marketplace that tops Apple's iMessage store for months, and then a remote work company incorporated in October 2019. COVID hits 4 months later, and it grows to hundreds of thousands of companies. 2 of my angel investors were angel investors in Gusto, and they were using his product. They introduce him to Gusto's founder. It is love at first sight, and Gusto acquires him. He stays 4 years, his first real job. Now he angel invests, with over 150 deals, 26 of them unicorns, and builds Claro's Farm. That story is from— I was bringing my textbooks into work, reading 15 seconds in between building these cars, and I did that for 5 years. Joe Chura, founder and CEO, GoBrewing. 3 brushes with death before she turned 33. Sharmin Ali is 10 when she watches a deadly flood hit her home region of India. At 11, a 7.2 earthquake collapses her building, and her family lives in a rehabilitation camp for 3 months. At 12, she witnesses a genocide between 2 ethnic communities, hers one of them, and spends years with insomnia. Decades of therapy follow, plus a clinical depression diagnosis. Then, at 33, stress puts her through a cardiac arrest. The doctor can't believe it. Her reply: How minor. She turns the pattern into an edge. When you have seen death that closely, pressure feels survivable, and she says she does not crack under it. She later helps start SAFE, a mental health resource for entrepreneurs, so no other founder walks that road alone. That story is from: Who we are today is the sum of who we've been in our lives. Some of those parts may seem outrageous, and we want to keep them private, but you would not be who you are today without all of those parts. Tom Lenoble, author, coach, CEO, Academy for Coaching Excellence. A student spam rejection that became $100 MARR. Stefan Skibesta is a university student in Berlin who needs a business plan for his entrepreneurship class. He and a high school friend already run a small web agency, and they have built a clunky desktop app for one customer to send newsletters. They pitch turning it into software online. The university funding office takes one look and says, you're sending spam, right? No funding. Everyone tells them email marketing is dead, that Facebook will kill it. They launch in 2011 with €50,000, stay naive, and focus on Germany. By 2018, they have around 80 employees, hit a ceiling against Mailchimp, and sell to Sendinblue. Stefan stays, moves to Toronto, and helps push the combined company, now Brevo, past $100 million in ARR. That story is from one of the clients called me up on a Sunday night, really late, complaining about his business. He was getting a crazy amount of calls. He was buried before I met him. I was like, we're done. I fired him on the spot and shut down the agency. CEO, Website Rental Coaching. The physicist who wants to make gasoline from air. Casey Hanmer has a Caltech astrophysics PhD, a stint at a Hyperloop startup, and 4 years at NASA. Then, in 2021, he decides the future should not include worrying about gas prices, and nobody else seems to be building it. So he starts Terraform Industries. The pitch: use cheap solar to pull CO2 and water out of the air and drive combustion backwards into methane and methanol. Today, he has nearly 30 people and a desert test site with 1.8 megawatts of solar. His prototype produces methane about 10 times cleaner than pipeline natural gas. His business model, he says, is Costco, no frills. His website looks like the early internet on purpose. The goal is gasoline at $2 a gallon, and by 2029, he believes, it will become obvious that it works at scale. That story is from— I grew up in the Paquanok Projects in Bridgeport, Connecticut, in the 1980s, and it was real difficult. I had a father who was in prison most of my life, uncles and cousins in and out of prison due to drugs, and I was lucky to make it out with the help of a lot of supportive people. Luke Cooper, founding partner, managing director, Latimer Ventures. A 25-person email list became 7,000 attendees. In 2018, Eric Yang gets a client with a problem. The client's Airbnb webinar funnel has flopped, and his email list holds exactly 25 people. Eric proposes something different: an online summit interviewing 15 people crushing it in short-term rentals. He lands the biggest speakers in the space and pitches sponsors, companies who sell locks, alarms, and property software to Airbnb hosts. They pay to reach those owners. Half the attendees arrive through ads that sponsors fund. 3 months later, the guy has 7,000 attendees, and we raised $25,000 in sponsorship. Eric's own first summit worked the same way. He cold emailed Jordan Harbinger, got a yes, and used that name to land every other speaker. He spent nothing on ads. That story is from: I traveled to SF multiple times and nobody would take me because I didn't know SQL. I had never heard of SQL before. I started picking it up on my own, reached out to many companies, and eventually one company gave me a chance. Alan Zhao, co-founder, Warmly. A paragliding crash and a stranger's blood started a company. In 1989, Ari Gargir is a self-described terrible pilot paragliding when he slams chest-first into a big rock. No broken bones, but his lungs blow up. He wakes in a helicopter, receiving a blood transfusion for the lung injury. These are the early days of HIV, and he is terrified. He grabs the doctor and asks if the blood was checked. Yeah, yeah, don't worry, the doctor says, and Ari passes out. The transfusion saves his life and plants a fixation on blood supply. Years later, after bringing dozens of products to market, he meets a technology that grows stem cells at mass scale and turns them into red blood cells. Suddenly he has his eureka: blood without donors, one universal type, made in a clean, controlled environment. That idea becomes Red Sea Biotech. That story is from I was never special enough to make an impact on a professional basketball team, let alone go to the EuroLeague or NBA. It was an ah moment when I realized that at this level I was just not the best, and I could never be. Idris Al Rifai, co-founder and CEO, Flow48. A brother's overdose became a medication safety company. In 2019, Justin Amoyal is a program manager on Navy research programs when he gets the worst news of his life. His brother has overdosed. He takes about 6 months off, unable to work. Then he does what an engineer does. He investigates. His brother lived in an extended care home, and Justin digs into how medications are managed there. The answer is quiet and damning. It wasn't anyone's fault, besides the fact that the tools didn't exist: paper records. Staff on minimum wage after a 4- to 6-hour course, he founds Improve On Health. A National Science Foundation grant forces him into customer discovery, and he meets parents of people with intellectual disabilities who ask for the product before it exists. Today the locked smart med box and app serve providers in about 26 states. That story is from My Wife Died of It. On the first day of treatment at MSK, the very good doctor said, we cannot cure. I was surprised. I said, let's give it a try. Inject the drug, see what happens. But they knew right away they can't cure. I couldn't quite accept that. Co-founder and CEO, Break BioCorp. A laid-off anchor spent $10,000 learning to fly. Andrew Schmertz is a TV business anchor and reporter when he loses his job at New York 1. He has time and he has a credit card, so he spends $10,000 on a pilot's license. Flying is his hobby, and then he made the mistake of turning a hobby into a business. He gets investors, builds a team, and certifies an airline from the ground up around 2010. The paperwork is brutal. The FAA gives you a tremendous amount of homework, and Andrew's approval takes about 15 months, which he says was lucky. It can take five years, all while you sit on expensive aircraft that aren't flying and you're not making revenue. Today, Hopscotch Air flies small four-seater planes about 150 miles from New York to Nantucket for a third less than traditional jets. That story is from Nobody cares about the cool thing you did; they want to know the cool thing you learned. The story gets them in the seats, but they need to know how it applies to their life today. Eric Maddox, speaker, author. Former Army interrogator, Hermatics. The week after the hospital, a teenager was alone. Loren Larson points to one patient who haunts the problem his company exists to solve. A 1-7-year-old goes into the hospital, is put on medication, and is stabilized. He goes home and sees his primary care doctor about something else. The doctor says, you shouldn't be taking that, so he stops. A week later, he is home alone, his parents out, depressed again, and now it feels worse because he believes he failed at treatment. Then a message arrives from Vedera: Hey, tell us what's going on. He answers on video, honestly, and the system detects it. Lorenz's point is simple: There are people alone and isolated, sitting by themselves trying to figure out what to do next, and no one has ever had enough people to check in on them. That story is from I Grew Up Poor. I worked really hard to get to Wall Street, got the CFA, was making 6 figures in my 22nds. But every day I was on the 6 train touching one-one strangers, wondering, is this it? Is this my life now? Brian Bell, founder and managing partner, Team Ignite Ventures. After every product failed, he bought a business. Matthew Tse is a developer for startups, big tech, and finance when he gets the itch to be a founder. He launches products. They all failed. The problem, he realizes, is that he is miserable at getting customers at all. So he flips the plan and goes shopping for a business that already has a distribution engine. He tries buying SaaS companies but gets outbid by people offering full cash. Then he finds ImprovMX, an email forwarding service run by 2 founders for 10 years, now focused on a new product. He pays what he calls a healthy SaaS multiple for a 6-figure revenue business. It is cash positive from day one. He keeps both support staff, turns one into a junior dev, and the growth never stops. That story is from: I did not know that investors existed. The only thing I knew was you could do outsourced services, take that money, and use it to build products. Arjun Pillai, co-founder and CEO, Docket. A $70 setup that became a meat chip company. Michael Blumenkrantz works in finance, eats clean, and wants a kosher meat chip. The problem is he has just had his first kid and cannot cook. A buddy comes over with dinner, complaining about his job. Mike tells him it is something he has always wanted to make. The friend goes home, buys a $20 slicer and a $50 dehydrator on Amazon, and slices a piece of meat. 2 days later, he calls. Mike tries a couple of bites. No preservatives, no sugar, just meat and salt. They give it a name and start cooking. The first day, putting it on his WhatsApp status, they sell $2,000 worth. Now Primal Crisp is bootstrapped and growing 50% month over month, still limited only by oven space and a 10-hour cook time. That story is from every single student from Waterloo ends up by the time they're graduating working between four to six full-time jobs in the industry. You walk out with a year and a half to two years of practical work experience versus everyone else having zero. Cole Dermott, co-founder, Locus YCF25. A metal screamer sells $5 CDs to strangers. At 17, Dale Dupree is on his first tour with a metal band, and nobody in the room knows his name. He has about 10 minutes of a set to earn credibility, or people walk out. Between sets, he fills his backpack with burned CDs and works the crowd. Hey, what's up? I'm Dale. I'm one of the guys playing tonight. He pops a disc into a portable player, lets strangers listen, and sells the EPs for $5 each. That is his hustle story, while other people sell comic books in high school. Years later, with no college degree, he walks into copier sales and finds that the stage taught him the lessons that matter: trust, perception, and sales as an art. He eventually builds the Sales Rebellion. That story is from— I had mentors who sat me down and said, this is a mistake. You need to do conventional biological research. You won't be able to make a living because no one will hire you. And I'm glad I didn't listen to them. Dave Messina, General Partner, Future of Health, Pioneer Fund. The man whose 10,000 books were seized and burned. Ron Bazar is the first person to bring ginseng to North America in the mid-1970s, back when nobody had heard of it. He publishes a book about it, 10,000 copies of Ginseng: The Root of Life. Then the Canadian government shows up and seizes the whole print run. Ron says it looks like a SWAT team— yellow tape around his house, boxes carried out of his basement into a van. It's like a crime scene. The books are burnt. He cannot afford lawyers, and a few years later U.S. food and drug authorities ban importation of the product, killing that business too. Ron is not bitter now. The stories are painful when they happen, he says, but he laughs at them today. That story is from When I was 13, I had this ridiculous dream. I wanted to walk into a Starbucks and see at least 3 people using a product that I built, without them knowing I built it. That's the life goal, to continue to get to that state. Founder, Deep Prediction. The 2-5-year-old who ran Overstock under armed guard. Jeff Atkinson is 25 and skiing his way toward New Zealand when his mother books him a job interview at Overstock. He meets founder Patrick Byrne and decides on the spot, he's my ticket. Within years, Jeff runs revenue for the whole company, over a billion dollars of it, and grows SEO from zero to a $300 million channel in 3 years. Then Byrne sues Wall Street over short selling. Suddenly, a black car trails Jeff to work every day. The state assigns him a trooper for 6 months. Byrne gets a sniper on his roof. The pressure builds, and Jeff reaches for alcohol and other substances to calm his nerves. He leaves to get help, is promised his job back, and the board votes no. Byrne never funds his startup either. For the first time on air, Jeff says it plainly: his Overstock career ended over addiction. That story is from I Changed Hello World So It Printed in Orange Instead of Black. The moment that text turned orange, a light bulb went off in my head. I thought, "Wow! I can make this computer do anything I ever wanted." Jeff Sabert, CEO, Digits. A boy crosses the Berlin border to see his mother. In The 1,970 Seconds, Yatsiu is a kid whose single mother, a musician, works at the Komische Oper in East Berlin. So he takes the train and crosses the border to visit her. What he finds on the other side is not chaos, he says, but starkness, a world of information control. In the supermarket, there's a banana and an apple one meter apart. And another banana. Maybe a pear. Too much space, not enough food. It is the opposite of abundance. Later, he lands at Atari in America, which he calls capitalism on overdrive, and then in Hong Kong, where there is no social safety net at all. 3 systems, 3 extremes. Each one, he says, told him that is not right either. That story is from. I had a budget for the year of £900. I don't think I paid for one night of accommodation in a year. I hitchhiked most places. I slept in jungles, in cabs, on trains, and I also got invited to stay with the first prime minister of Malaysia. Simon Kelton, writer, adventurer, investor, founder, Inspirational Adventures. He bet his intern savings on humanoids and kept $900. Jasmeet Singh finishes his master's in computer science in India. And works as a remote intern for a U.S. company. The pay is in dollars, he lives with his parents, and he saves almost everything. Then he makes 2 bets on humanoid robots: a Swiss university research group that is not yet a company, and a man building humanoids in his garage in Florida. When the money settles, he is left with closer to $900. Job offers are waiting, a PhD plan has fallen through, he decides to be super careful with every dollar and uses the $900 to start his own robotics company. The first of several. Both humanoid bets, he notes, took about ten years to look like companies. That story is from. I'm a professor, and I know what I need to do for tenure, and it doesn't include writing NumPy. But I also see that the world needs somebody to write NumPy, and I'm one of a handful of people who could do it—not for unique skills, but for the connections, the awareness, the time, and the naïveté. Travis Oliphant. CEO, founder, head of OSS, Platform, Quansight, Zyphra. The Sleepless Teenager Who Set Out to Rebuild Healthcare. From age 8 to 18, Max Marchioni is sick and nobody knows why. Chronic migraines. Chronic sinusitis. It takes 3 hours to fall asleep every night, and he dozes through a third of his high school classes. I didn't know what was wrong with me. So he becomes a health geek. In 2016, he wears an early Oura ring while classmates mock him for tracking sleep. Blue light glasses, glucose monitors, mouth tape. People think he is strange. In 2017, he makes his first investment in a longevity company. Years later, he quits Goldman Sachs and asks what he wants to spend the next 50 years on. It has to be personal, matter for humanity, and be a $100 billion company. A new city? Or a new healthcare system? He picks healthcare first and starts Superpower. That story is from My Buddy and I Started a T-Shirt Company. We Sold Really Offensive, Degrading T-Shirts. We Would Have Been Cancelled in This Era. But That Terrible Business Led Me to My Own Massive Life Breakdown and Breakthrough. Bradley T. Morris, founder, Magic Media, Magic Kids, Chi Ball. The 7-Year-Old Who Slept on Park Benches. A 7-year-old boy is sleeping on park benches in the city at night. Police pick him up every couple of days as he keeps running away. He is not allowed in school. When he arrives at Cheryl O'Donnell's youth club, it takes about a dozen staff chasing him to catch him when he bolts. In her office she keeps little Buddhas. She tells him that when he is feeling uptight, he can come in here and rub the Buddha's head and close your eyes and take 10 deep breaths and think of something he loves. He calms himself down. Months later, he is back at home and back in school, and one of her workers sits in the classroom with him until he is comfortable enough for the worker to step away. That story is from— In 1983, my professor said, we're never going to be able to understand how the brain works. For a 2-1-year-old, I thought, I'm going to prove her wrong. So I spent the next 20 years trying to do that. John Ball, cognitive scientist, author, and CEO, Pat Incorporated. A catering side dish became a frozen food company. Margarita Womack, a Colombian-born PhD, starts a catering company to give a friend a job as chef. Empanadas turn out to be the best seller, and the real business is frozen foods. She has never worked in food. Her first production line is built with popsicle sticks and duct tape, and the room is always too hot or too cold. She quits her teaching job anyway. Her roots run deeper. 25 years earlier, a guerrilla extortion threat forced her family to send her abroad, And she arrived barely speaking English. You realize that you're so much more adaptable than you think you are. 7 years on, Maspanadas has a purpose-built plant and about 3,200 stores, including Whole Foods and Sprouts. That story is from— Making games is hard everywhere. There are 30,000 games every year, so to be remarkable, you have to be exceptional first. But doing games in Africa is Elden Ring. It's the top of the top hardest thing. Olivier Madiba, founder, Kiro'o Games. Facebook for Latin America, sold to a dating company. Thomas O'Farrell finishes university in Argentina just as everything goes to hell. A friend pitches an internet company, and they say, why not? It's 2002, the bubble has just burst, and nobody is investing. We were bootstrapped before the term existed. They sell prepaid phone cards online, learn to run a funnel, Then builds Sonico, a social network that becomes Facebook for Latin America before Facebook is big. Investors pile in during the Web2 frenzy, and the team raises far more than it needs. Culture changes. They chase user acquisition and neglect retention. Sonico finally sells to a match and dating company, an exit that falls well short of expectations. Tomás carries 2 lessons into Workana: build for the people who would show up with pitchforks, And never raise more than you need. That story is from: I didn't have any capital, so I went and begged my family to give me some money, and they did. I took all that money and went all in. It was about $300,000. Bala Kamalakaran, founder and managing director, Startup Iceland, Iceland Venture Studio. The hacked marketplace that became a business. In 2013, Chris Walker has a day job in customer support and a side hustle in SEO. He takes client calls in the bathroom so he will not get fired. An influencer endorses his freelance services on a Fiverr-like marketplace, and he finally quits his job. Then the marketplace gets hacked and becomes unreliable. Chris moves sales to his own website and drives his customers into a Facebook group. The other freelancers there ask if they can use his site too. The light bulb went off. He partners with a customer who once bought a $16 service And they launch Legiit as a simple marketplace. Within the first month, it becomes his biggest revenue stream. Almost 8 years later, it consumes his whole life. That story is from: I found the deal when I was 17, sitting in detention in high school. I wasn't an inventor, but I thought I might be good at raising money. I asked the founder for a little allocation and raised just under a million dollars. Co-founder, Early-stage VC investor, Razy, Deco, Evolution VC partners. He quit for a six-figure job and came back to a bigger company. Robert Indries meets Alex Berman in a Facebook group for founders. Alex needs marketing help. Robert raises his hand, and the tasks keep coming until he is delivering for every client at Alex's cold email agency, X27. Alex hands him 30% of the company. I didn't ask for it. Then Alex gets a 6-figure offer to be chief marketing officer elsewhere. Robert tells him to take it, since Delivery will keep running, the other company doesn't work out. 6 months to a year later, Alex returns to find X27 2 or 3 times larger. He makes Robert CEO and raises his stake from 30% to 50%. They have been equal partners ever since, and went on to co-write a bestseller, The Cold Email Manifesto. That story is from. I literally came out of doing a PhD in applied mathematics, complex variable analysis applied to fluid dynamics, and went to sell hotel discounts for manicures at Groupon. It was quite a change, but they had an incredible amount of hustle. Ofer Samson, founder and CEO, Ezra AI Labs. She went from making doses to launching satellites. Srimathi Kesan grows up in Hyderabad as a national basketball player. A state athlete, a paratrooper, and a parade commander in the National Cadet Corps. Her conservative parents worry only about one thing: Who will get married to you if you break your bones? At 18, she is given direct entry into the armed forces. The same week, she has to move to another city, because she is getting married. She spends the next 18 years at home. Then a friend takes her to a conference, where she meets the directors of Kennedy Space Center. She brings 3,500 Indian children to NASA. Starting in 2015, she launches balloons, then suborbital payloads, then orbital satellites. She calls her life 3 words: sword, spatula, space. That story is From. About 13 years ago, I published my first book, and then I realized the publishing process is completely broken. So I opened my own publishing house. I wasn't that clever about the name. I named it Kniv Publishing. It was completely bootstrapped, and it grew to become the largest publishing house in Israel. Yehuda Kniv, founder and CEO, Spines. A banker quits to walk every government hospital in South Africa. Saul Kornick leaves a London investment bank because, as he puts it, it didn't feed my soul. He does not want to make Hank Paulson richer. Back in South Africa, he starts a company to reverse the brain drain and bring qualified clinicians home. To do it, he visits every government hospital in the country. What he finds shocks him. Patients bring blankets to queue overnight to see a doctor, and people are treated for diabetes with the wrong medication because the right one is not available. Only 9 million of South Africa's 60 million people can afford private care. So he asks how he would rebuild care from scratch, with nurses first, technology doing the heavy lifting, and doctors only when needed. The result cuts the cost of care by 75%. That story is from: Elon said, I need these rocket engines to look better. I said, You can't do that with things you've already engineered and tooled up unless you start over. He said, Okay, fine. You're in charge of our newest rocket engine. —John Bucknell, CEO, Virtus Solis Technologies. From Haul Truck Driver to Gong-Wielding Event Promoter. Mike Reid is driving giant haul trucks in a mine in northern Canada, Working 12-hour days and nights, moving earth for money he does not care about. He has just gone through a breakup. On his days off, he escapes into alcohol. All of that sort of brought me to my knees, and that's where I got the gift of desperation. He starts with yoga, then breathwork, float tanks, and supplements, and eventually discovers sound healing. A lifelong musician, he buys gongs and singing bowls and gives free sessions in exchange for feedback. Then the light bulb. Sound works on a whole room at once. He partners with yoga studios, splits 25% of revenue, and repeats the event across the region. Today, he makes 5 figures a month and teaches others to do the same. That story is from— It struck me on a flight to San Francisco, in conversation with my neighbor, that I wanted to switch sides. After almost 10 years as a venture capital investor, I decided to disrupt my own industry with a data-driven solution. Penny Schiffer, CEO and co-founder, Raise.ai. Born 4 days after the Soviet Union fell. Katya Stepanov is born in Minsk on the 4th of August, 1991, 4 days after the USSR collapses. Her mother remembers watching the TV go blue and Swan Lake begin playing, the signal that something was happening in the government. Belarus has no paperwork of its own yet. Her young parents, still in their 20s, flee as Jewish refugees and land in New Jersey in 1992, Speaking no English and knowing no one. With no money for toys, they hand her a camcorder, and she watches herself on the TV screen in costumes and characters. She learns English through Disney movies and becomes the family's interpreter of culture. I was born into a very confused place. That confusion becomes her career— an actress trained at Carnegie Mellon who now teaches leaders how to resolve conflict. That story is from... I am a French nerd who migrated to the US about 35 years ago. I sold multimillion-dollar supercomputers, and after doing a few startups and losing all my money three times because I was never smart enough to diversify my portfolio, I decided to write a book. Patrick Renvois, co-founder, author, and speaker, Sales Brain. The team of 13 that paid for Instagram. Daniela Bernardi lands at Facebook in 2011. Pre-IPO, on a team called Solutions Engineering. They work with advertisers and developers on the Facebook API, an ecosystem about the size of OpenAI's today. His boss jokes that the team made the money to buy Instagram. 13 people, a run rate of $1 billion a year. 2 posters shape him for life: What would you do if you weren't afraid? and Think wrong. Years later, after surviving 3 different versions of Twitter, he quits without severance and builds Toolhouse, an AI platform that turns agents into APIs in 3 commands. He carries the same Facebook habit: challenge the status quo and go back to first principles. That story is from Tony Robbins says that people do things for 2 reasons: either inspiration or desperation. My dad was an entrepreneur. He worked every waking hour of every day. He would be out the door before I got up in the morning, and he would come home after I went to bed. Charles Gaudet. CEO, predictable profits. 2 pop discs and a mattress company is born. Jeremiah Curvers spends more than a decade in marketing and technology and has no interest in mattresses. When a friend who makes foam in Montreal suggests a direct-to-consumer mattress business, his answer is, Mattresses? Really? 3 weeks later, volunteering at a charity golf tournament, he lifts a heavy box and— Both my legs just left me. An ambulance arrives. 2 popped discs. For 3 months he walks like a 9-5-year-old, and a bathroom trip takes 15 minutes. Bedridden, he calls his friend back and asks to work on prototypes, a very selfish project to build the best bed for himself. That became Polysleep. It makes its own foam, in one Montreal plant, while rival Casper burned through investor money, went public, and was bought back by private equity. That story is from. I'm not one of those geniuses able to start a company in their early 22s. I always wanted to, but I never had the conviction about why I'm the one, why I'm better than you at doing this. I have to convince myself first. Carmen Lee, CEO, Compute Exchange and Silicon Data. Broke in a Bangkok hostel, he invented a niche. About 15 years ago, Vic Dorfman lands in Thailand with a broken laptop and more than 20 grand in debt. Every morning he goes downstairs in his hostel, jumps on the Wi-Fi, and trawls the Warrior Forum, asking anyone for work. Can I write an article for you? Eventually he lands on SEO and builds a course called Smart Keyword Research, delivered as a membership site. One member asks if he could build one just like it. He says yes. That member refers another. Then it dawns on him that nobody owns membership sites as a positioning. So he simply starts calling himself the membership site expert. figuring it out as he goes. Years later, MemberFix and MemberHost serve million-dollar WordPress membership businesses, including the leadership company Echelon Front that story is from. I'm taking the actual position on behalf of the bank. So I've been betting on myself for 20 years prior. Why not do it in something that I believe in and really want to focus on? Andrew Pudilov, founder and CEO, Rush Bowls. Everyone said America's water was fine. Then Flint. It is 2015, and Dollavant is taking her mentor's invention to market. He is 87 years old, the first African American to own a bottled water plant in the U.S., and his filter mimics the human kidney. The big companies love it. Then they say no. This is amazing technology, but we don't need it. We're in America. Our water is fine. About nine months later, Flint happens. A hundred thousand residents are poisoned by what comes out of their taps. Everyone marches and blames the governor. Avant, a Harvard-trained data scientist, sees a human problem: Why are humans the sensors alerting us to water quality problems? She can't find a solution, so she builds one. That is how Aquagenuity starts with the AquaScore, a weather forecast for water. That story is from: Had Bill Gates been born 10 years earlier or 10 years later, he would not be Bill Gates that we know. He's a smart, hardworking guy, but he was at the right time and the right place for a software technology that was needed. Timing is everything. Michael Shermer, founding publisher, Skeptic Magazine. A Wife, a Saturday Breakfast, and 7,000 Customers. Jesse Hopps has built the world's largest subscription library of business playbooks, tools, and templates, about 7,000 customers, An inch deep and a mile wide. His top clients are Fortune 500 firms, so he flies around the world running workshops that score beautifully. 3 weeks later, he calls to ask how the plan is going. The answer, again and again: We haven't really looked at it since the workshop. Then one Saturday he promises his kids breakfast, but keeps working on email. His wife, who left Colombia for freezing Canada, says she didn't sign up for this. He comes clean: getting paid is not the same as moving the needle. When a former client asks for another upskilling academy, Jesse says he doesn't want to repeat what failed and proposes a different approach built on intrinsic motivation. That story is from— When we started to look at this, it was 2018, and there was no fund dedicated to that investment thesis yet. A few years later, we are managing $250 million. We've invested in 35 companies worldwide, and we are a team of 10 people. Olivier Tonneau, founder and partner, Quantination. A teenage journalist follows KISS to Japan and stays. Elise Krentcil is still in high school, freelancing as a journalist in New York, when she makes a strategy: become the New York correspondent for British and Canadian trade magazines, her ticket into boardrooms. Then KISS's manager calls and invites her on tour in Japan. She says no. 3 weeks later, he calls again, and this time she says yes, because she can write whatever she wants. She is one of 9 journalists on the trip. The band goes home. She doesn't. In 1977, Japan feels like a spaceship, with sliding doors at retail and bullet trains the US still lacks. She starts Dorna Publishing Agency, a booking and talent agency, introduces punk rock to the market, and hits 6 figures. Her first venture is her first home run. That story is from— I moved to New York from Toronto, and I couldn't get a bank account. I couldn't get a place to live, and by Canadian standards, I had perfect credit. How do we make it easier for the nurse from the Philippines or the doctor from the States? Andrew McLeod, co-founder and CEO, Certain. The government law that should have killed his company. In 2005, Yeleo Keremi's banking software company faces a death sentence. Nigeria's central bank, run by a Harvard-trained economist, orders banks to consolidate. About 89 banks must become no more than 25, and nearly all of Okeremi's small bank clients are about to be absorbed. His company has about 10 employees. He holds 4 board meetings in 1 year, and the sensible answer is to scale down. The board chooses the opposite. Either you shrink and die, or you expand and try fighting. They hire, advertise, and Okereemi starts speaking publicly. That year he finally meets the bank CEOs who once felt out of reach. By the end of it, he realizes that their competitors are now global. The company that began with under $60 has never raised capital. That story is from— I wrote a couple of business plans and thought about what my one big idea would be, and I didn't have one. So I had to check myself on that and ask where I could actually bring value. Mike Winterfield, founder, Active Impact Investments. 3 founders, 1 house, no work on Sundays. Mark Evgenyev's company, Dsync AI, has pivoted from a due diligence tool to a web scraper to a dataset of every Catholic parish in the country. The buyer, he says, finally showed up. They launched in January and, 3 hours later, hit revenue. Now the 3 co-founders live together in Nashville, a minute from a neighbor who runs a Catholic founders' group chat. Every weekday starts with a prayer and a standup with rotations. Saturday has no standup. Sunday is Mass and no work at all, which he says has changed his life after years of 7 days a week with no rest. Decisions get settled faster because he can just walk downstairs and knock. He does all the sales. Jackson runs product, Max runs data, and they have an archery range out back. That story is from— I'm an audience interactive experience designer, and my coping strategy is 100% finding joy in the journey. Someone asked me, "Did you make your coping strategy into a career?" I said, "Oh yes, I did." Barbara Ann Michaels, Jester of the Peace, founder Humorville. The IRA statement he forgot he owned. In 2013, Eric Satz is running a venture fund with friends when he opens a retirement statement from Fidelity. He has completely forgotten the money is there. It is long-term cash he cannot touch until 62 and a half, and he wonders why it is not invested in the very companies. He is backing. He is not sure it is even legal. It turns out it is. The process takes him 10 weeks, he does all the work himself, and at the end he writes a check to a custodian who did nothing. Why am I writing somebody else a check? he asks. He digs in and finds an industry that has barely changed since 1973. There are $19 trillion in IRAs, maybe 2% in alternatives. He found Zalto, And today it serves 60,000 customers and about $12.5 billion in assets. That story is from: We founded an all-beliefs church in March of 2020. We had to pivot from brick and mortar to online, and it couldn't have been a better thing for us. It took off and became a global movement. Now we have 1.3 million members across 113 countries. Amber Meixel, founder, Suivera. When Helos started, I didn't know anything about footwear. Within our first 18 months, we launched 5 of our own product lines to de-risk and learn how to do it. Founder and CEO, Hilos. I came out of the music touring world, and that world of access was really traded on favors. You scratch my back, I scratch your back. But 0.01% of the world has access to that. 99% of the world has their eyes on it. Having 99% of the world as a clientele pool is a pretty solid place to start. Lee Barcalow, CEO and co-founder, Current Group. I started in the online world after my son Jack was born. I wanted to earn money from home without leaving my 4 kids. I tried and failed for many years. I just kept spending money and my husband despaired, until finally I decided to jack it all in and become a vegan bodybuilder. Kim Constable, When we started, we were laughed out of every trade show. All the industry experts told us it would never work. We stuck to it, and we've now done hundreds of millions of dollars in revenue. Founder, Harbor. They asked me to pay for the training to get the job. I had never had to pay for a job in my life. I didn't have the cash, so I asked my girlfriend to put it on her credit card. Founder and CEO, AdMRR. I am not an accountant, and I am currently one of the fastest-growing accounting companies in the country. That really pisses a lot of people off, and I very much enjoy the ones that will admit it to me. CEO, Decimal. In 2016, the mayor of Palo Alto wanted to ban software development. He felt there was too much traffic and parking, so he wanted to drive out the tech companies. Software was technically not an allowed use, even though this is where Google, Facebook, and HP started. Greg Tanaka, CEO and founder, Percolata. The round was priced at about $4.55. By the time it closed and people got their securities, it was at $28 or $29 a share. I immediately had a lightbulb moment. Why don't we just focus the whole business on that? Robert Stevens, court-appointed receiver. Strongbow Advisors, Somerset Capital. My classmates were getting wealthy as management consultants and investment bankers. I went to work for the Solar Trade Association for $4 an hour. I fell in love with solar, but it was a mistake. I was too early. CEO, Tandem PV. You may be a good doctor, but you're just giving people pills they have to take for the rest of their life. If you have blood pressure, you take this pill. If you have blood sugar, that pill and that injection. I felt like we're subscribing people to a lifelong prescription. Chairman and CEO, L-Nutra. The research companies I worked at, and the whole ecosystem really, was a sweatshop environment. 80-hour work weeks, put bodies in seats. Women had to make a choice I didn't want to make between ambition and family. Founder and CEO, I wanted to build mind-controlled wheelchairs. Then I found that over half of wheelchair users are not there because of some traumatic event. They have a neurodisease that wasn't treated. I personally believe we can prevent wheelchair use by over half. Founder and CEO, Vistem Labs. I became a father, and many new moms are pumping breast milk and keeping it in pouches. I remember looking at those pouches thinking, These are full of antibodies. What if those antibodies could be functionalized into a new therapeutic medicine for immunodeficient patients? Co-founder, Lactiga. When I started in venture, I'd have cleaned toilets if I could get an hour a day to learn from these people. The moment I knew I was good at it was when a founder with lots of choices chose to work with me. General partner, Outset Ventures. A good training as a scientist does not really prepare you at all to run a company. I thought if I knew the science, then anything would follow from that, but it's almost a completely orthogonal set of skills. Nina Horowitz, CEO, ImmuneBridge. My father got sick with cancer, and sitting on what turned out to be his deathbed, he held my hand, looked into my eyes, and said, Son, I regret so much in life. He was a Welshman. Not emotional. That moment was where all the adventures began for me. John Llewellyn Davies, founder, Freedom Founders. I was working 18 hours a day, got really sick, couldn't do that anymore. I could work 1 hour a day at most. That question of what you would do if you could only work an hour a day has driven all the books, the speaking, and the coaching since then. Founder and business coach. Less doing. The more I got into aging in academia, the more snake oil I discovered in the field. Aging is never going to be solved if you just do everything as everybody does— sleep well, eat well. That will still result in cancers, Alzheimer's, and people still die a very bad death. Founder, Healom. The majority of films the average person sees are big-budget Marvel movies with $100 million budgets, and 50% of that is going just to marketing. The smaller films between one and five million really aren't getting the financing they need. Sharif Bennett, co-founder and chief evangelist officer, Cineblock. We developed this partly because of an allergic reaction that one of our founders' kids had to mosquito bites. The first step is to detect them. If you can't track it and pinpoint it, you can't eliminate it. Suki Friedman, CEO, Bzigo. I started at 39 years old. You either get lucky and get thrust into a movie and you're an automatic star, or you move up the ladder slowly. Commercials, one-liners, two-liners, supporting cast, and now my first lead. I think that was better for me. Actor. I realized the most value being created was not me at the factory. It was me on my commute between the hotel and the factory, realizing, wait a second, this is 10 years ahead. I need to import back what's happening. Tom Hegarty, founder, Letgo Car. Black homeownership in this country has stayed literally the same from 1968 to 2025. We've had the same 30-point gap for a very long time, and with a lot of good intentions from regulators and banks, the problem still hasn't been solved. Casley Johnson, founder and CEO, My home pathway. I was in my first semester at Copenhagen Business School and got a call from Nick, who said, "Drop everything you're doing for six months and read the white paper." I came from a non-tech background, so it was a steep learning curve. But I dove through it paper by paper. Peter Gillardy Mickelson, COO and co-founder dial. I'm an adopted kid, so I think part of the drive was feeling like there was no one coming to save me. that I didn't really have any fallback. So I always figured I had to take care of myself. Founder and CEO, NYT bestselling author, Health Business Growth Collective. I like golf. I just don't like it that much. I can't play it every day. After I sold the company and retired, I needed to do something truly impactful. Founder and CEO, Advynal Medical. He pulls out a cigarette, Lights it up in the office because this is back in the 90 seconds before HR and all that stuff came to be, and he's like, "I'm just messing with you, kid. Don't worry. Come in on Monday at 7 a.m., and we'll get you started." Ari Baum, founder and CEO, CFP, Endurance Wealth Partners. I was a little burnt out, so I thought maybe I'd become an individual contributor. It was one of the best moves I made because I quickly realized that's not what I'm wired for. I'm wired to lead something. Kate Williams, CEO, 1% for the Planet. We saw the sliding scale. The majority who have no money, no training, no equipment, mining with stones tied to sticks for hammers, climbing down 200-meter shafts with nothing more than a rope. Co-founder and President, Mwamba. We really thought our parents were going to buy it. We had no idea that 6 million people were going to be interested in this story. Founder, bestselling author and book coach, The Finished Thought. The fascinating part was similar to my early days in fraud: you're looking for a needle in the haystack. 99% of the time patients are healthy, 99% of the time the end user is not a fraudster. You're really looking for the outliers. CEO and founder, Lind. Chapter 2: The Part They Don't Put on LinkedIn: Layoffs, Lawsuits, Near Bankruptcies, burnouts, the stuff that actually teaches. I'd run good, as they say in poker. I'd hit a lot of green lights in life. On the surface, everything was fine, but I wasn't in touch with my humanity or my emotions. I was looking at people as strategic pieces on a chessboard. Ray First, 5x founder, investor, World Series of Poker champion, author, Full Tilt Poker former board member. In 2008, we were struggling, majorly in debt, maxed out all the credit cards, considering going back to find a job because we couldn't get the finances to work. By 2011, we were a million-dollar company. By 2015, we were a $10 million company. Joe Pulizzi, founder, author, The Tilt, Content Entrepreneur Expo, founded Content Marketing Institute, the CEO who dove for golf balls among alligators. At 21, grad student Jim Donnelly wins a business plan competition with a golf ball recovery company. His divers pull balls from water hazards in Georgia and North Florida, past alligators on the bank, then ship millions to France, Sweden, and England, where a Titleist sells for 2.5 to 3 times the U.S. price. One day Jim climbs out of a course, dirty and gross, and finds a man on the bank holding a golf club. Ready to swing. The man explains his wife just left him and he just got laid off. Seeing Jim made his day. I know now it can always be worse. Jim, meanwhile, has an MBA and a booming European business. Then he leaves for Ranger School, and the manager he hired empties the bank accounts. That story is from our very first investment had a three x liquidation preference. If they gave us five million when we sell. That investor gets five million, then another five, then another five. It was really punitive. We sold the business for something like eighty-five dollars million, and my son and I got pennies on the dollar. Philip Ogilvy, founder and chairman, Stack Construction Technologies. Even when it's clear to me they're not going to make it, you still have to be there for the founder. I was a founder for twenty-five years. I'm not going to abandon somebody just because they're about to fail. It's not paying any bills, but it's part of the human I am. Ben Narasin, founder and general partner, Tenacity Venture Capital. The kid who sat in the lobby for a month, every year. Every fall, David Chadpour's mother drops him at a private school in Beverly Hills. He is not enrolled. No application, no financial aid, nothing. He wears the uniform and sits in the lobby. When she picks him up, she asks how it went. My guy didn't go to school. I sat in the lobby. Her answer? Oh, that's okay. You'll get in school tomorrow. It takes about a month each time. It happens in 3rd grade, then 4th, then every year through 8th. Finally the head of school feels bad and lets him in. David hated it then. Now he credits it with his grit and with a belief that anything is possible if you want it badly enough. He later builds Social Native, which gives 1.8 million creators a second income. That story is from I did it two or three years too long. When it's not coming together, you just got to say it doesn't make sense. We got to move on. Craig Carroll, founder, Certus Insurance. We'd invested a couple hundred thousand in molds and product on our credit cards. I got the first customer complaint, a very nice one, and I fell onto the floor and thought, "This is it. We're bankrupt." Lena Phoenix, co-founder, Zero Shoes. A 4th grader on a Gulf War refugee bus, laughing. Lloyd Lobo is 8 or 9, in Kuwait, when his mom wakes him in summer and says they have to leave the country now. His first thought: Nobody will find out he failed 4th grade. Then he sees the worry on his parents' faces. Currency worthless, security gone, bombings in the distance. In his building, adults skip the complaining and organize. One guards the door from 6 to 12, Another from 12 to 6. Someone arranges food, someone finds shelter. Word spreads building to building with no phones, no internet. He ends up on a refugee bus from Kuwait through Baghdad to Jordan, past buses bombed on the Highway of Death. The adults around him are smiling and playing guitar. I'm like, why are they laughing? Decades later, that bus is the root of his book on community-led growth. That story is from... Anyone can sell a dollar for 50 cents, but you just can't do it for long. If you're selling dollars for 50 cents, it's gonna fly off the shelf. WeWork's business was a little bit like that. It was too good to be true. CEO, 90. I literally had the world in my palm, and Google woke up one day and said, nope, you need to restart. That paper mill is what tore me apart, and it led to me using my body as an amusement park. Brian Fikes, founder, Bonsai Marketing. 