Michael Bosstick, founder and CEO of Dear Media, breaks down the mechanics of audience growth and what smart creators do after they’ve built one. He shares his proven blueprint for turning attention into impact. This conversation will change how you think about the audience as an asset, not just a metric.

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Most people think taking a month off work is impossible, but what if it’s actually a smart career move? Jillian Johnsrud, author of Retire Often, argues that planning a “mini-retirement” isn’t just good for your sanity. It forces you (and your company) to build better systems, and delegate more effectively. In this episode, Jason digs into her framework for making extended time off possible in any situation.

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Jon Levy, behavioral scientist and author of Team Intelligence, is here to blow up what you thought you knew about leading teams. He reveals why most leadership advice is outdated, how the entire industry is built on a con man’s research from the 1900s, and what actually drives people to follow great leaders. He also shares one scientifically proven tip to build a smarter team.

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Entrepreneurs face two kinds of problems: One has clear answers, the other does not. But is it possible to take unclear paths... and make them clearer? Alibaba.com president Kuo Zhang joins the show to talk about Accio, the company’s new AI tool that helps entrepreneurs create products, and the larger business lesson it represents.

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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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