Harry Talbot is a New Zealand-born World Tour cycling photographer based in Girona, Spain, whose second photo book just sold out a 900-copy run. But this conversation isn't really about the shots. It's about a self-described control freak who's comfortable for the first time, and isn't sure that's a good thing.We talk about air-freighting three tons of books to beat Christmas, spending a whole season chasing a window as good as his cracked-glass shot of Pogačar, the night in Rome when he lost his card reader and missed Oakley's podium deadline, why he still won't forgive himself for it, why he struggles to trust anyone with his business, his dream of a physical gallery, and his honest take on faith, luck, and the 99 percent he credits to hard work.This is a conversation about control, and what it might take to let a little of it go.Harry IG: https://www.instagram.com/visualsofharry/Ways to Support the Show👇🏼Newsletter: https://stupidquestions.show/pages/newsletter-signup

André Abreu is a Portuguese-born domestic elite cyclist and the founder of Oak, a bike company he runs out of his garage in Boise, Idaho. But his real story isn't carbon frames. It's about a man who spent years chasing certainty and proving people wrong, and is finally learning that letting go takes its own kind of discipline.

We talk about the $250K fixie shop in Tempe that ran out of money by the time he was 21 and nearly broke his relationship with his dad, the camper van he built to live in Iceland and never drove, meeting his wife on Instagram and getting locked down together two weeks later, the two years he let her carry them while he chased a YouTube-and-sponsorship pro dream, deconstructing and rebuilding his faith, and why he's at peace with Oak's first bikes arriving months late.

This is a conversation about humility, the kind that usually shows up after you've hit the floor, and what changes when a four-hour ride becomes a two-hour ride and that's okay.

André IG: https://www.instagram.com/oakracing/

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Robbie Deckard is a pro triathlete and longtime coach who has spent years chasing aero gains, first to keep up with Rudy von Berg on training rides and now through his company, Freaky Fast. But this conversation isn’t really about watts. It’s about what happens when a garage obsession turns into a real business, and the person behind it has to grow up with it.

We talk about molding his first monobar from heat-moldable plastic and watching Canyon release almost the same design a week later, teaching himself CAD from a $16 online course at 3 a.m., the 50-plus prototypes behind his first product, reinvesting every dollar while racing toward break-even, why a single broken part makes him want to “punch a wall and cry,” giving away aero advice he probably should charge for, and still chasing Kona and a sub-8 Ironman after a four-month Achilles injury.

This is a conversation about building something you’d want to buy yourself, and learning to care deeply without letting every setback become a verdict on who you are.

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

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Parker Spencer is a USA Triathlon coach who leads Project Podium, the federation's donor-funded men's elite program, while finishing a PhD in exercise science and coaching pros like Sam Long. But his real story isn't the World Cup podiums. It's about a coach who once told his wife he was done, and who has come to believe that faith in his athletes matters more than any number on a lab report.

We talk about rewriting 120 pages of his dissertation when he thought he was at the finish line, why he wants his athletes to see him as a friend and still know when "Coach Parker" shows up, the busyness he calls his biggest weakness and the 16-mile mountain run that resets him, being two years into the USAT job, buried in critics and ready to quit, why he believes success is winning and wants his athletes to carry an ego, and a practical breakdown of VO2 max, VLA max, and why he's moved away from traditional periodization.

This is a conversation about leading people toward something hard, and why the most powerful thing a coach can say might be "I believe in you."

Parket’s IG: https://www.instagram.com/coachparkerspencer_/

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Luke Tasker is a full-time Vancouver firefighter, a former Team GB modern pentathlete, and one of the newest names in pro triathlon. He won Ironman Victoria in his debut and took fifth at IRONMAN 70.3 NorCal against a stacked field. But his real story isn't about how fast he's climbed. It's about a man who knows exactly what he's living for, and isn't shy about saying it.

We talk about leaving the UK for one ski season and never going back, and the 59 days he spent on a four-man rowing boat around Britain. He shares the psychologist's exercise that kept that crew from falling apart. He opens up about a father he's no longer close to but refuses to resent, and about why he tells his best friend he loves him. We also get into the 12 seconds that cost him a Worlds slot, and his unapologetic atheism, which leads to a candid, respectful back-and-forth on faith, meaning, and what happens when it's all over.

This is a conversation about conviction: what it looks like to build a life around love and family when you believe this one is all you get, and what two people who see the world very differently can learn just by listening.

Luke’s IG: https://www.instagram.com/taskertri/

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Cole Kynoch is a first-year professional triathlete racing for Roka Standard Racing and an after-sales area manager for Lamborghini's Americas region — one of the more unusual day-job-and-side-hustle combinations on the pro circuit. But his real story isn't about supercars or race splits; it's about a self-described "jack of all trades, master of none" learning, later than he'd like, that figuring everything out alone isn't the same as thriving.

We talk about what pushed him to turn pro after years of finishing races alone off the front of the amateur field, how growing up as the oldest with twin younger sisters shaped his instinct toward self-sufficiency, why asking for help still doesn't come naturally to him, what mutual respect and loyalty mean to him as guiding principles, his path from Volkswagen to Lamborghini and what climbing that corporate ladder actually looks like, and his evolving, agnostic relationship with faith — including why he walked away from a checklist version of religion in favor of just trying to live with integrity.

This is a conversation about the quiet cost of always being the one who figures it out — in sport, at work, and in marriage — and what changes when you finally let people, and maybe something bigger than yourself, in.

I've saved this one (episode number, title, description, and a few candidate takeaways) so it's ready whenever you build the next newsletter — even if that's a different session down the road.

Cole’s IG: https://www.instagram.com/cole_tries_tris/

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Benjamin Randall — known to most of the internet as Triathlete Benny — is a professional triathlete and a staff writer at Colorado State University. But his real story isn't the run splits people argue about in the comments; it's the shy only child who just wanted friends, and the years he spent training close to 40 hours a week trying to outrun something he couldn't name. What he's built since is less about fitness than about finally being a whole person.

We talk about being labeled "just a runner who does triathlon," the strange math of having your worth measured in three sports, the high school journalism teacher who lit the fire that still drives his writing, and the coaches who found him at his lowest and asked what he was actually doing. Ben opens up about his eating disorder and the inpatient treatment that followed, grapples honestly with what recovery looks like when your sport rewards the same obsessiveness that nearly broke you, and shares the mental reframe that pulled him out of black-or-white thinking — plus why shoving his watch in his pocket made him faster.

This is a conversation about what happens when you stop performing your identity and start living it. If who you are depends entirely on what you did last Saturday, what's left on the days you don't race?

Benny’s IG: https://www.instagram.com/triathletebenny/

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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/

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