Winners Find a Way

Trent M Clark

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. 3d ago

    Self-Storage Investing: What 42 Properties and 450 Investors Teach About Leadership and Risk | Jacob Vanderslice

    What does it take to keep 450 investors confident through a crash, a rate spike, and a few very bad nights at the storage facility? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Jacob Vanderslice, co-founder of VanWest Partners and a self-storage investor. Jacob started as a career firefighter. He left right before the 2008 crash to invest full time. He took the hit, learned from it, and went on to complete more than 1,000 fix-and-flips and rentals. Today VanWest owns 42 self-storage properties, about 21,000 units and 3.2 million square feet. Trent and Jacob get honest about the parts people miss. Storage looks simple, but it is operationally intense. Deals look different in hindsight. Partnerships take real work. Jacob shares how his team learns from mistakes, plans for risk, and keeps investing in the people beside them. 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: Why Jacob went from firefighter to full-time real estate investor What the 2008 crash taught him about risk Why self-storage is more operational than most people think What the "thin" deal and the "home run" deal taught his team about underwriting How to invest in partnerships the way you invest in assets Key Takeaways ✨ Protect the capital first Jacob's number one goal is simple. If someone gives you $200K, give them at least $200K back. ✨ Failure is the best audit Jacob learned storage by doing it. Mistakes showed him risks he never saw coming, like new supply and fast-rising rates. ✨ Underwrite with humility The deal that felt thin became a top performer. The "home run" returned the least. Stress test your assumptions, then add more margin. ✨ Invest in relationships like you invest in assets Jacob and his partners have worked with a business coach for five years. A band-aid on a leaky roof only costs you more later. The same goes for partnerships. Resources Mentioned The VanWest Investor's Playbook. Email Jacob to request it. Leading Winning Teams by Trent M. Clark Connect with Jacob Vanderslice LinkedIn: https://www.linkedin.com/in/jacob-vanderslice-02905b16b/ Email: jacob@vanwestpartners.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. Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@coachtrentclark 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.

    Self-Storage Investing: What 42 Properties and 450 Investors Teach About Leadership and Risk | Jacob Vanderslice
  2. Oct 23

    How to Live Intentionally and Turn Hard Seasons Into Growth with Nicole Middendorf

    What if your hardest season is where your best life begins? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Nicole Middendorf, CEO of Prosperwell Wealth, founder of the Live It List, and 5x author. Nicole never planned to be a wealth advisor. She wanted to go to law school and change the world. Then life took a hard turn. During a painful divorce, she rewrote her bucket list and decided to do one thing a month for a year. That choice became the Live It List. It is now a movement with a community, events, trips, and a journal. Nicole and Trent talk about mindset, accountability, teaching kids about money, and why small changes lead to big results. 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 the Live It List started on a plane to Vegas Why "can't" is not in Nicole's dictionary Why a challenge beats a problem every time How Nicole found and bought the building she wanted How to talk to your kids about money Why accountability is a team skill The Happiness Wheel and how to use it Key Takeaways ✨ Do one thing a month. You do not need a big trip. Go to a movie alone. Have a pillow fight with your kids. Be intentional so you do not reach the end with regrets. ✨ Growth shows up at the bottom. When life feels as low as it can go, that is often where the most meaningful change begins. ✨ Swap "problem" for "challenge." Problems drain people. Challenges invite solutions. Ask what you are going to do about it. ✨ Small changes add up. Put items in your cart and wait until Friday to check out. Use cash. Automate your paycheck. Simple systems build discipline. Live It List Foundation Updates Restart Program Nominations Are Open Do you know a woman who is ready for a fresh start, a new chapter, or a Restart? Throughout October, the Live It List Foundation is accepting nominations for the Restart Program. It supports women who have survived domestic violence as they move from survivors to thrivers. Every woman deserves the chance to rebuild, rediscover her strength, and create what's next. Nominate a woman who deserves support, encouragement, and a fresh start at www.theliveitlist.com. Join Us in Celebrating Women On Thursday, October 22, join us at The Lafayette Club for our Women's Empowerment Luncheon. It is a day for connection, inspiration, shopping, networking, and celebrating women. Come together with an incredible community of women and help support the mission of empowering women to move forward and thrive. Reserve your spot for the Women's Empowerment Luncheon Can't Attend? You Can Still Make an Impact! The silent auction is open now. You do not need to attend the luncheon to bid. There are incredible items and experiences waiting for you. Browse the auction, find something you love, and place your bid today. You will be supporting the women the foundation serves. Explore the Silent Auction & Start Bidding  Connect with Nicole Middendorf Live It List: https://www.theliveitlist.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. Leadershipity: https://www.leadershipity.com/ YouTube: https://www.youtube.com/@coachtrentclark 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. Spotify: https://open.spotify.com/show/7GAwyvYA7OY1L2JOjegX7D Apple Podcasts: https://podcasts.apple.com/us/podcast/winners-find-a-way/id1578413577 All platforms: https://pod.link/1578413577

