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

    6d ago

    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.

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

    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

    58 min

  3. Jun 5

    Suzie Hall on Blessed Disruption, Leadership, and Turning Trauma Into Triumph

    What if the disruption you have been trying to avoid is actually the thing that could transform your life? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Suzie Hall, global entrepreneur, award-winning interior designer, Founder and CEO of The Cornerstone Collective, speaker, and author of Blessed Disruption: Transforming Trauma Into Triumph. Suzie grew up surrounded by elite athletics as the daughter of a major college football coach. From bowl games to college athletics to entrepreneurship, she learned early what performance, pressure, competition, and resilience look like. But behind the success and achievement, Suzie also experienced personal trauma, disconnection, and seasons of painful disruption that eventually led her to a powerful life reset. In this conversation, Trent and Suzie talk about athletics, entrepreneurship, faith, vulnerability, leadership, personal transformation, and what it means to become the head coach of your own life. This episode is a reminder that winners are not people who never face pain, failure, or setbacks. Winners are the ones who choose to heal, grow, adapt, and find a way forward. In This Episode, We Discuss: Suzie's background growing up in a major college football family How athletics helped shape her confidence, risk tolerance, and leadership Why losing is part of life, business, and personal growth The meaning behind Suzie's book Blessed Disruption How trauma can create disconnection when it is left unprocessed Why halftime can become a powerful reset point in life The difference between accidental disruption and intentional disruption How to stop playing victim and become the head coach of your life Why vulnerability can lead to freedom and healing The importance of discipline, morning routines, faith, and personal growth How parents and leaders teach more through how they show up than what they say Why people need to give themselves permission to play a bigger game Key Takeaways ✨ Disruption can become a blessing when you choose to grow through it. Suzie reminds us that painful seasons can become turning points when we use them to heal, reset, and transform. ✨ You win or you learn. Trent and Suzie talk about how sports teaches us that losing is not final. It is feedback. The lesson is what matters. ✨ Halftime is a chance to reset. When life feels like it has exploded, that may be the moment to pause, reflect, and choose how you want to show up moving forward. ✨ You are responsible for your own scoreboard. Suzie shares how she learned to stop standing on the sidelines and become the head coach of her own life. ✨ Healing starts with awareness. Before we can change our story, mindset, or patterns, we need to become honest about what is holding us back. ✨ Vulnerability creates freedom. Sharing our stories can feel scary, but it can also release the pain that has been holding us hostage. ✨ Small first downs matter. Instead of always going for the Hail Mary, growth often comes from daily discipline, small wins, and consistent action. About Suzie Hall Suzie Hall is a global entrepreneur, award-winning interior designer, Founder and CEO, speaker, and author. She published her memoir, Blessed Disruption: Transforming Trauma Into Triumph, in 2025. Growing up as the daughter of a major college football coach exposed her to elite athletics, competition, high stakes, and the mindset of leaving it all on the field. After transforming herself and her life after what she calls her "Halftime explosion," Suzie now leads and inspires others through her story, faith, and lived experience. Resources Mentioned Blessed Disruption: Transforming Trauma Into Triumph by Suzie Hall Leading Winning Teams by Coach Trent M. Clark Daring Greatly by Brené Brown Be Your Future Self Now by Dr. Benjamin Hardy 10x Is Easier Than 2x by Dr. Benjamin Hardy and Dan Sullivan The Dash Entrepreneurs' Organization James 1:2 2 Timothy 1:7 Connect with Suzie Hall Website: www.suziehall.com Buy the Book: https://suziehall.com/blessed-disruption Book Suzie to Speak: https://suziehall.com/meet-suzie-hall LinkedIn: https://www.linkedin.com/in/suzie-hall-9a0b0a8/ Instagram: https://www.instagram.com/suziehall22/ Facebook: https://www.facebook.com/suziehall22 YouTube: https://www.youtube.com/@suziehall9818 TikTok: https://www.tiktok.com/@suz2design Listen & Subscribe Listen to Winners Find A Way every week for powerful conversations with leaders, entrepreneurs, athletes, and high performers who know what it takes to overcome adversity and keep moving forward. Subscribe on YouTube and all major podcast platforms.

