I'll start.

My biggest financial failure is being a founder rather than just taking a job. I last had a fiat job 5 years ago and the income that I've lost is impressive. In one way, it's kind of high time preference behavior: I wanted to build things that I wanted and didn't want to wait to be rich to do it. In another way, it's low time preference: I was willing to sacrifice income for experience and at-bats.

I'll continue making this mistake probably forever, because I still don't think of it net-net as a mistake, but it's probably the single biggest "purchase" that I could've otherwise spent on Bitcoin.

2nd biggest miss: up until 2020 I still had a relatively diversified portfolio which was also a missed opportunity given my conviction levels.