Yeah in this case he bet it all. Now the initial investment was probably closer to $50-100k, and I’m not sure what his backup contingencies were (most of that was investment in physical product, which always has a certain level of resale value).
Some people will say “you can always go BACK to insurance” I’m sure with many years of experience you could always find another job doing what you do now if your new plan fell through - you’re the only one who has to sleep at night with that decision.
I took the risk gamble by leaving a comfortable corporate job and moving to a startup. I figured this is the time to do it, not in a few years when I’m trying to start a family. We’ll see in a few months/years how that pays off.