Christina Cassotis is the CEO of Pittsburgh International Airport.  In this snack-size episode, she explains why airports are high-stakes problem-solving machines, how to make holiday travel less stressful, and what passengers almost always get wrong about who’s actually in charge. Plus why airports are the best places to work… just don’t call it a tarmac.

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Jeremiah Gardner likes to get deep. He’s an underwater cave diver who uses lessons learned beneath the surface to help leaders and businesses survive and thrive in uncertainty. In this episode, he shares his “Gold Line” framework for moving forward boldly without losing your way. Plus, why learning fast matters more than failing fast.

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Ryan Bitzer and Damion Greiman, plus the always-on-point Amanda Zuckerman, join Dan to break down the comedy business from every angle. On the comedy side, they dig into what’s trending and why getting to “the funny” faster matters more than ever. On the business side, they share the hire that kept their company sane. Plus, what do you do when the comedy special cameras start rolling, and you’ve got a wildly weird crowd to contend with? 

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Orchids. Infernos. Rin Tin Tin. What do these things have in common? They’ve all been the subject of books by Susan Orlean.  In her new book Joyride, she pulls back the curtain on how she does it. Susan and Dan dig into how she decides which ideas are worth pursuing, how she pushes through the doubt, and why audiobooks might just be the purest way to experience a story. Plus, she shares the one writing habit she wishes she could ditch.

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If you’ve got “take actual time off” on your holiday to-do list but keep finding yourself sneaking in “just one more email,” this one’s for you.  Just in time for the holidays, Dan revisits this chat with Reddit co-founder Alexis Ohanian, where they talk about why taking a break can be the best thing for the quality of your work. Plus, what’s the one thing he can beat his wife at?

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Turns out Jack Daniel’s isn’t just a whiskey company, it’s a family business. Master distiller Chris Fletcher stops by to share how he followed in his grandfather’s footsteps but he’s not the only one with a family tie on the team. He talks about legacy and what it means to serve a community that’s been working together for generations. Part of that is Operation Ride Home, a nonprofit that helps junior enlisted service members make it home for the holidays because Jack Daniel’s knows just how much family matters.

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In this snack break,  Dan revisits his conversation with Tracy C Dyson (no relation to Sir James Dyson from the last episode). Tracy breaks down what it actually feels like to be launched off the planet and step into literal nothingness on a spacewalk. Plus, she also settles the debate once and for all: the Earth is extremely, unambiguously round.

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Sir James Dyson can’t stand bad design. Instead of complaining, he channels that frustration into building machines that make the rest of us wonder, “Wait… why wasn’t it always done this way?” And he doesn’t stop at vacuums. From high-tech farming to championing the next generation of innovators, Dyson shares how relentless curiosity (and yes, 5,127 failed prototypes) can power a lifetime of breakthroughs.

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Aaron Levant, the CEO of Complex NTWRK media, drops in to talk about why “ignorance is rich,” how taking wild swings has shaped his entire career, and why real-life experiences beat a thousand Instagram likes any day. This quick burst of inspiration will get you hyped to go out there and try anything. Even if everyone’s telling you not to.

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Gabriel Weinberg knows a thing or two about taking big risks on big ideas. He’s the founder and CEO of DuckDuckGo, the privacy-first search engine taking on the giants. In this episode, he breaks down the frameworks that help him lead, how he makes tough calls, and where he finds the time to actually do all of it. Plus, he gives us his take on the real risks around AI and privacy.

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