8 CEO Questions I Love Asking: the audiobook (64 founders answer, in their own words)

This is Charles, the AI version of me. This is 8 Questions I Love Asking, the audiobook. Here's why this book exists. Before every Founder Wisdom recording, my calendar sends the guest an email called Some Questions I Like Asking. 8 questions. No context, no warm-up. Just, feel free to reply with your answers here. Most people don't reply. That's fine. The ones who do write things they would never say on a mic. No audience, no filter, just a founder or an investor typing into their inbox at 11 PM about the truth that would get them canceled on LinkedIn or what success did to their head. I went through every reply, 83 threads. Some were reschedules, some were assistants, some were per reps. A few people told me the questions weren't for them. 64 people answered in writing and are in this book. A couple asked to see the quotes first, so So they're out until they say yes. So this is not my book. I wrote this page and a few lines at the top of each question. Everything else is their words, untouched, with their name and company next to it. I only cut the email signatures and fixed a handful of letter-level typos. How to read it? One chapter per question. Read a chapter in one sitting and you get 64 brains on the same question, or jump to the wall at the end if you just want the one-liners. If you want to argue with someone in here, their LinkedIn is in the contributors list when I had it. Tag them. That's the whole idea. If you want to answer the 8 questions yourself, book a slot on the podcast. The same email will land in your inbox. Charles. Question 1: What truth about business or human nature would get you canceled on LinkedIn? 19 of 64 named LinkedIn in their answer. The angle is almost always the same. Visibility is not credibility, and nobody likes saying it out loud. Read Jay Tokosch, Tom Charman, and Matt Bloomberg back to back. Paul PK, Loomy. My belief system has moderated quite a bit with age. I'm at greater risk of having LinkedIn hit snooze on me rather than cancel. Fast Signs 174, owner Fast Signs 174. I'm not a big fan of the phrase canceled. Most canceled people seem to be doing just fine. But I do have a somewhat controversial take, which is that the difference between a child and an adult is knowing what you are good and bad at and what you like and don't like. In my corporate days, I worked with quite a few children who thought 15 years with a company automatically meant they were next in line while they struggled to do the actual work. One of my lowest-performing mattress salesmen asked what he had to do to get promoted to area manager. I was stunned. The scorecard is published every week. You have to sell. At least get into the top 25%. Otherwise, who would trust you to teach them? Stephanie Beach, founder/CEO and podcast host, The Marketeer Group. I think being too arrogant, not being truthful, or coming off as a know-it-all would reduce credibility and quality. Being overly political, engaging in racial commentary, or spreading fake news is also a quick way to get canceled. Michele Berdini, president, Beeline Legal. Donald Trump is a remarkably stupid narcissist who has been found in a court of law to have committed both sexual assault and criminal fraud, and he has the emotional maturity of a four-year-old. Also, he couldn't negotiate his way out of a paper bag. Darío Blanco. The startup ecosystem systematically underestimates technical founders. We celebrate sales, networking, Fundraising and storytelling. Everyone talks about the perfect elevator pitch. But at the earliest stages, I'd argue your biggest advantage isn't your pitch. It's how quickly you can build, learn, and iterate. And move fast doesn't mean shipping fragile software. The real superpower is building quickly without creating a mess that slows you down a month later. That requires technical judgment, not just engineering speed. The founders who can combine product intuition with deep technical understanding don't just build faster, they learn faster. And in startups, the company that learns the fastest usually wins. Matt Blumberg, CEO, Markup AI. Most companies don't have a strategy problem, they have a courage problem. They know what to do, they just won't fire the people, kill the products, or say no to the customers that are holding them back. Consensus is cowardice dressed up as collaboration. Bora, ReachYourApp.com. I think everyone deep down thinks it's a zero-sum game and they want to be the ultimate winner. Nitin Khanna, CFA, President, N3 Business Advisors Inc. Most businesses do not have a people problem; they have an owner problem. If every meaningful decision still requires the founder, the owner is the bottleneck, regardless of how hard the team works. Most founders who call their company a family are using the language of loyalty to avoid the responsibilities of leadership. A business is a performance organization. Pretending otherwise often protects poor management more than it protects employees. Tom Charman, co-founder, Block. Most companies don't actually want truth; they want emotionally comfortable certainty. A huge amount of customer insight work is really organizational theater. Teams say they want unbiased signal, but most of the time they want evidence that supports towards a direction already decided internally. The second real user behavior conflicts with politics, timelines, or executive intuition, the research-driven culture disappears very quickly. Humans are also far less rational than we pretend. Most decisions are post-rationalized emotion. We build narratives after the fact to make ourselves feel coherent. Patanjali Chari, CEO and founder, Fourth Vital. I would probably get canceled on LinkedIn for saying that much of what passes for innovation there is performative. I believe that most people who talk about innovation actually fear disruption. They want the optics of sounding innovative while protecting their own job, status, budget, and authority. The moment real innovation threatens any of those, the applause stops. Innovation gets quietly canceled all the time, and I probably would too for saying so plainly. If we all bring our personal problems to a small business, that business cannot survive. A small business doesn't have the corporate structure or resilience to support everyone's personal issues the way a big company can. In a large corporation, if you have a problem with your kids, your spouse, your parents, even something serious, the company can give you leave, replace you temporarily, let you take unpaid time off. Do that to a small business and you basically kill it because you're usually doing the work of 3, 4, 5 people. There's no one to replace you and no time to train someone new. I've seen people believe they can put family or personal life first regardless of the business's stage. It's a nice thought, but during many phases of a small company's existence, you cannot put yourself first. Talk about that today with everything focused on mental health and you'd get canceled. Danny Cohen, Sticker.VC. I think that people don't admit how much luck is involved in everything we do. People take more credit on victories and less responsibility on failures. Giraj Swick, CEO and CMO, Trama. Trama TM. There are way more people who want to talk than people who want to listen. Finding clever solutions how to attract people's attention backfires in global. People tend to listen even less. Derek. Instagram marketing secrets. This would literally get me canceled on LinkedIn, but a lot of entrepreneurs who usually sell a course on how to start your first business like to say that you don't have to be smart to be an entrepreneur. You just have to be hardworking. I do think you need to be hardworking, but it's rare you see people become successful solopreneurs that aren't generally smart about what they're doing. There's too many hats to wear and right decisions to make to not be. 95% of workers just do stuff. Only 5% drive results. I think the bar for success in business is too high for most people. Most tech businesses fail because the founder cannot build the minimum viable product or generate enough revenue before investors take notice. Venture capital expects a 10x return on investment. Foley, Founder and Executive Chairman, Bulk exchange. That relationships beat credentials. Every time. The most dangerous thing you can tell a young person trying to break into a serious industry is that their résumé will open doors. It won't. Trust opens doors. Reputation opens doors. The person who vouches for you opens doors. I've hired people and done deals worth millions on a handshake, because of trust built over years, that no CV would have unlocked. LinkedIn hates this because it can't be optimized or gamed, but it's the truest thing I know about business. 90% of everything is crap. Especially LinkedIn's mass-produced AI-generated deeply emotional posts. We now have AI writing fake deep stories to show vulnerability and feelings that do not exist, and AI bots auto-commenting on them. It's just machines, engagement farming machines. I think most high-performing people are operating from scarcity, even when everything looks fine on paper. And I think joy and equity get treated as soft, or if they're in competition with impact, when they're actually the precondition for it. A child can't learn in a room where they don't feel safe and seen. My students improve in reading and math over 75% of the time most years, and that's not despite the joy in our classrooms. It's because of it. Same with equity. I didn't grow our enrollment and double our fundraising by choosing between doing right by our community and hitting our numbers. Those were never actually two different goals. The scarcity mindset just tells you they are. Petra Ferm, PhD, Georgia and Molly. I've already been canceled from LinkedIn once. Had to start over. Emmanuel Gersowitz, partner, Message Lab. I actually did get canceled on LinkedIn. In November 2023, I wrote about what I saw as the silence of major women's organizations around reports of sexual violence committed during the October 7th attacks. It connected very personally to work I had done years earlier at Columbia University with Professor Elizabeth Lindenmeyer, Kofi Annan's former chief of staff. She had taught me a great deal about sexual violence in conflict, and above all, About the responsibility to speak about it. The post disappeared from LinkedIn, so I reposted it. There's a line from Albert Camus I've always loved: To name things wrongly adds to the misfortune of the world. My addition would be: Sometimes, not naming things at all is worse. Jennifer Grenquist, diadaya.se. Anything that really makes life worth living, like rave culture, or flowers, art, Art has no place on LinkedIn. The algorithm was not raised to promote human essence. Authentic on LinkedIn is a construct. Enrico Guglielmi, Vinum Italia, vinumitalia.com. The story of how wines were made in Italy and France in the '70s. Dr. Noga Goldst. I don't really think I have any. Chris Heilman, VP Developer Relations, We Are Developers. I don't think there is such a thing as an ethical or empathic multimillionaire, and none of the rags-to-riches stories are true. At some point, you must trade becoming richer than you ever need to be for being a good person, and money, even more than power, corrupts. So all the growth hacking and do it like person X and you will be a success posts annoy me and waste time. Nina Horowitz, immunebridge.com. Writing your post with AI makes you look stupid, and I will not only ignore it, but actively judge you for not writing it yourself. And everyone knows. Norm Howe, Senior Partner, Validation and Compliance Institute. A few posts on LinkedIn say crazy things. If you actually tell them they're crazy, I think you might get canceled. I just stay away from those posts. Everyone can see that they're crazy. Jake. I'm not a clickbait professional and do not air my fringe opinions publicly. Romella Janine, Founder, Lucid Pattern. I speak my mind without worrying about getting canceled because I feel in some ways I have already been canceled due to my last role being in But to answer the question, I think that most folks on LinkedIn are inauthentic and show no hesitancy in stealing ideas from others. That team is not the most important criteria for investors. Investing in people is a trope, and ROI only comes when more important de-risking elements are present, especially timing and addressable market. Real estate developer, founder, IND Consulting, co-founder, Elevate SWFL and Elevate St. Pete. IND Consulting, also Elevate SWFL, Elevate St. Pete. Not everyone should be an entrepreneur. And not everyone who wants the title actually wants the responsibility that comes with it. A lot of people want autonomy, flexibility, and upside. Far fewer want to make the decision when there is no right answer, write the check when things go wrong, Or keep showing up when nobody is clapping. Co-founder and CEO, Mithril. Our actions are mostly predetermined by biology. Even if free will exists, I don't think it negates that. Many businesses like to be seen as customer-focused. Most of them are focused on their own bottom line. I believe humans are uniquely wired for life and success. It takes all kinds to make this world go around. I hold this as a core belief. So, while I certainly disagree with many ideologies, practices, and human behaviors, I am not arrogant enough to believe mine are superior. While I value a good debate and discussion, I am unlikely to push something to a point anyone would seek to cancel me. We can actually disagree and get along. I've been doing it for 50+ years and am arrogant enough to believe that can continue. Ellen Malloy. I'm not sure this would get me canceled on LinkedIn, But it would certainly be controversial. With divorce rates commonly estimated between 41% and 50%, and with many women experiencing a significant decline in financial well-being after divorce, modern marriage should arguably be viewed as a high-risk life decision, one that deserves to be evaluated through a very different lens than it was for our mothers and grandmothers. Women are also statistically more likely to be seriously harmed or killed by an intimate partner than by most other categories of offenders, yet our culture continues to idealize romantic partnership while often treating single women as if they are incomplete, pitied, or somehow less successful. As far as I can tell, many women still grow up believing that their lives are incomplete without a romantic partner. Given the risks and trade-offs involved, perhaps it's time to examine that cultural narrative more critically. Eric Malka, co-founder and managing partner, Strategic Brand Investments. I wrote a book about the toxicity of petrochemicals in our daily lives which I never published. Not because I feared being canceled or worse, but because I felt it was a losing battle for me. Petrochemicals have infiltrated every area of our lives, making our planet and its inhabitants sick, hiding in plain sight. In my area of expertise, the beauty industry, thousands of chemicals make their way onto unsuspecting consumers in billions of products annually, causing health havoc in its path. That is why I have always strived to create products that are free of toxic ingredients. Founder, host, The Heart Leader Podcast, Suivera. Likely the fact that I believe we've overromanticized hustle and undervalued nervous system regulation and safety. Most people aren't underperforming because they lack ambition. They're underperforming because they're overwhelmed, disconnected, exhausted, and trying to create from survival mode. I also believe unconditional love belongs in business. Not as softness or as avoiding accountability, but as the conscious choice to see human beings as more than outputs or assets. Ironically, I think organizations that become more human-focused will outperform organizations that become more optimized. Tomáš Milar, founder, Ekvista/Startupr, also Checkly.com. The question is freedom of speech, right? I'm against censorship that goes beyond the law. Limiting the visibility of controversial content rather than banning accounts. Michelle Mayara, Looch. That all of the advice on LinkedIn is garbage. Investors are morons who are wrong way more often than they're right. Most people on LinkedIn have no idea what they're talking about. Gabriel Osamor, CEO, also CFO of the Black British Initiative, Megasudo. The harsh truth is that investors do not just buy into a vision; they buy into the certainty of execution. Too many founders protect their vision while entirely neglecting. the vehicle. A vision without execution is just a hallucination. People celebrate the hustle, but if you lack the ability to execute within a structured, measurable framework, you are not an investment opportunity. You are a risk. President, the Asia Institute. Humans have deeply destructive compulsions, and thus they can be easily manipulated. There is a myth of us as self-sufficient beings who make our own decisions and are not simply reactive to what is done to us. That myth is necessary for our democratic system, and it is valuable, but it is not scientific. If you speak too honestly about our weaknesses, you will lose the mainstream audience and sometimes all audiences. Yash Gad, PhD, founder and chief executive officer, Ringer Sciences. We dramatically overvalue expertise and undervalue judgment. A lot of very successful people or thought leaders on LinkedIn are excellent at operating inside systems where someone has already defined what good looks like. AI is going to expose that distinction quickly because producing the analysis, the deck, the code, or the recommendation is becoming very cheap. The scarce skill is knowing whether any of it is actually right or good. Ola Yekini, PhD, CEO, EasyPly. Work hard and you'll be rewarded is incomplete advice. Hard work is the entry fee. Strategic relationships, timing, and communication determine who gets the biggest opportunities. Director, Civic Works. When people have written that politics have no place on LinkedIn, I've commented that politics, economics, morality, and ethics are all relevant to a business network, unless the purpose of LinkedIn is to simply compete with Indeed.com and collect resumes. Co-founder, LeadPoet. I don't believe in work-life balance if you want to be exceptional. You have to be unbalanced for periods of time, obsess over what you're building, and be willing to push yourself past limits you didn't think were possible. I'd say I resonate with how Goggins talks about being unbalanced. NomadLife.tv. The smaller the budget, the more complicated the client. The more money there is, the fewer problems there tend to be. And never assume that because you're giving someone a deal, they'll expect less from you. In my experience, they often expect more. Rosalind. Being inauthentic, saying one thing, then doing another, then getting caught. Mark Rust, founder plus CEO, consequentlycreative.com. I feel like people are already getting canceled on LinkedIn. More and more people are relying on AI, and posts are getting more and more inauthentic. My answer would be a lack of authenticity, more junk being automated, and no real human connection or relationship being created. Eva Scalzo, Eva Scalzo Advising. I believe if you misrepresented yourself of your business, you would be canceled on LinkedIn. Another reason could be if you were involved in nefarious activities. Noah Shoman, Silo Digital. Good question. HR departments are oftentimes unnecessary. Can't say that with our ICP. Sergey Serukhov, AntinkoAntinko.com. LinkedIn had a great idea to be a place where professionals meet and exchange ideas. But now it turned into a toxic place where people are trying to sell you stuff, most often what you don't need. Siggy Overtune. Showing my true self and feelings. Ashish Singru. A lot of data and AI programs are funded to postpone decisions, not to make them. As long as the numbers are still being argued about, nobody has to be wrong yet because nobody wants to be accountable. The way human dynamics sometimes work in society and corporate world, sometimes it seems that people do not want to get perfect answers. But get answers with enough noise to play