Winners Find a Way

Trent M Clark
  • 4.9 (14)
  • Entrepreneurship
  • Updated Weekly

Trent Clark is a serial entrepreneur and three-time Major League Baseball World Series Coach who brings his business and sports insights to interview leaders of business and sport. His guests bring their stories of overcoming adversity, sacrificing for the greater good, and finding a Way to Win.

  1. 4d ago

    The Future of Main Street: AI, Agentic Commerce & Retail Reinvention with Bryan Weisberg

    What if the biggest threat to your retail business isn't Amazon — it's an empty product listing? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Bryan Weisberg, founder of 1000 Oak Barrel Co. and founder/CEO of Merchwise AI, author of The Future of Main Street. Bryan built 1000 Oak Barrel Co. from a chance meeting with a father-and-son barrel maker in rural Mexico into a true omni-channel manufacturer, distributor, and OEM supplier — making close to 2 million barrels in 26 years for retailers from wine enthusiasts to Williams Sonoma. Four years ago, a family emergency (his wife's friend's gift shop closing) pulled him into brick-and-mortar retail, and he realized every part of the business, aside from the POS system, was still manual. That gap became Merchwise AI. Trent and Bryan dig into why e-commerce is still only 16% of retail sales despite decades of predictions, the ROPO effect (research online, purchase offline), and how AI can give independent retailers the same advantages as the big players — without retailers needing to run a full e-commerce operation themselves. This episode is a reminder that winners are not people who never face adversity. Winners are the ones who learn, adjust, grow, and keep finding a way. In This Episode, We Discuss: How Bryan built 1000 Oak Barrel Co. into a vertically integrated, omni-channel manufacturer Why brick-and-mortar retail still drives 84% of sales despite the e-commerce boom The ROPO effect and why "invisible losses" are the biggest hidden cost in retail Temporal commerce vs. agentic commerce — and why timing beats price How Merchwise AI automates product listings, merchandising, and social video for retailers Key Takeaways ✨ Retail's biggest cost isn't rent — it's onboarding new product Getting a product properly listed online (title, description, images, metadata) takes hours most retailers don't have. Merchwise AI does it in 20–30 seconds. ✨ You never see your losses, only your wins If a customer searches for your product online and can't find it, they buy elsewhere — and you never know that sale existed. ✨ Temporal commerce beats agentic commerce for meaningful purchases Agentic (automated) commerce works for commodities like toilet paper. But gifts, meaningful purchases, and one-off decisions need context and timing, not just automation. ✨ Change happens one component at a time Like building a winning team, retail transformation isn't instant. Bryan tells retailers to optimize one small piece of the business, then expand from there. Resources Mentioned The Future of Main Street by Bryan Weisberg — available at merchwiseai.com Merchwise AI — merchwiseai.com 1000 Oak Barrel Co. — mentioned on the show as "1000oaksbarrel.com" (confirm exact URL before publishing) Connect with Bryan Weisberg LinkedIn: https://www.linkedin.com/in/bryanweisberg/ Merchwise AI: https://merchwiseai.com 1000 Oak Barrel Co.: [confirm exact URL — see Need to Confirm] Book: The Future of Main Street — https://merchwiseai.com Connect with Trent M. Clark Trent M. Clark is the CEO of Leadershipity, President of EOS Michigan, a global speaker, former Major League Baseball coach, and author of Leading Winning Teams. Website: https://www.trentmclark.com/ Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@Leadershipity LinkedIn: https://www.linkedin.com/in/trentmclark/ Facebook: https://www.facebook.com/TrentMClark Instagram: https://www.instagram.com/trentmclark/ Book: Leading Winning Teamshttps://leadingwinningteams.trent-clark.com/bookrecording79 Listen & Subscribe Listen to Winners Find A Way every week on YouTube and all major podcast platforms for conversations with leaders, athletes, entrepreneurs, and high performers who know what it means to overcome adversity and keep finding a way.