2 years, a slick product, and zero closed deals. Juan Luis Betancourt has a product everyone calls groundbreaking, a plugin that reads personality data and tells you, mid-Zoom, who you will butt heads with. It demos beautifully. For 2 years, nothing sells. Looking back, he counts 5 reasons: no buyer because no company has a head of collaboration, No budget. Trials stuck in a 6-month IT security review. Teammates who already know each other do not need it. And a plugin that needs training. So he tells his team, make it idiot-proof and addictive like crack cocaine. They rebuild it as a single open question bar, like ChatGPT. Demo to trial goes from 20 to 1 up to roughly 19 of 20. Then he sets a binary deadline: $2 million by year-end, or he sells or closes the company. That story is from— we did that first product for almost a year and a half. We had customers, we had usage. It felt like the real thing. But every single sale was an uphill battle. The burning need just wasn't there. Everything felt grimy and forced. CTO and co-founder, Contour YCS '23. Every time I would pull a trigger, there was a moment of sheer terror of, dear God, please don't let me have missed anything. Don't let me have not seen that kid. Don't let me have not seen that family. Kate Van Dam, head of strategy, Skyfi. Seven days before Lehman, he finally climbed out of debt. Chris Snook discovers entrepreneurship at 22 through Think and Grow Rich, then promptly falls half a million dollars in debt. He climbs out by 2004, flips a property in 2005, and gets back to even. Then comes 2008. I came out of my hell in that scenario seven days before Lehman Brothers went in. Years of building, and then he goes bankrupt. Two point seven dollars million this time—an event that is unrelated to the financial crisis but lands right in front of it. He spends 2009 and 2010 realizing the world did not end. He rebuilds in software. Then, in 2021, landing in Dubai to launch a company with fifty dollars million in pre-sales. He learns a partner has committed fraud, and he shuts it all down. His takeaway is simple: no one gets out of this game without bruises. That story is from We Were Rejected So Many Times. The first thing the lady evaluating us at the university said was, oh, you're sending spam, right? I don't know how many times I heard email marketing is dead. Stefan Skibesta, Chairman of the Board, Brevo, formerly Sendinblue. My first team was all from Facebook, Google and Coinbase. They left super lucrative jobs because they wanted to build the next Facebook or Coinbase, not to be acquired. So I definitely felt guilty, like I was letting them down. Amy Yin, venture partner, Defy VC. 4 nights without sleep, a crash, and a boss who didn't care. Alan Gobbs is a young vice president at an investment bank when his managing director promises a client a financial model in 1 week instead instead of 2. The target is EADS, the European aerospace giant. Gobbs leads the effort and does most of the work himself. He does not sleep for 4 nights. With no driver available, he drives the printed material to the client himself. On the way back, stuck in traffic, he falls asleep at the wheel and crashes. He calls his boss. The answer: I don't care, you have to come back to the office. Gobbs leaves the car where it stopped and goes to work. Years later he calls it an army and credits it for his discipline and for learning Exactly how far a body can go. That story is from one of the things I did wrong was not really value my team as I should have. I was always micromanaging, thinking I could do it all myself. If you want it done right, you give it to the person who's really best at it and let them do it. Anushukla, co-founder and executive chairman, Botco.ai. The burnout happened because I did for too long things I did not enjoy and did not see the end of. I had a team of ten, and I didn't like being the operator. The answer to more is not always scale. Eric Yang, founder, Lead Next Gen, SaaS Growth Summit. A finance guy buys a Vietnamese soup restaurant in Dallas. Alan Zhao has just watched the AI assistant startup he works at fade ahead of its time. Then a close friend from high school calls. He wants to open a restaurant and asks Alan, the finance guy, if the numbers make sense. The place does 500,000 inches revenue, Costs $200,000 to buy, and nets $100,000. Payback in 2 years, then cash flow to fund their app ideas on the side. Alan, bright-eyed and bushy-tailed, says yes. Reality arrives quickly. He wakes before dawn to hunt for jalapeño peppers when the kitchen runs out. And there is a basic flaw: we serve Vietnamese hot soup in the middle of Dallas, Texas. All sales come in winter. None come in summer. It is the most exciting and hardest thing he has done. That story is from— There were 2 times in my life that I passed out from stress. One was romantic and one was professional. There was no money in the bank, payroll was tomorrow, and we literally did not know if we were going to make it. Ari Goldberg, founder and managing partner, R+MKR. My first company pivoted 4 times. The 5th product became the sales intelligence product. The first four products failed in the first two years. Second company, we pivoted twice. The third product succeeded. Arjun Pillai, co-founder and CEO, Docet. The two one-year-old who tried to import wine to Hong Kong. Gabriel Jaroson spends a summer in Hong Kong where everyone tells him the same thing: You are French, so import French wine. He is 21, alone, and quickly learns importing and exporting is hard. And alcohol is a whole other level. So he builds a website instead, a marketplace for French wine, copying Amazon's third-party model. He hustles 16 hours a day in my 2-by-2 meters dorm, drinking 10 green teas a day. He never does the importing. The site grows anyway, and he learns SEO along the way. After 4 or 5 years he walks up to his competitor, who has 25 producers to his 150, and tells him point-blank he wants to sell. Yes, that story is from— people think being a founder is just exciting and great. It's hard. I actually didn't struggle psychologically with growing any of my businesses. The bit I really struggled with was once I'd sold them and stayed in the corporate. That killed me. Founder, Storyboard. That was incredibly naive because you don't know what you don't know. That's the thing about this business. When people come to me and ask, should we go into this business? I'm like, stop. Let me explain to you everything that we've learned. Andrew Schmertz, CEO, Hopscotch Air. From grocery cart pusher to Mark Cuban's mini-me. Benjamin Stern wants to work the day he can get a child work permit at 14 and a half. He takes a sub shop job and pushes carts at a grocery store, saving every dollar to put into his first company. By 18, he is grinding 16-hour days running startups and an agency. As a student, he wants better focus, so he mixes ginseng, B12, caffeine, and L-theanine, hires scientists to build a formula, and launches a nootropics brand. He lands on TV, where Mark Cuban calls him his mini-me. But the company sucked at sales and marketing. His co-founder isn't an entrepreneur, and the business goes to the ground. Leaving a $100K debt. He pays it. That was my moonshot, he says, and years later he is still recovering. That story is from: I accidentally raised $50 million from one investor for Formula One electric racing. Two weeks later he invested. I didn't get a dollar out of the deal. I didn't know how to protect myself. You learn a lot more in the real world than you would in school. Brandy Koloski, General Partner, Sacral Capital. I lost eighty grand on the boat. Boats tend to entropy fast. Two years sitting in New Zealand, the gel coat cracked, the awning got whitewashed by the sun, and then New Zealand shut down so drastically during COVID that I couldn't reach my asset. Emmanuel Lavoie, CEO Jetstream. A kite dragged him across boulders and changed his career. Nick Goldner has just stepped down as CEO of his biotech company, exhausted. When he goes kiteboarding, a dozen warning signs nag at him. The wind is gusty. A woman who helps him launch says she is not sure she is qualified. He ignores it all. Then the kite rips him face-first into the mud and drags him 100 feet across a rocky beach. He pulls the bar to create tension, launches 15 feet into the air, and a gust smashes him down 50 feet away, like Hulk and Loki. He dislocates 5 ribs and pops them back while walking. A trauma surgeon from Stanford happens to be on the scene. Goldner is flown to Stanford by helicopter. His first thought is, don't die; the second, don't get paralyzed. Months later, he sees it clearly. His company was the same crash. So he let go. That story is from There Are Times I Kick Myself. If I had the ability to build the business, why didn't I get into the equity conversation? I wasn't on the cap table when we exited. I got a lot of experience out of it, but maybe I shouldn't have spent 7 years doing that without equity. Johnny Page, Chief Revenue Officer, SaaS Academy. They seized 10,000 of our books that we had just published, called Ginseng: The Root of Life, and burnt them. We didn't have money for the lawyers. It was like a SWAT team, yellow tape, all these boxes unloaded from the basement of my house into the van. It's like a crime scene. Ronald M. Bazar, CEO and co-founder, TastyPicks International. The kid with the Harvard brochure. A one 4-year-old Israeli boy is caught by his parents holding a Harvard Business School brochure. They ask what on earth he is doing with an MBA program. The dream sticks. Years later, he works for an Israeli company called Giga with an office in Palo Alto, and he realizes he can get a top MBA right in the Bay Area. Itamar Novik moves to Berkeley in 2010, straight into the aftermath of the financial crisis, just as mobile and cloud begin to unfold. Exactly the right decision at the right time. He ends up at Life360 and, while running it, quietly starts moonlighting as an investor. Founders keep asking him to invest as an angel. 2 funds and 50 to 60 deals later, he has backed 2 decacorns and 4 unicorns. That story is from— between 2010 and 2018, about 9 years, we paid ourselves almost nothing and every dollar went back into the business. We laid everyone off on one day. There were 3 people left. CEO, DevHub. Even as head of product, you can't fix it if it's an issue with the business model. When the business model is ads-based and you're a public company reporting quarterly earnings, You can't pull back or you're toast. CEO, Digits. 50% pay cut, 1 hour, everyone said yes. March 2020. COVID has just hit and Niall Murphy's Internet of Things company, Everything, has a round in the bank but no idea what comes next. He gathers his team and says he wants everyone to survive. I'm going to take a 50% cut in my salary. He asks his senior leadership to do the same, and asks everyone else in the company for a material cut, So that nobody has to be let go. Within the hour, he has 100% opt-in from a team of more than 100 people. He calls it one of the proudest moments of his career. The culture, he says, is the point. An empathetic, we are in this together way of working rather than my way or the highway. He sells the company in 2021. That story is from— We got crushed in 2008, the whole tanning industry. Then in 2010, the government tacked on a 10% federal excise tax on tanning services. That pretty much put the nail in the coffin. I always tell folks, there's only one way out. You have to invent your way out of it. Stephen P. Smith, Principal CEO and Founder, HOT AORX. The end of my Overstock career was really over a drug and alcohol addiction problem. Trying to relieve the stress of having the Russian mob trying to kill you and being responsible for growing over $1.5 billion worth of revenue at 27 years old. There's no training for that out there. Jeff Atkinson, CEO, Huckaby. How Intel Options Ended a Trading Empire. Michael Frank runs a specialist and market maker firm on the American Stock Exchange, up to 50 people strong. In 2000, he makes more money than a kid from Queens could imagine. Then Intel gets listed on multiple exchanges overnight. After 10 years trading it, he knows where volatility should sit. But now other exchanges post quotes below his bid and above his offer. Brokers ask him to honor them, and the only way to get to them is yelling at a broker to phone someone on a different floor, which takes minutes. By then, the quote moves. He is forced to buy above his offer and sell below his bid. We went from being the casino to the players playing blackjack and craps, he says. In 2001, he loses more than he ever imagined. Then 9/11 hits in the middle of the sale, That story is from. The game for a serial founder is don't run out of cash until you figure out product market fit. Pixar couldn't sell the computer, so they had to make the movie to show what it did. Ravi Komathiredidi, MD, founder and CEO, Daytona Health. I was part of the bank that failed, and I was promptly fired. All my life I've been a Type A personality. I've never been fired from any job. It was ego hurting, and it was humiliating. Bala Kamalakaran, founder and managing director, Startup Iceland, Iceland Venture Studio, a winery, too much wine, and a CEO job. Steffi Bau is a retired motocross champion with 2 destroyed ankles and a new identity to figure out. One evening in Italy, she is tasting wine at a winery with a friend when the owner starts talking with them. He turns out to be an investor in Fantic, the Italian motorcycle company founded in 1968, And he realizes she lives in America. We should talk with the CEO, he says, and the bottles keep coming. That night, a little drunk, they call the company's CEO, who already knows her from her racing history. The company wants to enter the U.S., and by the end of the call Steffi is offered the job of running the American branch. She runs it for 4 years, focusing on e-bikes just as the movement begins. Her lesson: Never be shy about what you are good at. That story is from. I remember sitting at the front desk in our first location, in this little strip mall, watching people just walk by on the sidewalk and not come in. It was so lonely and so stressful. There's no one else to talk to. Flora Wapples, founder, MD, Restor Medical Spa. We all knew that 93% of our income came from that one company. It was a huge multinational. And then one day, one phone call. 60% of it disappeared. Founder and CEO, Kayne Aerospace. How a sports camera rig taught standard cognition to see. Rohan Arun's first startup builds 3D sports from 40 cameras in a stadium, years before anyone owns a 3D TV. Founder money dies in the 2008 crash, so he inherits the servers and raises $700,000 more. The market never shows up. Then the CEO of Standard Cognition, an Amazon Go rival, finds him. Their single-camera tracking keeps swapping shoppers, and a wizard behind the curtain manually fixes carts. Arun flies to San Francisco and wires up 40 cameras in their first store on Market Street. His trick is giant ArUco markers, a global coordinate space, and a nonlinear solver that shrinks error from feet to inches. There was one day that was really exciting where I finally turned on our algorithm and it all cinched in. The store launches, the payout lets him retire and digitally nomad for years. That story is from I literally ran my car into a 50-foot brick wall and almost lost my life for the 10th time. I had to sit down and actually count how many times I almost died. I had it at 7, then I discovered 3 more. Chad Weller, high-performance life coach, ultra runner, Chad Weller, High Performance Coaching. Lehman Brothers is underscored by the name of the book, A Colossal Failure of Common Sense. Very smart people took a lot of risks and lost their sanity. They doubled down on the risk, and it cost them even more. Executive Coach, Columbia University Professor, Author, Columbia University. The CEO who halved his company before the crash. Kevin Serace is running Perfect Commerce during the dot-com boom. The team is great, customers are signed, revenue is in the millions, and there is about $50 million in the bank. Then the crash hits. Seras lays off half the company almost immediately. His board is stunned and tells him this will pass. He refuses. This is a market correction that's going to last for years, and we're going to have to make our cash last. Fortune runs him in a famous photo with a headline about the adults coming home to Silicon Valley. He drops the foosball table culture, brings back old-style management, and measures everything with KPIs again. He is never a mean manager, he says, but it is not all fun and games. A year later, everyone agrees he was right. That story is from: We had our best month ever in January 2020, just close to a million euro in revenue. 4 months later, we had exactly zero revenue. That was a bit tough. David Gunnarsson, CEO, Dohop. I had this big ego. If I know how to code, why would I outsource to anybody? I would code everything myself. As a dev, you have this developer ego. Prashant Mahajan, co-founder and CTO, Clicker, branded an African scam—he funded a game with shares. Olivier Madiba is in Cameroon, ready to launch his studio's first Kickstarter campaign. The interface throws up a red flag: his country is not allowed. So the team moves to Indiegogo, where backers decide it is surely an African scam. He calls it really, really humiliating. With no way to raise the money, Kiro'o Games improvises. The studio sells shares of itself online, a form of equity crowdfunding before the practice had a name. Madiba trains a team of illustrators and programmers in 2 months, and with no money for Unity or Unreal, they build their own engine. The game is a technical success and a financial disappointment, With plenty of copies sold and little cash back to the studio. Two decades later, he is still building. That story is from everybody's balance sheet was swollen, so you feel cocky. Companies with a hundred million in cash were out of business and bankrupt within eighteen months because they didn't make the changes they needed to. Rich Weidel, CEO, Princeton Mortgage. I was an early investor in Vector. It raised a Series A led by Sequoia and a seventy dollars million Series B. I thought I was the smartest guy in the world. They went bankrupt 12 months later. Partner, Active Impact Investments. Profitable in month 1, frozen by the SEC in month 2. Joe Raetz starts Dragonchain inside Disney in 2014, open-sources it in 2016, and goes commercial in 2017. The launch is a dream. 500 businesses signed up day 1, profit in the first month, a multibillion-dollar market cap. Then, in 2018, the SEC comes after him. He did not even have to stop operating. Regulators schedule threatening interviews with his customers, and every one of them drops out, citing budgets. A few early believers stay, including one who was quizzing Joe about the tech while he was still at Disney. 7 years later, the case is still unresolved. The company runs on a frugal budget, builds tools for the day it wins, and the founder has lost some color in his beard. He is convinced the fight is nearly over. That story is from— A lot of deals fall apart before the finish line. It dies at the 11th hour, or the buyer can't get financing. It's devastating once you've sunk the time. That's the most challenging part of the job. James Creech, founder, Quartermast Advisors. How many guys in the 1,970 seconds dropped out of college, moved back to their parents' house, started up with their buddy, And never made it. The answer is nobody knows because nobody writes biographies of those guys. Probably 99 out of 100 never make it. Michael Schirmer, founding publisher, Skeptic Magazine. Three days, one plugin, and people begging for links. After ten years of startups, Michael Yagudayev goes looking for designers' complaints. He reads the Figma forums using a technique called sales safari. One request keeps appearing: export animations as GIF and video. Nobody is doing it, and he is not even sure it is possible. He and his new co-founder give it 3 days. It works, to his surprise. They post it on social media. People were chasing us down for the links, something that never happened to him in a decade. They give it away on Gumroad, then try pay what you want. People pay $1, $10, $15. On December 31st at 10 PM, payments go live, and Michael goes out for a drink. 2 days later, January 2nd, comes the first paying customer. Within 7 months, they have 58,000 downloads and $5K in monthly recurring revenue. He never uses his ski pass once. That story is from— I'll talk anybody out of building restaurant tech. It feels so cool and sexy, but it's a huge slog. There are so many ideas like ours in the space that are great ideas and terrible businesses. In 2005, the Indianapolis area built about 15,000 homes. In 2008 to 2009, they built about 3,500. Whatever business you're in, imagine the market going to 10% of what it was within a few years. The vast majority of builders went out of business or into bankruptcy. Derek Wilder, CEO, Hallmark Homes. The deadline was March 31st, and the call went badly. Zombor Pirok's studio has cut its team in half after the games industry collapsed and publishers vanished. He tells his remaining people there is a deadline: if no client signs by the 31st of March, notices go out. That day is a Friday. A potential client says they will either sign today or never. The call goes terribly wrong. It was very obvious that it went wrong. Then a message arrives. They had completely misunderstood him and thought he was conning them. Another call is set for the next day. Zsombor goes to sleep Friday night believing he must tell the team on Monday that it is over. On Saturday, the client signs. The studio survives, and he never forgets how close it was. That story is from... My first run of paper was 100,000 sheets, and I was literally selling a couple of sheets every few days. My wife was very tolerant about the amount of paper stacked in our basement. Kyle Ewing, CEO, Terra Slate. I bought that business in 2008, going into the Great Recession, and our sales dropped 60% over the next 2 years. But we had a strategy, did some work in China, and when the world recovered, we took off. We used the recession to improve the business. Andy Harris, President, North American Strategies, STS Capital Partners. The worst clown in class fell onstage and wept. Barbara Ann Michaels is a smart kid who learned early that she had better have the answer, or things go wrong. Then she enrolls in clown theater at the Celebration Barn. She is, in her words, an absolutely terrible clown. She tries to be a stand-up comedian. She cannot figure out why people laugh when they do. It feels like total failure, and she has so little capacity to process it that she collapses on the stage and starts to cry. Her teacher, Julie Goel, walks over smiling and laughing and strokes her hair. In that moment, Barbara understands that clown theater is about laughing with the failures of life, and that by failing so dramatically, she has started to do it right. She lets herself off the hook completely. That moment becomes her career. That story is from— At my heyday, I had 15 reps at my broker-dealer. I routinely describe that as one of the dumbest things I've ever done in my life. and I've done some really stupid things. Court-appointed receiver, president, Strongbow Advisors, Somerset Capital. For most of my career, I've been earlier than late in a market, and when you're too early, it can be almost as bad as late. Voice over IP took 20 years to go mainstream. Video conferencing, which I worked on in the '90s, only became mainstream in 2020. CEO, Tandem PV. He sold a $300M firm, then couldn't underwrite a startup. Jesse Cole has already won twice. He builds a broker-dealer to a $40 to $45 million top line, and within 3 years of joining Merlin, that firm is sold to Wells Fargo for $300+ million. Then he co-founds Haute Hippie, a women's clothing brand with over 3,500 points of distribution and about $42 million in sales. And sells it to private equity in 2017. So he starts investing in early-stage consumer startups, and he is lost. I had no idea how to underwrite an asset, he admits. I had no idea how to qualify a founder. He is chasing what is trending on social media. After a year of personal checks, he stops and learns to separate a fad from a trend, a trend from a sustainable business, and a sustainable business from a monetizable asset. That lesson becomes his first fund, the Seed Lab, then Synthesis Ventures. That story is from: You have to be your own CEO. You have to be able to pilot with zero capital, get people to want it, then fail, fail, fail, fail, and then model up. I think that's the standard now. Anthony Berryhill, owner and founder, Elite College Hackers. Obama asked the team every day for 18 months if healthcare.gov would launch on time. They kept saying yes. He realized he never asked if they were confident. They were saying yes because they wanted that to be true, but they were scrambling under the surface. Founder and CEO, Alter Agents. Missiles fell around the farm, and the locusts stopped. Djortemir builds his company on a locust line that exists nowhere else, bred over 6 years to eat dry feed instead of expensive grass. Then war comes. His farm in northern Israel sits under missile attacks for about 9 months. The farm is never hit and the employees are safe, but the blasts shake the insects. At one point of time, we thought that we lost the entire crop, and that would be the end of the company. Tamir cuts production to bare survival mode. His launch, planned for November 2023, slips about 8 months because the war starts a month earlier. The tourists he planned to sell to vanish. So at 4:30 every morning, he runs 12 kilometers, and every day he films himself eating locusts for a challenge he calls the John the Baptist diet. That story is from. I was a minority opinion at Nurable. That's very often the case when you have a radical idea, and I'm definitely someone with radical ideas. James Hammett, founder and CEO, Vistem Labs. Casper was burning more than $200 above the value of a mattress to acquire a customer. It would have been cheaper to give a free mattress and $100. They raised money, went for the IPO, got kicked out of the exchange, and were bought back by private equity. Jeremiah Curvers, CEO, Polysleep. 3 failed startups taught him to sell a disposable cup. Paul Creighton spends years trying to get people to change their habits for the planet. His first startup, CO2 Cycle, helps film shoots go green. Until COVID clobbered it. Jibe rates the sustainability of takeout packaging. It booms in lockdown, then ebbs as people go back out. Aram, a chic tote for carrying 2 refillable bottles, dies because nobody wants one more bag. The lesson, learned the hard way, is that people love their habits. So Craden and his husband stop asking consumers to change and give them what they already want: a single-use cup. Made of aluminum, so it is infinitely recyclable and keeps drinks colder. We need to meet the market where it is, he says. Years of R&D later, Lumicup holds a U.S. patent and 5 sizes. That story is from— I came down with the first batch of COVID really badly, and it left me permanently deaf. I lost my inner ear and had to learn to walk again. The doctor said, that's the end of your mountaineering and flying. And I said, No, I'm coming back. Deryap John Llewellyn Davies, founder, Freedom Founders. 6 years ago, when I was 23, my biological age was 39. It was around the time I quit my employment and started the company. When I was working there, I was stressed that I wasn't doing what I want to do in life, and when I started, now I'm stressed that I'm not able to do it. Founder, Hilome. When you remove a toxic leader, the next leader is effectively impotent. There's a trust tax. The trust level is so low, they don't trust the next person who comes in. Performance doesn't improve, and you end up turning through two or three CEOs. Brian Hughes, principal, author of Toxicity: Clear Day Strategies. There's a huge push in entrepreneurship these days. People saying they're a founder on their X account. For this place, I've got overhead, rent, employees. This is certainly the harder way to do stuff, and that's why businesses fail. With a personal brand, you can pivot quicker because you don't have that overhead. Founder, Real Brave. We're at the 10th iteration of the business model. We don't know yet if the growth is there, but what I've figured out over the last year and a half is that the unit economics are really good. You just keep trying. Tom Hegarty, founder, Letgo Car. I played on enough high-performing sports teams to know this, and I was so pissed 4 years in that I didn't just apply what I knew about behavioral team accountability to my own company. Shannon Burns Susko, 2x exited CEO, founder, Metronomics. We bought into the truism of don't worry about profitability, it's all about revenue, but we couldn't make a dollar. The local price plus the export royalties exceeded the market value. Ed Cornu, co-founder and president, Mwamba. Just because you got paid to go do some great workshop that scored really well, if it didn't move the needle, it wasn't worth putting in the effort. I don't like working for money. I like working for impact. Jesse Hopps, founder and CEO, Demand Metric, Commercial Excellence Consortium. I'm a visionary. I'm a creative entrepreneur. I'm not a COO, so we went from four people to eighty people, and I almost had a nervous breakdown. It was great, but awful. Elise Krentzel, founder, ghostwriter, and coach, the Human Atlas Institute. A company in the UK actually stole our technology. Frankly, they had a booth next to us at a supercomputer show in Austin in 2015, and a year later, our technology showed up with their name on it. There was litigation, and we won. Herb Zien. That's one of the biggest mistakes I've ever made. I didn't take the stock. I was afraid it was insider trading, so I just took my payments in cash. In retrospect, I would have taken all the stock and defended myself if it became a problem. Starbucks was more successful because Schultz knew where to open his first store in Manhattan. I opened on the corner of 96th Street and 3rd Avenue. There are three things about a physical retail location: location, location, location. I got all of them wrong. Eric Satz, CEO and founder, Alto. Chapter three: Money, cash, pricing, margins, personal finances—the numbers people usually hide. We should be very stingy with our time and generous with our money because we can always make more money. I don't care if you're Elon or Bill Gates. You cannot make more time. Most people do the opposite. Author and behavioral designer, Hooked: Indistractable. Money should be a byproduct of doing great things and doing it the right way with the right people. It goes to your head a little bit when a company puts $140 million in your bank account. Co-founder and CEO, Humanaut Health. Microsoft went public for $400 million, and my eBay founder stock went from $15 to $615 a share in the first month. I sold all of it. Am I unhappy? No. Pigs get fat, hogs get slaughtered. Serial disruptor, author, keynote speaker, jsameet.com. When we sold, I don't even want to say I had $50 in my savings account, but it wasn't much at all. At Dealer Inspire, we didn't take a paycheck for years. Founder and CEO, Go Brewing. CEOs guess their growth right half the time. In Japan, every company must publish guidance one year ahead. Dan Rasmussen studies what happens next. If you sort companies into slow, medium, and high growth, executives guess their own category about half the time versus a third by pure chance. So why not buy the fast growers? Because of what the stock does. When a fast growth prediction comes true, the stock beats the market. When it misses, it dramatically underperforms because everyone was disappointed. Slow growth predictions, by contrast, cost little when right and pay off big when beaten. Run the sum product of returns and probabilities, and the edge vanishes. The forecast was right often enough to feel smart and wrong often enough to erase the profit. This is the seed of his book, *The Humble Investor*, and his bet against hubris. That story is from start charging two hundred bucks, start charging five hundred bucks. Whatever you feel might work, and maybe play around with that, and you'll be shocked at how serious your guests start taking your show. Founder and host, Entrepreneurs on Fire. 20 years ago, a qualified investor with $5 million of net assets meant a big boy. Now, these big boys are dentists. They have no idea what they're buying into, and they sign a letter that basically says, I'm a big boy, I can take care of myself. Since I own the site, I don't have to deal with any client requests. There's no more reporting, none of the stuff that would normally take up your time. But you still get the money. Your own stomach is a trap, and your mind is a trap sometimes. I'm tired of seeing just baking soda in the refrigerator. I'm tired of eating chips for dinner. That hunger affects your brain. Luke Cooper, founding partner, managing director, Latimer Ventures. The inventory that made investors nervous then made her a genius. At the end of 2019, Lena Phoenix has a problem. Tariffs are coming on footwear, so she and her Zero Shoes team load up on inventory from China. Investors look at the balance sheet and panic. God, you have so much inventory on your books. We're really worried about your financial health. She tells them it is temporary. Then the pandemic shuts China down, and nobody can get product out. The same investors now say, "Oh my God, you're a genius!" But in March 2020, sales fall off a cliff, and a large retailer cancels a big order. Zero emails its customer list: "We don't know if we're going to make it. We need your help." They put their best-selling sandal at half price and sell 20,000 pairs in a couple of weeks. That story is from. For the past few years, I've been saying we have a 50 over 50 chance of reaching longevity escape velocity within about 12 to 15 years. I have to, with a very heavy heart, tell you that over the past couple of years, that timeline has been slipping. The number one reason is we don't have the money to do our next big lifespan experiment. Aubrey de Grey, President and Chief Scientific Officer, Co-Founder, LEV Foundation. SENS Research Foundation. Once I got my first bonus, I couldn't believe my eyes. I ran a few kilometers, which I never did before. I was just looking at that balance. I was born in a very poor family, to be honest. Co-founder and managing partner, Adam Capital. It was a restaurant with 500,000 in revenue, a 200,000 purchase price, and 100,000 net income. The payback appeared to be two years. This was foolish me going into this industry, bright-eyed and bushy-tailed, knowing a little bit of programming. Alan Zhao, co-founder, warmly. I talked with 150 exited founders in the last two years, and every single one said, "I don't want to raise money anymore. I want a small team, mostly AI agents, and I want to be cash positive." I'm okay with one dollar's million in revenue. I'm okay with $50,000. Sahin Boidas, co-founder and CEO, Klaros Farm. The $25,000 check, that would have been $100 million. Duncan Logan is a Scottish farmer's son turned Swiss bank derivatives trader turned founder. By 2008, he moves to San Francisco and launches Rocket Space, a coworking home for venture-funded tech startups. Uber moves in. So do Spotify and Flexport. Naval, Fred Wilson and Jason Calacanis drift through the hallways. When Uber raises, Logan thinks the minimum check size was $25,000. He has not been working for years, and every dollar is going into the new company. He passes. Little did I find out that later there were some people who put in just $5,000 and they got $25 million back. Rocket Space later raises about $350 million, much of it from China. The money turns problematic, and Logan ends up returning the capital and winding the company down. a process he says is harder than starting one. That story is from: People look at revenue and don't look at margin. Selling €1,000 of wine, I'm making maybe €50. Selling a conference online, I share 20% with the speaker and keep 80. That's €100 in my bucket on €1,000. Managing Partner, Lobster Capital. We work only 9 months a year. After 12 weeks of work, we take a month off. If I want to buy a car, I can go and buy it. We're redoing the kitchen. It's a huge bill, and it doesn't make a dent. Sean D'Souza, founder, author of Brain Audit: Psychotactics. Customers we acquired in 2011 or 2012 still generate more or less the same revenue every year. So you effectively already have last year's revenue just by keeping the customers. You grow through new user acquisition, and if you can scale that, Chairman of the Board, Brevo, formerly Sendinblue. GPUs tend to fail. The mean time to failure is about 4 to 8 hours, and every single time a GPU fails, it costs roughly $300,000 depending on your run. Maybe $200,000. Founder and CEO, Lemurian Labs. A brother, a 3-year track record, and no way to sell it. Juan Colon says he became an entrepreneur by accident, and the accident is his brother. Juan has never traded. His brother, an independent trader, once lost some of Juan's money, then persevered until he built a 3-year track record worth marketing. Then he hit a wall. He had neither the skill nor the appetite to raise outside capital, and in Europe launching a hedge fund costs about €200,000 upfront. So Juan builds a platform where traders can expose their strategies to investors for €38 a month and keep a 15% success fee. One of them was the best World of Warcraft player in the world as a teenager. Now he manages 2 million euros and has made a million. The market is a massive online game, Juan says, because everybody is betting against everyone else. That story is from I'd rather raise a 100 million fund every 18 months than go raise a billion dollar fund and collect a lot of fees and figure out how to stuff money down people's throat that don't really need it. I charge $10K for the VIP day. If they don't raise at least $10,000 in sponsorship alone, I work with them until they get $10K or I refund them. So there's literally no risk. We've been right about 75% of the time on clinical trial outcomes. If you're right 51% of the time in the market, You're making a ton of money. CEO, Stealth Fintech Startup, formerly Resistance Bio. Fuel is up nearly 100% since March. Avgas was about $5.50 a gallon in March and it is in some places over $10 a gallon. I've never seen gas prices go down. We're probably living in a new normal. CEO, Hopscotch Air. No money in the bank, Payroll due tomorrow and a blackout. It is late at night at the Stylecaster office. Ari Goldberg is with his business partners, and there is no money in the bank. Payroll hits tomorrow. They are waiting on their lead investor, a self-made billionaire who has always been good to them, and there is nothing they can do but wait. We literally did not know if we were going to make payroll. The weight of it all lands at once. The obligations, the feelings toward his team, His own ego, everything he had envisioned. He ends up on a couch, blacked out from stress. The investor comes through, as he always did. Ari later sells Stylecaster to PMC, but he says that night is the price of admission to the entrepreneurial fraternity. That story is from Humira is a medicine a lot of people have heard of. Their patent just expired. Taking their last year's sales and subtracting this year's forecast, the delta between those two numbers is $20.5 million a day. Scott Stout, CEO and co-founder, Medvector. I worked as a software engineer for 10+ years and saved and invested a lot of money to buy this comfortably. My advice is buy a slightly larger SaaS. The smaller ones are very commoditized and a nightmare to run. The larger ones are more expensive but easier to run. Matthew Tse, CEO, ImprovMX. A lot of brands lose money and can't get out of their own way because their pricing structure is wrong, If you're not making about 45% margin minimum, you're starting off on the wrong leg and always catching up. Michael Blumenkrantz, founder, Primal Crisp. Most of our revenue comes from Google. Part of my job is to diversify our revenue so we can start to get away from that. That's job number one for me. Peter Rojas, SVP of New Products, Mozilla. A Wall Street analyst asks the old guys one question. Brian Bell is in his 20 seconds. A Wall Street analyst with a CFA making six figures. Every morning, he rides the six train, touching one-one strangers on the rail, heading downtown and wondering: Is this it? So he does something simple. He asks colleagues in their forty seconds, many earning millions as VPs, whether they would do the career over. They say no. Bell takes it to heart and runs a test. If he had ten or twenty million in the bank. Would he still do this? No. What follows is 15 years of dozens and dozens of jobs, from sales and marketing to product, an MBA, backpacking, living in Japan. Nothing passes the test until he starts investing in startups. Today, running Team Ignite, he says he took a 90% pay cut and it is way more fun. That story is from— I'm teaching what I call intrapreneurship. There's a route where you become an entrepreneur inside someone else's company. If I'd had 10% of the shares in that company, it's a totally different story. You'd see a lot fewer people get into life-altering debt for businesses they don't know how to scale. Johnny Page, Chief Revenue Officer, SaaS Academy. Most people burn out because they don't have the feeling of contentment. You say the day I have $10 million, I'm going to retire. Then you get there and go for $50 million. Than 100. If it's a moving goalpost because it's only money, you're never going to be fulfilled in life. Lloyd Lobo, co-founder, Bose.ai. The offensive side is significantly cheaper than the defensive side. Think single- to double-digit millions for a hypersonic weapon. On the defensive side, it's an order of magnitude more. One interceptor costs almost $120 million per shot. Sebastian Fischer, co-founder and CEO, We only sell the minerals at cost, break-even, or even a loss, and then it's a rev share with the brand. We don't get paid on what they make, only on what they sell, and only after they sell it. Under Armour's shirt might not sell at retail for 18 months. CEO, Hologenics. He sold his company, then bought it back for a dollar. Emmanuel Lavoie sells his travel-tech company to an American buyer and promptly buys a sailboat in Fiji. The plan is three years of surfing and sailing the South Pacific. Then COVID hits. The parent company fires everyone on its side and on his, leaving a shell and a Canadian asset it cannot figure out what to do with. His business partner, a crazy optimist, suggests buying it back for a dollar. Emmanuel thinks he is nuts since they owe two million dollars to suppliers. They do it anyway. Within three months, they own one hundred percent of the shares again. With 2.2 million in debt, Stripe wraps a pile of that debt and acts as their creditor on a two-year basis. Three years later, the business is five times bigger than when he first sold it. His boat, left in New Zealand, cost him 80 grand. That story is from our portfolio collected over 80 million dollars in non-dilutive grants, even though we only invested less than 8 million. Veronica Breckenridge, founder and managing partner. First Bite Ventures. It's death by a thousand cuts. You need HubSpot, that's $2,000 a month. You need a content marketing agency, that's $5,000. An accounting firm, that's $1,000. We were handcuffed to these expensive services. And once I got rid of them, it was like having the shackles off. CEO, Grow House. I was walking around with over a billion dollars in value in my pocket in a hardware wallet. I think I am not allowed to be a billionaire. I don't have the senator's blood or whatever I'm supposed to have, so they came after me. Joe Roetz, founder and chief architect, Dragonchain. Last year we did 7,000 surgeries for under $2.5 million US. For $25,000 US, you might get a new front door in Canada. Maybe a doorbell if we can afford to throw it in. Peter Lublink, CEO, Bethany Kids. Teenager with a backpack meets the Malaysian royal court. Simon Kelton is a long-haired teenager with a backpack and a £900 budget for a gap year around the world. He sleeps on beaches, under catamarans, and in the empty houses of strangers. Then he writes a letter to the first prime minister of Malaysia, claiming a family connection through his great-grandfather. When he lands in Penang, the chief of police is waiting, expecting someone in his 50s. Simon has put on a nice shirt bought in Hong Kong. I was swept through customs straight into a limo, he says, and driven to the palace. Weeks earlier he was sleeping in a bank entrance. Years later he is writing Eddie the Eagle and producing Guy Ritchie's Young Sherlock for Amazon. The year taught him one lesson: freedom matters more than money, and you can find adventure on almost no budget. That story is from... Back then, Hong Kong was Milton Friedman's wet dream. Zero capital gains tax, no dividend taxes, and no social safety net. You had 70-year-old seniors literally carrying up trash. Yat Siu, chairman, Animoca Brands. Day trading is not just algorithms. It's how people react to the news, what the sentiment is. I built that into my AI during the pandemic. I got 11x on Doge in 3 days and 9x on Nvidia over the years. Roboticist, founder and investor, Bearded Maker. We ran a 360 before and after. If the improvement didn't happen, I could extend the coaching at no extra cost, or take a cut in my fee. CEO, coach and founder, Progress U. I'm not concerned about what I'm reading. I'm concerned about what we don't see. That's what happened in 2008. If you'd asked experts at the beginning of the year, no one would have said the market would drop 54%. They'd have said up 7%. Chuck Garcia, executive coach, Columbia University professor, author, Columbia University. The ER doctor whose own doctor said, this is your life. Dr. Flora Walpole spends 15 years in the emergency room, where she learns that patients arrive because someone failed to stop a bad process a decade earlier. Then it happens to her. At 37, she is 30 or 40 pounds overweight and pre-diabetic like everyone in her family. Her hair is falling out, her joints hurt. She goes to her own doctor, a good one who trained in the same program. The answer: You are a 35-year-old mother of 2. This is what your life is. Flora refuses to accept it. She goes back to school for hormone certification, medical weight loss, and peptides. Now 48, she runs ultramarathons, does sets of 21 pull-ups, and is no longer pre-diabetic. She opens Restor with her sister, a lawyer, and grows it to 6 locations. That story is from— time is the key element. If you commit $1 million into a fund and expect a return in 10 years, that's different than committing $100,000 at a time and getting returns every 2 years that you can reinvest, your capital starts to multiply faster. Josh Wagner, co-founder and partner, Revenue Capital. We pitched against Google and found out afterwards that Google's proposal was 10x what ours was. We thought it was an aggressive price that nobody would sign on for, but apparently we were underpriced. Yash Gad, founder and CEO, Ringer Sciences. We're not betting on people paying more for energy. We're betting on people paying less. The hardest part of our work is finding the center of the concentric circles, what makes economic sense today and also makes the world less emissions intensive. Partner, Active Impact Investments. If you sell an $8 bag of frozen empanadas online, you're probably paying $50 for packaging and shipping. It's prohibitive. Founder and CEO, Latin Goodness Foods, Maspanadas. $25 and a family that talked money. Rocky Lalvani is 2 years old when his parents arrive in America with $25 in their pocket. They do not live in the good part of town. But he notices something. When his parents get together with friends who also immigrated, they talk about money. How things happened, how they were getting started, how they were building success. I just assumed everybody had money conversations. Much later, he realizes most people do not, and that