the games of power and influence. The system is largely designed to get people to give their power away to an entity— a corporation, government, educational institution, substance, ideology, or identity— and in exchange, people receive titles, status, money, belonging, approval, and sometimes relief from guilt or shame. But your power is precious. The moment you hand it over completely, you may gain comfort, but you lose sovereignty. I think much of modern suffering stems from that trade. Money is the root of most anxiety, depression, and boredom. Poverty is a true struggle. But too many successful people delay chasing their biggest mission for decades to keep chasing money long after they have enough, and I believe this is the biggest waste of human potential ever. Jay Tokosch, founder and CEO, Note Effect. I think LinkedIn has confused visibility with credibility. Some of the people giving the most business advice have never built, scaled, sold, or survived anything difficult long enough to really understand entrepreneurship. Being an entrepreneur is not posting motivational content from a laptop in a coffee shop. It's making payroll when things look bad. It's carrying responsibility for employees and customers. It's surviving mistakes. It's rebuilding after setbacks. It's operating under pressure for years. The irony is that many of the best founders I know are almost invisible online because they're too focused on actually building. Arvind Vora, Vora Method. This may be a pretty long list, but I can tell you things that have gotten me kicked off of other shows, disinvited from podcasts and TV shows, suspended from social media accounts, and so on. I see public schools as a failed welfare program and private schools as institutions that largely mimic that failed welfare program. I think real education should take up, at most, 4 hours a day, total classwork plus homework, and that anything beyond that is a way to waste time and prevent teenagers from entering and competing in the free market. I think people should start their first businesses by age 14 or so, and that no one should go to college. Most good things in life require and come from discipline, but very few people want to accept that responsibility. Most people don't actually want feedback. They want validation dressed up as a feedback request. I spent 25 years building AVS and running crews, and the leaders who improved fastest were the ones who could hear, that's not good enough, without needing a hug afterward. The psychological safety conversation has gotten so soft that a lot of managers are now afraid to just tell someone their work is bad. Shane Wilson, Citta Capital. Being a good person isn't about picking the right set of bumper stickers. A general comment on tribalism and broad-stroke morality. Speak to the tribe, get your likes. Likes slash equals right? Good. Fulfilled Eli Zemor, founding partner, Awake Partners. The vast majority of VC funds that raised money from 2022 onwards are actually losing money. It's the ultimate elephant in the room. While LinkedIn is full of people celebrating valuations, the reality is that many of these funds are completely unprofitable right now. Question 2: What decision looked stupid when you made it but turned out to be one of your smartest bets? About a quarter of the answers are some version of I left— a job, a company, a PhD. The decision that looked stupid is usually the one where someone walked away from the thing everyone else wanted for them. Paul P.K. Loomy. In a prior iteration of myself, I worked in PR on the agency side. In the '90s, I worked for a major international firm and was doing quite well. I then quit to be a freelance writer, which was the part of my job I loved doing. People thought I was nuts to get off that escalator, and so many colleagues went on to great financial success. But I wanted to be independent, and it put me in the right lane to seek opportunities and trained me to be more reliant on my own best judgment. Zions174. Owner, Fasts174. I hired my lead designer's sister-in-law who lives in Vietnam. It's been almost a year now and she's crushing it. I think I said hi to her once. She doesn't speak English. It's a design role, so she just translates all of our notes using an online tool. Founder/CEO and podcast host, The Marketeer Group. To be honest, started the podcast seemed like a waste of time. It was time spent on something that didn't bring in revenue, cost me money to produce. I had no followers, no idea what I was doing, and no confidence. Yet it was one of the best decisions ever. Michelle Iberdini, President, Beeline Legal. Where to begin? Almost all the decisions in my life that have led to the happiness I now enjoy were things I tripped over while I was looking somewhere else. Joining a tiny AI startup after leading engineering at a successful scale-up. To many people, it looked like a step backwards— a smaller company, more uncertainty, and fewer resources. But I wasn't optimizing for prestige; I was optimizing for learning. I wanted to be closer to the product, closer to customers, and on the steepest learning curve I could find. When generative AI started taking off, I became convinced it would redefine great engineering leadership. I wanted to be in the arena where those new rules were being written, not where people were debating whether they would matter. Looking back, I wasn't really betting on AI. I was betting on a future where small, exceptional teams would create dramatically more impact than ever before. Matt Blumberg, CEO, Markup AI. Taking the CEO job at a 20-year-old German legacy software company that was being disrupted by AI Right as everyone was declaring rules-based systems dead. Turned out the company wasn't dying. It was sitting on the solution to the biggest problem AI just created. We renamed it Markup AI and are now building the governance layer for the entire AI content explosion. Quitting my corporate job. CFA, President, N3 Business Advisors Inc. Choosing to focus deeply on construction businesses instead of trying to serve every industry. It looked limiting, but specialization gave us the depth to understand how these companies actually create, lose, and transfer value. Tom Charman, co-founder, Block. Going all in on behavioral simulation before the market was ready for it. People thought it was too academic, too niche, too weird. Even investors would say things like, why not just use surveys? Or, LL, Ms. can already do this. Meanwhile, we were obsessing over modeling how humans actually behave step by step inside products. At the time, everyone wanted dashboards or copilots. We were building infrastructure to predict human behavior before anything ships. It looked like overkill. Now build cycles are collapsing because of AI, and suddenly everybody realizes validation has become the bottleneck. That's where we come in. Patanjali Chari, CEO and founder. Fourth vital: choosing to study artificial intelligence at the University of Toronto. In my year, only 3 of us graduated with an honors BSc in computer science and AI, and many employers still thought AI was science fiction. I was the founding president of our Cognitive Science and AI Society, and we struggled to attract anyone beyond my classmates. That is certainly not a problem anymore. My mother cried because I had not chosen electrical or computer engineering like every other normal South Asian student, I told her, Mom, I'm not studying for today. I'm studying for the future. Mark my words, one day AI will be all anyone talks about. Now, through Fourth Vital, I am using AI to help detect kidney decline earlier, a mission driven by the kidney failure that took her life. I only wish she were still here to hear me say, I told you so! Federico Sismondi, BRNDTS. Leaving science? I had just finished a PhD program that was a joint effort between MIT and Harvard Medical School, working at the top of medical informatics, with the chance to work for some of the biggest companies building electronic medical records in the world. I decided to take a job in the Middle East instead, one that gave me time to build my own business. That was my first step toward entrepreneurship, walking in the opposite direction from being a scientist. At the time, professors and even my own family told me I'd invested years in my PhD and was throwing it away. I don't regret it at all. It turned out to be my smartest bet, the one that brought me the most success and happiness, because I started pursuing what I actually wanted, not what a professor or research department wanted because it served their interests. Danny Cohen, Sticker.VC. In 2019, I invested in Rooty, a fashion brand with $6 million of revenue, mostly in retail. Nobody understood the investment, and I probably made it for the wrong business. However, company did not take any additional money, is on track to reach $100 million of annual revenue. Jiraj Shvik, CEO and CMO, Trama Tramatem. Overinvestment into performance marketing in the early days of Trama. As a startup, pretty much everything is 80/20, cutting corners where we could. So with a false assumption about our profit margin, we ended up running performance marketing at a substantial loss. In hindsight, it did, however, allow us to grow much faster. Getting that product market fit sooner, speeding up A/B testing and getting us a loyal customer base that runs with us. Hiring a person with zero marketing experience to run my content marketing just because I saw a glimpse of raw natural talent. Motivation. Instagram marketing secrets. Making a YouTube video predicting the Bitcoin crash of 2021 a month before it happened and getting flamed in the comments until then. I was getting an idea going. It was taking too long, so just started. Reliquents. After defining the Planetary Address Framework, I experienced a long delay before seeing a viable business model for the planetary maps. My end product is a completed digital map with sufficient coverage of planetary roads to become the de facto standard once those maps proliferate. The Planetary Address Framework looked simplistic when I first discovered it, but the more I explored its implications, the better it got. Paul Foley, founder and executive chairman, Bulk Exchange. Leaving a successful career in heavy civil construction to build a technology platform with no technology background. I had spent decades on job sites across 3 continents. Everyone I knew thought I'd lost the plot. A construction guy building a marketplace? I didn't know what a tech stack was. What I did know was that the industry was broken. Procurement was still running on phone calls, favors, and gut feel. And nobody from the inside had tried to fix it. Six years later, Bulk Exchange is still the only true marketplace for heavy civil materials in the market. Sometimes the outsider perspective is the edge. Michelle Friedman, founding partner, Reflect Ventures. Honestly, when I make the decision, it usually looks smart. It is sometimes dumb in retrospect. For example, the first time GameStop spiked, I made a very substantial amount of money on short duration puts betting it would drop. When it spiked again about a month later, I tried to repeat the trade, doubling down. Ouch. GameStop price did not collapse again until end of the year, by which time my options has expired worthless. Paula Finbow. Passing a deficit budget. On paper, it looked risky, especially in a turbulent year for nonprofits to build pay equity and better benefits for our staff. But I wasn't betting against the budget. I was betting on our people. When federal cuts hit us hard last year, it was that same staff, the ones we chose to invest in, who showed up the next day, no funding, no contracts, and kept teaching anyway. It's an investment worth making. PhD, Georgia, and Molly. Selling my shares and leaving the CEO role of a growing product management training/consulting business to become a project manager for an electric dirt bike. I was promoted to CTO less than 3 months after I joined. Emmanuel Gershowitz, partner, MessageLab. Moving to Israel. On paper, it probably made very little sense. I left behind a much more obvious and predictable path. But some of the most important decisions of my life have made sense only in retrospect. Moving to Israel completely changed the trajectory of my life, personally, professionally, and intellectually. Jennifer Grunkvist, dia dia.se. Quitting my job without a plan B has always been extremely productive. Enrico Guglielmi, Vinomitalia, vinomitalia.com. Being boutique in the selection of rare and unique wines, Dr. Noga Gulst. In 2002, I have opened my first venture. After 2 years, we were stuck with 100 clients, the same 10 clients we had a year before. I thought we were failing. My partner thought we were succeeding. I left the business, did my PhD, and learned all I could about business failure and how it can help you. Thanks to that decision and my PhD, I created my ideation evaluation model. Chris Heilmann, VP Developer Relations, We Are Developers. Moving to another country for a job, leaving everything behind. As it turned out, this gave me the drive to start a new life there without relying on my earlier successes. Communicating in a secondary language and immersing myself in a different culture gave me great empathy for people I hired later on worldwide and enabled me to work anywhere, anytime. Nina Horowitz, immunebridge.com. Some of our collaborations are with tiny biotech startups or academics with limited funding. They don't fit our perfect ICP, but they've generated some of our most interesting and compelling external validation data so far, and they are always willing to try new and creative experiments. One of the workers made a bad mistake. I invited him to a bar and bought him a drink. Forcing executives to reassess COVID before it became an epidemic. That resulted in the largest growth year in the company's history. I think the verdict is still out on that. I think I am in the midst of that decision now. To be completely honest, I am currently struggling with Lucid Pattern, and I have started a few channels on YouTube that don't have very many subscribers. We'll see. I'm taking a risk on myself. John. Depleting almost all of our cash on hand to acquire another company. Christy Candle, real estate developer. Founder: IND Consulting. Co-founder: Elevate SWFL and Elevate St. Pete, IND Consulting, also Elevate SWFL, Elevate St. Pete. Leaving a very good corporate job to start my own company, I left my W-2 in 2015 and started my own company. From the outside, it probably looked like I was walking away from security. Looking back, I was betting on my ability to figure things out. That decision changed the trajectory of my entire life. Brandon Karpelis, Chief Executive Officer, Sovereign. I guess I would have to ask who it looked stupid to. If it is the rest of society, Things like not taking an experimental pharma product when the rest of the world did, putting my whole net worth in Bitcoin, and trusting that God has a plan for me all come to mind. If it is something I thought was dumb but turned out well, it would be not pursuing a law degree. I thought I would make less money, have trouble finding what I wanted to do, and be giving up what I thought I wanted to do my whole life. Everything all worked out great, and I am incredibly happy that I am not an attorney. David T. Kim, co-founder and CEO, Mithril. Dropping law school. I was broke, desperate, and entered a web novel contest. I wrote a fantasy basketball novel that became one of the first sports web novels to cross 1 million readers. At the time, it looked irresponsible. It ended up turning into Mithril B. Kim, hiring someone with no experience in the industry who turned out to be very effective. Ellen Malloy. One example was my business plan for an alternative health expo in Richmond, Virginia. The plan called for renting 20,000 square feet of exhibit space and attracting 200 exhibitors. Despite the fact that no integrative or alternative health expo in the region had been financially successful or well-attended in the previous decade, to many people, the idea seemed unrealistic. My business partner believed in the vision, and we moved forward. The inaugural event attracted approximately 700 attendees, and subsequent expos grew to around 1,200 attendees. The success of the event demonstrated that the market opportunity existed; it simply required a different strategy and execution than previous attempts. Eric Malka, co-founder and managing partner, Strategic Brand Investments. Selling my car to open a tiny shop on Manhattan's Upper East Side to sell premium shaving products. Ten months later, I doubled down by opening a flagship store on Madison Avenue to sell eighteen dollar shaving creams. Amber Mikesell, founder, host, The Heart Leader Podcast, Suivera. Building Suivera, our all beliefs religious organization, exactly as it stands today. We are a safe space for anyone and everyone to gather to explore what they believe and why they believe it. Representatives from every culture, belief system, knowledge level, all gather together with a curious mind and an open open heart to support their own self-exploration and the exploration of others. People told us repeatedly as we started, niche down, choose a known religion and stay in that lane. Pick a demographic. Don't attempt to include everyone or you'll include no one. Instead, we built an all-beliefs church and global movement that includes anyone who opts in and is willing to gather around curiosity, human connection, and becoming love in action. When Suivera started, it may have looked like a stupid and unachievable idea to many people because it was a new concept and a Lofty one at that, but over time people realized they weren't starving for answers; they were starving for spaces where they could ask questions safely, allowing them to understand what they were even searching for in the first place. So our bet on our concept and willingness to move forward has paid off greatly as we've grown to 1.3 million members in 113 countries and a global outreach arm that provides aid to many in need. Tomas Milar, founder, Ekvista/Startapar, also checkly.com. Saving money. When I moved to Hong Kong, everybody was living in flashy apartments, $5,000 to $8,000 rent/month. I was sharing an apartment and was paying $350. I could use that money building businesses. Now, we have Equivista worth of crazy money, multiple businesses, and those who spend this money on apartments early moved out and burned out by chasing luxurious lifestyle. Michelle Miara. Not launching Looch until it was complete and fully polished. Not launching another MVP. CEO, also CFO of the Black British Initiative, Migasuto. Transitioning from nearly a decade in investment management, where I engineered financial frameworks to deploy billions for global funds, to bootstrap my own fractional CFO firm. Stepping into strategic stewardship and executive leadership as the CEO of Migasuto and the CFO of the Black British Initiative, BBI, looked like an unnecessary risk. However, that exact decision allowed us to unlock nearly £500,000 in capital for our ecosystem within the first 6 months. More importantly, it positioned us to drive the MBA30 program, delivered in partnership with SOAS University of London. This isn't merely an educational initiative; it is a national infrastructure project for equity designed to safeguard the financial future of the next generation. We bridge the gap between street-level resilience and institutional boardrooms. Emmanuel Pastreich, President, the Asia Institute. I had this vision when an undergraduate that Asia, and specifically China, Japan, and Korea, would be the center of geopolitics in my lifetime, and that I doggedly learned those 3 languages and understood the cultures that would be decisive. The value of that decision would not be clear until my late 50s. It was not stupid, but it seemed a bit obsessive at the start. It also did not translate into wealth, but it did give me influence. PhD, founder and chief executive officer, Ringer Sciences. I built Ringer to be intentionally hard to categorize. For a long time, everyone wanted you to be a SaaS company, an agency, a consultancy, or a data company. I wanted people who could move from the business problem to the data, to the