Glazer had often earned extra money during his education by taking trips to Las Vegas or Atlantic City to play blackjack and poker. After his aborted law career, he resumed this habit while he tried establishing himself as a writer. He soon found himself achieving greater success in poker than in writing. Glazer later met Phil Hellmuth at a spiritual place in Northern California called Esalen and they became close friends. His relationship with Hellmuth led to Glazer becoming the tournament reporter for the World Series of Poker. His tournament reports were widely liked for their regard to detail and emotion.