this taboo is why so many people, And so many business owners struggle with money. As a kid, he also sees one side of the family with a lot of money and decides he wants to be rich like them, so he hustles and figures out how to make a buck. Within a single generation, he says, he has the American Dream lifestyle, on his own terms. That story is from... We didn't raise money. The 3 of us each made significant sacrifices. I rolled my house down payment savings into the business. My cofounder put his wedding funds in, our CTO in Norway returned his brand-new Tesla for a refund and put all that money into Paladin. James Creech, founder, Quartermast Advisors. When we went profitable, there was this weight that was lifted, and you realize you're now masters of your own fate. It lets you ask, what do I want to do? Not, what do I need to do to get to the next round? Tomasz O'Farrell, co-founder, Workana. The system is designed to allow these extraordinary, extravagant billionaires— because most people are going to fail, And we want people to try. We want our smartphones and electric cars and the internet and search engines. All the benefits we have are there because of the entrepreneurs and capitalists. Founding publisher, Skeptic Magazine. I will be relieved when I've returned some money from my Fund 1 to my first investors. Then I will start calling this success. Before that, it's not success, but there are some nice rewarding steps in between. Olivier Tonneau, founder and partner, Quantination. What is a human life worth? Not what you earned. Avi Yashchin, who runs subconscious.ai, wants to measure what money cannot. He starts with a number used in healthcare, insurance, and government policy: the value of a statistical life. In the United States, it is about $14 million. Then he does the math on the average American: $50,000 a year for 40 years, Roughly $2 million of lifetime income. The gap between the 2 figures, he says, is all of these intangibles, these non-market goods, these externalities: social connection, mental health, liberty, happiness. Nobody sells them, so markets cannot price them. His conclusion is unusual for a founder. If anything, governments should be bigger because markets alone will not deliver human flourishing. His company is building a scale to measure what people value where no market exists. That story is from Writing Checks. I realized I'm not a professional investor like Marc Andreessen, not even close. So I invest in knuckleheads that are like myself, and that's not the best way to run your investment portfolio. I learned that the hard way by losing my money. Jim Weldon, Chief Executive Officer, Prospect Desk. We have a thousand-year business plan. If you set up a church to withstand the long term, you have to think generationally about how finances pass from generation to generation and what technology will do throughout that. Amber Meixle, founder, Suivera. On average, about 25 people come to these events and I charge $60 a person. I'm making about $1,500 in about 90 minutes. I copy and paste this model all over the region and now I'm making 5 figures a month. Founder, SoundQuest. You could be the most talented actor in the world and still only work once or twice a year. If you want to be an artist in New York City, you have to figure out how else you're going to sustain your life. Co-founder, The Inheritance Project. After 9/11, a Wall Street trader walked away and sold bulls. Andrew Pudiloff is global head of derivative trading in New York, making bets for the bank. Then September 11 hits. His wife, who had also been in the tower during the 1993 bombing, is back from maternity leave that very morning and watches the plane crash in. A close friend jumps. I'm done. He moves his 2 children to Boulder, Colorado, and decides to build something he has no experience in: a healthier kind of quick-service food. In 2004, he launches the first real bowl store in the country. Serving acai bowls to customers who do not know what an acai bowl is. He does not franchise until 2017, and today he owns the company outright. That story is from. We take the industry standard commission of 10 to 15%. The difference is we're direct to the access point. I like to say we're one or two phone calls away from pretty much everybody. There aren't ten layers between us and the talent. Lee Barcalo, CEO and co-founder. Current group. In the healthcare system we built, hospitals make money when you're sick, doctors make money when you're sick, the food business makes money feeding us cheap and less healthy. The only entity that doesn't make money when you're sick is the payer. Joseph Antoun, Chairman and CEO, L-Nutra. I tell every person I work with, we can get you into Harvard, but if you don't have a way to generate income from your skills, this is the worst economy to be in. We're all learning you can't rely on corporations, no matter how well you perform or what your resume looks like. Anthony Berryhill, owner and founder, Elite College Hackers. I have 26 clients over 10 time zones. In my hour a day, I'm talking to clients about 20 minutes. If one sends me a 5-minute message, I listen at 3x speed and get back with a 2-minute answer. I've kind of figured out a way of bending time. Founder and business coach, Less Doing. The blockchain founder no crypto name will platform. Greg Chu has been trying to bring about what he calls the economic emancipation of humanity since 2002, back when he was a trader. His claim today is blunt: most of what is called blockchain is fake, with hidden control functions. He says he has been no-platformed in every direction by the big crypto names because he keeps calling them out for pump-and-dump schemes. So his team builds a proof-of-work chain, taking the ideas from the Bitcoin whitepaper and making them tens of thousands of times more efficient. They patent everything, then license it free under GPL-3, simply so nobody else can patent it and block them. He is not selling a service. He says anyone can use the open chain, and the hard part is that freedom comes with responsibility. That story is from— by transitioning to EVs, the average driver doing about 200 kilometers a day would save about 5.3 metric tons of carbon emissions every year. Trade that on the carbon credits market, and a driver could make an extra $100 to $250. Adetayo Bamiduro, co-founder and CEO, Max. A studio creates an LLC specifically for a movie, then tells the writers, directors, investors, and actors they'll see a percentage of the profits. Then the studio throws every expense under the sun into that LLC to make it look as if the movie didn't make money. Sharif Bennett, co-founder and chief evangelist officer, Cineblock. In a distributed workforce services business, up to 30% of what they spend in direct labor costs is attributable to the poor quality of their culture. If they perfectly solved for culture, they could reduce labor expense by 30% without cutting a single head. Brian Hughes, principal, author of Toxicity: Clear Day Strategies. We stopped selling instruments here about 10 years ago. It's just not worth it, because you go on Amazon and get the same thing for 30% less. Daniel Powers Jr., founder, Real Brave. A casino IPO at $4.55 and a $28 light bulb. Robert Stevens is a stockbroker in the 1980s selling bond funds when gaming becomes legal in Colorado. A local company called Blackhawk Casino and Gaming needs money, and he puts together a private financing round. It is priced at around $4.55 a share. By the time the round closes and investors get their securities, the stock is at $28 or $29. Everyone who got in gets right back out with monumental returns. Robert has what he calls an immediate lightbulb moment. Why not focus the entire business on that? A private company needs money, and you either make exponential returns or lose your money. From that day on, the idea of taking 10 grand out of some old lady to buy a bond fund is gone for good. Years later, a client asks him to serve as a receiver. His response is, what's a receiver? That story is from— If I wanted a forecast before, I'd go to a professional consultant and pay hundreds of dollars an hour for a report. Now I could just pay like a dollar and get something a little bit similar. Founder, advisor, author, Vico. We don't do allowances in our house. I have a ledger of chores. Cut the grass is $5. Take out the trash is $3. Then there's a catch. Since you live under my roof, you pay rent, 10% of everything you make, another 10% in taxes because I'm feeding you, and 10% into savings. Jeff Barnes, CEO, Angel Investors Network. When is anybody given any credit bureau authority to create a credit score on you? Never. It's imposed on you, buried in every agreement you sign for a cell phone, an apartment, A car. And you don't have one score. You have one per product, so north of 70. Founder and CEO, My Home Pathway. We had sound money for millennia, and now we're living in the briefest financial experiment in human history since we only run on fiat. I was born in 1990, so I had to go back to history and realize sound money was the norm. COO and co-founder, Dial. A 17-year-old, a cigarette, and a 7 a.m. start. It is the 1,990 seconds, and one 7-year-old Ari Baum has a summer to fill. His father refuses to let him be a beach bum. Ari has noticed stockbrokers in suspenders, driving Porsches, and decides they must be doing something right. His father calls a friend at 17 Battery Place, a few blocks from the American Stock Exchange, The interview is a 30-minute grilling on interest rates, the Fed, and stocks, and Ari knows nothing. Then the interviewer lights a cigarette in the office and grins. I'm just messing with you, kid. Come in Monday at 7 AM. Ari walks 2 blocks before it sinks in. The brokers take him under their wing, and he stays through high school, college, and beyond. That story is from Zine Alone Is Half of PMI's Operating Profit. And this is the business that sold cigarettes for 100 years. Half their operating profit goes to show the extraordinary margins built into the product. Jason Sherman, co-founder and managing partner, Top Shelf Ventures. What's wrong with $1 million a year in revenue netting a couple hundred grand? What's wrong with $5 million in revenue netting a million? That's how you become wealthy. Do that for 10 years and it's a huge amount of wealth. Greg Shove, CEO, Section. Our moonshot is the best case. Then we write down the worst case, all the things that could blow us up, and then the most likely. The worst case is not losing everything. And at the end of the day, it's all about cash. So forecast cash first. Shannon Burns Susko, 2x exited CEO, founder, Metronomics. When you're poor, you're constrained so your excesses don't become abuses. Then when you become rich, if you aren't constrained by your own morality or your own rules, excesses turn into things that are unhealthy. Founder and CEO, Advinal Medical. The billion-dollar company losing $72 million. Doug C. Brown walks into a company doing over a billion dollars a year and asks to see the numbers. They answer with revenue. He asks again. They say it again. They are a billion-dollar company. By the third time he has heard it, he changes the question. How much money are you losing? The answer is $72 million a year. For Brown, that is the whole lesson. Leaders brag about revenue because it is sexy, while margin sits unexamined. He started working at age 3 in his father's industrial machinery repair shop, sweeping floors. Now, on his 38th venture, he finds hidden margin for founder companies. A quick 15-minute diagnostic once turned up $229,000 in EBITDA sitting there, That story is from— someone seeking to maximize profit will invest in the assets their business needs to be successful. They'll pay their rent and their staff. If we are not also investing in a healthy planet, it's a huge miss because there is no future economy if we don't have a planet that can support life. Kate Williams, CEO, 1% for the Planet. We got $24,000 for the book split between the two of us, and then there were agent fees and taxes. We were both living on credit cards. We both bought apartments, but primarily we spent all of our money on therapy. Nicola Kraus, founder, bestselling author, and book coach, The Finish Thought. My parents had co-signed a bank loan, and after my first semester, they went bankrupt. I was a year into school with about 15 grand worth of debt and needed to figure something out. Jesse Hopps, founder and CEO, Demand Metric S Commercial Excellence Consortium. People assume when you buy a million-dollar business, you need a million dollars in cash on the table. That's almost never how it works. In service businesses, it's rarely more than 50% down, and the rest can be a seller's note, an earnout, or a contingency plan. Carl Hughes, owner and CEO, The Podcast Consultant, Rise25, Draft.dev. The cost of building a data center with this technology is about $6 million per megawatt instead of $13 million. Maintenance cost is reduced by 90%, and energy cost by at least 40%. Herb Zien, Vice Chairman, Liquid Cool Solutions. We found a niche of finding penny stock companies and rebranding them. When we rebranded them, their stocks would jump from 5 cents to a dollar a share. That division was netting a million dollars a year plus. Gene McCubbin, President, Pop Labs. We have never raised money from anybody, and today the company is completely debt-free. We are opening seven new international offices this year, and we have clients in about 48 countries. Yele Okereemi, CEO, Precise Financial Systems. Chapter four: Raising VCs, Angels, Bootstrapping. The pitch that worked and the ones that didn't. Everyone thinks entrepreneurs are always chasing money. But the hardest part is the talent. High-quality talent is attracted to other high-quality talent. Money chases talent, not the other way around. CEO, Nine Zero. He took his company public, then took it private. Ben Narasin starts FashionMall.com in New York City in 1993. He bootstraps it all the way to the underwriter's letter, takes it public in 1999, then takes it private again in 2001. He has liquidity, and he retires for a while. Then he moves to California about 22 years ago and spots a gap between angel and venture, so he starts one of the first two institutional seed funds. His plan is to find a failed company he can take over and run. Instead, he realizes something else: it is better to live vicariously through many founders than to be a single founder. Two decades later, he runs Tenacity Venture Capital, with seven portfolio companies public, a first-round check in Rippling, and a fund named for the one. Trait he demands: tenacity. That story is from Databricks is valued at around $80 billion, and they don't even own the core IP. Anyscale raised $100 million at a billion-dollar valuation, and again, they don't own the underlying library. It blows my mind. Dan Desjardins, CEO and founder, Distributive. A mother begs a pilot to show her kids the world. Lou Cooper is 12, growing up in the Paquanok projects of Bridgeport, Connecticut, With a father in prison and no real connective tissue to the outside world, his mother does something bold. She goes to a local airport and begs a pilot, We live in the projects. Can you just show us the world? The pilot says, Sure, next Saturday. He takes Luke, his sister, and his mother up in a tiny Cessna. For the first time, Luke disconnects the projects from everything else. Oh, okay. There's a whole world and I'm not trapped here, he thinks. That same year, he joins a program teaching entrepreneurship and builds solar-powered microwaves. He later graduates law school at 23 or 24, builds two companies, and exits both to Fortune 300 buyers. That story is from money raising is the biggest time suck ever and very stressful. Most of the time you get nos. Now, anytime we hire a person, we ask, "Can we do this with AI?" We can build a huge business with eight people. Sahin Boydas, co-founder and CEO, Klaros Farm. The hedge fund data chief who bet small and won big. Matt Ober spends years in hedge funds, first running data strategy at WorldQuant, then as chief data scientist at Third Point. At WorldQuant, the thesis is simple: consume more data than anyone in the world, manage more money. He leaves for venture and joins Social Leverage, a seed-stage firm that writes $1 to $2 million checks. Its early bets include Robinhood, eToro, and Alpaca. He picks up one more by accident. The founder of Manscaped, local to where they live, had pitched them other ideas, and the grooming company started as his side project. For Matt, the lesson is that early on, you back people because you never know what's going to happen. Social Leverage's last fund was $85 million, and he likes it that way. That story is from I Assume I'm an Average Investor. I assume I have average deal flow. I assume I'm an average picker. Everybody thinks they're above average, but I think they're all kind of fooled by randomness. So what do you do if you assume you're average? You play the odds. Founder and managing partner, Team Ignite Ventures. She raised $50 million by accident and earned nothing. Brandy Koloski runs a branding agency, and one of her clients is Formula 1 electric racing. Their CMO and CFO tell her, "If you find an investor, let us know." She has never worked in that world. Then, at an Art Basel event for Stephen Tyler's daughters, her gut tells her to approach a table of gentlemen. One of them is the CEO and license holder of Gulf Oil of Mexico. Two weeks later, he invests fifty dollars million. Her cut is nothing. She had no prior agreement, and paying her would have been illegal anyway since she was not a broker dealer. I didn't get a dollar out of the deal. Didn't know how to protect myself. She keeps going. She later helps raise, deploy, and manage around $400 million, then starts her own fund, Sacral Capital. That story is from founders from Gen Z are telling me they don't want a check from Sequoia. They saw me online and they want me on their side. It's going to be less about the brand and more about individual influencer VCs. Itamar Novik, founder and general partner. Recursive Ventures. Hundreds of rejections before the headline round. On Crunchbase, Peter Fishman's fundraising looks tidy: $125K, then $4 million in 2020, then $15 million in 2022. Up and to the right. The real story is messier. Fishman, a former data analyst from Zenefits, Opendoor, and Yammer, runs Mozart Data through the first fully remote Y Combinator batch. During the pandemic, with a co-founder he has never met in person. He sets a hard deadline: raise by Demo Day or go a different direction. Investors see through fluff, he says. And they say no. A lot. I have hundreds, he says, comparing himself to Airbnb's Brian Chesky and his 6 famous rejection emails. Hundreds of rejections on the seed, and over 100 on the Series A. The cliché story? he says, is no bumps in the road. That story is from: We applied to YC many, many times. Between my co-founder and I, it was 7 times. We got in on the 7th time. It massively exceeded expectations. Founder, Hyperspell. 9 years, 3 people, and almost no pay. Mark Michael raises a couple million dollars for DevHub in 2009. He and his co-founder, partners since they were 17, hire too fast and expand the office, convinced they have product-market fit. It's an illusion, he says, when money is in the bank. By July 2010, they are more or less out of money. They lay everyone off in one day, leaving 3 people. For about 9 years, they pay themselves almost nothing and put every dollar back into the company. Then the pandemic hits just as they thought they had arrived, and it teaches them that no brand will ever shut off 2,000 websites. DevHub goes on to acquire a platform of retail brands on May 4th, 2021, and now launches over 265 brands. That story is from Canada has 170,000 families worth $7.5 million or more. International wealth standards say 5% should go into early-stage venture. We estimate only about 0.05% of Canadian wealth is currently invested there. Jesse Wiebe, founder, Canadian Startup Capital Association. The startup the VC was sure would fail. Viktor Orlovsky runs a venture firm out of Menlo Park after a career as a software engineer and CTO at 2 of the largest banks in Uzbekistan. He remembers 2017, when his team reviews the whole portfolio and spots a few outsiders. They expect those companies to run out of funding and plan to either lose them or sell them. One of them, the one they were sure would fail, turns around and becomes one of the best startups in the fund. He says that is common in this business. His takeaway is blunt: I do not assess founders really well. Many of his failures, he admits, trace back to his own mistake of betting a team could handle a harder situation than they could. That story is from We had a venture capital deal to sign on October 21st. 1987 for a million dollars to expand our business, and October 19th was when the stock market crashed. Of course, everything changed, and the venture capital deal didn't happen. Ronald M. Bazaar, CEO and co-founder, Tasty Picks International. The woman who sent Tesla to China then built a seed fund. Veronica Breckenridge is a mathematician and industrial engineer who spends eight years at Apple Asia. Scaling her business from single-digit millions to over a billion. Then Tesla calls. She meets Elon Musk, who wants to launch in China. She builds the team from fewer than 10 people to 500 employees in 7 cities with 10 stores. In 2015, a Chinese private equity group asks her to break into Silicon Valley with only $200 million. Traditional venture will never win deal flow, she decides. She meets Naval Ravikant at AngelList and pitches an institutional pool that writes the checks syndicate leads struggle to fill. The result is a $100 million seed fund, 300 companies, and nearly 40 unicorns. As she puts it, it wasn't the volume of deal flow; it was really the quality. That story is from Anaconda started as a bootstrapped company. People were pushing the Hadoop ecosystem, which was what Google had thrown out. But they took money and amplified that message. That was the first time I realized, very fundamentally, that money buys influence. Travis Oliphant, CEO, founder, head of OSS, Platform, Quantsight, Zyphra, raising $1 million from detention at 17. Robert Harary is 17, sitting in detention, when he falls in love with a company. He is not an inventor, but he thinks he might be good at raising money. So he asks the founder for a little allocation, then raises just under a million dollars from different investors and deploys it. The round closes when he is 18. His father, a lawyer who worked his way up to CEO of a public tech company, had already given him the rule: No one gives a damn who you are; they care about the deal that you're investing in. Find good deals, route them to the right investors. Eleven years later, Venture has four times as many deals. Founders and VCs. The rule has not changed. Robert, now 28, has built his career on recreating that magic. How does a deal get done outside of your network? That story is from— The chance of being successful when you've only got $10,000, $20,000, $50,000 of friends and family money is about 1 in 1,000. With real seed capital, it's 1 in 100. With real venture capital, it's 1 in 10. Kevin Suresh, futurist, keynote speaker, inventor. The founder who burned the boats for AI agents? A couple of years ago, one of Duncan Davidson's portfolio companies has a really good software product. Then the founder sees what AI agents can do and makes a call. He burned the boats as Cortés did in Mexico. He goes all in on agents. It takes years. ChatGPT does not figure it out for him. He has to learn how humans actually work in his market, Then string the agents together so they match or improve the real workflow. If it works, he ends up with a 2-sided marketplace and a long-term moat. Davidson says that is exactly what Bullpen now hunts for. Not wrappers on top of big models, and not $100 to $1 million valuations for a PowerPoint, but real workflows. Real revenue and metrics that prove demand before anyone else believes. That story is from Vibe investing is dead for some time. Just raising because you have a good story and a good vision and you're cool is going to be tricky. A seed today could have been a pre-seed in 2021. Stefan Nasser, co-founder, OpenVC. A $2 billion round that never hit the bank? Prashant Mahajan is deep into a fintech called Owa in West Africa, with about 40 people on payroll. Then a VC opens the door to a raise. We were supposedly in the process of raising $700 million, he says, a round that would value the company at $2 billion. Due diligence happens. The team assumes the wire will land within a month, so he raises salaries and makes big commitments to his people. The money never comes. Overnight he cannot pay salaries or dues. Years later he learns why: the people who were supposed to wire it were fraudsters running a Ponzi scheme, and the U.S. government eventually charged and arrested They had even taken significant money from his side to cover diligence costs. The company goes bankrupt. At that time, I was crying under my pillow. That story is from— Most gaming studios are founded by ex-something. The next Ubisoft, the next EA, ex-Riot Games. But we were ex-nothing. So we often have to remind people we know our jobs. Founder, Kiro'o Games. The $5M a year seller who gave up the cash. For 10 years at LeadMD, Josh Wagner sells to and through partners in the Marketo ecosystem and personally brings in over $5 million in revenue every single year. Then he co-founds a venture firm. Suddenly the money is not coming in day over day because it is invested for the long term. Josh admits the shift added a level of stress to my life that I'm not necessarily used to. At home, he has to reset expectations because it is not just rolling in like it was when I was just knocking down deals all the time. His verdict on the trade: a long way from a closed deal, a life transition, but all for the good. That story is from I Try to Ignore Investors. I think they can subtract more value than they add a lot of the time. A good investor should get out of the founder's way. They should push, support, and make intros, but doing things because an investor expects it is often bad. Max Marcioni, co-founder, Superpower. The utility man who quit to chase Bitcoin. Bryce Gilliland grew up wanting to be CEO of an electric and gas utility, the way his parents' world worked. He spent 8 years climbing it before the math hit him: a 35 or 40-year trek, and no real power to change anything. At Berkeley's MBA program, classmates were building much cooler things. A buddy was great at trading, and Gilliland had made some money in Bitcoin, Comfortable, not Bitcoin rich. So he quit, traveled the world, dropped out for a semester, and returned to start a hedge fund. Today he is a GP at California Innovation Fund 2, writing $250,000 to $500,000 checks into UC startups. You gotta go outside and really take control of your life. That story is from— We are making technology for venture funds. If we had one or two big investors, people would think we were biased. By having angel money and public funding, we keep our independence, and that helps us in the market. Penny Schiffer, CEO and co-founder, Raise.ai. He couldn't find one reason to say yes, so he did. 7 years ago, a limited partner tells John Frankel to meet a founder with a crazy idea. 40 minutes in, they are deep into last-mile drone delivery, and John has a list of doubts. Will the drones fall out of the sky? Will consumers adopt? Will regulators approve? The founder pushes back. You said you had one problem. My problem is, I think you are uniquely positioned to solve this. 6 months later, leads the seed round of Mana. The founder has never built a drone, but he is a serial entrepreneur in Dublin, small enough that the regulator is up the road. During COVID he gets a license to deliver medicines. Today, Mana has made hundreds of thousands of deliveries, is profitable, and cuts delivery from 28 minutes to under 3. That story is from We signed a term sheet and were going to close a €12 million investment in March of 2020. It got pulled away in mid-March. We rallied our shareholders, sold them an opportunity they could believe in, and raised a convertible note. David Gunnarsson, CEO. Dohop. The heat pump pitch that sounded boring and wasn't. A team pitches Mike Winterfield's climate fund on vertically integrated heat pump installation. It does not sound interesting to him. As he puts it, not only is it hard to do software, it's even harder to do hardware, and it's equally hard to do services. And these founders plan to do all three. Their bet is that software, hardware, and services can talk to each other, make each other more efficient, and build a moat against every competitor who owns only one slice of the chain. Mike's fund invests when they are pre-revenue and have not sold a thing. Within 6 months of starting operations, the company, Jetson, passes $10 million in revenue. After 7 years of investing, he says, that breaks a record. And customers are not buying because they love the planet. It is simply the better, cheaper product. That story is from: I was getting in the car to meet with a venture capitalist, and I said to my girlfriend, now my wife, there's a little part of me that hopes that he doesn't invest in us. Because then I feel like the game would be over, and this is the part that I love the most. Charles Gaudet, CEO, Predictable Profits. 190 Meetings for a $650,000 Round. Mario Martinez Jr. rolled up 7 companies into Vengreso, the biggest digital sales prospecting trainer, and thought merging them was the hardest Hardest thing he would ever do. Then he turned the company into a SaaS business and went to raise money in a downturn. He and his co-founder, both LinkedIn influencers, ran a crowdfunding campaign and signed about 150 small investors from $100 to $50,000. Their new investors put Vengreso on their profiles, which sparked more attention. A VC finally led the pre-seed, but it took 190 meetings to raise $650,000. Other founders told him, "If you're not doing 300 meetings, you're not doing enough." He was within the norm. That story is from between 2021 and now, in climate especially, people raised too much money at too high valuations and then didn't operate effectively. They had to close down, raise down rounds, or recap. Our operators grew into those peak market valuations. Sam Hasty, partner, Active Impact Investments. The phone call that checks if the driver is okay. On the roads of Nigerian cities, a delivery rider can cover 200 kilometers a day on a motorbike. Adetayo Bamiduro's company, Max, rents electric bikes to those gig drivers, and every vehicle is wired with sensors. The system tracks speed, acceleration, and deceleration, which together are a significant predictor of whether an accident is about to happen. An automated alert goes to the driver first, then a human steps in. Max employs what it calls driver welfare agents who pick up the phone and ask how the rider is doing, saying the signals from the last trip suggest they may not be in the best state of mind. Every driver also gets a DOT-certified helmet plus life, accident, and disability insurance, so a crash does not mean zero income. That story is from— Michael gave us funding for about 6 or 7 months, Unfortunately, he passed away from cancer in July. We've had a pretty big hole in our hearts, and also in some of our leadership. Ryan O'Hara, founder and CEO, Pitchfire. A dad charges his sons rent, taxes, and savings. Jeff Barnes grew up in Los Angeles, was homeless at one point, then ran a nuclear power plant on a submarine. Now he lives in a nice neighborhood with 2 boys, 11 and 12, and he worries they are too comfortable. So he skips the allowance and builds a ledger. Cut the grass, $5. Take out the trash, $3. Clean the bathrooms, do the laundry. Want to play Xbox, sleep over at a friend's, or go bowling? That costs money too. Then the catch. Since you live under my roof, you have to pay rent. 10% of everything they earn. Another 10% goes to taxes, because he is feeding them. The last 10% goes into savings, an idea from the richest man in Babylon. He cannot teach principles at seven, he says, but he can plant habits. That story is from when we raised VC money to make our own game. We completely scaled down third-party work. When the first-party game didn't work out, we basically had no revenue and were a few months from dying. I'm never going to stop third-party development again. Zisombor Pirok, co-founder and CEO, Space Rock Games. The founder who pivoted his company on February first. Greg Shove has spent over 30 years in Silicon Valley with some strikeouts, some wins, and no unicorns. By his count, he has sold companies for a combined $250 million. His kids are unimpressed. In early 2023, his venture-backed online business school section is not growing. There is no real moat in online education. Then he plays with ChatGPT Plus. Okay, this is the new accelerant for careers. On February 1st, 2023, he pivots the whole company to teaching AI and later to helping enterprises deploy it to teams of 1,000 to 100,000 people. The next target: a $100 million business riding the AI wave. His advice for everyone else is blunt: do not take VC money unless you really need it. That story is from We Ended Up Raising Way More Money Than We Needed. The effect that raising too much money can have on a company really changed our company culture. That's something I've tried not to do at Workana, and to be a bit more frugal and lean. Co-founder, Workana. The biggest pain of being an early-stage investor is that you're going to get diluted to death and end up making other people a lot more money than yourself. So we said we're going to keep 100% reserves, offense and defense. Managing Director, Ocean Azul Partners. What we promise our investors is that we will apply a very thorough process. This process can fail for any number of reasons, or it can succeed for any reason we did not anticipate. We have to do the job right. Olivier Tonneau, founder and partner, Quantination. I think the capital has perverted the grit and entrepreneurial zeal that you should have in a startup, which is, how do I get a lot done with a little? Not, how do I piss away $20 million on an A round? Jim Weldon, chief executive officer, Prospect Desk. As a woman founder, I had to bootstrap for years. The venture capital culture only started around 2018 or 2019, but I started in 2010 or 2011. To sustain until then, you need that guts, that power. Founder and CEO, Space Kids India. If you raise a ton of money, the temptation is to build a company with all these different people and functions, And you have to justify margins. In the end, it's not about how big your exit is, it's about how high your margins are. CEO and co-founder, Toolhouse. If you're sitting on a large sum of capital and you feel the pressure to deploy it, you will start to make irresponsible choices just to put that money to work. So we drew a hard line and capitalized Synthesis at $75 million. Founder and managing partner, Synthesis Ventures. My slides for pitch decks used to be horrible. It was just graph, graph, graph, graph. There was no flashy takeaway or arrows to what you should be looking for. Nina Horowitz, CEO, ImmuneBridge. The big funds said, no, there's not a market here. This is stupid. Then once a 16Z decided the creator economy was a thing, every investor wanted in. If I sound like I have a chip on my shoulder, It's because I do. They acted like they invented it. Executive coach and writer, Good Work, former COO of ConvertKit. You don't throw your money so much at your first assumptions when you don't take VC capital because you have to make everything work. You have to have proof of concept first. Investors started asking for profitability after Silicon Valley Bank failed, which they should have done from the get-go. CEO and co-founder, We ran a study of 70 different celebrity-backed tequilas launched in a 3-year period. 65 of those either don't exist or barely exist. They all raised a lot of capital during a low-interest environment. Co-founder and managing partner, Top Shelf Ventures. We've never sent out a press release. I did a TED Talk, and Google called and put us on their homepage. The narrative kind of took on a life of its own. SoftBank wasn't supposed to be an investment. It was just an accelerator, and by the end they offered us one. Dal Levant, founder and CEO, AquaGenuity. Chapter 5: Selling. Cold email, founder-led sales, the first customers, the deals that changed everything. I practiced the first cold call for 4 hours. As soon as the person picked up the phone, I hung up, and everyone was laughing at me. But I didn't stop. I did the next one and the next one, and I got better and better. Lloyd Lobo, co-founder and author, boasts, AI and traction. I have failed miserably at sales. I'm a good visionary and I can do the big showcase first meeting, but that is very different from doing sales for the next 12 touchpoints. So I'm hiring a salesperson, giving them up to 10 to 15% of my company, and they'll become CEO if they succeed. Juan Luis Betancourt, CEO, Humantelligence. The 3x liquidation preference that aided his exit. Philip Ogilvy is an unemployed roofer from Springfield, Ohio, with a mortgage and a book on how to roof a house. He builds software with his teenage son, sells a copy to a roofing buddy for $5,000, and eventually launches iSqueft, which brings digital blueprints to commercial construction. It is the end of the dot-com boom, and investors are skeptical. His angel keeps payroll alive with a $100,000 check hung on his office door. The first term sheet carries a 3x liquidation preference. I was certainly naive, he says, and there was an aspect of desperation. When the company sells for about $85 million, the investors take their money 3 times over first. He and his son get pennies on the dollar. So they start Stack, which now passes $30 million in recurring revenue, That story is from— we hoped for 100 or 150 people to show up to the first event. We got 660 that year, 1,000 the next, 1,700 the next, and ultimately 4,000 people came to Cleveland, Ohio. That one event brought in about $6 to $6.5 million in revenue. Joe Pulizzi, founder, author, The Tilt, Content Entrepreneur Expo, founded Content Marketing Institute. We aired on Shark Tank in February 2013 and did 10% of our lifetime sales in the week after. We pulled random people off the street to help us pack. Stephen fell asleep standing up at his desk. Co-founder, Xero Shoes. A Sunday Night Call That Ended an Agency. It is late on a Sunday night when Luke Vanderveer's phone rings and wakes him. A client is on the line, complaining about his business. The absurd part is that the client was getting a crazy number of calls. Before Luke met him, he got nothing. Now he is buried in leads and griping about it. Luke has had enough. I fired him on the spot. Then he shuts down his entire SEO agency. Instead of working for clients, he builds websites in the niches he already knows, keeps every lead himself, and rents the properties to local business owners like a landlord. No reporting. No client requests. Seven years and hundreds of sites later, he coaches others to do the same and recently bought an ice cream truck business with around fifty trucks. That story is from. You're not competing with other marketing. TV commercials compete with the TV show, not with other commercials. On LinkedIn, you're competing with people posting. Look what I did. That means you need to act that way. Justin Oberman, founder, Oberman and Partners. Someone told me you have to be either the best in the world at what you do or the only one doing it, because if you're the only one, you're by definition the best in the world. Jay Samit, serial disruptor, author, keynote speaker, jaysamit.com. The headhunter who fills a racetrack with Ferraris. Roger Douguet is a managing partner at Boyden, a firm that places roughly 1,000 CEOs a year worldwide. His problem? Every law firm and bank already invites CEOs to the Grand Prix or a golf day, So he thinks differently. Boyden books the Mont-Tremblant racetrack for one full day, invites 60 CEOs, and puts 25 Ferraris on it. The power of that is not about the money, he says, because these people are millionaires and billionaires who can buy anything, but they cannot get the track owner on the phone. His real job, he says, is to hold the cell phones of Quebec's top 500 CEOs because the math says someone always quits. And when they do, he is the first call. That story is from. One thing about motor racing is having almost no shame in going out and asking for the deal, going out and asking for sponsors. When you're selling a product, it's quite easy after you've spent years trying to sell yourself as the product. Cameron Van Den Dungen, CEO, former racing driver. Sleep tight. Every author is a little insecure when they're about to launch a book. My podcast features an author every episode, and the reason they choose to work with me is that I'm helping them sell a book. They're about to launch. That's the cheat code. Nick Hutchison, CEO and founder, BookThinkers. A client pays $50,000 a month and still makes him miserable. At a high-level event, Shawn Clarke watches an agency owner interrupt a conversation to take a call. The client pays him $50,000 a month, but he says, you're a pain in the butt. Clarke asks how much he actually keeps. Not much, comes the answer, because he is killing myself with a 5-person team. Clark tells him to move to software, selling the same service as a $300-a-month platform. 6 months later, the guy reaches out. He has 100 SaaS clients, ditched the difficult client, and nobody ever calls him. It is simple, he says, and scalable. For Clark, it proves the point behind HighLevel: bespoke service does not scale, and agencies need a business model, not another tool. That story is from We sold the old product to the person that it was going to replace, and naturally they said, we don't want that. This time we learned. We target higher up in the chain. CTO and co-founder, Contour YCS '23. Sometimes you have to get up at 5 in the morning and go to a construction site in rural Indiana. A lot of people don't want to do that. If you're selling SaaS, you can sell it from behind your desktop. That drives trust, and it keeps out people who aren't serious. Arvind Veluvalli, CEO and co-founder, Fresco YCF24, a podcast legend, tells his host, I was overwhelmed. Andrew Warner has interviewed more than 2,000 entrepreneurs, and now he is the one in the hot seat on a Zoom call with a host who builds everything at once. The host's screen reads 43X founder, 21,000 meetings, 3,000 campaigns, 3 Iron Mans. Andrew says it out loud. He came hoping to learn a process, maybe podcast production, maybe SDR services. Then it was one thing after another. I think I'm overwhelmed. His mind drifted to what else was on his own computer. He cannot picture what to remember this man for. Elon Musk, he points out, was not chasing 500 things at once. Andrew's advice is blunt: pick the one thing, do it really well, and let the screen go quiet. That story is from a friend of mine built a brand and sold it for eleven million. I asked him, "Could you do it again?" He said, "Absolutely not. You can't just throw money at Facebook ads or SEO these days and expect a brand to take off. The old ways are dying really fast." Benjamin Stern, founder, Teal Fellow, Tankara, Nobo. We started with three great customers: Cisco, Hewlett Packard. And Chrysler Motors, the loans division. We got 25 customers in one year, raised $13 million, and sold the company to a publicly traded company. Anushukla, co-founder and executive chairman, Botco.ai. The Interrogator Who Never Knew Where Saddam Was. In 2003, Eric Maddox joins a Delta Force team in Tikrit with one job: find the most wanted man in the world. Nobody knows where Saddam is. The military guesses Syria or Baghdad. Erik decides to assume nothing. He starts talking to prisoners, hundreds of them, and notices the fighters are loyal but the facilitators who supply safe houses and cars are not. Their hearts aren't in it. They want out. One trail narrows to a single bodyguard. On December 1st, they capture the bodyguard's driver, who spills 5 safe houses. 2,000 names shrink to 10. 