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Taking Chances - Why not you?
Taking Chances - Why not you?
Author: John OBrien
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© John OBrien
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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
33 Episodes
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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
🎙️ S. Scott AndersonScott 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/1663273553Barnes & Noble: https://www.barnesandnoble.com/w/the-scott-boys-s-scott-anderson/1147711487iUniverse: https://www.iuniverse.com/en/bookstore/bookdetails/863188-the-scott-boyswebsite: sscottanderson.comFaceBook: 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/
🎙️ 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."
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!
🎙️ 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.
🎙️ 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.
🎙️ 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.
🎙️ Podcast Promo: Meet John O'Brien — Grit, Growth, and the Long RunFrom 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.
🎙️ Today’s guest is someone who’s not only a powerhouse in the marketing world—but also a cherished part of my family’s story.Anais Elenko is a wife, a mother of two, and a woman whose journey spans continents and courage. When a U.S. visa wasn’t in the cards, Anais didn’t stop dreaming—she pivoted, moved to Canada, and kept building. Years ago, she was an Au pair for my oldest daughter Trinity, and from day one, she became part of our family. Her warmth, resilience, and brilliance have stayed with us ever since.Now, Anais is a marketing speaker and coach with a master’s degree and 15 years of experience helping entrepreneurs simplify their strategy, amplify their visibility, and build brands that actually connect. Her workshops, talks, and masterclasses are known for turning overwhelm into clarity—and making marketing feel not just doable, but fun.Whether you’re just starting out or trying to reignite your brand, Anais brings the kind of insight that sticks. So grab your notebook—or just lean in—and get ready to meet the woman who makes marketing feel like magic.Let’s welcome Anais Elenko to the show.
💥 Meet Traci Kristine O'Brien 💥My wife Traci Kristine OBrien is one of the bravest, most resilient people I know — and on Monday, you’ll hear why.Her career took her across the globe, serving as a civilian with the U.S. Government and Department of the Army. She was deployed not once, not twice, but THREE times to Iraq and Afghanistan. Not in a combat role — but in the thick of it. Mortars hit their bases. Danger was constant. And yet, she showed up, did the work, and made a difference.She’s seen things most of us can’t imagine. And she’s finally sharing her story — the grit, the chaos, the humanity — in her own words.🎙️hear Traci’s journey. It’s raw, powerful, and unforgettable. Funny too. We had a blast doing this one. #TraciKristineOBrien #RealStories #Resilience #PodcastDrop #BehindTheUniform #WomenWhoLead
🎙️ Taking Chances – Why Not You? is back with a powerhouse episode featuring the one and only John DeDonckerHe’s 61 years old. He’s a 9-time Leadville Trail 100 finisher. He’s crushed the Lead Challenge. And he’s still out there doing what most people only dream of—finishing one of the hardest 100-mile trail races on the planet 💪📉 Finisher rate? Around 50% each year.👴 Over 60? Less than 25%.🔥 John? Still getting it done.We dive deep into: 🏃♂️ Training strategies🥗 Nutrition that fuels the grind🧢 Gear that works🧠 Coaching insights🎯 Tips for crossing that elusive finish lineIf you’ve ever wondered how someone keeps showing up, year after year, and defying the odds—this episode is your blueprint.🎧 Tune in, get inspired, and maybe start asking yourself… Why not me?#TakingChancesPodcast #LeadvilleTrail100 #EnduranceLegend #WhyNotYou #TrailRunning #PodcastDrop #JohnDeDoncker #LeadChallenge #MasterAthlete #TrailTips #RunningOver60 #GritAndGrace
🎙️ Taking Chances – Why Not You?🎤 Andy Yohe – He’s a living testament to resilience, reinvention, and the power of sport to heal and elevate. Born with hockey in his blood, he started on the roller rinks of Bettendorf, Iowa as a member of the Young Guns. But in 1994, everything changed—an accident left him without both legs. Most would’ve called it the end. But for Yohe, it was just the beginning of a new kind of fight.Fast forward to 2003: he’s back on the ice, this time with the RIC Blackhawks, and his scoring touch is undeniable. By 2006, he’s representing Team USA in Torino, Italy, helping secure a bronze 🥉 at the Paralympic Winter Games. Four years later in Vancouver? Gold 🏆🥇. And in 2014, after a three-season break, he returns—not just as a player, but as captain of the U.S. Paralympic Sled Hockey Team, leading them to another gold in Sochi. 🏆🥇🇺🇸🇺🇸🇺🇸Three Paralympic medals. Two World Championship podiums. And a legacy that stretches far beyond the rink.Andy Yohe (thank you!)
