Molly Bloom recounts how a skiing injury led her from L.A. restaurant work to orchestrating exclusive poker games frequented by celebrities like Tobey Maguire and Ben Affleck. She built her reputation on trust and discretion, but faced betrayal when a player stiffed her for $250K, forcing her to reevaluate risk and vetting. After relocating to New York, her success attracted mob involvement and violent threats, culminating in a federal investigation that seized her assets. Despite being pressured to become an informant, she refused to name others, avoiding jail but losing everything financially. Her story later became a memoir and Aaron Sorkin’s film *Molly’s Game*. The discussion also touches on the psychology of gamblers, spotlighting competitive archetypes and unexpected talent among celebrities. She concludes with insights on sales coaching, emphasizing empathy, presence, and embracing discomfort to build authentic connections.