"You coulda been somebody"—but you paid some low-level secretary to leak quarterly filing secrets to you and got caught. Now you're in prison. Whoops.

You bet big that the market was going up a lot—and were wrong. Your investors sued you. You escaped jail but you're broke and not really qualified to do much other than small bean counter-y functions for local businesses. Nice work escaping from jail, though.

You came, you raised, you invested. But that's about it. Your investment results were never particularly distinguished, so you never raised gobs of money; but you fought the war for a couple decades and had an okay life. You would've done just as well if you'd followed your childhood dream of being a vet, though.

You bet and won, most of the time. It meant millions—and then later in life, tens of millions—in your pocket. Nice conferences with the fam at fancy resorts. Decent golf game. Respect of peers. Nary a material thing you want for. Owning your own island would be nice.

Billionaire status. Power. Greed. Fun. You get to sponsor an election in your Congressional district. You get to endow university chairs—and a wing. You give $100 million to a pet cemetery when you die. Just 'cause.