Problem Solvers

Tom Szaky built TerraCycle into a recycling giant, then decided recycling wasn't good enough. His new venture, Loop, aimed to replace disposable packaging with reusable containers for brands like Tide and Häagen-Dazs. Consumers loved it. Retailers loved it. So why did it nearly die in four out of five test markets? Szaky breaks down the hidden flaw that almost killed Loop, and the simple insight that finally made it scale.
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Here's a number that should stop you: 11,000 pairs of jeans, sold in 36 hours, from one video posted by a customer with just 5,000 followers. That's the end result of years of work by Brieane Olson, CEO of Pacsun, who decided her brand needed to stop talking at its customers and start building with them. In this episode, Olson shares strategies from her new book, Co-Created, and what she thinks most companies get wrong about "community" in the first place.
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Leadership expert Ryan Hawk tackles one of the biggest traps for ambitious entrepreneurs: dabbling in everything and committing to nothing. Ryan unpacks the idea of “beefing up your obituary” by becoming the kind of person people remember for deep work and sustained excellence—not half-finished projects.If you’ve been spreading yourself thin across side hustles, content platforms, and random opportunities, this conversation will help you identify your “one main thing,” build an ecosystem around it, and know when you’re still just coasting versus when it’s time to dive. Check out Ryan's new book, The Price of Becoming.
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Naveen Jain has built multiple billion-dollar companies all without being the smartest person in the room. His secret? He asks the questions the experts are too expert to ask. In this episode, Naveen joins Jason to make the case that your biggest weakness might actually be your biggest asset - if you're curious enough to use it. Naveen breaks down the framework behind his new book, Counterintuitive, and why approaching every problem like a two-year-old could just be the smartest trick of all.
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Jason and Emily McCarthy built GoRuck into the leading name in rucking.
But when rising costs forced them to raise prices, that community became
more than a marketing asset. It became the reason the moment didn't
turn into a crisis. Jason and Emily explain why with a loyal community
being upfront with bad news is always the smarter play.

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