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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this powerful and deeply personal episode of Put Your Funny Where Your Mouth Is, Vince Carone opens up about his years-long battle with gambling addiction. From childhood trips to Las Vegas to high-stakes blackjack tables as an adult, Vince walks us through the early seeds of his obsession, the thrill of the win, and the crushing weight of the loss.
Alongside co-host Dobie Maxwell, the duo balances heartfelt honesty with humor, showing how addiction can take hold when you least expect it—and how it weaves its way into careers, relationships, and identity. Vince shares vivid stories, from winning $13,500 at a Vegas table to giving half of it back in the same night, revealing how the illusion of control fuels the cycle.
Key Points Discussed:
- How Vince’s family trips to Vegas and childhood games planted the early seeds of gambling
The emotional highs of winning—and the psychological spiral of chasing losses
Why addiction often hides behind “fun” until it takes over
The role of control, ego, and rationalization in fueling the behavior
- The moment Vince started to realize he had a problem—and the early steps toward recovery
This is part one of a two-part series where laughter, vulnerability, and life collide. Whether you’ve battled demons of your own or just want a peek behind the curtain, this conversation reminds us that every high has a cost—and that help is always possible.
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