Jamie Gold was just a teenager when he got started in the entertainment business, and was the youngest talent agent in Hollywood when he broke in, landing clients such as James Gandolfini, Jimmy Fallon, Felicity Huffman, Jeffrey Wright, and Donnie Wahlberg. After getting burned out by being constantly on call, however, Gold decided to take some time off and focus on his new passion, which was poker.

Gold jumped head first into some of the biggest cash games in Southern California, and eventually found success playing tournaments. Later that year he worked out a deal to play the World Series of Poker main event, and after navigating his way through a field of 8,773 players, earned the title and the $12 million payout. In the years since, Gold has been seen on numerous poker shows, including High Stakes Poker and Poker After Dark, but has spent the majority of his time on the felt helping to raise more than $500 million for various causes and charities.  

Highlights from this interview include missing Dean Cain's birthday party, a Woodstock birth, being the youngest agent in Hollywood, the year Jimmy Fallon slept on his couch, why James Gandolfini hated the spotlight, jumping into the biggest cash games BEFORE winning the WSOP, hanging around Johnny Chan for poker tips, table talk, trading celebrities for buy-ins, the truth about his deal with Crispin Leyser, money misconceptions, 'losing $1 million' in a city he hasn't been to in a decade, being cheated in private games, from Molly's Game to Inside Game, the Hollywood party that made the Playboy Mansion look boring, getting yelled at by Jack Nicholson and being consoled by Paul Reiser, a four-day poker session, what Robert Downey Jr., Stephen Colbert, and Chad Lowe have in common, betting a yacht on the Super Bowl, and seeing Bad News Bears 22 times in the theater.