    How to Live Intentionally and Turn Hard Seasons Into Growth with Nicole Middendorf
  3. Oct 16

    Ric Bucher - NBA Analyst | Author | Book, Coachable

    What separates a player who plateaus from one who keeps improving? It usually isn't talent — it's coachability. In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Ric Bucher, longtime NBA analyst and author of Coachable. Ric grew up a high school All-American soccer player in Cincinnati before walking onto Dartmouth's varsity team and building a sportswriting career that wound through Sports Illustrated, a small-town San Diego paper, and the San Jose Mercury News before landing him on the NBA beat. Along the way, he learned the lesson at the center of his book: being coachable isn't about blind obedience — it's about synthesizing who you want to be with someone else's vision of how you get there. The conversation covers Steph Curry rebuilding his shot after being told it wouldn't translate to the next level, Trent's own missed free throw and the lesson his dad taught him about it, and why consistency — not talent — is what wins championships. 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: What "coachability" really means — and why it's often misunderstood as weakness The ACE framework How Steph Curry rebuilt his shot from scratch after being told it wouldn't work at the next level Why the setbacks you don't talk about shape you more than the wins you do The parent-coach-athlete alignment problem — and why it usually goes south How Ric's "wrong turn" into covering high school sports became the foundation of his career Key Takeaways ✨ Coachability is confidence plus humility You need the confidence to believe you can be great, and the humility to let someone else shape how you get there. ✨ Consistency beats one moment A single mistake doesn't define the game — all 90 minutes do. The same is true off the field. ✨ Adaptability is part of being coachable What worked to get you here won't always work at the next level. The willingness to change is the skill. ✨ Your "wrong turn" might be the right one Ric's detour covering high school sports in San Diego taught him the fundamentals that built his entire career. Resources Mentioned Book: Coachable by Ric Bucher Connect with Ric Bucher LinkedIn: https://www.linkedin.com/in/ric-bucher/ 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. 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.

    Ric Bucher - NBA Analyst | Author | Book, Coachable
  4. Oct 9

    Revisit It, Don't Relive It: Vincent Lanci on Brain Injury, Boundaries, and Building a Business

    What would you do if one night took away everything you had planned for your life? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Vincent A. Lanci, author, TBI coach, and founder of Coming Alive Podcast Production. At 21, Vince was a finance student one semester from graduating. He had interned at Merrill Lynch and Northwestern Mutual and worked busy season at PricewaterhouseCoopers. Then he was hit by a car while walking home. He woke from a coma a week later with a severe traumatic brain injury. When a nurse asked which school he went to, he named his elementary school. He was told he might need 24/7 care for the rest of his life. Instead, he was back in Tampa and independent about two months later. In 2015, he spoke at his MBA commencement. Today he helps survivors, caregivers, and entrepreneurs share their stories through books, coaching, and podcasting. Trent and Vince talk about the hidden side of brain injury, why every recovery is unique, and how to revisit a hard moment without reliving it. They also get practical about time audits, boundaries, communication styles, and mentorship. 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: Vince's accident, coma, and starting over from zero at 21 Why TBI is a "hidden disability" and how that affects survivors TBI Recovery: Extended Edition and why caregivers need support too Revisiting the past without reliving it (Trent's rearview mirror lesson) Learning with more than one modality when you hit a wall Time audits, productive breaks, and setting boundaries as a business owner Asking for help in recovery, business, and life Mentorship as a value exchange Practical tips for starting a podcast and why Podfest is worth attending Key Takeaways ✨ Your dark day is not your tomorrow. Vince went from a possible lifetime of 24/7 care to speaking at his MBA commencement. A hard season is not a life sentence. ✨ Revisit it. Don't relive it. Glance in the rearview mirror, learn the lesson, then look through the windshield and move forward. ✨ Nobody wins alone. Every brain and every recovery is different. But without help and support, no one reaches their full potential. ✨ Intentional time creates impact. Do a time audit. Block your priorities, breaks, and exercise. Protect your best hours and set clear boundaries. Resources Mentioned TBI Recovery: Extended Edition by Vincent A. Lanci (free ebook: email info@vincentalanci.com) Left for Dead by Vincent A. Lanci Coming Alive Podcast Production monthly mastermind calls (free when you mention Winners Find A Way) Brain Injury Breakthroughs podcast (coming soon) Podfest Orlando (January) Start Ugly by Chris Krimitsos Leading Winning Teams by Trent M. Clark Connect with Vincent A. Lanci Website: https://vincentalanci.com/ LinkedIn: https://www.linkedin.com/in/vincentalanci/ Coming Alive Podcast Production: comingalivepodcastproduction.com Email: info@vincentalanci.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 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.

