I was an insurance lawyer with no dependents. 5 years ago, a friend of mine suggested I tried playing Blackjack (he made 300k in a short period of time, and then lost it all). My first response was "Bullshit! You can't win gambling". I read a couple books on card counting, and wrote a blackjack simulator to see if it really worked. I was stunned that it did, so I set out to do it.
I began playing Blackjack, and made about 10k in 2 years of counting. From a $ perspective, it was a waste of time. BUT, I learned a lot which carried over to sports - especially risk management.
3 years ago, a friend of mine told me that you could make money betting on sports. I said "Bullshit", and told him to prove it to me. He had a PhD in stats, so he was able to do that. Amazed at the revalation, I started studying sports - NFL, and Arena Football (it seemed like a logical progression, since I understood football, and Arena started one week after NFL ended back then).
I did well at NFL and Arena, and started attacking Baseball. I had a lot of help from a baseball genius - Don Peszynski. We worked together to develop a baseball model, which plays a matchup 100k times to set a moneyline. I was spending 3 hours a day updating statistics, until I found a programmer who developed software to scrape all the player data each day (he also scraped tons of other data for us - I think any team needs a dedicated scraper/programmer). We did well by making our plays before the lineup was released (our model picked a lot of plays in common with a syndicate, but we beat their price by playing before the definitive lineup was listed).
I (and my group) was never at risk of losing anywhere near our bankroll on any single play. We had plenty of times when we put 20%+ of our bank on a football game, but that has become progressively harder to do.