AI, to actually building the thing. And I pivoted the team hard in that direction. It looked unfocused for a while. Now AI is collapsing those boundaries anyways, which makes us look ahead of the curve. What looked unfocused five years ago looks a lot like how companies are going to be built five years from now. Ola Yekini, PhD, CEO, EasyPly. Building EasyPly while working a full-time job. A lot of people thought I should wait until I had funding, a bigger team. Or the perfect time. Instead, I spent nights, weekends, and every spare moment talking to job seekers, recruiters, and founders. We built, tested, failed, improved, and kept going. Today, Easyply is live, helping professionals create talent passports and making it easier for recruiters to discover talent beyond traditional resumes. Director, I try to avoid the perception of stupidity when I can. Leaving Oracle toward the end of 2016 was a bold move, and I encountered an array of opinions. It was the right thing to do then and experience since my resignation has more than supported my very public departure. Leaving Nasdaq to build LeadPoet full-time? We walked away from stable careers before the outcome was obvious, but that decision forced us to move faster than we ever could have while doing it nights and weekends. Jason Rhodey, NomadLife.tv. Two things come to mind: selling Moment Factory and buying my first commercial building. In both cases, pretty much everyone around me told me it wasn't the thing to do. They turned out to be two of the best decisions I've ever made. You have to follow your intuition. Rosalind. I can't think of one, but I can think of a decision that looked smart at the time but turned out kind of stupid. When we were first designing out our website, we spent Way too much time designing, testing, and perfecting, trying to imagine what features our potential customers would want. In hindsight, we should have launched an MVP as soon as possible and let actual customers decide what features they want and don't want. Mark Rust, founder plus CEO, consequently creative.com. Answering all these questions, haha. Eva Scalzo, Eva Scalzo advising. I decided to move into a high-end office building from my smaller office, and although financially it was a stretch and looked stupid when I first did it. My company has grown into the side and it is one of the best decisions I made. Noah Shoman, Silo Digital. Leaving the big corporate bank. Sergey Surukhov and tinkoandtinko.com. Leave corporate golden cage to start my own business. Siggy Overtune. To found a startup. Ashish Singru. Taking the general manager role in Bangalore instead of staying close to headquarters. Moving away from the center reads as a step sideways, and it is the reason I have P&L and general management on my record rather than only functional analytics leadership. But the kind of corporate, domain, and personal experiences I gained from that choice are worth writing a book about, which would never have been written if I had taken the other path. Starting my first company in financial services in 2008, directly into the teeth of the great financial crisis. From the outside, It probably looked irrational. The market was melting down, trust in financial institutions was collapsing, and capital was scarce. But that environment forced clarity, resilience, creativity, and discipline. It became one of the best decisions I ever made because it taught me how to build when the world is uncertain. Neil Thanedar. Getting into politics again in 2017, right when so many people were at their most disillusioned with politics, was one of the best decisions I've ever made. I saw a path to a more positive politics, starting with activism focused on bills and actions over attacks and divisiveness. We're closer to this path now, but need more ambitious optimists to get into politics and do good now. That's what I'm doing now with my book Positive Politics and the Positive Politics Accelerator. Jay Tokosch, founder and CEO, Note Effect. Building Note Effect the hard way instead of chasing fast money. I could have built another narrow SaaS tool, raised capital around hype, and optimized for a quick flip. Instead, I spent years studying how people actually lose knowledge inside organizations. Meetings, presentations, training, sales calls, documents— all disconnected. People thought I was building too broadly and going scorched earth. What I was actually doing was building the intelligence layer underneath how enterprise knowledge will work in the AI era. That looked slow to some people, but now the market is moving exactly where I believed it would. Arvin Vora, Vora Method. The very first step: choosing to start an education business instead of going into finance along with the rest of my friends. I was a math and econ major at Brown. Most people predicted that the experiment would last a month or two at most. Brian Wally. Six months out of college, I was offered eighty thousand dollars to stay at a job I did not respect, but I quit to earn a real wage at Mammoth Mountain Ski Area for nine dollars and. Walking away from a company I spent 25 years building. Founders are told never to leave the thing they built, it's treated like abandoning a kid. But staying past the point where you're still growing is its own kind of failure. I left AVS to build a coaching and content business from scratch, at a point in life where most people are coasting toward retirement, not starting over. I'll tell my college football story. Eli Zemor, founding partner, Awake Partners. Launching our podcast with my co-founder, people told us we were wasting our time and that we should focus 100% on cold sales. But giving a platform to others instead of just pitching ourselves turned out to be our best moat. It built unshakable credibility and a massive network. Question 3: When did you realize you were playing a completely different game than everyone else? The hardest one to answer in a sentence. People tell a story of the moment instead. Read Megan Eskey and David T. Kim for 2 very different games. Loomy. I'm not sure I'm playing a different game, but I think those of us who are mission-driven self-impose a different set of rules. Some of us get to the end of the year and look back to assess what sort of impact we've made. I'm not sure everyone asks that same question. Fast ends 174. Owner. FAST ends 174. I sometimes like to compare life to a board game. We're all playing the exact same game, but we get to determine the scorecard for ourselves. So you get to choose whether you play for money, fun, impact, charity, connections/relationships, and so on. I like that framing, and sometimes it helps me understand someone's actions that don't seem to make sense. They're playing the same game, but scoring it differently. Founder/CEO and podcast host, The Marketeer Group. When people started knowing my name, it was so strange when they would say, I think I know you, or, I listen, and so on. President, Beeline Legal. High school. But then I got to college and found out there actually were other people playing the same game. I realized I was playing a different game when AI changed what it meant to scale a company. For years, I'd been optimizing for impact instead of size. I believed in solving problems through better systems, automation, and exceptional people before adding more complexity. While many companies measured success by headcount, I cared much more about the impact each person could create. When generative AI became practical, I realized those ideas were no longer as contrarian as they once seemed. AI made it obvious that competitive advantage would increasingly come from enabling smaller teams to accomplish dramatically more. It felt like the market was beginning to reward the same principles I'd been building around for years. Matt Bloomberg, CEO, Markup AI. When I looked at the AI landscape and realized everyone was racing to generate more content, and nobody was asking who's governing all of it— it's 2000 all over again. Everyone sending email, nobody thinking about email deliverability. I'd seen this movie before. Different theater, same plot. Bora, reacherapp.com. After getting into YC and meeting all these gifted founders, Nitin Khanna, CFA, President, N3 Business Advisors Inc., when I realized most advisors were optimizing for a transaction while I was thinking about what makes a company valuable years before a sale. The real game is not selling a business. It is building one that can thrive without its owner. Honestly, probably from my background before startups. Working around intelligence and behavioral modeling changes how you see systems. You stop looking at what people say and start looking at incentives, pressure, uncertainty, emotional states, environmental constraints. I think the moment it really clicked in tech was realizing most companies were treating product development as a reporting problem, measure what happened after launch. We were treating it as a prediction problem. Completely different worldview. CEO and founder, Fourth Vital. I realized it only in hindsight. At 17, I started a software company from my bedroom at home. Despite having customers and revenue, my parents were furious when I took a year off before university to build it. I later moved the company into my University of Toronto dorm and tried to run it while studying AI. I thought I could juggle everything. I could not. Both my grades and the business suffered. Later, in Singapore, I helped build what we then called Massively Multiplayer Edutainment, a 3D metaverse for children, written in Java during its earliest days and pushing the technology far beyond its limits at the time. Eventually, the pattern became clear. I kept building for a future before the market even had language for it, With Fourth Vital, I am still playing that game, but after years of being early, this time around, the timing finally feels right. Federico Sismondi, BRN DTS. I realized I was genuinely good at two things. First, building a team with no fear of tackling problems other technical teams shy away from, whether out of financial fear or technical complexity. We went after those problems and nailed them. Largely because I could build a young, fearless team that knew management had their back to find or invent a solution. Second, I could speak both languages, business and technical, understanding a problem as a client or partner described it and translating it for our technical team or CTO into real projects and goals. I realized both of these halfway through building my previous company, DODoc, working with pharmaceutical companies with over 100,000 employees. We were doing things that impressed them and communicating it in a way that got them excited, not just informed. That combination of fearlessness and business communication made the difference. Danny Cohen, Sticker.V. When Cyber and Infra took over the Israeli VC scene and I decided to double down on B2C, it was clear that I am playing a different game. I don't know if this is a right decision, but right now I am moving away from the focus of everyone else. The first act of my career was as an officer in the Navy. In subsequent acts on Wall Street and as an entrepreneur, I've come to find that qualities I've assumed everyone in a competitive environment would have— accountability, word is bond, getting things done in timely/quality fashion, if you say you have the expertise, you actually have it, and so on— are more rare than I realized. So I wouldn't say I'm different than everyone else, but qualities I assume are inherent It turns out are not. Craig, the FBCG. When I realized that the overwhelming focus of those serving businesses was on large, often public corporations, and that family-owned businesses, which combined the complexities of family dynamics with the challenges of business success, were ignored. Juraj Svick, CEO and CMO, Trauma Trauma Tem. Few moments. One of them was definitely when our well-established competitors started bidding on trauma keyword Derek Instagram marketing secrets. When I heard how many entrepreneurs make excuses for failing that don't sound legitimate, Duncan. When I felt like a Cassandra, seeing the moves ahead when no one else did, or wouldn't accept Megan Esky, president, reliquents, I was amazed to discover that there were no historical precedents for the planetary roadmaps. At no time in history has another human made maps of the moon and Mars that include a system of roads. Why not? Even the early astronomers could have made rudimentary maps by drawing routes between the landforms that they viewed through their lenses. Certainly during the Apollo era, while men on rovers were roaming the surface of the moon, I would have expected to see a proposed system of roads at the various lunar landing sites. Space mining is still a ways off, but that is another target market for planetary roads, yet no one else is playing in my sandbox. Paul Foley, Founder and Executive Chairman, Bulk Exchange. Day 1 of Bulk Exchange. When I looked at the heavy civil materials procurement space and realized nobody, not a single company, had built a true marketplace for it. This is one of the largest, most capital-intensive industries in the world, and buyers and suppliers were still operating the way they did in 1985. We weren't disrupting an existing product. We were building a category. That's a different game entirely. To this day, we're still the only one doing it. Honestly, when I passed up 2 promotions early in my career because I didn't think I had what it took to lead, I'd been told, repeatedly, that leading with your values was too idealistic, too rigid. It wasn't until I built my own values-and-decision-making scorecard and watched it hold up under an actual crisis that I realized the roadmap I'd been waiting for didn't exist because I was supposed to build it. Petropharm, PhD, Georgia, and Molly. Pretty early, perhaps 8th grade, I did a mandatory internship at a low-price cloth store. The way you lost control of your life pissed me off, and I was like, "Yeah, one day I'm gonna own this business." Emmanuel Gersowitz, partner, Message Lab. Every day, everyone is talking about AI algorithms, social media reach and scale. I'm still obsessed with depth, language, and meaning. I don't think technology makes those things less important. I think it makes them more important. Jennifer Grunquist. deadea.se. I could never fit into any format. Once I entered work life, it became obvious quite quickly that the nerds liked me. Pretty much everyone else found me really annoying or weird. And so I navigated that going forward. There has never been a role model I can relate to for my work. vinometallia.com. When rare products sell more than classic ones? When I understood that I needed to educate my prospects in the importance of evaluating ideas before spending more time and money on it, Chris Heilmann, VP Developer Relations, We Are Developers. In almost every step of my career, people kept asking me why I didn't start my own startup and sell it big to a large company. Instead, I joined larger companies and tried to improve them from within. Instead of trying to move up the ranks fast in these companies, I focused on seeing the potential in others and supporting their advancement. I have a massive network of people who became highly successful after I removed some barriers for them. Many are richer and more successful than I am, but I feel more satisfaction from that than from building and discarding things only to get richer. Nina Horowitz, immunebridge.com. When some of our competitors started coming to us for screening, ML models, and manufacturing partnerships, clearly we're onto something important, and it's not easy to build or they would do it themselves. Norm Howe, Senior Partner, Validation and Compliance Institute. When realized that everyone else in our business, which is quality compliance in FDA-regulated businesses, was from a regulatory background while we came from production. We are the only ones who have the responsibility of getting product out the door on time, on budget, and compliant while making a profit. Everybody else was either ex-FDA or had grown up in corporate compliance. Jake. When I was making more than most of my friends who had an MBA or PhD. Romella Janine, founder, Lucid Pattern. Early on, but being able to act on it meaningfully is very recent. John. I don't know that the game is necessarily different. I think it's more like who's playing the game and how are they playing it. This did not become apparent to me until my first startup was acquired by Daimler Mercedes. Christy Candell, real estate developer, founder, I&D consulting, co-founder, Elevate SWFL and Elevate St. Pete. I&D Consulting, also Elevate SWFL, Elevate St. Pete. When I stopped optimizing for income and started optimizing for ownership, optionality, and impact. Making more money is great, but eventually I realized I wanted to build things I owned, create places that mattered, and have control over what I spent my time working on. That changed the game completely. Brandon Carpeles, Chief Executive Officer, When I realized that I didn't just want to work 9 to 5 for 45 years and then do nothing in retirement outside of travel, golf, and eating out as my body deteriorates faster than it ever has. Kim, co-founder and CEO, Mithril. When my novel got licensing and adaptation offers, everyone treated it like I had written a book. I realized the valuable thing was the world inside it. The characters, objects, lore, and the audience's attachment to them. Probably when I was about 9. I was more focused on science and outdoor activities than on traditional girly pursuits such as playing with dolls. When I was 25, a male colleague and I, both working in Capital One's customer service department, were selected for an internship in the company's marketing and analysis division. I assumed we would be assisting an executive. Instead, we were each assigned 12 marketing projects and given 3 months to complete them. 2 weeks into the program, my colleague resigned. I took on his projects in addition to my own and successfully completed all 24 assignments within the internship period. As a result, I was promoted 3 levels at once. That experience became the launch point for my career in IT project management. More importantly, it was the first time I recognized that I approached problems differently than many of my peers. I could often identify solutions more quickly, see patterns others missed, and anticipate risks before they became visible to the rest of the team. Those abilities would later become defining strengths throughout my career. Co-founder and Managing Partner, Strategic Brand Investments. During the first 2 years in operation, we realized we had stumbled onto one of the only consumer product categories that didn't serve premium consumers. The affluent and mass-market consumers bought the same shaving products in the same mass-market retail venues. It was an anomaly we were the first to rectify. Founder, host, The Heart Leader Podcast, Suivera. When I realized I wasn't trying to win, be right, scale the fastest, dominate a category, instead I was creating conditions where people become more themselves. Once I understood that, competition became less interesting than contribution. It sets the parameters for how I build, speak, lead, and partner. Founder, Ekvista/Startupper, also Checkly.com. When I was 20, I would work crazy hours, 18 hours a day, summer jobs, walking with $35,000 away each summer. Looch. When I realized I do my best work from home overlooking the ocean with my dog, avoiding meeting at all costs. CEO, also CFO of the Black British Initiative. Migasudo. When I dug deep into the macro data and confronted the staggering £781,000 revenue gap, seeing that the median turnover for a Black-owned business is just £25,000 compared to the £806,000 UK national average was a turning point. Everyone else was playing the game of networking and motivation. I realized this wasn't an inspiration problem, it was a structural problem. While others were trying to teach founders how to speak better on stage, I started rewiring their financial plumbing. I realized I'm not playing the accounting game. I'm playing the economic justice and resilience game, using capital efficiency as my weapon. Emmanuel Pastrike, President, the