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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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/

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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/

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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/

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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=en
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