Stupid Questions with Seth Hill

Seth Hill
  • 4.7 (20)
  • Society & Culture
  • Updated Biweekly

Asking smart people stupid questions.

  1. 6d ago

    #238 - Tegan Phillips: The Cartoonist Who Learned to Run a Business

    Tegan Phillips is a South African cartoonist, adventure writer, and creator known for her women's cycling comedy — and for riding 11,000 kilometers across Africa with her family. But her real story isn't the big adventures. It's the quieter, less glamorous choice to stay put and build something sustainable when running away would have looked braver. We talk about growing up in Cape Town and what inequality teaches a kid early, the boxes families and social media put us in, the eating disorders and comparison that shaped her teenage years, what it took to learn how to be honest in a friendship, and the gap between her chaotic online persona and the methodical business owner behind it. She opens up about the book she's been dragging her feet on for five years, and shares the most practical advice we've had on the show: if you want to make a living from your art, you have to learn how business actually works. This is a conversation about the difference between following your heart and running from discomfort — and how hard it is to tell them apart without time alone to figure out which voice is which. Tegan’s IG: https://www.instagram.com/teganphillipscomics/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #238 - Tegan Phillips: The Cartoonist Who Learned to Run a Business

  2. Aug 31

    Episode #237 - Mike Reilly: The Voice of IRONMAN on Finding Your Finish Line Beyond the Race

    Mike Reilly is the legendary voice of IRONMAN finish lines—the man who has called thousands of athletes across the finish line with four iconic words: "You are an Iron Man." But after decades of defining his life around announcing races and chasing the next event, Mike grapples with what it means to step away from the role that made him a household name in endurance sports. His real story isn't about the accomplishments or the voice—it's about learning, finally, where his actual finish lines really are. We talk about his parents' example of perseverance without preaching, what it truly means to be yourself in public, why sharing your goals with loved ones changes everything, the cost of missing anniversaries and birthdays for races, finding balance across mental, emotional, physical, and spiritual dimensions, staying sharp as you age, caregiving when you can't fix what's broken, and why your real finish lines aren't at races. Mike also opens up about his second book—a 15-month project that taught him more about writing and purpose than he expected—and why stepping away from Ironman felt like crossing the finish line he'd been training for all along. This is a conversation about finding your real finish line when the world has already built a monument to a different one. It's about presence over performance, legacy over accolades, and learning that what you do every day at home matters infinitely more than any achievement on a stage. Mike’s Book - Finding your Finishline: https://www.amazon.com/dp/B0HFG73C6H Mike’s IG: https://www.instagram.com/ironmanvoice/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    Episode #237 - Mike Reilly: The Voice of IRONMAN on Finding Your Finish Line Beyond the Race

  3. Aug 24

    #236 - John Mollura: Respond, Don't React

    John Mollura spent 15 years leading mission-critical field testing for NASA and elite US military units. But his real gift—the ability to read people and see exactly what makes them tick—nearly destroyed everything. This is the story of how he learned to wield that power as a tool for connection instead of control, and what it cost him to get there. We talk about the moment a spiritual awakening forced him to see himself clearly, how he went from using emotional intelligence as a weapon to wielding it as a leader, and the painstaking work of separating your self-worth from your performance. John shares practical wisdom on the Enneagram, the difference between reacting and responding, why discretion is harder to develop than competence, and the quiet courage it takes to let the people you love struggle and figure things out on their own. Whether you're an athlete grappling with identity beyond sport, a leader trying to hold people accountable with grace, or someone trying to break reactive patterns that have shaped your entire life, John's journey offers both the challenge and the blueprint for transformation. John’s LinkedIn: https://www.linkedin.com/in/john-mollura/John’s Site: https://johnmollura.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

    #236 - John Mollura: Respond, Don't React

  4. Aug 17

    #235 - Peter Stetina: From World Tour to Gravel, Finding Your Why

    Peter Stetina is a professional gravel racer, former World Tour cyclist, father of twins, and one of the early architects of modern professional gravel racing. In this conversation, we dive deep into his career transition from the pressure-cooker of European road cycling to the emerging gravel scene—and what that journey taught him about identity, sacrifice, and what actually matters. We talk about the cost of making your body your job, the realization that comes when you're forced to let go of the dream you've chased since childhood, becoming a parent mid-career, the people who stick around when things get hard, and why "a happy racer is a fast racer" might be the most important lesson he's learned in 20 years as a professional athlete. This is a conversation about transitions, perspective, and finding peace in a life spent chasing something bigger than yourself. Peter’s IG: https://www.instagram.com/pstetina/ Ways to Support the Show👇🏼 Nothing Novel: https://nothingnovel.life  Socks: https://stupidquestions.show/pages/sq-merch  Newsletter: ⁠https://stupidquestions.show/pages/newsletter-signup

    #235 - Peter Stetina: From World Tour to Gravel, Finding Your Why

  5. 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

  6. 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


  7. 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

  8. 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
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