Problem Solvers

Jason sits down with Sebastian Wernicke, data scientist and author of Data Inspired: Building an Organizational Culture of Inquiry for Lasting Transformation, to talk about why "data-driven" companies so often end up trapped inside what they already know instead of discovering what their customers actually need. They get into the sports car company that ignored its own sales numbers, the one question that reveals whether your company can actually handle being wrong, and how Jason's own newsletter taught him he'd built himself a very comfortable cage.

Timestamps

0:00 The Hit Song Formula That Failed

0:27 Welcome to Problem Solvers

0:38 Why a Song About Pop Music Matters to Your Business

2:45 Meet Sebastian Wernicke, Author of Data Inspired

3:06 Why Data Feels Like Comfort (And Why That's a Trap)

4:52 Two Ways to Use Data: Optimization vs. Innovation

5:06 Google's "50 Shades of Blue" Experiment

6:38 Data-Driven vs. Data-Inspired, Defined

7:46 The Sports Car Company's Weird Stereo

10:25 How Do You Know Which Outlier to Trust?

13:19 Use Data to Support a Bold Guiding Policy, Not a Safe One

14:20 The Medical Device Company's Real Diagnosis

16:29 Jason's Own Data Trap: A/B Testing His Newsletter

20:59 Error Reduction vs. Loss Aversion

22:24 Can a Junior Analyst Challenge the Boss in Your Company?

26:03 The Book: Data Inspired
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Before he was Deep Pocket Monster, Pat Flynn was the face behind Smart Passive Income. Eighteen years later, he's ready to pour everything into Pokémon, but he's not willing to abandon the community that built him. So he made a call most founders never make. Liz Wilcox, an email marketing expert with her own exit story, joins him to explain what happens next.
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A few years ago, Jason rediscovered his love of Pop-A-Shot, the arcade basketball game. What he didn't know was the whole story behind Pop-A-Shot's sudden renaissance. Tony Stucker, the CEO of Pop-A-Shot, joined the show to unpack the brand strategy behind the turnaround and what it takes to extract new growth from a legacy asset.
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Jason once got an edit back covered in red, all caps, like he'd been screamed at on paper. He swore he'd never do that to anyone, but it turns out most of us are still getting feedback wrong. Caroline Webb, author of Leadership Intelligence, breaks down the one shift that makes people actually hear you. It's simpler than you think, and it starts with what you say before the criticism..

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Will AI make entrepreneurship easier—or make entrepreneurs irrelevant?In this episode of Problem Solvers, Jason Feifer sits down with LinkedIn Chief Economic Opportunity Officer Aneesh Raman, co-author of Open to Work: How to Get Ahead in the Age of AI, to rethink the biggest fear around AI and business: that technology is coming for your job, your company, and your edge.Jason shares his “AI is a microwave” theory: it’s a powerful new tool, but we’re still learning what belongs in it—and what absolutely doesn’t. Aneesh explains why AI is lowering the cost of starting a business, making it easier to research markets, build prototypes, and test ideas fast. But as access goes up, so does the premium on something AI cannot replicate: your unique perspective, taste, curiosity, courage, communication, and lived experience.They break down why the future of work is not about humans becoming better AI prompters. It’s about becoming more entrepreneurial, more creative, and more distinctly human. In a world flooded with AI-generated sameness and “AI slop,” the people who win will be the ones who use AI to amplify—not replace—their judgment, originality, and connection.
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