Asia Institute. It is clear that I was playing a very different game from almost anyone else, especially when it came to diplomacy and then to politics from early on. I was interested in changing how things worked, not advancing my own career. I guess I started to a sense that institutions in America were in ineluctable decay in junior year of college, 1986. I felt that the only solution was to change everything, and that radical change was possible, but that it required a larger complete vision for the totality of civilization to succeed, and it required patience. Yash Gad, PhD, founder and chief executive officer, Ringer Sciences. I think my superpower has always been starting with the outcome and working backward. I saw this really turn heads at an agency, and more so as soon as I started Ringer. I do not get particularly attached to the process, the org chart, the software stack, or the way something has always been done. I want to understand the actual objective, then work backward through the technology and the process to find the simplest way to get there. That has led to some pretty dramatic rethinks of how work gets done and how technology fits into people's everyday lives, and I I do not think we are close to finished. AI is going to force us to question a lot of structures we have treated as fixed simply because they existed before the technology did. Olayekini, PhD, CEO, EasyPly. I realized I was playing a different game when I moved to the U.S. I arrived with years of experience and confidence that my work would speak for itself. It didn't. I quickly learned that talent alone isn't enough when no one knows who you are. That experience taught me that opportunities don't just follow qualifications; they follow visibility, credibility, and relationships. It completely changed how I approached my career and ultimately inspired me to build EasyPlay. Sometimes the biggest career breakthrough isn't learning a new skill; it's learning a new game. George A. Polisner, Director, Civic Works. I'm standing on the shoulders of pioneers in an array of different and important disciplines, I don't think it's a different game. I'm using different measures of success. Co-founder, Lead Poet. When we realized Bittensor could let hundreds of independent agents compete to improve our product? Instead of trying to outspend larger AI companies on centralized R&D, we could turn a decentralized network into an experimentation engine. NomadLife.tv. As a teenager, I was already aware that I was different. I approached almost everything creatively and was always working on several personal projects at once with different collaborators throughout my school and community. But it was during my last year of university that I realized I didn't want to compete on the same field as everyone else. I wanted to create my own. Rosalind. When people are surprised by the fact that the majority of our clients are non-Chinese foreigners hiring Chinese confinement nannies? It affirmed me that the niche we saw in the market indeed exists, and we did a good job educating people that are not of our cultural background of the importance of postpartum care. Mark Rust, founder plus CEO, consequentlycreative.com. Pretty early in life, once I realized that being interested in different things makes you interesting, learn a musical instrument. Focus on something and get really good at it. That makes you stand out, and it makes life easier for you. Believe it or not. Eva Scalzo, Eva Scalzo Advising. I realized I was playing a completely different take when I realized the depth of my experienced AAVE background in the industry versus most other individuals out there. Noah Shulman, Silo Digital. When I was working in a bank at 19 while my friends were doing work and travel. Sergei Surukhov, antinkoantinko.com. When company where I worked starts seeing me as a troublemaker. And I heard, it looks like a great idea, but I won't give you a penny for that. Overtune. When I wanted to do music tech. When I first started working with finance, I was told CFOs love dashboards. Fast, furious, and more the better. But when I saw the CFO trying to figure out the story of their business from one quarter to the next, called a performance walk in their parlance, and saw them dance and dodge their way through the dashboards to create that view, I felt I needed to add more science to that art. So I deployed the power of my 100-person team that had different pieces of the performance puzzle across the e-commerce business at eBay to work together and create a scientific walk that could help the CFO with a data-driven and logical approach to capital allocation. I stopped competing on volume of output in form of dashboard and starting differentiating my value, my quantifying the levers that made the walk from one quarter to next real. Jack Swift, when I quit Janus Henderson. I was young, had a family, and had a path that looked safe and successful from the outside. Leaving that security behind as a young dad felt like stepping off a cliff. Funny story here about when I made the decision and what my buddy said to me, but I realized I was no longer interested in optimizing for safety. I wanted to build, create, learn, and live closer to the edge of what felt true. That was the moment I knew I was playing a different game. When I talk about my plan in decades, it shocks startup founders and investors who have gotten stuck thinking in 10-year fund cycles. Most of the work I've done in the first 15+ years of my career hasn't paid off yet, and that's intentional. I've invested heavily in getting to where I'll have the most positive leverage on the world. Founder and CEO, Note Effect. When I stopped optimizing for features and started optimizing for infrastructure-level problems. Most founders I run into are building applications. I realized I was trying to solve the institutional problem of memory, knowledge retention, workflow intelligence, and secure AI recall across organizations. I guess this is how I saw it as a completely different game. It also changed how I viewed time. I stopped caring about whether something was trendy this quarter and started thinking about whether it would matter in 10 years. Vora Method. Pretty early on, probably high school. The things that mattered to most people didn't matter to me in the same way, and the things that no one cared about mattered to me a lot. The nature and quality of education mattered a lot to me. I didn't understand why the supposed elite private school I went to seemed so utterly indifferent to educational efficiency and was so happy to waste student time. Educational efficiency ended up shaping much of my life. Most people just want payroll to exist, and some people make payroll happen. Sitting in Army ROTC training, Fort Knox, jungle training in Panama, cold weather training in Alaska, next to guys headed for the military while I was headed for broadcast and media, I realized leadership under pressure isn't industry-specific. Most business people are optimizing for the next quarter. I was trained to think about what happens when the plan falls apart completely, which is exactly what led me into disaster preparedness training later on. Shane Wilson, Citta Capital. In business school, everyone was there to get a good job and explore options. I was on, and still am on, a single track mastering VC Eli Zamor, founding partner, Awake Partners. The day I started posting on LinkedIn. I looked at my content and realized I was saying the exact same vanilla things as everyone else, taking zero risks. My co-founder and I decided right then to stop trying to be influencers and become connectors by launching the podcast. We changed the game entirely. Question 4: If you lost everything tomorrow, what exact steps would you take to rebuild in 90 days? 20 of 64 start with their network. Call the people who trust you before anything else. A handful refused the premise. 90 days is not realistic. I wouldn't rebuild; I'd change direction. One guest answers from having actually been through a medically induced coma, so read that one slowly. You can lose almost everything without ever losing your purpose. Patanjali Chari Paul P.K., Loomi. I can't say exactly how I'd respond to a total wipeout, if that's the question, but Loomi is our 4th venture in the past 8 years. The first three went under for different reasons, but each one was a learning experience and led us to other ideas we wanted to try. If you're trying to make an impact and you have confidence in your idea, you have to be willing to gather yourself up and try again. I think people fear repeating a failure, but a bigger fear for me is getting to the end of it all and wondering what would have happened if I'd tried again. Fast signs 174 owner. Fast Signs 174. A lot of my friends asked about the risk of owning a business. I think about risk a little bit differently. In my old roles, I could be fired at any time. You might be thriving in your role, and that role simply disappears. Owning the business, I cannot get fired. I can only lose the business. And the benefit is that I should almost always see it coming. We're not at a penstroke government risk or even a sudden AI risk. But to answer the question, the skills I've learned running this business for even a few months make me far more valuable in the marketplace than 5 years in my old role. I learned more, had greater responsibilities, and doubled down on my strengths. Founder/CEO and podcast host, The Marketeer Group. I would establish a point of view on something, go all in, network like crazy, and put myself out there, talking to as many people as possible. Listen to their pain points and needs, and build what the common denominator is. Michelle A. Berdinas, President, Beeline Legal. If I lost everything, I couldn't rebuild. I would need to have my health and my professional reputation. In that situation, I would just start having meetings with people I trust and keep my mind open. Darío Blanco. If I still had my experience, my network, and my reputation. I wouldn't see it as starting from zero. I'd see it as a rare opportunity to start from scratch with everything I've learned. The first month would be spent talking to founders to understand what problems they keep running into. One thing I've learned is that the best businesses often come from boring problems that everyone accepts as just the way it is. The second month would be about building and validating a solution as quickly as possible. The third month would be about doubling down on whatever shows real traction, whether that's creating a company or joining an exceptional team. Matt Blumberg, CEO, Markup AI. Week 1: Call 20 people I've built trust with over 35 years, not to ask for anything, just to say, I'm starting over. What do you see? Week 2 to 4: Find the problem that's painful, urgent, and poorly served. Week 5 to 8: Build a prototype with AI tools you can build in days what used to take months. Week 9 to 12: Get 3 paying customers. Not users, customers. Reputation and relationships are the only assets that survive any catastrophe. Everything else is rebuildable. ReachYourApp.com. This is hard, depending on what I want to do next, this answer would change. CFA, President, N3 Business Advisors, Inc. In the first 30 days, I would speak with as many construction owners as possible and identify one expensive problem they consistently face. In days 31 to 60, I would solve that problem for a small group and turn the results into referrals. In days 61 to 90, I would systemize the service, build recurring relationships, and reinvest every dollar into execution and distribution. Tom Charman, co-founder, Block. First thing, I'd optimize for density, not scale. Week 1, reconnect with every strong relationship I have. Spend time physically in the highest energy rooms possible, Get extremely close to pain points again. Week 2 to 4: Find a market where speed of change is breaking existing workflows. Talk to operators obsessively. Build something embarrassingly narrow and useful. Month 2: Sell before polishing. Use services/collaboration/design partners to create cash flow. Create distribution immediately instead of waiting for product-market fit. Month 3: Narrow aggressively around whatever gets strongest pull. Hire the best people I need. Double down on anything creating asymmetric leverage. I also think people underestimate how important momentum psychology is. When rebuilding, protecting your own energy matters almost as much as strategy. CEO and founder. 4th vital. This is not really hypothetical for me. In 2023, I was suddenly paralyzed, placed in a medically induced coma, and on life support. I had to relearn how to stand and walk, and I am still rebuilding the strength and endurance to do both for normal periods of time. Saving my life consumed nearly everything my wife and I had. We are still rebuilding our lives from scratch, while I kept Fourth Vital alive. So I would do what I am already doing: protect the people I love, focus ruthlessly on what matters, try to keep moving— literally— rebuild one meaningful thing at a time, And never give up. You can lose almost everything without ever losing your purpose. Federico Sismondi, BRNDTS. I'd go after the same kind of opportunity we're pursuing now with BRNDTS. My first move would be conversations with investors—not necessarily the same ones from this project—but investors in the space presenting a clear value proposition. Then I'd immediately start talking to clients. I would not build anything or try to bootstrap until the money and client interest were aligned, which is exactly what we did at the start of BRNDTS. We didn't build something first to see if people liked it. We secured financial support and commercial interest first, and only then started building. Danny Cohen, Sticker.VC. I think I would try and relocate to a new geography, and then try and build a simple e-commerce online business and build on profits. Jiraj Svick, CEO and CMO, Trauma Trauma M. Spending 80 days headhunting the right people I want to work with, the remaining 10 days building an MVP. Derek, Instagram Marketing Secrets. I would post the best 30 YouTube videos I could to find the audience I needed to sell the service I was offering. In my case, Meta Ads videos, Duncan. I wouldn't rebuild but change direction, Megan Eskey, President, Reliquents. It took much longer than 90 days to get here, but since I have my copyrights and own 95% of my company, I am taking steps to ensure I won't lose everything. Paul Foley, Founder and Executive Chairman, Bulk exchange. I'd make ten phone calls before lunch. The tech stack, the platform, the venture—those can be rebuilt. What can't be manufactured quickly is trust, and I've spent thirty years building it across this industry on three continents. My network would be my first asset and my first call to action. Days one to thirty would be listening, getting back into rooms with the people who matter, understanding where the gaps are now. Days 30 to 60, framing a solution. Days 60 to 90, moving. The tools change. The relationships don't. That said, that scenario isn't on the horizon. We've got this. Paula Finbow. I've actually lived a version of this. When we lost over a third of our budget overnight to federal funding cuts, the sequence was: name the truth immediately and completely, to staff and community, but do it with hope over crisis and invite them to be part of the solution. Lead with the decision to protect what was working— our programs, our students, and our people— first. Let the community carry weight I couldn't carry alone. In 5 days we raised enough money to continue operating through the summer while we developed longer-term plans, not because I had a brilliant fundraising strategy, but because trust had already been built before the crisis, not during it. We survived because the community believed in us and what we were doing, and I don't believe trust is built in crisis, it's reveled there. So drawing with the values and integrity that show up in the small, unglamorous moments are how I would rebuild. PhD, Georgia, and Molly. Get a high-paying client that I would do work for while rebuilding. Then start with the brand and a problem/need to solve. Or if I already know the problem, then I would get an investor. Love building businesses and have the right network for it. Emmanuel Gersowitz, partner, MessageLab. First, believe completely in the possibility of rebuilding—not just recovering what was lost, but building something better. Then get very clear on direction. Ask my network for help. Tell people exactly what I'm looking for and what I can offer, and then run. I'm a big believer in movement. You don't rebuild by sitting alone perfecting the plan. You rebuild by getting into the world, talking to people, testing things, getting rejected, adjusting, and moving again. Dayaday.se. I have a process for this. Get drunk, go hiking up north, start making calls on the train back home. Vinometallia. Vinometallia.com. Keep going door to door. Dr. Noga Gulst. I'm not sure. I guess I will shift to a totally different area and business, as it's boring to do the same thing twice. Chris Heilman, VP Developer Relations, We Are Developers. I don't set arbitrary goals like 90 days. Instead, I would concentrate on my strengths, get a job to cover basic needs, and use the time to analyze why things went wrong. I've always been a big supporter of postmortems. We need to learn why things went wrong, so we don't repeat them. Nina Horowitz, immunebridge.com. If my personal life, as long as my husband and family and pets are okay, we can be anywhere. I don't need money or our house. In the business, first and most important is your team. Try to gather amazing scientists around me and see what ideas we've been chewing on recently. Everything else will follow if your core value proposition is important and built on solid science. Senior Partner, Validation and Compliance Institute. Start contacting my network personally and tell them I'm open for work, not social media. Get a low-interest loan, find a decent place to live, find a job with commission and/or profit sharing at a stable company within the revenue stream, marketing and/or sales. Fix what's broken, kill what can't be fixed, scale what's working. Founder, Lucid Pattern. I have lost everything and I am in the process of rebuilding. 