    Revisit It, Don't Relive It:  Vincent Lanci on Brain Injury, Boundaries, and Building a Business
  5. Oct 6

    How to Write a Signature Book That Builds Your Authority & Grows Your Coaching Business with Sophie Howard

    What if the fastest way to build authority, attract better clients, and create more opportunities for your coaching business isn't another funnel—but a book? In this episode of Winners Find A Way, Trent Clark sits down with Sophie Howard, business coach, publishing strategist, and founder of the Signature Book Method, to talk about how coaches can turn their expertise, stories, and proven methods into a book that helps prospects know, like, and trust them. Sophie explains why a signature book isn't simply about becoming a published author. When strategically created, your book can become a powerful business tool that introduces people to your expertise, builds credibility, generates leads, and creates a natural next step toward working with you. Sophie also shares how AI is changing the book-writing process, why you don't need to be a world-famous expert to write a book, and how she uses books as part of a larger marketing ecosystem. In This Episode, You'll Learn: Why coaches should consider creating a signature book How a book can help prospects know, like, and trust you The difference between a book that sells and a book that generates business How Sophie built successful coaching businesses from her books Why your book should showcase your story, personality, values, and methodology How AI can help you create a book while keeping your own voice and experience at the center Why you don't need to be the world's leading expert to write a valuable book How to use a book as a lead magnet and business card How your book can warm up prospects before they ever get on a sales call Why Sophie focuses on building an email list rather than relying entirely on social media algorithms How to use your book across LinkedIn, Instagram, YouTube, podcasts, speaking engagements, and email Why a strong title, subtitle, and cover matter How print-on-demand has changed self-publishing The biggest psychological barriers that stop coaches from writing their books How Sophie recovered after a major Facebook algorithm change disrupted a successful marketing funnel How to create a book that supports your existing marketing and sales process Your Book Can Be More Than a Book Sophie shares a powerful perspective throughout the conversation: the book isn't necessarily the product—the expertise behind the book is. A signature book can serve as: A credibility builder A lead magnet A marketing asset A conversation starter A way to showcase your methodology A tool for warming up prospects A resource you can use on podcasts and speaking stages A bridge into your coaching or consulting offer The goal isn't simply to sell thousands of copies. The goal is to put your expertise in front of the right people and give them a reason to take the next step. Using AI Without Losing Your Voice Sophie explains how she uses AI differently from simply asking it to write generic content. Her approach involves using AI to interview the author, draw out their experiences, stories, frameworks, case studies, and ideas, and then organize those insights into a book. That allows the final book to be based on the author's own experience and methodology rather than generic information that anyone could generate. Building an Audience You Own Sophie also opens up about a major business lesson she learned when a Facebook algorithm change caused one of her successful funnels to stop working. The experience pushed her to focus more heavily on building an audience through her own email list. For Sophie, a book can be an effective way to bring people from different platforms into an audience you have more control over. You Don't Have to Be the World's #1 Expert One of the biggest mindset barriers Sophie addresses is the belief that you aren't qualified enough to write a book. You don't necessarily need to be the world's leading expert. Your experience, perspective, methodology, and the way you help a specific type of person can be enough to create something valuable. A signature book gives potential clients a way to understand how you think, what you believe, and how you help people achieve results. About Sophie Howard Sophie Howard is a business coach and publishing strategist who has spent more than a decade building businesses from New Zealand. Her experience includes two successful coaching businesses and more than 170 self-published books. Through her Signature Book Method, she helps established executive coaches take their expertise beyond the room they're already in. Connect with Sophie Howard Website: SignatureBookMethod.com Authority Builders: AuthorityBuilders.club LinkedIn: Sophie Howard Sophie is also offering the Signature Book Method as the featured resource for this episode. Key Takeaway Your book doesn't have to be the end product. It can be the beginning of the conversation. Use your expertise, stories, and methodology to create something that introduces the right people to your work—and gives them a natural next step to connect with you. If you enjoyed this episode, subscribe to Winners Find A Way, share this episode, and leave a review to help more entrepreneurs, coaches, and leaders discover the show. Connect with Trent Clark: Trent-Clark.com Listen to Winners Find A Way: Available on major podcast platforms, including Apple Podcasts and Spotify.

