The Wall Street Journal has a very interesting interview with Edward Thorp and Bill Gross. When he was a young math professor, Thorp developed a (famous) system for wagering on blackjack that maximized winnings. He then applied his system to the biggest casino in the world: Wall Street.
Wall Street Journal: How did you get interested in blackjack?
Edward Thorp: I went to Las Vegas in 1958. I'd learned a strategy that would let you play just about even, so I decided to play with $10. My $10 lasted a lot longer than anyone else's at the table. I thought there had to be a mathematical way to beat the game, and that would be interesting mathematics. I figured it out and a few years later I wrote "Beat the Dealer."
WSJ: What about you, Bill?
Bill Gross: I picked up Ed's book in early 1966. I got in an automobile accident and had to go into the hospital and had time to practice the card-counting technique he discovered. And it worked! I had $200, so I headed out to Las Vegas. I turned my $200 into $10,000. I didn't care about the money. I wanted to prove that you could beat the system. Then I thought about what I could do that takes the same skills. I realized it was investing.
Mr. Thorp: He started out with $200 and now he manages nearly $1 trillion.