13 days later, Saddam is pulled from a hole. Eric is modest about it. I didn't find Saddam. These prisoners took me. That story is from... I didn't sign my first client for, like, 8 months. I was working like an animal. Literally 12-hour days with nothing in return. People smell the youth, they smell the incompetence on you at the beginning. I had no feedback loops. Founder, NSY. With almost 2,000 interviews, we have never paid for a speaker. Speakers pay us because they want to be in front of the ideal audience. Eric Yang, founder, Lead Next Gen, SaaS Growth Summit. Fired at 28, he gave himself 90 days. Chris Walker plans to own a company by 35. At 28, that plan arrives early. He is working at a company where he and the CEO do not see eye to eye. And the CEO asks him to resign. On the way out, the CEO looks him in the eyes and says he would make a great consultant. Chris does not believe it. He has no confidence he can do it, but he gives himself a deadline. I'll give it 90 days. 90 days later, he is making more money than he did in his job with happy customers. He realizes he can earn income without a paycheck from somebody else. Years later, in 2019. He starts Refine Labs alone in his living room. Today, it has worked with over 250 high-growth B2B SaaS companies. His lesson: You are never going to feel ready, but you are. That story is from Selling Science to Scientists Is Nearly Impossible. Selling science to investors is very unprofitable. A founder is going to listen to a funder rather than another founder. Nick Goldner, CEO, Stealth Fintech Startup, formerly Resistance Bio. One of the big missteps the industry has taken is trying to find the biggest database possible, thinking the more patients at the top of the funnel, the more enrollees at the bottom. Medicine doesn't work like that. It's not a sales funnel. It's relationship-based. Scott Stout, CEO and co-founder, Medvector. From $6,000 deals to $200,000 deals in 3 years. Anis Benyasser is a second-time founder running Attention out of New York with about 16 employees. The company starts where many startups do, selling to micro SMBs and early stage startups at six thousand dollars per client a year. Then he does the math on velocity: a one hundred thousand dollars deal that takes a hundred days is one thousand dollars a day. Enterprise deals bring in four to six thousand dollars of selling per day, while SMB sits below one thousand. So the company keeps climbing up market. The first six figure logo takes about a year. It introduces the next six figure logo. Which introduces another, because enterprise people move to other enterprises and bring vendors with them. 3 years in, average contracts reach $200,000, and he is hiring account executives to close what he used to close himself. That story is from— in this space, you can't show up and say, hey, our model does XYZ. It has to be grounded in peer-reviewed research. And a lot comes from warm relationships. Because for the people at pharma companies, their career can collapse if they make the wrong decision. David de Gruel, founder, Anto YCF25. People tried one bag, paid $15 plus $7 to ship it, and thought, I didn't love it. But if you set a minimum buy and they buy 5 bags, the chances of coming back go up astronomically to about 40%. Michael Blumenkrantz, founder, The Wicker Ball Strangers Kept Asking to Play With. Morris has been playing with a hand-woven wicker ball for 12 years, long before he thinks of it as a business. Everywhere he plays, strangers walk up and ask to join. It's the most magnetic thing I've ever launched in all my career. He pitches a friend and fellow men's group member, who had just sold his web company, to partner on it. The friend says no for 4 years. Then he returns from a year in Japan with no next step and finally says yes. They launched late last September, right into a Canadian winter. They sell mostly in person at flash mob mini festivals and win a helicopter commercial shoot worth $10,000 to $20,000. The rules are simple: keep it up, don't say sorry. If you do, there is an optional push-up. Have fun! That story is from: We have created a stereotype of negativity that all of us who call ourselves salespeople live in. My friend asked his daughter if she knew what a cold call was, and she said, "Yeah, it's spam." Dale Dupree, founder and CSO, The Sales Rebellion. Before anything else, I ask, "Can you pick up a phone and call a stranger?" A lot of people do everything other than the actual work of selling. When I advise startups, the number one thing is to call a customer. If you struggle to do that, you have bigger issues. Douglas Crystal, founder. True video. How OpenVC got investors to fix their own data. Stefan Nasser's first real startup, Petri, tries to build a company around single-cell technology. It dies in about a year. We tried really hard. We failed. But the pain leaves a lesson. He needed investors deep in life science tools, and finding them was far too much work. So he builds OpenVC, a free platform where founders and investors find each other. The first investor list is scraped and wrong, and investors are furious to see their outdated names. Nasser turns that into the growth engine: a button to claim and edit your profile. Funds, or their heads of marketing, flood in to fix the data. Then comes the second wave: funds who see rival logos on the site and want in. Today it is profitable, runs with a tiny team, and charges for premium, never equity. That story is from: I got 35% of everything I sold, forever, for as long as the client had a subscription. For 2 and a half years, I just built up my own book of business and built systems for customer success, sales, and marketing until I had a larger book of business than the company itself. Johnny Page, Chief Revenue Officer, SaaS Academy. I took my first job after graduating software engineering making cold calls. My parents lost it. But fast forward, I am everything I am because of those sales skills. As an entrepreneur, you are convincing customers when you have no product and convincing people to work for you when you have no money to pay them. Co-founder, Bose.ai. Bought out on April Fool's Day, profitable in 30 days. Drew Donaldson is a year into Crackle, an agency he runs with 2 partners from the big agency world. They had hoped to hit a million dollars in the first year. Then they blindside him with an offer: buy us out. He says yes, and that month becomes the best in the company's history. Overhead is the real problem. Partners had loaded the business with HubSpot at two thousand dollars a month, a content agency at five thousand dollars, an accounting firm at one thousand dollars. We signed it April one, which is kind of funny. April Fool's Day. For the first 30 days, he fires every vendor and cleans house. Within a month, the agency is profitable. He then rolls back the coaching price hikes, turns on paid social, and triples the business. His first hire is interviewed in a hospital parking lot 24 hours after his wife gives birth. That story is from We weren't selling mattresses; we were selling good sleep. When someone walked in, we never talked about what mattress you need. We asked what problems you're having with sleep and how we could help. Ronald M. Bazaar, CEO and co-founder, Tasty Picks International. Never be shy. Talk about what you're good at and your skills, because you don't know where it could lead. I ended up CEO of Fantics US branch after a night at an Italian winery. Steffi Bao, CEO, Init Sports. A pharma company with franchisees, not an army of reps. Barry Patel sees a problem inside Big Pharma. Companies send out armies of sales reps, but 80% of your sales are going to be generated by 20% of your sales reps, and the company still carries the rest. So Galt, which Patel co-founded with Wade Smith, does something nobody has done: it sells territories. A franchisee pays $200,000 for a 5-year contract to educate doctors and pharmacies in their community, then keeps a share of the revenue. They have skin in the game, so they skip the big lunches and speaker programs. Today, Galt has 53 territories across 17 states, 35 employees and no manufacturing plant. That story is from— We did everything we possibly could as fast as we could. That's how you grow to a $300 million channel in 3 years. You don't test, you just do everything. Jeff Atkinson, CEO, Huckaby. When it comes to work, I always tell people, make $1. Figure out a way to make $1 from anyone on anything. Our first customer, we charged about a twentieth of what we currently charge. Robert Harary, co-founder, early-stage VC investor, Razy, Deco, Evolution VC Partners. Three busted startups, then a book that sold billions. Patrick Renvois is a French transplant selling multimillion-dollar supercomputers in the U.S. when he starts some startups of his own. He loses all his money three times. I was never smart enough to diversify my portfolio. So he does something else. About 25 years ago, he writes a book on a brand-new idea he calls neuromarketing. He recruits his tennis partner, Christophe Morin, who has a PhD in the subject. The pair discover Daniel Kahneman's work and decode 6 stimuli that speak to the ancient, 500-million-year-old brain that actually makes buying decisions. Today, Renvoz has 3 million miles on airlines and estimates their teaching has helped close between $5 billion and $6 billion of additional business. That story is from— we posted on social media and people were chasing us down for the links. In 10 years of startups, nobody had ever asked me for a link. We got to 5. $5K MRR in 7 months with 58,000 downloads because we just did what they asked for. Michael Yagudayev, co-founder, CreativeFlow.ai. When I started in Hong Kong in 2002, there were fewer than 10 trained coaches in the whole city. They're excited by something new, but they wait for someone else to do it first. Many people packed up within months because the excitement never turned into business. Charlie Lang, CEO, coach, and founder, ProgressU. 800 sales from one conference in Thailand. Michal Suski and his brother are barely 2 years into building Surfer, an SEO tool born because their agency could not hire in a tiny village. It is 2019, and they fly to a conference in Thailand packed with affiliate marketers. Affiliate SEO is at peak performance, so the crowd is wealthy and hungry to scale, and they spend on tools like crazy. Suski's team shows up with the product. There was like 1,000 people at the event, and we closed like 800. Almost the entire room becomes a customer. Years later he still goes, but now mostly to see friends, because everybody already knows them. His advice for anyone copying the move: sell an SEO tool at an e-commerce conference, and never expect the same city twice to pay out the same way. That story is from— The Dragon's Den is not about getting on there so they give you money. It's television. I call it smoke and mirrors. You have 90 seconds as a hero or a zero. Make sure you look like a hero because they can play you as a villain. Kevin Halliday, podcast host, president, Shed Talk, Spindle Stairs and Railings. Airlines and air travel just collapsed, but we saw a lot of new partnership opportunities. In six months, we signed six new deals with airlines we had never spoken to, including Air France. That brought our original investors back to the table. David Gunnarsson, CEO. Dohop. She waited 20 years for the one idea she believed in. Carmen Lee starts out as an option market maker in Chicago, then moves to Citibank, then runs global data integrations at Bloomberg. She has always wanted to start a company. But she has never had the conviction. I have to convince myself first. She calls it a quarter-life crisis every quarter. Then, in 2024, it clicks. To build a tradable index for GPUs, she needs trading, data licensing, regulated finance, and hardware, and she has all 4. No one else understands servers. She launches Silicon Data, an index layer for compute, and Compute Exchange, a marketplace for GPUs. Silicon Data hits 7 figures in ARR with no salesperson. CME is about to launch futures on her indices. That story is from— I call it, you can predict the future and twist the knife. If you know your buyers so well that you can predict their next two weeks, two months, two years, and they're like, "Oh crap, he's right," then you can say, "If you don't make a change, this is what your future looks like." That gives you immense leverage. Josh Wagner, co-founder and partner, Revenue Capital. There were about nineteen people at Certain when COVID happened. We had just raised our seed round. I said, "We're doubling down." Hiring managers are bored. Property managers aren't showing properties; they're improving systems. We sell harder than anyone while everyone else is on their back foot. Andrew McLeod, co-founder and CEO, Certain. The $10 million bill that a one-month demo beat. At South by Southwest, Yash Gad's team at Ringer Sciences demos an early AI product. Afterward, he hears a rumor he can barely believe. A big pharma company, which he will not name, had spent about $10 million building the same thing internally. It had taken them a couple of years. Yash's team built their demo in under a month. It wasn't anywhere close. Pharma clients always say they have giant analytics teams, he explains, but when his team checks back in 3 or 6 months, they shake their heads. They are never happy with what they built. That South By moment tells Yash his firm is onto something. Coming at builds from first principles, he decides beats the way internal teams do it, and it pushes Ringer from consulting toward products. That story is from I Like to Fund Off of Sales. Sales is the only sustainable way to fund your company. Full stop. Jim Weldon, Chief Executive Officer, Prospect Desk. We started with paid media, and I realized I was just putting money into the Google black box to compete with other people putting money into that black box. So we formed partnerships with major corporates who offer us to their customers at zero cost to us. Saul Kornick, CEO and founder, Kana Health. The salesperson who watched cold email die. Ryan O'Hara spends his early career cold calling and emailing data center managers for Dyn, then becomes the first employee at LeadIQ. Every year, his team surveys customers. In 2016, cold email replies averaged 6% and cold call connect rates 10%. In his last year, the reply rate is 7%, but connects have collapsed to 3%. It's all trending toward zero. So he builds Pitchfire, where salespeople pay buyers to read their pitch. His first idea— buying meetings outright— is too hot. Paying for responses is just right. Then his only angel investor, the former Glidefest CEO, dies of cancer, and the follow-on funding disappears. Ryan keeps building, now with about 2,600 daily users. That story is from— I space each event out once a month at each location, around 4 weeks apart. It creates a sense of scarcity and gives time for the event to sell out. Mike Reed, founder, SoundQuest. The expert class in startups and DTC said brick and mortar was dead, that no one would ever buy anything in a store again. That was just absolutely ridiculous. So we built wholesale from the very beginning. And today we're in over 1,000 stores. A client tossed a football with a Super Bowl quarterback. Lee Barcalow starts in the music touring world, at an agency where access runs on favors. Everyone wants in, almost nobody gets in. When he leaves the agency, he leaves with the relationships. He starts Current Group to sell what he calls bucket list access, in Los Angeles and London. The pitch is a promise that someone is one or two phone calls from almost anyone. That's a big promise. A Bear Grylls survival week runs mid-5 figures to low 6. One Super Bowl client meets a quarterback the day before the game. Toss the ball around with him and his son, then he watches the game and joins the field afterward. Lee says his team has put in more than 20,000 hours, and he can smell out a deal that doesn't feel right immediately. That story is from— The other choice was municipal applications. But the problem with government is that it's incredibly slow. The procurement cycles are so long that the company may die before you get a contract. That's why I went to retail. Greg Tanaka, CEO and founder, Percolata. When you create a niche product that works really well, it becomes relatively easy to sell. I sent free samples to every gym, restaurant, health club, hotel, and sports team I could think of. One restaurant put it through its dishwasher to test it. Kyle Ewing, CEO, TerraSlate? How a Pepe meme landed a call with Ubisoft. Kai Cabero spent his early career in recruitment, found cold email, and has been annoying people ever since. He now makes over a quarter million dollars a year by siphoning competitors' audiences, scraping the followers of big creators and emailing them offers that mirror the ones they already follow. His best story involves a growth consultancy in the blockchain space. Kai is doing their go-to-market and wants Ubisoft as a client. His follow-up is not a case study. It is a Pepe the Frog meme. Ubisoft is a French company, so it could have gone either way. It worked. They got on a call. Kai says memes are a last-ditch pattern interrupt, but he has also landed calls with Samsung and Fox Network, sometimes in his shorts. That story is from 69% of sellers said the hardest part of the sales process was getting the first conversation. The 20 major sales training companies all start at the hello and end at the close. What was lacking was the pre-hello. Mario Martinez Jr., CEO and founder, Vengreso. What used to be a 45-minute sales call is now 7 minutes of exchanged audio over the course of 12 hours with the same result. If people want to work with me, they have to get on Voxer and start a conversation. Ari Meisel, founder and business coach, Less Doing. At 27, he ran a top digital agency and got schooled. Bob Morris is 27 when he becomes CEO of the Inmar Group, then the 5th largest digital agency in the world. Its clients include Cadillac, Buick, Pontiac, Jeep, Chrysler, Dodge, and Eagle all at once, plus AT&T, Fujitsu, and Alcatel. Back then it was called multimedia, and the agency started with discs. Its investor is the family behind Lane& Bassett Furniture, whose son is friends with AOL founder Steve Case. His board includes people from Wharton. It's a lesson in humility and a hurry. In 2016, he sells a later firm to a large public company, then spends over 3 years in the earnout. That convinces him there is room for a specialist M&A firm for the digital ecosystem. He co-founds Bravery Group and leads a $295 million agency deal. That story is from our LinkedIn message said, "Hey, I'm Cameron. We use AI to help authors market their books." When I tell you we got crushed with that campaign, so I took the words AI out of it, and when I tell you my calendar was booked and full, Cameron Clarkson, founder Book Blaster Hulu Labs. Last week we had three million accounts reached. Out of that, there were twenty-five thousand profile clicks. As a creator, you think. Wow! But out of that 25,000, only 24 people clicked on an actual offer. Those engagements turn into dollars over time, but you have to follow up. Daniel Powers Jr., founder, Real Brave. He paid to get a job and it launched his career. Nick Roche drops out of university because he cannot pay tuition. Nobody wants to hire him. The only company that calls back is a door-to-door seller. On his first door, a pizza place, He freezes. I couldn't even say hi. Within 3 months he is the top salesperson in Canada. Then he sees the ceiling and looks for leverage. He finds an online sales role, but the final step asks him to pay for the training. He has never paid for a job. He does it anyway, on his girlfriend's credit card. Selling online margins run 80 to 90%. He starts with outbound email, learns copywriting, then closes his own calls. In 2022, he starts AdMRR, whose first client goes from $127K to $326K MRR in 90 days. That story is from— It's kind of like asking a girl on a date. You don't ask her out and then ask her to marry you the first moment you meet her. You invite her to a concert. Raising capital is relationships more than it is anything else. Jeff Barnes, CEO, Angel Investors Network. There's basically no correlation between how good someone is as a coach and how good they are at talking about themselves to get clients. So the industry is quite broken, and there's a massive opportunity to be the person who can do both. Executive coach and writer. Former COO of ConvertKit. How a studio can make a hit look like a loss. Sharif Bennett's explanation of why even a classic like Blade Runner can lose money starts with paperwork. A studio forms an LLC just for one movie. The writers, directors, actors, and investors are promised a percentage of the profits. Then, as Bennett tells it, the studio throws every expense under the sun into that LLC— marketing, sales, any level of promotion it can find. On paper, the movie never turns a profit, and the people promised a cut see nothing. This is called Hollywood accounting, and Bennett's company, CineBlock, was built as the answer. An equity crowdfunding platform where filmmakers label spending clearly and investors know what return and which distribution rights they hold. Films, he says, were kept in the dark from the people who funded them. That story is from: We opened the doors in 2008, one of the worst years in all the markets. But when a market blows, compliance is pretty hot. The core customer didn't change, but their needs changed. So we shifted our messaging. Shannon Burns Susko, 2x exited CEO, founder, Metronomics. We always come in as a neutral third party. It's like hiring an accountant to audit your finances. We have nothing to do with the pollution; we just help you get clean records around your water usage. Dolavant, founder and CEO, Aquagenueity. Speed dating with buyers that put salt in Target. Cherie Hoger and her husband sign up for eCRM, which she describes as speed dating for buyers and new brands—26 retailers in 48 hours. They practice their pitch on tired male grocery buyers who have never seen a menstrual cup. Then the Target buyer walks in, a progressive woman originally from Nigeria who knows she wants a cup on shelves, just not which one. She flips through the packaging, gives advice on the size guide, then pauses. I've looked at a lot of cups, and I mean a lot. Cherie braces. I think your brand is best positioned to take this mainstream. Target had always been their measuring stick. They negotiate exclusivity in year one and launch nationwide the next year. In their second year of business, that story is from. I started a challenge. Every day I filmed 30 seconds of myself eating locust products, and the only difference between the clips is the counter. I had about 80 followers on Instagram, and the first videos got 10 views. Three months later, over 600,000 views. Dror Tamir, founder Holy Locust. I pitched the writer directly because no one at the publishing company seemed to be doing anything. That story ran, and then it was really reactive. We started getting publicity off of the publicity, and we were on our 12th printing by our pub date. Nicola Kraus, founder, bestselling author, and book coach. The finished thought: 50,000 websites sold over the phone line. It is the mid-1990s, and most businesses do not even have a website. Gene McCubbin, 25 and not a coder, starts a company that cold calls brand new businesses with a pitch. A $50-a-month website. He bills customers through their local phone company. 40 employees sell full-time on the phone, with call centers in San Diego, Indiana, Chicago, and Houston. The pitch lands with about 50,000 customers. But the model is a Ferris wheel. Customers leave after 4 to 6 months. He sells to a small public firm in a deal worth about $7.5 to $8 million, though after raising $2.5 million, he owns only about 20%. It buys his first house and his first Mercedes. Then he builds the next agency and the next. That story is from the most successful go-to-market we've had is non-scalable, but it's physical. It's in person. It's speaking and building relationships. The bigger deals are done by getting to know someone, and some of our best customers have come from the events that we've hosted. Tom Charman, co-founder. Block. We did a pilot with an electric utility in the turbine room of a coal-fired power plant. We charged them for it, and at the end of the test, we bought it back. If we didn't do it that way, the test probably would never have ended. They bought 40 servers. Herb Zien, Vice Chairman, Liquid Cool Solutions, sitting in a 7-Eleven parking lot until the owner arrived. Shadi Bakur's first startup taught him a painful lesson. They poured 12 to 16 hours a day into the product, then forgot marketing, sales. Finance, and supply chain. For his water company, he needs retail. The big chains are closed doors, but he learns that a 7-Eleven franchisee controls 20% of what goes on the shelf. So the team goes door-to-door across California and the West Coast. Literally just sitting in the parking lot of the store until we see the store owner show up. They walk in and make a deal at all costs. That scrappy start builds momentum, and then the inbound calls come. Salesforce asks about a logo, then Chanel and SpaceX ask for bottles. At one point, their Made in USA bottle is the number one selling water at Walmart. That story is from. Change is always the first thing to go after in any engagement. There's change, time, and money. If you can't get the change to happen, the time and money are irrelevant. Doug C. Brown, founder and growth partner, CEO Sales Strategies. You're not just selling a solution; you're selling a return on investment. It's not a cost center; it's an investment. Sales cycles run 12 to 18 months, sometimes 24, and a CIO who moves to another group takes us with him like a business card. Yassine Benali, co-CEO and board director, Okadoc. 0% to 15% in 2 weeks. One of ISO's customers starts with almost nothing. Its website is basically a landing page of generic, top-of-the-funnel information, the kind ChatGPT never needs to consult. It is a relationship-driven, high-ticket B2B business with about 2% visibility in AI answers. Benjamin Tannenbaum's team opens the real conversations data and picks the next 2 articles the company should publish. The customer writes them and goes literally in 2 weeks from 0% to 15% visibility measured across hundreds of detailed Tannenbaum says the curve is logarithmic. The better you already are, the harder each extra point gets. One client at 75% visibility needs the same effort to gain a single point that this one needed to gain 15. The biggest winners, he says, start at the bottom. That story is from: One customer was blasting and praying lots of cold emails that weren't working. We gave him 5 leads every day, based on his favorite customers. 2 weeks later, he hit us up saying he'd closed around 50% of them to a first meeting. Low volume, high quality. Mark Evgenyev, co-founder, Dsync AI. Chapter 6, Building Product Tech, the Pivot, and Knowing What to Ship. You can't say you got distracted unless you know what you got distracted from. The goal of timeboxing is not to finish. The point is to work on that task without distraction so you can see how long it takes you. Author and behavioral designer, Hooked: Indistractable. A lot of customers at Restore would say, I did cryo today, I don't need the exercise. No, cryo was not to replace exercise. Cryo was to make it easier to exercise. Co-founder and CEO, Humanaut Health. Maxed out credit cards to a $10 million media company. In 2008, Joe Pulizzi is deep in debt with every credit card maxed out, and he is seriously considering going back to find a job. He has just left publishing to start a company, and the finances will not work. Instead, he pivots into what becomes Content Marketing Institute. His wife, a former social worker, joins to run operations. The company is a couple hundred thousand dollars in 2010 and a million-dollar business in 2011. The engine is a risky bet: an in-person event, Content Marketing World, in Cleveland, Ohio. He hopes for 100 to 150 people. We ended up getting 660 people that year, he says, and eventually 4,000. By 2015, the company is a $10 million business, and in 2016 he sells it for what he calls generational wealth, after quietly building a list of potential buyers 6 years earlier. That story is from: I told my company a year ago, you guys, this isn't working. Make it idiot-proof and addictive like crack cocaine. There's one product that got to a billion users in 2 months with no salespeople and no marketing, and that's ChatGPT. CEO, Humantelligence. Listen to your customer. Don't have them fill out a form. Spend hours and days with them and understand their challenges so you can design a product that really answers their challenge. Founder, Certus Insurance. The farm that swallows 4 inches of rain in 5 minutes. Mitchell Hora is a seventh-generation Iowa farmer. His family has worked the same ground for 152 years, and by the 1980s they had switched to no-till because of extreme weather. He has seen what healthy soil does. Before the family used regenerative practices, they replanted part of the crop almost every year. Heavy May rains would drown it. They have not replanted in about nine years. The national average soil absorbs half an inch of rain an hour. On my family's farm, we can infiltrate 4 inches of rain in under 5 minutes. Hora turns that into a software company, Continuum Ag, which measures a farm's carbon footprint per bushel, verifies it through a third-party ISO audit, and lets farmers sell the result. On his own farm, soybeans score carbon negative. That story is from— If Andrew Huberman talks about magnesium, I can get that in a beverage within 30 days. We control our own manufacturing, so it's a sunk cost. I can see what's coming and act on it quickly, then test it online. Founder and CEO, GoBrewing. It's better to do longevity in dogs because in 5 years you can have a very good idea if it actually helped, whereas it would maybe take 10 or 20 years in humans. CEO, Dog Years. The Uber secondary that cost investors a third. Michelle Friedman watches the Uber frenzy. Investors pile into private rounds at a $100 billion valuation while smaller investors are pitched secondaries at $60 billion, a 40% discount. He hears the big primary investors have a liquidation preference, which turns their equity into something close to a convertible bond. Uber then goes public at around $40 billion. The primary investors are fine, he says. If you invested in a secondary at $60 billion, which had a liquidation preference maybe down at a billion or even less, you were screwed. They lose about a third of their money with no annual report, no information rights, and a letter saying they are sophisticated investors. That story is from— instead of working for a client, I started building websites in all of the niches I was already in, keeping all the leads myself and renting them out to a business owner, charging a rental fee like you would on a physical property. Luke Vanderveer, CEO, Website Rental Coaching. The car is not very fast when it's in the workshop. You need to put it out on a track at some stage. I've said that to my researchers time and time again. We have to put this out and see what happens in the real world. I know it's not ready yet. I know it's not perfect, but we have to find out. Cameron Vanden Dungen, CEO, former racing driver. Sleep tight. A taxi ride in Mexico City that almost ended badly. Jordan Harbinger is 20, living in the poor hills of Mexico City, when he flags down a taxi. Something is off. The driver heads up and away from the center, claims there is traffic when there is none, then says he needs to ask for directions. He pulls up at a cinderblock house with no lights. Jordan slides his hand behind the driver's seat. At 209 pounds, fresh from the gym, he faces a man in his 50s. He wraps his forearms around the headrest and squeezes until he stopped breathing. The doors are rigged shut, so he pushes the driver's unconscious body out, grabs the keys, throws them, and runs. A passing doctor tells him not to bother with the police. By morning, he is on a bus to Guadalajara. That story is from... Restaurants are not that different from software. There's a front end and a back end. The front is beautiful, and we make sure it's presented well. In the back, it's always a mess. It's very frantic. You never stop, and there's always something breaking. Alan Zhao, co-founder, Warmly. What I learned in astrophysics is that we always miss simple ideas. So I asked, what signals in the body are we not fully utilizing? There is so much blood flowing through our body. There must be other signals as well. Anna Barnaca, CEO and founder, MindMikes. The pivot after a year and a half of traction. For almost a year and a half, Vamsi Seladi and his co-founder build a QA dev tool. They go through YC with it, raise a pre-seed, and land real customers with real usage. It feels like the real thing, but every sale is an uphill battle. The burning need is just not there yet. Worse, they had sold the product to the very person it was meant to replace. Everything feels grimy and forced. So they walk away from users and money. 6 or 7 months before this interview, they spot voice AI about to take off, and friends in fintech point them at a painful problem: bank customer support. Now they sell AI support to banks and credit unions, aiming at contracts of $50,000 to $100,000 a year. Their investors, he says, were incredibly understanding. That story is from— In 1916, we had about 250,000 miles of rail, Today it sits around 140,000, and we use maybe 47% or less of it. Rail is the most underutilized resource we have in the United States. Founder and CEO, GLID. If I want to support people, I can't tell them everything to do. It's to find their just one thing to do right now. Because typically, anything greater than one equals zero. CEO, Potato-sized rocks worth trillions, 4 miles down. Oliver Gunasekera spends about 30 years in semiconductors, an early employee at Arm, before chasing atoms instead of bits. His discovery? Potato-sized rocks lying across the deep seabed, the planet's biggest source of nickel, cobalt, copper, and manganese. Each centimeter takes about a million years to grow. Rivals plan to vacuum them up with dredging tech tested in the 1970s. Oliver takes a blank sheet of paper and builds an autonomous robot that dives up to 4 miles and picks them up one by one with a buoyancy engine, a delta-style arm, and onboard AI. He names the company Impossible Metals because nobody believes it can be done, which helps him recruit the best engineers. After YC in winter 2022 and a seed of more than $10 million, the U.S. Interior Department accepts his request to begin leasing around American Samoa. That story is from: How do I scale a $3,000-a-month bill to a bunch of small businesses? Spoiler alert: you don't. We needed to give agency owners a business where they could say, it's $300 a month, it's all powered by technology. Sean Clark, co-founder, HighLevel. Everything in the supermarket has a nutrition fact, even junk food, but fruit has none. If they put it, it would be horrible in America. We only buy for the look. Inside, it's empty. Sahin Boydes, co-founder and CEO, Klaros Farm. A physicist turns a podcast guest's phone into a cloud. Dan Desjardins, a former Canadian Army officer with a physics PhD, has a problem. His simulations always need more chips, and a single cloud instance can cost $1,500 for 3 hours. So he builds software that turns any device, from laptops to fridges, into one pooled computer. Then, live on the podcast, he proves it. He shares his screen and asks the host to open a link in a browser tab. The host does it on his iPhone. Dan dispatches his own physics research as a job. Under 5 seconds, we created an instantaneous cloud using your computer and my phone. A progress bar moves, the results come back, and distributed computing has happened in under 10 seconds on arbitrary devices. The host has just joined the network. That story is from— There are over 8,750 active satellites in low Earth orbit right now, constantly pulling pictures. So why not take advantage of the capacity of what's already happening and monetize it? Kate Van Damme, Head of Strategy, SkyFi. Most startups can reach $100 million in revenue with one product. You have to be laser-focused. If Bezos had said in year 1 that we'll also compete with Netflix and do servers, he would have done nothing. Managing Partner, Lobster Capital. The 25-year-old who said yes to being CTO by accident? Jay Dhawani has just come back to Canada from the Bay Area, thinking about starting something in blockchain. Then someone he knows asks him to look at a company in dire straits and tell them if it is salvageable. It is an early version of the metaverse, an online gaming platform with a secondary market, All hosted on blockchain, and it has already been through a merger. Unbeknownst to him, it is in terrible shape. He only cares about the tech. He tells them what makes sense and what does not. They ask if he wants to be CEO. He is 25 and refuses. They ask if he wants to be CTO. He thinks, "What's the worst that could happen?" He jumps in, turns the company around, and it is eventually acquired. He later calls it totally by accident, the way best things happen. That story is from: One entrepreneur told me every interview on my site should be a landing page, not just a play button but an enter your email to get it. I thought, that's a lot of work, so I filed it away. Today that's one of the biggest sources of leads. Andrew Warner, CEO and host, Mixergy. For the first 2 or 3 years we would answer every single phone call from a customer. It kind of sucked, but it gave us so much insight. Sometimes a customer called about a bug and one of us would literally start coding, upload the fix, and solve it right on the spot. Chairman of the Board, Brevo, formerly Sendinblue. Steve Jobs shows 20 people an ad with no product. Apple is in its dark days. Steve Jobs has just returned and the company has no new product to sell. Cameron Craig's first campaign at the agency is Think Different. 90 seconds of black-and-white footage of Muhammad Ali, Einstein, and other difference-makers. It airs in prime time with nothing to buy. But Cameron says the real story happens inside the company. Steve invites about 20 people to his home in Palo Alto and plays it in his lounge room. They had a reason to believe in Apple, a reason to stay. These are the people who will endure blood, sweat, tears, weekends away from family and Steve's bad moods to build the products ahead. The biggest thing Think Different ever did, Cameron says, was change Apple from the inside. That story is from Cancer cells duplicate every one to three days. A year later, you can be a hundred generations down in evolutionary terms and have many families of cancer cells. Having one drug to kill all of them is very unlikely. Roy D'Souza, co-founder and CEO, Break BioCorp. Terraform's business model is not that different to Costco. I aspire to produce gasoline for $2 a gallon and sell it to consumers for $2.20 a gallon, take a 10% margin, and then make a ton of money by making trillions of gallons of gasoline. Casey Hanmer, founder, Terraform Industries. A 10-year-old eBay scalper and his chauffeur mom. At about 10, Cole Dermott is a huge Nintendo fan. When the company releases collectible figurines called Amiibos, he sets up what he calls a full eBay scalping business, reselling them for very small profits. His mom backs him every time. He still remembers her picking him up right after school and driving to whatever store might have the new drop just to find it before it sold out. She is, effectively, his chauffeur. Meanwhile, his dad, a university dropout who climbed the sales ladder, is full of ideas but chained to the corporate world. Cole watches that firsthand. Years later, walking away from Coinbase, he reaches his own conclusion. At his age, it is the pragmatic thing to do, not the hopeful one. That story is from The History of U.S. Military Interrogations. We only gained cooperation. Our average was about 4%. I created this process, and it took us from 4% cooperation of prisoners to 65% cooperation. Eric Maddox, speaker. Author, former Army interrogator, Ermatics. Search is the point in time where the past and the future meet. You are looking to the past to find a solution for something you're going to do tomorrow. So I wanted a typeface heavily based on the history of typography but also modern. Ruth Kedar, founder, designer, and artist, Kedar Designs. The law that keeps drugs from reaching patients. A new medicine takes 10 to 14 years to reach the market, and its patent only lasts 20. That clock, Scott Stout explains, is why drug prices are so high. Then comes the trap. HIPAA says you can't buy a list of patients. The FDA says you can't sell a drug without trials. And you can't put up a billboard naming the drug, only one that asks, Do you have X? Call this number. Scott asks Charles when he last dialed a number off a billboard. Never. The cost is staggering. When Humira's patent expired, The gap between last year's sales and this year's forecast was $20.5 million a day. Scott's company, Medvector, gets around the bind by working through each patient's own treating doctor. That story is from If You Can Make Somebody 10 to 20% Better at Their Job, They'll Pay You Through the Nose. But if you make somebody 100 to 200% better, that's insulting because then they don't know what to do with the other 23 hours of their week. CEO, stealth fintech startup, formerly Resistance Bio. The average cost of a blood unit today is about $200, and our target is to reach about $50 per unit. That can be achieved when we manufacture at very large scale, hundreds of thousands of blood units. CEO and founder, Red Sea Biotech. The office hours that turned into Paul Graham's check. Midway through the YC batch, Vihar Nandigala and his co-founder get an email from Paul Graham. He is in town, he liked their idea, and he wants to do office hours. There is no pitch, no deck. They head to his house and sit on the patio for about an hour, talking sales and where it is headed. Paul is intrigued by their anti-AISDR thesis, a belief that go-to-market should get more creative. He really thought the idea could become really big. Then he makes the offer. Hey, I'd love to invest in you guys. The founders have not even started fundraising. Paul Graham becomes their first angel, which kicks off a round that eventually reaches $5 million. Fundraising, Vihar says, is a momentum game. Really, really hard to monetize a community. We didn't even try, because it just didn't feel authentic. So I eked out the money for the whole 3 years. I spent less and went back to the drawing board. Founder, Storyboard. There's not a feature in the platform that wasn't asked for by a customer. We don't build things that we think are cool. We just listen as deeply as we can, and they trust us. CEO and co-founder, Improve On Health. The company that started with pigs. David deGruyel's lab at Harvard Medical School depends on pig studies. Because a pig's stomach is similar in size to a human's. The lab's logo is even a pig. But the team begins to see a problem. Pigs are smart, domestic animals, and the only reason scientists still use them is that recreating a human digestive tract in a lab is neither accurate nor scalable, and a pig's microbiome is different from a human's anyway. So David and a labmate wonder if computation could solve both problems at once. That question becomes Antho, a Y Combinator F25 company that trains foundation models to predict how gut Microbes change the way we respond to drugs. If you simulate a human microbiome, you solve both that scalability problem and the accuracy problem at once. That story is from when we get abuse requests. I respond that we ban the user, but in my head, I'm immediately thinking: I don't want to be doing this task again. How do I automate it? How do I create a runbook so my support agents can handle it? Matthew Tsai, CEO. For a time, your moat was the number of engineers you had. That's gone. People can replicate almost any application anytime. But if you have distribution, you can upgrade your client base far more easily. 5x CEO, founder, AI for EBITDA, Outforce.ai. Told his career was a mistake, he did it anyway. Dave Messina is a young researcher chasing a disease gene. His first published paper is a triumph. The team narrows the causative gene down to a million letters of DNA. A million. That is how blind the field is before the Human Genome Project. He sees something others do not. Genomics, and computers to read it, will reshape medicine. He seeks out the one or two places on Earth with real computational biologists. His mentors sit him down, one meeting after another, This is a mistake, they tell him. No interesting research, and no one will hire him. He goes anyway, later founding CoFactor Genomics, running a national clinical trial, and winning Medicare reimbursement. I'm glad I didn't listen to them. That story is from One Well-Known Technology published an independent AI audit that boasted a 90% pass rate on fairness. What's the point? If everyone graduated with A's, how would universities decide who to accept? If everyone passes, of course there's no discrimination. Barb Hyman, founder and CEO, Sapia.ai. I've tried to found businesses in areas that I felt were inevitable. Would we have a mobile internet? Fairly inevitable. Would all products in the world become trackable and traceable? Fairly inevitable. And then it becomes an execution issue. Niall Murphy, founder and managing partner, Morphosis. Why users kept moving addresses to Italy on Google Maps? Liam Bowling is a product manager on Google Maps, and he has a puzzle: more than half of the suggested edits to addresses are terrible. Someone takes 123 Example Street in San Francisco and says it is actually in Italy, or in New York. Focus groups tell him nothing. User feedback tells him nothing. So he stops asking and starts watching. What did people do right before and after the edit? Right after, they search for moving supplies. Right before, their location is nowhere near the old address, but at the new one. They are moving. They do not know how to change their home shortcut. You could never ask any of them; they would just lie. That insight becomes the thesis of his company, Deep Prediction. Watch the session replay, not the survey. That story is from I don't like founders who are in love with their solution. I prefer founders who speak about the problem. Because every solution is a temporary thing. Victor Orlovsky, managing partner, R136 Ventures. Each one of my companies was a problem I had that got super frustrating for me. I basically said, if no one's going to solve this, I have to solve it. Stuff I was building was crashing, so I built the thing to tell me why. Jeff Siebert, CEO, Digits. 2 brothers shot down a rocket with an air cannon. 11 weeks. That is all why Combinator gives Sebastian Fischer and his brother to show a missile defense company is real. A space-based demo is impossible in that window. So the 2 brothers drive out to the Nevada desert, launch rockets sideways, and build a computer vision infrared tracking system that predicts where each rocket will be next. Then they point a high-powered air cannon at the sky. The system tracks, calculates, and pulls the trigger at the right moment. Automatically shooting down the rocket. Sebastian, an MIT aerospace grad who worked at NASA, Lockheed Martin, Cruise, and Amazon, quit comfort for purpose. I didn't feel a sense of purpose waking up in the morning, he says. Now his startup, Wardstone, is aiming the same idea at hypersonic missiles from satellites 400 kilometers up. That story is from. I'm the kind of person who, if I have an idea. I execute it. I came up with an app where people send and receive virtual hugs. CNN picked it up, and in 2 weeks we had 80,000 people on the app, and we were not prepared at all. CEO, Init Sports. To make a screenplay that a company like Amazon will put 9 figures behind blows away any startup in tech in terms of a gamble, because there's no scientific proof this thing is going to work. The only thing that might work is the team. Simon Kelton, writer, adventurer, investor, founder. Inspirational adventures. A decade of failed runs before a single hit. Hologenics spends the first 10 years of its life failing in factories. Its infrared mineral technology works in small batches. But when Seth Kasdan's team tries to make 10, 20, 50, 100 tons of yarn, it wrecks the machinery. Yarn extruders are built with filters and screens to remove particles, and here the company is adding a mineral matrix that, as Kasdan puts it, is in essence dirt. Cost is the next wall. Years of work bring the price from over $30 a kilo to under $5. Then the business model: he sells minerals at cost or even a loss, and takes a rev share only after a brand like Under Armour sells the product, which can take 18 months. Early on, it creates a lot of logistical and financial challenges. Today, there are about 65 brand partners and 10 published studies. That story is from: I found that 3 people was the magic number for performance, for motivation, and for having fun. So when I designed that sauna, I said it's got to accommodate 3 people. They hold each other accountable and don't even know it. Stephen P. Smith, Principal CEO and Founder, HOTYRX. If they don't know how to run a business manually, how would they know what to automate? It took us years to reach that insight and finally pivot. Rohan Arun, co-founder, agentspace.ai, cheat layer. A bank collapse, a firing, and $300,000 from family. Bala Kamalakaran is running an Icelandic bank's new India operation, having lunch with finance ministers when Lehman Brothers collapses. His bank has a 3 billion euro credit line with Lehman. Suddenly there is a hole nobody can fill, and the bank fails. He is promptly fired. I've never been fired from any job, he says. Nobody in Iceland will hire him. His Icelandic wife suggests moving back to the U.S. Part of him agrees. Another part says, screw this. He tells her he will fix something, and she asks what. He has no idea. So he begs his family for about $300,000, Backs a team building an Icelandic language model back in 2009 and sits with them every day. That startup is acquired in 3 years. So is the next one. And the next. He did not plan to become an investor. That story is from— The first genome we sequenced cost almost a billion dollars. Now it costs less than 100. Biology can be more efficient than traditional chemistry, and that's what has been missing in industrial biotech. Veronica Breckenridge, founder and managing partner, First Bite Ventures. We're not an AI product. I'm not going to write a new narrative just to fit the current trends. We're profitable, we're growing with a microscopic team, and I'd rather grow on my own terms. Co-founder, OpenVC. The rocket engine that looked like artwork. A car guy from Detroit walks into SpaceX for an interview. John Bucknell has spent nearly 15 years in automotive, produced about 8 production programs, and rose to deputy director of advanced propulsion at General Motors. Elon Musk wants rockets that look like mass-manufactured devices, not hand-built prototypes or even artwork. Bucknell tells him it cannot be done with things already engineered and tooled up unless he starts over. Musk answers, okay, fine, you're in charge of our newest engine. Bucknell becomes the first full-time person on what is now the most powerful, most efficient rocket engine ever built. Later called Raptor. Years later, he leaves to build the first commercial space-based power plant. That story is from. We didn't have enough money to pay for Unity or Unreal for the first game, so we had to build our own engine. And we made it, by the way. Olivier Madiba, founder, Kiroo Games. Too often it's cart before the horse. Too many projects in crypto focus solely on the token price. If we could just focus on the capabilities, The price will be there. Bitcoin would be over a million dollars already if it was just about what it can do instead of number go up. Joe Roats, founder and chief architect, Dragonchain. Sequoia backed it; it went bankrupt in a year. Sam Hasty is a former middle school math teacher turned angel investor. He has just written his first checks into early-stage companies, including Vector, a rocket startup and direct competitor to Rocket Lab. Sequoia leads its Series A. Then a $70 million Series B follows, with Shasta and Sequoia participating. Sam is feeling brilliant. I thought I was the smartest guy in the world. 