🎙️ Podcast Intro: Taking Chances – Why Not You?Today’s episode is personal. It’s about grit, sacrifice, and the kind of quiet strength that doesn’t ask for applause—but damn well deserves it.Our guest is my dad, John Joseph O'Brien Jr., born and raised in Peabody, Massachusetts. A proud Peabody High graduate, he joined the United States Marine Corps in 1962, served in Vietnam, and came home in 1966 to start a new chapter—one marked by hard work, humility, and unwavering dedication.He clocked third shift at GE Aircraft Engines in Lynn, Massachusetts, held down two jobs, and raised three boys—me, John Joseph O'Brien III, along with my brothers Michael and Mathew. Back then, he was making $100 a week. But what he gave us was priceless: a blueprint for resilience, responsibility, and love.He’s 81 years old now—and still works every single day. That’s not just longevity. That’s legacy.We lost my mom, his wife, on September 16th, 2001—just days after 9/11. She battled small cell lung cancer with grace and courage. Her absence is felt deeply, but her spirit lives on in the man who never stopped showing up.This episode is for anyone who’s ever wondered if they have what it takes. My dad didn’t ask “Why me?”—he lived “Why not me?” And today, we honor that. Let’s dive in.
🎙️ Podcast Intro: “Taking Chances – Why Not You?” featuring Stacia Carroll🎙️ Taking Chances – Why Not You? From marathons to muscle, we’ve explored what the body can do. But this episode? It’s about what the heart dares to do. Stacia Carroll's story isn’t just about fitness—it’s about sacrifice.She’s a Certified Cancer Exercise Specialist (University of Northern Colorado - Rocky Mountain Cancer Rehabilitation Institute) & Medical Exercise Specialist (American Council on Exercise).Live2Give💚 a living organ donor who didn’t stop after two failed attempts. Stacia Carroll gave part of her liver to a stranger, proving that grit, faith, and a whole lot of heart can change lives.This episode dives into what drives someone to say yes when most would say “someday.”💥 Discomfort is temporary. Impact is forever. Let’s go.Become a donor: https://www.iowadonornetwork.org/ YMCA of the Iowa Mississippi Valley https://www.ymcaimv.org/livestrong-at-the-ymca/Next Monday September 8th: https://www.youtube.com/@takingchanceswhynotyou/videos
🎙️ Podcast Intro: Kevin Bullard Today’s guest is the kind of man who doesn’t just chase greatness—he pedals, swings, and drives straight through it.Born during a snowstorm in Rome, Georgia and raised in the small town of Cedartown, Kevin Bullard’s story starts on two wheels at age three and never slows down. By ten he was a BMX National Champion. By college, a power-hitting catcher breaking records at Armstrong State. And by his twenties, he was suiting up for the Arizona Diamondbacks.But Kevin’s story isn’t just about athletic dominance—it’s about heart, hustle, and the kind of family-first grit that turns champions into legends. After stepping away from pro baseball to raise his son, Kevin picked up a golf club and launched a second career in long drive competitions, sending balls over 400 yards and collecting titles like they were tee markers.Now, he’s a successful entrepreneur in the insurance world, a proud father of two, and a man who knows how to entertain a crowd—whether it’s on the field, the fairway, or the corporate stage.From BMX tracks to boardrooms, Kevin Bullard is proof that small-town roots can grow into big-time impact. Buckle up—this episode is a wild ride through wins, wisdom, and the power of showing up for the people who matter most.Let’s dive in.
