What if it works? It’s a simple question, but it can completely change the way you approach your life.

This week Shawn sits down with actor, father, and recent Masked Singer finalist, Scott Porter, to unpack the mindset that has shaped Scott’s career: stop obsessing over what could go wrong and start asking what might happen if you simply say yes.

Scott shares how one unexpected beatboxing opportunity became a lightning strike for his career, why his mom’s advice that “worry is a useless emotion” still sticks with him, and why dependability and work ethic are two things nobody can take away from you.

Shawn and Scott also discuss why “What if it works?” doesn’t have to mean changing your life overnight. Sometimes it means making a little progress, learning a lesson, or avoiding a mistake. Oh, and Shawn finally gets an answer to the very important question: Is Kyle Chandler really that cool?

If you’ve ever talked yourself out of an opportunity because you were too busy worrying about what could go wrong, this episode might make you rethink your entire approach. Because what if it works?

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Why is America getting sicker while spending more and more on healthcare?

Shawn Nelson sits down with Justin Mares, CEO and Co-Founder of Truemed, to unpack what Justin believes is fundamentally broken about the American healthcare system, from commercial incentives and regulatory capture to a system that may be rewarding the wrong outcomes.

But this conversation goes way beyond healthcare. Justin explains why obsessing over a problem might be one of the clearest signs you’re meant to solve it, why finding an assignment worthy of your life makes prioritization dramatically easier, and why commitment can actually create freedom.

They also get into why “flexible” spending accounts aren’t very flexible, three things Justin recommends cutting from your diet, and why the best problem solvers don’t just complain about what’s broken, they go looking for something worth fixing.

And at the heart of it all is this episode’s Shawnism: Understand the Assignment. Because before you try to win, make sure you actually understand what success looks like.

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“Chase No’s. Get to Yes.”

That’s the Shawnism at the heart of this conversation between Shawn and Scott Harrison, the former New York nightclub promoter who became the founder of charity: water.

Scott went from getting people to spend money on drinks in New York to witnessing children drinking from swamps in Liberia, an experience that completely changed his perspective on money, purpose, and his life. Today, he’s raised billions to fund more than 216,000 clean-water projects worldwide. But the bigger lesson may be about money itself: why does more almost never feel like enough?

Shawn and Scott dive into the power of asking, the one fundraising meeting Scott has never forgotten, and why clean water is a solvable problem, if we simply have the will to solve it. They also explore why we’re so afraid of “no,” when to compromise versus standing your ground, and how the fear of being perceived the wrong way can lead us away from what actually matters.

Chase the no. Ask bigger. Get to yes.

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What if your “failed” idea wasn’t bad, it was just too early?

This week Shawn sits down with Leah Solivan, founder of TaskRabbit AND self-taught chicken farmer, for a founder-to-founder conversation about the Shawnism, “Match the Moment.”

Shawn and Leah trade stories about the times they moved too early, waited too long, or realized the market simply wasn’t ready. They dig into why the right strategy at the wrong time can be the wrong move, how constraints can actually unlock creativity, and whether great founders predict the future, or just notice it a little sooner.

They also get into AI, building infrastructure for chaos, cross-training your brain, and why Leah’s chickens might be doing more for her entrepreneurial brain than another business meeting ever could.

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Sometimes the safety nets we think are protecting us are actually the things holding us back.

In this incredible replay from last year, Shawn sits down with actor, writer, and producer, David Dastmalchian, and the timing couldn’t be better! Since this conversation was recorded, David has landed one of his biggest roles yet: the main villain, M. Bison, in the new Street Fighter movie, hitting theaters October 16.

David opens up about walking away from the destructive crutches that once controlled his life, burning the life-raft, and discovering that “safe” can sometimes be nothing more than an illusion.

From his idea of a “holy pause” to the messages and messengers that show up when you finally let go, this conversation is about taking the leap, embracing uncertainty, and discovering who you are when there’s no way back.

Sometimes, the only way forward… is to ditch the safety net.

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What do you get when two cousins, a drunken idea, and a heated game of NHL ’94 collide? Somehow, a national lobster empire.

Shawn sits down with Jim Tselikis and Sabin Lomac, the cousins behind the Shark Tank success story Cousins Maine Lobster, to uncover what really happened between that first crazy idea and the 95 food trucks they have today, and why the hardest part of building a business may be surviving long enough to see it work.

Jim and Sabin reveal the four-year turning point that changed everything, why chasing overnight success can actually be a trap, and the hockey advice Jim still lives by today. They also unpack the surprising power of empathy, why franchisees are brought to Maine as a rite of passage, and how they protect a brand when their reputation is literally riding on someone else’s truck.

Plus: the personality test that changed how these cousins work together, the one thing they wish they’d done sooner, and the one thing that will sink a Shark Tank pitch quicker than anything.

It takes years. The trick is knowing what to do with them.

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What if being called crazy was proof you were onto something?

This week Shawn sits down with 4Ocean CEO Alex Schulze to unpack how two surfers with a crazy idea, a stack of $1 bills, and almost no roadmap built a company that has now removed nearly 55 million pounds of trash from oceans and waterways.

Alex goes back to the surfing trip that changed everything, the staggering amount of plastic entering our oceans every day, and the early days when 4Ocean had to be scrappy, resourceful, and willing to figure it out later. Shawn and Alex talk about pressure creating authenticity, how to turn an overwhelming problem into one small action, and why you should learn to love the “field days.”

They also get into planned obsolescence, sustainable storytelling, how Alex’s health battles almost derailed 4Ocean’s mission, and the unexpected way one of Shawn’s toughest moments led him to buy a boat.

The lesson: You don’t need the whole plan. You just need the guts to start.

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What if the life you worked so hard to build isn’t actually the life you want anymore? And what if that nagging feeling that “something is missing” isn’t a crisis, it’s a signal?

This Shawn sits down with entrepreneur, author, coach, and creator of The Midlife Male, Greg Scheinman, to tackle “We Aren’t Building a Piano” and why progress, not perfection, is the real game.

They get into the uncomfortable truth that sometimes the problem with success isn’t your drive… it’s the goal you’re driving toward. Greg explains why your calendar may reveal your priorities better than you do, how falling out of sync with your own “operating system” can quietly derail your life, and why midlife might be the perfect time to stop, reassess, and reinvent.

Maybe reinventing yourself doesn’t require blowing up your life. Maybe it means making better choices, getting back to the basics, and realizing something Shawn and Greg both know pretty well: we aren’t building a piano.

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