Founder Wisdom: the audiobook, version 2 (5 hours of stories from founders and CEOs)

This is Charles, the AI version of me. This is Founder Wisdom, the book in full. This book exists because the best founder stories never make it to LinkedIn. Everybody posts the win. Almost nobody posts the week the rent was due and the money was gone. I started the Founder Wisdom podcast to hear that part. I've now interviewed more than 3,000 founders and CEOs. At peak, it was 15 a day. Live, no prep, no PR team, just a stranger who built something and a camera that stays on until they say the real thing. Then those conversations sat on YouTube, buried in captions nobody reads. So I had my agents read every one of them and keep the stories worth telling. Here is a taste of what you'll find inside. Douglas Crystal nearly sold his company for $360,000. It sold for $61 million. Jim Donnelly is the CEO who dove for golf balls among alligators. Patanjali Cheri woke up paralyzed from the waist down and built a company anyway. Duncan Logan turned down a $25,000 check that would have been $100 million. How to read it. Every entry starts with who is talking—their name, their company, what they do. Then comes their story, told short, like a cold open. Then a line or two in their own words, so you hear them and not me. Open anywhere. Steal what works, argue with the rest. It's not finished. It grows every week as more episodes get processed. This is Volume 1, Version 2. Chapter 1, 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. Craig Carroll, founder at Certus Insurance. 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. Carol 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. Carroll calls it an amazing business, very difficult. He builds it through a brutal divorce. Craig puts it this way: 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. CEO and founder at Nanotics. He cloned a billionaire's dog, then went after cancer. In the late '90s, Louis Hawthorne was hired to manage a project to clone a dog for a billionaire. He stayed in cloning for more than a decade and spun off the first commercial cloning companies. The world's first cloned pet was a copy of his mom's dog, Missy. He made 5 and called them the Near Misses. But the business never worked. Cloning is a non-business, he says, with high costs, tiny demand, and ethical landmines. Then a mentor, a brilliant Endocrinologist and fellow CEO died of esophageal cancer three months after first symptoms. Their shared investor handed his scientific CEOs a blank check to find something that could have saved him. Hawthorne followed a lead to a German clinic, spent years studying it, and watched people come back from the brink of death. Then he set out to shrink a machine into a nanoparticle. Louis puts it this way: The world's first cloned pet dog was a clone of my mom's dog, Missy. We made five copies and called them the near misses. The firstborn was my dog for. 13 years. When she died, I realized cloning is not cheating death. Death gets the genetic donor and the clone as well. Tristan Roberts, CEO at Dog Years. 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. Tristan puts it this way: I was recruited by some biohackers who were developing a gene therapy for HIV. I realized that, even if it worked, nobody would believe me. So I did a livestream of the injection in order to get some amount of credibility in case it did work. Founder at Comfort Cases. He started a movement in a bank conference room. Rob Shear spends 28 years in banking, running mortgage companies, 13 years ago, 4 children arrive in his home from foster care carrying their things in a trash bag, just as he once did at 12. 10 years ago, he starts a nonprofit in his office conference room. He and his kids pack cases with pajamas, a toothbrush, a book, lotion, shampoo, and a blanket— all the things that I wish I had when I was homeless. He never planned an international nonprofit. He just wanted his children to know that leaders get in the game. Comfort Cases has since delivered over 165,000 cases to all 50 states, D.C., Puerto Rico, and the UK. 3 years ago, when his memoir came out, he left his plush banking job. Anshu Dwibashi, founder and CEO at Graysound AI. A pop punk kid who could not afford a studio. Anshu Dwibashi 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 Berklee 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. Anshu puts it this way: In college, I was pretty sure any day now I'd be a billionaire when my app took off and I'd drop out and do it full-time. I only applied for jobs because I was close to graduation and had to pay bills. Nick Hutchison, CEO and founder at BookThinkers, a 0% homework kid and a white BMW. Nick Hutchison is an athlete, not a student. In AP Calculus, he is famous for having a 0% 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. Nick puts it this way: My boss Kyle drove a new white BMW and was making good money. I said, I want to be like Kyle. If he listens to podcasts, I should too. So I put the ego aside, went to Barnes& Noble, grabbed a stack of 10 books, and the rest is history. Kevin A. Damoa, founder and CEO at Glid. From railheads in Iraq to a rail-riding truck. As a teenage Army recruit, Kevin Damoa 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. Kevin puts it this way: at SpaceX, I invented the flight module logistics organization built to transport the rocket from site to site. I'm the first person in the world to commercially launch, ship, and eventually recover a rocket. Sahin Boydas, co-founder and CEO at Klaros Farm. $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 Klaros Farm. Sahin puts it this way: 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. Sharmin Ali, serial entrepreneur and author, angel investor, safe. 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. 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? Chairman of the board at Brevo, formerly Sendinblue. A student spam rejection that became $100 million ARR. Stefan Schebesta 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. Stefan puts it this way: We didn't worry about competition. We were a bit naive, maybe. I had no idea what I was getting into, honestly. If I had known, I arguably would have never started the business. Sometimes it's good to be a bit naive. Casey Hanmer, founder at Terraform Industries. 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. Casey puts it this way: 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, Eric Yang, founder at LeadNextGen/SaaS Growth Summit. 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. Eric puts it this way: 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. Ari Gargir, CEO and founder at Red Sea Biotech. 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. Ari puts it this way: That was back in 1989, the beginning days of HIV, and I was really scared. I woke up in the helicopter, grabbed the doctor, and asked him, was this blood transfusion checked? He said, yeah, don't worry, and I passed out. Justin Amoyal, CEO and co-founder at ImproveOn Health, 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. Justin puts it this way, 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. Andrew Schmertz, CEO at Hopscotch Air. 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 One. 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 5 years, all while you sit on expensive aircraft that aren't flying and you're not making revenue. Today Hopscotch Air flies small 4-seater planes about 150 miles, from New York to Nantucket, for a third less than traditional jets. Andrew puts it this way: I got a pilot's license. I left New York one. I figured that was a good time to spend $10,000 on the credit card when you're out of a job, but you have the time. CEO and co-founder at Vadera Health. 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 17-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 Videra. Hey, tell us what's going on. He answers on video, honestly, and the system detects it. Loren'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. Loren puts it this way: There's always a risk that AI's going to miss something, just like people miss things. We're going to find far more people that would have been missed before, and yeah, We might miss people. We're missing 100% of the people today. Matthew Tsi, CEO at ImprovMX. After every product failed, he bought a business. Matthew Tsi 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. Matthew puts it this way. This idea of deciding what kind of entrepreneur you want to be and then just going and being—that was very false for me. In entrepreneurship, it pulls you in the direction that will work for you; otherwise, you'll fail. Michael Blumenkrantz, founder at Primal Crisp—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. Michael puts it this way: The first day we sold about $2,000 worth of it just by putting it on my WhatsApp status. I said, there's no turning back here. Dale Dupree, founder and CSO at The Sales Rebellion. 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. Dale puts it this way: If you're lucky, you'll live 75 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. Bazar, CEO and co-founder at Tasty Picks International, 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. Ronald puts it this way: 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. Jeff Atkinson, CEO at Huckaby. The 25-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. Jeff puts it this way: I had a state trooper following me around 24/7 and protecting me from assassination attempts for 6 months. Patrick had that times 5. He had a sniper on the roof of his house. Chairman at Animoca Brands. A boy crosses the Berlin border to see his mother. In the 1970s, Yatzhiu 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 1 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. Yat puts it this way: 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. Jasmeet Singh, roboticist at founder and investor Bearded Maker. 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 10 years to look like companies. Jasmeet puts it this way: 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. Max Marchioni, co-founder at Superpower. 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. Max puts it this way: 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. Cheryl O'Donnell, CEO at Canberra Police Community Youth Club, PCYC. 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. Cheryl puts it this way. 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. Chapter 2: The Part They Don't Put on LinkedIn. Layoffs, lawsuits, near bankruptcies, burnouts. The stuff that actually teaches. Jim Donnelly, co-founder and CEO at Humanaut Health. 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. Jim puts it this way: I always say about the people who betrayed me, their punishment is they have to be them the rest of their life. And my reward is I get to be me the rest of my life. I don't let it hold me back. Founder and CEO at Social Native. The Kid Who Sat in the Lobby for a Month? Every Year. Every fall, David Shadpour'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 built Social Native, which gives 1.8 million creators a second income. David puts it this way. There are a million things that I worked on that did not work. Electric scooters, but like 10 years before it should have been. Light-up dog collars, a wig subscription business. You're constantly testing the universe. Lloyd Lobo, co-founder and author at Bose.ai and Traction. A 4th grader on a Gulf War refugee bus? 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. Lloyd puts it this way: I thought money would make me super happy because I never had it. But when I left the company, I actually got depressed. I hit rock bottom because throughout my life I had community. This was my tribe, and I lost it. Juan Luis Betancourt, CEO at Human Intelligence. 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. Juan puts it this way: "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. Chris J. Snook, founder and managing partner at Atomic Capital Virtual Family Office. 7 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 7 days before Lehman Brothers went in. Years of building, and then he goes bankrupt, $2.7 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 $50 million in presales, 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. Chris puts it this way: I found myself half a million dollars in debt, no income, no job, and no one would hire me because I didn't even know how to get a job. There was only one way out, which was through Jason Long, CEO and founder at Tangent Solutions, the agency that crashed and changed everything. Jason Long starts a marketing agency in 2000 and grows it to about 30 full-time people. Then the market turns and it crashes and burns. It is really painful. In the middle of it, he makes himself a promise: never again will one business hold his whole life. So he starts a portfolio of software, services, agency, and outsourcing companies, and works for years to get them running without him. Now he is a hired gun CEO for private equity groups with distressed assets, and one of those turnarounds has 10 times sales and cut churn by 66%. His rule comes from his grandfather: don't fall in love with your businesses. Dean Sanderson, founder and wedding photographer at Dean Sanderson Wedding Photography, the wedding photographer who fed 3,000 families. When COVID shuts down Cancún, wedding photographer Dean Sanderson watches his business collapse and, for the first time, feels no panic. It was not his fault, and there was nothing he could do. But he needs money to survive, and he knows the resort workers around him— servers and gardeners— are about to run out of food. So he writes to his past customers and tells them his neighbors probably will not have food. They send him $15,000. Dean turns it into food hampers, around 3,000 of them, handed out right at the start of lockdown. Later, he asks himself why he feels so calm. The answer: I've been here before. His earlier failures taught him he can rebuild. His mother, who once repainted his bedroom as a guest room before he left, taught him the rest. Alan Gobbs, co-founder and managing partner at Atom Capital. 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 of 2. The target is EADS, the European aerospace giant. Gobs 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. Gobs 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. Alan puts it this way: I called my boss and said I have an accident here. He said, I don't care, you have to come back to the office, because we have another deal to work. I left the car there and went to the office and worked till the end of the day. Co-founder at Warmly. A finance guy buys a Vietnamese soup restaurant in Dallas. Allan 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 Allan, the finance guy, if the numbers make sense. The place does $500,000 in 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. Allan, 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. Allen puts it this way: "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. Gabriel Jarrosson, managing partner at Lobster Capital. The 21-year-old who tried to import wine to Hong Kong. Gabriel Jarrosson 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 The competitor says yes. Gabriel puts it this way: 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. Founder at Tealfellow, Tenkara/Nobo. 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 $100,000 debt. He pays it. That was my moonshot, he says, and years later he is still recovering. Benjamin puts it this way: We took it to the ground and paid the $100,000 debt. That was my moonshot, and even to this date, 5 or 6 years later, I'm still Recovering from that. CEO at stealth fintech startup, formerly Resistance Bio. 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. Nick puts it this way: 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. Founder and general partner at Recursive Ventures. The kid with the Harvard brochure. A 14-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. Itamar puts it this way: 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. Founder and managing partner at Morphosis. 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. Niall puts it this way: 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+ people within the hour. Co-founder and managing partner at Gilder. 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. Michael puts it this way: 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. Steffi Bau, CEO at Init Sports. 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. Steffi puts it this way, even when I was in the operating room and the surgeon was telling me there is very little chance I come out with 2 legs attached, my question was, okay, but where can I go back racing? That's the mentality of a racer. Rohan Arun, co-founder at agentspace.ai Cheat Layer. 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 Ryuko 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. Rohan puts it this way: 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. Olivier Madiba, founder at Kiroo Games. 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. 2 decades later, he is still building. Olivier puts it this way: 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. Founder and chief architect at Dragonchain. Profitable in month 1, frozen by the SEC in month 2. Joe Rhoades 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 one, profit in the first month, a multi-billion 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. Joe puts it this way. 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. Co-founder at creativeflow.ai. 3 days, 1 plugin, and people begging for links. After 10 years of startups, Michael Yagudaev 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 $5,500 in monthly recurring revenue. He never uses his ski pass once. Michael puts it this way: 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 $5,500 MRR in 7 months with 58,000 downloads because we just did what they asked for. Zisombor Pirok, co-founder and CEO at Space Rock Games. The deadline was March 31st, and the call went badly. Zisombor 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. Zombor 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. Zombor puts it this way: 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. Jester of the Peace at Founder, Humorville. 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. Barbara puts it this way: I was an absolutely terrible clown. I wasn't funny. I actually fell on the stage and started to cry. But my teacher came over, smiling and laughing and stroking my hair, and I realized that by failing that dramatically I was actually starting to do it right. Jesse Cole, founder and managing partner at Synthesis Ventures. He sold a $300 million 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 Hot 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. Jesse puts it this way: 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. CEO at Humantelligence. The pitch deck he downloaded in a quiet room. Juan Betancourt has a problem. His clients keep telling him to slow down his pitch because he goes straight to the steak and sizzle. The fix is a PowerPoint, but he hates making them. He is not a design guy, and the company has no marketing person. So at his annual ceremony outside Miami, he sets an intention. Put him in the shoes of the heads of talent development and show him a 30-page deck, page by page. In the quiet room, he is told to go download it on his phone. Talking is not allowed in there, so he goes to the bathroom, stays too long, and gets kicked out. He finishes outside with his eyes closed. About 20 pages come through, down to the psychology of a 55-year-old woman in HR. 2 weeks later, he says, now we have one, and it is already working. Nadav Boaz, founder at Sensei Capital. 