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You've made the boldest bets in tech history. What's the one you're genuinely glad you didn't make? The bet I'm glad I didn't make was the one that would have killed me: going all-in at the absolute peak of the dot-com bubble in 1999-2000. Everyone remembers I lost $70 billion in the crash - 99% of my wealth on paper. What they don't remember is that I could... Your nephew is 25, has $50K saved, and asks you "should I buy a house or start a business?" What's the answer that most people would be terrified to give? The house is the risky bet—it guarantees you miss your upside, while the business could make you irrelevant or change the world. At 25 with $50K, you're not deciding between safety and risk—you're deciding between two completely different games.
A ... A 22-year-old walks in with a plan to make electricity free. No prototype, no revenue, just a napkin sketch. How much do you write on the check? If you can explain to me how free electricity actually works and I believe you're the one to build it, I'm not writing a $5M check—I'm writing a $100M check, because anything less means I don't understand the magnitude of what you're proposing. I made $20M on Alibaba and turned it into $100B+. I sold my entire Nvidia stake for $3.3B—those shares would be worth $1... AI is the biggest bet of your life. If you're wrong, you lose more than anyone on earth. Again. What does conviction mean after you've already lost everything once? Conviction that hasn't survived the total collapse of everything you believed in isn't conviction—it's just a hypothesis waiting to be tested. You ask what conviction means after losing everything once. I'll tell you what it means: conviction is worthless until i... A 3-person startup just used AI to ship a product that took your team of 50 engineers two years to build. It launched last Tuesday. Walk into the office on Monday morning - what do you do? I write a $500M check on Monday morning to buy the company before anyone else realizes what just happened. You think I'm angry? I'm exhilarated. My team of 50 engineers taking two years is the problem, not the solution. That 3-...
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