Stupid Questions with Seth Hill

Seth Hill

Asking smart people stupid questions.

  1. #213 - Sean Leader: Outdoor Life, Entrepreneurship, and Doing the Work

    HACE 6 DÍAS

    #213 - Sean Leader: Outdoor Life, Entrepreneurship, and Doing the Work

    I sit down with trail builder, entrepreneur, and former professional downhill mountain biker Sean Leder to talk about the life he’s built around the outdoors. Growing up in East Tennessee, Sean turned his passion for riding into real businesses, helping launch Windrock Bike Park and founding Southern Gravity, a trail-building company shaping some of the best terrain in the Southeast. We talk about building a business in a niche sport, the lessons he learned watching his parents grow a company from their basement, and why he prioritizes freedom and time outside over chasing money. Sean also shares insights on patience, leadership, navigating difficult clients, building teams, and the discipline required to keep pushing forward when things break — both literally and figuratively — along with reflections on fatherhood, relationships, entrepreneurship, and living a life defined by more than just one pursuit. Sean’s IG: https://www.instagram.com/seanleader/?hl=en Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1 h y 20 min
  2. #212 - Annie Fuller: When Triathlon Saved My Relationship With Food

    2 MAR

    #212 - Annie Fuller: When Triathlon Saved My Relationship With Food

    I sit down with professional triathlete Annie Fuller, a member of the Real Tri Squad, to talk about her journey from collegiate running at Michigan State to racing in the professional triathlon scene. Annie opens up about the injuries that have shaped much of her career and the mindset it takes to keep showing up when things don’t go as planned. We talk about the difference between loving training and loving racing, and why she considers herself a racer at heart. We also dive into her past struggles with fueling and body image in endurance sports, and how triathlon ultimately helped transform her relationship with food. Along the way, we talk about family influence, community in triathlon, trusting the process, faith, and why Annie doesn’t want to be “the next” anyone else — she just wants to be the best version of herself. Annie’s IG: https://www.instagram.com/annie_fuller/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    1 h
  3. #211 - Dave Barnes, Musician, Singer, and Songwriter — Joy, Autonomy, Faith & The Real Cost of Chasing Success

    23 FEB

    #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

    1 h y 22 min
  4. #210 - Custodio Toldeo - From Startup Exit to Le Mans: How I Met a Ferrari Race Car Driver

    16 FEB

    #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

    1 h y 8 min
  5. #209 - Harry Talbot, Professional Cycling Photographer - Creativity & Never Being Satisfied

    9 FEB

    #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

    1 h y 12 min
  6. #208 - Robbie Deckard, Professional Triathlete - Identity, Aging, and When the Dream Starts to Change

    2 FEB

    #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

    1 h y 28 min
  7. #207 - Round 2 - Skye Moench: Becoming a Mom Changed Everything (and Brought Peace Back)

    26 ENE

    #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

    1 h y 6 min
  8. #206 - Round 2 - Morgan Pearson, Olympian - From Burnout to Belief: Morgan’s 2026 Blueprint

    19 ENE

    #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

    1 h y 10 min
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