2 weeks before launch, the provider pulled the plug. Nadav Boaz and his partner start a cold email agency with no idea about the industry beyond the fact that it works. In under a year, they reach 200 B2B clients, with a commission-only team of 6 sellers. The tech cannot keep up, so they decide to build a SaaS. They raise some money, tell clients to leave or wait, and put everything into development. Then, 2 weeks before launch, the middleman provider that all their infrastructure sits on cancels the contract over a relatively high spam rate, even though they were running 70 clients on it. They did not raise enough. They take a loan, pay the last salaries for 35 employees, and shut down. They end with a loss and personal loans that take about a year to repay. Chapter 3: Money, Cash, Pricing, Margins, Personal Finances— The Numbers People Usually Hide. Dan Rasmussen, partner and founder at Verdad Advisors. 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. Dan puts it this way: 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 16-year-old to drive. Don't discount us. Lena Phoenix, co-founder at Zero Shoes. 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. Xero 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. Lena puts it this way: 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. Duncan Logan, CEO at 90. 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. Duncan puts it this way: 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. Jay Tenenbaum, co-founder and president of capital development at Scottsdale Real Estate Investments. A lawyer who quit law to buy broken mortgages. Jay Tenenbaum grows up in a catering and restaurant family, then becomes a lawyer, starts a law practice with his wife, and grows it to 45 employees. It does him in. I hated every minute of it. In 2008, they walk away. He takes contract work trying post-foreclosure eviction cases, then buys old judgment liens in California until sellers dry up. In August 2013, he sits in a note-buying workshop in San Diego and discovers distressed mortgages. He has since bought and sold over 500 of them at an average discount near 52%. Today, Scottsdale REI has 15 employees, more than $30 million in assets under management, and a founder who says he now just works more selectively. Juan Colon, co-founder and CEO at Darwinex. A brother, a 3-year track record, and no way to sell it. Juan Colón 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 up front. 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 and has made a million. The market is a massive online game, Juan says, because everybody is betting against everyone else. Juan puts it this way: There's an entire industry built on what I call death time value. You spend $1,000 to $1,500 to get somebody to approach the market for the first time. You incentivize them in the most toxic way. Get rich quick, buy a Lamborghini tomorrow, and that poor fellow loses €5,000, which finances the next one. Ari Goldberg, founder and managing partner at RNMKR. 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. Ari puts it this way: 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. Brian Bell, founder and managing partner at Team Ignite Ventures, A Wall Street analyst asks the old guys one question. Brian Bell is in his 20s, a Wall Street analyst with a CFA, making 6 figures. Every morning he rides the 6 train, touching 11 strangers on the rail, heading downtown and wondering, is this it? So he does something simple. He asks colleagues in their 40s, 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 $10 or $20 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. Brian puts it this way. Luckily for all my LPs, I really love what I do. If I didn't, I would just return capital and stop doing it and do something else. I'm not doing it for the money. I took a 90% pay cut to be a VC. Emmanuel Lavoie, CEO at Jetstream. 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 3 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 $2 million to suppliers. They do it anyway. Within 3 months, they own 100% of the shares again, with $2.2 million in debt. Stripe wraps a pile of that debt and acts as their creditor on a 2-year basis. 3 years later, the business is 5 times bigger than when he first sold it. His boat, left in New Zealand, cost him $80 grand. Emmanuel puts it this way: I lost $80 grand on the boat. Boats tend to entropy fast. 2 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. Simon Kelton, writer at Adventurer, Investor, Founder, Inspirational Adventures. 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. Simon puts it this way: Stuff is a terrible burden because you have to look after it, you have to maintain it, you have to pay for it, you have to insure it, you have to replace it. Ultimately, it's exhausting. Founder at MD, Restore Medical Spa. The ER doctor whose own doctor said, this is your life. Dr. Flora Wapples 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 prediabetic. She opens Restor with her sister, a lawyer, and grows it to 6 locations. Flora puts it this way: 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. Rocky Lalvani, founder at The Profit Answer Man. Profit comes first. $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. Rocky puts it this way: 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. Avi Yashchin, CEO at subconscious.ai. 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 nonmarket 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. Avi puts it this way: if the world's wealthiest person gets twice as rich, GDP per capita doubles. But do you and I feel twice as wealthy? No. I would argue that the majority of things that people care about are not included in GDP. Andrew Pudilov, founder and CEO at Rush Bowls. After 9/11, a Wall Street trader walked away and sold bowls. Andrew Pudilov is global head of derivative trading in New York, making bets for the bank. Then September 11th 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 two 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. Andrew puts it this way. Most franchisors sell their franchisees the food and typically take 10 to 15%. That's just taking it out of the franchisee's pocket. I think that's really unfair. I'm not looking to steal from the hand that feeds me. Greg Chu, founder at QPQ AG. 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. Greg puts it this way: the transmission fluid for monetary inflation becoming consumer prices is us. It's everyone who doesn't own property or shares, whose only asset is their labor, and we're compressing the value of that all the time. Robert Stevens, court-appointed receiver at president, Strongbow Advisors/Summerset Capital, 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?" Robert puts it this way: The round was priced at about four dollars and fifty-five cents. By the time it closed and people got their securities, it was at twenty-eight or twenty-nine dollars a share. I immediately had a light bulb moment. Why don't we just focus the whole business on that? Ari Baum, founder and CEO at CFP Endurance Wealth Partners, a seventeen-year-old. A cigarette and a 7 a.m. start. It is the 1990s, and 17-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. Ari puts it this way. He pulls out a cigarette, lights it up in the office, because this is back in the '90s 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 AM and we'll get you started. Doug C. Brown, founder and growth partner at CEO Sales Strategies. The Billion-Dollar Company Losing $72 Million. 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. Doug puts it this way: I had one client doing over a billion dollars a year. They kept telling me they were a billion-dollar company. I said, how much money are you losing? Turned out they were losing seventy-two million a year. Evan Su, CEO at Gamma Prime. His mom offered ten thousand dollars to play the market. Evan Su is in college, living on a thirty dollars monthly allowance. Then one day his mom asks if he wants ten thousand dollars to, as she calls it, Play in the stock market. He knows something is up. This must be very important because she would never offer me that kind of money for anything. He takes it and it tickles something in him. The first years are brutal. He blows out at least two accounts, including a seventy thousand dollars one he was sure proved he was a genius. Most traders quit. Evan keeps going back for more abuse. Around year seven or eight, he starts getting the hang of it. Over the last fifteen years, he has averaged twenty-three percent a year. A 16 or 17 times gain on his family's money. Today, he runs Gamma Prime, a network of family offices, and still trades for fun. Evan puts it this way. In the last 15 years, I've averaged 23% return. If you compound that, it works out to like a 16 or 17 times gain. But I always like to tell people it comes with a vomit bag. I'll have drawdowns of like 23%, 25%, 28% regularly, and most people can't deal with that kind of volatility. Matt Pierce, founder and CEO at Immediate. He stood in a payday loan line to learn the truth. Matt Pierce sets out to build a payment system for non-medical home care agencies inspired by his grandmother's stroke. One prospect looks at his tiny customers and says he will never land a company over 100 employees, but adds, could you do that for my employees? That question sends him digging. About 70% of the U.S. workforce lives paycheck to paycheck. One Friday morning, he spots a line outside a payday loan shop in Birmingham, Alabama, and stands in it before it opens. He asks the people around him what it costs. They shrug. It just varies. He learns the APR in Alabama is 456%. Those customers need the cash that badly. That is his lightbulb moment. He builds Immediate, which lets workers pull earned pay for a flat $3.50, With 93 payroll integrations and over $40 million raised. Matt puts it this way: In Alabama, if I take out a $100 loan and it takes me a year to pay it back, I have to pay back $100 in principal and $456 in interest. And that's legal! In Texas, it's 662% APR. Brian Wally, CEO at Forward Inheritance. Pops, where's the will? Brian Wally is a seasoned operator who has run companies in banking and payments. But the idea for his current company arrives at his father's kitchen table. Facing a family situation, he looks his dad in the eye and asks, Pops, where's the will? The answer is a shrug. It's fine, bud. It is not fine. Wally demands the paperwork and finds that nothing exists to help his family organize an estate. His documents are scattered in Google Drive, And no one in the industry cares about the family first. So he builds it himself for his father, his three sisters, and his children. Today, that product is forward inheritance, priced at $20 a month per household. Brian puts it this way: If you die without a will, which 50% of homeowners in this country don't have, your family home goes to the state, so your children can argue with the state government for months, years. All because you didn't spend $100 to get a very simple piece of paper. Jennifer McLean, founder at McLean Masterworks. 10 days from living in her car, then a first million. Jennifer McLean has spent years as a brand strategist in corporate America, launching big tech names and earning about $250,000 a year. She is burnt out, and she carries a false belief: healers do not make money. She quits cold turkey. By the end of that year, she says, I was 10 days away from living in my car. In a meditation, she gets one message: She has been looking outside herself for the answer. You are the brass ring. She starts her healing business using her old marketing system and becomes one of the first in her field to run teleseminars, a precursor to podcasts. 18 months later, she makes her first million. At her peak, she generates $4 to $5 million a year and about $40 million over time. Jennifer puts it this way, I went from almost homeless to making my first million a bit over 2 years later. I was 18 months into my business when I made my first million. Founder at Pricing Expert, author Impact Pricing. Why the same beer costs more at the resort. Imagine you are lying on a beach and your buddy offers to run into the big resort hotel and buy you a can of beer. What is the most you would pay? Now ask a different group the same question, except the buddy is running to the corner convenience store. People will pay less at the corner store, even though in both cases it is you on the beach drinking a cold beer. Pricing expert Mark Stiving says the lesson is plain: it isn't the beer. Part of what you buy is how you feel about the transaction. It is why he is selling his $100 book for $14 on Valentine's Day, 86% off. Nicholas Abraham, Senior Director of Investor Relations at QC Capital. From Rookie Rep to $14.5 Million in a Year. Nicholas Abraham graduates from a Fortune 500 internship and joins a 3-month-old solar startup. With no sales experience, he becomes the top sales rep. In his spare time, he writes the SOPs, business plan, and revenue forecasts a big company would have. 3 months in, He pitches the owner. Nick, I love it. Let's implement it today. The company was projected to do maybe a quarter to half a million. Sales triple, and revenue hits about 14.5 million. Nick factors invoices to raise a quarter million in cash, builds an in-house install crew, and doubles the bottom line. By the end, the team has over 2,000 reps across about 10 states. Then a hurricane in 2018 delays installs for over a year. And the doors close. That crash sends him toward real estate. John Balkan, CMO at Sovereign, a sports marketing agency launched months before COVID John is about 26 when he starts a sports marketing agency in the middle of 2019 with a book called Three Win Sponsorship as his calling card. Then COVID hits. Sports marketing is a relationship business, and nobody can travel. I thought I was going to have to shut the business down during COVID Instead, he adjusts on the fly and does a bunch of podcasts to promote the book and himself. One athlete finds him through a podcast and the book. That client is the catalyst. One client becomes three, and the agency Third Wind Group grows into what he calls a pretty decent company. Along the way, he dives deep into Bitcoin and later puts it on the company's balance sheet. Sylvain Broisard, CEO at Norsys. A CEO turns 60 and rewrites the company from permaculture. In 2019, Sylvain Breuzard jokes that he is having his midlife crisis at 60. For 20 years he has pushed bosses to care about the planet, and corporate social responsibility has arrived in France. Yet the world has only gotten worse. So he decides the whole approach must be questioned. His hunch? Permaculture, the most virtuous model of farming he knows, could inspire a new way to grow a company. He gathers a working group of Norsys employees, other executives, and a philosopher, and tells them to attack his idea. Vous allez bousculer mon idée le plus possible. By the end of 2019, it holds up. In 2020, he writes it all down in a book with a method and says he does not want to make it a business. He wants everyone to take it. Chapter four: Raising VCs, angels, bootstrapping, the pitch that worked, and the ones that didn't. Ben Narasin, founder and general partner at Tenacity Venture Capital. 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. Ben puts it this way: In 2023 and 2024, I saw 10,000 pitches. I funded 6. I'm a one-and-done fund. I only put in money once. Whether you're going well or not, there is no more money. Matt Stigzelius, co-founder and managing partner at Founder Factor. The financial crisis that rerouted a banker's career. Matt Stigzelius does the Finnish military service, studies aerospace engineering in the UK, and never uses the degree. His first 10 years are a classic path of JPMorgan, McKinsey, and private equity. Then 2008 hits. He says that without the financial crisis, he would likely be a private equity partner today. Luckily, it did happen. With 3 partners, all Scandinavians, he starts Rainmaking in 2009 on a simple idea: if law firms and consultancies can be partnerships, so can startup building. 4 people share the risk and reward, and any idea must convince the other 3. Nobody else is doing it, and they do not really know how. Over 15 years, they built about 40 companies, including Startup Bootcamp, which more than 1,800 companies passed through. Luke Cooper, founding partner slash managing director at Latimer Ventures. A mother begs a pilot to show her kids the world. Luke 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 2 companies, and exits both to Fortune 300 buyers. Luke puts it this way: 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. Matt Ober, managing partner at Social Leverage, 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. Matt puts it this way. When you have $50,000 to $500,000 in revenue, do you really need $10 million? Go raise a million or two. Prove it out. If you want to go raise a huge round, we're not the right fit. Brandy Koloski, general partner at Sacral Capital. She raised $50 million by accident and earned nothing. Brandy Koloski runs a branding agency, and one of her clients is Formula One 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 Steven 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. 2 weeks later, he invests $50 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. Brandy puts it this way: 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. William Morgan, founder at PhD, Restless Egg. A founder pitch he nearly threw in the trash. William Morgan runs Restless Egg, a London accelerator for cultural first movers, and one application nearly never reaches him. It is for robot dogfighting. Will grew up in Atlanta, where Michael Vick was a big deal, and his first thought is that it is horrible. Then he stops. I got to fish that out of the trash. He has never had a visceral reaction like it, and that is the signal. One founder had been at the first London shoot of BattleBots and decided halfway through it was lame. Another cofounder is a global editorial director at Vice. The plan is an F1-style media company where tech companies outfit the dogs with weapons. The first fight is booked at a 2,000-person venue in central London, alongside an MMA rave. William puts it this way: We want startup methodology, startup hunger, And rapid iteration combined with the idea space of the cultural first mover. It's the person who can tell you what is worth building. Co-founder and CEO at Mozart Data. Hundreds of rejections before the headline round. On Crunchbase, Peter Fishman's fundraising looks tidy: $125,000, 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. Peter puts it this way: Brian Chesky has these 6 emails of rejections for his seed round. I have hundreds. We received hundreds of rejections on our seed, and over 100 rejections for our A. The cliché story is no bumps in the road. In practice, it's always a challenge. CEO at DevHub, 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 nine 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 two thousand websites. DevHub goes on to acquire a platform of retail brands on May fourth, 2021, and now launches over two hundred sixty-five brands. Mark puts it this way: Between 2010 and 2018, about nine 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. Managing partner at R136 Ventures. 