Stupid Questions with Seth Hill

Seth Hill

Asking smart people stupid questions.

  1. #211 - Dave Barnes, Musician, Singer, and Songwriter — Joy, Autonomy, Faith & The Real Cost of Chasing Success

    1D AGO

    #211 - Dave Barnes, Musician, Singer, and Songwriter — Joy, Autonomy, Faith & The Real Cost of Chasing Success

    I sit down with singer-songwriter, comedian, podcaster, and all-around storyteller Dave Barnes for a conversation that goes way deeper than music. We talk about what it really means to chase success without losing your family, how autonomy shapes the choices we make, and why joy might actually be a powerful force — not just a feeling. Dave opens up about faith, fatherhood, the changing music industry, the pressure to provide, and the tension between ambition and contentment. We also get into creativity, performing, entrepreneurship (or not), and the quiet question so many of us carry: Did I choose the right path? Dave’s IG: https://www.instagram.com/p/DUhOpeTDOAR/ Dave’s Tours (Website): https://www.davebarnes.com Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 22m
  2. #210 - Custodio Toldeo - From Startup Exit to Le Mans: How I Met a Ferrari Race Car Driver

    FEB 16

    #210 - Custodio Toldeo - From Startup Exit to Le Mans: How I Met a Ferrari Race Car Driver

    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/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 8m
  3. #209 - Harry Talbot, Professional Cycling Photographer - Creativity & Never Being Satisfied

    FEB 9

    #209 - Harry Talbot, Professional Cycling Photographer - Creativity & Never Being Satisfied

    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/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 12m
  4. #208 - Robbie Deckard, Professional Triathlete - Identity, Aging, and When the Dream Starts to Change

    FEB 2

    #208 - Robbie Deckard, Professional Triathlete - Identity, Aging, and When the Dream Starts to Change

    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/ Ways to Support the Show: Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 28m
  5. #207 - Round 2 - Skye Moench: Becoming a Mom Changed Everything (and Brought Peace Back)

    JAN 26

    #207 - Round 2 - Skye Moench: Becoming a Mom Changed Everything (and Brought Peace Back)

    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/ Ways to Support the Show: Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 6m
  6. #206 - Round 2 - Morgan Pearson, Olympian - From Burnout to Belief: Morgan’s 2026 Blueprint

    JAN 19

    #206 - Round 2 - Morgan Pearson, Olympian - From Burnout to Belief: Morgan’s 2026 Blueprint

    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/ Ways to Support the Show: Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1h 10m
  7. #205 - Seth Hill, What 200 Conversations Taught Me About Who We Are

    12/18/2025

    #205 - Seth Hill, What 200 Conversations Taught Me About Who We Are

    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. Ways to Support the Show: Nothing Novel: https://nothingnovel.life Socks: https://stupidquestions.show/pages/sq-merch Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup⁠

    41 min
  8. #204 - Lisa Bourgoyne, CEO of The Landing - Where Sexual Abuse Meets Hope: Inside the Work of The Landing

    12/15/2025

    #204 - Lisa Bourgoyne, CEO of The Landing - Where Sexual Abuse Meets Hope: Inside the Work of The Landing

    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/ Support the Pod: ⁠https://stupidquestions.show/pages/sq-merch⁠  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup⁠

    1h 10m
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4.7
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