Taking Chances - Why not you?

John OBrien
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  • FITNESS

Bold moves, big dreams, and the people who made them happen. In this podcast, we uncover the stories of those who bet on themselves—why they did it, how they pushed through, and what it took to turn risk into reward. Feeling the itch to chase your own dream? Start that podcast. Write that book. Take the leap. ✅ Want to share your story with me, send me an email at: Johnobie2468@gmail.com #takingchances #whynotyou #leadville #lt100 #mentalhealth #Running #hokaoneone #tailwindnutrition #dontquit #hardwork #determination #discipline #motivation #ultrarunning #family #therapy #mentalhealthawareness #training #selflove #selfcare

  1. Taking Chances - Why not you? Year end 2025

    18/12/2025

    Taking Chances - Why not you? Year end 2025

    2025 Year-End Recap: Taking Chances - Why Not You?What a remarkable year it's been for Taking Chances - Why Not You?! In 2025, we dropped 34 powerful episodes, each one a testament to the core message: bold moves, big dreams, and the courage to ask, "Why not me?"This year, we brought you an incredible lineup of guests who embody resilience, determination, and the art of betting on themselves. From the worlds of elite athletics to business and everyday heroism, our conversations highlighted what it truly takes to push limits while navigating real life.Highlights from Our Extraordinary Guests:Pro Athletes and Combat Legends: We sat down with UFC Hall of Famer Pat Miletich, diving into the mindset of a fighter who redefined grit in the octagon. Ultra-Endurance Warriors: Stories from Ultra Running Champions, Backyard Ultra winners, Leadville Trail 100 finishers, and national record holders inspired us all to go further. A standout was Episode 19 with Phil Young – owner of Fleet Feet Davenport (one of America's top running stores) and holder of the 4th fastest 100-mile time in U.S. history. His blend of business savvy and blistering trail speed reminded us that excellence isn't limited to one arena. Olympic-Level Achievers: Gold Medalists shared the sacrifices and triumphs behind standing on the podium. (Andy Yohe) Business Titans: Leaders like Beth Jannery (Founder of Titan Strategic Communications) opened up about strategic risks, authentic leadership, and building legacies that impact industries. Ordinary People Doing Amazing Things: The heart of our show shone through in episodes with everyday heroes – folks crushing massive goals while juggling demanding jobs, families, and life's curveballs. Transformations like Evan Kilstrom's journey to engineering and endurance, or Brian Doerfeld's reinvention through fitness and coaching, proved that extraordinary results start with everyday courage. Across these 34 episodes, recurring themes emerged: mental health in high-stakes pursuits, balancing ambition with family, overcoming adversity, and the sheer power of discipline and self-belief. Whether it was tales from the trails of Tunnel Hill, the intensity of HYROX training, or rebuilding after setbacks, every guest left us with actionable inspiration. Thank you to our incredible guests for trusting us with your stories, and a massive shoutout to you – our listeners – for tuning in, sharing episodes, and taking your own chances. Your messages and feedback have fueled this journey. As we close out 2025, remember: Start that podcast. Write that book. Take the leap. Why not you? Here's to an even bolder 2026. Keep taking chances!– Your host, John O'Brien #TakingChances #WhyNotYou #UltraRunning #MentalHealth #GritAndGratitude

    35 min
  2. Taking Chances - Scott Anderson - THE SCOTT BOYS

    08/12/2025

    Taking Chances - Scott Anderson - THE SCOTT BOYS

    🎙️ S. Scott Anderson Scott Anderson is a lifelong storyteller whose journey blends journalism, executive leadership, and a passion for history. An avid reader, student of the past, and global traveler, Anderson draws on real-world experiences to bring depth and authenticity to his characters and narratives. Though his career path took him from journalism into the world of construction equipment, writing and photography have always been his true constants. Now retired, he devotes his energy to exploring automotive history, crafting creative fiction, and weaving historically inspired tales that are as unique as they are compelling. Rooted in Tennessee, where his family has lived since the early 1700s, Anderson remains a voyager at heart—always seeking new horizons and opportunities. You’re most likely to spot him at historic car gatherings, tucked away in small vineyards, or immersed in history shows, continuing his lifelong pursuit of stories worth telling. Amazon: https://www.amazon.com/Scott-Boys-Novel-Inspired-Actual/dp/1663273553 Barnes & Noble: https://www.barnesandnoble.com/w/the-scott-boys-s-scott-anderson/1147711487 iUniverse: https://www.iuniverse.com/en/bookstore/bookdetails/863188-the-scott-boys website: sscottanderson.com FaceBook: https://www.facebook.com/p/The-Scott-Boys-61567869444996/ : https://www.facebook.com/p/S-Scott-Anderson-Author-61578488477061/ Linkedin: https://www.linkedin.com/in/s-scott-anderson-590391a3/