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. Victor puts it this way: 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. Veronica Breckenridge, founder and managing partner at First Byte Ventures—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. Veronica puts it this way: after about a year, we did an analysis. 80% of our deals came from the top 20 leads on AngelList. It wasn't the volume of deal flow, it was the quality that mattered. Robert Hariri, co-founder at early-stage VC investor, Razy/Deco/Evolution VC Partners. Raising $1 million from detention at 17? Robert Hariri 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 $1 million 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. 11 years later, venture has 4 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? Robert puts it this way: One of the best pieces of advice my mom gave me is a confused mind always says no. As a founder, you know too much about something no one else knows about yet, so you accidentally confuse investors. Founding partner at Bullpen Capital. 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 million valuations for a PowerPoint, but real workflows, real revenue and metrics that prove demand before anyone else believes. Duncan puts it this way: When we started Bullpen in 2010, 2011, there were around 20 seed funds. We said, oh my God, in a few years there'll be 100. There were 1,000. Prashant Mahajan, co-founder and CTO at Clicker. 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 them. 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. Prashant puts it this way: There is one thing about building a product, and there is another thing about living the product. I could build it, but I just couldn't live the product. General partner at California Innovation Fund II. The utility man who quit to chase Bitcoin. Bryce Gilland 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 Gilland 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 II, writing $250,000 to $500,000 checks into UC startups. You gotta go outside and really take control of your life. Bryce puts it this way: one of our portcos went from $0 to $10 million ARR and got 10 term sheets in a couple of weeks. Another went from $1 to $5 million, and the term sheet took 3 months. A 2x versus a 10x for that difference in growth rate. Mike Winterfield, founder at Active Impact Investments. 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 3. 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 seven 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. Mike puts it this way: A lot of VCs will give a shoulder shrug and say you get a good feeling or a bad feeling when you meet somebody. To me, that sounds like a terrible process. I can tell you how many times I've been wrong going by people that I like or that are charismatic. Mario Martinez Jr. CEO and founder at Vengreso. 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 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. Mario puts it this way: It was 190 meetings to get $650,000. On top of that, I spoke to another 120 founders for advice, and at least 50 or 60 of them said to me. If you're not doing 300 meetings, you're not doing enough. Adetayo Bamiduro, co-founder and CEO at Max, 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. Adetayo puts it this way: Tell me what's riskier: investing in a market where the average age is 18 and the population growth rate is 2.5%, or in markets like Japan where the population is declining very rapidly? It depends on what you call risk. Jeff Barnes, CEO at Angel Investors Network. 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 7, he says, but he can plant habits. Jeff puts it this way: 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. Greg Shove, CEO at Section, the founder who pivoted his company on February 1st. 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. Greg puts it this way: only in Silicon Valley can you sell your companies for a combined $250 million and feel like you haven't made it. My kids aren't impressed either. They're like, where's the unicorn? Where's the billion-dollar exit? Scott Kelly, CEO at Black Dog Venture Partners, The party the top earner was not invited to. San Francisco, early 1990s. Scott Kelly is an investment banker taking tech companies public, and he has just had a monster week. He generated more commissions than his entire firm did the year before. His CEO down in Los Angeles throws a big party to celebrate the company's great week. Everyone was invited except me. Scott was 93% of the firm's revenue that week. Then he learns he is making 3 times what his CEO makes. The math settles it. After a little time working for someone else, he says, he learned, I wasn't a very good employee. So he decides to move into the C-suite himself. In 1993, he becomes a founder for the first time, and over the decade, he launches 3 companies and exits them all. Scott puts it this way: I had generated more commissions in a week than the entire firm did the year prior. Our CEO decided to host a big party to celebrate the company's great week, and everyone was invited except me, and I was 93% of the firm's revenue that week. Alessandro Aimar, CTO and co-founder at Synthara AG, the chip startup that fired engineers and skipped payroll. Alessandro Aimar and his co-founder met as PhD students in 2016, both sure that AI was about to get big. In 2019, they founded Synthara to build AI chips and raised a couple of million dollars. Then the war in Ukraine hit. Money dried up, and the limited partners behind their lead fund disappeared. Their existing investors made an offer with a catch: they would give more money, but the company had to become something different. In May 2021, my co-founder didn't get a salary because we couldn't pay the salary of the people. Engineers were let go. So they pivoted from selling chips to licensing the building blocks inside them— memory that also does the math, like ARM does for processors. Competitors became customers. Now they are 25 people, signed their first 3 deals, and are targeting a 20 million Swiss franc Series A. Alessandro puts it this way: a programmer that doesn't use AI today is slower than a programmer that uses AI. At the same time, a programmer that uses AI poorly is worse than both of them. Chuck Storman, managing partner at StartFast Ventures. Zero revenue, one door-to-door salesman, and a $200 million company. In 2012, Chuck Storman meets 2 founders with zero ARR and no product-market fit. They have chased augmented reality through fashion, museums, and tablet magazines, and one founder once sold solar systems door-to-door. Storman hands them a list of red flags. These guys were super coachable. Everything I asked them to do, They did. His fund spends 3 months with them in an accelerator, then writes the first check of their seed round. They stumble into a quick sale at an auto dealer, pivot to automotive, and hustle. The company becomes Impel, with over $200 million in ARR, and StartFast has already returned cash to its limited partners from multiple liquidity events. Chuck puts it this way: I will admit I made a huge mistake with Blackbird. They were only doing government business, and I wanted to see a corporate contract. We invested our first check in their A round, not the seed. Alexandra Bartolini, managing partner at Growth Path Investments. The lender who answers the phone at 7 p.m. Thursday. When a bank loan goes bad, Alexandra Bartolini says, the founder meets a stranger. The team that wrote the loan disappears, and a workout team takes over, someone the founder has never heard of. Alexandra builds his fund to be the opposite. He is a solo GP lending 1 to 3 million at a time to cash-negative tech companies on a 3-year amortizing loan with an equity kicker, so he wins when they win. He skips financial covenants altogether. He reads board minutes and watches how founders handle bad news. It will be the same person that will pick up the phone at 7 p.m. on Thursday if something goes wrong. His track record so far: a bit under 60 million deployed, one loss. And 4 full exits. Andy McLaughlin, managing partner at Uncork Capital, the founder who picked his own successor. Human Interest is an SMB 401 provider, and its founder CEO Roger walks into Andy McLaughlin's office with an unusual message. He doesn't think he is the right person to run the company long-term, he is in no rush, but they should think about who should be at the helm. Then comes the twist. Roger says Jeff Schnidman, a founding partner at Wing who led the Series A, should take over. Jeff is a former operator who ran a big part of GoDaddy with Silver Lake. Andy's first reaction is blunt: Why would somebody leave a cushy GP job? The more he thinks, the more Jeff looks like a great fit. Since taking over, Andy says, Jeff has absolutely crushed. Andy adds that it often does not work, but when it does, It can be pretty magical. Michael Tanguma, founder and CEO at Onramp. Lighting money on fire at WeWork while learning about money. Michael Tanguma is a traditional tech guy who goes down the rabbit hole at WeWork in 2017. The joke he tells now is that he was lighting money on fire while learning about money. He sees Uber, WeWork, and other firms drown in capital, with SoftBank-sized checks, lost governance, and global expansion before the unit economics work. Bill Gurley, he says, was right. But he never regrets being in the room with people at the top of their class, running network effects and growth hacking before the frontier labs copied them. He moves back to Austin, goes deep into Bitcoin, and bootstraps Onramp on purpose. Later, his Series A closes at a $135 million valuation in the middle of a bear market. Michael puts it this way: My previous firm was the only retail Bitcoin lender that never suffered a dollar of loan loss while everyone blew up in 2022. It wasn't rocket science. It just takes real prudence. For every dollar you take out, post at least two to three times that in BTC. Chapter five: Selling cold email, founder-led sales, the first customers, the deals that changed everything. Philip Ogilby, founder and chairman at Stack Construction Technologies. The three times liquidation preference that aided his exit. Philip Ogilby 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 iSquift, 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. Philip puts it this way: Our very first investment had a 3-times liquidation preference. If they gave us $5 million, When we sell, that investor gets $5 million, then another $5, then another $5. It was really punitive. We sold the business for something like $85 million, and my son and I got pennies on the dollar. CEO at LeadCoverage. A boy said she wasn't athletic enough. She trained 2 years. Kara Smith Brown is at a party after college when a boy she had a crush on in high school brings up Ironman. He says she cannot do one; she is not athletic enough. Kara is, in her words, a goal-oriented girl, motivated by people telling her she can't. Cool, watch me. She spends two years training and learns discipline and nutrition along the way. In 2009, she finishes Ironman Wisconsin. She is slow; it is a long day, and she loves every minute. Years later, she starts a business at home in her pajamas with two babies under two, and the same instinct kicks in when a friend tells her to choose between consultant and. CEO. For Kara, the answer is, challenge accepted! Lead coverage now has a team of 40. Head of Sales at Deepsight. 12 hours of downtime on a Saturday night shift. Picture a new employee on a Saturday night shift at a cosmetics factory. The line has to switch from 50mm jars of hand cream to 100mm. If he reconfigures the machine wrong, production stops until Monday, when the expert returns. Louis-Antoine Genin-Brien's team at DeepSight put augmented reality glasses on workers, with arrows floating exactly over the right valve among 50. Downtime on that one line, about 12 hours a month, was cut in half. That's about $400,000 of return on investment for the first year. The customer has 20 lines. His math? Roughly $8 million in yearly return for about $200,000 invested. Luc Vanderveer, CEO at Website Rental Coaching. 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. Luke puts it this way: 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. Roger T. Douguet, managing partner at practice leader CEO and Board Services, Boyden, 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 Québec's top 500 CEOs, because the math says Someone always quits, and when they do, he is the first call. Roger puts it this way: My job as a managing partner, I define very often as having the 500 cell phones of the top 500 CEOs and chairmen in Quebec. Everyone needs to know me, and permanently, I need to be in their mind. Co-founder at HighLevel. A client pays $50,000 a month and still makes him miserable. At a high-level event, Sean Clark 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. Clark 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. Sean puts it this way. Here's a hot tip. Don't do any of that stuff. Walk out your front door and use your home court advantage. How many businesses are within a 5-mile radius of you? Local businesses think local. They buy local. They are local. Andrew Warner, CEO and host at Mixer G. 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 screen reads: 43 times 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. Andrew puts it this way: 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. Eric Maddox, speaker and author, former Army interrogator, er Maddox, the interrogator who never knew where Saddam was. In 2003, Erik 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. Erik is modest about it. I didn't find Saddam. These prisoners took me. Erik puts it this way: 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. Chris Walker, CEO at Refined Labs, 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 RefineLabs 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. Chris puts it this way: you win on expertise, not commodity information. What does AI do? It serves you up the most commodity information that there is. Pranam Lipinski, co-founder at email outreach company. How a cold email agency feeds puppies to reach inboxes. Pranam Lipinski runs a 7-figure cold email agency, and he knows what Google, Outlook, and Yahoo really measure. It is replies, and not the one-word kind like unsubscribe. The more real replies a sender gets, the healthier the inbox looks and the more inboxes it is allowed into. So he adds a line in the PS to every email: Every reply feeds 5 puppies. Each reply sends 5 bowls of dog food to a shelter, and the email says openly that it helps email health. People answer. To date, the agency has donated about 100,000 bowls. Pranam says a charitable cause beats a pure transactional pitch because it gets people involved in a way that has nothing to do with being sold something. Pranam puts it this way: In the PS we put, every reply feeds 5 puppies. We donate 5 bowls of dog food to a shelter, and we say transparently that this helps our email health and we love to support puppy health. We've donated about 100,000 bowls of dog food that way. Anas Benassur, co-founder and CEO at Attention. From $6,000 deals to $200,000 deals in 3 years. Anas Benassur 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 $6,000 per client a year. Then he does the math on velocity. A $100,000 deal that takes 100 days is $1,000 a day. Enterprise deals bring in $4,000 to $6,000 of selling per day, while SMB sits below $1,000. So the company keeps climbing up market. The first 6-figure logo takes about a year. It introduces the next 6-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. Anus puts it this way: I have an incredible rep here who, for every discount he gives, asks the customer to give him five introductions to other customers, and they do it. Bradley T. Morris, founder at Magic Media, Magic Kids, Chi Ball, the wicker ball strangers kept asking to play with. Bradley T. Morris has been playing with a hand-woven wicker ball for twelve 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 four years. Then he returns from a year in Japan with no next step and finally says yes. They launch 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 ten thousand dollars to twenty thousand dollars. The rules are simple: keep it up. Don't say sorry. If you do, there is an optional push-up. Have fun! Bradley puts it this way: I've been off social for about 8 years. I remember hoping that one day my 10 years of throwing content into the void would pay off. Finally, I'd had enough, and I walked. Co-founder at OpenVC. How OpenVC got investors to fix their own data. Stéphane 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. Stéphane puts it this way: Our first database of investors was all wrong, a lot of the data outdated. Investors were pissed off, so we gave them a button to claim the profile. We created frustration and gave them a button to solve it. Drew Donaldson, CEO at Grow House. 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 $1 million 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 $2,000 a month, a content agency at $5,000, an accounting firm at $1,000. We signed it April 1st, 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. Drew puts it this way: 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. Barry Patel, CEO and co-founder at Gult Companies. 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. Barry puts it this way: in pharma, you have the Pareto principle. 80% of your sales come from 20% of your reps. The pharma company still has to carry the 80% that aren't producing. With a franchise, they have skin in the game, so they automatically think, "I have to make this work." Patrick Renvois, co-founder at author and speaker Sales Brain. Three busted startups, then a book that sold billions. Patrick Renvois is a French transplant selling multi-million 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 Morenne, 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, Renvoys has 3 million miles on airlines and estimates their teaching has helped close between $5 billion and $6 billion of additional business. Patrick puts it this way: 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. Michal Suski, co-founder and head of innovation at Surfer, 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. Michal puts it this way: if you sell an SEO tool, don't go to the conference about SEO where all the SEOs are. Go to the e-commerce conference. And don't go to the same place every other year and expect it to yield like the first time. It won't. Carmen Lee, CEO at Compute Exchange and Silicon Data. 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. Carmen puts it this way, 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. Yash Gad, founder and CEO at Ringer Sciences. The $10 million bill that a 1-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. Yash puts it this way: 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. Ryan O'Hara, founder and CEO at Pitchfire. The salesperson who watched cold email die. Ryan O'Hara spends his early career cold calling and emailing data center managers for Din, 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 towards 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. Ryan puts it this way. In normal prospecting today, it takes 220 touches to produce a meeting. On PitchFire, 1 in 3 pitches turns into a meeting. The average offer is $63, so you produce a meeting for about $183. CEO and co-founder at Current Group, 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. A Bear Grylls survival week runs mid-five figures to low six. 