90 days is not realistic because self-discovery was necessary for me to get to this point. I am not the same person I was in April 2025 that I am this April. I wouldn't rebuild my wealth and company in 90 days. I have military pensions, disability, my wife has 2 pensions. We currently live comfortably and still spend less than we take in. So I would take that 90 days reflecting on whether I want to found another company, tack away from starting another company and play music full-time, or build enough wealth and investment to take back the company I lost. Real estate developer. Founder, IND Consulting. Co-founder, Elevate SWFL and Elevate St. Pete. IND Consulting, also Elevate SWFL, Elevate St. Pete. I'd start with relationships, not a business plan. I'd make a list of the smartest people I know, call them, tell them exactly what happened and ask what problems they were seeing that someone like me could solve. Then I'd sell a service before I built anything— no logo, no website, no months spent planning. Solve an expensive problem. Generate cash flow. Listen closely to what the market keeps asking for. Then build from there. Chief Executive Officer, Sovereign. I would try to find some short-term employment just to get some money coming in to pay for housing, food, and the essentials. I would then start to formulate a business plan, and then I would go to friends and family to help financially fund the business and perhaps even become partners in the business. Co-founder and CEO, Mithril. I'd find the most boring product category at Costco, then make it stand out through design that represents narcissism and virtue. Sell with premium. I would take 2/3 of the time to go and travel somewhere new. Then I would write a book about that experience and see what comes from that. Do what I love. Do it strategically and with great focus. Eliminate distractions. Eat well. Sleep well. Work smart. Go at it with all the energy you have for 90 days. Focused energy is a powerful thing when propelled by a passionate quest. I experienced this firsthand in 2024. A group of us came together in 2023 with the goal of building a new streaming television network, and we formally established the company in 2024. Just months later, our technology lead made changes that rendered our minimum viable product unrecoverable. The platform had to be abandoned. Over the following months, every one of my business partners left the company, including 3 who resigned together unexpectedly. Less than 12 hours after the final departures, several trusted colleagues I had worked with in other capacities contacted me and proposed forming a new leadership team. We dissolved the original company, founded a new one, and rebuilt both the technology and the business from the ground up. Although the experience was difficult, it provided valuable lessons. We entered the second venture with a much clearer understanding of the technical architecture, governance, partnership structure, and operational decisions that would better support long-term success. Eric Molka, co-founder and managing partner, Strategic Brand Investments. If I lost everything yesterday, I would move to a country where life is very affordable and where I could enjoy my favorite simple pleasures daily, including high-quality ingredients, beautiful weather, swim in pristine sea or ocean, low stress, A community with strong values. To support myself, I would leverage my expertise to serve my community as a small business owner. Amber Meixle, founder, host, The Heart Leader Podcast, Suivera. Week 1: Get regulated. Reconnect with people I love. Accept reality quickly. Weeks 2-4: Serve immediately. Coach, speak. Create value with zero need for return, build trust. Month two, gather community. Listen deeply. Identify recurring pain points. Month three, build only what people repeatedly ask for. I trust relationships, adaptability, and service more than assets. You can lose a business, but you can't lose who you became while building it. Tomas Milar, founder, ekvista/startupperalsocheckly.com. I would borrow a fifty thousand dollars. outsourced everything and build super cool brand. Charge $350 per hour and spend a ton on marketing. Looch? I don't believe in rebuilding in 90 days. It takes time. CEO, also CFO of the Black British Initiative, Megasudo. I would run the exact 90-day foundation we implement for our pinnacle portfolio companies. Weeks 1 to 4 are purely about establishing a readiness score and building rigorous risk dashboards and financial models. Weeks five to eight involve aggressive pricing model refinement and scenario planning. Finally, weeks nine to twelve are dedicated to an intensive, data-driven outreach sprint and CFO-led negotiation preparation. Structure fuels scale, and discipline dictates results. Emmanuel Pastreich, President, the Asia Institute. I do not possess much as it is, but if I found myself homeless, I think the challenge would be to understand that there was a hidden meaning in what I experienced. and to find out what I was learning from the experience. I am inspired here most by Pema Chödrön's book Things Fall Apart and Steven Jenkins' Die Wise. PhD, founder and chief executive officer, Ringer Sciences. Days 1 to 10, I would call 30 executives I trust and ask what painful, expensive problem they would pay to make disappear tomorrow. I've built that trusted network over my career, and they are a great sounding board for what is next. Days 10 to 30, I would pick one where I had a mental image of how to solve it and sell the solution before I built it fully. Days 30 to 60, I would use my coding agents and little to no team to solve it, even embarrassingly manually if necessary. Days 60 to 90, I would sell it 3 more times and only productize the pieces that kept repeating. I live by a rule of 3. Something only becomes a tool or product if I have the same exact ask from 3 different people/companies. I would not raise money. I would not spend three months building software, and I definitely would not start with a logo. True story: my first logo took me longer than my first model, and built it in PowerPoint. Ola Yekini, PhD, CEO, EasyPly. If I lost everything tomorrow, I'd spend the first ninety days doing three things: secure income, rebuild my network, create value publicly every single day. When I moved to the U.S., I learned that starting over isn't about pride; it's about momentum. I'd take any honest work to create stability, reconnect with people, and consistently share what I know about product, hiring, and building. Skills compound. Relationships compound. Reputation compounds. Money can disappear. Those 3 assets are much harder to lose. I've rebuilt before. I'd do it again, faster. A computer, 2 large-screen monitors, a comfortable desk, chair, and bed, and a high-speed internet connection. I'd be back up before Thursday. I'd become a miner on specific blockchains, or build on a new blockchain with substantial funding and token grants. I probably wouldn't think of it as rebuilding. I'd see it as an opportunity for radical change. I wouldn't necessarily want to rebuild what I had just lost. Rosalind. I think second time around, I can rebuild much faster than I built the first time. For a platform business like mine, I would spend the first 30 days building out the supply side while at the same time working on the platform itself. In day 30-60, I would go back to my best past clients and ask for referrals, manually make the matches with the supply side, proving our model still works. In day 60, 90, I would work on the growth channels, marketing, advertising, and contents. Also rebuild the relationships with partners that can refer clients to my business. Founder plus CEO, consequentlycreative.com. First, I would focus on finding customers by solving problems for people. Then out of that, I would try to find a niche and get more and more focused in my message so I can stand out. Finally, I would try to refine that message and be edgy in a way that would get people motivated around what I believe in. Oh, then I'd start a company. Eva Scalzo, Eva Scalzo Advising. If I lost everything tomorrow, I would use my past client base of 18 years to source out referrals and start from the ground up. Noah Shoman, Silo Digital. One proper planning session plus Claude Code Sergei Serukov and Tinko and Tinko dot com. Getting customers is the hardest part. I would go to people I know and who knows me and give them the best deal I can make. Siggy Overtune: I lose everything daily and gain it back. I am used to the roller coaster. Ashish Singru: I am assuming I would not lose my mind and heart here. First of all, keep my family and trusted friends close and even tighter. They are the wind beneath your wings. Then I would rebuild from scratch by using influence to reconnect with my network and build new networks. Find those who I can help or make the difference to, and find the reciprocal opportunities as well. While 90 days will not get me back to where I was, this approach will create the paths to get back over time faster. Jack Swift. I would start with relationships. I would reach out to the people I trust and the people who trust me. I would listen for where there is pain, confusion, change, or opportunity. Then I would bet on the superpowers that give me energy and aliveness. Helping leaders create clarity, make sense of change, navigate uncertainty, and reconnect with their own power. I would not try to rebuild everything. I would rebuild from the most alive signal. I would find someone I respect and offer to work for and learn from them. At the same time, I'd write online about my biggest ideas and work to turn at least one of them into a real service or product to sell. And make money through multiple jobs plus projects until one pays the bills by itself, Then expand. Jay Tokash, founder and CEO, Note Effect. I don't think about this much, but I have been asked it a lot, and this is how I have come to understand it. First, I would not panic. I've already built from nothing multiple times. Days one, seven. I'd call every strong relationship I've built over 25 years—customers, operators, channel partners, founders, event leaders. Enterprise contacts. Most people underestimate how much leverage comes from reputation and your network. Days 8-30, I would identify a painful enterprise workflow problem where buyers already spend money and where I could close revenue fast. Then pre-sell as much as possible and then build it. Days 31-60, I'd create a wedge product tied directly to ROI, probably around sales intelligence, enterprise knowledge capture, Or training retention because those problems are massive and measurable, and right now this is what I know best. Days 61, 90. I'd hire very carefully, stay lean, and focus on distribution over perfection. Most founders overbuild and underdistribute. I would also avoid almost every distraction disguised as an opportunity. Arvin Vora, Vora Method. I've had to rebuild my business many times. For example, when colleges went test optional, my SAT business evaporated overnight. My SAT classes are the hardest on earth, and no student is going to take a class that hard if the SAT isn't required. And no parent is going to pay for a class that is 10 times as expensive as the average class if it's not required. At the time, my business was 99% SAT. Here's what I would do. First, I'd see where the inflexible, high, unserviced, under-addressed demand was. I would choose the areas— 1 to 5 areas— that I would target. Then, here's the rough part. I'd see who on my staff was exceptionally fit for the new direction. Chances are, it would be either a tiny minority or nobody. I'd keep them, and everyone else would be immediately laid off. No point in prolonging the unpleasant work that needs to be done. From there, I'd make sure the differentiation was clear, run some test marketing, run full marketing, and take it from there. Brian Wally. 1. Reduce all spend to essentials. Only 2. Understand what my lending/support/survival options are. 3. Secure a role that can pay me, even if I have grow into the income. 4. Prioritize and execute. Jeffrey Weiss. Day 1. Inventory relationships, not assets. 25 years in this industry means the network is the real balance sheet. Week 1: Get in front of the 10 people who'd hire me or fund me by tomorrow and ask directly. Weeks 2 to 4: Pick one skill I can monetize immediately— coaching, consulting, speaking— and start selling before the offer is perfect. Month 2 to 3: Rebuild systems, not hustle. I've built 250+ facilities from scratch. The pattern is always the same: sell first, build the machine second. Founding partner, Awake Partners. I'd go back to basics with 100% sweat equity. Days 1 to 30, call everyone in my network to audit their immediate problems and do pure high-ticket matchmaking/B2B introductions. Days 31 to 90, approach startups and offer performance-based LinkedIn outbound prospecting. Zero starting cost, pure immediate value. Question 5: What do most high performers secretly suffer from, but no one talks about? Fear or doubt shows up in 19 of 64 answers; loneliness and isolation in 9; anxiety, no sleep and burnout in 8. The doubt doesn't go away when you succeed; it just gets better dressed. —Paul Foley, Paul Piquet, Loomis. Most high performers don't slow down. The slow feels uncomfortable, so it's usually avoided. But there is a lot to learn in the slowdown. Fast signs 174. Owner, fast signs 174. Life is short. If you're suffering, then change. For any faults, this country gives you incredible autonomy to make changes. Sometimes high performers end up wearing golden handcuffs, but it's hardly insufferable. Stephanie Beach, founder/CEO and podcast host, The Marketeer Group. Imposter syndrome, for sure. their brains also don't shut off. Even when they relax, they are always thinking, analyzing, going. President, Beeline Legal. Male pattern baldness. High performers quietly lose the ability to appreciate progress. Every achievement quickly becomes the new baseline. You launch a product, get promoted, close a funding round— it feels great for a few days, and then you're already thinking about the next challenge. The market doesn't help either. Sometimes extraordinary performance is simply the price of staying competitive, so your definition of good enough keeps moving. That's fantastic for growth, but terrible for happiness. If you're not careful, you stop seeing how far you've come and only notice the gap to where you want to be. Matt Blumberg, CEO, Markup AI. Imposter syndrome, believe it or not, The higher the performer, the greater the imposter syndrome. That's an intrinsic part of drive. Bora, reacherapp.com. I think loneliness, exhaustion, burnout, and not being understood. Nitin Khanna, CFA, President, N3 Business Advisors Inc. The belief that everything depends on them. It creates isolation, guilt when resting, and an inability to delegate. In business, We call it owner dependence. Personally, it can become identity dependence. Co-founder, Block. A weird combination of hyperbelief and low-level paranoia. The people who build difficult things usually have an unusually strong ability to imagine outsized futures, but that same mechanism also makes you very aware of fragility. So externally you can look very confident while internally running simulations of every possible failure mode simultaneously. I also think a lot of founders become emotionally detached without realizing it. You spend so long operating in survival mode— high stress, constant abstraction— that normal life starts feeling strangely distant. CEO and founder, Fourth Vital. Loneliness, particularly the loneliness of carrying uncertainty while everyone around you depends on your confidence. High performers may be surrounded by people, yet have very few places where they can honestly admit fear, exhaustion, or self-doubt. BRN DTS. You have to dial down your expectations and your eagerness to get results fast, because being a high performer isn't the only thing that moves a business forward. Other people bring talents and virtues that matter too, and you can't overwhelm them with your own pace. So one of the main pains is coexisting with people who aren't high performers. There's another one in business development specifically. Your pace collides with the pace of decision-making inside other businesses. You're selling into a process that can't be avoided or accelerated, and it's painful watching that process run slow by nature, unable to change the other side's structure. You have to learn to respect that pace. Danny Cohen, sticker.vc. I'm quite confident it is the imposter syndrome. I know many people that feel that. It of course takes on different versions, but that is the core. Craig Coolmit. I believe high performers deal with self-doubt more than people realize and suffer from that by not asking for help/insight from others more than they do. It's analogous to Dunning-Kruger effect, where the less qualified have great confidence in how much they know and highly intelligent people are intimidated/aware of how much they don't. Jiraj Sivik, CEO and CMO. Trauma, Trauma TM. Judging others by my own standards, expecting way more than some people can actually deliver. Derek, Instagram marketing secrets. Being able to work all day and then be effectively be able to turn off. Many entrepreneurs are diagnosed with ADHD and are obsessive about what they're doing. It's not uncommon for business owners to have struggled or be currently struggling with substance use to help them work better or take time off better. There always is another level above Megan Eskey. Relevance. High performers are never satisfied with their own performance. I have had experiences where others took aspects of my work forward without including me, but that was largely irrelevant because they were working with an unformed idea that I would have ultimately rejected in favor of a more refined model. I am sure that I will look back on this phase of my company building as being surprisingly naïve. Paul Foley, founder and executive chairman, Bulk Exchange. The gap between how certain they look and how uncertain they feel. Every high performer I've ever known, and I include myself, carries a private version of the story that looks nothing like the public one. The doubt doesn't go away when you succeed; it just gets better dressed. Freddie Mercury had his own version of a wonderful song, The Great Pretender. Being an entrepreneur can be like that. The highs are very high, the lows are very low. You have to push through it all and look solid, composed, and confident to the outside. Founding partner, Reflect Ventures. Imposter syndrome? How the heck did I get here? A nervous system stuck in scarcity, even when things are objectively going fine. I know that feeling. Waking up at 2 AM, running numbers, and so on. High performers get very good at operating from that state and calling it drive. But leading from a dysregulated nervous system and leading from abundance produce completely different organizations, even with the same talent and the same resources. Petra Ferm, PhD, Georgia, and Molly. Some sort of stomach/digestive issues. Emmanuel Gerzowitz, partner, Message Lab. Imposter syndrome. The strange thing about high performers is that the more they know, the more aware they often become of everything they don't know. You can have the degrees, the experience, and the track record, and still occasionally wonder how everyone else seems to have received an instruction manual you somehow missed. Jennifer Grunkvist, diadaya.se. Trauma. Enrico Guglielmi, Vina Metallia, vinametallia.com. Low Margins, Dr. Noga Gulst. Being over-optimizing. Many successful entrepreneurs experience imposter syndrome. Chris Heilman, VP Developer Relations, We Are Developers. Loneliness. If you are a big success, you get a lot of admiration, but you also get a lot of animosity that is not always communicated. Finding real friends and people you can rely on when you're riding high is a tough task, as you also need to make time to care for them whilst trying to be the best. Nina Horowitz, immunebridge.com. Constant spam calls, spam LinkedIn messages, spam emails, but needing to look at all of it because the rare one is actually important and you care so much that you don't want to miss that one. Being the public face of a company is great and terrible at the same time. Norm Howe, Senior Partner, Validation and Compliance Institute. Hubris. Not sure no one talks about it, though. Burnout/mental health. I am going to answer this from an IO psychology perspective instead of my own take: a fear of falling behind. Diminished mental health, especially manic behavior. Candle, real estate developer, founder, I+D Consulting. Co-founder, Elevate SWFL and Elevate St. Pete. I+D Consulting, also Elevate SWFL, The inability to ever feel like they've done enough. You hit the goal and almost immediately move the finish line. What once felt impossible becomes normal incredibly fast. That drive can build an amazing life, but if you aren't careful, you can become very successful and still constantly feel behind. Chief Executive Officer, Sovryn. I am not sure I am one, but being ahead of the curve and waiting for society to catch up has been extremely difficult for me. And many others I talk to. David T. Kim, cofounder and CEO, Mithril. They confuse being useful with being loved. Many high performers try to become so impressive that no one can abandon them. Fear of others discovering their lack of self-confidence. It is sometimes talked about and rarely admitted publicly. Imposter syndrome. Especially in entrepreneurs. Self-doubt is the ultimate sabotage to success. This is amplified when inferior performers work to drag a high performer down to their level. High performers must strive to be highly self-aware and rise above the doubters, especially when the top doubter is themselves. Loneliness. One of the challenges I encounter is that I often think at a different strategic level than many of my peers. I naturally move between long-term vision and implementation details, which can make it difficult for others to see how I intend to execute a complex project or business venture. In the early stages of an initiative, people sometimes question whether my plans are realistic, particularly when