Sure, but it's not either/or. My last company was very profitable but is not going to IPO any time soon or get bought for a crazy valuation. However, I cashed o

Sure, but it's not either/or. My last company was very profitable but is not going to IPO any time soon or get bought for a crazy valuation. However, I cashed out enough to fund my current company. I don't have millions in the bank, but I have enough to give me a 2 year runway and still live a comfortable lifestyle. "Go for broke" companies usually end up just broke. But if you can build a profitable business that finances future endeavors. Last year I had an epiphany that I'll be working in small tech startups for the rest of my life, and that I will enjoy it very much so long as the bills are paid. If I could repeat the last five years 4-5 more times I'll be very happy, even if not a jillionaire.