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Honestly I suggest just spending it. A yacht, fractional jet, a couple of mcclarens, maybe some investment in space technology, etc. Seems like most fortunes I have seen don’t withstand this level of spending. In 7 or 8 years you could completely have your motivation back :)
You're a free man. Use what you have wisely.
Have a family.
Mostly because of insecurities we keep telling ourselves to work hard else you will be left behind. Truth is, even you become successful (in traditional sense), you will not take anything with you after death. Once you take away idea of staying motivated, you will start doing whatever you like. You can find happiness in simple things like waking up in morning, driking a glass of water or cup of coffee.
See how Feyman tackeled burn out. (Burn out doesn't mean working hard and not getting results. It is a successive feeling of not adding any value to your life)
https://www.mymoneyblog.com/richard-feynman-fighting-burnout...
This video might help you. Please watch till end.
So it sounds as though if you gave most of your $ to people who could really improve their lives hugely with a little $, everyone would be better off. Or at least be happier, which is a major form of being better off. Having done something towards helping others and making the world a better place would feel good too, I imagine.
For example, you say you have been lucky at a few startups. The common position here, even for early employees, is that they will see no financial benefit from the company unless they're the founders. How can people be as 'lucky' as you were?
There are way more examples of people being burned and seeing no return than there are examples of people who have been 'lucky', and having gone through it multiple times, you may know things others don't.
My point is, you probably have knowledge that could be helpful to others. You could chime in the several Ask HN threads, or write blog posts, etc.
It would help others avoid some mistakes and amortize the mistakes you've made and what you learned from them by trial and error. For example, sometimes I'll put a reply with a bunch of links to other replies on a topic[0].
I’ve gone through a few transitions in life that relate to this sort of thing, and have worked with a very well known CEO coach on this. His advice was invaluable. He recommended a book on life transitions[1]. Whether you find wealth, retire, or do something else, such a major life transition often requires you to really invest in reflecting on what has changed, what hasn’t, what the deeper implications are, etc. The…