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.

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You know what you do, but does anyone else? There's often a gap between what you offer and how you explain it. In this episode, Jason shares his framework for closing that gap, so your audience knows exactly what you're offering, and why you're the right choice.

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A viral ad from Columbia Sportswear caught Jason's eye. After he wrote about it on LinkedIn, the company reached out. So Jason sat down with Tim Boyle, CEO and third-generation owner of Columbia Sportswear, to find out where the idea came from and what it reveals about how to reposition a legacy brand. The outdoor apparel industry had gotten serious and self-important. Columbia decided it was time to bring back fun.

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Having one of the most recognizable and beloved celebrities in the world attached to your brand seems like it should be an easy win. But getting someone to buy once is one thing. Getting them to buy again is the real test. Cordell Broadus (Snoop Dogg's son) and his business partner Sam Rockwell explain what it actually takes to build an ice cream brand like Dr. Bombay, one that delivers value beyond a famous face. In this episode, they break down how to make a celebrity partnership work on a deeper level and how to work with celebrities in a way that's authentic, not just convenient.

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The kids' juice aisle looks completely covered. So does the protein market. Most people would conclude there's no room for anything new. Ciara didn't. The Grammy-winning musician and mom of four was watching her daughter refuse every protein option put in front of her. So Ciara started looking for solutions and met Chris Koch, a CPG entrepreneur. Together, they founded Frosh, the first protein-enhanced juice for kids. She sits down with Jason to share a lesson in how the best opportunities are often hiding inside the markets everyone else has already written off.

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Sami Inkinen is a three-time founder and world-class triathlete. A triathlete! And yet he went to the doctor and discovered he was pre-diabetic. The news triggered a series of changes including a pivot away from his real estate startup Trulia toward his healthcare company Virta Health, where he's now on a mission to reverse metabolic disease in one billion people. And along the way, he developed something he calls sustainable high performance. It’s the idea that if you're building something that takes decades, you'd better figure out how to last that long.

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