Bill Gurley is a legendary venture capitalist who has backed companies like Uber, Zillow, and OpenTable. His new book, Runnin’ Down a Dream, is a user's manual for figuring out what you actually want and how to go get it. In this conversation, he shares some of his favorite takeaways from the book. Plus, Bill reveals the one skill he desperately wishes he had.

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Kerri Walsh Jennings is a five-time Olympian. The queen of beach volleyball has some seriously inspiring words for everyone, from the kids she coaches through her platform P1440 to the pros on her new Major League Volleyball franchise. Plus, she's bringing Hero Beach Volley to Montauk this summer, and Dan's fired up to jump in and get spiked in the face.

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Steve Mould started out doing stand-up comedy at Oxford for fun, because apparently getting a degree there isn't hard enough. When he combined his love of physics with performing, he unlocked a whole new level of success. Now he's an author, occasional TV presenter, founder of a comedy festival, and host of the long-running Steve Mould YouTube channel with 3.5 million subscribers and 985 million views. He joins Dan to talk about turning a passion into a business without destroying your soul in the process.

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Dan is joined by the Warped Tour founder, Kevin Lyman, alongside the founder/President of FestForums, the leading B2B conference for the festival industry, Laurie Kirby.  Kevin talks about his favorite memories from the tour and his time with the musicians. Along the way, he offers some punk rock lessons in marketing and matching the message to the audience.

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Seth Berkowitz was over late-night pizza. What he really wanted was a warm, just-baked cookie delivered to his door. Since he couldn’t get one, he built Insomnia Cookies in his dorm room. Berkowitz shares the simple, disciplined game plan that turned a craving into  350 late-night cookie-delivering stores worldwide.

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Liz Tran, author of the forthcoming book AQ, knows that the one constant of life is change. She joins Dan to share practical ways to build real resilience and rethink how you handle the unexpected. Plus, Dan makes a surprising discovery...about himself.

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Bert Jacobs built Life Is Good with his brother, a beat-up van, and $78. He explains how positivity became a competitive advantage and why giving back was never optional. The Playmakers nonprofit grew alongside the brand and sits at the core of its “why.” Bert also shares his belief in capitalism and business as the only way to save the world.

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Music producer Jimmy Humilde is added another title to his résumé with his new film, Clika. Even as he becomes a true multi-hyphenate, he shares practical advice on managing nerves and staying grounded through gratitude. Plus an unconventional approach to meditation.

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Joel Milton, co-founder of Splash Sports, has made it easy for anyone to run a contest with friends or fans. But running the company itself is much harder. In this snack-size episode, Joel talks about building a business when the rules keep changing, how to avoid chasing shiny ideas, and why getting something out into the world matters more than getting it perfect. Plus, Dan responds to the comment section.

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No matter how you measure it, Bert Kreischer is a success. And yet, the fear never really goes away. In this conversation, the stand-up comic, podcasting powerhouse and star of the new Netflix series Free Bert, talks about imposter syndrome and what actually drives his relentless work ethic. He shares his formula for telling a great story and explains why the most awkward celebrity interactions often make the best ones. Plus, Guy Fieri drops in to ask Bert a few questions of his own.

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