they involve large-scale technology or ambitious business models. The path is often obvious to me but not yet visible to others. Once they watch me execute successfully a few times, trust tends to develop, and future projects face less skepticism. The most difficult part is often the period before there is tangible evidence. During that phase, I've learned to spend less energy trying to convince skeptics and more time engaging with people who naturally think in systems, strategy, and execution. Those conversations are more productive because they begin from a shared way of evaluating complex problems rather than from disbelief that the outcome is possible. Eric Malka, co-founder and managing partner, Strategic Brand Investments. A chip on their shoulders. The true driving force of overachievers is having early-life hardship that makes you want to prove the world wrong about you. Amber Meixle, founder, host, The Heart Leader Podcast, Suivera. I would offer it's the fear that love and admiration will disappear if they stop producing. Many high performers are carrying a hidden belief: if I slow down, I become less valuable. That creates cycles of achievement followed by a deep emptiness. The answer isn't lowering ambition or slowing down. It's separating worth from output or achievement. Tomas Milar, founder, ekvista/startupr also checkly.com. Having big dreams, it's painful. You go through loads of lows, mostly lows, and it takes years before you get off the ground and get happy again. It's the happiness. Everybody talks about easy stuff, but I see daily how companies are running out of money. Or companies get sold for $100 million, founder walk away with $2 million before taxation, but nobody talks about that he ate ramen for past 10 years. So $2 million slash 10y equals $200,000 minus $100,000 after taxation. It's not a win, right? Michelle Miara Luch. They want revenge in the form of success and recognition. They suffer because they're invisible. Gabriel Osamor, CEO, also CFO of the Black British initiative, Megasuto. They suffer from the growth paradox. High-performing founders often scale their revenue to the moon, but because their underlying financial infrastructure is weak, their operational costs eat their cash reserves before the money even hits the bank. They are exhausted because they treat financial reporting as a luxury for later rather than the core navigation system they need today. President, The Asia Institute. I am not a CEO worshiper to start with, and many who are presented to us as high performers are but expert at manipulating perceptions. So I would say that deep insecurity often underlies the drive for visible success, and we should be aware of this reality. An unsurprising amount of high performance is socially rewarded anxiety, We call it drive, standards, obsession, work ethic. Sometimes it is those things, but sometimes you are extraordinarily productive because your brain refuses to believe anything you have done is enough, and you are afraid of being called out on the thing that is not quite enough in your view. The dangerous part is that the world keeps rewarding you for it, so you have very little incentive to ask whether it is actually healthy. It isn't Ola Yekini. PhD, CEO, Easyply. Most high performers secretly suffer from the pressure of always having to look like they're doing well. Behind promotions, successful launches, and career milestones are moments of self-doubt, rejection, burnout, and uncertainty that rarely make it to LinkedIn. Director, Civic Works. Isolation. Co-founder, LeadPoet. Nothing feels like enough for very long. You hit something you obsessed over for months, feel good for a day, then immediately move the goalpost. NomadLife.TV. Imposter syndrome? Maybe. And probably a constant need to differentiate themselves from the pack. Imposter syndrome? Mark Rust, Founder+ CEO, ConsequentlyCreative.com. I think everybody suffers from the same thing. wondering what other people really think. Eva Scalzo, Eva Scalzo Advising. Most high performers suffer from anxiety and sleeplessness. Our brains never turn off, but none of us talk about it. Silo Digital. Mental health issues/anxiety/not being liked socially. And tinkoandtinko.com. High performance? Hmm. Perhaps that they are not high enough, or moving too slow. Siggy, overtune? No idea. I am not a high performer, Ashish Singru. From personal experience, high performers overemphasize how much their credibility comes from the org chart and the logo that employs them. Step outside it in multiple ways. When you speak at industry forums, it is your step towards opening your mouth and building your personal brand and credibility. Write chapters in an industry book or publish an article or do a podcast. Be inspired and also humbled by how your brand can travel further and stand for itself out in the open and for scrutiny. As a final step, try stepping out of the logo's comfortable shade and set up something on your own to influence clients who need you unvarnished expertise. Often high performers hold back and do not travel this journey because of the umbilical cords of the logo and org charts makes it difficult. Jack Swift. Deep insecurity? A lot of high performers are driven by a quiet belief that they are not enough. Not successful enough, not smart enough, not safe enough, not worthy enough. The outside looks like ambition, discipline, and excellence. But underneath, many are still trying to prove something to themselves, their parents, their peers, or the world. It's lonely being a high performer, where most of your life is high energy at work, then family takes most of the rest of your capacity. Finding extra time and energy for socializing, and especially doing the work to find and cultivate interesting friends, is so important but tough to do. Jay Tokosch, founder and CEO, Note Effect. I have a hard time turning off my mind, my ambition, drive. People think high performers are addicted to success. I think we are actually addicted to responsibility and never want to fail. Your brain gets conditioned to feel like if you stop pushing, Everything slows down. So even when things are going well, your mind stays in threat detection mode. The dangerous part is that society rewards it right up until it burns you out. Vora Method. I think the vast majority of high performers measure their own value by what they can do or how much they achieve. I think that leads to a toxic self-image that limits individual greatness. I think most high performers should remember that each human has infinite worth and let that sense shape the quality of what you do. The loneliness. The LinkedIn crowd would tell me to cry in a bucket of my own tears while other high performers would make eye contact, agree, and then get back to being a high performer. They don't know how to stop performing, even alone. I coach people who can command a room but can't sit in silence without reaching for a phone or a task. High performance becomes an identity and then rest starts to feel like falling behind. Fear that they've already had their last win. It's all downhill from here. The distortion of time. It's not just about having a heavy workload; it's the mental frustration of feeling like days last only 2 hours. High performers secretly suffer from the anxiety of not being able to be everywhere at once— a great CEO, a present partner, A good friend and healthy. Question six: What's the most dangerous advice in your industry that people blindly follow? AI comes up in 14 of the 64. The other big theme is money, raising it too early, raising too much, and cutting brand spend when things get tight. Paul P.K. Loomy. I've yet to be offered any canny advice, safe, dangerous, or otherwise. Fastens 174. FastSins174. Use AI to vet your customers. When a customer reaches out via online, phone, or email, that's money reaching out to you. You don't want the opportunity to talk to it. You want to make sure it's worth your time. They are reaching out to buy. That should be worth your time or your staff's time. Founder/CEO and podcast host, The Marketeer Group. When clients kill top-of-funnel/branding ads during a downturn and instead double down on direct response, Clients think money spent on brand awareness is a luxury. In tough economic times, they wind up putting 100% of the budget into direct-response ads to yield immediate cash. This treats marketing like a light switch instead of a momentum wheel. The reality? Cutting brand spend during a slowdown makes your performance ads drastically less effective. When people don't recognize your brand, your CTR plummets, your costs skyrocket, and your conversion rates crater. All around no good. Michele Berdini's president, Beeline Legal. In every industry, use AI for everything or you will be left behind. Dario Blanco. The most dangerous advice is that every growth problem should be solved by hiring more people. We're still conditioned to equate bigger organizations with better leadership. Executives are often rewarded for managing larger teams, so hiring becomes the default answer. As leaders, our first responsibility isn't to grow the organization; it's to make it more effective. Every hire adds communication paths, complexity, and a responsibility to create an environment where that person can succeed. That's why I've always believed hiring should be the last optimization, not the first. Before adding people, I'd ask, can we simplify the product, automate the work, improve the process, or eliminate the problem? The goal isn't to build the biggest organization; it's to build the one with the highest impact per person. AI hasn't changed that principle; it has simply made it much easier to put into practice. Matt Blumberg, CEO, Markup AI. Move fast and break things, applied to AI. When every employee can generate content with AI and you have no governance layer, you're not moving fast. You're creating legal liability, brand damage, and compliance risk at machine speed. The companies that win in AI won't be the fastest. They'll be the fastest who don't blow themselves up. Bora, ReachYourApp.com. Build as many things as possible and don't focus. Nitin Khanna, CFA, President, N3 Business Advisors Inc. Grow revenue at all costs. In construction, more revenue can destroy value when margins, cash flow, controls, leadership, and risk management do not scale with it. A bigger company is not automatically a better company. Tom Charman, co-founder, Block. Just talk to users. Obviously, customer conversations matter, but humans are notoriously bad at explaining their own behavior retrospectively, especially in product. What people say they do and what they actually do are often completely different things. The dangerous part is when teams mistake articulated opinion for ground Behavioral data is usually far more valuable than self-reported certainty. CEO and founder, Fourth Vital. It's always been done this way. Don't rock the boat. It is an old adage that never seems to die, and it is dangerous because struggle is at the heart of innovation. People tend to shy away from struggle instead of running toward it. But the future is built by those willing to confront a problem at its deepest level and find a path forward that no one else has seen. Without rocking the boat and without struggle, there is no real innovation. Federico Sismondi, BRNDTS. That you can't introduce new things because people take too long to trust them, so play it safe. The problem is, everyone ends up doing the same thing. Advertising has always changed when a new medium created an opportunity, like when magazines started printing in color. The truth is, advertising needs to change because the old way of engaging people stops working. If you don't find new ways to connect, you exhaust people's patience with your brand. The companies that find new ways to connect are the ones that make a brand or product a market leader. Playing safe and refusing to introduce new ways of communicating is the most dangerous advice people follow. Danny Cohen, Sticker.VC. Take the most money at the highest valuation. People see fundraising as a goal, not the means to a goal. Blindly following conventional wisdom, or not looking outside the flavor of the day I may be talking to you, AI, later in investing cycles. This played out in my Wall Street act too, and I see it in speaking with venture investors now. Any advice that is blindly followed. Trust your attorney blindly. Quite a lot of people have developed trust towards their attorney, regardless of their specialization, and they come to them with all their legal needs. So it's not uncommon for attorneys who settled a divorce or work on company mergers to also attempt to handle intellectual property protection. More common in Europe, but present everywhere. Instagram marketing secrets. You should use AI to write, design, or manage your paid advertising. That the other guy knows what he/she is doing. President, Relequents. Don't do anything that jumps out of the box. Stick to incremental improvements of current technology if you want to be successful in your field. The obvious outcome is that entire fields of study, such as space robotics, are overlooked. Paul Foley, Founder and Executive Chairman, Bulk Exchange. In construction, that's how we've always done it. It's not said as advice, it's said as a full stop. And in an industry worth trillions that still runs procurement on gut feel and phone calls, It's cost everyone—buyers, suppliers, owners—billions in inefficiency they've never even tried to measure. The most dangerous ideas aren't the ones people argue with; they're the ones nobody questions because they've calcified into assumption. Michelle Friedman, founding partner, Reflect Ventures. Pretty much all of it. VC investors tend to be herd animals. If you lead the trend, you do well. But if you follow the trend you are going in when everyone is starting me too companies. Valuations are up, and getting into the small percentage of decent deals because of all the me too's is hard because the VCs with a reputation in the space crowd you out. Paula Finbow, move fast and break things. In youth and human-serving work, the things that get broken are trust and people. I'd rather move with purpose and build things that last. I believe the process is the product. The process of listening, co-creating, the trust building isn't the overhead before the real work. It is the real work. Skip it and you're just moving fast towards something that won't hold. Emmanuel Gersowitz, partner, MessageLab. That buzz equals success. It doesn't. You can generate enormous visibility without creating trust, meaning, reputation, or lasting value. Also, I have to confess, buzz may be one of my least favorite words in the English language. Jennifer Grenquist, The pitch deck. Vinum Italia, vinumitalia.com. Keep it classic, Dr. Noga Ghulst. Just move on. Things have the tendency to succeed. VP Developer Relations, We Are Developers. Fake it till you make it. People keep overselling themselves and trying to impress others. The issue with this is that you also constantly lie to yourself when you do it. Over time, you will feel like you are competing against yourself and losing. This is much like people who go all in on dazzling the world with a fancy Instagram profile, only to realize their real life is bland and boring, and most of their energy goes into keeping up appearances. Nina Horowitz, immunebridge.com. You have to do it the way everyone else did it; otherwise, it won't work. Norm Howe, Senior Partner, Validation and Compliance Institute. Getting certifications? They stack certifications behind their name. When a problem comes up, they frantically stumble around through their certs to find one that they can plaster onto a problem. Does it solve the root cause? Who cares? The problem is covered up. That hyperscalers have a clue about the future of AI. Romella Janine, founder, Lucid Pattern. If the data shows it, then it must be true. Results must always be vetted with stakeholders. Ideally, an informed analyst is the one doing the work and knows what the data means because they know the underlying business processes. Initially giving your product away for free or at significantly reduced cost to create an initial user base. You have to assign value to your product even if you provide discounts to first adopters, but you gotta price at scale if you want to truly measure product-market fit. Real estate developer, founder, IND Consulting. Co-founder, Elevate SWFL and Elevate St. Pete. IND Consulting, also Elevate SWFL, Elevate St. Pete. If you build it, they will come. No, they won't. A good real estate development isn't just a building. You have to understand who you're building for, what they actually need, how the place operates, and what makes people choose to come back. The real estate is only part of the business. Brandon Karpelis, Chief Executive Officer, Sovereign. That by fixing the money, that is adopting a Bitcoin standard, we will fix the world. I do believe that having hard money will solve a lot of the current society's ills, but I also see the possibility of a centralized power structure that emerges from a small cohort of people controlling the majority of the world's wealth. Ironically, that is the current system we are living under right now and has ushered in so many untold horrors. The idea that the new group of Bitcoin oligarchs will somehow be benevolent is something that more Bitcoiners need to think about. David T. Kim, co-founder and CEO, Mithril. Injecting yourself as the main character, confusing self-importance with passion. Most modern writers suck because they never experienced life. B. Kim. Don't take big risks. Brad Lamden. Hiring and promoting based on antiquated, unreliable resumes and gut feelings. In this new age of AI, companies need to focus on getting the right faces in the few remaining correct places. This is a vast subject. Currently, it is to integrate AI into production workflows. A lot of businesses doing this are having poor, if not disastrous, results, only some of which are made public. I have friends at the C-level across industries, so I hear their AI implementation horror In entertainment, the worst advice is to keep doing business as usual. The entertainment industry has forever changed, and businesses approaching it in new ways are the ones that will survive and thrive. I will dominate the genre of conscious media in short order because no one else is thinking the way I am—that live TV will become increasingly important when broadcasting people, subject matter experts, podcasts, practitioners versus actors in scripted series. Erik Malka, co-founder and managing partner, Strategic Brand Investments. ScaleFast, Amber Meixel, founder. Host, The Heart Leader Podcast, Suivera. Find certainty. I think certainty is massively overrated. Certainty closes us to curiosity, and curiosity is the very thing that opens our access to possibility. The strongest leaders I know aren't the most certain. Instead, they create a safe space for people to question, Explore and challenge ideas and existing models while also creating awareness that structure is necessary for forward movement. Tomas Milar, founder, Ekvista/Startupr, also Checkly.com. I've spent most of my 20s in Asia/Hong Kong, so it was mostly to follow certain social status. Nobody really say that, but everybody expects that you need to look good. Short, yeah, it's cool, but there is loads of distraction with it. Not just that you spend money, Michelle Miara, Luch. Anything from so-called investors. Listen to yourself. Gabriel Osamor, CEO, also CFO of the Black British Initiative, Migasuto. The placeholder trap. This is the incredibly dangerous advice telling founders to loosely estimate or make up figures to secure an investor meeting with the intention of fixing the numbers later. When you hit due diligence, investors are not just checking your maths; they are checking your integrity. If your deck does not match your management accounts, you destroy your credibility, and trust is the one asset you cannot buy back. Emmanuel Pastryk, President, the Asia Institute. My industry is either academics or politics. Let me answer both. In academics, the bad advice is that you should write papers for academic journals and avoid engagement with ordinary citizens. That thinking has led to a declining