    55 min

  4. May 29 ·  Video

    Mindset, Sales and Building a Busines that Wins with Rob Velazques

    In this episode, Rob Velazquez and Trent Clark discuss the importance of personal growth, resilience, and mental preparation for success. They also share their experiences in overcoming adversity and scaling businesses, highlighting the need for a strong culture and process in place. They also discuss the psychological aspects of success, including visualization and mental preparation, and share their personal experiences in entrepreneurship and personal growth.        Rob Velazquez is a serial entrepreneur and CEO based in Florida. Originally from Dearborn, Michigan, he grew up in a household of immigrant parents from Puerto Rico and Malta. At age 12, Rob was diagnosed with cancer in his leg but overcame it through visualization and positive thinking.      Rob built a successful sales career starting in network marketing and door-to-door telecom sales. He rose to Director of Sales for a major logistics company in his early 20s. Rob has since founded his own SAS company and sales training firm. He leverages over 16 years of sales and business ownership experience to help companies scale through strategic growth.       This interview is guaranteed to give you new strategies for winning in business and life - you won't want to miss it!  JOIN US! 🎙️ New to streaming or looking to level up? Check out StreamYard and get $10 discount! 😍 https://streamyard.com/pal/d/4643596462718976

    1 hr
  5. Debrief Like a Fighter Pilot: The Hidden Habit Behind Continuous Improvement with Jeff "Bones" Bonner

    May 15

    Debrief Like a Fighter Pilot: The Hidden Habit Behind Continuous Improvement with Jeff "Bones" Bonner

    In this episode of Winners Find A Way, Trent Clark sits down with former combat fighter pilot, airline captain, keynote speaker, and author Jeff "Bones" Bonner to unpack one of the most powerful habits behind elite performance — the art of the debrief. Drawing from years in Marine Corps fighter aviation, combat missions, leadership training, and high-performance team culture, Jeff shares how structured reflection helps individuals and teams improve faster, adapt under pressure, and consistently perform at a high level. This conversation dives deep into continuous improvement, leadership, mindset, gratitude, elite team culture, and why experience alone does not create growth. Whether you're a business owner, athlete, leader, entrepreneur, coach, or someone simply trying to become better every day — this episode delivers practical lessons you can apply immediately. Episode Highlights Why fighter pilots debrief every mission — even successful ones The hidden danger of "experience without reflection" How elite teams create a culture of continuous improvement Why gratitude is the foundation of high performance The difference between reviewing failures vs reviewing wins How daily habits shape long-term success Why adversity creates stronger leaders and performers The connection between perspective and performance Applying the debrief method to leadership, parenting, marriage, health, and business The power of 1% daily improvement Powerful Quotes From The Episode "Experience alone doesn't lead to improvement." — Jeff Bonner "Perspective precedes performance." — Jeff Bonner "We're not assigning blame. We're just trying to be better tomorrow." — Jeff Bonner "Championship teams are hard. You have to continuously improve to stay there." — Trent Clark "If we can improve just 1% every day, we'll be in a completely different place 365 days from now." — Jeff Bonner About Jeff "Bones" Bonner Jeff "Bones" Bonner is a keynote speaker, former combat fighter pilot and squadron commander, current airline captain, and Harvard-trained performance strategist. He is the creator of The Debrief Advantage™ System and author of The Daily Debrief™, a practical framework designed to help individuals and teams turn experience into continuous improvement. Jeff helps leaders, organizations, athletes, and teams build high-performance cultures through structured reflection, accountability, and elite-level habits developed from aviation and military leadership. Get Jeff's Free Daily Debrief Framework Jeff is offering listeners access to his free 5-step Daily Debrief framework and 30-Day Challenge. 👉 https://debriefadvantage.com/habit Connect with Jeff "Bones" Bonner LinkedIn: https://www.linkedin.com/in/jeffbonesbonner/ Website: https://debriefadvantage.com Connect with Trent Clark & Leadershipity 🌐 Website: https://leadershipity.com/ 🎙 Winners Find A Way Podcast: https://podcast.winnersfindaway.us/podcast 📺 YouTube: https://www.youtube.com/@leadershipity 🔗 LinkedIn: https://www.linkedin.com/in/trentmclark 📘 Facebook: https://www.facebook.com/trent.m.clark1 📸 Instagram: https://www.instagram.com/leadershipity/ 🐦 Twitter/X: https://twitter.com/TrentMClark Subscribe & Review If you enjoyed this episode of Winners Find A Way, make sure to subscribe, leave a review, and share this episode with someone who wants to improve personally and professionally. Because Winners Find A Way. 🚀

    58 min
  6. Former Poet to PR Expert: Why Most Press Releases Fail with Mickie Kennedy

