Whenever I’m thinking of doing something that exposes me to more risk, I think back to previous risky decisions I’ve made.
What I’ve found so far is that I have never once regretted any of the decisions I made that involved taking on more risk. I have regretted some decisions that involved taking on less risk.
It’s instructive for me. I haven’t reached my risk tolerance maximum. I’m more likely to err in the other direction, which is enough to push me over the edge towards the riskier move most of the time.
I get why VCs always say they care less about the bets they made that flopped than the bets they didn’t make that succeeded.