Background story: did a startup as a CEO+CTO. 100 hours a week, mostly because I had to play two roles. It seemed easier to find a CEO than CTO.
So we were burnt out. Sold the startup. Made 750% ROI in a year, which is a good investment. Planned to reinvest that money into startups for maybe even a 300% ROI.
The plan was to go CTO route and rely on someone else to play CEO.
It didn't work out - most people were decent at business skills, but terrible with product. Some could build a million dollar traditional business, but couldn't make it in the startup space - they were too cautious, too scared of committing, or wanted passive income. There people with sales experience, who are great at forming strategic partnerships with big corporations, but don't dare talk to the customer.
So that was a mess. I regret expecting others to do well when given the trust and opportunity, even if they had done well in the past. I regret following logic over instinct, and following people who were not "animals" like Paul Graham suggested.
I'm working on a startup now, but it's the unsexy idea I had 3 years ago. At least I get full control over product and customer development.
* spent about 20k renovating a home office
* subscribed to Joox/Spotify and purchased all the games I once pirated
* donated 10% to charity
* gave a fat envelope full of cash to my wife (she was so shocked that she suspected me of having an affair)
* gave money to my mom
* bought bitcoin and other crypto
* got a will done because bitcoin isn't covered by inheritance laws (also for religious reasons)
* considered investing into a restaurant, but it was too much work
* invested most of the rest into startups which all failed
* paid for funeral fees for dead companies when partners passed the ball
* looked for a job after burning through it all