    The Future of Main Street: AI, Agentic Commerce & Retail Reinvention with Bryan Weisberg

  2. 4d ago ·  Bonus

    You Might Also Like: The Oprah Podcast

    Introducing The Lindsay Clancy Case, Understanding Postpartum Psychosis from The Oprah Podcast. Follow the show: The Oprah Podcast The Lindsay Clancy case has captured the nation’s attention, causing heated debate in the national conversation. On January 24, 2023 Lindsay Clancy strangled her three children in her basement and then attempted suicide by jumping from a second-story window in her house. The resulting injuries left her paralyzed from the waist down. After 21 days of testimony from more than 80 witnesses, the jury was not able to reach a unanimous decision. Lindsay Clancy’s defense team has argued that she is not guilty by reason of insanity as she was experiencing postpartum psychosis, while the prosecution argued she committed premeditated first degree murder. Oprah is in Massachusetts for a wide-ranging conversation about the case with an audience including an exclusive interview with Meg Hamp, a nurse who worked alongside Lindsay for 7 years and testified at her trial - plus medical experts, legal scholars and women who have personally experienced postpartum psychosis. Their stories give us a rare, first-hand insight into what it is to experience this challenging mental health issue. Oprah will also talk with social critics who will share their opinions and she will hear speculation on many sides of the case. Oprah has hosted conversations on postpartum depression and psychosis for 40 years with the intention of providing a platform for a mature discussion. This podcast episode contains discussions of murder, suicide, and mental illness that may be upsetting to some listeners. Listener discretion is advised. Follow Oprah Winfrey on Social: https://www.instagram.com/oprahpodcast/ https://www.facebook.com/oprahwinfrey/ Listen to the full podcast:  https://open.spotify.com/show/0tEVrfNp92a7lbjDe6GMLI DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to team@podroll.fm.

    You Might Also Like: The Oprah Podcast

  3. Sep 4

    Relentless Reinvention: How Pat Miletich Became Superhuman

    What if the thing holding you back isn't a lack of willpower — it's what's actually going into your body? On this episode of Winners Find A Way, Coach Trent M. Clark sits down with Pat Miletich — the first UFC Welterweight Champion, a coach behind 12 MMA world champions, a trainer to military and special forces for over 15 years, and founder of Cell Saviors and Soil Saviors. Pat grew up in Bettendorf, Iowa unable to breathe through wrestling matches and football games, with no doctor able to explain why. He went and found the answer himself — a search that carried him from kickboxing into the UFC, and eventually into 40 years of research on soil health, nutrient depletion, and cellular repair. In this episode, we discuss: How undiagnosed respiratory illness shaped Pat's path from wrestling to kickboxing to the UFC The 10-day protocol that took him from struggling through 3 rounds with a world-champion boxer to sparring a full 10 Why "genetic expression" works the same way in a plant and in a person What depleted, chemically farmed soil is doing to our food, water, and immune systems Why real change starts with fixing yourself before you can lead or help anyone else Connect with Pat Miletich: Website: https://www.soilsaviors.org    Connect with Trent M. Clark: Website: https://www.trentmclark.com/  Leadershipity:  Book "Leading Winning Teams": https://leadingwinningteams.trent-clark.com/bookrecording79 Winners find a way. #WinnersFindAWay #Leadership #PatMiletich #UFC #TrentClark #Leadershipity

    Relentless Reinvention: How Pat Miletich Became Superhuman

  4. Aug 29

    Pressure, Purpose, and the Dream-Truth-Promise Framework: Lessons from Jenison High School

    In this episode of Winning Ways, Coach Trent M. Clark shares lessons from his recent time with the athletes and coaching staff at Jenison High School—and breaks down a simple framework for turning potential into action. Trent explores three powerful steps: The Dream: Get clear on what you truly want and identify the big goal you're working toward. The Truth: Learn how to actually get there by finding mentors and people who have already achieved what you're pursuing. The Promise: Move from being interested to being committed. Make a clear promise to yourself about what you will do and by when. Trent also discusses handling pressure, preparing yourself to perform at your best, protecting your priorities, and taking intentional action every day. Key Takeaway: Winners don't just dream about what they want—they get the truth, make a commitment, and take consistent action to build their way toward it. Listen in and ask yourself: What is your dream? What is the truth about how you'll achieve it? And what promise are you willing to make to yourself?

  5. Jul 27

    Acting Onbeat, Thinking Offbeat: Michael & Matthew Gardiner on Building a Global Brand Through Systems and Creativity

