I'd use $10 million to set up trust funds for my parents, my little brother, and my girlfriend. I'd take $80 million and use it to set up a conservatively (government bonds) invested, self-sustaining trust for myself. The other $10 million I would use as my starting bankroll... I'd buy a couple of houses, buy cars for my family and closest friends, and spend the rest of my life having as much fun as all of that money could buy.