    How to Write a Signature Book That Builds Your Authority & Grows Your Coaching Business with Sophie Howard
  6. Sep 26

    Debt Free Is Not Financially Free, Joey Muré On Wealth Without Wall Street

    What if the plan you were handed (work harder, max out your 401(k), and wait for retirement) is the very thing keeping you from the life you want? In this episode of Winners Find A Way, Coach Trent M. Clark sits down with Joey Muré, founding partner at Wealth Without Wall Street, where he helps business owners stop trading time for money by building passive income that exceeds their monthly expenses. By his late 20s, Joey was earning over $300,000 a year in the mortgage industry. On paper, he was winning. In real life, he was working 60 to 70 hours a week and missing his family. One walk down a beach boardwalk, watching his wife and daughters head the other way, showed him that more income was not the answer. Joey and Trent talk about how to define what freedom looks like for you, why retirement can become a deferment of life, and how Infinite Banking lets your dollars do two jobs at once. Joey explains why being debt free is not the same as being financially free, and why the right investment is the one that fits who you are. Joey also shares the hardest decision of his career. He walked away from a $300,000 income, started from zero, and began teaching others what he had learned. Today, he and his business partner Russ have built over $50,000 a month in passive income. 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: Why a higher income is not the same as financial freedom The financial freedom formula: passive income that exceeds monthly expenses How to dream again using the Be, Do, Have framework Why Joey calls retirement a deferment of life The GPS framework: Goal, Plan, and Support Infinite Banking explained in simple terms Why debt free can still mean broke The Investor DNA Profile and choosing passive income that fits you Building a castle and moat so you are ready for the next economic shift Key Takeaways ✨ More income will not buy back your time. Joey earned over $300K a year and still never left the office. Freedom starts when passive income covers your monthly expenses. ✨ Debt free is not financially free. Groceries, utilities, insurance, and daily life never get paid off. If you only focus on debt, you never build the income side of the formula. ✨ Make every dollar do two jobs. Infinite Banking works like a rewards card. You use money you were going to spend anyway, but it works for you first. ✨ Invest like you, not like someone else. What works for someone else may not fit your personality, resources, or values. Know who you are as an investor and go deep. Resources Mentioned Wealth Without Wall Street (book) Wealth Without Wall Street page for Winners Find A Way listeners: https://wealthwithoutwallstreet.com/winnersfindaway Wealth Without Wall Street Quiz: https://quiz.wealthwithoutwallstreet.com/ Investor DNA Profile The 4-Hour Workweek by Tim Ferriss Cashflow board game by Robert Kiyosaki The 4 Disciplines of Execution Leading Winning Teams by Trent M. Clark Connect with Joey Muré Website: https://wealthwithoutwallstreet.com/winnersfindaway Free Quiz: https://quiz.wealthwithoutwallstreet.com/ LinkedIn: https://www.linkedin.com/in/joey-mure-b376824/ Facebook: https://www.facebook.com/wealthwithoutwallstreet Instagram: https://www.instagram.com/wealthwithoutwallst X: https://x.com/withoutwallst Connect with Trent M. Clark Trent M. Clark is the CEO of Leadershipity, President of EOS Michigan, a Bloom Growth Coach, 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/ Bloom Growth Coach: https://www.bloomgrowthcoach.com/coaches/trent-clark/ 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.

