When I was 18 I went to college and went about $50,000 in debt. Why would an 18 year old do that to themselves?
I majored in computer science. 8 years later when I got a real job they made me take remedial programming classes after I crashed everyone’s email and trashed the network.
When I was 21 I went to graduate school and got thrown out less than two years later.
They told me when I was “mature” enough I could come back. I don’t know. Maybe one day they will let me back.
When I was 22 – 27 I wrote a bunch of novels and dozens of short stories. All of them were rejected by 40 publishers and probably most of my friends hated them but were embarrassed to tell me.
When I was 24 I was the 8th employee at Fore Systems. I made a game, “Missile Command” to demo their product. Then I quit by walking out one day hitchhiking and never returning. A year later they went public and employees 1-50 became multi-millionaires.
Between the ages of 20 and 30, 10 women broke up with me. I don’t think I broke up with any of them. One of those ten is Facebook friends with me. Two are dead.
When I was 30 I sold my first company to a company that eventually went bankrupt.
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 32 I started a company which raised about $100 million. Lost it.
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.
Nobody in my extended family speaks to me anymore.
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 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. 10 of the funds I invested in were probably scams. 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 started a company I still believe in but I was so depressed I let it just disappear.
When I was 39 I started yet another hedge fund. This one lasted for two months before I shut it down.
When I was 40 I started a company I didn’t believe in and wasted $40,000 trying to build it.
Someone said to me the other day, “it’s good to make lemonade out of lemons”.
I hate lemonade.
When I was 18 I didn’t know what the outcomes of things were. I still don’t. I can’t say “bad” or “good” on any one event. Who knows?
My early 40s got a little worse. Then a lot worse.
But then they got better. A lot better. A whole lot better.
I’m glad everything happened. I’m very grateful.
I wouldn’t change a thing.