Man, I can't believe I've never thought about this with any detail beyond (I'd pay off my debt). I reckon I'd call my buddy who is an estate planner and figure out how to protect whatever I can for starters. I figure I can count on $400 million in cash to do what I please.
1- Write ridiculous checks (I'm thinking $25 million +) to College Park Baptist in GSO, Backpack Beginnings, and a couple other charitable organizations that move me. I'd write WFU Athletics a nice check to upgrade the Joel. There goes $125 million!
2- I have a small family (4 parents, one sister, a few in-laws). I'd write them each a check for $500,000 and then set up a drip that gives them $60,000 per year for life and tell them if they ever ask for another penny they will never hear from me again. I'd do the same with some life long friends. There goes another $15 million! I'm down to only $250 million. Whew.
3- Buy some land in Asheville and build a great house with my wife. Probably out by Brevard. That would be the primary residence. then a townhome right in downtown Asheville and one in downtown Greensboro and one in Wake Forest, the town. I'd put my mother in law up on Wrightsville in a great house where her arthritis wouldn't bother her so much. I'd buy a fun lake house with a great dock and a fun boat. Plus jet skis because my wife loves a jet ski. That's it for property. My version of a great house is probably around $1.5 million. Something like 6 BR, 6BA with a pool and dock. A townhouse is just a normal townhouse. 3 bedroom, 2 bath type. I'd be down to about $240 million. Sheesh. I'm almost BROKE.
4- I'd buy out all of my business partners and allow key employees to buy in slowly over time after significantly improving their quarterly bonuses. Then I'd hire enough people to stay slightly overstaffed instead of perpetually under staffed. I'd include someone to do my job who is better than me and quit. I'd serve on the board. That would cost me about $30 million today, but it's profitable enough to stay above water even staffing up a good bit, so it wouldn't be a drain. Down to $210mm!
5- I'd buy a kid's camp up in the Asheville area and run that for my real job. There would be no fee for those who can't afford it, and we'd work hard to turn good kids into great kids by teaching them empathy, self-reliance, the value of hard work, how to be a servant-leader, etc. Probably end up spending $20 million on that when it's all said and done. So I'm down to $190 million. Again I would hire the right people to work it and I'd do vision. It would need to about break even.
7- New Subarus for my wife and I, at each house! We so fancy.
Then I'd spend my free time, which would be rather substantial, riding bikes with friends and traveling with my family. Because honestly, that's what I like.
I reckon that's about it.