    Debt Free Is Not Financially Free, Joey Muré On Wealth Without Wall Street
  7. Sep 17

    Christine Blosdale, The EXPERT AUTHORITY Coach

    What does it take to become the person people recognize, trust, and turn to as the expert in your field? In this episode of Winners Find a Way, Coach Trent M. Clark sits down with Christine Blasdell, five-time #1 bestselling author, former broadcast journalist and radio host, and founder of Expert Authority Coach. Christine shares how entrepreneurs can stop hiding their expertise and start positioning themselves as a trusted authority. Her framework, The Expert Authority CODE, breaks the process into four key pillars: C — Clarity You need to be crystal clear about who you are, who you serve, and what you do. Christine explains that clarity isn't about trying to appeal to everyone. When you know exactly who you are and who you serve, you make it easier for the right people to recognize that you're the person they've been looking for. O — Ownership The next step is owning your expertise. Christine encourages entrepreneurs to recognize their talents, experience, skills, and accomplishments without confusing confidence with arrogance. You don't need to brag. You simply need to acknowledge what you're genuinely good at and confidently stand behind it. D — Delivery Expertise doesn't matter if nobody knows you have it. Christine talks about the importance of finding the right channels to communicate your message, whether that's: Podcasting Video Social media Writing a book Speaking Webinars and workshops Her message is simple: you have to be seen and heard in order to be trusted, and trust creates opportunities to get paid. E — Elevation Christine's final pillar is about recognizing and communicating the accomplishments you've already earned. She shares how she once overlooked her experience working for AOL and Microsoft MSN, even though those recognizable brands added significant credibility to her professional story. The lesson: Look back at what you've already accomplished. Some experiences that seem ordinary to you may be highly valuable to someone else. Don't Give Other People Your Power Christine also opens up about a difficult period in her broadcasting career when another host's behavior caused significant stress and made her consider leaving her career. She explains how changing her perspective helped her regain a sense of control and respond differently to the situation. Trent and Christine discuss how easily people can allow one negative comment, opinion, or criticism to influence their dreams. Whether you're an entrepreneur, athlete, creator, or professional, the message is clear: don't let someone else's opinion determine what you're capable of pursuing. Your Website May Be Losing You Business Christine also shares one practical marketing lesson every entrepreneur should consider: What happens above the fold on your website? You may only have a few seconds to capture someone's attention when they arrive on your website. Christine recommends using that valuable space to immediately communicate: Who you are What you do Who you help Why someone should trust you What action they should take next One of her favorite approaches is a short welcome video that lets potential clients see your face, hear your voice, and experience your personality and energy immediately. Instead of making visitors dig through pages of copy to understand what you do, make the message clear from the beginning. Key Takeaways Get clear about who you are, who you serve, and what you offer. Own your expertise without confusing confidence with arrogance. Find the communication channels that fit your strengths. Make your accomplishments visible instead of assuming people already know them. Don't allow someone else's criticism to define your potential. Your expertise needs to be seen and heard before people can trust it. Use the space above the fold on your website strategically. A short welcome video can communicate your personality and expertise faster than a long block of website copy. Look back at your experience—you may have more authority than you realize. About Christine Blasdell Christine Blasdell is an Expert Authority Coach, five-time #1 bestselling author, former broadcast journalist, radio producer and on-air host. With decades of experience in communication, broadcasting, podcasting, personal branding, and coaching, Christine helps entrepreneurs position themselves as trusted authorities in their industries. Her work focuses on helping experts become seen, heard, trusted, and paid. Connect with Christine Website: expertauthoritycoach.com Expert Authority Quiz: expertauthorityquiz.com Christine also offers a 30-minute coaching session designed to help entrepreneurs identify where they are now, where they want to go, and what steps can help them get there. About Coach Trent M. Clark Coach Trent M. Clark is a serial entrepreneur, leadership coach, speaker, and author of Leading Winning Teams. He spent more than 12 years coaching professional baseball, including experience with three World Series teams. Today, he helps leaders and organizations build winning teams and achieve greater growth. Website: coachtrent.com Listen & Subscribe If you enjoyed this episode, subscribe to Winners Find a Way and share this episode with an entrepreneur, leader, coach, or expert who needs to hear this message. Because winners don't just find a way— They build one.

    Christine Blosdale, The EXPERT AUTHORITY Coach
  8. Sep 11

    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
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.