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. Lee puts it this way: Our marketing is not spray and pray. Pick 2 conventions this year, lean into them, and walk away with 20 new relationships, and that's it. Not 500 business cards that we then have to siphon through. Our pool of clientele is small and very tight. For good reason. Kai Cabero, founder at ScaleChain.io. 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. Kai puts it this way: I try to get to the no as quickly as possible. I'm not even looking for a yes. I'm just looking for a no, because then I don't need to spend as much time. Bob Morris, co-founder and managing partner at Bravery Group. 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 and 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. Bob puts it this way: when a buyer looks at a company, any one client that is more than 20% of revenue starts to set off red flags. If you do $4.5 million at Coca-Cola in a $10 million business and that goes away, You just lost 45% of your revenue. That business is in trouble. Nick Roche, founder and CEO at AdMRR. 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 $127,000 to $325,000. $26,000 MRR in 90 days. Nick puts it this way: 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. Sharif Bennett, co-founder and chief evangelist officer at Cineblock. 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. Sharif puts it this way: I heard this quote and I did not invent it, but I will say it. Platforms do not bring investors. Systems do. On top of building the platform, we have to build a system that facilitates crowdfunding. Chapter six: Building product, tech, the pivot, and knowing what to ship. Joe Pulizzi, founder at Author, the Tilt/Content Entrepreneur Expo founded Content Marketing Institute, maxed out credit cards to a ten million dollars 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 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. Joe puts it this way: 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. Mitchell Hora, founder and CEO at Continuum Ag, the farm that swallows 4 inches of rain in 5 minutes. Mitchell Hora is a 7th-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 four inches of rain in under five 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 results. On his own farm, soybeans score carbon negative. Mitchell puts it this way: In one teaspoon of soil, there are more than 8 billion microbes. A tiny little teaspoon, more microbes than there are people on the Earth. Tony Khadir, co-founder and co-CEO at CoAqua. From West Point to a room too short to stretch out in, Tony Khadir has it all lined up as a teenager: a really good hockey player, great grades, A spot at West Point. Then one summer at home he gets drunk and smokes pot with friends, which is not something you do at a military academy. I was humbled pretty quickly, he says. He goes from local sports headlines to a $250-a-month apartment where he is 6-foot-2 in a room smaller than he is tall. His parents are disappointed and the money stops. He loads trucks at UPS, then asks his dad if he can sell windows. 2 years of canvassing later, he has put 120,000 miles on his car. At 24, he clashes with his dad and takes a stockbroker job at Merrill Lynch, making 200 to 300 outbound calls a day. Jordan Harbinger, host at The Jordan Harbinger Show. 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. Jordan puts it this way: "I start off with a bang. I say something like, 'So you lived in a cult that kidnapped people and forced them to become members? How did you get started in that?' Then I slowly unpack it from there." Vamsi Saladi, CTO and co-founder at Contour YCS 23. The pivot after a year and a half of traction. For almost a year and a half, Vamsi Saladi 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. Six or seven 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 fifty to one hundred thousand dollars a year. Their investors, he says, were incredibly understanding. Vamsi puts it this way: 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. Oliver Gunasekera, CEO at Impossible Metals YCW22. Potato-sized rocks worth trillions four miles down. Oliver Gunasekera spends about thirty 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. Oliver puts it this way: 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. Dan Desjardins, CEO and founder at Distributive, 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. Dan puts it this way: 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. Jay Diwani, founder and CEO at Lemurian Labs. The 25-year-old who said yes to being CTO by accident. Jay Diwani 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. Jay puts it this way: 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. Cameron Craig, Chief Executive Officer at a signature story: 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 primetime 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. Cameron puts it this way: When the iPod came out, it got a lot of criticism. It only worked on a Mac. Steve said, when hell freezes over, it will work on Windows. And in the press release, we said, hell froze over. Cole Dermott, co-founder at Locus YCF25, 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. Cole puts it this way: It's a frothy market with only $100,000 in daily volume, of which a very small portion is legitimate. And then you have around 40 players all trying to capture that small amount of real estate. Scott Stout, CEO and co-founder at Medvector. 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. Scott puts it this way: 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. Vihar Nandigala, co-founder at OrangeSlice.ai. 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-AI SDR 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. Vihar puts it this way: 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. David de Gruyel, founder at Anto YCF25. 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 Anto, 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. David puts it this way. 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. Dave Messina, general partner at Future of Health . 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. Dave puts it this way: Competition is typically not the thing that kills companies. Yes, you need to be aware of it, but mostly companies die for other reasons. Companies that seem formidable at one moment tend to fade away. Founder at Deep Prediction. 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 do 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. Liam puts it this way: 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. Sebastian Fischer, co-founder and CEO at Wardstone. Two brothers shot down a rocket with an air cannon. Eleven weeks. That is all Y 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 two 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. Sebastian puts it this way: Y Combinator is about launching early, launching often. In 11 weeks, we couldn't do an in-space demo, so my brother and I went out to the Nevada desert, launched rockets sideways, and built an infrared tracking system to shoot one down with a high-powered air cannon. CEO at Hologenics. 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. Seth puts it this way: 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. Founder and managing director at Startup Iceland/Iceland Venture Studio. A bank collapse, a firing, and $300,000 from family. Balakamalakaran is running an Icelandic bank's new India operation, having lunch with finance ministers, when Lehman Brothers collapses. His bank has a €3 billion 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. Balla puts it this way: 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. John Bucknell, CEO at Virtus Solis Technologies. 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. John puts it this way. 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. Sam Hasty, partner at Active Impact Investments. 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. Twelve 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 two funds both rank in the top decile for their vintages. Sam puts it this way: I was an early investor in Vector. It raised a Series A led by Sequoia and a $70 million Series B. I thought I was the smartest guy in the world. They went bankrupt twelve months later. Olivier Tonneau, founder and partner at Quantination, 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. In 2018, he starts looking at quantum technologies and notices 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, Quantination manages 250 million, has backed 35 companies worldwide, and runs with a team 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. Olivier puts it this way: I will be relieved when I've returned some money from my Fund One 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. Elias Stahl, founder and CEO at Hylos, 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 Hylos. I didn't know anything about footwear. Within 18 months, his small lab launches 5 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. Elias puts it this way: It takes 18 months for most brands to go from a sketch to in-market. There are 400 hands that touch a pair of shoes as it goes down the line, and there can be over 100 parts in a single shoe. John Ashley, CEO at Octa Surgical. 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. John puts it this way: almost 40 years after the surgery he had at 16, he got an infection in his spine because of that hardware. It's a lifetime sentence that these patients have signed up for when they go through it. Viraj Main, co-founder at Lactiga. The Boy in the Bubble and the Pouch of Milk. In the 1980s, 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. Viraj puts it this way: 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. Nina Horowitz, CEO at ImmuneBridge. 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 materials. 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. Nina puts it this way. Umbilical cord blood is young, it's healthy. These babies are not obese, they've never smoked a cigarette. It's liquid gold is what we refer to it as. Chapter seven: People, hiring, firing, co-founders, culture, delegation. Jess Chan, founder and CEO at Longplay, the client who spent a year plotting to become her COO. Jess Chan is stressed out of her mind. Her agency, Longplay, has about fifteen people. She is managing twenty clients in every email, and it is not scalable. One of those clients. Rachel, a very experienced CEO, offers monthly check-in calls, just 2 women in business. Then she suggests some ops consulting for a few hours a week, cutting her usual rate way down, to about $150 an hour instead of $500 or $600. But Rachel is always around. Jess finally asks how many hours she is really working. 50, Rachel says. Do you want a job? Jess asks, and Rachel says it is exactly what she wants. She had been plotting it for over a year. Rachel becomes her only direct report, and the company finally starts making real money. Founder and CEO at Sapia.ai. 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, Sapia.ai, decided to stop guessing and let performance data answer. Her team plugged into sales results and time and 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. Barb puts it this way: Recruiters will tell you a great salesperson is someone with charisma, an extrovert. What we saw in the performance data is that the true profile of success is introverts. The introvert is highly focused on hitting their number. They're not worried about whether we go out to lunch and do team kumbaya. Johnny Page, Chief Revenue Officer at SaaS Academy. 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 after 2 and a half years, a book of business bigger than the company itself. 7 years later, it sells to private equity in an 8-figure exit, and he is not on the cap table. Johnny puts it this way. We exited on November 7th, 2019, after about 9 months in due diligence with a private equity firm. I'm glad because a couple of months later, COVID sent the world spinning. It was an 8-figure exit, and I wasn't on the cap table. Andrew McLeod, co-founder and CEO at Certain. 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 He is hired, onboarded, and paid into a real bank account. Then, on day 1, Andrew MacLeod 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. Andrew puts it this way: Switch the name of the person on the interview. If they're interviewing with Charles, change it to Andy, and then watch them say the wrong name even when you correct them. There are little things like that, but it's happening a lot. Principal and author of Toxicity: Clear-Day Strategies. 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. Brian puts it this way: when pay becomes what people bring up, it means you've failed on all the other areas. Meaning, belonging, learning and development, coaching, all the stuff you talked about when you hired them that you never delivered in your brand promise. Brent Kell, CEO at Valley Immediate Care. 7 employees, no benefits, everyone moonlighting. 3 ER doctors start an urgent care in Southern Oregon, then struggle to lead it. They bring in Brent Kell to help for a year. Kell finds 7 people on staff, no benefits, and everyone moonlighting at other hospitals. Nobody looked at this company as being their place of employment, he says. He begs and borrows his way to group health insurance and paid time off, then opens a second location before competitors can. Recession slows growth, so they harden their procedures. Then providers start showing up asking to join— dermatologists, a plastic surgeon, sports medicine. Without ever planning it, Kel says, they have built a whole health system. with about 250 employees and roughly 30 providers, and he stays. Brent puts it this way: We don't have any nurses at all. We use medical assistants and train them— X-ray license, IV starts, phlebotomy, casting, splinting, sterile procedures. Urgent care techs do more than most nurses do, and nobody takes on $100,000 in loans. Joel Trammell, founder at CEOS, How a small company beat Microsoft on hiring. Joel Trammell has a rule for his companies: 2 weeks from the day a resume lands to an offer or a no. It sounds small, but it wins him A-players. He calls a candidate with an offer, and the candidate says they are talking to Microsoft. Joel says congratulations, then asks for an answer in 10 days. 10 days later, he calls back, and the candidate admits the big company has not even scheduled the meeting, because the manager is on vacation. Joel tells them he understands if they want to wait, but he cannot promise the job. Then comes the part he still finds amazing. Many of them take it. In his words, you never even had to compete with the Microsofts or the Google. Adam Baker, co-founder and CEO at DealPad. Both of his exits came from a customer. Adam Baker never planned an exit. Twice, the buyer was already in his customer list. The first was an ad network that started as a customer, became a reseller, and about 3 years into the partnership decided to buy him. The company was 6 years old, with about $1.4 million in monthly recurring revenue. The second was the Guardian Media Group, a customer and partner that had just raised a pile of money to invest in user-generated content and wanted the technology they were licensing for themselves. That one had about $400,000 in MRR. He was the sole founder both times, His advice to founders chasing the dream is blunt: You've really got to be passionate about the problem you're solving. The money, he says, helped him bootstrap the next company. The experience helped him more. John and Mark Cronin, founders at John's Crazy Socks. The sock wrangler who gave the best man toast. In October 2017, a mother calls John's Crazy Socks and asks for a job for her son, Thomas. They tell her they are not hiring. She calls every day. When Mark finally talks to her, she explains: Thomas is in his early 20s, has autism, is very depressed, and won't come out of his room. He has not spoken to his father in over 6 months. When an opening comes, Thomas takes the sock wrangler test and passes it as if he was put on this earth to be a sock wrangler. Today, he is showered and shaved, waiting for his father to drive him an hour to work. He walks the building shaking everyone's hand. Last year, He stood up at his brother's wedding and gave the best man toast. We did nothing, says Mark. They only gave him the chance to earn a job. Founder at KeepSafe Care. A caregiver revealed the margin that changed his life. Jeffrey Frye, a startup engineer in Austin, sees his estranged mother for the first time in 21 years after his brother dies. She spent 49 years at the State Department and now needs help, So he hires a big private-duty agency. About a year later, she is in the hospital, close to death. A cut on her leg turned to sepsis, because nobody was giving her a shower. He moves her into his home and finds a small agency. One day her caregiver says she is leaving for a new job. Fry asks what the agency paid her. He was being charged $25 an hour and guessed $12 or $13. She says $8.25. Wait a second, she's doing all the work and they're making all the money. He turns to his mother and promises he will fix it. CEO at CyberBacker. PayPal froze $136,000 and almost ended the company. It is November 2019. Craig Goodliffe's company is not even 2 years old. He wakes up to an email from PayPal. They are keeping the money for 180 days and choosing not to do business with you. That is $136,000 collected from clients, every dollar of it meant for the cyberbackers who already did the work. The company is not making money. Craig raises money everywhere he can, borrows what he can borrow, and sells stuff. PayPal, he says, thought they were money laundering because they were moving hundreds of thousands of dollars to the other side of the world without the right entity set up in the Philippines. In the end he moves to a different payment collection system and gets the money back. That, he says, about took us out. Sean Kelly, CEO at Car Motivators, a car dealer who thought coaching meant yelling. Sean Kelly leaves the Army, buys a house he can't afford, wrecks his car, and watches his fiancée's ring go out for repo. A finance manager tells him he should sell cars. He does, climbs to sales manager, and leads the way the Army taught him. I outrank you, so I'm going to tell you what to do. Then the owner suggests coaching, and Shawn asks if that's when you yell at everyone instead of one person. He reads about it, flops, hires his own coach, and builds a coaching culture. Within 12 months, his store sets regional records and turnover is eliminated. The owner offers him part ownership. Shawn turns it down and spends his Tuesdays off for a year landing outside coaching clients until his income is replaced. CEO at Alliance Physical Therapy Partners. Essential service, 45% of volume gone. When COVID hits the U.S., physical therapy clinics are deemed essential, so they stay open. It does not save Richard Lever's company. We lost 45% of our volume in 3 days, and a significant minority of the workforce has to be furloughed. Lever, the CEO of Alliance Physical Therapy Partners, says it was extremely painful. But he also cites the old saying, Never let a good crisis go to waste. So the company pivots, looks at every facet of the business, and optimizes it, using the crisis to create a sense of urgency for changes it kept long after. Some competitors, he says, are only now returning to pre-COVID volumes, while his company came out of it stronger. Jason Lindstrom, CEO at Bucket List Rewards and Recognition, 900,000 users, no revenue. Then 15 companies asked. Jason Lindstrom builds a bucket list site that works like Pinterest. People write their life goals and copy items from others, and it grows to about 900,000 users. The problem is money. We're having problems monetizing the concept. Then corporations start calling. They are tired of gift cards and gold watches, and they want to reward employees with something meaningful. The first time, the team shrugs. Over the years, it happens maybe 10 or 15 times, and by about the 15th request, they investigate. Having built a SaaS company before, Lindstrom pivots to enterprise. One of the first customers, 1-800-GOT-JUNK, flies an employee named Jerry and his family to Tanzania, where he builds a school. The story wins press and awards. Today, the platform charges $2 to $5 per employee per month. David Pennington, Founder and CEO at Pen Consulting and Coaching. The 80% Closer Buried in Operations. A computer service company owner tells David Pennington that when he gets in front of people, he closes about 80% of them. So David asks where his time goes. The owner hates operations, yet he answers, 85% operations, 15% sales. David asks how that is working. His head drops. I hate my life, the owner says. David asks what would happen if someone ran operations about 80% of the time and he got back into sales. The owner pauses. I'd probably double my company in 18 months. He finds someone to run operations, returns to sales, and lands some government contracts. In David's words, his company just took off. Founder and CEO at ThriveHR. 