Problem Solvers

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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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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