What if generosity wasn’t something you waited to “earn”, but something you practiced the moment you could?

This week Shawn catches up with the founder of Fans First Entertainment and the wildly original mind behind the Savannah Bananas, Jesse Cole, to unpack a powerful Shawnism: “If I can afford it for me, I can for others.” Not just financially, but in spirit, effort, and intention.

Shawn and Jesse explore why giving things away often brings more in return, why Jesse refuses to focus on competition, and how long-term fans always beat short-term profits. The two also share why generosity has nothing to do with money and everything to do with how you show up, why the best creators build what they genuinely love, and the philosophical difference between chasing a billion fans and chasing a billion-dollar valuation.

Whether you’re building a brand, a team, or a community, this episode proves that generosity isn’t a cost, it’s the strategy.

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It’s a new year, and Shawn is flying solo.

In the very first solo episode of Let Me Save You 25 Years, Shawn tackles a question that feels heavier than ever: Why does everything feel broken? And more importantly… how do you live well anyway?

Shawn unpacks his honest answer, and shares the mindset shifts that help him stay grounded, hopeful, and purposeful when things feel overwhelming. He also reflects on the same two New Year’s resolutions he makes every year, how personal agency may be the most valuable skill you can develop today, and why time, not money, is the ultimate currency.

This episode isn’t about fixing the whole world. It’s about leaving your small, meaningful bit of light in it, and choosing to live well anyway.

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What if everything you do actually matters? Every choice. Every habit. Every moment you think is small.

This week Shawn catches up with entrepreneur, wellness educator, and champion of MTV’s The Challenge, Emily Schromm, to unpack one deceptively simple idea: "Everything Matters."

From the butterfly effect of daily decisions to the hidden cost of running life on autopilot, Shawn and Emily explore how intentionality shapes who we become and what we build. They also discuss the importance of being present, managing your finite energy wisely, and how impulsivity can be intentional when you’re aware.

Everything changes when you realize everything matters.

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What if the secret to great ideas is just trying things on, noticing what fits, and letting go of what doesn’t?

This week Shawn sits down with digital creator, entrepreneur, and creative force, Rebecca Zamolo, to dive deep into the Shawnism: “Try Things On.”

Shawn and Rebecca dig into how failure can ironically build confidence, why you should never attach your self-worth to a single creation, and how we’re all (yes, even successful adults) still playing dress-up in one way or another. The two also discuss how to gather feedback without losing yourself, why mental flexibility is a superpower, and how trying on ideas, identities, and even roles can unlock clarity, creativity, and confidence.

If you’ve been stuck on one idea, one role, or one identity… this episode is your guide to try something new on and see what fits.

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It’s never too late to chase the dream that won’t leave you alone.

This week Shawn sits down with the hilariously talented Kate Flannery, beloved as Meredith from The Office, to break down the Shawnism: "It’s Never Too Late."

Kate and Shawn discuss why the right dream is the one you’ll fight for, the importance of finding small things to love even in the jobs that aren’t “the one,” and the quiet superpower of being pleasantly persistent. They also tackle how to protect your journey, avoid comparison traps, and balance ambition with real life. Plus, Kate reveals one surprising life lesson Meredith taught her.

And as Meredith would say, maybe not in words, but definitely in spirit: You’re allowed to fall down. Just make sure you fall forward toward the thing you want.

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Greatness often begins when you’re ready to do the unglamorous, grinding, foundational work most people avoid.

Going back into the vault for this week, Shawn brings on three-time Olympic gold medalist, and one of the most dominant action-sports athletes in history, Shaun White, to discuss the Shawnism: “Be willing to sweep floors.”

The two dig into what it really takes to rise: working with what you’ve got (even if you didn’t grow up on a mountain), choosing humility over ego, and recognizing that no one gets anywhere alone. Shaun also shares how relationships, grit, and an unwavering willingness to do the hard, unglamorous work shaped every victory.

This episode teaches us all about ambition, and why sweeping floors might just be your ultimate competitive advantage.

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You can plan, prepare, and strategize, but some lessons only reveal themselves once you jump.

This week Shawn sits down with the powerhouse sisters behind The Elf on the Shelf, Chanda Bell and Christa Pitts, to explore the truth behind the Shawnism: “You Can’t Know What You Don’t Know.”

Shawn, Chanda, and Christa dig into the value of knowing the worth of your idea, the evolution of vision, and why authenticity, paired with the courage to adapt, is the magic ingredient behind lasting success. Chanda and Christa also share how a simple family tradition grew into a global phenomenon, and how much of that journey required learning on the fly, trusting their instincts, and moving forward before they had all the answers.

This is an episode for anyone staring down a new beginning. Go for it. The learning will meet you on the path.

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Sometimes the smartest move isn’t to fight harder… it’s to step back and fight better.

This week Shawn catches up with actress, dancer, designer, and creative powerhouse, Megan Batoon, for a deep, refreshingly honest conversation about what it really means to lose the battle to win the war.

The two discuss how messy and consistent action can save you when perfection can’t, the importance of recognizing the fights that drain you versus the ones that actually move you forward, and why quitting isn’t always a failure, sometimes it’s just an intermission.

If you’ve ever wrestled with whether to pivot, pause, or press on, this chat will give you the clarity to choose the battles that actually help you win the war.

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