🎙️ Taking Chances – Why Not You? with Phil Young!!!Phil is living proof that chasing big dreams—on foot and in business—can lead to extraordinary places. Meet Phil Young, owner of Fleet Feet Davenport, recently named one of the best shoe stores in America.But Phil’s not just lacing up success in retail—he’s also one of the fastest humans to ever run 100 miles, holding one of the top times in the world. Yes, you heard that right.In this episode, we dive into what it takes to build a nationally recognized business, the mindset behind ultra-endurance running, and why taking chances isn’t just for the bold—it’s for anyone ready to ask, “Why not me?”From shoes to strategy, grit to gratitude—this one’s got it all. Let’s go.#podcast #motivation #ultrarrunner #Tunnelhill #FleetFeet #PhilYoung#InspiringVoices #RealTalkRealPeople #DiverseStoriesMatter #CommunityBuilders
Welcome back to Taking Chances – Why Not You?, the show where bold moves, transformative stories, and fearless leadership take center stage.Today’s guest is someone who doesn’t just shape narratives—she builds legacies. We’re joined by Beth Jannery, Founder and President of Titan Strategic Communications, a trusted thought partner to CEOs and a master of executive positioning. With over two decades of experience, Beth has led high-stakes initiatives like a $1 billion global rebrand and helped define the voice of industry giants, including Raytheon Technologies.But her impact doesn’t stop at the corporate level. Beth brings a powerful blend of strategic insight and academic leadership, sharing her expertise as a member of the Fast Company Executive Board and the Forbes Business Council. Whether she’s advising top executives or teaching the art of storytelling, Beth is a force in the world of communications.In this episode, we dive into the mindset behind bold strategy, the power of authentic leadership, and why storytelling isn’t just a skill—it’s a strategic advantage. So lean in, take notes, and get ready to be inspired.Because if Beth Jannery can take chances and shape industries…why not you?🔗 Connect with Beth on LinkedIn https://www.linkedin.com/in/bethjannery/
🎙️ “Today’s guest is Brian Doerrfeld – a Quad Cities native whose journey is a testament to resilience and reinvention. Growing up immersed in golf and sports, Brian’s early years were defined by athletic ambition. But in his twenties, life took a detour as he navigated the highs and lows of bartending, battling depression and a difficult relationship with alcohol. - In 2021, Brian made a bold decision to reclaim his life. Now in his fourth year as a personal trainer, cross country coach, and local 5K race director, he’s not just helping others move forward—he’s racing toward his own goals. His current pursuit? Crushing a sub-70-minute time in the elite HYROX men’s pro division. Brian’s story is about grit, growth, and the power of choosing a different path. This is what Taking Chances is all about.”
Michele Hartwig is a passionate runner, race director, and all-around trail enthusiast from Crystal Lake, Illinois. Michele has chased personal goals with precision and heart—like the time she ran 63.25 miles in under 12 hours, earning her that coveted “100K Under 12 Hours” shirt and a 2nd-place overall female finish. But it’s not just podiums that make her proud. What fuels Michele most is helping others discover their strength. As a race organizer, she's created events that foster friendships, confidence, and personal breakthroughs. Her own journey—from childhood trauma and paralyzing anxiety to peace found through running—adds a deeply personal layer to her mission. “If I can help someone stop hurting like I used to hurt,” she says, “that means more than any finish line.” She now averages about 20 miles a week and spends more time hiking and biking with her husband, whose resilience after injury mirrors Michele’s commitment to adapting without giving up. She’s powered by AC/DC, motivated by watermelon and post-ultra hamburgers, and carries her handheld water bottle and fanny pack like a badge of honor. Her mantra? “Hard work beats talent when talent doesn't work hard.” It’s a philosophy that’s carried her through countless miles—and continues to carry others forward.
Today's guest embodies endurance, dedication, and heart. Meet Erin Montgomery, a force of nature from Clinton, Iowa, where she lives with her partner Todd and their four loyal labs. By day, she’s shaping young minds as an educator in Camanche and coaching cross country, basketball, and track. But Erin's impact doesn't stop there—she’s a dedicated dog breeder, raising labs with care and purpose… and she’s an ultrarunner whose stats are jaw-dropping:🏃♀️ More than ten races of 100 miles or more🏅 A five-time finisher of the Mines of Spain 100 miler💯 And yes, she’s conquered the Potawatomi 150 miler!In 2015, Erin blazed another trail as the Iditarod Teacher on the Trail, bringing the lessons of grit and adventure into classrooms nationwide. She continues to work with Iditarod Education, connecting students with this legendary race through her passion and experience.Whether she's on a school track or a rugged trail deep in the wilderness, Erin shows us what it means to live boldly, push limits, and never settle.🌟 This episode is a celebration of perseverance, purpose, and the magic of saying "yes" to the road less traveled.























