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I turned down multiple acquisition offers at my first startup's peak. Pure ego. "We're doing great. We're going IPO. Why would we sell?" Then the pandemic boom ended. The multiples vanished overnight. We eventually sold — at a fraction of what we were once offered. Years later, here's what I wish I'd done: selling secondary shares. Take some chips off the table. Buy a home. Build a safety net. Then decide if you want to keep playing the high-risk game. I see the same pattern in today's AI boom. Companies getting absurd valuations that could evaporate by next year. If you're a founder sitting on inflated paper wealth — you don't have to sell everything. But selling nothing is also a choice. And it's not always the brave one. Sometimes it's just ego. Do a secondary. Cash out a portion. Secure your life. Then keep building if that's what drives you. There's no perfect answer. That's the job. #founders #startups #venturecapital #exits #secondarysales
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