    1h 17m
  3. Taking Chances - Solo #3

    03/12/2025

    Taking Chances - Solo #3

    🎙️ Podcast "Welcome back to Taking Chances – Why Not You? I’m your host, John O’Brien, and today we’re diving into solo episode number three. Recently, I listened to Ken Rideout’s new podcast where Rich Roll was his guest, and it got me thinking. People are often drawn to stories of those who’ve overcome addiction—whether it’s drugs, alcohol, or food—because those journeys are raw, powerful, and inspiring. But what about the rest of us? The so-called ‘ordinary’ people who’ve faced extraordinary challenges and still found a way forward? For me, 2001 was that year. I lost my mom, lost my job, and got married—all within months. Three massive life events, two of them devastating, one of them life changing. And somehow, I survived. I found a way. That’s what this podcast is becoming: a space to celebrate resilience, grit, and the everyday heroes who refuse to quit. Ordinary people doing extraordinary things—not because it was easy, but because they chose to find a way. So let’s get started. This is Taking Chances – Why Not You? Episode three."

    18 min
  4. Taking Chances - John O'Brien - "Finding a way"

    01/12/2025

    Taking Chances - John O'Brien - "Finding a way"

    Just me, solo, recapping an episode and then realizing that this Podcast highlights people who end up being able to FIND A WAY to get shit done! It's that simple. ordinary people doing extraordinary things, accomplishing amazing things, balancing it all and FINDING A WAY TO GET IT DONE!

    9 min
  5. Taking Chances - Bella & Kathryn Miletich

    24/11/2025

    Taking Chances - Bella & Kathryn Miletich

    🎙️ Taking Chances – Why Not You? Episode Title: “Sisters in the Arena: Bella & Kathryn Miletich” Today’s episode is a masterclass in grit, discipline, and sisterhood. I’m joined by two powerhouse women who are no strangers to pushing limits—Bella and Kathryn Miletich. Daughters of UFC Hall of Famer and world champion Pat Miletich and the incredible Lynne Miletich, these sisters are carving their own endurance legacy—one mile, one stroke, one finish line at a time. Bella just crushed her second marathon—the Enders YMCA Harrisburg Marathon—in 3:41. That’s impressive on its own. But she did it while juggling grad school, coaching a college swim team, working part-time, and training solo in New Jersey. No training group. No hype squad. Just pure self-motivation and a whole lot of heart. A former Lane 4 swimmer turned collegiate rower at Jacksonville University, Bella’s now chasing her master’s with the same intensity she once brought to the pool. And then there’s Kathryn. A 2022 Bettendorf High School grad and 15-year Lane 4 swimmer, she just completed her first Ironman—yes, Ironman Florida—in 12 hours and 18 minutes, with a blistering 59-minute swim. She’s studying Finance at FAU and graduates this December, but she’s already investing in something far more valuable: her own potential. We talked about what it takes to balance training, school, work, and life. We got into nutrition, motivation, and what keeps them going when no one’s watching. And spoiler alert—they’re just getting started. So if you’ve ever wondered how to fit big dreams into a packed schedule—or how to turn family legacy into personal fuel—this one’s for you. Let’s go.

