How Success Happens

Entrepreneur Media
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Jan 28, 2026 • 36min

How He Turned $78 Into a $250 Million T-Shirt Empire

Bert Jacobs built Life Is Good with his brother, a beat-up van, and $78. He explains how positivity became a competitive advantage and why giving back was never optional. The Playmakers nonprofit grew alongside the brand and sits at the core of its “why.” Bert also shares his belief in capitalism and business as the only way to save the world. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 25, 2026 • 11min

Snack Break: Jimmy Humilde

Music producer Jimmy Humilde is added another title to his résumé with his new film, Clika. Even as he becomes a true multi-hyphenate, he shares practical advice on managing nerves and staying grounded through gratitude. Plus an unconventional approach to meditation. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 21, 2026 • 39min

How Does Wrestling Anacondas Save the World?

Growing up, Paul Rosolie thought all the great adventures were already taken. Until he traveled to the Amazon and realized just how much of the world is still waiting to be explored. His journey into the rainforest inspired him to co-found Junglekeepers, a nonprofit dedicated to saving the Amazon and, by extension, the rest of us. In this episode, Paul breaks down how a killer hook and a carefully structured story can get your brand message across. Turns out, wrestling anacondas is optional, but it definitely helps people pay attention. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 18, 2026 • 13min

Snack Break: Fantasy Football

Joel Milton, co-founder of Splash Sports, has made it easy for anyone to run a contest with friends or fans. But running the company itself is much harder. In this snack-size episode, Joel talks about building a business when the rules keep changing, how to avoid chasing shiny ideas, and why getting something out into the world matters more than getting it perfect. Plus, Dan responds to the comment section. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 14, 2026 • 38min

Bert Kreischer Gets Ambushed by Guy Fieri

No matter how you measure it, Bert Kreischer is a success. And yet, the fear never really goes away. In this conversation, the stand-up comic, podcasting powerhouse and star of the new Netflix series Free Bert, talks about imposter syndrome and what actually drives his relentless work ethic. He shares his formula for telling a great story and explains why the most awkward celebrity interactions often make the best ones. Plus, Guy Fieri drops in to ask Bert a few questions of his own. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 11, 2026 • 14min

Snack Break: Healing

At 32, Alex Bussenger was at the top of his game and senior vice president at Bank of America. Then an aortic dissection nearly killed him. He survived, but recovery brought something he didn’t expect. A  deep sense of loneliness. In this snack-size episode, Alex shares how that experience led him to create Heal Together, an app that connects people recovering from major health events with others who’ve been there. Because healing isn’t just physical and no one should have to do it alone. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 7, 2026 • 27min

Cowboy Kent Rollins’ Guide to Success

Cowboy Kent has cooked meals on the open range and gone head-to-head with Bobby Flay and beaten him. But his success didn’t stop in the kitchen. He’s built a thriving YouTube channel, a successful catering business, and written cookbooks. In this episode, Kent shares why faith and family aren’t just part of his story, but the foundation of everything he’s built. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jan 4, 2026 • 12min

Snack Break: Coffee time

Sahand Dilmaghani is the founder and CEO of Terra Kaffe, who happens to make Dan’s current favorite coffee machine. Sahand recently joined Dan for a webinar, and this snack break serves up some of Dan’s favorite insights from that conversation. They talk about slowing down when things get chaotic, the best advice he’s gotten, and how knocking on doors with early prototypes helped turn an idea into a real business. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Dec 31, 2025 • 19min

Snack Break: Antarctica Explorer

It’s time to pull out your New Year's party horns. Instead of resolutions, Dan kicks off the year with a pep talk from Colin O’Brady, the first person to walk across Antarctica completely alone and unsupported. They talk about pushing past limits, facing fear, and what dragging a sled across the ice has to do with building something hard from scratch. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Dec 28, 2025 • 14min

Snack Break: Mike Rowe

In this Snack Break, Dan digs back into the archives for a conversation with Dirty Jobs host Mike Rowe. They talk about purpose, and why having a “why” matters to his entrepreneurial journey. Plus, Mike tells an unforgettable story about poop. Learn more about your ad choices. Visit megaphone.fm/adchoices

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