Stupid Questions with Seth Hill

Seth Hill

Asking smart people stupid questions.

  1. Aug 10

    #234 - James Cunnama: Identity, Mental Health, and Finding Your Way Back

    James Cunnama is a former professional triathlete who finished top 5 in Kona, won Challenge Roth, and made a career of endurance. But his real story isn’t about race results—it’s about who he became after crossing the finish line. In this raw and honest conversation, James opens up about losing his identity when he retired from pro sport, struggling with suicidal thoughts, and learning that presence matters more than podiums. We discuss his coaching philosophy on removing friction to enable passion, why small daily improvements compound into life transformation, and how fatherhood forced him to answer the hardest question: Who am I? James also shares his last day working at GTN after five years, what his kids have taught him about what really matters, and why you can't help others until you're willing to reach out for help yourself. This is a conversation about mental health, purpose, family, and the often-invisible struggle behind someone who looks like they have it all figured out.James’ IG: https://www.instagram.com/jamescunnama/James’ Coaching: www.kiscoaching.com/inquiry Suicide Prevention Hotlines – Worldwide USA: 988 Suicide & Crisis Lifeline (call or text 988, 24/7) BelleUSA (Crisis Text): Text HOME to 741741 (24/7) caCanada: 988 Suicide Crisis Helpline (24/7) BelleUK: Samaritans – 0800 689 5652 or 0800 689 0880 (24/7) Find a HelplineAustralia: Lifeline – 13 11 14 (24-hour) SamaritansNew Zealand: Lifeline – 0800 543 354 or text 4357 (7am–midnight) Mental Health FoundationNew Zealand (Samaritans): 0800 72 66 66 (24/7) Lifeline-internationalIndia: KIRAN – 1800-599-0019 (24/7) Find a HelplineSouth Africa: 0514445691 HealthcollectiveFrance: 3114 (24/7) Psychology TodayGermany: Telefon Seelsorge (online chat 4pm–11pm CET) Suicide StopSpain: 914590050 Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #234 - James Cunnama: Identity, Mental Health, and Finding Your Way Back
  2. Aug 3

    #233 - Jeremiah Bishop: What 30 Years of Racing Taught Him About Fathers, Failure, and Perspective


    Jeremiah Bishop has spent over 30 years racing bikes at the highest level — national titles, ultra-endurance expeditions, and the Impossible Route, a documentary series he created that's racked up millions of views chasing unfinishable rides across deserts most people would never attempt. He just turned 50, and instead of slowing down, he won every race he entered this season. In this conversation, Jeremiah and I get into what three decades of racing all over the world actually taught him — not about training, but about perspective: how differently the world looks depending on who's telling the story, what he learned about America from wearing the national team jersey abroad, and why he's become wary of curated narratives, whether from a broker, a news network, or his own competitive ego. We also talk about fatherhood, growing up without his own dad from age four, and how a mother battling addiction shaped both his drive and his eventual peace with her. Jeremiah opens up about chasing validation through competition for most of his career, and the slow work of learning that fulfillment has to come from execution, not outcome. We close on stoicism, fear as "the mind killer," and his honest answer to what it would mean to have lived a fulfilled life. This one goes deep — from bike racing and media literacy to grief, mentorship, and what it actually means to make peace with the past. Jeremiah’s IG: https://www.instagram.com/jeremiahbishoprides/?hl=enWays to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #233 - Jeremiah Bishop: What 30 Years of Racing Taught Him About Fathers, Failure, and Perspective

  3. Jul 27

    #232 - Mango Fetzer: Sailing the Atlantic, Surviving a Home Invasion & the Wisdom of Dream Big

    Mango Fetzer is Luke Fetzer's mom — and one of the most vibrant, well-lived humans I've ever had the privilege of talking to. She's spent a decade sailing across oceans, worked as a private chef around the world, survived a beaten-bound-and-bagged home invasion in Panama, and taught her kids to see life as a gift, every single day, no matter what. This conversation went places I didn't expect. Mango talks about looking a masked intruder in the eyes and telling him to look at her before he pulled the trigger. She talks about coping with PTSD through Heart Math breathing techniques and cracking Australian stock whips with an old cowboy neighbor. We get into her decade sailing the Atlantic — the doldrums, the Cape Verde Islands, a retired naval captain who couldn't tolerate the smell of curry, waking up to bioluminescent dolphins outside Antigua at night. We also talk about her mother's final moments, watching the sunrise clouds burst as she passed, the ginkgo tree Luke planted in the front yard the day they bought their Laguna Beach home, and why she believes the more people you tell your dreams to, the more likely they are to actually happen. This one is a masterclass in living wide open. Bring tissues. Bring wonder. Mango’s IG: https://www.instagram.com/mangomama_laguna/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #232 - Mango Fetzer: Sailing the Atlantic, Surviving a Home Invasion & the Wisdom of Dream Big
  4. Jul 20

    #231 - Elliott Teller: The Founder of People's Endurance on China Manufacturing, Fatherhood & Building Freedom to Build

