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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What if a three-word text sign-off between friends became a $35 million business, and a movement millions of dads now call their own?

This week, Shawn sits down with Grant Eastey, co-founder of Dad Gang, for a conversation about putting your passion into the world, staying relentlessly authentic, and why sometimes the thing you almost don't send is the thing that changes everything. Grant shares how a simple text thread became a business, why staying “un-corporatized” helped Dad Gang grow, and how they built an organic safe space for dads at a time when so many men are struggling to find real community.

Shawn and Grant also get into the modern dad crisis: why new fathers often lack meaningful support, why men can struggle to ask for help, how changing expectations are reshaping fatherhood, and why dads need to stay connected when life gets hard. Plus, they get into the surprisingly simple trick to becoming more visible: ask for advice.

Because your art can't impact anyone if you never put it out there. Let them see you.

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What do you do when the very thing that made you famous... starts to disappear?

This week, Shawn sits down with comedian, actor, and America's Got Talent “Golden Buzzer” winner, Drew Lynch, for a conversation that starts with comedy but quickly becomes a masterclass in resilience, reinvention, and why perspective changes everything. After an accident left Drew with a stutter, he built an entire career around the very thing that changed his life. But what happens when you begin overcoming the challenge that made you famous?

Shawn and Drew dive into why the opportunities you never planned for are often the ones worth chasing, how to build self-worth in a career where you are the product, the hidden cost of living for external validation, and why awareness may be one of the most valuable skills you can develop. They also explore why you'll never become your best self if you think you've already arrived.

By the end of the conversation, Shawn realizes the original Shawnism wasn't quite right. Maybe perspective doesn't just change everything... maybe perspective is everything.

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What if the secret to building a bigger business isn't taking more... but giving more?

This week, Shawn sits down with Masami Sato, founder of B1G1, for a conversation about one of the most counterintuitive ideas in business: Give to Get.

Masami shares how she built a global movement helping companies turn everyday transactions into meaningful acts of impact, and why business at its best exists to give. Shawn and Masami break down the counterintuitive idea that giving can actually be one of the smartest business strategies, why profit and purpose don't have to compete, and how small acts of generosity, multiplied across millions of people, can create massive change.

They also discuss how self-interest can be leveraged for good, why giving what you need can somehow come back around, and the two things every person can give that cost absolutely nothing.

At the end of the day giving isn't just a nice thing to do, it's a competitive advantage.

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What if the biggest breakthroughs in your life don't come from thinking bigger... but from paying closer attention to the details right in front of you?

This week, Shawn sits down with Ronnen Harary, co-founder of Spin Master, the company behind PAW Patrol, Kinetic Sand, and countless other household favorites, for a conversation about why sometimes you have to Zoom In to Zoom Out.

Ronnen shares why business is driven more by intuition than spreadsheets, how a learning disability became one of his greatest strengths, and why ignoring the thing you're meant to do may be the biggest risk of all. He and Shawn also discuss the hidden cost of constantly calculating risk, why you should never outsource your own equity, and they answer the hilarious question of whether the man behind some of the world's most beloved toys has ever actually finished a puzzle.

This episode is a great reminder that the people who see the biggest picture usually start by noticing what everyone else overlooks.

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What if losing everything was the best thing that ever happened to you?

This week, Shawn sits down with entrepreneur, bestselling author, and former CEO of the sports agency that inspired Jerry Maguire, David Meltzer, for a conversation about one simple idea: "The best time to plant an oak tree was 25 years ago... the next best time is today."

David shares the hard-earned lessons he learned after making and losing a fortune, why your self-image sets the ceiling for your success, and how the meaning you assign to your mistakes can shape the rest of your life.

Shawn and David also dive into the key difference between knowledge and wisdom, what it really means to be happy, why asking for help is one of the greatest shortcuts to success, and some of the key ways to staying humble if you’re in an industry that embraces ego and pride.

Because no matter where you are today, it's never too late to plant a better seed. And the one you plant today could change everything tomorrow.

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