    What does it take to turn a childhood tradition into a platform with 1.5 billion views, without losing what made it real in the first place? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Michael and Matthew Gardiner, known as the Gardiner Brothers, five-time World Champion Irish dancers, global content creators, keynote speakers, and performers. Michael and Matthew were born in Denver to Irish parents and raised in Galway, Ireland, where their parents put them into Irish dancing to keep their culture alive. That decision became a full career: the brothers went on to become principal dancers with Riverdance, touring the world as lead performers. When the pandemic shut down live shows, they made a choice that changed everything. They started filming themselves dancing to unexpected music, from Michael Jackson to Eminem, and posted it online. That decision grew into a platform with over 9 million followers and 1.5 billion views, and eventually into their touring production, Unleashed, and a keynote and speaking business built around innovation and creativity. What stands out in this conversation is the system behind the art. Michael and Matthew break down their framework, "acting on beat, thinking offbeat": onbeat is your structure (your product, your goals, your process), and offbeat is the creative edge that turns good into great. Both brothers also hold degrees, Michael in architecture and Matthew in civil engineering, and they explain how that technical training shaped the systems now running their business. The conversation also moves into a topic every leader needs to think about right now: discernment, and why real, in-person experience is becoming more valuable as AI reshapes what audiences see online. This episode is a reminder that winners are not people who never face setbacks. Winners are the ones who learn, adjust, lead, and find a way. In This Episode, We Discuss: How a pandemic pause turned into a platform with 9+ million followers and 1.5 billion views The "acting on beat, thinking offbeat" system for building innovation into any business How Michael's architecture degree and Matthew's civil engineering degree shaped the systems behind Gardiner Brothers What it means to be a disruptor by combining things that "don't make sense" together Why discernment and real, in-person experience matter more as AI content grows Growing up as children of Irish immigrants in Denver, and what community and culture taught them about connection Key Takeaways ✨ Systems and creativity have to work together Michael and Matthew's "onbeat, offbeat" framework shows that structure alone will not make you innovative, and creativity alone will not scale. You need both, working in relationship with each other. ✨ Your background is never wasted An architecture degree and a civil engineering degree do not sound like tools for building a global content business. But Michael and Matthew show how that training gave them the systems thinking behind everything they do now. ✨ Discernment is a leadership skill, not just a talent As AI blurs the line between real and fake, knowing the difference between quality and mediocrity, or truth and noise, is becoming one of the most valuable things a leader can teach their team. ✨ Disruption comes from combining what doesn't seem to fit Irish dance and Smooth Criminal should not work together. That is exactly why it did. Innovation often starts by putting two things next to each other that nobody expected. Resources Mentioned Leading Winning Teams by Trent M. Clark: https://leadingwinningteams.trent-clark.com/bookrecording79 Connect with Michael & Matthew Gardiner Website: https://www.gardinerbrothers.com Instagram: https://www.instagram.com/gardinerbrothers/ TikTok: https://www.tiktok.com/@gardinerbrothers Facebook: https://www.facebook.com/gardinerbrothers/ YouTube: https://www.youtube.com/@gardinerbrothers LinkedIn (Matthew): https://www.linkedin.com/in/matthew-gardiner-gardiner-brothers-6b2320296/ LinkedIn (Michael): https://www.linkedin.com/in/michael-gardiner-gardiner-brothers-54897b1ba/ LinkedIn (Company): https://www.linkedin.com/company/gardiner-brothers Connect with Trent M. Clark Trent M. Clark is the CEO of Leadershipity, President of EOS Michigan, global speaker, former Major League Baseball coach, and author of Leading Winning Teams. Website: https://www.trentmclark.com/ Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@Leadershipity LinkedIn: https://www.linkedin.com/in/trentmclark/ Facebook: https://www.facebook.com/TrentMClark Instagram: https://www.instagram.com/trentmclark/ Book: Leading Winning Teams — https://leadingwinningteams.trent-clark.com/bookrecording79 Listen & Subscribe Listen to Winners Find A Way every week on YouTube and all major podcast platforms for conversations with leaders, athletes, entrepreneurs, and high performers who know what it means to overcome adversity and keep finding a way.

    Acting Onbeat, Thinking Offbeat: Michael & Matthew Gardiner on Building a Global Brand Through Systems and Creativity