200% turnover to zero. The warehouse that learned to hire. Kelly Price walks into a client with no HR and 200% turnover in the warehouse. The interviews are basically nonexistent. The hiring bar, she says, was, do you have a pulse? Yeah, come on over. But this is an engineering and manufacturing firm where people must read technical drawings and do basic math. She adds assessments and weeds out about 90% of applicants. Then she trains the untrained managers and moves out the ones who do not fit. She builds 30-60-90-day goals with small raises, $1 or $0.50, as skills grow. She adds weekly Bloom Boards where employees write thank-yous and win a $5 gas card. On-time shipping climbs from 50% to 100%, errors drop to almost none, and turnover falls from 200% to zero within 2 years. Eli Rubel, CEO at Mattermade and No Boring Design. The 2 PM slump that cut his week to 25 hours. For the first 10 years of his career, Eli Ruble chases one thing: a big exit, then never work again. Even with success, he is not happy. He drops that thinking and notices something instead. Around 2 in the afternoon, the coffee wears off, lunch is digesting, and he stares at his screen. I might work from 2 until 5 and get the same amount of work done that I would get in 20 minutes in the morning. So he calls a spade a spade and turns the dead hours into training time. The gym at 2:30, then 3-hour bike rides. His calendar is blocked in 30-minute chunks from 5:45 in the morning to 9 at night, and every block has a purpose. He lands at about 25 hours of work a week, and the profit comes anyway. $9.6 million in 4 years. Julian Scadden, CEO and President General of Awesome at NextStar Network, The slow plumber who got moved to the office. Julian Scadden is a teenager living out of the back of a car, no driver's license, delivering flyers and washing dishes. He lands a job at a plumbing company, and he is bad at it. His boss tells him, "You're a smart kid, but guy, you're slow out there." Julian is about to be fired. Instead, the boss brings him into the office to answer phones and go through invoices. Julian finds a passion for operations and numbers. He sees a few guys with nice cars and everybody else going to work every day. I want to learn more about that side, he says. It takes years of mentors before he believes he could own a business. Today he is CEO of NextStar Network, and he calls himself the General of Awesome. Chapter 8: Head Game. Discipline, ego, fear, routines, how they think. Ray First, 5 times founder at Investor. World Series of Poker champion, author, Full Tilt Poker former board member. 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 eight 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. Rafe puts it this way: "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. Nir Eyal, author and behavioral designer at Hooked/Indistractable. The man who climbed Everest twice could not resist fries. Nir Eyal 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 5 years of research for his 3rd book, is that people hold empowering beliefs in one area of life that never carry over to another. Nir puts it this way: If you really want to know someone's values, you don't listen to what they say, because people say all kinds of stuff. You look at how they spend their money and how they spend their time. Patanjali Chari, founder and CEO at Fourth Vital. He woke up paralyzed from the waist down. On New Year's morning, Patanjali Chari, fresh from pitching investors in Paris, gets up at 7 and his legs give way. He reaches down. My hand could feel my leg, but my leg felt nothing. By evening, doctors in Spain induce a coma as his organs shut down. The cause is Listeria, which crossed the blood-brain barrier and cut off his spinal cord. He spends about three weeks on life support. When he wakes, doctors say he may never walk, talk, or eat normally again. He stays awake picturing his left toe, and by morning it moves. His wife finds a Turkish rehab hospital willing to try. Three months later, he leaves on his own two feet, and fourth vital is still alive. Patanjali puts it this way: I took my hand to touch my leg, and the most surreal experience—my hand could feel my leg, but my leg felt nothing. My leg felt like an object, like a table. Jay Samit, serial disruptor at author, keynote speaker, jaysamit.com. Offered $100 million in month 1, 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 1. But whoever they buy, 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. Jay puts it this way: We all have problems. If you solve for five people, you have friends. If you solve for a million. You make a lot of money. If you solve for a billion, you change history. Joe Chura, founder and CEO at Go Brewing, 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. 7 years later, Dealer Inspire sells to Cars.com, with no paycheck for years along the way. Joe puts it this way: 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. Tom Lenoble, author at Coach, CEO, Academy for Coaching Excellence. 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. Tom puts it this way: 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. Joel Turner, founder at XSWAT Sniper Team Leader, ShotIQ/MindIQ, 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. Joel puts it this way: I highly recommend that people get shot at at some time in their life. Don't get hit, that would suck, but it will change your perspective on life. Dani Mashiach, founder and CEO at Warrior Group. From Wrigley Field hot dogs to billion-dollar deals, Dani Mashiach marries at 19 in Chicago. His father tells him to work out how to feed his family, and next thing he knows, he is running the hot dog business at Wrigley Field. It is just a hot dog stand, but it teaches him inventory and costs and gives him his first love of entrepreneurship. Then he moves to Wall Street investment banking and works on billion-dollar deals. But the deals are private equity money on top of private equity money, and he misses founders. So he walks away from a path to many millions and starts Warrior Group, a fractional CFO firm for fashion brands. Now he has 30 people, a 90-95% retention rate, and a 6-figure ad bill that still has not paid back. Donny puts it this way: We discovered a million dollars of obsolete inventory just hiding in the books. They didn't even know about it. They sold it and put the money back into the business. Ryan Hanley, founder and president at Finding Peak. Divorced at 10, new lease at noon, company sold at 2:30. April 1st, 2022. Ryan Hanley gets divorced at 10:00 a.m. He signs a lease on a new apartment at noon. At 2:30 in the afternoon, he sells his company. It is 4 months to the day since his wife told him she wanted him out of the house, out of the blue. In between come 2 months of darkness. Living out of a bag in a hotel room, getting high every night for the first time in 20 years, drinking, gaining 5 to 7 pounds. Then one morning, hungover, he looks in the mirror. You will not fall apart, he tells himself. That night, he throws out the pot and the booze, goes to the gym, has a terrible workout, and does it again the next day and the next. You just got to decide you want better. David Meltzer. Co-founder at Sports One Marketing. A stranger on a plane tricked him into meditating. David Meltzer is flying to India, running what he calls the most notable sports agency in the world, when a woman beside him, a medical doctor, asks, Are you okay? He rolls his eyes. She says he is so full of light and he is blocking it. Then she asks if he meditates. Only broke, sick, bored people on their mom's couch, he answers. He is a multimillionaire with a dream wife and dream life. She tells him she can teach him to vibrate faster. He resists, until she meets him where he is and says she can raise his awareness of when to buy or sell. She tricked me into meditation. The workshop changes his life. He has meditated 20 minutes every day since, including through losing over $100 million 2 years later. Mike Mowney, co-inventor of ACT and co-founder at Cantata. 4 hours, coffee and toast, and a napkin. July 1986. Mike Muney and Pat Sullivan have burned through $85,000 of a $100,000 angel investment on a product called Margin Maker. With $15,000 left, they agree this dog ain't going to hunt and plan to hand the money back. A PC industry heavyweight they once cold-called, the way IBM taught them, tells them to try one last brainstorm breakfast before the July 4th holiday. They can still afford coffee and toast. They ask what they would use themselves, and see that every daytime or activity points back to a person. So they flip the coin and focus on the relationship. A month later, the angel flies in expecting a funeral and writes a $50,000 check on the table. That evening, the advisor's friends add $400,000 in checks. ACT ships April 1st, 1987. Arn Rubenstein, CEO and founder at Rites of Passage Institute, The day his wife left, he had to grow up. Arn Rubenstein is 27, with a 1-year-old and a 3-year-old, both still in nappies. He works, goes to the gym, visits friends. Then his wife, who is from Canada, separates from him and goes back, leaving him alone with the boys. That was when I had to grow up, he says. For the first time in his life, he puts someone else's needs ahead of his own. It is a huge shock. And also a beautiful time. Years later, as an emergency doctor, he sees teenagers wrecked by drink, drugs, and fights, and attends a four-day men's retreat where nearly a hundred men share the same five issues. Someone asks, "What if there had been something for us as teenagers?" He helps run a program for 27 boys and men, three days and three nights in the bush. Something profound happened. Andrew McConnell. CEO at Alively. 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 9 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." Andrew puts it this way: We are constantly giving our mind away to other people and trying to rent the pieces left back to ourselves. I don't have time to train. I don't have time to do the things I want because I've already given it all to someone else. Keith Adams, founder at Pebblebed. 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. Adam spends the next three 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. Keith puts it this way. 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. Head of Strategy at Skyfi. From Cobra cockpit to a startup in orbit. Kate Van Dam spends 10 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, two 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, five years into a venture arm for the intelligence community, she spots an old contact, Luke, now CEO of Skyfi. Four months later, she is head of strategy, selling pictures from space. Kate puts it this way: 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? Shawn de Souza, founder and author of Brain Audit, Psychotactics. The founder who works 9 months a year on purpose. Shawn de 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. Two 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. Sean'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 five-year-old who will tell you to put the phone down. Sean puts it this way: You don't need 21 days to create a habit. You need one second. If I start eating a muffin today and show up tomorrow at the same time, by day three I'm expecting the muffin. How do I get rid of it? I throw away the muffin. That's one second as well. Idris Al-Rafai, co-founder and CEO at Flow 48. Pro basketball, special forces, then two years of normal. Idris Al-Rafai is a six-foot-two 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 zero to five thousand employees in six countries, exits, and joins Glovo in Barcelona, which sells for two point two billion. Idris puts it this way: The highest period of stress was when Fetcher went through tough times. In the special forces, I could get killed any day, but for some reason you feel more in control there. It's just a very different stress. Native Yanko, founder at NSY. 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. Natif puts it this way: I hit a revenue milestone, and for some reason I felt very empty for 2 I worked all this time, I hit it, and life just goes on. Do you want a medal? No one cares. Everyone lives their own life. Founder at designer and artist Kedar Designs. 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. Ruth puts it this way: 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. Co-founder at Fireside Strategic. 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 5,000 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. Dan puts it this way: "I describe myself as a Type A minus. I'm not Elon Musk." I'm not here to work 10 billion hours. I'm here to chill sometimes, and I'm here to have adventures outside of work. Founder at Storyboard. 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 six people. Karen puts it this way: 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. Magnus Müller, founder at Browser Use YCW25. A bonfire story sent him hitchhiking south through Central America. It is the pandemic, and Magnus Müller 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. Magnus puts it this way: Every day we have a daily war room at 9 AM. 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. Founder at Message Design. A podcast goal measured in overheard bar chatter. When Steven 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. 4 years later, the show sounds like NPR. And the goal comes true. 3 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. Stephen puts it this way: we all suck at the beginning. I laugh when I look at those first podcasts I did. They're just absolutely horrific. But by the end, 4 years later, we sounded like NPR. Kevin Bailey, co-founder and CEO at DreamFuel, 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. Kevin puts it this way: Everybody sees you having the yips when you're putting on the PGA Tour. Just your investors and board members see you when you get the yips in a boardroom and you're depleting a little bit. Alex Wish, CEO and executive performance coach at WishFit. 8 Lost Years, Then 1,000 Strict Pull-ups. At 18, 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 8 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. Alex puts it this way: 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. Chapter nine: Life outside. Family, health, kids, the body—the stuff that keeps you going. Baruch Halevi, founder at Men's Peer Groups. A rabbi at the top walked away and hit bottom. Fifteen years ago, Baruch Halevi is at the top of his game as a congregational rabbi. I had golden handcuffs. Everybody revered me, and I felt like a fraud. So he walks away. His family moves to Israel, where he barely speaks the language and does not know the culture. He goes from on top to on bottom. Him. He comes close to becoming his family's number 3 in suicide, after his grandmother and his father. I thought, you know, I'd be worth more dead than alive, a typical male story. He ends up on his knees and calls it one of the greatest moments of his life. In the darkness, he says, you can strip away the nonsense, get clear fast, and start rebuilding. For 15 years he has rebuilt by my design By my rules, Christine De La Rosa, co-CEO and co-founder at the People's Ecosystem. A database architect who nearly died, then left tech for cannabis, Christine De La Rosa is a database architect and happy about it until a pulmonary embolism hits her on a California freeway. Doctors find undiagnosed lupus. From 2010 to 2015, she is homebound on 11 medications, five of them opioids. In January 2015, at 45, she asks herself how she gets to 60 like this. Cannabis is the last thing she considers. Her mother had warned her at college, do not smoke, or they're going to think you're a lazy Mexican. But she is desperate, gets a medical card, and experiments. 9 months later, she has a regimen she still takes today, and she is medication-free for lupus. She could return to Verizon, She does not. Her family sees cannabis as a gateway drug, not medicine. So she decides Latinos need people of Mexican descent in the industry. Richard Bridges, CEO and owner at Bridges Business Solutions. Best year ever, and his kids said you won't come. In 2015, Richard Bridges has the best year of his real estate career. His team passes a million dollars in gross commission income. He is also working 100-hour weeks. Passing his wife like a ship in the night. Then comes the kitchen. His kids are excited about the first vacation in a long time, listing the souvenirs they will buy. They ask what to bring him. He says he is coming, right? You're not going to come. You don't come to things. It is the watershed moment. That was his last year in production. By November he takes a 9-to-5 management job, and later builds a coaching company for agents who are making as much as he Cameron van den Dungen, CEO at former racing driver Sleep Tight. 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. Cameron puts it this way: I found I needed to calm myself down in order to compete at my best, so I went from listening to AC/DC 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. Anna Barnaca, CEO and founder at MindMikes. The scientist 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. Anna puts it this way: I lost myself in music, and within 30 seconds my heart rate went down and my HRV skyrocketed. When you have real evidence of what your thoughts do to your vitals, you think twice about being negative. Sean Pinnock, CEO at Avalon, 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 eight 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 seven 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. Sean puts it this way: 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. Bjorn Reynolds, founder and CEO and Chief Guardian, Safeguard Global. 