I'll do a throwaway for this. Company had an exit that was about $120m personally for me about 3 years ago. It was a hard slog of about 14 years during which time me and my cofounders got sick of each other, most relationships that I came in with blew up and so on.
It is so very strange to not work. First off, everyone all the time is lightly nagging you to work. I don't want to work! I already did that. Surprisingly it is my retired parents who nag the least since they understand retirement the best. It's everyone else my own age (35) that is weird. People who lightly know you ask 100 questions and you sort of have to lie or carefully select truths when you first meet someone because it goes badly saying what you really think most days. Some variation on "Don't you get bored?" constantly coming up. Answer is - no!
After a few years of this lifestyle I am settled in quite nicely and almost don't remember working except as a distant other life. I work out, I see friends, I go drinking, I get up at 7am, I read Hacker News, I do a hobby here and there. Any time I throw myself into a hobby I typically find it fills 2-3 hours a day that is just about enough time in a day to be busy for me nowadays.
One thing that definitely differentiates is I can travel and do the hobbies of a rich person. I rarely get to throw around numbers with strangers so almost weird to even type but I am spending $2.4m this year just on my little pet projects. Not businesses - just stuff I wanna do for fun with no real purpose.
I am very serious about managing my money and I'm a wealth manager's worst nightmare. I meet with everyone, talk endlessly about what is possible, read a lot on investment, and very very rarely give people my business. They are welcome to pitch but after meeting with a ton of folks I ended up making it my part time job and I always know more than the back slapping sales guys they send to try and get 1% fees out of me.
You end up finding other people in similar situations. I have a good friend from my startup days in a similar boat with a slightly lower number who made $8m on crypto this year purely out of boredom. He made $10m the year before on a startup he cofounded for 18 months again out of boredom. We get together every week or two, talk about the struggle to keep busy but not too busy. Ha it sounds like we are complaining! It's just a balance as we navigate having fun with projects but not getting stuck in a decade long slog again.
I guess I like the idea of being 'rich uncle' or 'grandpa' to a startup, having a flexible amount of involvement. Perhaps daily for 6 months, 4 days a week for a year more, and then 1 day a week from there. In the real world I just worry I'd be so involved it would accidentally be me killing myself and stressing out for 7 years to build a $20m company when my investments make me $7 a year living my life with freedom.
Dating is a bit funny when you don't work; you sort of self-select the people for whom it is an issue. People see my house at some point in the dating cycle and there's no hiding the situation. I have on a whim with 24 hours notice taken a girl I was attracted to across the world, had a great week, and then basically that was it. But by and large dating is just normal go around have dinner get a drink stuff, no helicopter sunset champagne yacht adventures. I feel a little bad I'm doing it wrong. Very few gold diggers in my life, surprisingly. I kind of was hoping at one point my friends would have to tear me off of some model. Ah well. I watch TV shows like Ballers and their idea of what rich people are like is really funny to me; I do normal things and date normal people. I suspect based on dating history I'm going to become a stay at home dad to a career minded woman. I suspect it is rewarding to raise the kids?