  6. Jul 18

    Building Businesses, Creating Jobs & Leading with Purpose with Gary Rabine

    What does it really take to build lasting businesses, create opportunities, and lead with impact? In this episode of Winners Find a Way, Trent Clark sits down with entrepreneur, business leader, and Rabine Group founder Gary Rabine. Having started more than 40 companies over four decades, Gary shares the lessons he's learned about entrepreneurship, leadership, resilience, and creating meaningful impact through business. The conversation explores how strong leadership starts with serving customers, building winning teams, and surrounding yourself with people who strive for excellence. Gary also discusses his experience running for governor of Illinois, his passion for economic growth, and why he believes entrepreneurs have an important role in shaping the future. Whether you're a business owner, leader, entrepreneur, or someone looking to make a greater impact, this episode is filled with practical insights on leadership, opportunity, and thinking long-term. In This Episode You'll Learn: How Gary Rabine built more than 40 companies over his entrepreneurial career. Why winning teams are built by finding the right people—not just the most talented. The importance of solving customers' biggest problems. How relationships and trust become a competitive advantage. Lessons learned from running for public office. Why entrepreneurs should focus on creating jobs and opportunities. How leadership and business principles can be applied beyond the workplace. Why adaptability will matter more than ever in an AI-driven world. The growing importance of communication, relationships, and emotional intelligence. Practical advice for entrepreneurs navigating today's changing economy. Key Takeaways Great businesses are built by solving real problems. Strong cultures are created by hiring people who share the mission. Relationships are one of the most valuable assets a leader can build. Entrepreneurs create opportunities by taking calculated risks. Leadership is about serving others and creating lasting impact. Technology will continue to evolve, but trust and human connection remain irreplaceable. Success comes from continually learning, adapting, and surrounding yourself with great people. Memorable Quote "The ability to build relationships of trust will become one of the most valuable skills in the future." — Gary Rabine Connect with Gary Rabine Podcast: Ditch Digger CEO LinkedIn: Gary Rabine Connect with Trent Clark Learn more about Trent Clark, Leadershipity, coaching, speaking, and leadership development through Leadershipity and the Winners Find a Way podcast.

    Building Businesses, Creating Jobs & Leading with Purpose with Gary Rabine

  7. Jun 26

    The Art of Angel Investing: How Tony Wilkins Went from Chrysler Layoff to Financial Freedom

    What happens when everything you were told to do stops working — and you have to figure it out at 23? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Tony Wilkins, Northwestern and University of Chicago Booth graduate, longtime angel investor, executive coach, cancer survivor, and author of The Art of Angel Investing. Tony grew up as the oldest of six boys, built his career as an electrical engineer at Chrysler Corporation in 1979, and was laid off after just one year, along with 300 others. At 23, with everything he thought he had figured out suddenly gone, he made a decision that would shape the rest of his life — stop solving for a job and start solving for financial independence. From there, he went on to earn his MBA at Booth, build a career in high-level banking and finance, become a founding member of Hyde Park Angels in Chicago, and invest in early-stage companies like Spot Hero (acquired by Uber), Cameo, and Nutrasense. This conversation is about more than investing. Tony and Trent dig into what it really means to be the CEO of yourself — knowing what you are solving for, being ruthless about what you can control, and letting go of what you can't. Tony shares how the layoff that shattered his plans at 23 was actually the best thing that ever happened to him, why he secretly applied to Harvard Business School nine months into his dream job, and how a mentee half his age gave him one of the most powerful leadership phrases he's ever heard: "I am firm in my mission and flexible in my methods." This episode is a reminder that winners are not people who never face setbacks. Winners are the ones who learn, adjust, lead, and find a way. In This Episode, We Discuss: How getting laid off at 23 became Tony's most important life lesson Why you must know what you are really solving for — not just what you want right now The CEO of your mindset and owning your results completely Being ruthless about what you can control and letting go of everything you can't How to get started as an angel investor — even without Silicon Valley connections The concept of "triumph or tuition" and why every investment teaches you something How change, AI, and the next generation will shape the future of leadership Key Takeaways ✨ Know what you're really solving for It's not enough to want a good job or a big title. Tony asks every client: "What are you really solving for?" Keep asking why — five times if you have to — until you get to the truth beneath the surface answer. ✨ Be the CEO of yourself You are responsible for your results. No one is coming to save you. Tony learned this at 23 when Chrysler cut 300 people without warning. The sooner you take full ownership of your direction, the sooner your life changes. ✨ Be ruthless about what you can control Tony's rule: be ruthless about what you can control and ruthlessly ignore everything you can't. Gravity exists. Corporate layoffs happen. AI is here. Your energy goes toward what you can actually move. ✨ Triumph or tuition — just get in the water You cannot learn to swim from a book. You cannot become an angel investor without writing a check. Every investment either gives you a triumph or pays your tuition. Either way, you are learning. The key is to start. ✨ Firm in your mission, flexible in your methods A young mentee said this to Tony at the end of a coaching call, and it stopped him cold. Your mission is the non-negotiable. How do you get there? That can evolve. The best leaders hold both at once. Resources Mentioned The Art of Angel Investing by Tony Wilkins Hyde Park Angels — Chicago-based angel investing group Spot Hero — parking app, acquired by Uber Cameo — celebrity video platform Nutrasense — glucose monitoring and quantified self-tracking Connect with Tony Wilkins Instagram: @TonyWilkinChicago LinkedIn: Tony Wilkins 76 Connect with Trent M. Clark Trent M. Clark is the CEO of Leadershipity, President of EOS Michigan, a global speaker, former Major League Baseball coach, and the author of Leading Winning Teams. Website: https://www.trentmclark.com/ Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@Leadershipity LinkedIn: https://www.linkedin.com/in/trentmclark/ Facebook: https://www.facebook.com/TrentMClark Instagram: https://www.instagram.com/trentmclark/ Book: Leading Winning Teams — https://leadingwinningteams.trent-clark.com/bookrecording79 Listen & Subscribe Listen to Winners Find A Way every week on YouTube and all major podcast platforms for conversations with leaders, athletes, entrepreneurs, and high performers who know what it means to overcome adversity and keep finding a way.