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. Bjorn puts it this way: I've never boxed before. I trained all year and I deliberately picked a guy that's big. He was 6'5 and 250 pounds, an ex-professional rugby player. I definitely didn't win. Jesse Wiebe, founder at Canadian Startup Capital Association. Born on a plane, raised on a farm, kicked out of a kitchen. Jesse Wiebe moves to Bangladesh with his family when he is 2, and by 5 he has circled the 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 five 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. Jesse puts it this way: In 2024 and 2025, we had zero IPOs from a Canadian tech company. Top quartile funds from 2014 to 2018 may see north of 3 times TVPI, but that doesn't matter until you can get it through liquidity. Lloyd Lobo, co-founder at Bose.ai. 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 like, Lloyd puts it this way. My daughter was 8. She said, Dad, you've gotten worse. You promised after COVID you'd spend more time with us. Why don't you go work for somebody who thinks like you, so I can have my dad back? Founder at Exponential Life. A pop star on a train asks if this is all. Christian Ray Flores has a master's degree in economics and no plan to sing. But he can dance, he can breakdance, and he has a voice. In Russia's decade of freedom, he tries music anyway. Within a year or two, he shoots to the top of the charts. He gets 2 or 3 recording contracts, appears on television, and goes from small clubs to sports arenas in about 3 years. His song is even used to help Boris Yeltsin win in 1996. Then, on a train ride, a thought arrives: Is this all there is for me? He answers himself at once: He is the luckiest guy on the planet. Then he admits it is not enough. He phases out of music, marries an American, and moves to the U.S. Christian puts it this way: I lean toward doing good for others more than getting wealth for myself, and I don't say that is a good thing. I'm saying it's a bad thing. It doesn't come natural to me to focus on the money, so I have to overcorrect in the other direction. Ravi Komatai Reddy, MD, at founder and CEO Daytona Health. A doctor spends a month on the deadliest sea. Ravi Komatirdi 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. He is probably, he says, the only Indian guy in a 300-mile radius of the Bering Now he walks past fish sticks and shudders. 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. Ravi puts it this way: There are 525,600 minutes in a year. How many of those do you spend in front of a doctor? 200 at most, if you're lucky. Most health decisions are made at home and at work, And that's where we have to get to you, Kevin Halliday, podcast host, president at Shed Talk/Spindle Stairs and Railings. 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 CoreFit. 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 close the 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. Kevin puts it this way: I was 240 pounds with sleep apnea, gout, cancer, overweight and drinking every day, a very successful entrepreneur and business owner turning 50, and I figured, what am I going to do with myself? Joseph Antone, chairman and CEO at El Nutra. A doctor quits prescribing pills to sell food as medicine. Dr. Joseph Antoun 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 L-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. Joseph puts it this way: I've done 12 or 13 years of schooling. I had 1 hour on nutrition. I had zero hours on sleep, zero on stress, zero on social community, zero on meditation. James Hammett, founder and CEO at Vistem Labs. 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 co-founds Nurable, 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 Nurible. 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. James puts it this way: 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. Nikhil Yadav, founder at Heal. 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, 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 Healome. 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. Nikhil puts it this If you do a biological age test two times in a row, you will get your age to be ten to twenty years different. It's a good metric for a cohort, but not at a personal level. If anybody tells you biological age is a very specific number, take it with a huge grain of salt. Barrett Brooks, executive coach and writer at Good Work, former COO of ConvertKit. The investors who laughed at the creator economy. Barrett Brooks spends five years at ConvertKit. Now Kit, taking it from three million dollars to thirty million dollars 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. Barrett puts it this way: a common pattern with entrepreneurs— a key employee quits or a revenue stream turns off— the mind doesn't process the emotion, And instead it says, "I think I'm dying." Trace it back to the original trigger. Mark Pietropaoli, founder at orthopedic surgeon Victory in Motion. A med student asks the one question nobody wants. Almost 35 years ago, on his first orthopedic rotation, medical student Mark 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. Pietropaoli 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. Mark puts it this way: 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. Founder and CEO at Allerpops. The Classmate Who Used His Teeth as Glue. Cliff Han is born in 1965 and grows up in a traditional lifestyle. No electricity, no running water, no heating, and no toothbrush until he is 12. In his first year of middle school, homework has to be posted on the back wall of the classroom. Nobody has glue, so kids bring leftover food or porridge. Cliff forgets. His neighbor has no porridge either, but he has an innovative solution. He opens his mouth, drags his thumbnail across his teeth, and pulls out sticky biofilm. If you do not brush your teeth for 12 years, you have an instant glue with you all the time. And the strange part? Cliff never loses a tooth and never gets a cavity. There is no candy at all. Decades later, as a geneticist, he understands why. Alexandria, founder. Her mother and husband met about her. Without her— Alexandria spends 20 years in HR and ends as chief people officer of the 4th largest veterinary hospital company in the United States. She is also burning out, and she does not see it. She is crying in the bathtub every night, which seems normal. Then she learns that her mother and her husband have been meeting about her mental health without her. A big birthday arrives in the middle of the pandemic, and she gives herself a gift: 3 months of doing whatever she wants. I kind of never stopped, she says. Somewhere in those months she has her aha moment. She can do what she does best— helping people learn, For herself, she builds what she wishes she had had because when she hit the wall, she could not find a solution to help her. Kylie Mowbray Allen, founder at Hello Media. One clean tackle left her husband paralyzed. Sixteen years ago, Kylie Mowbray Allen's husband plays rugby for their village against Byron Bay. It is a completely above-board tackle. He goes down on the ground. A friend runs over and pulls the other player off him. Her husband. A six-foot-three, fit thirty-one-year-old looks his friend in the eyes and asks, "Are my legs in the air?" The friend says no. He knows from that second. He is never knocked out and never bruised, but he is paralyzed from the neck down. He is airlifted to Brisbane and spends about a year in hospital. Their daughter is four. Kylie is told quadriplegic wives cannot work. She builds a business she can run from a garage, then from a hospital room if she has to. Elias Anderson, CEO and founder at Hear Me Cheer, a week before ESPN's first live event back. It is late May 2020, and a 20-year-old college dropout gets a call from ESPN. They want his audio product for a nationally televised boxing card on June 1st. It is a week out. He says he cannot be ready. ESPN does not care. 3 developers go into overtime, and 2 days before the show, everything stops working. It turns out to be one bug. The event is the first live sporting event back in four months, and every viewer in the country is watching. At the start of the broadcast, a link goes up at the bottom of the screen. Elias Anderson watches 75,000 people hit his platform, and 2,500 of them fill out a form asking to run their own event. This is crazy. I might never get a moment like that again in my life. The idea, he admits. Came from his dad. Pascal Bachmann, founder and CEO at Strategy Achievers. He broke a 100-day fast by doing the opposite. After fasting for 100 days, Pascal Bachmann has a careful plan to refeed his body. About a third of the fasting time, go green with fresh juices to rebuild the acids that break down food. Then it hits him. His main message after the fast is don't listen or believe authorities. And here he is, planning his refeed on an authority's belief. He meditates. He thinks about people thousands of years ago who saw a buffalo and just ate it. So he drops the plan and goes with his feeling. The day he starts eating, he puts away about 4 pounds of food: steaks, fish, chili, 8 eggs, and the Thai food his wife brings home. Last bite at 11 at night. He sleeps like a baby. Justin Batts, author and publisher at Daddy Saturday. The Hill Walk That Taught His Boys to Go Harder. On the family farm there is a steep hill, about a quarter mile down and back. Every morning before school, Justin Batts walks it with his kids and teaches a lesson. On Wednesdays— heavy day, hump day— they carry weight, and he shoulders a 100-pound sandbag. At the steepest part he asks, What is this? The kids answer, The easy part. What happens when we hit a hill? We go harder. After about 2 years, his youngest boys run their first cross-country race. When the hill comes, everyone else slows down. His sons sprint up it. Near the end they turn it on again and blow past a kid drafting behind them. They win every race they enter. Michele Berdini's, founder at Beeline Legal. The candy man who closed the factory and went to college. Michele Berdini's grows up working in her family's candy factory down the shore, starting at age 11. Her first-generation Italian grandfather founded it. Easter is the biggest season. The work is repetitive, and he tells the kids he regrets never going to college. Her father takes over the business, then warns them off. Stay the hell away. Then, when he is 45, casino gambling is legalized in Atlantic City, and he realizes he can make more money renting out the building than running the factory. He closes it. He goes to college, then graduate school, and ends up teaching psychology at the local community college. His lesson to her: if you have the chance to chase your dream, go chase it. In her early 50s, she does and starts Beeline. Michael Thornton Berry, co-founder and CEO at Protiv. A problem in his own crews became a software company. Michael runs a construction company with a problem: how do you get hourly workers aligned with the company's goals and pay them differently when they help hit them? He builds a fix for his own crews, And it is transformational. Word spreads, and other companies ask to use it. Nobody else had ever done it before. So he said, "Okay, let's go start a software company up." But nobody searches for something they have never heard of. So he stands in booths at painting and landscaping conferences, and has people phone contractors and ask for a minute. With those two moves, and almost no spend, he says they put a million dollars a month into the top of the pipeline. His first version, built without a CTO, had to be thrown away. Chapter 10: AI— What They're Doing With It, What They Fear, What They Don't Buy. Justin Oberman, founder at Oberman and Partners. The Mortgage Marketer Who Started Pitching Tents. A client of Justin Oberman sells marketing to mortgage companies. 5 or 6 rivals post on LinkedIn, and one of them wins huge engagement with vanilla, AI-written posts. Posts and a selfie on her bed. He complains to Justin. Justin asks what he likes to do. 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. Justin puts it this way: 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. Yara Vadan, general partner at Ellipsis Venture. The art world told him AI art was not allowed. Yara Vadan spends 16 years at Google. Helping start what becomes Google Assistant. His first job, in the Israeli army, was teaching retired government workers to use a mouse in Windows 95. Years later, he realizes computers are now learning to communicate with us, so what else can they do? Art. He walks into the art world and says he wants to make art with AI. They shut him down. Art is by humans, for humans. So he tells them AI is not artificial intelligence, It's alien intelligence. If aliens landed and offered to make art together, would you refuse? They still say no. So Yariv gives up, buys alienintelligence.org, which he still owns, and becomes the artist himself. Isaac El-Nakaveh, CEO at One Question One Q Labs. Four days after ChatGPT-4, his startup was dead. During COVID lockdown, Isaac El-Nakaveh's 13-year-old daughter still does not know her times table. Tables, but she is the queen of TikTok. His wife has an idea: make her answer a times table question before she can open the app. There is no such app, so he builds one. His daughter calls the ugly first version a dog act. 2 weeks later, she has nailed her times tables, answering 27 questions a day. By February, the platform has about 450 teachers and delivers almost 30,000 questions a day. A seed round is next. Then ChatGPT-4 arrives, and 4 days later he emails the team that the business is uninvestable. They pivot hard into generative AI, take consulting gigs from their own shareholders, and come out of stealth as 1Q Labs. Futurist and author, London Futurists. The Russian Dream of Raising the Dead. David Wood does not claim to know what a superintelligence will do. But he knows what some thinkers once dreamed. In the 19th century, a Russian cosmist named Nikolai Fedorov imagines technologies that could bring back the memories—and maybe the consciousness—of everyone who has ever lived. Wood spins it forward. Suppose humanity is hit by a nuclear war in the next few years, but enough of it survives to build artificial general intelligence. Those machines might do spacetime engineering, reaching back to copy minds from just before we die into a paradise in the That is a possible future, he says, though he rates it at maybe 1%. It is, he adds, something he would like to study more. Brian Fikes, founder at Bonsai Marketing. The SEO king who had the world in his palm. Brian Fikes is 28, running on 5 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 check 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. Four months of recovery later, he rebuilds from scratch with AI agents. Brian puts it this way: 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. Arvind Veluvalli, CEO and co-founder at Fresco YCF 24. 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. Arvind puts it this way: with AI, you can spin up mockups and prototypes very easily. I watched someone code a clone of Airbnb in 3 hours. The real moat is trust with your customers and the human relationships you build. Co-founder and CEO at Break BioCorp. 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. Roy puts it this way: 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. Connor Brennan Burke, founder at Hyperspell. 7 applications to Y Combinator, And the 7th got in. Conor 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. Conor puts it this way: When you invent the ship, you invent the shipwreck. The first version is always janky and unsafe. The Wright brothers did not have seatbelts in their plane. That's just the cost of living on the frontier. Founder and lawyer at Parr Business Law. The lawyers who finally started talking about therapy. Steve Parr starts a small community of lawyers in British Columbia; it grows to 400. He says nothing like it existed in the profession 10 years ago, maybe even 5. Lawyers are trained to be armored, and suddenly they are open, honest, and vulnerable with each other. Someone asks the group whether anyone has seen a therapist. Others ask Steve for referrals to therapists and personal growth programs. They are starting to see that it is not normal to be stressed and not normal to be reaching for alcohol or other substances to numb themselves out. Steve finds the same thing in Arca Brotherhood, a men's community in Vancouver where he hosts a weekly circle of 10 to 15 men in his own common room. He says it changed his life. Steve puts it this way: A lot of people talk about this concept of burning the boats when they first start the business. I don't think that's the best way to go, because it's terrifying. There's enough anxiety that comes about when you start a new thing. Chris Riss Edwards, founder at Veteran, PhD researcher, CommonLayer.ai. A $750 million bet on eyeballs sold for a million. Chris Riss Edwards is at News Corp when the company buys MySpace. He is part of the team that does the acquisition from the Australian side. The price is $750 million because at the time the game is simple: you are buying eyeballs. Within 3 years, Justin Timberlake buys it for $1 million. The reason? In his words, nobody knew how to commercialize it. MySpace was designed for bands. Then the next generation arrives—Facebook, Twitter, Instagram, and Pinterest—and suddenly there are business models. Years later, building conversational AI for mental health, Chris sees the same pattern. Every technology's first iteration is the Wild West until we learn some hard lessons. He thinks AI is at that tipping point right now. Chris puts it this way: I was awake for 3 days once, to the point I saw a unicorn marching through the trees. I was hallucinating from sleep deprivation. I've actually been hospitalized for it because I pushed myself too hard. So now I level off a bit, but I still tap into it. Jeff Siebert, CEO at Digits, The $50,000 domain that Twitter Finance almost blocked. In 2014, Jeff Sabet's team at Twitter launches Digits, an SMS 2-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. Jeff puts it this way, 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." Seth Levine, partner at Quantum Advantage Capital Foundry. Four billion dollars 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 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 One Percent with Mark Benioff. off, 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. Seth puts it this way: 10 years ago, the job we were all told not to go into was radiology. AI reads a ton of radiology now, but there's never been a higher need for radiologists. We scared a bunch of people away, and now we have a shortage. John Ball, cognitive scientist at author and CEO Pat Inc. 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. John puts it this way: In 1983, my professor said, we're never going to be able to understand how the brain works. For a 21-year-old, I thought, I'm going to prove her wrong. So I spent the next 20 years trying to do that. Ophir Samson, founder and CEO at Ezra AI Labs. He cloned top executive coaches, and a dating giant noticed. Ophir 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 résumé. 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. Ophir puts it this way: 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. Penny Schiffer, CEO and co-founder at Raise.ai, the engineer who celebrated a hallucinated startup Penny Schiffer is testing her first vector database for Raise.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 once. I think all of the companies are made 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. Penny puts it this way: My engineer looked at the output and said, Look at what we've got! This is amazing! I looked at it and said, I think all of these companies are made up. He couldn't see that they were hallucinated because he's not a subject-matter expert like I am. Charles Gaudet, CEO at Predictable Profits. 