    May 8

    Former Poet to PR Expert: Why Most Press Releases Fail with Mickie Kennedy

    In this episode of Winners Find A Way, Trent Clark sits down with Mickie Kennedy, founder and president of eReleases, to break down why 97% of press releases fail — and what successful businesses do differently. Mickie shares how storytelling, earned media, and strategic PR can help small and mid-sized businesses stand out in today's noisy digital world. From building compelling headlines to using AI the right way, this conversation is packed with practical insights for entrepreneurs, authors, and business owners looking to build credibility and visibility through media. The episode also dives into Mickie's personal journey from poet and creative writer to building a nationally recognized PR company serving thousands of businesses. In This Episode Why most press releases never get picked up The difference between syndication vs earned media How journalists actually choose stories Why storytelling matters more than company announcements How to use AI effectively for press releases The power of surveys and industry data in PR Why great quotes can make or break media coverage How small businesses can compete for national attention Mickie's journey from poetry to entrepreneurship Key Takeaways Storytelling Wins The best PR campaigns focus on human stories, transformation, and emotion — not just product features. Earned Media Matters Real credibility comes from journalists writing about your business, not just publishing your release on random websites. AI Is a Tool — Not the Strategy AI can help structure and improve writing, but businesses still need strategic angles and compelling narratives. Industry Surveys Create Authority Creating and publishing original survey data is one of the fastest ways to become a thought leader in your industry. Great Quotes Increase Pickups Strong, memorable quotes help journalists build better stories and increase the likelihood your company gets featured. Memorable Quotes "Most press releases fail because they read like ads." — Mickie Kennedy "Stories sell. Data supports the story." — Trent Clark "AI should help you write better — not decide what's newsworthy." — Mickie Kennedy "A great quote is your Trojan horse into the article." — Mickie Kennedy About Mickie Kennedy Mickie Kennedy is the founder and president of eReleases, a PR distribution service helping small businesses, startups, and authors gain real media exposure through PR Newswire distribution and strategic press release campaigns. He is also the author of PR Strategy Manifesto and A Beginner's Guide to Press Release Writing. Outside of business, Mickie is a creative writer and poet whose newest poetry collection, Worth Burning, reflects on life growing up in the South. Resources & Links Connect with Mickie Kennedy 🌐 https://www.ereleases.com/ Free PR Masterclass: https://www.ereleases.com/plan-2/ LinkedIn: https://www.linkedin.com/in/publicity/ Facebook: https://www.facebook.com/ereleases.press.release.distribution Connect with Trent Clark & Leadershipity https://leadershipity.com/ Winners Find A Way Podcast: https://podcast.winnersfindaway.us/podcast  LinkedIn: https://www.linkedin.com/in/trentmclark  Instagram: https://www.instagram.com/leadershipity/  Facebook: https://www.facebook.com/trent.m.clark1 Leadershipity LinkedIn: https://www.linkedin.com/company/leadershipity Subscribe & Review If you enjoyed this episode of Winners Find A Way, make sure to subscribe, leave a review, and share this episode with an entrepreneur or business owner who wants to grow their visibility and credibility through smarter PR. Winners Find A Way with Trent Clark features conversations with elite performers, entrepreneurs, and leaders sharing the lessons, adversity, and mindset that helped them reach the top 1% in their field.

    40 min
  7. From Steel Shop to Pizza Empire | Andris Lagsdin Story

    Apr 28

    From Steel Shop to Pizza Empire | Andris Lagsdin Story

    In this episode of Winners Find A Way, Trent sits down with entrepreneur Andres Lagsdin, founder of Baking Steel, to break down what it really takes to build something meaningful. This isn't just about pizza. It's about: Walking away from comfort Listening to what's not working And having the patience to build something that does About the Guest Andres Lagsten Founder of Baking Steel Built a multi-million dollar brand from a simple idea Blended culinary passion with manufacturing expertise Known for transforming home cooking into restaurant-level experience Built a loyal community around food, family, and craftsmanship Resources Mentioned Baking Steel Products: https://bakingsteel.com 72-Hour Dough Method Live Pizza Classes (via email list) Powerful Quotes "I couldn't tell my son what I did—and be proud." "Break the pattern before you find the path." "Winners don't start from scratch—they connect the dots." "Trust your gut—but earn it through experience." If this episode hit you, don't just listen—apply it. 👉 Watch + Subscribe: https://www.youtube.com/@leadershipity 👉 More Episodes: https://podcast.winnersfindaway.us/podcast

    57 min

  8. Apr 3

    WINNERS FIND A WAY *SPECIAL* - MENTAL TOUGHNESS & WINNING

    Coach Trent shares what it really takes to win—through discipline, daily choices, and mental toughness. Key Takeaways You choose daily: discipline or regret Discipline is short-term. Regret lasts longer Winners execute—no excuses Interested people talk. Committed people act What you repeat daily = who you become Coach Trent's Core Message Winning isn't about talent. It's about the choices you make every day. If you want better results, you need better discipline—and consistency. Action Steps Choose one daily discipline Make it non-negotiable Remove one thing holding you back: → Stop it → Adapt it → Delegate it Quote of the Episode "Winners, when shown data that they are losing… find a way to win." Resources & Links TEDx: The Pain Exchange Book: Leading Winning Teams Book a call: https://calendly.com/trentclark/15min Email: trent@leadershipity.com Listen & Watch LinkedIn Live (Thursdays) YouTube (Leadershipity Channel) Spotify & Apple Podcasts About the Show Winners Find A Way helps leaders, athletes, and entrepreneurs win—through discipline, mindset, and action.

    46 min
See All (260)

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
    260
  • Rating
    Clean
  • Show Website
    Winners Find a Way