People do not get very many quality-adjusted life years -- why would you spend 8+ hours per day doing CEO work when you could spend that time with family and friends?
Making the big calls, having people who'll go do all kinds of stuff when you ask them to, meeting and hanging out with other important people, et c., probably feels awesome, and if you've got enough money socked away to never need to work again, all the "risk" is as real as playing poker with pennies.
Okay, time to get rich.
My dream home would need space for a home gym, workshop, and small office. Having a home, a home big enough for all of that, and then getting all of that would not be cheap, but it would mean dead-simple access to things I need and things that make me happy and fulfilled, which would mean more time spent fulfilling myself.
Your family and friends are usually busy working.
The only exception is if you roll with other wealthy (early) retirees. If you have ever spent time around these folks, you might see why it’s not necessarily that compelling.
I would humbly suggest that it’s easier to meet and hang out with interesting people under the guise of owning or working in some sort of business. If you actually like that business (many people do), then it’s a double win.
If I struck rich or won the lottery, I'd want to start doing CEO work, while funding my own rather ambitious projects. It would be unlikely to be someone else's company, but perhaps if I met the right person(s). Most likely, I'd hire a bunch of people, and they would help me with big R&D projects.
Why would I want to waste 8+ hours a day hanging out with family and friends? I mean, I like family and friends. It's nice to spend time with them. I love them, and life would be missing something important without them. But it's not fulfilling to do it all the time.
I'd really like to use my time here figuring out and building things, and the things I'd like to build are too big and adventerous to do by myself. They're also too big and adventurous to do putting in only a small fraction of the day: I'd either need to put in a lot of time, or there's no point.
It doesn't come from just wanting to do the work. It also comes from imagining looking back on life when older.
When I imagine looking back on a life of hanging out with family and friends, having fun, having big personal moments, ups and downs, all those memories, remarkable times, that seems very special, magical even. Very special!
But I have to admit, not enough by itself. Given the chance, it's also motivating to want to be able to look back and see some of my grander dreams realised in some form. I can't explain why; it feels like an intrinsic motivation, and quite a burden really, because truth is, that's unlikely to happen. But seems worth trying.
I imagine at least some well-off CEOs who are managing something big, even if it's not their own company, must be getting a similar sense of satisfaction from some internal drive to do something like that.
Selection because only workaholics or super-strivers generally make it to that level.
Survivorship because the only ones you see working are by definition the ones that didn’t quit. It is possible that many people who made that kind of money have quit and are just being quiet about it.
Alternatively you just don't see the people who retire and spend time with family and friends. They don't post here, they don't have blogs, they don't have articles posted about them. They are just living life.
That's the ideal way to go, imo. I'm trying to slowly figure out what I need to live that kind of life, so that I can become some sort of cyberpunk mountain man when I reach financial independence. Identify what makes me happy, what I need for those happiness-generating activities, etc, and make sure that I'm set up to enjoy myself.
A lot of people seem to prefer contributing to wikipedia or writing free software to partying, so it doesn't seem far fetched.