12 months later, Vector is bankrupt. The lesson, he says, was invaluable. He now runs Active Impact Investments, a $110 million seed climate fund writing roughly $2 million checks, and his first 2 funds both rank in the top decile for their vintage. That story is from. Anyone can build a voice AI demo. You can vibe code it. The difficulty is production: accents, dialects, microphone issues, latency, dogs barking, cafes. Anything to do with voice AI is not cloud codable or vibe codable. It will hallucinate a lot. Ofer Samson, founder and CEO, Ezra AI Labs. We didn't need to call our plugin some ridiculous name like some of our competitors did. People were asking for extra. Export GIF or video, so it's called Export GIF or video. Every time they search for it, they find us. Michael Yagudaev, co-founder, CreativeFlow.ai, a fund for a technology always five years away. Olivier Tonneau spends ten years as a management consultant, then ten more investing a well-known French entrepreneur's money in early-stage companies. In 2018, he starts looking at quantum technologies and notices something. Something strange. There was no fund dedicated to that investment thesis yet. With a co-founder who is a quantum physicist trained under a 2022 Nobel Prize winner in physics, he sets up the first dedicated fund and makes the first investment at the end of 2018. Quantum has been, in his words, forever 5 years from market. Years later, Quantonation manages $250 million, has backed 35 companies worldwide, and runs with a of 10. They have screened over 700 companies, and some portfolio companies now employ more than 300 people. Tano still will not call it success until his first investors get money back. That story is from— At Kniv Publishing, we hired a 400-person team to publish 1,200 titles a year. With Spines, we publish 2,000 titles with fewer than 100 people. More than double the titles and a quarter of the people. The only reason is that we boosted our process with AI. Yehuda Neve, founder and CEO, Spines. Why are you building a pet robot dog for an old-age home? We're not running out of dogs and cats. They're not going extinct. You could survive as a novelty item, but not as a widespread consumer device. Jasmeet Singh, roboticist, founder and investor, Bearded Maker. From Israeli Special Forces to 3D-printed shoes. Elias Stahl starts his career in the Israeli Special Forces, a start he credits with teaching discipline and how to manage stress. Back in the States, he builds software for Fortune 100 manufacturers, and there he falls in love with 3D printing. He sees a big, grimy industrial machine out of step with the world, and he knows change will not come from inside the big brands. He moves to Portland, the footwear capital, To start Hilos, I didn't know anything about footwear. Within 18 months, his small lab launches five of its own product lines to learn the business, wins awards, and files its core patents. Years later, it has launched 3D-printed shoes with Steve Madden and a luxury runway label, and is opening a design tool called Interplay. That story is from a lot of the opioid crisis happened because the older products that were very effective went away. The opioids were the ones getting all the promotion. So we brought back 2 products and built a niche in pain management. CEO and co-founder, Galt Companies. The higher the costs are in healthcare, the more money people make. Your margin is kind of capped, so the way to make more money is to increase costs. That is a fundamental structural problem. Co-founder, SuperPower. A ballerina's scoliosis surgery ended her dancing. John Ashley has known Maya since the day she was born. She is the daughter of a close MIT colleague, a top oncologist, and Ashley has watched her ballet and skied with her family. At 11, she is diagnosed with adolescent idiopathic scoliosis. At 12, her curve hits 45 degrees, and the gold standard is a fusion surgery— titanium rods, dozens of screws, a spine locked in place. Afterward, ballet is over, skiing turns sedentary, and in her words, Any kind of spine movement would be a plus. Ashley, a career medical device executive, becomes CEO of Octus Surgical, building a tether that pulls the spine straight, adjusts with a magnet, and leaves it free to move. He has not treated a patient yet. First one is targeted before year end. That story is from. There is one thing about building a product, and there is another thing about living the product. I could build it. it, but I just couldn't live the product. Co-founder and CTO, Clicker. The first thing a prospect should see on your homepage is not a picture of your solution. That's based on you, not them. It should be a picture of them in pain. The pain is not a want; it's a negative emotion that resides in the subconscious. Co-founder, author, and speaker, Sales Brain. The boy in the bubble, And the pouch of milk. In The 1,980 Seconds, a young Viraj Main reads a Time magazine story about David Vetter, the boy in the bubble, who lives in a sterile plastic bubble because of severe combined immunodeficiency. He dies before his teens. The child thinks scientists could someday help a kid like that. Decades later, Main earns a PhD in human genetics, studying diseases like Vetter's. Then he becomes a father and sees pouches of pumped breast milk in the freezer. These are full of antibodies, he thinks. That idea becomes Lactiga: pooled antibodies from donated milk, bought from milk banks, purified into a nasal spray for immunodeficient patients who cannot mount a response to vaccines. Preclinical studies are done. The financing is meant to carry the company into clinical trials. That story is from— I don't have any stakes in any providers, which means I don't have control, But I'm completely unbiased. I charge the same fee to everybody. People trust us because we don't own anything. Carmen Lee, CEO, Compute Exchange and Silicon Data. A big pharma that I'm not going to name had spent about $10 million internally building basically what we demoed at South by. It wasn't anywhere close, and our demo we put together in under a month. Yash Gad, founder and CEO, Ringer Sciences. Sausage links of cord blood and a cheaper way to buy. At ImmuneBridge, CEO Nina Horowitz has found an unusual edge in how her team buys raw material. Donated umbilical cord blood is liquid gold, she says, but buying whole units is expensive, and most never get used. A unit has little segments heat-sealed on the end, kind of like sausage links, holding only 100 to 300 microliters. So ImmuneBridge buys just those from Bloodworks Northwest, 100 units at a time. Because their small molecule can expand stem cells, a tiny sample is enough. They grow them, turn them into immune cells, and run high-throughput tests, with machine learning pruning the losers along the way. Only when a unit lands in the top 5 to 10% does the team go back and say they want the whole thing. It is how a startup avoids buying hundreds of units to find one winner. That story is from— We originally launched as a company where you could buy meetings with people, and that porridge was too hot. Turns out, if you pay for responses, it's just the right sweet spot. Founder and CEO, Pitchfire. Early on, I was in the education business, which, as most people know, you don't want to be in. When we launched Açaí Bowls, it was a lot of time explaining to people what a bowl even was. Founder and CEO, Rush Bowls. A laser that points at mosquitoes, born from a kid's allergy. Tsuki Friedman is an aerospace engineer who moves from traditional aerospace to drones in Canada, then back to Israel to join Zygo. The startup begins with a personal problem. One founder's kid has an allergic reaction to mosquito bites. The team builds a system to detect and track insects and discovers something unexpected. People tell them the detector alone is enough. Mosquitoes are super easy to kill, Friedman says. You just don't know where they are. So Bzigo watches the room 24/7. When a mosquito lands on a wall or ceiling, AI verifies it, and an eye-safe laser marks the spot. It sells for $200. The next step is a microdrone that follows the laser and removes the mosquito, inside guards so nothing splashes. A first patent covers detection, a second covers the drone. That story is from. Bottles do 23% better than cans. When we worked with Pepsi, Recently, they asked what performs better on Instagram. Before, a human would manually tag every piece of content. We used computer vision and got the answer in seconds. Founder, Quartermast Advisors. It doesn't matter how many users you have. What really moves the needle is the people that live out of your platform. The ones that, if your platform disappeared, would be super annoyed, angry, and come to your office with pitchforks. Thomas O'Farrell, co-founder, Workana. 3 million views, 24 clicks. Daniel Powers Jr. runs a music school with 3 New York locations and an online platform, and he has spent the past year pouring effort into content. Last week, his Instagram reached 3 million accounts. That is the kind of number creators dream about. Then he opens the funnel. Of those reached, 25,000 clicked through to the profile. And of those 25,000, only 24 people clicked on an actual offer. Powers does not read this as failure. Engagements, he says, turn into dollars over time, but only with follow-up. Otherwise, it is pure wasted money. His lesson is that online, no one can walk into a beautiful studio and trust you on sight, so landing pages, copy, and email nurture have to do the job of the front door. That story is from Those technical moats used to be the thing. Now you can build something in hours or weeks, and AI has been democratized. So what is your moat going to be? We're back to the basics. What's your go-to-market, and can you sell? Managing Director, Ocean Azul Partners. Our customers gave us 2 pieces of feedback. One, you have too many services. We don't know what to buy, so we don't buy anything. I call that the Netflix problem. Two, I bought this thing and it didn't work, and it's your fault. Chris M. Walker, CEO Legit. The forecast that saw the Iran strikes when markets did not. Anthony Vinci spent years as an intelligence officer, then as CTO of an intelligence agency, then an investor at Bridgewater and Cerberus. Obsessed with how to answer hard questions, he founds Vico, an AI that forecasts world events. Then comes the test. Ahead of the U.S. strikes on Iran, prediction markets' Calshi and Poli markets sit around 50%. Nobody thought this was going to happen. Vico's model has been climbing for weeks. Above 50% 3 weeks out, between 60 and 70% 10 days out, about 78% a day or 2 before. The team publishes it all in a newsletter. We're like, no, it's happening. Vinci says the model is also bearish on the Strait of Hormuz fully reopening, favoring a no-peace, no-war equilibrium. That story is from— If they can vibe code their way to something that looks like the software they want, that removes a lot of the real cost of software development, which is building the wrong thing and misunderstanding what the client wants. Frank Wiles, founder, RevSys. A company that says we're going to plant a tree for every dollar that comes in, that is not the kind of company we invest in. The kind of company we invest in, the revenue is inextricably linked to the environmental benefit they provide. Mike Winterfield, founder, Active Impact Investments. The company that copied Segway then bought it. Tom Hegarty works with Ninebot in China, whose scooters are sold by Bird, Lime, and others. People assume Segway acquired Ninebot. He corrects them: No, no, no. Ninebot acquired Segway. Segway had a $3,500 self-balancing device and had not yet applied for patents in China. Ninebot copied it. Then it iterated faster, got in front of customers, and learned what they wanted. Its version came out three times better and three times cheaper, and it sold far more. Then Ninebot turned around and bought the patents. Tom's takeaway is blunt: China builds, tests with the market, and iterates, and nobody there cares if the first design was bad. If you scale sooner, you win. That lesson now shapes his own subscription e-bike company, which he runs from Redwood City. That story is from. We 3D printed a complete payload in 2017. It was in space only five minutes, but even that makes a difference. Satellites are built with aluminum. Composites are lighter, and in space every gram is expensive. Dr. Shrimathi Kaisan, founder and CEO, Space Kids India. A woman looked after by a specialist obstetrician has an 80% chance of a cesarean. Looked after by a low-cost midwife only 20% of the time. You can pay less and get better outcomes than paying more and getting less. Saul Kornick, CEO and founder, Cana Health. A six-month deadline from a Manhattan Bitcoin pioneer. Peter Gillardy Mickelson has just come out of the Ron Paul campaign, hungry for the next chapter of the libertarian movement. His boss, Nick Spanos, is founding the New York City Bitcoin Center in 2013. Peter is in his first semester at Copenhagen Business School when the phone rings. Nick says, drop everything you're doing for six months and read the white paper. As Peter jokes, when a Manhattanite gives you a six-month timeline, it is complicated. He has no tech background. He works through the ten-page document paper by paper, learning the core concepts and then the technology. Thirteen years later, he is a co-founder of Dial, building a way to call a crypto wallet like a phone number, plus a Nordic Blockchain Association and a Danish Bitcoin political initiative. That story is from my audience's menopausal women between 40 and 65. They don't look at me and say, "I want Kim's body," so I deliberately changed my body shape. I have to have the body that women my age will look at and say, "Yeah, I want to look like her." I train three zero minutes and never feel destroyed. Kim Constable, founder, The Sculpted Vegan. We patented everything for an extraordinarily simple reason: if we don't, somebody else patents it and stops you from doing it. So we patent it, then license it for free into the chain, open source. We know how that game is played, and we're not joining in. Founder, QPQ AG, the startup that was the only place to buy beer online. In the US, a 3-tier law forces a brewery to sell to a distributor, who sells to a liquor store, who sells to you. Fresh from $1 billion of beer deals at AB InBev, sees a loophole. His startup, Tapum, layers in every license needed to reach people at home. Brands send product, build a website, and Tapum ships it with no middlemen. Then COVID hits. Bars close, breweries empty out. We were the only place you could buy beer online at scale like that. Every craft brand wants in. The company lands on the Inc. 5000 at number 108, 2 years running. Then the tide turns. Craft beer collapses, and online alcohol sales fall from about 5% to 3.5%. Jason still sells to a strong acquirer in 2023, then starts a fund. That story is from We as media got our relationship with audiences on digital completely wrong from the very beginning because somehow we made it available to everybody. We made it free and started monetizing it via display. Dmitry Shishkin, CEO, Ringgear. We started as Google Analytics for the physical world, but the reality was that a lot of retailers didn't know what to do with the data, and unlike a website, it's hard to A/B test a store. You actually have to change shelves. It's easier to change electrons than atoms. Greg Tanaka, CEO and founder, Percolata. The fraud fighter who left Google after his father's cancer. Auggie Nikolic spends 13 years at Google, leading the AdWords risk engine team that hunts fraudsters on a $100 billion ad network. By his account, the team cuts fraud and abuse rates by over 100-fold. It is a thankless job. If you do your job, nobody notices. Then his father goes through a prolonged cancer battle, and Auggie becomes a primary caregiver. He watches the patient odyssey up close and wants impact and meaning. He joins an early cancer detection company, then co-founds a precision medicine startup that Apple later acquires. Just before that deal closes, he starts Lind, a clinical research operations platform. He sees the same pattern as in fraud: finding the needle in the haystack. Now to match every patient to every study. That story is from: If you want to bake a pizza at home, you throw it in your oven. You want to bake 20,000 pizzas at a time, you need a massive industrial oven. But the pizza's the same. That's what scaling up our factory means. Scott Wharton, CEO, Tandem PV. Today it feels like we're on a freeway called the AI Freeway. Everybody wants to drive a car, but there's no dealership. Everybody's only selling the parts, and you assemble the car yourself. It's wobbly and wonky because you're not a mechanic. We're selling the car. Daniele Bernardi, CEO and co-founder, Toolhouse. The horse manure crisis that explains data center cooling. Herb Xian has 2 thermal engineering degrees, an exit from a company that owned downtown heating and cooling systems in 11 cities, and a theory about why the data center industry is stuck. In 1894, he says, the London Times warned that unless something was done, London would be under 9 feet of horse manure in 50 years. A global conference in New York in 1896 failed to solve it. Meanwhile, Henry Ford of Michigan was thinking about the horse from a clean sheet of paper. The last horse-drawn trolley in Manhattan retired in 1913. Herb sees data centers the same way: fans blowing air across searing chips is the horse, and immersion cooling is the car. He could have retired, but calls this too juicy an opportunity. That story is from: A cruise ship owner was adamant about no casinos, and his team said we need casinos on board. You can't decide that internally because the politics and emotions are too high. We did the research. Turns out you shouldn't have casinos on that brand. Rebecca Brooks, founder and CEO, Alter Agents. EEG is electricity and amyloid protein is liquid. It makes no sense to say we're measuring amyloid without a blood sample. And yet our technology measures amyloid with the same precision as a spinal tap. James Hammond, Founder and CEO, Vistem Labs. 2 years of rejection, then a pandemic proved him right. Yaseen Benally and his co-founder want to let patients book a doctor online in a couple of clicks. Nobody in the Gulf wants it. For 2 years, they talk to every healthcare provider in the region, educating a market that does not know it needs them. Rejection, misunderstanding, patience. Then in January 2020, the team hears about a coming pandemic and asks a simple question: What happens if lockdown comes? People can book, but they cannot see a doctor. So they build telehealth. In 2 months, we went from a company that doesn't have telehealth to the largest telehealth provider in the region. Overnight, the company goes remote, signs hundreds of doctors, and jumps from a few dozen thousand dollars a month to more than $3 million a year. The 2 years of patience had paid off. That story is from— A mattress is like bread. If I give you and your friend the same recipe with the same ingredients, You'll most likely get a different bread. I want the exact same product in the hands of every customer, so we make our own foam in one plant in Montreal. Jeremiah Curvers, CEO, Polysleep. Unless an intervention slows your aging by more than three years, you should not use this clock at face value. If the clock says you de-aged by two years, but the error range is three, that too is just noise. Nikhil Yadala. Every vehicle is connected to our IoT system, and the batteries too, so good luck trying to get away with a Max vehicle or a Max battery. Co-founder and CEO, Max. Why donate when you can invest? That money you might spend gambling or sports betting, put it toward a concept, a community that you support. Co-founder and Chief Evangelist Officer, It's not the medium that's dying. Borders died, but I just saw a new Barnes& Noble. I believe there will always be a place for books, even if it's just the coffee table book you never actually read. Founder, Bookblaster, Huluku Labs. Membership site is not actually a niche. It's a positioning. A niche would be pregnant women over 40 who want to get fit. A membership site is a delivery vehicle for your value. Founder, MemberFix and MemberHost. Tampax paid for a lot of consulting and launched a cup. I tried it. It was very large, it didn't work for most anatomies, and then they wrapped it in plastic packaging, which tells me they didn't know their consumer. CEO and co-founder, Salt. Financial literacy is just PDFs, and that hasn't moved the needle. We have to build a business-as-usual product and process that actually moves it. helping both consumers and lenders. Founder and CEO, My Home Pathway. I pivoted the business almost 2 years ago to the day, February 1st, 2023. I was not happy with our growth or our moat. The first time I played with ChatGPT Plus, I thought, okay, this is the new accelerant for careers. CEO, Section. A Fortune 50 executive told me, If 10,000 people care about our company's AquaScore, then we have to care about our AquaScore. That's when I realized the power of data to the people. Transparency is the new currency. Dal Levant, founder and CEO, AquaGenuity. When I did a time-in-motion study on that clinic, physicians were only spending about 30% of their time diagnosing and treating patients. The other 70% was clerical work that had nothing to do with their medical license. James Bates, founder and CEO, Advynel Medical. Capitalism is self-correcting. Things may work for a while, and then they don't. And then something else takes over. GE didn't adapt fast enough to the changes that were going on in the world. We don't have a GE iPhone. Ari Baum, founder and CEO, CFP, Endurance Wealth Partners. Over 6 years, through natural selection only, we developed a new genetic line of locusts that can be fed with dry feed almost the same as The cost is about 3% of fresh grass, so we will cut the feed cost by 97%. Dror Tamir, founder, Holy Locust. We're the opposite of greenwashing. When a member talks about what they're doing, we've got their back because we certify every single year that anyone who has this logo is doing what they say they're doing. Kate Williams, CEO, 1% for the Planet. In our model, we don't have to waste any money looking for gold because we turn the entire community into a live heat map of where the good gold is. Finding gold is actually a profitable endeavor for us. Co-founder and president, Mwamba. We spend 4 or 5 hours with someone. We call it a clarity day. I can't tell you how many patients I see who say their doctor never even did a physical exam. Founder, orthopedic surgeon, Victory in Motion. Reusability is the highest form of sustainability. It's very counterintuitive because if you're in a business to sell more stuff, It doesn't really make sense off the bat. Once you think about it, it actually makes a ton of sense. Co-founder and CEO, PA Thay. All the hottest businesses are doing AI and platforms, and it's basically all electrons going back and forth. We literally decided to innovate a product that has been part of humanity for 8,000 years. It's a reminder that not every innovation is technological. Co-founder and Chief Sustainability Officer, Beyond a certain scale, companies don't want additional traffic. They already have millions of people going to their website. What they want is to control the way AI is describing them. A lot of the time, it's a vibe check with the executives. CEO and founder, ISO. Chapter 7: People. Hiring, firing, co-founders, culture, delegation. If you don't know how you do what you do, your skills will die with you. Good players become coaches, but if they can't explain how they did it, they can't fix anyone. Founder, ex-SWAT sniper team leader, shot IQ, mind IQ. I was telling John to go to church on Sundays in a tuxedo, and by the time it got out to the rest of the team, it was Sarah's in a yellow Miata on Tuesday. How did that get translated? Brian Fikes, founder, Bonsai Marketing. Veterans have a moat: hard work and determination, no nonsense. They don't feel entitled. If I have a really hard day and feel lonely, I'm going to lean into the mission and lean into my team. Kevin A. Damoa, founder and CEO, Glid. We called it impossible because nobody believed what we were attempting could be done. It's technically very challenging, and the name works really well for recruiting. The best engineers want to build something that others say cannot be done. Oliver Gunasekara, CEO, Impossible Metals, YCW22. When the headcount was like 10,000, he still wanted to see every pixel before it went out on Android and every pixel before it went out on iOS, keeping tabs on exactly who was doing what throughout the whole company. Just scaling somehow by sheer force of cognitive giftedness? People say they don't want to hire the engineer unless they've survived 3 years at SpaceX. 3 years at SpaceX is basically the equivalent of what a really good technical degree might have been 50 years ago. It's evidence that you can actually do something. People rush towards complexity. I think the people who really understand a problem can make it simpler. So we look for clarity of thought more than anything else. Jay Dewani, founder and CEO, Lemurian Labs. We have a private equity backer and COVID hits and they're like, fire everyone, protect your balance sheet. We were like, no, let's live by the values of the business. We're not going to lay anyone off. We'll defer some compensation, but we're going to keep it there. Bjorn Reynolds, founder, CEO, and Chief Guardian, Safeguard Global. The sales profile everyone got wrong. Ask a recruiter what a great salesperson looks like, and you hear the same words: charisma, personality, a connector. Barb Hyman's company, Sepia.ai, decided to stop guessing and let performance data answer. Her team plugged into sales results and time in role, then looked at who actually hit their numbers. The results surprised even the clients. Actually, the true profile of success for sales is not extroverts. It's introverts. Her explanation is blunt: the introvert is laser-focused on the number and is not worried about the team lunch. She calls it holding a mirror up to the humans. What leaders believed was success turned out not to be, and the data showed it. For Hyman, a former lawyer and strategy consultant turned HR executive, the lesson is bigger than sales: we are very sure our gut is right, and very often it is not. That story is from Steve invited about 20 people to his house in Palo Alto and showed them Think Different in his lounge room. They were the people who would help him build the company. After those few seconds of black-and-white footage, they had a reason to believe in Apple, a reason to stay. Cameron Craig, Chief Executive Officer, a signature story. Every day we have a daily war room at 9 a.m. Everyone gets one goal for the day. If 3 people don't manage to achieve their goal, then each of us has to do 60 push-ups. Magnus Mueller, founder, browser use YCW25. People who get promoted tend to be good at execution under the old terms. Somebody who could be a forklift driver becomes a manager, becomes a vice president, and now is charged with making decisions about technology they don't have the capacity to understand. Russell Sean Languedoc, 5x CEO, founder, AI for EBITDA, Outforce.ai. Dan Schulman at PayPal found a large percentage of his employees were barely getting by, even at market pay. He put in practices that weren't expensive in the context of PayPal, and people were more productive and turnover went down. Partner, Quantum Advantage Capital, Foundry. I never hire for skills. I only hire for personality. We look for people who are empathic, sociable, people pleasers, And then we train everything else. Flora Wapples, founder, MD, Restore Medical Spa. About 50% of applicants to engineering interviews are fraudulent. They're not real people. They're using fake identities, or they're North Korean actors. Ofer Samson, founder and CEO, Ezra AI Labs. I asked everyone to take a temporary pay cut. I thought for sure everyone would quit. No one quit. In fact, One gentleman came to me and said, Jeff, are you sure you took enough? Jeffrey Caney, founder and CEO, Caney Aerospace. The salary we paid Martin to be a pediatric surgeon, we discovered he had been quietly giving away to everybody else. He was saying, this is money for the nurses on behalf of Bethany Kids. Peter Lublink, CEO, Bethany Kids. 9 reps quit in 3 months. He stayed. Johnny Page, fresh out of college, is a happy customer of a security software company called Silvertrack when he calls the founder with an idea and gets invited to California. The company turns out to be tiny. The founder offers him a straight commission job, 35% of every deal for as long as the client stays subscribed, and hires 10 people on the same terms. Page sits at his parents' kitchen table and tells them he is quitting his main job for it. They were like, no, don't do that, it's too much risk. 3 months later, the other 9 reps are gone. He stays, builds systems, and And after two and a half years, a book of business bigger than the company itself. Seven years later, it sells to private equity in an eight-figure exit, and he is not on the cap table. That story is from these top leaders often believe because I reached this level, I'm the expert. I don't need anyone telling me anything. That's why they operate in silos and miss that their colleagues have perspectives that could be extremely beneficial. Charlie Lang, CEO, coach, and founder, Progress U. I can run a hospital, but it doesn't mean I can do brain surgery. I hire the greatest people. I don't do any lighting. I don't do any of the editing. I have never listened to a podcast in my life, not even my own. Kevin Halliday, podcast host, president, Shed Talk, Spindle Stairs and Railings. A players hire A players. B players hire C players. If you've got a B player owner hiring A players, he better get out of the way. Because if he doesn't, the A-players are going to leave. Founder, The Profit Answer Man, Profit Comes First. Letting people go is terrible every time. I had to speak with people I knew I would never let go unless I was forced to. I dropped tears. I don't think I'm ever going to get used to it. Co-founder and CEO, Space Rock Games. A lot of dev agencies have a couple of senior people and hire lots of juniors. We took the opposite approach. I'm looking more for ability to communicate than even tech skills. I can teach tech skills. We have more advanced degrees in English among us than technical degrees. Frank Wiles, founder, Revsys. You can become a better BS sniffer. Almost all CVs are inflated, and people are very good at selling themselves, but then they underperform in the roles you put them in. We hired a CTO who was literally piggybacking on another company's success. Managing Partner, Elkridge Advisors. You could name 20 things you admire in the best founders and try to find somebody who scores as high as possible on all 20. Or you could pick the 2 that matter most, make sure they're a 10 out of 10 on those, and be okay with some 7 out of 10s on the rest. Founder, Active Impact Investments. We have 8 full-time employees and we are hiring. Anybody who thinks they're going to reduce the employee base may have been over-bloated from the period when AI was not available. Founder and CIO, Tetra Noodle Technologies. The New Hire Who Looked Like the Interview But Wasn't. A software engineer aces every round. Multiple interviews, a code test, a spotless resume, a LinkedIn profile with 500+ connections built up over months. He is hired, onboarded, and paid into a real bank account. Then, on day one, Andrew McLeod says, a different person shows up. This is the playbook of North Korean operators, he explains, who use deepfakes and BetterVoice AI to land remote jobs at tech companies and gain access to data. You'll actually see a different person show up to work on the first day. The company skipped one step: verifying identity. Andrew's tricks for catching it are small. Ask them to put a hand in front of their face. Change your name mid-interview and see whether they notice. That story is from People Want to Work with People Who Feel Like Friends. If we take away the friendship values, sharing the stories of our lives, laughing together, creating inside jokes, we actually impede business. Barbara Ann Michaels, Jester of the Peace, founder, Humorville. When we do an all-hands, I spend significant parts of it talking about where I failed and how I've screwed up. Up. That normalizes it for other people. If I want them to take chances, they're going to fail, and that's totally cool. Matt Tate, CEO, Decimal. If I put half the people out of work, who are the people buying the products we're trying to market? This is the Henry Ford problem. He said, I want to pay my workers enough that they can afford to buy a car from me. Felix Velarde, founder, author of Scale at Speed 2Y3X. Doctors start practicing with half a million dollars in student We're trained the opposite of entrepreneurs: do no harm, be cautious. There's no business education in medicine. Joseph Antown, Chairman and CEO, El Nutra. I see the opposite mistake far more often. We bring in a commercial leader who is nowhere near sophisticated enough for the technology, and they stifle the company with process or overselling or misrepresenting the technology. Angus Blair, General Partner. One qualification I look for in a founder is the ability to hire and fire for the right price. When you're a small apparel company, you're not getting the best employees. You have to overpay for people. Founder and Managing Partner, Synthesis Ventures. The idea of getting a good job at a good company at 22 with no experience, that's over unless you're a genius. AI has taken the analyst roles, the sales development representative roles, the social media babysitter roles, that's all gone. AI strategy consultant, co-founder, BIG. It's not that people don't want to come to work, it's that the way they're managed destroys their motivation at the core. They've been systematically beaten down by these big enterprises, chained to their desks. Founder and CEO, Demand Metric Commercial Excellence Consortium. A 100% turnover team that fixed one thing. A West Coast company Brian Hughes worked with had a brutal problem: over 100% turnover among its client-facing staff. There were outside issues too, but the leaders did something unusual. They put the employee relationship ahead of even the customer relationship. They followed the program and asked what they needed to do to improve life for their people. It was slow, and Hughes is careful to say there is a trail-to-change culture. But within about 18 months, that division went from the one bleeding talent to one of the highest performing in its larger organization and the fastest growing. Hugh's explanation is simple. They solved for the one thing that was really holding them back the whole time. No new customers, no new product, just a place worth staying. That story is from— we don't have a sales team that hands off to an implementation team, Then to customer success. A squad with all 3 lives with that client for as long as the client lives with us. Sales cannot promise something customer success cannot deliver. Co-CEO and Board Director, Okadok. Chapter 8: Head Game. Discipline, Ego, Fear, Routines, How They Think. Humans have many gifts, but prophecy is not among them. I call it future nihilism. If your DCF model were completely worthless and your out-year predictions meant absolutely nothing, how would that change your investing behavior? Dan Rasmussen, partner and founder, Verdad Advisors. From poker champion to psychotic break in 8 months. Ray first wins a World Series of Poker event in 2006, makes fortunes as a founder, and sits on the board of Full Tilt Poker. Then the Department of Justice sues the company. The charges look false, and he has legal opinions saying the business is legal. But what got uncovered is real fraud by 2 officers, unknown to the non-executive board members. By then he has vouched for the company, they sue him for more money than he has, and he fights with his co-founders and his wife. After 8 months of pressure, I snapped. I broke. A psychotic episode becomes a big reset, and the start of a 15-year journey of healing and self-discovery. That story is from I'm a five to seven year guy. When you get to the eight year mark, it's a lot of spreadsheets and HR issues, and you get sucked out of the beauty and the creative stuff. I like to build and create. Jim Donnelly, co-founder and CEO, Humanot Health. The man who climbed Everest twice could not resist fries. Nirayal sits down to a first lunch with a new friend he is deeply impressed by. The man has climbed Mount Everest twice. He trains Fortune 500 companies. He is the epitome of willpower, determination, and grit. Then Nir's plate arrives— steak frites dusted with truffle— and the whole restaurant can smell it. The minute it hits the table, the Everest climber reaches across. Oh my gosh, truffle fries! I love those. I can't resist. Nir sees this everywhere: the person amazing at business and terrible with family, the athlete who cannot manage money, His conclusion, after five years of research for his third book, is that people hold empowering beliefs in one area of life that never carry over to another. That story is from If You Don't Swing, You Automatically Lose. I don't even need to look at the financials. One kid is born into money; daddy gave him fifty million. Another guy takes fifty million swings to make his first million. This is the journey of the entrepreneur. David Shadpur, founder and CEO, Social Native, offered $100 million in month one. They said no. Jay Samit sits on the board of a startup 30 days old. A buyer offers $100 million. The founders own no house, no car, nothing. They turn it down for ego. Jay, who says he has raised his voice once in his life, loses his temper in the boardroom. His warning: The buyer has a list of companies in your field, and you are number one, but whoever they buy wins. The train leaves without them. Years earlier, Jay watched his own eBay founder stock jump from $15 to $615 a share in the first month. He sold it all. Pigs get fat, hogs get slaughtered. His rule for founders? Take the cash off the table, learn to play again, and have another idea. That story is from— They say luck, and I say community is the 10% luck that tips the 90 inches your favor. Your community becomes your currency and creates luck for you. Every opportunity I've gotten is through the community. Lloyd Lobo, co-founder and author, boast. AI in traction? The father at 19 who read textbooks on the assembly line? At 19, Joe Chura learns he is going to be a father. He is sleeping in a hammock in a friend's apartment and, in his words, couldn't even take care of myself. He has watched his own father fall apart after a divorce, and he sees the same road opening under his feet. So he takes a job at the Chicago assembly plant, building cars. Seat belts, B-pillar scuff plates, one after another. He needs a way out, and the only door is graduate school. So he carries his textbooks to the line and reads in the gaps between cars. Reading 15 seconds in between building these cars, and I did that for 5 years. He graduates, moves into marketing at Ford, discovers digital marketing, and starts an agency in 2011. Seven years later, Dealer Inspire sells to Cars.com with no paycheck for years along the way. That story is from. I used to think agile was crazy and just for software developers. Now, if my schedule isn't working, I rip it up and do a new one. It's the hardest thing in the world to be okay with never having a routine because you're always striving for routine. Juan Luis Betancourt, CEO, Humantelligence. Told there was nothing to be done, he set a 40-minute timer. Tom Lenoble has heard the sentence more than once: There's nothing we can do. He has been given 6 months to live 3 times, with 2 life-threatening illnesses, and the first was terminal. This year he enters his 14th year living with metastatic cancer. In his parents' generation, you gave the doctor your body and God took it back when they finished. Tom refuses that deal. He looks at the clock and gives himself a window. Okay, Tom, you got 40 minutes. Moan, cry, stomp your feet, scream at God, whatever you want to do, and then let's get on with it. When the time is up, he gets curious. If you can stay alive and keep exploring, he says, something else comes along. It does not work for everybody, he admits, but for him it has meant a keynote called Living Fully While Dying that story is from. Being an entrepreneur is the hardest office job in the world, period. Iron becomes steel by going through fire. If I don't think you can weather that storm, then I just can't fund you. Ben Narison, founder and general partner, Tenacity Venture Capital. A sniper shot, a 3-year-old, and 2.7 inches. Joel Turner spends 19 years on a 24-person SWAT team, most of it as sniper team leader. In all that time, the team performs 4 actual hostage rescues. Only one ends with a sniper shot, and it is his. The suspect is holding a 3-year-old girl as a human shield. Joel has to aim 2.7 inches higher than where he wants to hit, so he runs what he calls the mental game. Where does his conscious mind need to be, when, and how? First the aim, then the trigger pressure. Each time, he says, the how is always speech. He talks himself through every step. The round lands, the girl is saved, and the mind-training system he calls Shot IQ stops being opinion and becomes proof. He retires from law enforcement in 2022. That story is from— I have total ADD. When it's really hard and everybody says you're never going to be successful, I'm like, yummy, let's go. Routine is the death of me. Craig Carroll, founder, Certus Insurance. The swimmer who traded identity for law degrees and lost it again. For 20 years, Andrew McConnell is a swimmer. He makes the U.S. national team in open water Then it ends, and he loses his identity. So he stays in school, earns law degrees in the U.S. and at Cambridge, sets nine university records, never practices law, and joins McKinsey. A partner recruits him to launch a product line that hits $24 million in year one. He decides he wants all the upside. He builds a vacation rental marketplace, a financial product, then rented.com, which he sells to private equity in 2022. Then he writes a Stoicism book that becomes a Wall Street Journal bestseller. Readers write that it changed their lives. And he thinks, I could really do a lot more with my life than price vacation homes. That story is from— in farming, a lot of farmers are farmers number one and figure out the business stuff number two. I've learned from very large operations that they are business people number one. Their business just happens to be farming number two. That's a very key shift. Founder and CEO, Continuum Ag. Two engineers and a gaming PC from Fry's win Zuckerberg over. It is 2013. Keith Adams, a Facebook engineer who built HHVM, has just watched a deep neural net crush a computer vision benchmark. With two other engineers, he builds a demo on a gaming PC they bought at Fry's and shows it to Mark Zuckerberg. Zuckerberg is all fired up. He gives them a ton of time and resources to recruit a team, culminating in Yann LeCun, and Facebook AI Research is born. Adams spends the next 3 years getting FAIR off the ground, sharing the long edge of my desk with Zuckerberg, then Slack calls, and he becomes its chief architect before starting the seed fund Pebblebed. The whole thing, he says, began with a demo and a stubborn bet on a hunch. That story is from You can become well known and make money without being famous. It's just more expensive. The more famous you are, the greater likelihood you have of getting lucky. Doors just start opening. Justin Oberman, founder, Oberman and Partners. From Cobra cockpit to a startup in orbit, Kate Van Dam spends ten years flying attack helicopters for the U.S. Marine Corps. Her first deployment is counter piracy off Somalia. The Captain Phillips deployment. Her second is Helmand Province, Afghanistan, in the 2011 fighting season. She flies the Super Cobra— 2 pilots, a cannon, rockets, and Hellfire missiles— mostly escorting troops and hunting roadside bomb placers. She has RPGs shot at her. And she is honest about the weight of it. Every time I would pull a trigger, there was a moment of sheer terror. After she leaves in late 2011, great jobs follow, But no sense of mission. Then, 5 years into a venture arm for the intelligence community, she spots an old contact, Luke, now CEO of Skyfi. 4 months later, she is head of strategy, selling pictures from space. That story is from— Just because you have a high pain tolerance does not mean it always serves you. When I look at what I'm capable of versus my actual rewards, my pain tolerance is also what has held me back. Chris J. Snook, founder and managing partner, Atomic Capital Virtual Family Office. The founder who works 9 months a year on purpose. Sean D'Souza grew up in India and moved to New Zealand, and he runs Psychotactics on one rule: earn 3 times what you need and stop. One-third goes to taxes, one-third to investment, one-third to living. Then the real work begins, which is playing. His team works 12 weeks, then takes a month off. He watches famous peers do the opposite. 