Problem Solvers

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. Learn more about your ad choices. Visit megaphone.fm/adchoic...

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. Learn more about your ad choices. Visit megaphone.fm/adchoices

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...

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 beyo...

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-enh...

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 s...

David Rusenko built Weebly from a dorm room start-up with friends to a business with 300 employees and over $200 million in revenue. But somewhere around employee 25, he hit a wall and realized the problem wasn't his team. It was him. A chance dinner with Richard Branson changed everything. Learn more about your ad choices. Visit megaphone.fm/adchoices

The President of Burger King, Tom Curtis, knew the brand had gotten stale and that customers had drifted away. So he did something almost no executive does. He gave out a phone number and told people to call him directly. Over 41,000 calls came in.  What followed was a viral moment but more importantly, it became a real-time feedback engine. Tom sits down with Jason to talk about why he opened the...

Unsure what to charge for your services? You're not alone. Ilana Golan struggled with that too, until she developed a framework she now teaches to others through her Leap Academy . On this episode, Ilana helps you set your rates and get what you deserve. Learn more about your ad choices. Visit megaphone.fm/adchoices

If you're a 90s kid like Jason, you probably grew up with Tetris. But not like Maya Rogers grew up with Tetris. Her dad brought the game from the  Soviet Union to the rest of the world. Now Maya runs the brand herself, and the job is trickier than it sounds. How do you honor something people feel deeply nostalgic about while also making sure a seven-year-old in 2026 cares about it too? Maya joins...

How do you find your first customers? It’s a question first-time founders are often flummoxed by. But Keith Krach has developed a tried-and-true strategy—starting during his days at Ariba (which sold for billions), and extending into his current time as chairman of Docusign. In this special live edition of Problem Solvers, taped at Entrepreneur Live in 2018, Keith explains how to turn a company’s...

It's a noisy world. If you want to succeed, you must learn to stand out — or to become, as Jason calls it, "singular." In this episode, he offers a formula for increasing your value: Instead of relying on your expertise or quality of products alone, you must combine that expertise with a well-communicated unique perspective. Here’s how to become the only person people think of when they need what...

It's the 450th episode. Okay, it's actually the 451st. But close enough. Every 50 episodes, Jason steps back and reflects on the show: how it's changed, why it's changed, and what he's learned from making it. And this time, he shares the formula for why it’s changed over the years. Learn more about your ad choices. Visit megaphone.fm/adchoices

Danielle Sepsy started developing her secret scone recipe at 13. That recipe built The Hungry Gnome. But to grow, she had to share it with her team, and eventually with the world in her new book, The Scone Queen Bakes. So how do you scale a secret without losing your edge? Danielle figured it out. And this week, she's telling us how. Learn more about your ad choices. Visit megaphone.fm/adchoices

What if the secret to winning in business isn't competing better? What if it's competing less? That's the idea behind category creation. And this week, Jason is speaking with Kevin Maney, co-author of The Category Creation Formula , to break down exactly how it works. Kevin lays out a simple but powerful formula for creating and owning your category. Drawing on real-world examples ranging from the...

Everyone says to “build your personal brand,” but how do you actually do that on LinkedIn? In this episode, Jason talks with Laura Lorenzetti, Senior Director and Executive Editor at LinkedIn News, about what really works and what doesn’t. They walk through how to create content that sparks conversation and build a repeatable strategy for growing your personal brand. Along the way, they bust some...

Today, Jason is sharing something different and special. His wife, Jennifer Miller, has a new podcast — a true-crime story about mistaken identity, impossible choices, and one man who goes to prison for his twin brother's crime. It's called Blood Will Tell. Here, you'll find the first episode. You can find the rest by subscribing to Blood Will Tell wherever you listen to Problem Solvers. Learn mor...

Melissa Bernstein co-founded Melissa & Doug and built it into a billion-dollar children's toy company. Along the way, she learned a lot about entrepreneurship, which she shares in her new book The Heart of Entrepreneurship. Today, for the first time publicly, she shares the three-part strategy she used to fight back and what happened the moment new ownership stopped following it. Learn more ab...

Every entrepreneur has been told to push through, stay the course, and that grit is everything. But advice like that leaves out that some of the smartest, most successful people in business got there by quitting at exactly the right moment. So how do you know when that moment is? Dr. Anthony Klotz, organizational psychologist and author of Jolted , has spent years studying exactly this question. H...

Kevin Smith went from making art to being the art and learned the hard way that when you become the product, there's no off switch. In this episode, Smith breaks down how he's stayed relevant for 30 years by treating fans like the bosses they actually are. Plus: Jason shares how he once convinced his college to spend their full year's speaker budget just to get Kevin Smith on campus and what happe...

Joey Zwillinger, the founder of Allbirds and Biologica, sat down with Jason to talk about the challenges of finding your ideal customer. Joey's done it both ways. Starting with a product and searching for the right people to buy it, and starting with a problem and building the solution. In this conversation, he breaks down what actually works when you're hunting for product-market fit, and what to...

Nobody likes meetings. But there’s a good reason for that. Organizational behavior expert Dr. Rebecca Hinds, author of the new book Your Best Meeting Ever , explains why most meetings are a massive waste of time and what to do about it. She shares a simple test to determine if a meeting actually deserves to be on your calendar. Plus, Jason also discovers something uncomfortable about his own appro...

For sole proprietors and self-employed professionals, taxes can feel confusing, time-consuming, and easy to get wrong. What counts as a deduction? How do you save money on your taxes? And how do you stay organized when you’re doing everything yourself? In this episode, CPA and tax expert with TurboTax, Lisa Greene-Lewis breaks down how solo business owners can make taxes simpler, smarter, and less...

Gary Vaynerchuk joins Jason to share why he believes traditional social media is fading and where smart businesses should focus next. He explains how to find the audience you’re overlooking, and offers a practical framework for getting your content in front of the right people in 2026. Plus, why one of his agencies is rebranding and what it signals about where marketing is headed. Learn more about...

Moments Lab co-founders and identical twins, Frederic & Philippe Petitpont, realized they were in the wrong role. The CEO became CTO. The CTO became CEO. As a result, the business got stronger. In this episode, they break down how to spot role misalignment and how putting the company first can unlock real scale. Learn more about your ad choices. Visit megaphone.fm/adchoices