In this episode, Reid sits down with Tony Lillios, a serial entrepreneur who sold companies to Samsonite, made the Inc. 500 list multiple times (reaching as high as #41), and became the first person to swim across Crater Lake without support.

Tony shares the raw moment he saw "two commas" in his bank account for the first time, how he navigated a catastrophic $15 million inventory crisis, and why autonomous decision-making drives both his business ventures and extreme endurance challenges.

From creating life-changing wealth for his employees to swimming five and a half miles in 50°F water without a wetsuit, Tony embodies the grit-it-done mindset. 

Whether you're seeking business insights or contemplating your next impossible challenge, this conversation delivers practical wisdom wrapped in unforgettable stories.