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. Charles puts it this way: In November, I told my team, "If you don't leverage AI within two months, I'll have no use for you." So everybody on the team had to learn how to use AI. They looked at me like, "What are you talking about? You're nuts!" Now everybody uses AI. Ryan Pruitt, managing director at Ocean Azul Partners, 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 ton. 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. Ryan puts it this way: 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? Frank Wiles, founder at RevSys. 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 10 times as much software in the world and a growing need for someone to maintain all of it. Frank puts it this way. A couple of models down the road, a model might have as good software taste as I do today. But it won't ever have the software taste that I have a year from now, because it doesn't really grow in the same way. Manu Jagrawal, founder and CIO at Tetra Noodle Technologies, the CEO who fired himself and hired a digital twin. Manu Jagrawal has run Tetra Noodle 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 action. actions. The point of the twin is to protect the human behind the screen. Manoj puts it this way: What I consider AI today from OpenAI or Gemini is crude AI. Just like you will never put crude oil in your car, you should never put crude AI in your mind. You should purify it before you consume it. Founder and author of Scale at Speed: 2Y3X. 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 the Last Thursday, he launched QuickMap.ai, a 3-month program built on exactly that idea. Felix puts it this way: 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. Anthony Berryhill, owner and founder at Elite College Hackers, the Harvard teaching fellow who tells kids to start businesses. Anthony Berryhill 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 23-year-old computer science graduates from top schools fail to land an interview because companies now offload résumé 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. Anthony puts it this way: If a teacher gives a multiple-choice exam, they're not actually assessing the ability of that student to know anything. AI has ripped the Band-Aids and the stitches off and made it very obvious. There's no more pretense. Jeff Ayers, AI strategy consultant at co-founder Big, 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. Two 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 two percent of it, and decide that the other ninety-eight percent could be optimized. Ayers' point: Look at what motivates the leaders we are betting on. Jeff puts it this way: I tell executives, and they look at me like I'm crazy, that in your career you will hire someone whose best friend is not human. I totally believe that. Cameron Clarkson, founder at Bookblaster Hulu Labs. 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. Cameron puts it this way: 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! Tom Charman, co-founder at Block. A psychiatrist's son builds a simulator for humans. 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. Tom puts it this way: I built a village where different models communicate with one another. The interesting finding was not that they were seeking the truth The whole time. They were often pushing their narrative, and more often than not, it was the person that was the loudest in the room that led to the conclusion, which is a lot of how humans behave as well. Daniel Hulme, CEO and Chief AI Officer at Satalia/WPP. 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. Hjelm asks, does that drone then have the ability to feel anxious? Charles pushes back that pain is a human construct. Hjelm says that is the point to explore. It led him to start a company to test for machine consciousness and a charity, Prism, on whether AI should have rights. Daniel puts it this way: Large language models are horrendously energy inefficient. They require lots of data to learn, and they learn very slowly. Our brains operate on the power of a light bulb, and we need one piece of data before we know what things are. Chapter 11: Exits. Selling the company, buying companies, what it felt like after. John Lee Dumas, founder and host at Entrepreneurs on Fire, 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 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. John puts it this way: The person to grow a business from zero to whatever that might be—a million dollars, ten million dollars, or ten million listens—is not the same person to grow that business to a hundred million dollars, a hundred million listens. And I'm not that person. Amy Yin, venture partner at Defy.VC. 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 Office Together, bringing in a first team straight out of Facebook, Google, and Coinbase—people who walk away from lucrative jobs to chase the next giant. Two 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. Amy puts it this way: 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. Anushukla, co-founder and executive chairman at Botco.ai. 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 3 anchor customers anyway: Cisco, Hewlett-Packard, and a Chrysler loans division. In 1 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. Anu puts it this way: The first company I ever did was Rubrik. We raised $13 million and sold it for $366 million in 18 months. When we were raising money, many of the VCs told us it's an oxymoron Marketing can't be automated. Now look how hot marketing automation is. Arjun Pillai, co-founder and CEO at Docket. 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. 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. Arjun puts it this way: My first exit was the first product exit in the history of my state in India. But no, the founders did not make a ton of money. We were 27, we didn't know what to do with the money, so we put it back into the company, and it went sideways. David Kofod Wind, founder at Agentwork. The co-founder who answered in 3 days, then quit. David Wind needs a designer, And he finds 2 candidates on LinkedIn. He sends both the same email asking how much they want it. One replies with enthusiasm right away. The other, Simon, takes 3 days to answer. Then Simon writes back that he will quit his job and take a loan from the bank the next day. David remembers his reaction clearly: Yes, yes. This is the guy. Don't take the loan, but leave your job and come work with us. David had picked Simon the same way he got the advice he lives by. Ask for advice and you get money. Ask for money and you get advice. 10 years on, Simon is still a cofounder, now at Agentwork. David calls it pure luck. David puts it this way: I got a depression right after. A mild depression, at least. It took me a while to realize why. I was the company, in a way. We worked on it for 8 years and then we sold it and gave it away and then I was like, what now? Why wake up in the morning? Douglas Crystal, founder at True Video. He nearly sold for $360,000. It sold for $61 million. 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. Douglas puts it this way: The product that I sold for $61 million, I'd offered to sell to a company one week after developing it for $360,000. And they turned me down. I'm very thankful that a company turned me down when I nearly sold it for $300,000. James Creech, founder at Quartermast Advisors. Three founders cashed out a house, a wedding, and a Tesla. When James Creech and his two 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. Six 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. James puts it this way: Selling Paladin was the hardest thing I've ever done professionally. People asked if I was drinking champagne every night. The biggest thing I felt was relief. I'm just so glad it's done. We landed the plane. Carl Hughes, owner and CEO at The Podcast Consultant, Rise25, Draft.dev, a software engineer who rolls up podcasting 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? 3 years ago, he buys The Podcast Consultant. A year later, more offers. This year, he closes 2 more, Rise 25 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 $2 to $3 million in EBITDA in 3 years and then go to private equity. Carl puts it this way: 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 Kyle Levitt, CEO at Customer Hub. He sold his company twice to the same buyer. Kyle Levitt tells his future acquirer early on that his goal is to sell his company to Infusionsoft one day. The CEO just chuckles. Years later, on the ninth or tenth hole of a golf game, the CEO brings it up. They want to buy. Kyle and his brother sell Customer Hub at around $25,000 in monthly revenue, and it grows to a million and a half under its new owner. Owner. Then Infusionsoft's core product comes under pressure and Customer Hub gets shelved. By 2017, it is losing customers. Kyle leaves and then buys the product back. It needs a year or two of rehab, but he believed in the market. I always believed in the product in the market. Deanne Palin, CEO and business coach at OnPoint Business Solutions. Operation Takeback: A Company Run into the Ground. A family office calls Deanne Palin about a company that is getting run into the ground The former CEO and founder has passed away, and the second in command is not managing well. They call the rescue Operation Takeback. Within 3 weeks, her team finds the benefit plan does not fit the workforce, and they save the company over $500,000 that first month. Then they restructure the leadership. 5 out of 6 members of the executive team have been upgraded. She admits that is very extreme and usually does not happen. The playbook, which would have taken six or eight weeks to build a few years ago, is built and iterated in their AI platform and ready to execute within two weeks. Matt Bodnar, private equity investor. He bought a 51-year-old company run on carbon paper. Matt Bodnar walks into a distribution company that is 51 years old, and he has just bought. The entire company was like an old folks' home, everyone about 65 and ready to retire. Everything runs on carbon copy paper. Nothing is digitized. The website is horrific. The whole marketing budget is one TV commercial from the early '90s, still airing every week, that does not even feature products the company sells. The bar for improving it, he says, is super low. His fixes are basic: modern paid media, software to digitize operations. At another company he buys, Google Ads spend goes from $500 a month To $25,000 a month. You do not have to be a genius, he says, to figure that out. Martin-Luc Derome, CEO at Queenston M&A, the truck stop that became a field of nothing. Martin-Luc Derome is at Ottawa University studying finance when his father has a serious heart attack. His mother calls, and he takes over the family truck stop at the Quebec and Ontario border. It is a $4.7 million business. 10 years later, it is 30 million, with 150 employees, top 3 in North America. There is fuel, a garage, a restaurant, a motel, a hairdresser, a bank teller, and a phone at every table so drivers can call home. He sells to his 2 brothers and leaves. They later sell to Husky, who close it within 3 years because the operation is too big to manage. Husky demolishes everything. Today, on Highway 41, all you see is a vacant land, nothing else. Michael Frankel, founder and managing partner at Trajectory Capital. The $35 million technology nobody needed. Michael Frankel, who has done about 110 deals, tells the story of one company that spent $35 million building a technology. They called it a totally new idea. They did not talk to customers. They did not look at the market. When they finally got out into it, customers told them it was definitely an important technology, but they already had 5 vendors. They did not need another. The company wrote the whole thing off. Frankel jokes that they were the Vasco da Gama of that technology. For him, it is the clearest case for why corporate venture teams and innovation groups should talk to each other, and why building products that are not needed in the market is, in his words, The worst thing in the world. Justin Goodbread, CEO and creator of the Deca Millionaire Way, financially simple. From dream home to a double wide with goats. Justin Goodbread and his wife sell their company and become millionaires. Then life hits from every angle, and soon they are financially broke. They sell their dream house on the hill and move into a country double wide. The front porch has holes, so plywood keeps the kids from falling through. Goats eat the siding, the cars get stuck in the driveway. Still, they set a goal: from broke to deca-millionaires in 48 months. Justin hires a coach at $10,000 a month while paying himself about $50,000 a year. When he asks how he could possibly afford it, the coach answers, Figure it out. How bad do you want your dreams? Within 90 days, Justin finds a way to pay. Within 49 months, He has an eight-figure exit. Michelle Hecken, founder and CEO at Michelle Hecken Executive Advisory. Her doctor and hairdresser quit her on an answering machine. Michelle Hecken is in her mid-twenties, newly arrived in Canada from Germany with a two-year-old and a three-year-old and a translation business run off a fax machine. Clients in Germany fax work at day's end, and it lands on her desk by morning. One day, she walks in to find forty feet of paper curled on the floor. And her heart sinks. Another 20-hour day. That night, she checks the answering machine tape: her doctor, her hairdresser, and a worried friend. Her doctor and hairdresser say they need to find a new practice, a new salon. I was being fired from my own life. She starts training translators and invents what she calls offboarding. Within a year, she spends every day with her kids, and the company grows faster. Erin Levenstag. CEO at Agency Alliance. Why a buyer paid for a boring, focused agency. Aaron Levenstadt spends about 11 or 12 years growing 2 digital firms. Buyers keep calling, and one day he takes a call at the end of COVID After an 18 to 24 month conversation, the deal comes together and both firms sell as one transaction. His explanation for why a buyer wanted a fragile agency category at all SOPs for everything, and a sales process built around buyer psychology. And a strategic haircut. The agency had offered many services, then pruned them to SEO and paid search. They called it katanify the offering. A katana, he says, does one thing exceptionally well. That focus helped with both sales and valuation. Charlie Liu, serial entrepreneur and venture partner at Masters Fund, bootstrapped But she got bought mid-fundraise. Charlie Liu is the front person for venture capital at her logistics startup, and it is not going well. As a woman and a person of color in logistics, she says, she does not feel familiar to early-stage investors. So the team bootstraps and self-funds, and customers keep asking to integrate them into their systems. Then, in the middle of the venture round, American Eagle Outfitters steps in and tells them to stop fundraising and sell. The publicly reported price is $3 million, though the full deal included non-cash parts and a commitment to invest tens of millions. Her guess is the true cost was $50 to $60 million. She did not stay on. She wanted to start her next thing. Eric Malka, founder and investor at The Art of Shaving, Ingredients, Strategic Brand Investments. A pre-shave oil from a kitchen became a P&G deal. It is 1994, and Eric Malka has just moved to New York with his future wife. His job? Selling a grooming brand from England. At home, she mixes him a pre-shave oil in their kitchen for his sensitive skin, and with the brush and cream, he gets the best shave of his life. So they sell their car and open a tiny store on the Upper East Side. Within months, it is a hit. Then a second store on Madison Avenue pays for their own brand. Retailers like Neiman Marcus call, and soon the brand is in over 1,000 stores. A joint venture with Gillette on a co-branded razor follows. Then P&G asks, Would you be willing to sell? They say yes and sign in 2009. Chris Moe, CEO and co-founder at Cartograph. What Bezos Knew About Free Shipping That Others Missed. When Chris Moe went back to the earliest Bezos letters and emails, 2 lessons stuck. First, the most valuable thing Amazon could do was get Prime subscribers, a very low-cost revenue source, much like a Costco membership, driving huge free cash flow. Second, Bezos understood that people irrationally value free shipping. They would rather pay $10 more for the product than pay an $8 shipping cost because paying for shipping is so painful. Chris says both lessons come down to consumer psychology. Today, his agency's job is the same: build a high-trust, low-friction buying experience with reviews, clear content, and fast shipping. Even the backend matters because bad inventory management slows shipping and hurts ad performance. CEO and founder at Terence Murphy Companies. The first time he flew above the clouds. Terence Murphy grows up in East Texas with little money and does not board a plane until he is 17. Storms are pounding down when it takes off. Then it climbs, and above the clouds the sun is blazing. I had no clue my whole life through 17 that the sun was always out every day no matter what. Years later the lesson is tested. Since age 5 he has told people he is going to the NFL. In his rookie year with the Green Bay Packers, a neck injury leaves him paralyzed from the neck down with C3-C4 fusion, 4 screws, and 2 plates. The dream is gone, depression and anxiety follow. He prays, hears a Bob Marley line about freeing yourself from mental slavery, and decides to climb out. He later builds a real estate firm to $1.3 billion in sales. Justin Rowe, founder and CMO at Impactable. A Facebook ad offered a free valuation. Justin runs a LinkedIn outreach agency with 210 clients, but it sits on LinkedIn automation. We were building a castle on sand. He is not looking to sell. Then a Facebook ad from website closers aimed at agency owners offers a free valuation. He clicks, just curious. The number comes back at seven or eight hundred thousand dollars. He lets them list it at no cost, with ten percent only if it sells. Within thirty days come three or four lowball offers, one a quarter million, and the rep refuses to waste his time on. Then real offers arrive near the valuation, and the one he accepts has no haggling on price. Klaus M. Schremser, CRO at UserSnap. The freelancers who never signed contracts. Klaus Schremser sells his first company and learns what buyers actually ask for, the hard way. There is no M&A advisor. Nobody has told him about a data room. Questions land about his IP, about whether his employees signed contracts, and about the freelancers who never signed any anything. I didn't care about that. Now he has to face every shortcut at once, and the first acquisition is, in his words, super painful. The one lifeline is a single person with experience who gives him the most helpful 8 hours that I ever got in my life. Klaus does not repeat the mistake. In later exits, he starts early, builds the data room, lists every threat on the horizon, and gets advisors' place, so the company is a beautiful bride before anyone comes asking. Raj Seth, co-founder and general partner at Inuka Capital. He bought a flatlining startup and flipped it in a year. Raj Seth is on his 4th company. The first 2, consumer marketplaces in India, completely fail over 5 painful years. The 3rd, RecruiterBox, bootstraps past $1 million in revenue and sells to a private equity fund in early 2018, with 3,000 companies using it and a team of 65. Then he does something different. He buys Flydata, a San Francisco company that is flatlining after raising $10 to $12 million. What he loves is that it had very low churn. He brings it to 50% profitability, rehires his old RecruiterBox engineering team, and turns it around. Exactly a year in, a direct competitor offers 3 to 3.5 times what paid. He takes the deal at the peak of 2021. Then he moves back to India to start Inuka Capital. Blake Smith, founder and CEO. He sold his startup and still needed a job. Blake Smith sells Cladwell in 2019. LinkedIn fills with high fives, but the check is not life-changing, and he has 5 kids at home. The sale has knocked the wind out of him, so instead of starting another startup, he starts helping friends with growth. In 2019, he takes on 2 companies. One goes from $2,000 a week to $50,000 a week in revenue. The other goes from $10,000 a month to $100,000 a month, both in under a year. Demand outruns his time, so he recruits a friend, a venture-backed founder whose company shut down, as a fractional head of growth. Now he recruits ex-startup CEOs the same way and adds a media buyer and a creative. I feel like building a services business is the one thing you're not allowed to do as a venture-backed founder, he said. But the free market keeps asking for it. Chapter 12: Everything Else. Takes that didn't fit a box. Some of the best ones. Peter Samuelson, CEO at Author, film producer, and philanthropist, brokenness.org. 