Why Most Founders Can't Grow Past 25 Employees

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

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

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

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

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 phone lines, what Burger King has actually done with everything it heard, and how the brand spent four years quietly rebuilding before it ever asked customers to come back. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 Jason to break down the strategy, including one surprisingly powerful legal move that keeps anyone from just copying the game and calling it something else. Learn more about your ad choices. Visit megaphone.fm/adchoices

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 first customers into valuable ambassadors. Learn more about your ad choices. Visit megaphone.fm/adchoices

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