1) Kick myself for not selling six months ago when valuations would have been stupidly higher (relatively speaking). :) I think this is the grown up version of

1) Kick myself for not selling six months ago when valuations would have been stupidly higher (relatively speaking). :) I think this is the grown up version of "I'd wish for a million wishes!" 2) If the money is larger than just being comfortably set, I'd split it into two pieces -- one being a charitable giving platform modelled after the Bill and Melinda Gates foundation ( http://www.gatesfoundation.org/grantseeker/Pages/foundation-grant-making-priorities.aspx http://www.gatesfoundation.org/grantseeker/Pages/foundation-... ). 3) The other half into a fund for playing / investing / geeking. I think once you get to the point that you have enough money that you don't need to go into work any more the next horizon is to make other people successful like you (looking at YC, here) On the other hand, if it was enough less that this wasn't really doable, I'd at least structure the money in such a way that I couldn't blow it immediately. I understand that it's too common for lottery winners to become depressed and possibly even suicidal after mismanaging their money. It would be important to cover this before I started spending money on things that I would think I wanted (Porsche 911 turbo comes to mind immediately).