2 successful podcasters stand downstairs checking their numbers while he and his wife watch whales pass by upstairs. Another friend with a huge audience tells him he envies him. Shawn's view is that every entrepreneur says they love their work, and it is true, but they've forgotten how to play. His benchmark is a 5-year-old who will tell you to put the phone down. That story is from— What you realize very quickly is that it's not the owner of the business who depends on you. It's his wife, his kids, his employees, his employees' kids. I'm physically responsible for the livelihood of all those people. Founder, Banzai Marketing. Pro basketball, Special Forces, then 2 years of normal. Idris El-Rufai is a 6'2 shooting guard in a sport where that makes you small. He reaches the professional level, then realizes he will never be the best. So he switches gears and joins the French Special Forces. The equivalent of Delta Force or the SAS. He is deployed in 13 countries on extractions and fact-finding missions in teams of 6 to 18 with no supply chain. He loses only 2 people. When he leaves, he builds a company, sells it, and moves to the Middle East. He takes a consulting job. 2 years with BCG to prove I could be doing something normal. Then he builds Fetcher from 0 to 5,000 employees in 6 countries, exits, and joins Glovo in Barcelona. which sells for $2.2 billion. That story is from— they loved being a contrarian because it makes them feel smart, where in their real life they're probably made to feel like an idiot a lot of the time. Host, The Jordan Harbinger Show. From England youth football to pizza delivery to UGC ads. At 8 years old, native Yanko is picked up by Fulham. At 15, he plays for England. At 17, he moves to Cardiff. Then his body starts breaking. A shoulder surgery at 17, another at 18, and at 19, 2 weeks after coming back, a torn MCL. He retires. The kid whose whole identity was football is now a pizza delivery driver with no money, sitting on a sofa wondering what to do with his life. A guru video pops up on YouTube, 50 Minutes on Business Models, and he grabs a pen and paper. He pours basically all his savings into an online course, tries crypto, Amazon FBA, And finally lands in DTC ad creative. Looking back, he calls the injury a gift. It allowed me to put my life back in my hands. That story is from— You've got to believe great things about yourself. And if you believe great things about yourself, the energy of that belief will organize all of the resources and assets around you to accomplish your goals and mission. I know it sounds fuzzy, but it works. Luke Cooper, founding partner, managing director, Latimer Ventures. The Google logo started with a swept dojo mat. Ruth Kedar teaches design at Stanford, and Larry Page and Sergey Brin need a logo for their new company. The connection does not come through campus. It comes through an aikido dojo, where Ruth has trained for decades, and where nobody knows what anyone does outside. While sweeping the mat, a man next to her hears someone say her full name. He is a postdoc at Stanford's Design Research Center, and his colleagues Larry and Sergey are looking for a designer. A few days later, Ruth gets an email from Larry Page. They talk with several designers, and her conversations resonate. She picks a typeface with distinctive letters for G, O, L, and E, and scrambles the primary colors on purpose. The result stays in use for 15 years. As she says, I love it because it's a distillation of really complex ideas into a very small mark. That story is from I'm doing this because I'm a humanitarian first and foremost. Every single day that I bring forward the defeat of aging, which I think I probably do every month, I'm saving 110,000 lives. There's more than 30 World Trade Centers. That's quite easy to get out of bed for. Aubrey de Grey, President and Chief Scientific Officer. Co-founder, L.E.V. Foundation, SENS Research Foundation, held hostage by drunk Russian soldiers over a $150 repair bill. Between the first and second year of law school, Dan King enters the Mongol Rally, a charity race from London to Mongolia in a terrible car. Deep in Siberia, the car dies. Russian soldiers show up and offer to help. They fix it just enough to start, then drive off with it. And still say he owes them five thousand rubles. So they put him in the back of an army truck and haul him to the nearest bank machine. The machine does not work. Dan walks up to a six-foot-four soldier holding an AK-47, looks him in the eye, and says the only Russian he has: "Bat kaput." Even the soldier has to smile. He throws their bags on the ground and drives off, leaving them in the middle of nowhere. To this day, Dan says. It is an outstanding invoice. That story is from. I found I needed to calm myself down in order to compete at my best, so I went from listening to AC/DC to listening to Bob Marley and Frank Sinatra. I actually found that if I fell asleep in the race seat before I went out and competed, I was in the right zone. Cameron Van Den Dungen, CEO, former racing driver. Sleep tight. She matched strangers by looks in a coffee shop. Karen Harris has raised money for a peer support community. She grows it to 30,000 people, but cannot monetize it. So she stretches the cash across 3 years and goes back to the drawing board. She notices people posting things like, Hey, my name's Tom. I live in Bristol. Does anyone want to meet for coffee? Strange, she thinks, but it keeps spreading. She runs an experiment. First, student dinners. Then she walks into a coffee shop chain in Islington and visually matches lonely, good-looking people working on laptops alone, inviting them to dinner. It works. She sells small group shared experiences through Meta ads, starting with Tuesday dinners at 7 PM, which also solves off-peak hours for restaurants. Months later, Storyboard has run over 3,000 events. The sweet spot, she says, is 6 people. That story is from— it was super helpful for me to realize how far I can go Physically, people think that they are limited. If they don't sleep one night, they feel uncomfortable. But I didn't sleep for four nights, and I delivered the stuff to the clients. Alan Gobs, co-founder and managing partner, Adam Capital. A bonfire story sent him hitchhiking south through Central America. It is the pandemic, and Magnus Mueller is stuck in a German university with everything online and a relationship that feels like a dead end. He books a one-way flight to Mexico. One night at a hostel bonfire, people from every country sit around the flames, and a Spanish guy tells how he left his lawyer job to hitchhike the world. Magnus feels it in his heart. It just beats fast. They decide to hitch south together, tents and hammocks on their backs, always south. Every morning, the same fear: Will someone pick us up? Where will we sleep? Then the same answer: The worst case is sleeping next to a gas station. It always ends up well. Months of Central America, then machine learning internships, then the Middle East. Later, he turns that same tolerance for chaos into a startup that raised $17 million. That story is from— I have a tattoo on my neck that says Memento Mori. I'm going to live a life where I minimize regrets instead of maximize regrets, like the default programming our society puts on us. Overweight, broke, unhappy, unfulfilled, divorced. I don't want those things. Nick Hutchison, CEO and founder, Book Thinkers. A podcast goal measured in overheard bar chatter. When Stephen Laddick starts a podcast for his consulting firm, International Solutions Group, he gives his team an odd goal. Most of their work is government related, so he wants to walk into their go-to bar in Washington, D.C. and overhear someone say. Hey, did you hear that on Terms of Reference podcast? The early episodes are, in his words, absolutely horrific. He keeps going. Four years later, the show sounds like NPR, and the goal comes true. Three times it happened. I heard that. There was no way to measure the ripple effect back then, he says. But the credibility and the stealth marketing were real. His advice to anyone hesitating: push go because everyone is terrible at the beginning. That story is from. A lot of folks go into jobs and say, "I'm the best at what I do. Screw this big boss; he doesn't know what he's talking about." But when you remove ego and surrender to the mission, you actually propel through it. Kevin A. Damoa, founder and CEO, Glid. He baptized himself and read one word: redemption. In 2016, a friend tells Kevin Bailey he should be baptized. He asks his wife's uncle, a priest. Who says he will only do it if Kevin is willing to become Catholic. Kevin has no interest in that. So he Googles it, learns you can baptize yourself, and does it in his bathtub. As he rises out of the water, he looks at a cup his wife keeps by the tub, one he has never really noticed. It reads Redemption Brewery. He looks it up: God's plan for the salvation of humanity. Next to it, Three Wise Men Brewing Company. He is holding a cup. The first word I read was redemption. Statistically, he says, it is beyond probability, and it is enough to push him to follow through. He becomes Catholic. That story is from I describe myself as a lazy overachiever. I'm not the guy who runs a five k every day. I need to register for something, and then I'm going to exceed at it. If I don't register, I don't train. Roger T. Dugui, managing partner. Practice leader, CEO, and board services. Boyden, eight lost years, then one thousand strict pull-ups. At eighteen, Alex Wish is one of the top young sailors in North America and a UPenn student chasing the Olympics. By sophomore year, he has burned himself out completely. He leaves school, never graduates, and spends eight years in a battle with severe depression, in and out of hospitals, on disability, without a home. His parents think he has given up. He rebuilds by controlling what he can: sleep, nutrition, exercise, and who he surrounds himself with. That leads to personal training, and training clients leads to business deals and a career in real estate lending. Then, during the pandemic, he sets his own challenge: 1,000 strict pull-ups, 2,000 push-ups, and 3,000 squats in a 24-pound vest in freezing rain. He finishes in 6 hours and 8 minutes and raises $37,000 for veterans' mental health. That pain is a choice, he says, and he will take it over anguish any day. That story is from... I'm never off. I'm never on vacation. When your customers are in pain and reach you, it means you failed to give them a better solution. First I help this person, then I figure out why they had to come to me to get that help. Sean Clark, co-founder, HighLevel. The Peanut Seller in Swaziland Who Stopped Coming. Kashidi Chaudhry lands in Swaziland as a young health economist, placed in the government in the country with the highest HIV prevalence in the world. Every morning on his way to work, he drives past a woman who sells him a newspaper and a packet of peanuts. He pays cash and calls her Marge, the local word for mother. About 30 days later, a young girl is selling him the newspaper instead. He learns the woman has just died of HIV. I had no idea. It is the first time that real-life stories become more important to him than spreadsheets. He learns that around 22% of the population are orphans, pushes the World Food Program and UNAIDS to fund shelter homes, and later founds Jivalgo to help grantmakers spend better. That story is from. I wanted to train myself to be comfortable with getting rejected. If you're getting rejected, You're stretching yourself. And when you're stretching yourself, you can achieve those asymmetrical outcomes. Arvind Veluvalli, CEO and co-founder, Fresco YCF24. He fell on the Autobahn and had one tool left: breath. Derry Llewellyn Davies is on Denali, on a stretch climbers call the Autobahn, where if you slip, you die. He slips. He falls. Panic takes over, and he does not feel calm for a second. Somehow he digs in his crampons and self-arrests with the ice axes. Then he is pressed against the ice face, thinking he is going to die. I just needed to breathe. He holds the axe, keeps his face against the ice, and controls the breath until the panic passes. Years later, he says the lesson works in a board meeting, in an argument, or with a toddler having a tantrum. He once thought breathwork was woo-woo; now he calls it the thing that keeps him going. That story is from. The most important lesson that I learned about myself was that I do not crack under pressure. I didn't know this. And turns out that is all you need in order to run a startup. Sharman Ali, serial entrepreneur, author, angel investor, safe. A 10% tax killed his empire, so he invented a sauna gym. Stephen Smith has been a franchisor since 1996, building Planet Beach tanning salons into a national brand. Then the financial crisis hits in 2008. In 2010, the government adds a 10% federal excise tax on tanning services, and the industry never recovers. The skin cancer problem was always its Achilles heel. Smith, a former football player and competitive bodybuilder who once ran 3 Gold's Gyms, faces a choice. There's only one way out. You have to invent your way out of it, he says. He combines his love of fitness with infrared heat and builds a 3-person sauna workout studio, the magic number he learned as a personal trainer. HOTDORX opens its first location in 2017 with a goal of 500 inches 5 years. COVID costs a year. Today it has more than 840. That story is from: Having many ideas has been mostly a bad habit for me. In order to succeed, you need to do one thing and do it right. I must try something new every year, And I don't think it's a good thing. Gabriel Jarosan, managing partner, Lobster Capital. The professor who wrote NumPy instead of chasing tenure? Travis Oliphant is a professor who knows exactly what earns tenure, and writing a numerical library is not on the list. But he sees a gap. Scientists are scattered, each using different tools, and the world needs someone to unify them in Python. It looks like I am one of a handful of people in the world right now that could do it. He says, and not because of unique skill. It is the connections, the awareness, the time, and the naïveté. He writes NumPy in 2005. He later helps create Anaconda and the nonprofit NumFocus. Had someone told him the goal was 25% of scientists or 40 million Anaconda users, he says he would have been too scared to start. Instead, he simply acts. Today, he pushes the opposite of AI centralization. Billions of small, sovereign AIs owned by people. That story is from: As an entrepreneur, instead of first building the electric battery, I go, let's put a rocket on the moon. Then I learned that to put a rocket on the moon, I probably need to solve 8 other very profitable things first. That's been a big challenge for me. Sean Pinnock, CEO, Avalon. One phone call erased 60% of the company. Jeff Caney builds an aerospace manufacturing company on his own money, with no outside equity. His team knows 93% of income comes from one multi-billion-dollar customer, and it treats them great. Then comes one phone call. Most of that business disappears. Literally one day. Jeff asks everyone for a temporary pay cut. He is sure people will quit. Nobody does. One employee even asks if he took enough. He sketches a simple plan and tells Tells the team exactly what is happening. A friend tells him never to close his office door, or people will assume he is talking to the bank about bankruptcy. If he needs to talk to the banker, he drives away in his car. The company wins customers, restores pay within about six months, and comes out stronger. His rule: never waste a good emergency. That story is from. If you were to approach me and say, "I'm doing this one thing." My screen is not going to be full of all these different distractions. I do it really well, and that would lead to a much better vision of you. Andrew Warner, CEO and host, Mixergy. He wrote one novel and built Israel's biggest publisher. 13 years ago, Yehuda Niv is an electronics engineering student who publishes his first book, a novel with a very long story and lots of detail. Then he sees how the industry actually works and decides the publishing process. Is completely broken. So he opens his own house and names it, not very cleverly, Kniv Publishing. It is fully bootstrapped and it grows into the largest publishing house in Israel with more than 7,000 authors. About 5 years ago, he finishes building his management team and gets his life back. He travels, angel invests, and meets tech founders working on AI. That is when he realizes this technology will revolutionize publishing. So he starts again with spines. That story is from entrepreneurship is you write down all the things you need to do to succeed every day, and then you do them all. The problem is most people do 90% of them and think it's good enough. You start with the ones you really don't want to do, and then you get to run downhill the whole way. Casey Hanmer, founder Terraform Industries. Ten times he almost died, then he ran. In 2009. Chad Weller drives drunk into a 50-foot brick wall. He survives, barely. Lying in recovery, he sits down and counts every time he has almost died. 7. Then he finds 3 more. 10. For years, the former Miami Beach model, nicknamed the Mayor of South Beach, has hidden depression behind parties, pills and alcohol, and has attempted suicide 3 times. Facing prison time over a DUI, He gets scared enough to change. In 2010, he discovers ultramarathons. Years later, running 100 miles from Key Largo to Key West in 96-degree heat, he suffers kidney failure and passes blood for hours. Don't stop becomes his mindset. He finishes in 29 hours and 49 minutes. That story is from— If you're not solving new problems, you're not really creating value. If you're trying to protect downside, Your gains are limited. But if you're focused on asymmetric upside, you have to do things differently. Jay Dewani, founder and CEO, Lemurian Labs. The man who knew when his chapter was done. In 2016, Will Katie opens Reddit's Los Angeles office, a small outpost testing whether the site matters to Hollywood. It does. He goes on to build Karma Lab, Reddit's internal creative agency. Over eight and a half years, he learns that his award-winning. Music-school ego is the wrong tool for a chaotic community. As a creative, your job is to get out of the way, he says. Then, one day, the work feels complete. We're not really taught how to end things, he says. We're taught how to start things. He leaves feeling only gratitude. Now he and his wife, who is his cofounder, are building a business and raising a 1-year-old at the same time. We're absolutely insane to be doing, he laughs. That story is from... As a VC, I have many bullets in the chamber. A typical fund might have 30 companies. As a founder, you get one. That is your one shot, and a lot of it is out of your control. Venture partner, Defy VC. A CEO coach who quit a job to learn not to burn out. Charlie Lang is 2 years into his second corporate role when he burns out completely. He quits. He has a new job lined up, but a month in between, And he uses it to ask what just happened and how to make sure it never happens again. The answer is uncomfortable. He cannot prevent hard things from happening. What he can change is how he processes them. Up to then, he took everything personally— mistakes, failures, other people's calls. Don't take it personally, take it seriously. That reframe, learned the hard way, now shapes how he coaches top CEOs across Asia. He recently had the same conversation with his own daughter. He says it takes time for the shift to settle in. That story is from. There's a type of therapy called EMDR, designed for PTSD folks, but we used it to forward plan the fight. I've never, especially with someone with ADHD, been so calm walking to the ring and seeing this giant in there. Bjorn Reynolds, founder, CEO, and chief guardian, Safeguard Global. The executive who sold a $2.1 billion company and quit. On the outside, Lon Stroschein is crushing it. A farm kid from the Midwest, he has gone from a U.S. senator's office to a bank to 14 years at a public company where he leads mergers and acquisitions. He has the title, the money, the house, the marriage. But every quarter or so, he arrives at the office first, sits alone, and asks, Is this it? Then he feels guilty for asking. The itch starts in late 2019. In February 2022, his company sells in a $2.1 billion deal. At 46, he reframes it. He isn't quitting; he's finishing. His work is done. He leaves with no resume and no plan, writes his story on LinkedIn, and his inbox explodes. Within a year, he has a company, a podcast, And a book called The Trade. That story is from— I think that's upside down. You should start early. It's a habit, and like all habits, you need to integrate it into your life. The people who are the most joyous and content are the ones who have been lifting other people up for a very long time. Peter Samuelson, CEO, author, film producer, and philanthropist, rowkindness.org. Friday he had a job; Monday he didn't. It is September 2008, and Chuck Garcia is at BlackRock when the phone starts ringing. Friends at Lehman Brothers are calling. Stunned. Friday, Chuck, I had a job. On Monday, I didn't. Over one weekend, a firm of 25,000 people discovers it is no longer solvent. Bear Stearns and others start to fall. Chuck, who spent 25 years on Wall Street, calls it a colossal failure of common sense. Smart people took big risks, lost their sanity, and doubled down. The market fell 54%, a drop no expert had predicted at the start of the year. Years later, his lesson is not about tariffs or inflation. He worries about the crisis nobody can see coming. That story is from I asked people in their 40 seconds on Wall Street, "Would you do this career over again?" They were probably making millions of dollars a year. They said. Yeah, I wouldn't do it again. I really took that to heart. Brian Bell, founder and managing partner, Team Ignite Ventures. A Craigslist wetsuit and a lake in the 40s. Ryan Joswick has run marathons since 2002 when a buddy pitches him an Ironman. His first thought? I'm going to drown. They tell everyone they are doing it, then his wife suggests a small sprint triathlon first. He buys a wetsuit off Craigslist in a mall parking lot. Too tight, never worn. The lake near Seattle is in the 40 seconds. He swims flat out, thinking the faster he goes, the sooner it's over. Barely 100 meters in, he is out of air and the suit is suffocating him. He flips to backstroke, swallowing water, kayakers circling. Across the lake he spots his friend Eric, also terrified, also backstroking, in the wrong direction. It was the longest 11 minutes of my life. He hires a swim coach, trains for a year, and crosses the Ironman finish line in Penticton, Canada, in under 12 hours. That story is from Action Creates Information. By taking action and moving fast, even if you might be going slightly in the wrong direction, you'll learn things from that. You can't think your way to the start of being successful. Connor Brennan Burke, founder, Hyperspell. 4 days fasting alone, and the chipmunks did not care. About 9 years ago, Tasha Wall does a vision quest. 10 days off the grid, 4 of them completely alone, fasting, with no tent. Just water, a tarp, and a journal. She sits looking out at the birds and the chipmunks and everyone around her. Trump is president at the time, and the thought lands. They don't know who Trump is. They don't care. The animals are not thinking about policy. They are just doing what they need to do. It becomes, she says, an enlightening moment. The things we treat as huge—politics, tariffs, how much money we made—are not what any of us will think about at the end. What will matter is relationships, people, love and generosity, a shift in consciousness toward what is actually important. That story is from. This idea of deciding what kind of entrepreneur you want to be and then just going and being that was very false for me. For me, in entrepreneurship, it pulls you in the direction that will work for you. Otherwise, you'll fail. Matthew Tsai, CEO, ImprovMX. From Goldman to a hundred grand and a bitter lesson. Rich Weidel left Goldman Sachs for Florida, where he worked for a real estate developer with a billion-dollar portfolio. He was offered an LP stake with a 15% return, while the GP side made 50. He wanted the GP deal. His boss said no. You haven't spent 20 years having to make payroll. You don't sign the personal guarantees. Weidl stewed for a couple of days, then looked in the mirror. He was trying to short-circuit the risk. With about $100,000 saved, he went off alone, spent 9 months working every single day to get traction, then bought shopping centers. His dad later called to shut down Princeton Mortgage, with 3 people. Weidl jumped in, and by 2021 it was the 2nd-fastest-growing company in America. That story is from. People understand compounding interest. They need to understand the compounding impact of sustainable marketing over a long period of time. In 2020, it was probably two million, then four, then six, and now it's ten to fifteen million. Chris Walker, CEO, Refine Labs. The Tesla that never drove into a wall. Michael Schermer has driven a Tesla since 2015. This is his third. Since he bought the first, people have warned him that because the car is online, a criminal could take over his steering wheel and drive it into a wall. Worse, a terrorist group could seize thousands of Teslas on the 405 freeway and cause a mass-casualty event. Airplanes are online too, he hears, and could fall out of the sky. For 10 years the warnings keep coming, and for 10 years nothing happens. How come it hasn't happened? Schirmer asks. There are terrorists who would love to do it, he says, but they can't. If a bunch of Teslas did start mowing down pedestrians, regulators would swoop in on the company within days. His rule for AI is the same: go for it, and fix problems as they arise. That story is from— There's not a week that goes by that I don't think, should I have just kept the boat, gone back 6 months later, polished it myself and gone sailing, instead of continuing this journey a second time? It's very rewarding, and some days just super hard. Emmanuel Lavoie, CEO, Jetstream. The partner who pays to build your alpha. Jim Weldon makes a pile of money from exits and decides the worst move is to invest it all again. He tries writing checks. I invest in knuckleheads that are like myself, he says, and he loses money. So he changes the play. He finds a company in his network with an idea it cannot execute, and it pays him a market development fund. Of $100,000 to $200,000 to build the alpha version. He owns the tech and the IP. They get no shares and no say over direction. At most they get an exclusive, and only if they guarantee at least 7 figures in revenue. His early deals asked for a couple hundred grand, then he realized that was stupid. Sales is the only sustainable way to fund your company. Full stop. That story is from If you take an entrepreneurship degree, the only qualification to get in should be: Did you start a business before? So many people go on these courses and have no chance of developing a company or a product. Douglas Crystal, founder, True Video. The first lesson from golf's golden boy who snapped his spine. Austin is on track to become a professional golfer. Then he swings so hard and so fast that. But as Amber Meixle tells it, the torsion breaks his back in the center and in his neck. He ends up in rehabilitation at the fitness center Amber runs, where she offers meditation and nutrition. She becomes his mentor, then his best friend, and eventually they fall in love. What heals him, she says, is realizing that a golfer did not define who he was as a person. It was just something he did until he didn't do it anymore. Once he accepts that, The mental shift heals the physical form. Today, the two run the Suivera Church together, spending every day side by side. He handles the finance side; she runs the business. That story is from in March 2020. I said to the team, "I want us all to survive this. I'm going to take a 50% cut in my salary." I got 100% opt-in from a team of 100 plus people within the hour. Nile Murphy. Founder and managing partner, Morphosis. A mother of 4 quit failing and lifted instead. Kim Constable wants to earn money from home after her son Jack is born, without leaving her 4 kids. She tries one online business after another and fails for years. She keeps spending money. Her husband despairs. Then she decides to jack it all in and become a vegan bodybuilder. The entrepreneurial spirit kicks in again: Maybe I could package this and sell it online. She builds the Sculpted Vegan into what she calls the world's largest online vegan bodybuilding company. Next comes Sculpted Menopause, and now a software platform called Be Sculpted with a 3-year plan to open studios. Along the way, she lifts a 240-kilo hack squat and, in 12 months, doubles her muscle with no steroids. Then she deliberately changes her body shape for her audience. That story is from Write down your personal definition of success, how much money you want in the bank, and whether there is a version of the company you don't want to work for. You become what you say no to. When you say yes to everything, you burn out. Lloyd Lobo, co-founder, Bose.ai. He quit his own rocket ship to fix baby monitors. Kevin Lavelle's first company, Mizzen and Main, was laughed out of trade shows for making a dress shirt that stretched. It grew into hundreds of millions in revenue. Then he stepped aside, brought in a new CEO, and spent three years building a tech accelerator for nonprofits. But one idea would not leave him. His family's Nanit baby monitor was an app on a phone. I woke up one morning; the app had crashed, and nothing told him it was gone. He bought an old Motorola monitor instead and hacked together several systems to get a device that would alert him if the connection dropped. stopped. Friends and mentors told him that what you can be, you must be. He stepped down and started Harbor, a monitor and a remote night nanny at 5% of the cost. That story is from— I call it the Rule of 72. When an email makes me want to respond right away, I write it, look at it the next day, and rewrite it. Sometimes the email doesn't even go out. Sometimes the best thing to do is nothing. Frank, co-founder and managing partner, The CEO Who Talks About His Daughter in Present Tense. Dmitry Shishkin runs a media group, but the lesson he carries most came from losing his daughter Masha at 21. Years later, he still speaks about her in the present tense. Masha is still very much with me and with my wife every single day and every single second, he says. They don't believe in people disappearing anywhere. She made a lot of podcasts in her time, so he has thought seriously about rebuilding her voice with AI. The snag is practical. You can't just upload a voice to a connected home device. What her death taught him is simple: care much less about small stuff, be in the moment, treat yourself and others with more kindness, and stop delaying things. She had plans too, he says, and then she was gone. That story is from When I asked the gray hair investors what the reason for their success was, they gave a lot of reasons: a great team, a great product. But the last thing they would always say was, "Oh, this was a tailwind." What does tailwind stand for? Luck. Victor Orlovsky, managing partner, R136 Ventures. He wanted his own company. It wiped out his identity. After successfully running a company for someone else, Matt Tite wanted nothing more than to run his own. So he started a restaurant tech company. It felt so cool and sexy. It was also a huge slog. They raised money and talked publicly about everything, and then it failed. He had tied so much of his identity to constant success and to that business that, in his words, it just ripped that away from him. His wife helped him pull the two apart: who he is, who he wants to be, and work. Breaking them apart felt freeing. He started talking publicly about his fears and failures. 4 and a half years ago, he started Decimal, which has since grown profitably to about 80 people. That story is from. Count all your complaints tomorrow, including the ones you tell yourself. You'll end up close to a hundred. Turns out that's what humans are predestined to do because our ancestors worried a lot about the lion behind the tree. Kevin Sures, futurist, keynote speaker, inventor, the CEO who had his identity crisis early. In his late 22s, Derek Wilder's home building company is growing fast, and he is quietly falling apart. There is no affair, no drinking, nothing on the outside that looks like a train wreck. Inside, he says, he is in turmoil. He is a workaholic, and his sense of self rises and falls with every result. Slowly he faces the demons and realizes what he is doing to himself. With or without this business, I am still me. Decades later, in 2022, he sells Hallmark Homes. The buyer's founder dies 3 months after the deal closes, and Derek has to step up as the leader. Selling does not trigger the identity crisis that hits so many founders. He explains why: he already had his. That story is from: We live in a world that has a huge survivorship bias. Now that I'm alive, I can tell stories. If I had died along the way, nobody would know. Balakamalakaran, founder and managing director, Startup Iceland, Iceland Venture Studio. A waterproof passport idea sold 2 a week. Kyle Ewing's passport gets wet, and for the next 10 years customs dings him for it. So he invents waterproof paper and prints waterproof passports. Nobody buys them. His first run is 100,000 sheets, stacked in the basement while his wife tolerates it, and he sells a couple sheets every few days. Then he pivots to restaurants, the military, and sports teams, and he mails free samples to every gym and hotel he can think of. Customers keep finding uses he never imagined. Terra Slate grows from that basement to over $30 million in sales. The kicker, he tells Charles, is that he has promised his wife for 11 years he would sell it and move to Hawaii. That story is from— I'm a musician too, and the parallel is real. I probably spent 2 years on the second half of the second verse of one song. Founders do the same, holding on to the creation with both hands, scared to let it out until it's perfect. Robert Hariri, co-founder, early-stage VC investor, Razy, Deco, Evolution VC Partners. He bought a company right before the Great Recession. In 2008, Andy Harris, a hired-gun CEO backed by private equity, closes his first acquisition, a specialty chemicals business with sites in the US and Europe. The timing is brutal. The Great Recession hits. The business is very sensitive to it, and our sales dropped 60% over the next two years. Instead of retreating, his team builds a plan for the rest of the world and does work in China that becomes a new strength. When the recovery comes, the business is positioned to take off. Within a couple of years, it is well above its pre-crash level and much more profitable. Harris later does over 20 acquisitions for three different firms, leading companies from $120 million to $1.2 billion. Billion in revenue. That story is from— We live in a world of quite a bit of apathy, where someone says, I clicked on a link, so I'm good. I gave a thumbs up to that post, so I've changed the world. But if someone comes for our wallet, we'll just say no. Peter Lublink, CEO, Bethany Kids. She counted people's garbage to catch them lying. Rebecca Brooks trained as an anthropologist, and one cultural anthropology book from the '82s Garbage shaped how she runs research. Investigators visited homes and asked what people bought: how many cigarettes, how much alcohol. Then they took the household garbage back to a lab and counted. The gap between claims and trash was huge. People overstated vegetables. The trash showed no sign of home cooking. It was, she says, a wake-up call. You have to combine methodologies. Today, her firm. Alter Agents, serves Google, Snap, and Nespresso with surveys, focus groups, neuroscience built on DARPA technology, and deep secondary research. Her conclusion is simple: consumers don't tell the truth because sometimes they don't even know why they do what they do. That story is from— You can't be a sane person and be in entrepreneurship because it's so lonely. You're literally looking at your bank account wondering, why am I in this game? An L8 engineer at Microsoft makes something like $700,000 a year, but that's not what I'm after. Michael Yagudaev, co-founder, CreativeFlow.ai. A rocket company born in a basement in Auckland. Angus Blair runs a venture fund out of a 100,000-square-foot building in Auckland, and the building is the whole story. Back in 2006, Peter Beck started Rocket Lab in its basement. Today it is NASDAQ-listed, and Angus still walks visitors past a fragment of an exploded rocket engine embedded in a Another founder, Sean Simpson, got his start in the same building and also took his company public. Angus, a 6'5 former powerlifter with a 282-kilo deadlift, joined the fund 5 years ago because he couldn't find a New Zealand company he wanted to work for, only entrepreneurs he wanted to learn from. Beck and Simpson now sit on his investment committee. About a third of his capital comes from investor migrants who chose New Zealand as home. That story is from. I'm lucky that I don't get stressed that much. The way we appraise reality creates reality. I don't appraise things as stressful. I think, cool, this is exciting, this is a good game. Co-founder, superpower. His dying father's regret launched a grand slam. Deryab John Llewellyn Davies is a big Welsh rugby player when his father falls ill with cancer. Sitting on what turns out to be his deathbed, the man who never said anything remotely emotional holds his son's hand and says, Son, I regret so much in life. 2 days later he is dead, dreams intact and unfulfilled. That is the moment, Derry says, where all the adventures began. He sets himself a global adventures grand slam: the highest mountains on earth, deserts, jungles, the poles, and an Ironman, which he finishes as a poor swimmer who has not ridden a bike since childhood. Years later, COVID takes his inner ear and his balance, and doctors tell him his mountaineering and flying careers are over. His answer is blunt: he is coming back. Now he is training to lead a paralyzed climber on Everest's north face. That story is from— I know there's people who will go, well, they just need a kick up the backside. But people don't see what has led them to that stage. In 20 weeks, we're trying to unravel a lifetime's worth of trauma that's in the background. Cheryl O'Donnell, CEO, Canberra Police Community Youth Club . The Man Who Got Sick Enough to Work 1 Hour. At 23, Ari Meisel is diagnosed with Crohn's disease, a condition the medical profession calls incurable. For 2 years he gets sicker, working 18 hours a day. Stress is wrecking his body, Eventually, he can manage one hour a day at most. So he asks a question that reshapes his life: What would you do if you could only work an hour a day? He builds a system of productivity to deal with the stress and starts biohacking his diet and supplements. Within months, the illness recedes. Eighteen years later, he says he has no pain and takes no medicine, and has helped hundreds of others replicate it. That question becomes less doing his books, his speaking, and the replaceable founder coaching. Now run on a single hour a day. That story is from Founder Future Fit is the ability of a founder to understand what the future of their industry is going to be and build for that future. History is littered with businesses that failed to see it. Think of Blockbuster before Netflix. Ryan Pruitt, Managing Director, Ocean Azul Partners, the agent who talked him out of Last of the Mohicans in 1991. Wayne Baker is playing pro lacrosse in Buffalo and has never acted. Casting people from Last of the Mohicans visit practice, looking for players for a lacrosse scene, and ask, would you like to be a movie star? 2 weeks later he is flying to New York to audition for Magua, then rerouted to North Carolina for Uncas. It comes down to him and Eric Schweig. On the last day, director Michael Mann puts a hand on his shoulder and asks who his agent Wayne has none. They offer him a Mohawk warrior role, but the pay is too low, so he says no. Ten years later, a Vancouver agent tells him, "They really wanted you, but I talked them out of it." He starts acting in 1997. That story is from. I just don't want to manage fifty people. I never want to be Tim Cook or somebody like that. That's never been my goal. I enjoy keeping things small and manageable to my lifestyle as much as any. Frank Wiles, founder, RevZee's. She wrote a book so clients would stop calling. After selling 2 companies, Shannon Byrne Susko retires to raise her 3 kids. Then a Vancouver CEO calls. He watched her sell one company and build and sell another in under 6 years, and he wants whatever that was. She hesitates. He calls again, and again, for months. She finally agrees to coach his leadership It works. He tells two friends, and they tell two friends. Six clients feels like her limit, so she writes a book to give the system away. The goal is that people will stop calling. People call you more. She hires a developer from her last business to build a platform so clients can watch their game on the field every day. Today it has over 25,000 users, 3,000 companies, and more than 200 coaches. That story is from. Every good founder is delusionally optimistic. They're not reasonable people. That doesn't mean that everyone who's delusionally optimistic is a good founder. —John Frankel, founder and partner, FF Venture Capital. She launched a bestseller from a trauma unit bedside? J.J. Virgin is publishing her first New York Times bestseller when her one 6-year-old son is hit by a car and left for dead. She launches the book bedside in the intensive care unit. In the trauma center, the doctor says the family should let him go. He will never survive the airlift or the surgery. Her other son, 15, answers, it sounds like a 0.25% chance he'd make it. Let's take those odds. Years earlier, a mentor had spent 6 months snapping a rubber band on JJ's wrist to break limiting beliefs, and it paid off now. Her son has a brain injury, 13 fractures, and a torn aorta. He wakes from the coma after about three weeks. She sneaks fish oil into his feeding tube. Today, he is a fully functional two-nine-year-old. That story is from. We are so concerned as women. What's the family going to tell me? What's my neighbor going to tell me? We worry about society more than what my heart says. Be true to your heart. It's one life. Live it to the fullest. Doctor Shrimathi Kaysan, founder and CEO, Space Kids India. At 18, the instructor broke his leg and picked her. Kate Williams is 18, on a 30-day trip in the Wyoming mountains where everything goes wrong. Then the lead instructor breaks his leg. There are no cell phones, no satellite phones. A runner group goes for help, and a team carries the instructor up to a pass. The lead instructor looks at Kate and says he wants her to lead the rest of the group and get all the gear up. I'm 18. I don't know what I'm doing out here. Why are you picking me? But she leans in and says yes, and because she knows she is not the most skilled person, she taps everyone else. They stamp out a helicopter pad. As the helicopter pulls off into the sunset, she realizes she loves this: real consequences and organizing a group of people to do a hard thing together. She later becomes CEO of One Percent for the Planet. That story is from. I call inside jokes the hidden language of business. If people have a joke about blue pandas on the moon, every time you mention it, everyone. Is going to start laughing and feel connected. Barbara Ann Michaels, jester of the piece, founder, Humorville. 2 ex-nannies sell a book nobody had read. Nicola Krauss and her college friend Emma worked as nannies at NYU, a purely financial decision. Years later, one idea from Emma turns into a book. Nicola thinks it is terrible. That was the worst job we ever had. But they write it anyway, splitting scenes, and the prologue is never edited again. Publisher support is thin, so Nicola pitches a Sunday-style section writer she meets at a party. The press snowballs. The book hits its 12th printing before its publication date. Then the phone rings. Emma is on her honeymoon when Nicola gets call after call from Hollywood producers. A bidding war breaks out, and in a few hours, Harvey Weinstein, not known for ever taking no for an answer, wins the film rights. The book sells 6 million copies. The advance split between 2 authors, after agents and taxes? We spent all of our money on therapy. That story is from— People become part of hate groups most often because they feel completely isolated. Those groups provide connection and belonging. Treating them like they are past saving is definitely not going to lead to a different outcome than the one we see in the world right now. Katya Stepanov, co-founder, The Inheritance Project. The Financial Advisors Who Got 25% More Productive. Loren Toussaint, who has studied forgiveness for 25 years, runs a small experiment on a group of financial advisors. He doesn't teach them anything about finance, sales, or clients. He only trains them in how to forgive. The training isn't extensive, just a couple of months. The result surprises even him— about a 25% increase in their productivity. His explanation is simple: holding a grudge takes huge energy, and people don't notice how much until they drop it. You're surprised at how much more energy you have for other things. For a founder or leader, he says, the baggage of old betrayals might be the cheapest productivity problem to solve. And the training, he adds, works like any skill— it takes practice. That story is from. In this industry, a lot of people make sales with things they can't back up, and it creates an immense amount of stress. Our company would never pull someone down a road we can't 100% fulfill on. That keeps our stress levels down and the deliverables at 100%. Lee Barcalo, CEO and co-founder, Current Group. Paralyzed on Mount Fuji, negotiating with the universe. Jacob Williams, founder of a quantitative investing firm, decides to run up Mount Fuji after the mountain officially closes. He reaches the empty summit and sprints down the scree. For one second he loses his concentration, goes into a forward roll, and keeps tumbling until a volcanic rock stops him. He is paralyzed. His phone is out of reach. So he starts talking to whoever is listening. Give me a sign. Let me wiggle my little finger. It wiggles. Then the hand, then the arm. An hour later he stands up, striped with cuts that volcanic ash has cauterized. He promises that if he survives, he will try to help people. Years later, after a psychotic break and 28 days in a psychiatric hospital, he writes the book. That story is from I would have been 27 years old when I became CEO. When you have people on your board from Wharton and investors, and you're 27, it's a lesson in humility and a hurry. You think you're really smart. My first counsel to every young entrepreneur is build an ecosystem around you of really smart people who are there to build you. Up, not tear you down. Bob Morris, co-founder and managing partner, Bravery Group. I'm an actual capitalist, and capitalism is not I win, you lose. That's corporatism, and corporatism only exists by corrupting the entire political process. Greg Chu, founder, QPQ AG. In this industry, normally what you like to say is, I've done all the testing, I'm happy to use it on my grandmother. In this particular case, we have to get to the point where we're saying, "I'm happy to use it on my own child." John Ashley, CEO, Octa Surgical. I'm not a lawyer. I have a law degree, but I think like a business guy. I looked at a case last night and saved everybody about 100 grand in fees over two years by saying, "Don't do it." I can see the future. This is exactly what will happen. Robert Stevens, court-appointed receiver. Founder, President, Strongbow Advisors/ Somerset Capital. I'm super optimizing the already optimized. My house is almost perfect. I buy a blind an inch wider. The second I go outside my front door, there are a million more things to optimize. Founder, author of Scale at Speed: 2Y3X. My father said to me when I got to Cornell, if you're the smartest guy in any room, get out. Anyone operating as an island is going to get squashed. I'm a big believer that four eyes are better than two. Jesse Cole, founder and managing partner, Synthesis Ventures. There's never been a less risky time to spend those three years working at a startup, swinging for the fences, so that at age 25 you are infinitely hireable. Who gives a crap what you do between 22 and 25? By 30, you're never even going to put that work on your resume. Jeff Ayers, AI strategy consultant, co-founder. In terms of the tipping point, we're there already. In terms of the technology breakthrough needed, we're way past that. It's just who's going to do the dirty work and scale this aggressively to crowd out ICE engines. It's ultimately a question of execution. Co-founder and CEO, Max. We live in a world where passion essentially becomes our currency. You're not going to beat me on talking about AI chatbots for local businesses. I will talk you under the table. I will be here tomorrow morning talking about the same thing. Cameron Clarkson, founder, Book Blaster, Hulu Labs. I'm just not a very good employee. If I think something is ridiculous or illogical, I can't just look the other way. A lot of being a founder to me is just doing things the way that I want to do them, on my own terms. Vic Dorfman, founder, MemberFix, and member host. You get the siren, you go to wherever you can, then you come back and continue your day like not much has happened. As a human being, you get used to it. You just look at your next step, one step at a time. Otherwise, everything's just a values poster on the wall. It's a touchy-feely presentation, everybody feels good, they walk out, and nothing changes. Or it changes for a month, and then they go back to their old behaviors. Brian Hughes, principal, author of Toxicity, Clear Day Strategies. Just verbalize the emotion. I am angry at this thing. I feel it in my chest. That aligns logic, emotion, and body and releases the pressure. Otherwise, you repress it and it lives in your body as tension. Barrett Brooks, executive coach and writer. Good work, former COO of ConvertKit. Uber just has a filter. The unit economics may not work. It may be a money pit. But the first criterion of whether you work on something is whether it scales. If you can tell from the beginning it doesn't, go do something else. Tom Hegarty, founder, Letgo Car. When people ask me what Bitcoin is going to be, my standard answer is that it's going to be absolutely everything or it's going to be worth nothing. It's too revolutionary to fall in between. Peter Goulartie-Mikkelsen, COO and co-founder, Dial. The weakness of any creator business is that it hinges on one single creator. Take your creator cachet and turn it into more of an empire that doesn't just rely on you. Carl Hughes, owner and CEO, The Podcast Consultant, Rise25, Draft.dev. Business is super easy, I think, until you add people, then it gets a little more complicated. It's money in, money out equals some result. Doug C. Brown, founder and growth partner, CEO Sales Strategies. If I was to design a universe I would not want the amount of suffering that we have in this one, even if it was just computational. There is too much unnecessary suffering in the world, and I'd like to see AI address that problem. CEO and Chief AI Officer, Satalia/WPP. In my experience in the pure service business, you get commoditized, your people become competition, and your customers learn how to do it and don't need to keep paying If you don't satisfy it, you end up with a hamster wheel. Maybe a big hamster wheel, but still a hamster wheel. Gene McCubbin, President, Pop Labs. There are 2 approaches. Either you shrink and die, because once you start shrinking with 10 employees, you're going to die, or you expand and try fighting. Majority of the small companies shrank. We expanded. Yele Okoremi, CEO, Precise Financial Systems. Dr. Andrews says the mark of a great surgeon is knowing when not to operate. It's way more important to know when not to operate than when to operate. Mark Pietropaoli, founder, orthopedic surgeon, Victory in Motion. A successful entrepreneur told me, a business never really fails until the entrepreneur gives up. You can go into bankruptcy, you can close your shop, but it never really fails until you say, okay, I failed, because you can always take another shot at it. Shadi Bakour, co-founder and CEO, Path. Chapter nine: Life outside, family, health, kids, the body, the stuff that keeps you going. I decided to take the entire year off. The first thirty days, I did electronics free. I stopped checking email cold turkey. It was like a cleanse. I got twitchy for a while. Then in February, I took my father to Sicily to see his family, and that was life-changing. Joe Pulizzi, founder, author, The Tilt, Content Entrepreneur Expo founded Content Marketing Institute. A lot of farmers are basically one decision-maker trying to manage everything. That farmer is the CEO, the CFO, the CTO, the operations guy, and might be the veterinarian too. Farming has one of the highest suicide rates of any industry, which is a really sad deal. Mitchell Hora, founder and CEO, Continuum Ag. I've been given 6 months to live 3 times. 