    The Art of Angel Investing: How Tony Wilkins Went from Chrysler Layoff to Financial Freedom

  8. Jun 12

    How to Raise Champions: John O'Sullivan on Youth Sports, Coachability, and What Scouts Really Look For

    Are you building a champion — or just chasing a trophy? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with John O'Sullivan, author, speaker, and founder of Changing the Game Project — one of the most influential voices in youth sports development today. John is a former Division I soccer player at Fordham University, a master's-level researcher, and the author of five books on youth sports, coaching, and athlete leadership. His work has been recognized by the US Olympic Committee and major sport governing bodies around the world. He co-hosts the Way of Champions podcast with Jerry Lynch — nearly 500 episodes with guests like Phil Jackson and Steve Kerr — and his latest book, Captain: The Athlete's Guide to Being an Exceptional Team Leader, is now available everywhere. This conversation covers the full landscape of what it actually takes to develop athletes — and what so many coaches and parents get wrong. John and Trent dig into the difference between information and knowledge, why curiosity is the number one trait of elite coaches, and how the "me culture" of college sports is trickling down to youth programs. They talk about parents, pressure, social media, NIL, and the moment a coach stops talking to an athlete — and what that silence really means. This episode is a reminder that winners are not people who never face setbacks. Winners are the ones who learn, adjust, lead, and find a way. In This Episode, We Discuss: Why the best coaches in the world share one common trait — curiosity What John's new book Captain teaches athletes about leading from any position How the "me culture" in college sports trickles down and why kids struggle to transition to team-first environments What scouts actually ask about when they watch your kid play The real role of parents in youth sports — and how to be the fan your child needs Why coachability is a decision, not a personality trait The inner voice: how to train the coach inside your head Individual sports vs. team sports — and why every athlete should experience both Key Takeaways ✨ Curiosity is the common denominator of elite coaches John has interviewed Hall of Famers, Olympians, and championship coaches for nine years. Every single one is still curious. The ones who plateau decided they already know everything. ✨ Great teammates are always in demand Scouts don't just watch the stats. They ask: How does this kid treat the worst player on the team? Character traits like humility, coachability, and selflessness are skills — and they carry into every team you'll ever be part of. ✨ When a coach stops talking to you, the end is near Coaches invest their energy where it counts. Three "yeah buts" and they redirect to athletes who are coachable and worth the oxygen. ✨ Train the voice in your head The late Jim Lehr said it best: the most influential coach in your life is the voice inside your head. If that voice was a person, would you be friends with them? ✨ Begin with the end in mind Before signing your kid up for a travel team, ask: What do I actually want sports to give them? Then find a coach and program that builds those things. Resources Mentioned: Captain: The Athlete's Guide to Being an Exceptional Team Leader by John O'Sullivan & Jerry Lynch Way of Champions Podcast Changing the Game Project — https://changingthegameproject.com The Matheny Manifesto — referenced in conversation The Talent Code by Dan Coyle — referenced in conversation Connect with John O'Sullivan: Website: https://changingthegameproject.com Podcast: Way of Champions Book: Captain — available on Amazon Connect with Trent M. Clark: Website: https://www.trentmclark.com/ Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@Leadershipity LinkedIn: https://www.linkedin.com/in/trentmclark/ Book: Leading Winning Teams — https://leadingwinningteams.trent-clark.com/bookrecording79

    How to Raise Champions: John O'Sullivan on Youth Sports, Coachability, and What Scouts Really Look For
See All (266)

Trailer

4.9
out of 5
14 Ratings

About

Trent Clark is a serial entrepreneur and three-time Major League Baseball World Series Coach who brings his business and sports insights to interview leaders of business and sport. His guests bring their stories of overcoming adversity, sacrificing for the greater good, and finding a Way to Win.

Information

  • Creator
    Trent M Clark
  • Years Active
    2021 - 2026
  • Episodes
    266
  • Rating
    Clean
  • Show Website
    Winners Find a Way