4. Chris Moneymaker

Chris Moneymaker’s journey from being a normal accountant with the side hustle of working in a restaurant in 2002 makes him a true example of rags to riches in a gambling scenario. As he got more immersed in the world of online poker, this rapidly transformed. He signed up for a $86 satellite tournament in 2003, and as a result, he was awarded a spot in the 2003 WSOP Main Event.

When he eventually conquered the WSOP Main Event, his life was more upended. He resigned from his job to serve as a representative for PokerStars and Harrah’s Entertainment. In addition, he prudently invested his earnings in starting his own business, MoneyMaker Gaming. His career winnings total over $3.5 million, which includes the $2.5 million from his WSOP victory.