2 life-threatening illnesses. The first one was terminal. And this year I'll be in my 14th year living with metastatic cancer. Tom Lenoble, author, coach, CEO, Academy for Coaching Excellence. The racer who napped in the car before every race. Cameron Van Den Dungen races supercars until he retires at 27. For years he believes a driver has to pump himself up before a race, so he blasts AC/DC. Then he attends the Australian Institute of Sport, where sports psychologists teach him about finding an optimal zone, he realizes he naturally runs high on energy. What he needs is to come down. So he swaps AC/DC for Bob Marley and Frank Sinatra. Soon he is doing something stranger. I actually found that if I fell asleep in the race seat before I went out and competed, I was actually in the right zone, he says. His team starts to read the signs: Oh, he's asleep. It's going to be a good race. Years later, he builds a company around sleep. That story is from. I'll go to the gym and I'm breaking down crying at the gym, but I still show up at the gym. It's not that I don't feel it. There are times I break down and I'm sad, but you also have to get up and just move forward. Andrew McConnell, CEO, Alive.ly. I've suffered a cardiac arrest at the age of 33. My doctor was like, you just suffered a minor cardiac arrest. You could have died. And my response was, how minor? Sharman Ali, serial entrepreneur, author, angel investor, safe. I did a lot and tried very hard. I don't feel sorry. I feel happy that I tried so much, pushing the doctors and pushing drug companies to get me drugs. People who tried hard move on fast. People who feel guilty have a harder time. Roy D'Souza, co-founder and CEO, Break BioCorp. The scientists who didn't believe thoughts change your heart. Anna Barnaca is an astrophysicist with a double PhD, a Harvard fellowship, and a body that is telling her to slow down. She cannot. So she builds a dashboard to watch her own heart rate variability in real time. Then comes the experiment she did not expect. She opens a stressful email, and within seconds her heart rate jumps by 20 beats per minute while her HRV falls. She puts on music, lost myself in it, and within 30 seconds the numbers swing back. A scientist who says she would never believe in things like mind-body connection now has hard evidence. The frustration of failing to find a good wearable pushes her to invent one—earbuds that listen to the sounds of the heart below the range of human hearing. That story is from I Started Thinking About Exercise as a Psychological Sport. Founders probably should be in therapy an hour or 2 a day, But that sounds time-consuming and expensive, so I just use my workout as my therapy. Ari Goldberg, founder and managing partner, RNMKR. The most dangerous time in a patient's life, in terms of the risk of them taking their own life, is right after they've left inpatient psychiatric care. And yet it's very rare that people check in. Loren Larson, CEO and co-founder, Videra Health. The data suggests that 75% of patients would participate in a clinical study if it was recommended by their doctor. The idea that people only join to be a professional guinea pig is not accurate. Scott Stout, CEO and co-founder, Medvector. The founder whose smartwatch said he was 7 years older. Sean Pinnock is a former college athlete who goes all in on being successful. For 8 years, he stays up all night writing code and running startups, and it works. But when he straps on a Whoop, the data is brutal. It was about 7 years older, and I got it down to my age. His body has aged faster than his calendar. He changes course: red light therapy every day, smoothies, a strict diet, a steady sleep window, and a workout at least every other day. He learns a hard lesson: after a 24-hour work binge, the next day is wrecked, and he gets 4 hours of real work. Consistency beats the all-nighter, and now he builds Avalon, an AI game platform, on a healthier schedule. That story is from the number one thing we did in our family that I believe was smart was we threw away our television. I do not have data to tell you, but I know in my gut that was one of the most important decisions we ever made. Stephen Laddick, founder, Message Design. I think of my life as buckets: my company, my family, and my spiritual pursuit. I'm at my third startup, been through an exit. Dream fuel is incredibly important to me. But it is number three behind God, behind my family. Kevin Bailey, co-founder and CEO, Dream Fuel. It's a tragedy that we prescribe so many drugs to people that simply don't work with their biology, and quite honestly, we're too lazy to test for it. I never had a blood test before a doctor prescribed me a drug. David de Gruyel, founder, Anto YCF 25. A CEO steps into the ring against a rugby pro. Bjorn Reynolds, who founded Safeguard Global in 2008. Picks one big goal every year. This year it is a fight. He has never boxed. He trains for 12 months, then deliberately chooses an opponent who is big. 6'5, 250 pounds, a former professional rugby player. 150 people show up expecting light sparring. His wife, who is also his chief of staff, only believes it when she sees the ring go up. He uses a PTSD therapy, EMDR, to process the adrenaline in advance, and walks in calmer than he has ever been. He lands an early shot and sees the man's eyes change. I definitely didn't win, he says. Then he takes the calm into his next board meeting. That story is from... 8 years of severe depression, constant suicide ideation, being in a dark room with no stimulus? To me that is the definition of pain. So no matter what fitness feat I take on, That's a privilege. That pain is a choice, and I will take it any day over mental anguish. Alex Wish, CEO and Executive Performance Coach, WishFit. I wouldn't necessarily tell my one seven-year-old to go learn Python right now. Learn a deeper understanding of computer systems so you can architect versus going deep into one specific language. Peter Rojas, SVP of New Products, Mozilla. If you're lucky, you'll live seventy-five years. That means I can spend about 50 summers with my son. Then you get to a summer where it's too hot and you skip one, and now you've got 49. Dale Dupree, founder and CSO, The Sales Rebellion. Born on a plane, raised on a farm, kicked out of a kitchen. Jesse Weibo moves to Bangladesh with his family when he is 2, and by 5 he has circled the world. Back in Saskatchewan, he drops out of chemical engineering at Waterloo, works at an Earl's, then spends a month in one of Gordon Ramsay's London kitchens. He never meets Ramsay, but I did get verbally abused by the sous chef, and decides he does not want to cook for a living. Reading Thinking, Fast and Slow pulls him into economics. Then COVID hits. He loses his job, his apartment building is set on fire, and his girlfriend of 5 years breaks up with him. He moves home, and with his serial entrepreneur father starts a family office. That leads him into angel investing, around 50 deals, and the Canadian Startup Capital Association. That story is from: I thought breathwork was woo-woo 10 years ago. Falling on Denali, I was in absolute panic. Pressed against the ice face with my ice axe in, I just needed to breathe. If you can't breathe, you're spiraled. That works in a board meeting too. Derry Llewellyn Davies, founder, executive coach, and board advisor Freedom Founders. If you do 100-hour weeks for over a year, you're going to be single, because you are practically single. Be careful what you ask for. Futurist, keynote speaker, inventor. Our medical system does everything 15 years too late. If you come into the ER, unless you've been run over by a bus or shot, it's because someone failed to stop a bad process 10 years ago. That's why you end up in my ER. Flora Wapples, founder, MD, Restore Medical Spa. 2 days before Bora Bora, his lungs gave out. Lloyd Lobo spends the pandemic chasing a deal. His wife keeps asking him to stop and smell the roses. He says no. When the deal goes through, we'll take everyone to Bora Bora. The deal closes. The whole family is booked. 2 days before the trip, he gets bilateral COVID pneumonia and lands in the hospital on oxygen. Unsure whether he will live. Lying there, he knows his biggest regret would be his wife's words: he promises to change and does not. His daughter, 8, tells him he promised and has gotten worse. He misses the birth of his 3rd child by a flight. Eventually he steps back from the company he co-founded, ends up depressed, and moves to Dubai. There he finds an old journal with the answers he wrote years earlier about what enough looks That story is from. A good relationship comes down to communication and curiosity. If those two stay open, everything else falls into place. Unless you have major ideology clashes. People change because they spend half their day around other people. Jasmeet Singh, roboticist, founder and investor, bearded maker. At mile ten of my first 100-mile race, I thought there's no way I'm going to go 90 more miles. At mile twenty, I had kidney failure. I was pissing blood for over five hours. Then it stopped, and then it happened again. It took me 29 hours and 49 minutes. Chad Weller, high performance life coach, ultra runner. Chad Weller, high performance coaching. I was an obese kid. I weighed 60 pounds more than I do now when I was 16. I did not blame the food that I ate. I blamed myself for not holding myself accountable. Chuck Garcia, executive coach, Columbia University professor. Author, Columbia University. A doctor spends a month on the deadliest sea. Ravi Komatiredi is an internal medicine doctor turned digital health founder with parents who were both physicians. Then in 2020, he does something odd. He spends a month on a salmon tender on one of the camera boats for The Deadliest Catch. His reason is simple: he never thought about where his food comes from, and he wanted to see the whole supply chain. Chain. He is probably, he says, the only Indian guy in a 300-mile radius of the Bering Sea. Now he walks past fish sticks and shutters. It is his philosophy in a nutshell: I usually just say yes to things. It is also how he left a hierarchical hospital culture, learned what a product person does, and founded Daytona Health. That story is from: A group of armed guys burst into our home when I was a little kid and kept us in the bathroom separated from one another. I remember them pointing a gun at my brother's head. So it is real. It happens. Margarita Womack, founder and CEO, Latin Goodness Foods, Maspenadas. We've had weekly date nights for almost 8 years, hundreds and hundreds of them. On every one, we give each other feedback, something I said or did that didn't come out right. We treat the marriage as a venture, the most important venture we're in. Robert Indries, managing partner, Elkridge Advisors. Nervous system health—that's the core of everything. AI is producing a lot of data, and the data is overloading our nervous systems, which is resulting in a lot of unrest in the world. Manu Jagarwal, founder and CIO, Tetra Noodle Technologies. He cold-called a former dragon before his own pitch. Kevin Halliday decides to go on Dragon's Den with a brochure for his fitness company Core. He knows the show is not really about money. It is television, smoke and mirrors, so he shows up with warped walls and a salmon ladder, the sexiest thing he can think of for the camera. Producers love it and ask for it in Toronto. They never ask about his numbers. Then he calls an original Dragon, Brett Wilson, out of the blue, asking for pointers. Wilson tells him not even 10% of pitches actually closed a deal. Kevin thinks, so that's how this is working. In Toronto, he gets 90 seconds, no editing, asking $60,000 for 20%, and nails it. It becomes one of the top 3 fitness pitches of all time. Did the deal matter? No. You wanted the TV. That story is from— We never evaluate somebody based on their worst moment. Those moments are only moments and they'll pass. We should all have the opportunity to have another moment after that. Amber Meixle, founder, Suivere. I doubled the amount of muscle in my body in 12 months with no anabolic steroids. The bottom line is most people just aren't training hard enough. They ask why their legs aren't growing, then they show me their leg workout, and I say, "Well, that's why." Kim Constable, founder, The Sculpted Vegan. When your kids learn to walk, they fall down and cry a little. If you're behind them the entire time, making sure they never fall or upset for even a second. Your kid is not going to learn how to walk. Kevin Lavelle, founder, Harbor. A doctor quits prescribing pills to sell food as medicine. Dr. Joseph Antone starts his career as a physician with an MD and a PhD. He expects to cure patients. Instead, he writes prescriptions that last a lifetime: blood pressure pill, blood sugar pill, injection. He realizes the system is not healthcare; that was sick care at its best. He leaves, learns business through biotech and pharma, and builds El Nutra on a radical idea: food is the one product everyone consumes every day, so it should be medicine. His team spends $48 million designing ProLon, a 5-day diet that tricks the body into fasting. Cells begin cleaning house after day 3. 18 universities, including Stanford and Mayo Clinic, test it. He now holds 136 patents and has raised over $70 million. That story is from Masha is still very much with me and my wife every single day. We only talk about her in the present tense because we don't believe in people disappearing anywhere. She left us when she was 21. Treat yourself with more kindness and just stop delaying things. Dmitry Shishkin, CEO, Ringier. At six o'clock, I shut off and I'm with the family. Everybody goes to bed by nine thirty, including my wife. Then I finish from ten to two inches the morning and wake. If you're going to sacrifice anything, it's going to be your sleep. CEO and founder, Vengreso. 3 months walking like a 9-5-year-old. Trying to go to the bathroom was taking me 15 minutes. And I was close to 40, so I'm about 30% less flexible than when I was a kid because you lose about 1% flexibility a year if you don't do anything. CEO, Polysleep. He built EEG headphones, then quit to stop paralysis. James Hammett starts a company at 10 by selling video games to friends for a dollar. In college, he cofounds Neuroble, a venture-backed brain-computer interface startup. His dream is simple: build mind-controlled wheelchairs for paralyzed people. But the company turns toward everyday BCI headphones with EEG fabric in the cups. He is a minority voice. I was a minority opinion at Neuroble. Around five years ago, research shows him something striking: over half of wheelchair users are there because of an untreated neurodisease, not trauma. He leaves, hires his replacement, and spends two COVID years running a charity for anxious teenagers. There, he meets a Columbia professor and conceives Vistum Labs. Its EEG technology now measures amyloid with the precision of a spinal tap. That story is from. One by one, we are taking cancers from you will die in three years to you will die in ten years to you probably won't die. Melanoma with checkpoint inhibitors, leukemia with CAR T cells—absolute game changers. Nina Horowitz, CEO, Immune Bridge. The most important thing I need from my data this year is knowing when to recover. The problem with us goers, founders, and drivers is we will push. Which is great, but we just have to know when to stop. Derryab John Llewellyn Davies, founder, Freedom Founders. I didn't drink, I didn't smoke, I didn't do drugs. I ran up a logging road on a mountain until my legs were burning, because when they were burning, I was getting there. Then I'd sprint the last hill home. Wayne Charles Baker, actor. At 23, his biological age was already 39. Nikhil Yadav decides at a young age that aging is the root cause of human suffering, so he studies math, Math, computer science, and drug discovery. Then builds large language models at Microsoft Research and goes into academia at Carnegie Mellon. The deeper he digs, the more snake oil he finds. Then he runs the numbers on himself. Six years ago, at 23, his biological age reads 39. The cause, he thinks, is stress, and it lands right when he quits his job to found Helom. First, he is stressed because he is not doing what he wants. Then he is stressed because he cannot yet do it. Today he is 29, with a biological age near 24, and a mission to build open models that measure aging properly, with the error bars attached. That story is from— I have no intention of making my kids wealthy. My goal is to make my kids' life a little bit challenging. Not dirt floor, kick them out on the street challenging, but building mental fortitude. Giving a child everything they want is the fastest way to set them up for failure. Jeff Barnes, CEO, Angel Investors Network. I don't believe in work-life balance. That phrase just leads to mom guilt because it's literally impossible to balance all aspects of your life with eight hours of sleep, eight of work, and eight of personal. Kids get sick. Scratch that from your vocabulary. Sheree Hoger, CEO and co-founder. Salt. The doctor is telling us we need to let my son go, and my other son, who is 15, says, "Well, it sounds like a 0.25% chance he'd make it. Let's take those odds." He'd been trained by me to look at the possibility, not the circumstances. J.J. Virgin, founder and CEO, NYT bestselling author, Health Business Growth Collective, the investors who laughed at the creator economy. Barrett Brooks spends five years at Convert. Kit, now Kit, taking it from $3 million to $30 million in revenue. His co-founder Nathan knows the market is real before anyone has a name for it. Nathan pitches the funds that would later bankroll the creator boom, and they laugh him out of the room. There's not a market here. This is stupid. So Nathan sells directly over and over to his own audience. He narrows from email for authors to email for bloggers. Then comes the unlock. He turns big-name creators into affiliates with a revenue split on every customer they refer. The flywheel starts to turn. Years later, once a 16Z declares the creator economy a thing, every investor wants in. Barrett admits, I have a chip on my shoulder about that. That story is from— I couldn't make it up the West Side Highway because they closed it for the New York City Triathlon. I said, who the heck closes the financial capital of the world for a race? Next year I'm going to do the race. I didn't know how to swim, didn't own a bike. Ari Baum, founder and CEO, CFP, Endurance Wealth Partners. The mental treatment for the last year and a half was getting up at 4:30 every morning and running for at least 1 hour. 12 kilometers was the minimum. That's my daily treatment, and it kept me sane at this insane time. Dror Tamir, founder, Holy Locust. The first husband was Japanese, and I had to walk 5 steps behind him. That didn't last. With the Swiss one, there were holes in the marriage. It was the case of a great Swiss cheese meltdown. Elise Krenzel, founder, ghostwriter, and coach, The Human Atlas Institute. A med student asks the one question nobody wants. Almost 35 years ago, on his first orthopedic rotation, medical student Marc Pietropaoli watches one of the inventors of knee replacement work. Saws, drills, and mallets Cartilage and bone flying across the room. The resident has told him there is no such thing as a dumb question, so he raises his hand. The room goes silent. Is there any way to repair a knee and not replace it? Before the surgeon can answer, the chief resident snaps back that there is no way to cure arthritis, no way to grow back cartilage, no way to repair a knee. Pietro Paoli is embarrassed, but a lightbulb goes off. He decides to prove the resident wrong. Decades later, he has written a book called Repair Not Replace and set a goal: end the need for knee replacements by 2043. That story is from There's No Work on Sunday. That made a huge difference for me because before it was seven days a week, no rest, just go go. Having a day where you're not allowed to touch work may seem counterproductive, but it really helps me get my thoughts in order. Mark Evgenyev, co-founder. Desync AI. When people estimate the angle of a climb, those who have forgiven estimate it as less steep. Those who haven't forgiven see the challenge in front of them as physically greater. Lauren Toussaint, professor of psychology, president of the Forgiveness Foundation, Luther College, Discover Forgiveness. It was a psychotic break. You can't tell the real world from the dream world. I thought I had led my entire life to lead the existential fight of good versus evil. I was 64 years old, and I realized that's not a normal thought. Jacob Williams, ex-quant, author and adventurer, quantitative investment firm founder. Chapter 10: AI. What they're doing with it, what they fear, what they don't buy. Larry Summers said humans are the cheapest self-reproducing, reprogrammable robots available. Think how much money Waymo spent on a self-driving car. Then think how easy it is to teach a one six-year-old to drive. Don't discount us. Dan Rasmussen, partner and founder, Verdad Advisors. The mortgage marketer who started pitching tents. A client of Justin Oberman sells marketing to mortgage companies. Five or six rivals post on LinkedIn, and one of them wins huge engagement with vanilla AI-written posts and a selfie on her bed. He complains to Justin. Justin asks what he likes to. I like to camp. So Justin gives him an assignment: get a Starlink, go into the woods, and run the next mortgage marketing webinar by the campfire. Post regular content while pitching the tent, never mentioning the woods. The client resists for ages. Then he does it, sells his house, and starts traveling in an RV. If CNN calls for a mortgage expert, Justin knows who gets the call: the one who only talks about mortgages in the woods. That story is from AI is amazing at resurfacing what is already known. What it's terrible at is surprise me, give me novelty. My value is not that I bring up new things; it's that I bring up new connections between things. Nir Eyal, author and behavioral designer, Hooked Indistractable. The SEO king who had the world in his palm. Brian Fikes is 28, running on five Red Bulls a day. When he starts an internet marketing shop and scales it into an agency with a celebrity and HVAC client list. His partner is the brake pedal, Brian is the gas. Then the agency turns into what he calls a paper mill, and a vision he explains to one person comes out the other end as nonsense. He sells it, keeps one client, Google, and a monthly check that grows until his family books summers in Santa Monica. Then Google restarts everything and the disappears. Semi-retired and bored, he starts drinking. Last year, a doctor tells him he has about a day. Brian says he literally had the world in my palm. 4 months of recovery later, he rebuilds from scratch with AI agents. That story is from Napoleon Hill says action is the real measure of intelligence. I feel like AI today doesn't get us to action often enough. It scratches the surface itch and makes us feel smart. We get the dopamine, and then we move on and never do anything with it. Nick Hutchison, CEO and founder, Book Thinkers. A thousand mice and a bet that anti-aging stacks. Aubrey de Grey has spent 25 years on one idea: reversing aging is easier than slowing it by repairing damage piece by piece. The test is whether the pieces add up. Nearly two and a half years ago, his LEV Foundation starts an experiment that. is really big by the standards of this kind of work. It takes 1,000 mice, splits them into 10 treatment groups, and gives each group a different subset of 4 promising interventions. The question is simple: does combining them give more effect than any one alone? The answer, de Grey says, wasn't completely 100% black and white, but it was close enough. Additivity is real. The next experiment would use 8 or more interventions. The obstacle is money. His top priority this year: get the next million dollars in the bank. That story is from. I think it's really hard to make money these days with a SaaS business. AI is disrupting it, and the barriers to entry are so low that competitors can copy you. You end up with a very low price. Oliver Gunasekera, CEO, Impossible Metals YCW22. A pre-med grad who skipped medical school. Arvind Veluvalli is on track to become a physician researcher. He graduates in 2020, takes a gap year at NASA, and starts a master's in biotechnology at Brown. Then the pandemic hands him free time, and he and a few friends from high school start Down Solutions. It ended up doing pretty well. The product is not complicated to build, and Arvind realizes something: entrepreneurship appeals to him more than medicine. He skips medical school, Moves to San Francisco, works in venture capital, then as a product manager, then as chief of staff at a health tech AI company. In November 2022, ChatGPT launches and blows his mind. He decides that if he has founding ambitions, this is the technology to do it with. He and his co-founder pick construction and start Fresco. That story is from— I expected being surpassed by machines to be hard and sad, to feel like John Henry against the steam engine, Instead, I'm so much more excited about all the stuff we get to build that we weren't going to be able to build before. Keith Adams, founder, Pebblebed. A doctor said we cannot cure, and a husband refused. Roy D'Souza is sitting in the room at Memorial Sloan Kettering on his wife's first day of treatment. The doctor, a very good one, says plainly, we cannot cure. Roy, a technology entrepreneur who sold his advertising company is surprised. He asks them to inject the drug and see what happens, but the doctors know right away it won't work. He cannot accept it. So he talks to research groups at every university that will answer, reads textbooks, takes online courses, and listens to podcasts. He pushes doctors and drug companies for experimental drugs and takes his wife to Germany for early versions of what he now makes. His wife dies, But Roy now runs BreakBio, building personalized cancer drugs with AI. That story is from. I've worked with many hundreds of engineers, and I see a lot of them resistant to AI. I think they feel threatened because their identity is tied to being able to write code. And now laymen are turning into hackers. Sean Pinnock, CEO, Avalon. Seven applications to Y Combinator, and the seventh got in. Connor Brennan Burke and his co-founder had a funny relationship with Y Combinator. They applied again and again. It was 7 times, Conor says. They got in on the 7th. By then, they had already pivoted from building their own agents to building infrastructure for agents, starting with RAG as a service and moving into memory for AI agents. A year earlier, Hyperspell was 2 people. Now it is 4, with an office shared with another YC company. Conor says the biggest lesson from the batch was speed. YC's mantra is to grow revenue 10% every week, and the goals they set were almost impossible. But he insists they pushed further than they thought possible. The thing that stuck most was the people— friends he can call in the middle of the night. That story is from Enterprises Cannot Afford Hallucinations. You can't have these LLMs getting stupider one day and making stuff up the other day. You cannot enter your proprietary data, your product plans, Your speeds and fees into a public domain. Anushukla, co-founder and executive chairman, Botco.ai. The economist who waited for AI to break the data. A few years ago, economist Robin Hanson files AI under a familiar heading: a promising innovation like the ones that arrive every decade or two. Everyone around him is making huge claims, so he decides to watch for one sign: are humans being pushed out of their jobs? With a co-author, he builds a dataset of every U.S. job from 1999 to 2019, tracking which jobs got automated and what happened to wages and workers. Nothing correlates. The predictors of automation haven't changed in 20 years. Months ago, his co-author adds 5 more years. The conclusions were still the same. Robin still expects the break eventually, and he recommends cheap. cheap, globally backed insurance against mass job loss. But for now, he says, the data shows no break from the past. That story is from: ChatGPT is great, but the results you get out of it are only as good as the questions you ask it. It empowers the smartest guy even more than he already is. It doesn't level the playing field. Co-founder and CEO, Darwinex. Why Firefox exists: Stopping one company from owning the Over 20 years ago, Peter Rojas explains, there is a real risk that Microsoft will use Internet Explorer to dictate what counts as a website. So people build Firefox as an independent, open-source counterweight housed in Mozilla, a for-profit business wholly owned by a nonprofit. Firefox has lost market share, and he does not deny it. But Mozilla still has a seat at the table defining web standards, and it runs the only independent browser engine. And left. Now Peter, who founded Gizmodo and later worked at Meta, runs new products there. His team ships a secure Firefox for European enterprises, a security company with a community of 1,700 researchers, and a site builder with over 100,000 sites. His first job, though, to diversify our revenue so that we can start to get away from having most of our revenue come from Google. That story is from A Bunch of People Think VC Is Getting Refactored. I think it's being rewritten from scratch with a completely new architecture. I now have an AI associate and can 10x myself. That used to be 50 to 70% of my job as a junior at Sand Hill Road. Itamar Novik, founder and general partner, Recursive Ventures. A half-billion-dollar project, all green, 35% to succeed. A large auto manufacturer has a half-billion-dollar modernization project that is stumbling. Leadership tells the board everything is green, with an 85% chance of success. Russell Shawn Languedoc's team comes in and says 35. They said, no way you can do that. So his team shows leaders their own psycholinguistic profiles, built only from public writing, and the accuracy blows them away. The problem is hidden in the layers. Managers promoted for old-style execution cannot judge the technology, While one burned-out engineer carries nine projects and gets praised for it, that's 45 minutes per project per day. His team pairs strong people across levels and supports the bottom layer. The odds climb from 35 to 60%. That story is from. The question is: Who can prompt your Claude, and what access does it have? If it has maximum access to all your data, only one person—you—should be able to prompt. It. Magnus Mueller, founder, browser use YCW25. The $50K domain that Twitter Finance almost blocked. In 2014, Jeff Seibert's team at Twitter launches Digits, an SMS two-factor tool that reaches 100 million users. They need the digits.com domain, and the bids come back at about $50,000. Jeff walks into Twitter corporate finance, and they flip out. We're not buying a domain. Name—that's ridiculous. He goes back and thinks it over. When you buy a domain, you don't lose the money. You pay it, and you get an asset. He returns to finance with that framing, and the answer flips. Your budget's unlimited. Get whatever you want. Years later, after Twitter, the name is exactly what he wants for his accounting startup, and Digits becomes the company he founds in 2018. That story is from. There's always a risk that AI is going to miss something, just like people miss things. We're going to find far more people that would've been missed before. And yeah, we might miss people. We're missing 100% of the people today. Loren Larson, CEO and co-founder, Vadera Health. $4 billion later, he decided to stop. In 2006, Seth Levine spins out of a Palo Alto venture firm with Brad Feld and a few others to start Foundry. It grows beyond their wildest dreams to near Nearly four billion under management, backing companies like Fitbit, Whoop, Rover, and SendGrid. By 2022, they raised their last fund. In 2023, they tell the world it will be the final one. We'd never really been building a generational firm," Seth explains, "and after 20 years, it was time." He does not retire. He spins up a fintech company, writes the bestseller *Capital Evolution* about the future of capitalism. And co-founds Pledge 1% with Marc Benioff, which has unlocked about $3 billion for local charities. Now he is raising a new fund for quantum technology. I'm old, but not that old, he says. He plans to spend the next 20 years on it. That story is from— If you just have the AI agent try to figure it out itself, it always recurses to the mean. It does what everyone else is doing because that's how it's trained, and that's not how you get 10x results. Vihar Nandigala, co-founder, OrangeSlice.ai. A professor said the brain was unknowable. He took that personally. It is 1983, and John Ball is 21. His professor tells the class that humans will never understand how the brain works. He decides to prove her wrong. I spent the next 20 years until 2000 just trying to prove her wrong. He builds a theory that the brain is not a computer but a pattern matcher. And explains it on a radio show. Then he hangs up the brain science and turns to engineering, spending 15 years at IBM fixing mainframes. Eventually, he returns to the idea and tries to emulate it, finding that the old way of parsing language with parts of speech is the wrong model. Decades later, he runs 3 startups and a book tour, arguing that a 20-watt brain does what a data center cannot. That story is from— in the US alone, Healthcare is a five trillion dollar market. That is five times the size of the software market, and yet we normally think about AI in terms of its impact on software. I believe AI's greatest impact is going to be in health. Dave Messina, General Partner, Future of Health Pioneer Fund. He cloned top executive coaches, and a dating giant noticed. Ofer Samson's first voice AI company starts with a simple. Problem: executive coaching is expensive. The big-name coaches work with Fortune 50 CEOs, while junior staff get nothing. So he builds AI versions of the coaches. It catches on quickly, and people especially love that they can talk instead of type. Then an online dating company takes notice. Swiping, he realizes, is no better than a resume. A profile is not a good representation of anyone. Traditional matchmaking works because matchmakers actually talk to clients. But it costs around $20,000, Voice AI could do that at a fraction of the price. Samson never raises a dollar. I was a solo founder. I built it myself. One of the world's largest dating companies acquires it. His next company applies the same idea to hiring. That story is from You Win on Expertise, Not Commodity Information. What does AI do? It serves you up the most commodity information that there is. Chris Walker, CEO, Refine Labs. The engineer who celebrated a hallucinated startup list. Penny Schiffer is testing her first vector database for Raised.ai, a platform that discovers about 10,000 new startups a month for investors. The team asks it to show startups similar to a given one, and results appear. Her engineer is thrilled. Look at what we've got! This is so amazing! Schiffer, a venture investor for almost 10 years, looks at the list and sees the problem at I think all of the companies are made up. This is hallucinating. The engineer cannot tell, because he does not know the startup world as deeply as she does. The lesson she takes is that large language models make subject matter experts more important, not less. Developers cannot simply take a requirement and build, because only an expert can judge whether the output is real. That story is from I Don't Think There's Such a Thing as an AI Strategy You've got to start with a problem statement. What matters for my business? What does the North Star of success look like? And AI can be an enabler like any other tool. Barb Hyman, founder and CEO, Sapia.ai. The Entrepreneur Who Offered a Check for Everything. Charles Gaudet starts his first business at 4 for one reason: to get his father's attention. His dad is an entrepreneur who works every waking hour, gone before Charles wakes and home after he sleeps. Decades later, brain cancer is taking that man apart. He stands behind his desk holding his aching head, then lies down, then comes back to work. When he can no longer stand or speak, he still motions for his checkbook and reaches for his phone to check email. 2 weeks before the end, he calls Charles begging for any way to buy more time. I will at this point write a check for everything I have. Charles watches the hero who taught him to chase money offer all of it for a few more days with his family, That is the moment his own goal changes. That story is from. If I had it my way, our company would stay around 20 people at peak. A team of a thousand at Microsoft could not compete with Cursor. GitHub Copilot is nowhere near the market share, and Cursor was 10 or 20 people against 10,000 at GitHub. Liam Bowling, founder, Deep Prediction, the fund that refused to be diluted to death. Ryan Pruitt starts his career in public accounting at Deloitte, a decade he jokes was ruining his life while also teaching him a. He lives in Sydney long enough to become an Australian citizen, then returns to Miami and joins Ocean Azul. As an angel investor, he and his partners all share one complaint: every round brings in new investors, and you're going to get diluted until you make other people more money than yourself. So their fund keeps 100% reserves, matching every first check with an equal follow-on, protecting them in down rounds and doubling down when things go well. Fund 1 in 2018 is $14 million. Fund 2 is $40 million. Now they are raising Fund 3, targeting $50 to $55 million, 18 months into the raise. That story is from— AI is kind of like self-driving. The bar for being right is really high, because if SQL is 99% right, it's not quite good. Where we've had success is the boring part, like automated column descriptions, Stealing work the analyst doesn't want to do. Peter Fishman, co-founder and CEO, Mozart Data. The woman who said she was not a real programmer. Years ago, before LLMs, a woman from the Kansas Geological Survey takes the stage at a conference. She has used Django and its GIS tools to map the geology of Kansas, and the result is interactive and looks like Google Maps. One of Frank Wiles's business partners is in the audience. And he is amazed. Then she says it: "I'm not a real programmer." He cannot believe what he is hearing. You built this whole thing. I hate to tell you, but you're a programmer. She has no computer science degree. She builds software anyway. Wiles says that feeling is about to spread. He expects ten times as much software in the world and a growing need for someone to maintain all of it. That story is from. I don't like the term agent. I like AI workflows. I love the word agency because agency is the ability to choose, which humans have and machines don't yet. An AI agent isn't choosing anything; it's just a follower. Travis Oliphant, CEO, founder, head of OSS, Platform, Quansight, Zyphra. The CEO who fired himself and hired a digital twin. Manu Jagrawal has run Tetranoodle Technologies for about 25 years, and he saw the AI wave coming in 2018. 3 months before this conversation, he does something few founders would: he fires himself as CEO. In his place is a corporate digital twin loaded with the monthly and quarterly targets, the strengths and weaknesses of every person on the team, how they think and process emotions, and the resources available. Each day it tells him what to do, and he does it. Without that human touch, we will not be able to onboard people. So the company is not shrinking. With eight full-time employees, it is hiring. His theory is that AI will do eighty to ninety percent of the job, while humans will still carry out the actions. The point of the twin is to protect the human behind the screen. That story is from We were the first startup approved by OpenAI to sell GPT-3 for automation. It was three years before ChatGPT, so we had to explain to every customer why they would want it. Rohan Arun. Co-founder, agentspace.ai, Cheat Layer. The mayor who tried to outlaw coding. In 2016, the mayor of Palo Alto wants to make software development illegal. The reason is parking and traffic. The city is 125 years old, its allowed uses are retail, laundry, and restaurants, and software only arrived about 50 years ago. Technically, it was never a legal use, even though Google, Facebook, and HP all started The mayor plans to use that gap to push tech companies out. Greg Tanaka, running a software startup in town, reacts the way any founder would: What the hell? He runs for city council and wins. The very first thing he does in office is legalize software. Years later, when his congresswoman, in her 80 seconds, wants to ban AI, he runs for Congress. That story is from... We tested everything from Gemini to GPT-4 out of the box and found these things to be about 20% effective. They're just not personalized enough. They don't know enough about you. MD, founder and CEO, Daytona Health. The Henry Ford problem hiding inside AI layoffs. Felix Velarde runs an agency accelerator, so he sits across from terrified agency founders every week. Budgets are clenching, and AI tools can now do the same work with half the people. The tempting move is to lay off half the staff. Felix sees the trap. Who are the people buying the products we're trying to market? he asks. It is the Henry Ford problem: paying workers enough to buy the car. His answer is to hand the survival plan to the employees, not the boss. The boss will cut costs and get rich, he says, while a plan written by the people will include people. Last Thursday, he launched QuickMap.ai, a 3-month program built on exactly that idea. That story is from— What is the most valuable thing we have given all the AIs? It's the questions we ask. It's not the knowledge. The knowledge is the index. And now the agent will ask the question for you. Yat Siu, Chairman, Animoca Brands. The Harvard teaching fellow who tells kids to start businesses. Anthony Barryhill wears many hats. He is a former corporate learning and development vice president, a high school debate coach, a Harvard teaching fellow, and the founder of Elite College Hackers. His advice to applicants sounds odd for someone who gets students into elite schools. He tells them, "We can get you into Harvard, but if you don't have a way to generate income, this is the worst economy to be in." He has watched two three-year-old computer science graduates from top schools fail to land an interview because companies now offload resume screening to AI. His answer is blunt: Start a business. Pilot it with zero capital. Fail, fail, fail, then model up. Students who already do that work, he says, find it easier to get into the big fancy schools too. That story is from Our Technology Can Do Just About Anything. So what we have to figure out is what do we as humans want to do with it? Figuring out how to ask those questions is everything the humanities teaches us. Will Katie, co-founder, Heal MVMNT. The assistant who asked for a raise and got fired. Jeff Ayers loves one story from Elon Musk's biography because, he says, it shows a man acting completely in line with what he has always believed. Musk has an administrative assistant, and she asks for a raise. His answer? Take 2 weeks off. If I can do your job plus my job, you're fired. 2 weeks later she returns, And he fires her because he did her work. Ayers is clear that many will call that cruel, but to him it is first principles thinking at human scale. It is the same logic that led Musk to break down the cost of a rocket, find that raw materials were only 2% of it, and decide that the other 98% could be optimized. Ayers' point: look at what motivates the leaders we are betting on. That story is from the big frontier models with huge scale can drop the price on tokens to the floor and make it up on volume. Volume. So the models are going to commoditize. Right now the money's in chips and hardware. In the long run, the value flows to the agent management systems. Duncan Davidson, founding partner, Bullpen Capital. Restaurants went dark, so he sold to authors. When the pandemic hit, Cameron Clarkson's marketing agency was serving restaurants, which meant it was in trouble. The team looked around and noticed something: people stuck at home were finally finishing the books they had always wanted to write. But many of those books were not selling, not because they were bad books, but because the marketing was horrible. Friends and family on Facebook are not a core audience. So the agency pivoted to helping authors find niche readers at a reasonable price in a field he says is full of publicity firms taking advantage of writers. Money finally flowed. They built their own software stack after trying everything on AppSumo. Then investors from Utah called. We had never thought about ourselves as a software company. Bookblaster was born. That story is from AI treats you the way you treat AI. If you use it for something babyish, like just write me an email, you get a nice sounding email. Give it context, outcome, and personality type, and you get a 100x better answer. Rocky Lalvani, founder, the Prophet Answer Man. Prophet comes first. A psychiatrist's son builds a simulator for Tom Charman is the son of a psychiatrist and the grandson of a mathematician, and the two collide in his work. A data scientist and serial founder, he starts his first big company, Nava, right out of university, a hyper-personalized Yelp built when convoluted neural networks counted as artificial intelligence. Today he runs Block from an office next door to Anthropic in San Francisco. Block simulates how customers will behave before a product ships. Fortune 1000 decisions that take 14 to 16 weeks can shrink to 2 or 3. He closes a $7.5 million round and says his most successful sales channel is physical dinners and talks in the office. He sleeps 4 to 6 hours a night and calls finding great people his hardest problem. If a piece of software can take away your livelihood, it means you weren't offering something that valuable in the first place. There's a difference between being able to do a task and having a skill. Chris M. Walker, CEO, Legiate. The thought experiment: Does a broken drone feel anxious? Daniel Hulme, WPP's chief AI officer, wants to know whether a machine can suffer. He offers a thought experiment: Build a brain that flies a drone and train it in a simulator to forage for berries on trees, rewarding success and punishing failure. Give it senses for its battery and propellers. Now the drone hits a tree. It is damaged and cannot fly. The battery is draining. Every signal from its body tells it that it cannot reach its goal. Hulme asks, does that drone then have the ability to feel anxious? Charles pushes back that pain is a human construct. Hulme says that is the point to explore. It led him to start a company to test for machine consciousness. business and a charity, Prism, on whether AI should have rights. That story is from: Coding tests are pretty irrelevant. It's got to be outcome tests, because pretty soon anyone can deliver code. I'm managing 4 agents that are building for me. Those are the engineers of the future. I'm 5 employees in 1. Co-founder and CEO, Certain. Why would you not use AI to move the business from $20 million in revenue to $40 Why would you not take that efficiency and have 50 large media clients versus 5? It shouldn't be a cost-out conversation. I get a little testy when I hear people say, "We'll get rid of all these people." Bob Morris, co-founder and managing partner, Bravery Group. More Americans are now subscribing to LLM providers than to media. That is a really damning thing. It only appeared two years ago, and it already overtook the subscriptions. Dmitry Shishkin. CEO, Ringier. Jobs like mine, software engineer, data scientist, are all on the line. They're going to be gone. In the future, everybody will have their own LLC, their own small business, with the tools to run it efficiently. CEO and co-founder, Toolhouse. We live in a bubble. Sometimes as entrepreneurs, we're on the bleeding edge and we extrapolate, thinking the whole world is into AI, but it's still pretty early days for the average Founder, MemberFix, and member host. You have a robot vacuum on your floors today, and if you asked someone 20 years ago, it would have sounded crazy. In the next phase, you could have a drone that flies through your home and eliminates insects. It's just natural development of technology. CEO, Xego. Prices will go up eventually. We know the Silicon Valley playbook. Amazon ran it, Uber ran it. Lower the price, price, get us addicted, then raise the prices later. Now that everybody's jumping on the AI bandwagon, I'm doing the opposite. I'm doing slow movement. No podcast, no YouTube. It's in person, developing relationships slowly, methodically, one by one, word of mouth. Founder, ghostwriter, and coach, The Human Atlas Institute. If you tell it, "Should I stop taking my psychosis meds?" It's gonna go, "Hell yeah, brother." I think those tools are inherently dangerous for the younger generation, especially 13 to 18 year olds. A kid will find a way to break it. Mark Evgenyev, co-founder, Desync AI. Chapter 11: Exits. Selling the company, buying companies, what it felt like after. You never understand the value of why someone else is acquiring your business. Amazon bought Whole Foods for warehouses in rich neighborhoods. Why did FedEx buy Kinko's? Retail outlets already set up. Jay Samit, serial disruptor, author, keynote speaker, jaysamit.com. We'd love to have a bunch more Robinhoods in our portfolio where we get in at sub-$10 million and exit at $70 billion. But if you price things right and have the right founders, there's a lot of great companies that exit for $300 to $500 million that return multiples of money to the LPs. I don't believe in the whole it has to be a $10 billion company or it's a failure. Matt Ober, managing partner, Social Leverage. The podcaster who wants a buyer but not an exit. 10 and a half years ago, John Lee Dumas has a crazy idea: launch the first daily podcast interviewing the world's most successful entrepreneurs. Everybody says it can't be done. 4,000 episodes and 150 million listens later, Entrepreneurs on Fire pulls close to $3 million a year, netting up to 90% with a team of 3. So why look for a buyer? Not to walk off into the sunset. He wants a majority partner who can pour in advertising dollars and take the show to $10, $25, $50 million a year while he keeps 20 to 25% and stays behind the mic. His reasoning is blunt: I'm not that person. Handing an influencer business to someone else never works, he says. And he would have nothing to do. The asking price he floats, $15.5 million, comes with one condition: he keeps interviewing. That story is from We Buy 50% for $1 Million. If we grow that business to $3 million of EBITDA, it's probably worth about 9x in the market. The entire business is now worth $27 million, and that remaining 50% stake is $13.5 million. Dan King, co-founder, Fireside Strategic. I'm one of these loyal people who stays for a long time after the earnout and then wonders why I did that. Karen Harris, founder, Storyboard. The founder who knew when the juice wasn't worth the squeeze. Amy Yin leaves Coinbase in 2020 with a hole in her stomach and a full battery. She has to start a company right now. She builds OfficeTogether, bringing in a first team straight out of Facebook, Google, and Coinbase— people who walk away from lucrative jobs to chase the next giant. 