Problem Solvers

Latest Episodes:

Are You Over-Managing Your Team? Nov 03, 2025

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Executive coach Muriel Wilkins joins the show to unpack one of the biggest growth blockers in business. The leader who needs to be involved in everything. Drawing from her new book Leadership Unblocked, she breaks down how that urge forms, why it destroys trust and agency inside organizations, and how to recalibrate your time toward the work that actually drives results.

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Taylor Rooks on How to Instantly Connect With Anyone Oct 27, 2025

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NBA stars don’t open up easily, but Taylor Rooks makes it look effortless. The lead host of Amazon’s NBA on Prime joins the show to share how she earns trust fast, even from the most guarded people in the room. It’s not just about asking questions. Whether you’re interviewing the team or leading it, trust is the foundation of every successful relationship.

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Michael Bosstick on How to Build and Leverage an Audience Oct 20, 2025

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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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How to Take a Long Vacation Oct 13, 2025

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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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Everything You Know About Leadership Is Wrong Oct 06, 2025

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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 He reveals why most leadership advice is outdated, how the entire industry is built on a con man’s research from the 1900s, and what actually drives people to follow great leaders.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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Uncover Hidden Value for Customers, with Alibaba.com's President Sep 29, 2025

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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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How to Change Without Losing Yourself Sep 22, 2025

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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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Win Customers’ Attention with This Clever Strategy Sep 15, 2025

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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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How Not to Die as a Company Sep 08, 2025

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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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How to Get AI to Recommend You Sep 01, 2025

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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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