Most businesses that resist change die. But Jake Shivery refused to give up analog photography and turned his Portland shop, Blue Moon Camera and Machine, into a thriving 26-person business.  But to keep his mission alive, Jake had to embrace changes he never wanted, from digitizing film to building a social media presence. In this episode, he shares how to balance stubborn focus with strategic flexibility and what every entrepreneur can learn about surviving disruption.

This episode is brought to you by CLA. With you on every step of your financial journey. To learn more, visit CLAConnect.com.

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Branding expert Laura Ries joins Jason to talk about her new book, The Strategic Enemy , and the power of positioning. Together, they break down how companies can define what they stand against, win customers, and become the go-to name in their category. This is a packed conversation about how to create campaigns that resonate and understand the strategy behind the marketing that shapes our world.

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What do you do when your company is running out of money, your industry has collapsed, and even you think your idea is dumb? That’s the situation Siqi Chen, now founder and CEO of the finance platform Runway, faced in 2016 when he became CEO of Sandbox, a VR startup. Yet through a bold move, Chen managed to get the right people to believe, securing funding for a product that was a stupid good time. 

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Search is changing. Instead of typing a few words into Google, clients are now asking AI tools for hyper-specific recommendations. So how do you make sure they still find you? In this episode, Max DesMarais of Vital Design shares how to position your business so large language models present you as the solution to your client's problem.

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Marcus Lemonis built his reputation as the guy who could fix anything. It’s even in the name of his TV show The Fixer on FOX his new show following the success of The Profit on CNBC. But now, as he enters a new phase of leadership, he’s rethinking what it really means to lead. Lemonis has evolved. He’s leading from behind, pushing people harder than they’d push themselves, and even playing the villain if that’s what the business needs. 

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 Michael Jacobson joined his uncle’s flower shop to help close it down.  Instead, he uncovered industry-wide problems like outdated tech, inefficient supply chains, and reliance on costly middlemen. By solving them one by one, he grew the French Florist into a thriving franchise that’s redefining the floral business.

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The myth of the genius jerk founder has shaped startup culture for decades, but it’s wrong. Dr. Richard Hagberg and Tien Tzuo, co-authors of Founders Keepers, have the data to prove it. In this episode, they unpack the real traits that define high-performing founders, why bad behavior gets glorified, and how emotional intelligence and adaptability, not arrogance, drive lasting success.

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Julia Hartz is the co-founder and CEO of Eventbrite, the platform built to help anyone host and sell tickets to an event. But after years in the business, Julia and her team realized something surprising. Their biggest growth opportunity wasn’t with the people creating events, it was with the people searching for them. On this episode, Julia shares how Eventbrite rethought its product, reimagined discovery, and why, in an AI-saturated world, real human connection might just be the ultimate value proposition.

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 Ania Smith, CEO of TaskRabbit, has spent her career building marketplace businesses. She shares the operational challenges of matching people who need tasks done with people who can do them and how TaskRabbit solves for the millions of unpredictable human variables that come with it. Balancing supply and demand at scale means identifying the patterns and solving the problems.

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Eynat Guez, co-founder and CEO of Papaya Global, shares how a single contract clause nearly bankrupted her first company and why confronting that worst-case scenario changed everything. Instead of panicking, she mapped out the fallout, turned it into leverage, and negotiated a way out. That mindset became a repeatable leadership strategy, helping her build a $3 billion global payroll platform while navigating both personal and professional risk.

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