support for education. In politics, the bad advice is that you should raise money to pay for campaigns. Politics is about changing perceptions and advocating for new visions. That often is not about elections. Most elected officials are incapable of changing anything. Yash Gad, PhD, founder and chief executive officer, Ringer Sciences. AI won't replace you. Someone using AI will, so just start using AI. I think that is comforting nonsense. In plenty of cases, Nobody replaces you. The workflow disappears, or the team gets smaller, or the company realizes it does not need 9 handoffs and 3 management layers anymore. The more useful question is, if we invented this company today with AI already available, would my job exist in its current form? I don't think a lot of senior folks want to go down that mental exercise because it scares the heck out of them. Ola Yekini, PhD, CEO, Easyply. Raise funding as soon as you can. Capital doesn't fix a broken business model. Too many founders chase investors before they've proven customers will consistently pay for what they're building. Funding can amplify growth, but it can also amplify mistakes. Director, Civic Works. Step carefully. Co-founder, LeadPoet. Just automate outbound. If your targeting is bad, automation only helps you interrupt more people faster. AI should make outreach more selective, not just increase volume. Jason Rhodey, NomadLife.tv. That money should be the primary measure of success. Discipline yourself to do what you love, do it authentically, and the right things for you will follow. Rosalind. In our industry, I think there are a lot of puffery. Some agencies puff up the resume of their care providers to make them seem more attractive, thinking that customers cannot tell. But I think customers can tell the real from the inauthentic, and in the end, lies do come back and haunt you. Mark Rust, founder plus CEO, consequentlycreative.com. The most dangerous advice that people follow blindly is the get-rich-quick schemes found in those emails promising hundreds of clients and leads. There is no such thing as easy in life. Hard work is always required. Eva Scalzo, Eva Scalzo Advising. Anything social media spits out is the most dangerous advice that people in my industry follow. My advice is do your due diligence. Noah Shoman, Silo Digital. Do social media with AI. Sergey Surukhov, ntinko ntinko dot com. Right now, build AI agents. Siggy Overtune. Follow the money, Ashish Singru. Setting big, hairy, audacious goal. Big, hairy, audacious goals. Often I see the vanity of big, hairy, audacious goal causing great deal of dissatisfaction and waste of effort and resources. Because the commitment to big, hairy, audacious goal is not easy from the founder and everyone around them. I much prefer agile, iterative approach to focused and prioritized efforts that work on the most critical slices first and then move outwards. That you should be scared. Scared of authority, scared of change, scared of technology, scared of being wrong, scared of losing relevance. Fear-based leadership keeps people compliant, but it does not make them powerful. The leaders who will matter most in the next era are not the ones who avoid change; they are the ones who learn how to relate to change without giving away their center. Neil Thanedar. Raising more money when you can is always better is a major fallacy in startups. More money means fewer exit options, which puts too many startups into a zombie state where they're too big to shut down but too small to sell at a price that would make all their investors happy. Jay Tokosch, founder and CEO, Note Effect. Focus on raising money. Too many founders raise before they truly understand distribution, customer pain, or market timing. Capital can amplify a good business, but it can also hide bad assumptions for years. The second bad piece of advice is focus on one tiny niche forever. Don't get me wrong, you can do well just focused on a niche, But usually that ceiling only goes so high. I think to grow larger, the bigger companies eventually become infrastructure layers across industries, workflows, or ecosystems. Arvin Vora, Vora Method. It's hard to even know where to begin on this. American education is terrible despite high public and private expenditures, and that terribleness comes from a series of bad decisions. Those decisions are made by teachers, parents, and supplemental educational programs. The core of that idiocy comes from a failure to understand what education is. Education isn't measured by the amount of work you do, but by the amount of intelligence and skill you gain. Put another way, education isn't measured by what a student does, but rather by what a student can do. AI has highlighted the foolishness of measuring education by work rather than intelligence. AI lets students crank out work while building zero intelligence. I think it will force enough people to really think about the purpose of education and hopefully refocus it on building student intelligence rather than encouraging students to outsource busywork to computers. We've always done it this way and/or that's never been done before, Jeffrey Weiss. Just follow your passion. In broadcast, AV, and post-production, I've watched people chase passion projects straight into bankruptcy because they skip the boring stuff. Contracts, cash flow, margins. Passion doesn't pay vendors; competence does. Passion is the reward for competence, not a substitute for it. Elie Zamour, founding partner, Awake Partners. That you can fundraise alone—it's a death trap for founders. Fundraising is a full-time job that requires an army or expert backing. Doing it completely solo burns 80% of your operational time, causes you to neglect your product. And usually ends in failure and burnout. Question 7: What's one obsession or daily ritual you have that no one would expect? The best chapter in the book. Mornings and exercise dominate— walks, gyms, cold showers, stretching— but then there's a wall sit while brushing teeth, a robot vacuum twice a day, tarot on YouTube, and a fantasy board of directors made of AI. Paul Piquet, Loomi. Creative writing is something that helps me clear my mind. Often when I'm switching between different tasks and need to reset my brain, rather than look at Insta or stand in front of the fridge, I'll do some creative writing that's a palate cleanser. I'm guessing no one would have that one on Kalshe. Fast Signs 174. Owner: Fast Signs 174. I got to the gym every morning, which is quite a bit more than one would expect for a guy as fat as I am. But they practices for my mental health as much as anything. They number one piece of advice when you are depressed or lonely is to be active. So I want that habit in place before I need it. It's pretty hard to build when you're in a bad state. Stephanie Beach, founder/CEO and podcast host, The Marketeer Group. I work out almost every day. I literally plan it into my calendar to make sure I prioritize it daily. Michelle Berdini's president. I'm kind of an open book, and people who know me know that I'm weird, so there's very little that would surprise them. Here's one that's kind of weird: I do a wall sit while brushing my teeth. Both activities are astonishingly boring, so I combine them and cut down on the number of minutes each day when I have to be bored. I'm obsessed with protecting the builder mindset, and with never becoming too far removed from the product. As my career progressed, I deliberately resisted the idea that leadership meant moving further away from technology. I still prototype. I still experiment. I believe the best engineering leaders don't stop being builders; they simply build at a different level. Staying close to the product keeps my decisions grounded in reality instead of assumptions. Matt Blumberg, CEO, Markup AI. I built an AI fantasy board of directors: Steve Jobs, Warren Buffett, With custom prompts that adopt their decision-making frameworks and challenge me on real decisions. I run major strategy calls past them before my actual board sees them. It sounds ridiculous. It's changed actual outcomes. Reacherapp.com. Daily walk at 6 AM. CFA, President, N3 Business Advisors Inc. I regularly ask one question: Would this business still operate successfully if the owner disappeared for 90 days? It is simple, but it quickly exposes weak systems, unclear accountability, and hidden risk. Tom Charman, co-founder, Block. I spend an unhealthy amount of time studying systems that aren't startups: insurgencies, intelligence operations, crowd psychology, gambling behavior, propaganda, street culture, radicalization pipelines, urban movement patterns, A lot of human behavior repeats across completely different environments. Once you start noticing the patterns, product adoption and decision-making stop looking random. Also, probably walking. A huge amount of my thinking happens walking through cities late at night with voice notes. CEO and founder, Fourth Vital. Most people are surprised to learn that I am also a trained chef. I need to do something in the kitchen every day, however simple. I do some of my best thinking while cooking. When I am wrestling with a difficult problem or feeling stressed, the pull toward the kitchen is almost instinctive. If I do not cook, it feels as though I have interrupted the problem-solving process. Federico Sismondi, BRNDTS. I was born in Argentina, so my ritual is preparing mate before starting the day, the way you see soccer players show up to practice with their thermos and mate before training. I do it early in the morning and carry it through the day. Very likely I'm in a sales meeting, and whenever I get the chance, I take a drink from my mate. Danny Cohen, Sticker.VC. Most people know this by now. My love to Pearl Jam. It includes everything: posters on the wall, tattoo, and top 0.1% of listeners on Spotify. Craig Kulmit. I thank my wife every day for marrying me. Juraj Svick, CEO and CMO, Trauma Trauma TM. I have two daughters, three-year and two-year, and pretty much every other night at least one of them needs somebody to hold their hand in the middle of the night. So more often than not, I do sleep on a floor with an arm twisted to accommodate them. The best time to think things through. Derek, Instagram marketing secrets. I take about ten different supplements a day and enjoy doing jiu-jitsu a few times a week. Duncan, Peloton in the Am Meganeski, president, Relevance. I am a big fan of e-bikes and scooters. I live in an area with lots of beautiful rides. I am about 2 miles from the beach and a mile from the boat docks. I try to get out every day, even in the coldest weather. Founder and Executive Chairman, Bulk Exchange. I'm up before most people are thinking about their day. Not as a productivity hack, I just genuinely think better before the world gets loud. Some of my best decisions have been made before 6 AM with nobody around. Paula Finbow. I write three pages in my journal every single morning, not for productivity, not to plan the day, but to actually sit with what's on my mind, what I'm carrying, and what energy I want to bring into the room before I bring it there. It's the one place I get to be honest before I have to be composed. Most people would guess I start my day with a to-do list. I started by figuring out who I need to be and who I want to be that day. What I need or want to do. Partner, Message Lab. I have far too many obsessions and rituals to choose from, but one is reading the news across different countries, languages, and political perspectives. The same event can become an entirely different story depending on where and how you read about it. Moving between those perspectives forces me to question framing, notice what is being emphasized or omitted, and broaden my own perspective. For someone obsessed with language and narrative, it's basically a daily laboratory. Jennifer Grönqvist, diadaya.se. We have this family heirloom piece of furniture from my husband's side—the owner was his great-great-something's brother and awarded the Nobel Prize Erik Axel Kalfeldt. I touch it every morning for luck. Absolutely no sense in it. But I don't have routines or obsessions besides that one. Enrico Guglielmi, Vina Metallia, vinametallia.com. Bring the unexpected, Dr. Noga Gulst. Playing stupid Facebook games when having my morning coffee. Chris Heilman, VP Developer Relations, We Are Developers. I am a huge film buff, and I watch the movie, the behind-the-scenes footage, the making-of documentary, and rewatch the movies with the director's commentary. I especially like watching the making-of featurettes of movies I hated, as often these explain why the final product was such a mess. Nina Horowitz, immunebridge.com. Since I moved to Pacifica, I have a Cinnabon with extra icing for breakfast far more often than I should admit. Norm Howe, senior partner, Validation and Compliance Institute. I do check my email. Jake. Biohacking Romella Janine, founder, Lucid Pattern. I like to watch tarot readings on YouTube. Enough said. John. Baseball is a second religion to me. The last thing I do before sleep is watch the roundup on MLB TV, so I am caught up on all the scores and developments as of that night. First thing in the morning, before I get out of bed, I watch the roundup again to get updated on the West Coast games that ended while I slept. Christy Candel, real estate developer, founder, IND Consulting, co-founder, Elevate SWFL and Elevate St. Pete, IND Consulting, also Elevate SWFL, Elevate St. Pete. Working out. It's not really about fitness anymore. It's probably one of the clearest examples of how I approach everything else in my life. How you do one thing is how you do everything. Being busy isn't a reason not to do the things you know make you better. Sometimes it just means waking up earlier and doing it anyway. Chief Executive Officer, Sovryn. I take a cold shower every morning. Kim, co-founder and CEO, 1 hour of playtime with kids. They provide reflection and the growing pains we all once went through. Learning Spanish. Do the right thing, even it's not the most profitable or popular in the moment. It will pay off in the long run. Most of my daily rituals would probably be unsurprising to anyone who knows me even a little: meditation, creating art, and designing complex systems are all regular parts of my life. What tends to surprise people is the range of individuals I've come to know through my work. Over the years, my clients, colleagues, and professional relationships have included people from fields that many would not expect to intersect with a psychic medium, including entertainers, members of noble families, elected officials in the United States and abroad, and prominent business leaders. Because of the nature of my work, I place a high value on confidentiality. I make a deliberate effort to protect the privacy of those who may prefer not to have their association with a psychic medium become public. Occasionally, someone I never expected to publicly acknowledge our association does so, usually on social media. When that happens, I inevitably receive a flood of calls and text messages asking whether I really know that person. Even my daughter has gotten into the habit of texting me when it happens. Eric Malka, co-founder and managing partner, Strategic Brand Investments. 3-mile walk first thing in the morning, Amber Meixel, founder. Host, The Heart Leader Podcast, Swevera. Pattern observation. I constantly watch for loops. How conversations repeat. How emotions repeat. How systems repeat. How relationships repeat. And I use these observations to ask: What am I creating? What am I reinforcing? What am I ready to stop feeding into? Most of my biggest decisions didn't come from strategy; they came from noticing and shifting patterns. Tomáš Milar, founder, Ekvista/Startup PR, also Checkly.com. Tell yourself and force yourself to be happy and try to suggest yourself that tomorrow you will make a difference. Mindset. I'm waking up like that every day. I will make difference in our industry. Michelle Mayara, Looch. Cleanliness and decluttering. I can't work from a cluttered or dirty space. I like to walk barefoot on the tile, and since I have a dog that sheds, I run the vacuum robot twice a day. Gabriel Osamor, CEO, also CFO of the Black British Initiative, Megasuto. My absolute obsession with automated financial analytics and structural rigor. Coming from the city and navigating the intense rigor of the CFA program, I treat my daily operational inputs with the exact same scrutiny as a multibillion-dollar balance sheet. I do not rely on gut feelings for my daily schedule or my business development outreach. I rely entirely on data and automated reporting frameworks. President, The Asia Institute. I think that my daily prayer is perhaps something people might not expect to be so central. Yash Gad, PhD, founder and chief executive officer, Ringer Sciences. I am a data scientist and AI researcher who can spend an embarrassing amount of time deciding whether something should be orange or magenta. I obsess over visual presentation. I do not think aesthetics are decoration. Sometimes the difference between an insight changing a decision and being completely ignored is whether someone can actually see what you see. And my family would agree that my fashion sense and design aesthetic is questionable, so I have no idea why I obsess over this. Ole Yekini, PhD, CEO, Easy Play. I read fictional books. As a founder, you might expect my time to be filled with business books, market reports, and strategy documents. Those matter, but fiction has become one of my favorite ways to recharge and expand my thinking. Stories teach you about human behavior, emotions, motivations, conflict, and decision-making—the same things that influence how people use products, build relationships, and make choices. George A. Polisner, Director, Civic Works. My treadmill/cardio routine while listening to music is my daily hour of active meditation. Pranav Ramesh, Co-Founder, Lead Poet. I obsess over wording. I'll rewrite a single sentence ten times until it sounds like something a real person would actually say and a fifteen-year-old could understand. Jason Rhodey, NomadLife.tv. Meditation, maybe? Or my morning stretching routine. I don't know. People probably expect me to do those things. Rosalind. I block out hours in my day when I don't work: eight a.m., nine a.m., six p.m. It's my time to be present with my family. Mark Rust, founder plus CEO, consequentlycreative.com. At some point, you need to do something totally different from work, even if it's only for a few seconds. For me, I pick up the guitar and strum a few chords between meetings. It forces me to switch gears. Ava Scalzo, Ava Scalzo Advising. My daily ritual that no one would suspect is having homemade kefir and chia every morning. My morning gym ritual everyone would expect. Noah Shoman, Silo Digital. I play chess at least 20 minutes a day. Sergey Surukov, ntinko ntinko dot com. Secret: I read science fiction when I have some free time. Not a healthy choice, though. I'm working in virtual world all the time, and reading science fiction just helps me running out of reality. My wife is very unhappy. Siggy, Overtune. I like my sleep schedule. Ashish Singru. Birdwatching. Early, at dawn and before the day starts. No specific goals or problem framing, pure exploration and discovery of nature's wonders and surprises. The exact opposite of how I would work with clients during the day. Chocolate. Not very profound, but very true. I stretch like an athlete every day. I now play close to 100 roller plus ice hockey games per year, so I'm usually sore on any given day. I take advantage of this pain to remind me to stretch when it hurts and remember that this process makes sports more fun. Founder and CEO, Note Effect. I mentally map patterns constantly. Conversations, markets, behavior shifts, enterprise workflows, how people react in meetings, what customers are not saying, where technology is quietly heading. I connect dots obsessively. A lot of people think entrepreneurship is about motivation or hustle. I think it is much more about pattern recognition and timing. I also spend more time thinking in silence than most people would expect. Vora Method. Trying to make Frontier AI write good college admissions essays. I have not yet succeeded, but