    1h 18m
  6. Taking Chances - Craig Burns

    10/11/2025

    Taking Chances - Craig Burns

    🎙️ Welcome back to Taking Chances, the podcast where we celebrate bold moves, unexpected turns, and the stories that shape us. Today’s guest is someone who knows a thing or two about carving his own path—Craig Burns. Before we dive into Craig’s journey, let me give you a little context. He just turned 60 years old. He grew up in Peabody, Massachusetts on Beacon St, where his childhood was all about motion—running around the neighborhood, playing 4 square, chasing games, chasing friendships, and chasing every Boston sports team on TV. Hockey stole his heart early, and it still holds it tight. School was a challenge—not because he didn’t care, but because he couldn’t sit still. He was more interested in connecting with people than cracking textbooks. After high school, he took a shot at the machinist apprenticeship at General Electric in Lynn. Graduated in ’89—and got laid off the same day. That moment was a wake-up call. He knew he had to pivot. So he went back to school, starting at community college to fill in the gaps, and eventually found himself at UMass Lowell studying Exercise Physiology. But his curiosity didn’t stop there—He dove into Psychology, Philosophy, History, and Religious Studies. He was painting houses to pay the bills, staying active with running, biking, and hockey, and slowly realizing that the traditional path wasn’t for him. After a brief return to GE, He TOOK A CHANCE and turned his side hustle into his full-time gig. That house-painting business has been his livelihood for the past 25 years. He built a life in North Andover with his amazing wife Jill, and their two sons, James and Jacob. And while the years have added up, He hasn't slowed down. His passion for learning, moving, and connecting keeps growing. He’s someone who’s walked his own winding road—full of pivots, passion, and purpose. Today, we’ll explore his story, the chances he’s taken, and the lessons he’s learned along the way. Let’s get into it.

    2h 1m
  7. Taking Chances - Solo - John

    05/11/2025

    Taking Chances - Solo - John

    🎙️ Podcast Intro: Taking Chances – Why Not You? (Solo Debut Episode) Welcome to Taking Chances – Why Not You? Today… it’s just me. That’s right—your host flying solo for the very first time. This week, I’m diving into the top three topics lighting up the world: sports, cryptocurrency, politics, and AI. Okay, that’s four—but who’s counting? I’m not an expert in any of them, so be kind. I’m just here to explore, reflect, and maybe laugh a little along the way. I also open up about my current run streak. I talk about the noise—the negativity that seems to be everywhere. Online. On TV. In our feeds. My take? It’s not helping. So here’s the punchline, the takeaway, the little nugget of wisdom I hope lands: Just try to be happy. This episode is raw, real, and maybe a little rambly—but it’s honest. So if you’ve ever wondered what it sounds like when someone takes a chance on their own voice… press play. Let’s go.

    32 min
  8. Taking Chances - John O'Brien (that's me!) Guest host: Traci (my wife) 1

    27/10/2025

    Taking Chances - John O'Brien (that's me!) Guest host: Traci (my wife) 1

    🎙️ Podcast Promo: Meet John O'Brien — Grit, Growth, and the Long Run From the streets of Peabody, Massachusetts to the finish line of one of the toughest ultramarathons, John O’Brien’s journey is anything but ordinary. A proud husband (wife Traci Kristine OBrien, daughters: Trinity O'Brien Erin O'Brien) and father of two, John’s story blends blue-collar roots, boardroom grit, and backcountry endurance. He graduated from Framingham State with a degree in Economics, captained his college football team and went on to lead initiatives at powerhouse companies like GE Capital, Citibank, and John Deere. But it wasn’t just business where John pushed boundaries. What started as a mission to lose weight turned into a full-blown obsession with the long run. 5Ks, 10Ks, half marathons, marathons, 50Ks, 50-milers—you name it, he’s raced it. And at age 48, he conquered the legendary Leadville Trail 100, crossing the finish line in 28 hours and 42 minutes. This podcast isn’t just about miles or medals—it’s about resilience, reinvention, and the relentless pursuit of growth. Whether you're chasing your first 5K or your next big leap in life, John’s story will inspire you to lace up, lean in, and keep moving forward. 🎧 Tune in and meet the man behind the miles.

    2h 15m
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About

Bold moves, big dreams, and the people who made them happen. In this podcast, we uncover the stories of those who bet on themselves—why they did it, how they pushed through, and what it took to turn risk into reward. Feeling the itch to chase your own dream? Start that podcast. Write that book. Take the leap. ✅ Want to share your story with me, send me an email at: Johnobie2468@gmail.com #takingchances #whynotyou #leadville #lt100 #mentalhealth #Running #hokaoneone #tailwindnutrition #dontquit #hardwork #determination #discipline #motivation #ultrarunning #family #therapy #mentalhealthawareness #training #selflove #selfcare

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