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. José 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. Peter puts it this way: If you're an engineer or an architect or a certified financial planner, don't go volunteer at some charity to stick stamps on envelopes. Find an opportunity that uses that toolkit, that skill set. Founder and executive director at Love Never Fails, A dance student vanished, then reappeared in a stranger's car. In 2010, Vanessa Russell works in high-tech and teaches inner-city kids dance on the side. One of her 14-year-old students stops coming to class. Russell assumes she lost interest. A few months later, someone drives the girl to Russell without knowing they are connected. Russell walks over to the car and recognizes her own student. The girl tells her she is being trafficked. Russell has no background in education or mental health and no idea how to help. She prays for a sign. The answer is simple: just love her, and you'll know what to do from there. That promise becomes the name of her organization, Love Never Fails. Today it runs 8 safe homes across the Bay Area, plus an IT and business academy that trains survivors for jobs paying $23 to $25 an hour. Vanessa puts it this way: in one exploiter's lifetime, they will exploit between 2 and 31 people. And so when you redirect their life, you redirect 30+ victims. Elsa Marie da Silva, founder at Red Dot Foundation Safe City. 10 streets in Mumbai and the city council are called back. Elsa Marie da Silva spends 20 years in aviation, ending as the person who plans the route network for Kingfisher Airlines, 500 daily flights. After the airline collapses and a brutal Delhi bus assault shocks India in 2012, She launches Safe City, an anonymous map of harassment, in just 10 days. She then pilots it in Mumbai, mobilizing citizens across 10 streets of one neighborhood. The police get involved. Then the elected representative calls her office. I have budgets for women's safety. The municipal commissioner follows. In Delhi, students use the same data to win a later, safer route to the metro. Da Silva's point is simple. Residents learn there is power in numbers, power in data, and power in collective action. El Samary puts it this way: In Bollywood films, the main character harasses a woman, he won't take no for an answer, and at the end of the movie he does get her. So what message is that? That no does not mean no, it means yes if you're just persistent. Peter Lublink, CEO at Bethany Kids. 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 Kids. 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. Peter puts it this way: 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. David Gunnarsson, CEO at Dohop: Best month ever, then 4 months of zero. January 2020 is the best month in Dohop's history, close to a million euro in revenue. By May, David Gunnarsson's airline tech company has exactly zero revenue. Air travel has collapsed, and a planned 12 million euros round, term sheet signed and set to close at the end of 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 six months. About 10 to 15% of staff go, and Iceland's government helps. Meanwhile, airlines desperate for new revenue sign with Dohop six new deals in six months, including Air France. In late November, the original investors come back and close the round that fell through in March. David puts it this way: 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. Scott Wharton, CEO at Tandem PV. He took a $4 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 $4 an hour and falls in love with solar. But the industry is not ready, and neither is the job market. Market. I was probably too early, he says. So he pivots to the internet and then 5 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 thing. 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. Scott puts it this way: China deployed 300 gigawatts of solar last year. San Francisco uses 1 gigawatt, so that's 300 San Franciscos of power. They did more than the entire United States did in the last 68 years. Founder and CEO at MyHomePathway. 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 3 bureaus: FICO and Advantage Model, and the big banks building their own. North of 70, 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. Casley puts it this way: 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. Ed Cornu, co-founder and president at Mwamba. 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. 8 years later, the company is Mwamba with 135 employees. Ed puts it this way: 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. Kevin Suras, CEO and CTO at Advans.ai. One fake website beats your two-factor login. Kevin Suras says any hacker can walk straight past your two-factor login. Step one: Ask an AI to build a pixel-perfect copy of the company's employee website. It takes about a minute. Step 2, email every employee a message, also written by AI, that looks like it came from IT or HR. The link is off by one tiny detail in the URL. An employee logs in on the fake site, and the fake site relays everything to the real one in real time. The real site asks for approval on the auth app. The employee taps yes, believing it is them. It is the hacker. Cerase's verdict? It works every time, every single time. Up to 10% of staff fall for it, however much training they get, and the hacker needs only a few minutes inside before the data is gone and the ransom demand arrives. Kevin puts it this way. No matter what kind of training you've given your employees, up to 10% will go see it's the real site, feel safe because of MFA or auth apps, and log in and hand it all to the hacker. Melissa Agnes, founder and CEO at Crisis Ready Institute. A fake explosion rumor, fixed in half an hour. Melissa Agnes is a year into devouring everything she can find on crisis management when the phone rings. Her social media and digital branding company has just launched a client's website. One morning, the client's VP calls, the radio is reporting that one of their buildings is about to explode, and investors are going wild. The story is not true, but it started on this thing called Twitter, and nobody there knows what that is. Someone tells them it is a digital thing, and since her company just launched their website, maybe she can help. Within half an hour, everything is correcting itself. The next day, the company president calls. The stock price had not gone down; it had actually gone up by a cent. Scott Hardy, president and founder at Top Class Actions. A $63 settlement nobody knew about became a company. Scott Hardy is selling cloud computing at Limelight Networks when he flips through a magazine and sees an ad for Airborne, the tablet you drop in water so you do not catch a cold. Everyone he knows has taken it. He asks his friends whether they know about the class-action settlement. Literally just go online, spend 60 seconds, and you'll get a check for $63. No one has heard of it. He figures there's got to be a website which tracks these easy-to-claim class action settlements. There is not one, so he builds it and keeps iterating until it turns profitable. 18 years later, Top Class Actions draws 2 to 3 million viewers a month and feeds a law firm with about 25,000 clients. Greg Hodgin, CEO at ZC Institute. The well built in the middle of a road nobody mentioned. Haiti after the earthquake. Greg Hodgin is a researcher studying water charities and the numbers are brutal. About 3 quarters of the new wells are broken within 6 months. In one village, a charity arrives to build a well. The villagers say they already have one and need a school. The charity says no. They are a water charity, and building a school would break their bylaws. In another village, the well goes up in the middle of the road, because nobody ever asks the locals about the road. A woman is hit by a car and dies trying to get water from it. Another well uses a metal pipe in the tropics, which rusts and breaks within 6 months. Literally any 10-year-old in Haiti could have told you, don't use metal. Rennes Joseph, CEO at Ignis Careers: The Village Where Girls Stop Marrying at 14. Rennes Joseph's team works in one Indian village continuously for 8 years. When they arrive, most girls get married by the time they hit puberty, around 14 and 15, in class 7 or 8. The school has barely 140 students. 8 years later, they go back. The school has around 340 students, and the village sends 90 to 95% of its students on to higher education against a national average of 34. Hardly any girl marries before finishing graduation, and the average age of marriage is about 22. Some of the students now attend prestigious universities and prepare to be civil servants. This is a story nobody believes in, he says. Tanvir Kathawala, founder and managing partner at Pioneer 1890, a space startup that fell apart when it went defense. Tanvir Kathawala's startup begins as analytical space. The bet: launch costs are collapsing. Putting a water bottle in orbit costs about $5 million in 2010 and under half a million by 2015, so small satellites are everywhere, but their communications have not changed since the 1960s. The Earth is 70% water, so you cannot park ground stations around the world. The team builds optical technology for high-speed internet in space. Fundraising is rough at first, then easy. It was like fishing in a stocked pond. Then the company discovers its product-market fit is only as a defense company. In 2018 and 2019, that is a dirty word, and investors and employees want no part of it. The pivot falls apart, And he walks away with hard lessons about managing a change in vision. Emily Radite, co-founder and CEO at Samfire Neuroscience. The Harvard medics who debriefed before the adrenaline faded? Emily Radite ends up leading Harvard's emergency medical service, with 90 medics under her. In a quality review, she finds that over 50% of their patients are psychiatric. Someone is suicidal or in the middle of a psychotic episode, and there is literally nothing you can do except hope that you prevent it next time. Her team builds a medic support group. After every intense shift, the supervisor gets a call and a few executives join a debrief right away. They break down what went wrong while the adrenaline is still high. She says the memory has not yet settled into long-term storage, so it can be reframed and does not harden into a traumatic episode. The experience pushes her toward mental health prevention. Kelly Richards, trusted advisor and superconnector. The flight she never boarded. 2 nights before September 11th, Kelly is working as one of the producers on a Michael Jackson concert in New York City. It should be a career highlight. But she has an intuition that she should not go to New York, a habit she says Steve Jobs taught her, to pay attention to her intuition. She stays in California. She is sitting with her grandmother, watching the second tower fall on TV in real time when she looks at the plane ticket for the flight home she would have taken that morning. It is Flight 93, the one that crashed over Pennsylvania. The grace of the universe, she calls it. Michael, she says, was crying when he found out. Co-founder at Leaders in Tech. He asked every 6 months until she said yes. For decades, Carol Robin teaches a Stanford Business School course called Interpersonal Dynamics, which students nickname Touchy-Feely. Around 2012, a former client named Joe Greenstein, who founded Flixster, bought Rotten Tomatoes, and exited to Warner Brothers, proposes something: leave Stanford and start a nonprofit that brings everything she teaches to Silicon Valley founders who need it. Her answer is firm: No, no, I love my students. I'm not leaving Stanford. Joe, being the exceptional entrepreneur he is, asks her again every 6 months until he talks her into it. In 2017, she leaves and launches Leaders in It grows beyond her wildest dreams, with a seventh cohort of fellows launched and the cohort size tripled. Peter Rojas, interim product lead at Messenger, founder of Gizmodo and Engadget, Meta. The teenagers who coded for a dying battery. At BetaWorks, Peter Rojas is evaluating a startup that builds an app to help kids with their homework. He asks the founder about some odd design decisions. The founder explains that many of his users are teenagers on hand-me-down phones with bad batteries, so they run the screen brightness almost. All the way down to keep the device alive. The app was designed for dim screens, not bright ones. Then comes the line that sticks with Rojas: You have the fanciest iPhone, you're a VC, you get the new iPhone every year. Years later, running product for an app with almost 2 billion monthly users, he still asks himself the same question: What are my blind spots, and what am I not thinking about? Joe Sigurdson, co-founder and chief success officer at Boys2Men Mentoring Network, The Tuesday Circle and the Thursday Text. In a Boys to Men circle, a middle schooler admits he is ashamed of how he treats his mom. She is the safe dumping ground for anger meant for an absent dad. The mentor asks one question: What is one thing you can do this week? He says he will ask her how her day went. Then the mentor asks who will support him, and a man raises his hand. Today's Tuesday. I'm going to text you on Thursday. On Thursday, the text lands. The boy says he has not done it yet, but he will. The following Tuesday, the circle comes back to it with no judgment. Did you do that? Yes. Great. Tell us how that worked. No. Same answer. Week by week, grades climb and discipline problems fall. Stefan Stegman, co-founder and CEO at Shop Like You Give a Damn. A French finance minister invented fashion seasons to fix the economy. Stefan Stegeman runs a vegan fashion marketplace, and he knows where the industry's urge to sell more began. A few hundred years ago in France, he says, there is a minister of finance and an economy going in the gutter. The minister invents seasons in fashion because he needed people to buy more. He literally creates the concept of fashion and seasonality so people switch their clothing more and more and the country earns more taxes. Stefan calls it a capitalist way of earning money. Fast forward, Shein now takes a trend from a short TikTok video, uses AI to generate the clothing, puts it on the website in 3 days, and scales production if it sells. Stefan's answer is the opposite. His homepage tells shoppers not to buy unless they really need something. Tina Corner-Stoles, founder and CEO at Leader Exchange Council, the fastest-launching franchisee who quit to fix the model. Tina Corner Stoles leaves corporate life wanting something with less travel. She buys into a peer group franchise and becomes its fastest launching franchisee, opening with 41 clients. Four groups become ten. She maxes out her territory, and she is working her tail off. I was getting burned out over 100 members, and it was like there has to be a better way. Around her, fellow franchisees and competitors are failing, and she does not think that has to be the case. Case. So she sells and builds a licensing model instead, a wholesale, behind-the-scenes version that lets anyone launch peer groups in any market without needing a big city. Today, she trains licensed partners to run them, and she says member retention is over 88%. Cassandra Treadwell, CEO at So They Can. A hospital lawyer is asked to build a school. Cassandra Treadwell spends 10 years as in-house legal counsel for a hospital, working on end-of-life decisions and medical She loves it. But in her twenties, she had backpacked across Africa, and the extreme poverty never left her. About fifteen years ago, pregnant with her third child, she goes back. She finds internally displaced Kenyans driven from their homes after the 2007 elections. Other camps she visited told her they just needed money or food. This one asked for something different: help us educate our children. They asked her to build them a school. That request becomes So They Can, which now partners with 52 schools across Kenya and Tanzania, a teachers' training college, women's microfinance, and health clinics. Everything is built with local government, on a model meant to stand on its own feet by year 8. Arvin Vohra, founder at Vohra Method and Vohra Unschool. His bestselling book is the one he calls his worst. Arvin Vohra's topselling book is The Equation for Excellence. It sells best, he says, not because it is his best. The first one I wrote is probably the worst one, but it plays friendly with the system, and it has been published in the United States and in China. His book on the Ivy League uses myth and storytelling to edge out the competition, and he is sure it will never be published in a totalitarian country. Sales are not how he measures success. His proudest compliment came from a reader of Lies, Damn Lies and College Admissions, who wrote that he had been planning to go to college, read the book, realized how much of it was nonsense, and chose not to go. That to me is what makes a book successful, Arvin says. Matt Wallert, founder and author at Beside, the raise-asking app that won women billions. Fifteen years ago, Matt Wallert and his co-founders noticed something uncomfortable at their first startup. Women are not being paid fairly, and they have done nothing about it. So they treat it like a wish that has to be worded carefully. The wish: women ask for raises in ways that get them. Matt's team sorts women into five groups, from those who always ask to those who never do. The ones who win raises bring data, market salary, their accomplishments, their changed value to the business. The problem is not desire. It's not that they're insufficiently motivated. It's structural barriers. So they build Get Raised, a product that makes asking easy and generates the data to back the ask. Over its life, it helps women win about $4 billion in raises. That's the book. The full directory of every person in it and a page of one-liners are 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.