Problem Solvers

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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Executive Coach Neal Schore says that fear-driven habits are quietly
stealing at least an hour from your day, every day. Drawing from
decades of coaching founders, operators, and unicorn CEOs, Neal explains
how anxiety about being fired, judged by boards, or seen as “not
enough” leads to endless Slack chains, diluted meetings, and mental
“swirls” that crush focus and time. Neal and Entrepreneur
Editor in Chief Jason Feifer unpack why good things often start with
worst-case scenarios (like getting fired), how to stop overcompensating
out of fear, and why managing you—not everyone else—is the only
way to reclaim your calendar. He shares practical tools from his new book, The 25th Hour, like the “clarifying question” that can turn a 7-hour crisis into a 7-minute conversation, the devil/angel metaphor for fear versus real performance issues, and a simple five-minute “swirl limit” to stop catastrophic thinking from hijacking your nights and weekends. If you’re a founder or senior leader stuck in loss-aversion, overcommitting to boards, or living in constant “what if I get fired?” mode, this conversation shows
you how to get out of your own way, protect your time, and even see job
loss or client churn as the start of better fits—not the end of your
career.
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Tom Szaky built TerraCycle into a recycling giant, then decided recycling wasn't good enough. His new venture, Loop, aimed to replace disposable packaging with reusable containers for brands like Tide and Häagen-Dazs. Consumers loved it. Retailers loved it. So why did it nearly die in four out of five test markets? Szaky breaks down the hidden flaw that almost killed Loop, and the simple insight that finally made it scale.
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Here's a number that should stop you: 11,000 pairs of jeans, sold in 36 hours, from one video posted by a customer with just 5,000 followers. That's the end result of years of work by Brieane Olson, CEO of Pacsun, who decided her brand needed to stop talking at its customers and start building with them. In this episode, Olson shares strategies from her new book, Co-Created, and what she thinks most companies get wrong about "community" in the first place.
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Leadership expert Ryan Hawk tackles one of the biggest traps for ambitious entrepreneurs: dabbling in everything and committing to nothing. Ryan unpacks the idea of “beefing up your obituary” by becoming the kind of person people remember for deep work and sustained excellence—not half-finished projects.If you’ve been spreading yourself thin across side hustles, content platforms, and random opportunities, this conversation will help you identify your “one main thing,” build an ecosystem around it, and know when you’re still just coasting versus when it’s time to dive. Check out Ryan's new book, The Price of Becoming.
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