    Elliott Teller is the founder of People's Endurance — a cycling and running apparel company built on a simple bet: that quality doesn't have to come with a brand tax. He's also a former director of photography, a tech sales guy turned entrepreneur, a new dad, and someone who spent his first two years running the business on virtually no sleep while juggling APAC hours, a newborn, and a wife going back to work with barely any paid leave. Elliott sits down with me to talk about leaving the film industry after watching too many burned-out, divorced veterans warn him off it, his seven years in tech sales that started with a week-long trial run and an air mattress in a buddy's home office, and the wild timing of quitting his job the same week his wife found out she was pregnant. We get into the actual mechanics of the apparel industry — dyed versus sublimated fabrics, why manufacturing still has to happen in Asia, and the privateer model he's building to let athletes sponsor themselves instead of chasing brand deals that rarely pay. We also go deep on parenting, mitochondria and longevity, the small daily decisions that keep your internal compass tuned, and why he thinks bigger brands are starting to quietly copy his playbook. This one's for anyone building something from scratch while also trying to keep a tiny human alive. Elliot’s IG: https://www.instagram.com/elliottteller/ Peoples Endurance: https://peoplesendurance.com/?srsltid=AfmBOoqdKCZePjXPrPHD2cFVtQoHzb_sdGdXt_7TVGSqs6tEJot2rw-8Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #231 - Elliott Teller: The Founder of People's Endurance on China Manufacturing, Fatherhood & Building Freedom to Build
  5. Jul 6

    #230 - Andrew Vos: The Dad Who Broke a Guinness World Record (and Realized Family Matters More Than Success)

    Andrew Vos is a husband, father of two, endurance athlete, entrepreneur, and former Guinness World Record holder for the fastest mile while pushing a stroller. But this conversation isn't really about the world record—it's about the life behind it. Andrew shares how becoming a dad completely changed his priorities, why he no longer cares what other people think, and how his definition of success shifted from chasing titles and promotions to walking his boys to school every morning. We talk about growing up in small-town Wisconsin, getting cut from a Division I running team, finding a home in Division III, discovering triathlon at 34, and the hilarious story of breaking a Guinness World Record during COVID while his kids blasted fart noises through his headphones. We also dive into navigating ulcerative colitis while training, building businesses that create freedom instead of just income, raising resilient kids without overprotecting them, balancing ambition with family, and why the best legacy you can leave isn't a résumé—it's children who know they were seen, loved, and supported. This is a conversation about fatherhood, purpose, endurance, and the quiet success that often matters most. Andrew’s IG: https://www.instagram.com/andrew.vos_tri/ Wild & Free Hats: https://www.instagram.com/wild_and_free_hats/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #230 - Andrew Vos: The Dad Who Broke a Guinness World Record (and Realized Family Matters More Than Success)
  6. Jun 28

    #229 - Alex Wormuth: The Software Engineer Building an AI Triathlon Coach Nobody Else Had the Nerve to Build

    Alex Wormuth is a software engineer, dad of two, and the founder of Transition — an AI-powered triathlon training platform he built in his nights and weekends because the existing tools weren't quite right for triathletes, and because he had a hunch that large language models could actually coach people pretty well. Turns out he was right. Alex sits down with me to talk about growing up in Riverside, traveling solo through Europe and Nepal straight out of college, living in Guangzhou during the early days of COVID, and how all of that shaped the way he thinks about building things and understanding people. We get into the parallels between entrepreneurship and travel — the risk tolerance, the discomfort, the not knowing what's around the corner — and why his dad letting him climb 30 feet up a tree at five years old probably had something to do with it. We also go deep on AI. What it's actually doing to software engineering right now, why the jobs most at risk aren't the ones people think, what the real value of a human coach still is, and why the companies best positioned to get disrupted are the ones most afraid to disrupt themselves. And somewhere in the middle of all that, we talked about whether a paper data center is a viable business idea. I think it might be. Try Transition free for 30 days: transition.fun Search "Transition Triathlon" on the App Store Transition IG: https://www.instagram.com/transitiontriathlonWays to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #229 - Alex Wormuth: The Software Engineer Building an AI Triathlon Coach Nobody Else Had the Nerve to Build
  7. Jun 22

    #228 - Round 4 - Ari Klau: Round Four on Mindfulness, the Post-Mustache Era & Losing His Sister

    Ari Klau is back for round four — and this one goes places we haven't gone before. Fresh off a second-place finish at Chattanooga and building toward what may be the best season of his career, Ari sits down with me to talk about what's actually changed and what hasn't. We get into the mindfulness practice he picked up at a swim camp earlier this year and how it's quietly become the biggest performance differentiator in his racing. We talk about what it actually feels like to finally podium after years of grinding — and why it didn't feel the way he thought it would. We go deep on the tyranny of the mind, trusting external structure over internal impulse, and the philosophy of doing things you don't want to do as the real definition of self-care. We also talk about the mustache. It's gone. Apparently, two high-level team managers had written him off as not serious because of it. His dad saw photos from Chattanooga and said he looks formidable now. The results seem to agree. And then at the end, Ari shares something he's never talked about on here before — losing his sister in 2021, how it launched him into professional triathlon, and what it's like to still be processing that while also being the son who keeps forgetting to call on his dad's birthday. It's the same day as his late sister's birthday. It's a lot to carry. Ari’s YT: https://www.youtube.com/@archmdz Ari’s IG: https://www.instagram.com/archmdz/?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

    #228 - Round 4 - Ari Klau: Round Four on Mindfulness, the Post-Mustache Era & Losing His Sister
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Asking smart people stupid questions.

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