I sit down with Ferrari GT3 driver Custodio Toledo, whose journey into professional racing started not on the track but in business — after building and selling a software company, a spontaneous Ferrari purchase ultimately led him to compete in legendary endurance races like Le Mans and Daytona. We talk about the physical and mental demands of motorsport, how his business background shaped his approach to racing, and his perspective on luck, discipline, and surrounding yourself with the right people. We also dive into family, faith, purpose, and what it means to reinvent yourself later in life — a conversation about chasing goals, staying curious, and proving it’s never too late to pursue what once felt out of reach.

Follow Custodio’s IG: https://www.instagram.com/custatoledo/

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In this episode, I sit down with world-tour cycling photographer Harry Talbot to talk about life behind the lens — from shooting races like the Tour de France and living out of suitcases to chasing creative excellence without losing yourself in the process. Harry shares what it’s really like working inside professional cycling, the chaos most people never see, and what it takes to consistently create photos that make people stop and look twice. We get into identity, ambition, travel, nature, self-doubt, and the tension between wanting more while still trying to stay grounded. Harry opens up about the constant push to improve, the fear of losing that drive, and how creativity, career, and personal fulfillment all intertwine. This one’s about purpose, perspective, and figuring out what it actually means to love what you do while still becoming who you’re meant to be.

Follow Harry’s IG: https://www.instagram.com/visualsofharry/

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Robbie Deckard is a professional triathlete, coach, and someone I’ve gotten to know well over the last few years through shared training blocks, Tucson winters, and long conversations about sport and life. In this episode, we talk about everything from mustaches and dogs to Olympic dreams, burnout, self-coaching, and the quiet identity shifts that happen when you realize a decade has passed faster than you expected.

We dig into what it’s like to dedicate your life to endurance sport without the financial security people assume comes with being “pro,” how curiosity can both elevate and derail performance, and why so many athletes struggle when it’s time to let a version of themselves go. Robbie opens up about aging, purpose, family, writing a book, and what it means to build a life around being outside rather than chasing a single result.
Robbie’s SubStack: https://substack.com/@robbiedeckard?r=2d6gzd&utm_medium=ios&utm_source=profile&shareImageVariant=light

Robbie’s IG: https://www.instagram.com/robbie_deckard/

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I sat down with Skye Munch for a second time—now as a mom to 14-month-old Lois—to talk about how motherhood has completely reshaped her identity, priorities, and relationship with triathlon. We get into the realities no one prepares you for: ongoing sleep deprivation, the emotional weight of childcare decisions, and why chasing peace mattered more than chasing fitness or results this past year.

Skye opens up about sponsorship pressure, social media identity shifts, and what it was really like making it back to Kona as a new mom. Selfishly, I asked a lot of questions as my wife Ashley and I prepare to welcome our daughter Noelle—covering practical advice for new parents, what actually helps postpartum, and why the internet often makes things harder, not easier.

Skye’s IG: https://www.instagram.com/skyemoench/

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Season 3 kicks off with a round-two conversation with Olympic medalist Morgan Pearson—this time digging into what it really takes to reset after a long year. Morgan shares how travel, burnout, and injuries tested him, why “process goals” and small habits matter more than hype, and what changed in his training that brought his confidence back. We also get into the tension of racing the best vs. chasing easier wins, what he wishes sponsors understood, and how he thinks about grief, identity, and continuing to show up when motivation wobbles.

Morgan’s IG: https://www.instagram.com/morgan_cadwell_pearson/

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This episode is different.

To close out the season, Seth steps out from behind the questions and reflects on what he’s learned from nearly 100 conversations with athletes, founders, musicians, and high performers from all walks of life.

After analyzing every transcript from the past year, Seth shares 10 core through-lines that kept showing up—identity, suffering, faith, high performance, mental health, community, and the quiet tension between who we are and what we do.

He opens up about losing his father, becoming a husband and soon-to-be father, pornography recovery, burnout, ambition, and the ongoing work of becoming someone he’s proud of. This episode explores the real cost of chasing excellence, why “making it” rarely feels the way we expect, and why who you are when no one’s watching matters more than any résumé.

The second half of the episode gets deeply personal—vision for the future of the show, lessons from building Stupid Questions over years of false starts, and why curiosity, truth, and heart have to stay at the center of everything.

This isn’t a recap.

It’s a reflection.

And an invitation to ask better questions of yourself.

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In this deeply personal and unexpectedly vulnerable episode, I sit down with Lisa Burgoyne, CEO of The Landing—a Houston-based nonprofit serving survivors of human trafficking and commercial sexual exploitation through trauma-informed, Christ-centered care. Lisa’s decades of experience in child advocacy, counseling, and frontline anti-trafficking work give her a perspective that is both sobering and full of hope.

What begins as a conversation about her life and mission becomes something more. As Lisa opens up about the realities survivors face—trauma, homelessness, addiction, broken family systems—I find myself drawn into sharing parts of my own story, wrestling aloud with trust, childhood wounds, and the long, messy process of healing. Together, we talk through why sexual abuse persists, how pornography and unchecked appetites fuel exploitation, why so many victims go unseen, and what it takes to rebuild a life after trauma.

Lisa brings clarity, compassion, and wisdom to an issue most people avoid because it feels too dark to face. She also offers practical insight into recognizing secondary trauma, the cost of leading in this space, and how faith and community make this work sustainable.

Whether you’ve experienced trauma, love someone who has, or simply want to understand the world more honestly, this conversation will likely hit deeper than expected. And if you feel moved to support Lisa’s work, visit thelanding.org—even a small act can make a real impact.

Lisa’s IG: https://www.instagram.com/lisabourgoyne/

The Landing: https://thelanding.org

The Landing IG: https://www.instagram.com/thelanding_hou/

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In this episode, I sit down with South African-born athlete, coach, and entrepreneur Natasha van der Merwe—a woman whose life has spanned pro tennis, professional triathlon, coaching at the highest level, and now leading a 23-coach organization at NVDM Coaching.

We go deep into the stories behind her leadership, her faith, and the experiences that shaped her—including losing her father at 15, navigating the pressures of elite sport, rebuilding her confidence through motherhood, and learning to show vulnerability without losing strength.

Natasha opens up about what it means to steward a calling, how she balances ambition with faith, why relationships are the core of great coaching, and the challenges of raising a daughter while running a rapidly expanding business.

This conversation is layered, emotional, and rich with perspective—from identity and grief, to entrepreneurship, to parenting and the future of triathlon. Whether you're an athlete, a leader, a parent, or someone figuring out who you’re becoming, Natasha’s story will leave you thinking long after it's over.

Natasha’s IG: https://www.instagram.com/natashavdm81/

NVDM Coaching IG: https://www.instagram.com/nvdmcoaching/

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