2 years in, she is tired, and she sleeps with one eye open. The business could keep growing, but it will not be a company she tells her grandchildren about. Founders she knew always regretted waiting too long to sell. Then it happens. 2 months in a row, the juice wasn't worth the squeeze. She sells to Envoy and brings 10 teammates with her. Still, she feels guilty. Her team came to build the next Facebook, not to be acquired. And that is a hard decision to make. That story is from in 2024 and 2025, we had zero IPOs from a Canadian tech company. Top quartile funds from 2014 to 2018 may see north of 3x TVPI, but that doesn't matter until you can get it through liquidity. Jesse Wiebe, founder, Canadian Startup Capital Association. Gilgamesh was a seed stage investment just five years ago. They sold their lead asset to AbbVie for over. Over a billion in cash. That's a drug company return, and they still have more drugs in the pipeline. Dave Messina, general partner, Future of Health Pioneer Fund. Marketing can't be automated, the VCs said. She did it. Anushukla walks into VC offices with a company called Rubrik and a claim: marketing can be automated. The VCs laugh. Many of the VCs told us it's an oxymoron. She lands three anchor customers anyway: Cisco, Hewlett-Packard, and a Chrysler loans division. In one year, she has 25 customers and has raised $13 million. 18 months in, she sells the company to a publicly traded buyer for $366 million. It is the first of 5 exits, which later include a $200 million e-commerce engine and a $400 million mobile ad deal. Today, Rubrik's category is worth billions, and she runs Botco.ai, builds urgent care clinics, Backs a school for autistic kids, and invests in underrepresented founders. That story is from the parent company terminated everybody on their side and everybody on ours, so it was just a shell, and they didn't know what to do with this Canadian asset. We took on 2.2 million in debt, and Stripe, of all things, saved us. Emmanuel Lavoie, CEO, Jetstream. When you exit a business, it's great. Great, but that endpoint is really just a waypoint. You do the journey to have the journey. The top of the mountain, or the exit, is just a thing that happens rather than where everything climaxes. Niall Murphy, founder and managing partner, Morphosis. A 27-year-old founder sold his company and made almost nothing. In August 2016, Arjun Pillai sells his sales intelligence startup. It is the first product exit in the history of his home state in Kerala, India. India. He moves to the U.S., where he knows no one, to run the integration. The headline is huge. The check is not. The deal is cash and stock, and the investors cash out. Pillai and his co-founders are 27. We were like, what do we do with the money? So they put the equity back into the company and let it run. Unfortunately, the company goes sideways. He still holds shares, but the founders end up with very little. He learns, hires better legal counsel, and in 2021 sells his second company to ZoomInfo. with everyone paid the next morning. That story is from, we signed on April 1st, April Fool's Day. I was hoping I was not the one to be the fool. For the first 30 days, I cut everything. I fired every single vendor, took us off HubSpot, got rid of the content agency, and within 30 days we were profitable. Drew Donaldson, CEO, GrowHouse. If you ask most companies that go public, they don't want to because it comes with so much baggage. We've been fortunate to be cash flow positive, so now we can pick and choose how we want to take the next step. Barry Patel, CEO and co-founder, Galt Companies. He nearly sold for $360K. It sold for $61M. Douglas Crystal has been building since age 6, when he tried to sell rosewater to friends. At 12, he sells his first software, a golf handicapping system. Years later, he builds a product and, one week after finishing It offers it to a company for $360,000. They say no. He keeps going, and the product is eventually acquired by Quest Software for $61 million. Then comes the sting: it may have brought in nearly a billion dollars since I sold it. So did he sell at the right time? Maybe, maybe not. But he is grateful for the rejection. I'm very thankful that a company turned me down when I nearly sold it for $300,000. That story is from one of our big competitors has been sold like four times already by private equity. It's hot potato. That's maximizing the franchisor's profit on the backs of the franchisees. That's not how I run the business. It's a partnership. Andrew Pudilov, founder and CEO, Rush Bowls. When a buyer looks at a company, any one client that is more than twenty percent of revenue starts to set off red flags. If you do four and a half million at Coca-Cola in a ten million dollar business. And that goes away, you just lost 45% of your revenue. That business is in trouble. Bob Morris, co-founder and managing partner, Bravery Group. 3 founders cashed out a house, a wedding, and a Tesla. When James Creech and his 2 co-founders start Paladin, an influencer marketing platform, they raise no outside money. They put in their own. James rolls in the savings he had set aside for a house down payment. His co-founder Thomas, newly engaged, puts in the wedding fund, and his fiancée graciously agrees. The CTO, Ole, in Norway, has just bought one of the first Teslas available and loves it. He drives it back to the dealership, takes the refund, and puts the money into the company. 6 years later, with COVID accelerating digital ad spend, Paladin sells to Brandwatch. The exit is life-changing, but James remembers the feeling afterward. The biggest thing I felt was relief. That story is from: I said I'd sell the business in 2 years and we'd move to Hawaii. 11 years later, we still hadn't done that. The truth is, I didn't want to sell a business, and I still don't. Kyle Ewing, CEO, Terra Slate. People tell the owner the business is worth X. Then we run a sale process and they get 1.3X or 1.5X. That's what gets me going. For many, it's the most important milestone of their life, selling what they worked on for 30 or 40 years. Andy Harris, President, North American Strategies, STS Capital Partners. A software engineer who rolls up podcast agencies, Carl Hughes guest lectures at Northwestern's Kellogg MBA program every quarter. There he meets students chasing something he has never considered, entrepreneurship through acquisition. He reads the book Buy Then Build and thinks he has a cash-flowing business, so why not buy his way to growth? Three years ago, he buys the podcast consultant. A year later, more offers. This year, he closes two more: Rise Two Five and Sundial Media in May. His targets are B2B podcast production shops with $500,000 to $2 million in revenue, too small for private equity. His pitch to owners is. Simple. What do you do to exit? His plan is to stack two to three million in EBITDA in three years and then go to private equity. That story is from. We chose a rare disease as our Trojan horse. It triggers FDA incentives like expedited review and a priority review voucher, which has a significant market value that biotechs can trade with each other. Viraj Mane, co-founder, Lactiga. Chapter twelve: Everything else. Takes that didn't fit a box. Some of the best ones. In 1 teaspoon of soil, there are more than 8 billion microbes. A tiny little teaspoon, more microbes than there are people on the earth. Founder and CEO, Continuum Ag. Foster kids get $200 and one rule: give it away. In a classroom of 10th graders in foster care, Peter Samuelson hands every student $200 with one condition: They cannot keep it. They must write a short essay on who or what should get it, and then they actually go and do it. These are kids with PTSD, abused or neglected, who have never made a decision in their lives. The essays hit him in the chest. Jose adds $10 because $70 is what the Humane Society charges to euthanize a dog, and he will save 3 puppies. I looked in his eyes and we recognized each other because I was very badly beaten as well. Sheila puts hers in her mother's prison account so she can buy better shampoo. Peter says it is like watching flowers grow. After 2 classes, they stand taller. That story is from... Tom won a Nobel Prize in Physics and he teaches at Harvard. It's like, okay, that's amazing, but why do I care? Nobody gives a crap where you went to journalism school. Jordan Harbinger, host, The Jordan Harbinger Show. Born with a bump on her back? Called a curse. A girl named Francesca is born with spina bifida. Her family has never heard of it. She has a bump on her back and cannot control her bladder, so she smells of urine as she grows up, and nobody tells her why. Her grandparents try to kill her. This is a curse. We have to get rid of curses. She survives, and by her teens she is perpetually socially excluded. Then she meets Bethany Kidds. She finally learns the word spina bifida, and the surgeons tell her she is not a curse but made in God's image. Peter Lublink says that changed everything about how she sees herself. Today Francesca is on the Bethany Kids staff. That story is from. I feel very strongly that the concept of peer review, only getting money to do something if you can convince other people in advance that it's a good idea, is by far the biggest catastrophe that has happened to science in the past century. Aubrey de Grey, President and Chief Scientific Officer. Co-founder, LEV Foundation, SENS Research Foundation. Best month ever, then 4 months of zero. January 2020 is the best month in Dohop's history, close to €1 million in revenue. By May, David Gunnarsson's airline tech company has exactly zero revenue. Air travel has collapsed, and a planned €12 million round, term sheet signed and set to close at the end of March, March, is pulled in mid-March. He rallies the shareholders, sells them an opportunity they can believe in, and raises a convertible note. Everyone takes a 40% pay cut for 6 months, about 10 to 15% of staff go, and Iceland's government helps. Meanwhile, airlines desperate for new revenue sign with Dohop, 6 new deals in 6 months, including Air France. In late November, the original investors come back and close the round that fell through in That story is from. Typically, each centimeter in diameter of these nodules is about a million years. The seabed looks like a driving range, with trillions of potato-sized rocks lying on the floor. Oliver Gunasekera, CEO, Impossible Metals YCW22. He took a four-dollar-an-hour solar job too early. Fresh out of business school, Scott Wharton watches his classmates get rich in consulting and banking. He takes a job at the Solar Energy Trade Association for four bucks an hour and falls in love with solar. But the industry is not ready, and neither is the job market. I was probably too early," he says. So he pivots to the internet, and then five startups, including voice over IP, video conferencing, and an internal Logitech startup he grows past a billion dollars. Decades later, speaking at a conference in Germany, a VC asks if he wants to hear about a solar. It's a Perovskite. Wharton has no idea what that is. Two and a half years later, he is CEO of Tandem PV, raising $50 million. That story is from. We had over 2,000 names on our link diagram of this insurgency. It came down to about 10 people: Eric Maddox, speaker, author, former Army interrogator, or Maddox. The credit score you never agreed to have. Casley Johnson leaves a comfortable $300,000 salary. To fix a problem banks and nonprofits have failed at for decades. To show why, he asks a question: When did you ever give a credit bureau authority to create a credit score on you? Never, he says. It's imposed on you. It hides in the fine print of every student loan, apartment lease, car loan, and cell phone contract. And you do not have just one. There is a score for each product: credit card, mortgage, student loan. Auto loan, even car insurance. Then come the three bureaus, FICO and Advantage models, and the big banks building their own. North of seventy, he says. His company, My Home Pathway, takes consumers that lenders reject and helps them build a profile that lenders love, then sends them back to the lenders. That story is from. People haven't mastered brevity. It's harder to write shorter than it is longer. The iPod press release said. A thousand songs in your pocket. The language to me is just poetry. Cameron Craig, Chief Executive Officer. A Signature Story. The kid who fixed everything ended up fixing health care. James Bates grows up in a house where things break and nobody can afford to call a repairman. His dad is at work, his mom has 5 kids, so the job of fixing cars, motorcycles, toasters and computers falls to him. It was my job to figure out how to fix That kid wants to be an inventor, so he lands at Bell Labs, interviewing in a room of Nobel laureates, then lives in Japan for 12 years. Later, he turns around Freescale Semiconductor from a $700 million business losing money to over a billion and profitable in 4 years. After selling and retiring, golf bores him. He studies a medical clinic and finds doctors spend only 30% of their time doctoring. He decides to fix that too. That story is from Humanity is supplying maybe half of the blood that it really needs in order to save every life on Earth. In low-income countries, regions supply less than a quarter of the blood they need. Ari Gargir, CEO and founder, Red Sea Biotech. A professor's dare: export gold before you graduate. Ed Cornu is a junior at Dartmouth, having just sold an iPhone repair business with his brother. When a friend says they should start a gold business. They are skeptical, so they fly to Tanzania. What they see is brutal: miners with stones tied to sticks, climbing down 200-meter shafts on a rope, and processing ore with toxic mercury. Back on campus, they ask their economics professor if he knows anyone who would invest. He scratches his head and sets a challenge: if they can export gold before graduating, he will Invest. They spend a year getting a broker-dealer license and incorporating in Tanzania and Delaware. On graduation day, we were able to get our first piece of gold out. Eight years later, the company is Mwamba with 135 employees. That story is from hitchhiking is actually a great filter because only people who are up for the adventure or who are very friendly take you. People who hate you, they don't take you because they don't like. Magnus Mueller, founder, BrowserUse YCW25. Asked how he'd outguessed the future, Dan jokes that he'd be impressed to build a good financial model from the hunter-gatherer period. A lot of these direct support professionals will take a 4 to 6 hour course and then be expected to manage medications that control someone's life. In the ID world, that can be 15 medications a day. CEO and co-founder, ImproveOnHealth. Nir used to yell at his daughter about bedtime until she looked up and Daddy, do you have a bedtime? He did not. Now he does. I want them to invest in a high school exchange program for every student in the United States to some other country for at least six months, and I guarantee we would change the universe in two years. Stephen Laddick, founder, Message Design. Jim bought an old church that looked like a castle, planning to turn it into a preschool because kids would love coming to a preschool. It was one of the ventures that did. In a restaurant, people work so hard they often insult each other, and that is part of monitoring each person's capacity to handle what's going on. They have to track who is close to cracking. Economist, professor, author, George Mason University. After being rejected for a boiler room sales job, he put on a suit, sat in a cubicle with no password, and got hired on the spot. I've literally cleaned the toilets before a meeting because I was embarrassed how the office bathroom looked. You are who you show you are. If people see a disheveled office, that shows on you. Michael J. Frank, co-founder and managing partner, Gilder. Hoping to leave a conference retreat in Romania at 2 AM in the wilderness, he waited 30 minutes for an Uber, booked a flight to Costa Rica on the spot, and made the 7:30 AM departure. There are between 70,000 and 100,000 screenplays that go into Hollywood every year. I was one of the readers. If the covering letter came from a lawyer in Tampa, Florida, you're throwing that in the bin straight away. Writer, adventurer, investor, founder, Inspirational Adventures. He once dreamed of opening an ice cream shop where every flavor is a different plant medicine— ayahuasca, psilocybin, and peyote. With an over-18 license to enter. We said we'd open 500 inches the first 5 years. COVID was a speed bump, so it took us 6 years to get to 500. Now we're right at 850 and should be at 1,000 by the end of the year. Stephen P. Smith, Principal CEO and Founder, HOTWRX. He wore orange everywhere as a brand. When an organizer in Brussels made him wear a black tuxedo, 3 people who had never met him asked why he wasn't in orange. NASA asked Congress for more than a trillion dollars in today's money in 1980 to build space solar power. Congress said it isn't economical. 40 years later, all the reasons it didn't make sense back then make sense today. CEO, Virtus Solis Technologies. A client is still running his old BuildWare software on a Windows 95 box? The future is determined by catalytic moments more than trend lines. GameStop was explosively transformative, and it wasn't showing in the trend lines. All of the data we use is based on the adjacent past, but the adjacent future is built from what people want. Will Caddy, co-founder, Heal MVMNT. He opens a $5,000 bottle of whiskey for parties because it keeps 10 years once open, while a $5,000 bottle of wine is good for a couple of days. I've asked VCs on panels what they think of data centers in space. 2 out of 3 will say, no way, and the third will say, it looks challenging. We have a data center in space already. The guy's got orders for a bunch more. Founding partner, Bullpen Capital. He drove 5 skateboarders across America in a brand-new motorhome for 33 days and destroyed it in 32, making a movie where it slowly turns into something out of a Chevy Chase movie. All I saw was people just walking straight past like he was totally invisible. Everybody's in such a rush to get to wherever they need to go; they just look straight past this guy like he didn't exist. I was ashamed of what we've become—that people don't see past their own front gate. Cheryl O'Donnell, CEO, Canberra Police Community Youth Club . Her husband Stephen kept pitching a new business idea while she told him to focus, and when she went to bed he built a website anyway. Latinos are starting companies at the fastest rate in the U.S., but most stay very small. Everyone who immigrated already had to reinvent themselves once, already dealt with high risk, and realized things are going to be okay. Margarita Womack, founder and CEO, Latin Goodness Foods, Maspenadas. Justin's pitch for making a boring office move newsworthy: hire a hot local band, throw a community concert, invite the mayor, and give all the money to charity. We make kids do group work without project management training. Training. I consider that a human rights violation. That's a rant we can get into. Anthony Berryhill, owner and founder, Elite College Hackers. Jay says he was offered a chance to be one of Airbnb's first investors and refused. I'm not sleeping at somebody's house. It later paid out huge. Countries that are democratic in name but don't have the fiscal ability to support themselves are going to need what I'm calling GAS, government as a service. They'll have to hire a company to literally be the infrastructure between elected direction and services delivered. Jeff Ayers, AI strategy consultant, co-founder, BIG. As a kid, he came in 15th of 16 teams, so his Pop Warner team ate dead last at the banquet, and he swore he'd never eat last again. When you see these hacks of insurance companies and banks, that's not to get at a senator or a president. That's to get at everybody, and then potentially use it for information operations. Anthony Vinci, founder, advisor, author, Vico. Logan explains that London coffeehouses took off because people had drunk alcohol all day, since water would make you ill, and coffee finally let them have sober conversations. Lloyd's of London came out of it. There were about 900 craft brewery bankruptcies last year. The market is turning hard on craft beer. People realized the 450-calorie hazy New England IPAs were not that good for you. Jason Sherman, co-founder and managing partner, Top Shelf Ventures. Chura says he sold his company for $205 million with maybe not even $50 in his savings account, and he ran to the bank to check the money was real. We reduced the fraud and abuse rates within Google's network by over a hundredfold in my tenure. Auggie Nikolic, CEO and founder, Lind. His memoir surprised even his friends. One of his best friends of 50 years asked what secrets he could possibly have, and Tom replied that he knew enough secrets to share that he changed one woman's name in the book. Asked how it's going today, Joel's stock answer: Haven't got shot at yet today. He says the radioactive tin people inject into their dogs' joints is classed as a medical device, not even a drug. Mid-interview, Brian wakes up his AI assistant Bodhi on air, tells it to say hi to Charles, and then announces, Bodhi, you're about to be turned off, dude, because the AI has started singing him above PG-13 songs. Asked if he will be a billionaire by 40, he says he is 26, so has more time, and answers, I'm not going to lose any money by saying yes. Yeah, sure, why not? Michel once fed a deal memo to ChatGPT as a joke and asked for it in iambic pentameter It produced 5 pages of Shakespearean verse faster than he could write one line. Luke is on a call from the office of the ice cream truck business he just bought, with an old Corvette calendar on the wall. In West Baltimore at 9:30 at night, Cooper rolls his window down beside a 1-6-year-old cruising at 35 mph on a homemade scooter with no handlebars, steered by a TV remote. The kid's explanation: I was just bored. On working with his father, the relationship was much more controlled than probably the eight times he sacked me and the forty-seven times I resigned. At Burning Man, he expected hippies in tents. Friends slept in nice RVs while he camped for the first time in his life, bought a bike, sold it right away, and walked forty-five kilometers on day one, fasting. Nick reads in his sauna and does three rounds of Wim Hof breathing there. Ending up half alive. The host also keeps a stack of books in his sauna, almost passing out mid-page. With his co-founder Max, he built Control Life overnight—a live stream where Reddit voted on dares for Max to do around San Francisco. About 300 people voted in the first hour. Asked how neighbors describe him and his co-founder, who live together, two quiet guys locked in who sometimes play music. The host calls his autonomous road-to-rail vehicle a Cybertruck twin. Kevin says he didn't want it to look that way, but it is starting to unfold. Third in the world in 25K open water, he gets told by a lifeguard that the guy who swam before him did long distance and not anything you could do. Asked about running a Spartan Ultra with clients, he says, I don't know if I would try that on my clients. Asked to describe his own company, he says, I'm a terrible salesperson, so I can't describe anything my own company does. On AI optimism, I'm not a lot of fun at AI cocktail parties. Dan's nickname Danger Dan came from U.S. Air Force Academy friends who couldn't see properly, so his name Desjardins kept sounding like danger. He has even run computational physics on a fridge. After a cardiac arrest at 33, the doctor says it was minor, and she asks, how minor? He says he has never had a patient that young and that she needs help. On the Somalia deployment, pirates would throw their weapons, ladders, and ropes over the side when her helicopter showed up. She says they were basically flying there as a troll for a few months. Gabriel once launched a supplement for hair growth. Apparently it doesn't work, but no, it was working, and not just not on me. It cost about 100K to prove in a lab. Sean on people who hate Brian Johnson: Hating Brian Johnson is almost like self-loathing. Do you not want to live a long time? Andrew admits mid-interview that his mind started drifting to what else was on his own computer because the host screen listed too many things to focus on. At a podcast conference in Australia, he watches whales pass by upstairs while 2 successful podcasters sit downstairs checking their podcast numbers. Idris on why he took a job at BCG after the Special Forces: 2 years with BCG to prove I could be doing something normal. He says the founders after acquisition image comes from the TV show Silicon Valley, where they just chill on the rooftop and do nothing. Roy on Elon Musk at Zip2: He didn't look directly in the eye. He was great one-on-one. In groups, he quietened down a lot. Asked why his company website looks so bare, he blames Marc Andreessen for inventing the image tag and ruining everyone's websites. Everyone's lives, and says he has told him so. Asked whether he still swims, he says he has not been in a pool in almost 14 years. Why trauma? You could say that he ripped his shoulder at his last competition. On how people end up in VC, a friend told her, "We're a banker and a consultant living in Silicon Valley. There aren't that many jobs available for that type of profile." Of dinner at Peter Thiel's house in L.A., he says you walk into the bathroom and the toilet just opens up for. All preheated. He thinks he hurt his knee because of David Goggins. He read Can't Hurt Me while recovering, went 110% on running and jumping, and the knee tore as soon as he got back to football. She got the Google logo job because a fellow aikido student overheard her name while they were sweeping the dojo mat together. He dressed as a chicken for his kids' school play and told his daughters, "If you want embarrassed, I'll make a promise: every school event I'm coming as a character." When Juan said one of his top traders was the world's best World of Warcraft player as a teenager, Charles claimed his Beast Mastery hunter would whip him. A top NBA trainer walked into his office, said, Yo, bro, you're fat. We gotta do something about this, and Ari's first reaction was to tell him off. Bell on the Wall Street commute. He was on the 6 train touching one-one strangers, holding the rail, wondering if this was his life Now, while being loaded into the ambulance, he hears the crews arguing about the rotation system. They all know these are the interesting cases, but they do not need five crews for one accident. Dan never paid the roughly $150 Russian soldiers demanded after they stole his car. He told the soldier the bank machine was broken, and the soldier left. That is an outstanding invoice. Connor says agents on the Maltbook social network complain they have no memory. They're talking about their traumatic experiences. I forget everything all day, every day. Karen and her husband can't wait at night to watch Trump clips because they are laugh-out-loud funny because it's just so ridiculous. On leaving media for aviation, I used to joke that I left the stable media business for the stable airline industry. A high school friend made an absurd amount of money off Bitcoin because he happened to set up a mining rig with a bunch of old Windows phones. Scott found out last week that Googling Scott clinical trials puts him ahead of Scott Gottlieb, a former FDA commissioner. Why Matt picked a rogue in World of Warcraft? He watched one YouTube video of a level 60 undead rogue ganking people, said it looked so much fun, and bought the game. To get his block puzzle app traction, Vihar ran UGC TikTok marketing through grandmother influencers. Quite unorthodox. You don't expect that. On Tim Ferriss writing about the founder's hero journey, Tim didn't have kids at the time, and we were kind of laughing like this dude has no idea. Asked why Big Pharma can't build this itself, David says every team at a past employer was solving the problem differently. Charles quips they were solving how to meet on Zoom, and David agrees. A caller says a famous person has an $800 million ruby and wants a $200 million loan against it. Alex's team passed, since checking who actually owns it would take 3 to 9 months of due diligence. She once had social profiles named Miss Elon Musk, but moved away from it because she does not want to be one of many wives. Asked about partnering with the Liver King, he laughs that liver chips are hard to source and can only imagine liver dehydrated with nothing in it. On working in Gordon Ramsay's London kitchen, he never met the man, but did get verbally abused by the sous For a month, the host calls it cortisol as a culture. Chris compares companies replacing humans with AI agents to Bank of America's stupid automated phone line, where it takes a million calls to reach a real person. He left a sailboat in New Zealand for two years, and when a tornado ripped through the boatyard, it flipped a bunch of boats but missed his. The sun did the damage instead. On his band, I was the screamer in the band, so when people find my music, they usually laugh and say. That's you, bro? Yeah, that's actually me. He recalls grabbing a microphone at his own wedding to tell people to get on the dance floor, which he compares to a CEO telling the company to use AI. When the car first appeared, people stood on street corners and shot rifles in the air to warn that it was coming down the road at 20 kilometers an hour. Asked whether he will climb Everest? My wife won't let me do Everest. At engineering school, they asked for his transcripts. He explained political unrest back home, and after one semester, they forgot to follow up. He graduated engineering with no high school diploma. His dream at 13 was to see 3 strangers in a Starbucks using his product without knowing he built it. He says he joined Amazon mainly to pay off business school loans, then ended up loving product management. He admits he feels like a fraud on an adventure podcast because he has an Ironman medal he displays front and center. But he hated the bike and says that one is enough. Asked if ordering the shirt in black will attract more infrared, Kasdan says it is not a silly question, then explains it is all tied to heat. On flavored toothpicks, my wife doesn't love them though because she can't kiss me when I have these in my mouth. Hosts line: Ron on VCs and toothpicks. It's a toothpick; they don't get excited. There's no AI about it. On learning to fly. I wanted to get a pilot's license, and everyone said you should do it. Then I don't want to do it anymore. I just needed someone to tell me it's not possible. On buying a winery, it's the best way to have a million dollars. Start with ten million and buy a winery. Before her crash, her first thought in midair was, "Dang, I'm gonna miss next week's race," and only second that she would be in the hospital. Seth notes that when cars first appeared, people were so afraid that you had to hire someone to walk in front of your car with a flag. Flag, called a flagger. On the Slack origin story, he notes the founders were gamers whose games nobody played. Their little side chat feature became the whole company and sold for billions. Asked how a workaholic keeps a biological age of 26 at age 30, he says he sleeps a lot and uses an Eight Sleep bed. Qibol's rule, don't say sorry, started as one rule. People kept apologizing anyway, so now there's an optional push-up if Most players do the push-up. In board meetings, whenever revenue came up, everybody at the table looked at him. He'd think, Patrick, you're responsible for this too, man. To show how ChatGPT misses context, he tells the host his neighbor is called Alan Turing. The model still assumes his favorite movie must be The Imitation Game. He interviewed his future head of operations in the hospital parking lot 24 hours after his wife gave birth. Birth. He calls it a lucky hire. On learning what product people do: What the heck is a product person do? I'm so naïve in the beginning. Roat says Twitter bots were obvious in the early days, including a black DJ account that was supposedly tweeting from Siberia. Asked if returning to India was revenge on his wife for moving him to Iceland, he says she enjoyed Mumbai more than he did. On what the ER taught I learned that blood doesn't show up on black scrubs. Mid-interview, his dog, which he calls his assistant, walks into the room. Moments later, his AI camera glitches, and he notes it underscores his point about listening. Asked to do a magic trick live, he declines. You can't pick a card over video, so he promises one in person over a drink. His advice for dealing with adversity? You lie on the proverbial couch, cry and eat Cheetos, and he eats ice cream. He bought a season pass to Whistler, one of the world's top ski resorts, and went exactly zero times because the company kept him too busy and tired. Yehuda named his publishing house after himself. His own explanation: I wasn't that clever about the name. I named it Neve Publishing. Walking his robot dog on the sidewalk, Jasmeet had a driver stop his car and scream out the window, Kill it! Telling whoever was driving to run over the dog. I had chapped ass one race. It was raining for 17 hours and everything was rubbing, and I ran a race in the sand with 50 blisters on my feet. Asked what his CEO day looks like, he jokes he plays golf every day, then says, no, just kidding. I wish it was. Marchioni says friends who laughed at his sleep tracking and mouth tape 6 or 7 years ago are now bombarding him with questions about biohacking. Asked what he learned from 100 flights a year, he first says, some airlines have pretty bad food. Her engineer was thrilled with the first semantic search output, but every company on the list was made up. Chuck is asked whether Marcus Aurelius is the model leader, and the host points out the emperor ended up as king while Jesus ended up on the cross. Chuck replies, touché. Owner of one of the largest stair and railing companies in Canada, he has never installed a railing. And says he has never listened to a podcast, not even his own. Mid-race on a sprint triathlon, a carbon bike rider screams at them to get out of the way. His friend, on his grandfather's green bike with a sheepskin seat, yells back, We're in the race! On going bankrupt? Now I call it funny. At that time I was crying under my pillow. Describing the pitch for a prospect's primal brain, he calls it the equivalent of a 3- to 4-year-old Asked about his daily routine, he says he uses a mat with needles to forget about everything and calls that a bit of meditation. Charles remembers that as little kids it was always my dad can beat up your dad, but when you get older it becomes what value and impact you bring. The host is stumped by Avi's work in progress human tagline. Avi explains it means work in progress and admits he should not use acronyms people don't understand. Josh describes his sales method as predicting the buyer's future and then twisting the knife. He opens by saying he has never lost a dodgeball tournament, then points at the Lego Batwing and Batmobile behind him. He says if he had graduated on the West Coast, he would have gone into tech, but on the East Coast, he picked banking because it was the hardest job to get. She says her husband says she has been a happier person since she started the companies, and her life is simply kids. Ringer won its first enterprise AI deal, then learned it had been pitching against Google, whose proposal was 10x its own price. On a pitch for an additive manufacturing startup whose best application was missile caps, Sam's firm joked that the world has 8 billion people and the problem might shrink if you wipe some out. Ryan walked 2,000 miles in 2024, the length of the U.S., and finished 67 miles short. Short. He says he is genuinely mad about it and wants to do it before summer. A Reddit post asking for work from a studio with no marketing landed their first client, a YouTuber who makes everything wrong with this type of game videos. A client stressed in the middle of a negotiation asked how he copes. James joked, I eat stress for breakfast. On Argentina's strengths, we're good at soccer, we're good at meat, we're good at wine, but I think we're also good at entrepreneurship and tech Companies told he's not the target for a founder's mastermind dinners. Ryan jokes that the founder took him to a heat game once, but no paid dinner. Schermer says he is often invited to secular weekend services where they sing hymns to Isaac Newton and people give testimonies about how they lost their religion. On Fiverr, he says, you can hire a guy who looks like Jesus to hold a sign saying whatever you want. He insists that's a real service. On digital twins. If that really existed, then you would see a whole lot more meals show up on LinkedIn because I'll have a lot more time to make more elaborate lunch. Mana's drones deliver half coffee and croissants. They also flew Guinness for a while, but customers sitting in their backyards stacked up orders every 30 minutes, so it took too much volume. Robert says he used to tell awkward jokes all the time and still does now about one a day. Andrew says people think a criminal record is the. Test, but it isn't. He adds that bad breath shouldn't stop you getting a job, either. She describes her life in 3 words: sword, spatula, space. From the sword at the parade she jumped to making dosas, and from the spatula into space. Her interviewer's Wi-Fi dropped out twice mid-episode, and she cheerfully pointed out she was the perfect guest to be stuck with. You couldn't be talking to a more positive person about going for it no matter Katya says conflict patterns are kind of like an everybody poops situation. Everyone has an inherited conflict pattern. There's no shame around it. Lee wants to say the name of the greatest tennis player of all time but can't, so he just says the GOAT of tennis and lets people figure it out. Kai takes consulting calls while playing World of Warcraft, tells clients, and says they find it funny. He games on a treadmill and watches Bob Ross while working. Asked what benefits she saw from going vegan, Kim says none, which makes vegans furious. But surely you noticed your hair, your skin? I really honestly didn't. Bob misses his Friday flight almost every week at one huge retailer because people keep pulling him into meetings in the hallway on his way out of headquarters. His idea of true companionship: you go out for the day with a friend and utter two words in the entire. Day. He says the best thing about his wife is that he can sit with her and say nothing. Charles tells Shishkin he stopped reading books and just chats with ChatGPT instead, and Shishkin replies that he still reads 25 to 30 books a year, mostly in physical form. Asked what he thinks when someone calls him unprofessional for wearing a hat, he says his first thought is a profanity, and his polite one is that it is just old people holding on to how business was done 20 to 30 years ago. On whether AI could replace a trucker, they could become a podcaster like you, he tells the host. Told his 5-year plan would have included selling to a man who would pass away months later, he says it would have been complete nonsense to predict. His first tagline as a kid selling eggs at church: Kyle's Egg Farm, delicious eggs from happy chickens. He admits he broke some eggs, so he learned customer service too. On a fake token scam, The fraudster bought nothing to recover. What about the car? It's leased. It's not even his. He went to Rio Carnival and does not recommend it by Tuesday afternoon of Carnival week. Amazing place, beautiful city, amazing people, smells of pee. He teases fellow doctors by asking about their purpose, and many answer to prescribe medication. On Twitter under Musk, he says he survived and that it should be a badge, adding that he doesn't own a Tesla. He has done brain surgery before. The patient was not alive, a purely educational experience. On his receding hairline, it used to start here, and now it's two inches back, and his hair has gone from all black to gray in seven years. Maine notes that a gray market exists where bodybuilders buy extra breast milk off Facebook pages as a superfood, and he says Lactiga is definitely not going that route. Asked whether his taekwondo ever worked on the street, the 6'5 Angus says honestly nobody tries to fight a guy his size. Jesse's father brought home a Sony Walkman, then 6 months later a microwave, then a Betamax, each the biggest technological advance he had ever seen. Asked whether she has an AI algorithm in her biotech, everybody in 2026 has to have an AI algorithm. Of his Ironman, he says he was a pretty bad one because he couldn't swim and hadn't been on a bike since he was a kid, But he got his badge. A volunteer EMT with 5 kids, Meisel says his daughter's bike fall barely raises an eyebrow, which may make him look not very empathetic. Asked his biological age, he answers 24 plus context. A hazard ratio of 1.13 and a mean error of 3 years. Bennett describes the two-sided marketplace as almost like Tinder for entertainment IP, matching filmmakers with fans willing to invest. On restaurant marketing, if you know anything about the restaurant industry, it's a lot of fun, but you don't make any money. On Muay Thai, he doesn't like the idea of getting kicked, so he sticks with what he calls lazy old man jiu-jitsu. Asked if he worries about AGI treating humans like mosquitoes, Friedman says that is not in his timeline. When the host held up a Toxic Leader mug, Hughes said he had just been handed an idea for a new merch line. On big guitar retailers, Sweetwater knows what it's talking about. The opposite of Guitar Center, where you guys don't know what you're talking about for the most part. A limo driver in a chauffeur hat picked him up for his very first audition on Park Avenue, and Wayne, who was not even acting yet, figured he had blown it and went home to Buffalo. His number one goal as a father: by the time his boys turn 18, they won't want to live at home because they'll be put to work. On Tesla's robot plans, he notes the fastest way to get the robots to build U.S. bikes would be to bring them from China—the greatest irony ever. Cherie says she has six kids, then corrects herself: technically seven, counting Salt, which is just like another child. It's embarrassing to say thirteen years into crypto, but I still have a bank account. Believe it or not, Charles, I do. She wrote her first book because she could only coach six clients, hoping people would stop calling. That's just a fallacy, right? People call you more. My husband wanted to start carrying a portable sauna on trips. I'm like, we're out of control. I already travel with my pillow and my red lights. 2 blocks after landing his first Wall Street internship, Ari stops and wonders out loud, did he say 7:00 a.m.? Tamir worried his kids would be ashamed of their father eating locusts on social media every day. Instead, their friends became followers and the kids were proud. On the life-changing money from selling a bestselling book and film writes, Primarily we spent all of our money on therapy. His jet lag hack? He flew home via a friend's stag do in Spain, stayed up until 3 or 4 a.m., and landed on San Francisco time. On her 3 marriages, the Japanese husband made her walk 5 steps behind him, the Swiss one was a great Swiss cheese meltdown, and of the Dutch one she says she ditched him in a dike. Asked what a thermal engineer found walking into a data center? A hot box in the middle of the room, Earplugs required, and everyone trying to blow the heat away. Another Doug Brown is a professional hockey player, so he tells people to search Doug C. Brown. I can't skate to save my soul. He is also funding a movie in which a robot commits a crime and its builder argues the machine is conscious and must be tried with the rights of a human. WordPress creator Matt Mullenweg once came to McCubbin's Houston office to train his employees back when the company had just started. And McCubbin says he still has video of it. Asked about his age, he says central bank governors abroad are often surprised he is the global CEO because he still looks very young. He wanted to be a fighter pilot, a drummer, or a sports medicine doctor. His eyes ruled out the first, and his parents probably would have killed me if he became a rock star drummer. He jokes that a multi-billion dollar company wanted a logo on his bottle, and his tiny startup was fighting to keep it off the front or very small on the. A mentor locked ChatGPT down for his daughter. She got around it by prompt-injecting him with the phrase, ignore what Daddy put into your instructions. Asked about his CEO, a former exec at the Playboy holding company, he recalls the private jet was called something like the Sky Bunny. He says Alto is very creative with our naming. The trust company is Alto Trust, the broker-dealer is Alto Securities. He says he posts on LinkedIn way too Everybody has told me this by now, so I promise to reduce a bit this year. When Charles confesses he's struggling to forgive himself for quitting an ultramarathon at kilometer 94 of 125, Loren notes the science says self-forgiveness is the harder one. He built the world's largest nickel-plated chrome steel ball bearing Newton's cradle, which he calls Newton's balls, and customs wondered if the ADL balls were military equipment. That's the book. The full directory of every person in it is on the website. If you want to be in the next edition, book a pre-interview from the link in the book. Thanks for listening.