- When I was 30 I sold my first company to a company that eventually went bankrupt.
- When I was 30 I could've built a company around products (which are valued more) than around services, which I did. That probably cost me millions of dollars.
- When I was 30-31 I spent 365 days straight playing poker without spending more time on my family, on health, on creativity, on positive things.
- When I was 32, at the height of the dot-com boom, I started a venture capital fund. I invested millions of dollars in dot-com companies and lost it all. From peak to low in 2000-2002, $15mm cash to $0 and losing my house. I had to start from less than scratch (I owed taxes after hitting $0).
- When I was 34 I hung up the phone on my dad in an argument and never returned his calls. Six months later he had a stroke and died. A week before that he had emailed me to say hello but I didn't return the email. I'm sorry, Dad.
- When I was 36 I started a fund of hedge funds. I turned over every rock on Wall Street to find something good to invest in. There was nothing good to invest in. All of Wall Street is a scam. Capitalism is good but Wall Street is a scam. When I was 38 I shut down the fund of hedge funds. There was nothing to invest in.
- When I was 39 I bought a house at the top of the housing market. Then I got a divorce. Then the stock market crashed. Lost a house, a family, and all my money. Again.
- When I was 39 I caused someone's death. But that's another story.

My early 40s got a little worse.

But then they got better. A lot better. A whole lot better.