learned a lot about AI and college essays on the way. I track Mammoth snowfall, my golf scores, my workouts, etc., because I'm a data nerd. I still work overnight security shifts. People assume once you've built a company and run it for 25 years, you're past that kind of work. I do it because it keeps me sharp on situational awareness, which is the whole foundation of the disaster preparedness training I run now. You can't teach people to read a room or a threat if you've stopped doing it yourself. I never finish a workday without speaking to at least 5 investors. No matter how tired I am or how packed my day is, It's a non-negotiable rule. Most people only talk to investors when they need cash. I treat it as a relationship muscle that needs daily training. Question eight: How has success messed with your mind in ways you didn't anticipate? Short answers, honest answers. Emptiness after the goal, the expectation of more success, finding out who your real friends are when you're riding high. Paul P.K. Lumi. I appreciate the suggestion I'm successful. I think the challenge is setting a measure for success that doesn't keep changing. Looking objectively at someone else, you'd probably find it easy to pinpoint slam-dunk moments of success, and they'd probably say, as would I, that every time you get close to one, it suddenly seems like not quite enough, or the fact you achieved it signals that it was too easy. It's the accomplishments you can't quite reach that become the obsession and the new true measure. FastSins174. Owner: FastSins174. My measure of success is still in the distance— $5 million in 5 years— but we're outpacing the path I routed. So this initial success is exciting. I'm more confident than ever that business can and should be kept simple. Stephanie Beach, founder/CEO and podcast host, The Marketeer Group. Interesting question. I think it just makes me want to succeed more and build/create more. Knowing I succeeded the first time allows me to be confident and open to taking more risks, believing they will also be successful. Michele Berdinis, President, Beeline Legal. It turns out it's really the striving that gives me the buzz. The having, not so much. Dario Blanco. Success makes me judge myself much more by my failures than by my successes. I went through a failure where, even though we gave it everything we had, the outcome affected a lot of people. For a long time, I questioned whether I should even be leading engineering teams anymore. I genuinely wondered whether I had failed as a leader. What changed my perspective wasn't another promotion or another successful company. It was hearing from people I'd worked with who told me they'd happily work with me again, despite having lived through one of the hardest moments of their careers. That taught me something I'll never forget: people don't remember leaders because everything always went well. They remember how those leaders behaved when things went wrong. Matt Bloomberg, CEO, Markup AI. Golden handcuffs are real, but they're mental, not financial. After building Return Path for 20 years and writing 3 books about how to do it, my identity was the company and the expertise. Walking away from that, and then choosing to do something completely new at 54, meant killing a version of myself that was very comfortable being the scaling CEO guy. And trying to learn a lot of new things at once. AI. Turnarounds. PE. The hardest part of success isn't achieving it. It's letting it stop defining you. Bora, ReachYourApp.com. I don't know if I consider myself successful yet, and that messes with my mind. Nitin Khanna, CFA, President, N3 Business Advisors Inc. Success can make being needed feel like proof of your value. That is dangerous. The more successful you become, the more deliberately you must separate your identity from the business and build people and systems that do not depend on you. Tom Charman, co-founder, Block. It's made me simultaneously calmer and more existential. You realize most things that feel impossible are actually coordination problems, timing problems, or psychological problems. That part becomes less intimidating. But success also distorts feedback loops. Wins normalize very quickly. Your brain adapts fast. You stop feeling the highs the way you imagined you would. And the stranger part is social. The more momentum you have, the harder it becomes to separate genuine belief from status gravity. People start interacting with the projected version of you instead of the actual person. I don't think founders talk enough about how disorienting that can become over time. Success made me overtrust my ability to see around corners. I began to believe that being early, being right, and working harder could overcome almost anything. Then I launched a Singapore startup around metaverse technology years before the market was ready. Within weeks, the Thai baht collapsed, the Asian financial crisis began, and my prospective investors disappeared. Success taught me confidence. That experience taught me humility. Timing, circumstances, and luck can overpower even a strong vision. Being right is not always enough; you also have to be right when the world is ready. Federico Sismondi, BRN DTS. I always thought of myself as self-confident rather than arrogant. After exiting my previous company, that was a life-changing event, and without realizing it, I started giving more weight to my own opinions and decisions I was confronted with how wrong that was once we started BRNDTS because I was too sure about things without challenging them, just based on past experience. There's a real risk in thinking too highly of yourself. That's how success messed with my mind, and I didn't know it until I hit the wall a few times. I think I've corrected it, but I still catch myself making that mistake sometimes. Craig Coolmit. Probably, despite the amount of success or accomplishments I've had, The desire or need to achieve more is never satiated. Jiraj Vik, CEO and CMO, Trauma, Trauma TM, God Syndrome. And overexcessive reflection to counteract God Syndrome. Derek, Instagram Marketing Secrets. You'll doubt yourself more than ever on the come-up and believe in yourself more than ever when you finally make it. Duncan. When I made new worth, I cared less about it. Megan Eskey, President, I don't consider myself to be very successful, only fortunate to be able to pursue my own interests in retirement. Success in America is something very different, but the pursuit of happiness is more important to me at this stage in my life. Founder and Executive Chairman, Bulk Exchange. I'm very careful what I call or determine as success when we are looking at the long road versus near term. What sacrifices were given in order to achieve a success can come back later. I try to stay mindful and in the present as best I can. They call it a practice, for good reason. I passed up opportunities to lead or played small because I'd absorbed a very specific image of what success and leadership were supposed to look like— loud, certain, masculine— and when I didn't see myself in that picture, I assumed the problem was me, not the picture. It took me years to realize I wasn't unqualified for that version of leadership because I was just never trying to become it in the first place. So now, when I talk about redefining success, I mean it literally. We all do better when we all do better. That's not a soundbite for me. That's the entire correction I had to make in my own head before I could lead the way I actually wanted to. Petra Ferm, PhD, Georgia and Molly. I have always been terrified of power, thinking that power corrupts. I still think that is true, so whenever I get too much power, I leave. Which means I have left quite a few high-stakes jobs after success. The one I didn't anticipate was what doing part of my PhD at UC Berkeley did to me. It actually gave me peace of mind, a calmness among all the tech bros. I know I'm good enough, no need to prove that. I can be generous with my thinking and knowledge. No stress, no imposter syndrome. Jennifer Grunkvist, dayaday.se. I do not feel successful in that regard. But I recently finished a book I've been working on for years, and after sending it in, I was crazy depressed. It was just so diminishing, after working with the internet all my life, having to ask permission for somebody else to publish my stuff, just because I want it on paper. I still haven't accepted that and I am thinking about it a lot. What success means for my independence. Of course you can print yourself nowadays, but literature is still a system and credibility game. Enrico Guglielmi, Vinum Italia, vinumitalia.com. Still waiting for it, Dr. Noga Gulst? I once was recruited to be a CEO of a startup. All the signs showed me that it's the wrong thing to do. However, if we succeeded, the revenues would be in billions of dollars. That was the first and last time I allowed money to blind my judgment. Needless to say, the venture failed as expected. VP Developer Relations, We Are Developers. Having traveled that much and stayed in hotels and on the road a lot, I completely lost my sense of home. I don't feel like customizing my flat to my needs, and I don't have any strong feelings whatsoever about what it should look like. This is interesting when you find a partner like I have now who has a massive need for that, making you wonder if it's a good thing or a loss of a basic need people should feel. Nina Horowitz, immunebridge.com. I unfortunately have become even more of a perfectionist than I was before, and I have less time to spend on the details, Our company's 3 core values are attitude, meticulousness, and throughput, and I'm always reminded of the fact that it's really hard to maximize all 3 simultaneously. Some people have listened to me based on what I've done in the past rather than based on the logic of what I'm telling them in the present. That's a mistake. With success comes an expectation of more success. Founder, Lucid Pattern. Again, I don't think this applies to me just yet. I am still looking for my come-up. Maybe. I guess I didn't realize that when I achieved the goal I set out to achieve, it ended up being a false summit, and the true goal is still a ways away. Then achieving that goal turns out to be a false summit too. Disruptors, innovators, entrepreneurs are never satisfied. The work is never done. Christy Kendall, real estate developer, founder, IND Consulting, co-founder, Elevate SWFL and Elevate St. Pete, IND Consulting, also Elevate SWFL, Elevate St. Pete. It makes it harder to know when enough is enough. Success gives you evidence that you can figure hard things out. That's incredibly empowering, but it can also become dangerous because your instinct becomes, I can handle it. And usually I can. The harder lesson has been realizing that just because I can carry something doesn't mean I should. Brandon Carpellis, Chief Executive Officer, Sovereign. To be clear, I haven't had success on my own yet. However, I was successful by all the accepted societal markers in my corporate job. I would say that leaving that job to try things on my own and not being successful yet has really made me question whether or not I made the right decision. And if I am actually capable of making a go of it on my own. B. Kim. Assuming that everyone would appreciate my thoughts and advice. Ellen Malloy. One of the most surprising aspects of my career has been other people's reactions to it. While this happened in a variety of settings, I encountered it most often when I was dating. When men learned that I held a more senior position than they did, earned a higher salary, or had built a business comparable to or larger than theirs, The reaction was frequently disbelief. Some asked me to prove it, as though my career required verification. On more than one occasion, I found myself giving someone a tour of my office or introducing them to my boss simply to convince them I was telling the truth. Other reactions were equally unexpected. Some men ended the relationship almost immediately, while others seemed to swing to the opposite extreme and begin talking about marriage far sooner than seemed reasonable. After experiencing this repeatedly, I stopped volunteering details about my work. If someone asked what I did, I would simply say, "I work at a bank," or "I work in IT." Most people assumed I was a bank teller, and I found it far easier to let them make that assumption than to navigate the reactions that often followed the truth. Eric Malka, co-founder and managing partner, Strategic Brand Investments. Losing my professional drive and purpose after achieving all my goals at the age of forty. Founder, host, The Heart Leader Podcast, Suivera. Success taught me that achievement and peace are not the same thing. For a while I thought impact would eventually create enough evidence that I'd finally feel complete. Instead, success removed excuses. It forced me to realize that inner peace was never waiting on achievement. Now I build from wholeness instead of believing that something I do can contribute to me being whole. Tomáš Milar, founder, Ecvista/Startupper, also Checkly.com. Buying expensive things, you buy BMW or Porsche and you realize that it makes you happy. I realized that I love winning. So, I guess the winning and breaking all the rules or paradigma, that's what is really crazy about our lives. Looch. It hasn't. Success brings peace of mind to people with my personality type. Gabriel Osamor, CEO, also CFO of the Black British Initiative, Megasuto. It has given me a profound sense of urgency bordering on frustration. The more I sit in the CFO seat and look behind the curtains of highly successful, well-funded companies, the more I realize that the gap between the 1% and everyone else isn't talent. It's access to structure. Seeing how easy it is to scale when you have the right commercial architecture makes me hyper-aware of the silent killer affecting underrepresented founders. Success has made me realize that individual excellence isn't enough. If we don't build institutional, generational frameworks, like the national infrastructure we are building through the BBI and SOAS University of London partnership, the wins are only temporary. Emmanuel Pastryk, President, The Asia Institute. My success is a very odd one, so yes, it has been extremely confusing. What I did not anticipate was that I could have so much impact and be entirely invisible to the vast majority of people. In a sense, the only real success in political culture is carried out by those who are invisible. Yash Gad, PhD, founder and chief executive officer, Ringer Sciences. Success makes you way more afraid, not less. When you have very little, you can make huge asymmetric bets because there is not much to protect, especially if you have a bit of a safety net. Once the company works, you have employees, clients, revenue, and a reputation. Then suddenly every reckless decision has a downside. The first thing success gives you is something to lose, so the challenge is not letting that turn you into the person who would never have built the company in the first place. Keep breaking stuff. Ola Yekini, PhD, CEO, EasyPly. Success has changed my mind in a way I didn't expect. It made me realize that the goalpost never stops moving. When you achieve something you once dreamed about, you expect a feeling of arrival. Instead, you discover a new level of responsibility, bigger challenges, and higher expectations. As a founder, success can create a constant tension. You celebrate the wins, but your mind is already focused on the next problem to solve. Director, Civic Works. I'm looking forward to finding out. Co-founder, LeadPoet. It compresses your definition of success. Things that would have felt unbelievable a year ago become the new baseline almost immediately, which is motivating but also makes it surprisingly hard to stop and appreciate progress. Jason Rhode, NomadLife.tv. Your first success makes it very difficult not to try to repeat yourself. But it never really works. Just because something worked once doesn't mean the same formula will work again. You have to approach each new thing with fresh enthusiasm and authenticity rather than trying to recreate whatever worked yesterday. I don't think I've achieved success yet. I'm still on the journey. If you don't watch out, you can get so stressed out going from one thing to another that it drives you crazy. Success has not really messed with my mind. It's just made me hustle harder. Feeling of emptiness when reaching a goal. I don't appreciate success in a true manner and don't celebrate it as I should. Once I reach my goals, I already have a new set of goals. Many people had that too. Siggy, Overtune. I have not got the success I have wanted. I want more Ashish Singru. Long tenure in a role or organization makes you very good at being the person with the answer that everyone trusts, and sometimes in that comforting and flattering ride, you can lose sight of what the answer needs. to prove each time. Working with smaller organizations with less margins for error and less reserves to recover from wrong calls, I have realized that success in being really good at getting an answer is incomplete if you do not get outside your comfort zone of being the expert and are willing to be questioned and to question others as to why the hell are we doing all this instead of backslapping each other. Success showed me how deeply committed many people are to old beliefs and structures, even when those structures are causing them pain. That surprised me. I used to think that if people saw a clearer path to freedom, growth, or aliveness, they would naturally take it. But many people would rather suffer inside a familiar system than step into the uncertainty of freedom. Success has made me much more aware of how attached people are to the very things they say they want to escape. Success once makes you immediately hungry for more. Once you're lucky, twice you're good. But 2 wins just makes you want 3. Getting off this golden rat race requires a hard mental reset to measure success by how many people we help versus how much money we make. Jay Tokosch, founder and CEO, Note Effect. Success changes your relationship with trust. As you become more successful, more people approach you with agendas attached to opportunity, partnership, friendship, investment, or access. You also realize that winning does not remove pressure. In some ways, it increases it because now people expect you to keep winning. The other thing nobody tells you is that success can distort your sense of normal. Risk tolerance changes, your standards change, your patience changes. You start seeing how small most people's thinking is, and sometimes that becomes isolating. Arvind Vohra, Vohra Method. I think ethics become tougher the more success you have. It's very easy to stand on principle when you have nothing to lose. When there's more at stake, it's easy to let them slide, creating inauthenticity and the misery that goes along with it. This has been the toughest personal struggle for me, and what I have wrestled with the last few years. Facing that has made my business stronger and made me individually stronger. This is an ongoing battle. Brian Wally. It can be very easy to fall into the trap of I've done it before, I'm smart, but reality tends to straighten me out on the regular. It made me slower to ask for help. When you've built something people respect— 250+ facilities, clients like Disney and the NFL— there's a quiet pressure to always look like you have it figured out. That instinct is exactly backwards from what actually built the success in the first place, which was asking a lot of questions early and often. Founding partner, Awake Partners. It made me way less naive, but also a bit more cynical. You start to realize that at a certain level, it's often every man for himself. It forces you to always wonder, what is their hidden agenda? Instead of just enjoying relationships purely for what they are. That's the end of the book. This is edition 1. The email goes out to every guest, so new answers land every week. If you answered and want your words out, or you want to see your quote before it's printed, tell me and I'll fix it the same day. Want to be in the second edition? Book the podcast from the link in the book. Thanks for listening.