My Favorite Mistake: Business Lessons from Failures and Success

• Mistakes vs. 'Stupidity': C.J. Stewart Breaks Down Life Lessons from Baseball to Social Justice

  My guest for Episode #308 of the My Favorite Mistake podcast is C.J. Stewart, co-founder and Chief Visionary Officer at the LEAD Center for Youth, an Atlanta-based nonprofit focused on empowering Black youth through sports-based development. Before dedicating his life to mentorship and advocacy, C.J. was drafted twice by the Chicago Cubs and built a successful career as a professional hitting instructor and co-owner of Diamond Directors. He’s also the author of Living to Lead: A Story of Passion, Purpose, and Grit. Episode page with video and more C.J.’s “favorite mistake”? Becoming an avid runner. What started as a tribute to the life of Ahmaud Arbery turned into a transformational habit—one that reshaped his health, mindset, and mission. In this powerful conversation, C.J. unpacks the difference between mistakes and stupidity, explores the struggles that shape significance, and reflects on the emotional toll and systemic barriers faced by Black athletes. He also shares how running has helped him connect across generations, communities, and cultures. Throughout the episode, C.J. offers a candid and thought-provoking look at racism, leadership, and the need for real advocacy—not just good coaching. He shares insights from his own life as a player, coach, and nonprofit leader, challenging listeners to consider how we name and respond to problems, and why protecting others is at the heart of leadership. This is a conversation about growth, conviction, and using our platforms to make a difference. Questions and Topics: What’s your favorite mistake, and what did you learn from it? In what way was becoming a runner a mistake? How do you define the difference between a mistake and stupidity? How has running changed you—physically, emotionally, and socially? Did pursuing a career in professional baseball feel like a mistake in hindsight? What does LEAD stand for, and what is its mission? Why is advocacy more important than just good coaching? Why do you think there are so few Black players in certain positions, like catcher or pitcher? What needs to change in baseball to address racism and systemic barriers? What do you mean when you say you became “openly Black” in 2015? How does racism take an emotional toll on Black athletes, even those who succeed? Are MLB diversity programs effective, or are they falling short? What else needs to happen to create real change and equity in baseball?

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• How the NFL Is Reducing Head Injuries Without Losing the Kickoff: A Conversation with Dr. Thom Mayer

  In this bonus episode of My Favorite Mistake, host Mark Graban welcomes back Dr. Thom Mayer, the longtime Medical Director for the NFL Players Association. Thom previously joined us in catch up on his original episode here 🌐 Learn more about Dr. Mayer and his work with the NFLPA 💡 Subscribe at MarkGraban.com/mistake

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• Selling Books Isn’t the Publisher’s Job: Terry Whalin What Authors Must Learn Early On

  My guest for Episode #307 of the My Favorite Mistake podcast is Terry Whalin, an accomplished editor and author of more than 60 books, several of which have sold over 100,000 copies. Terry is the owner of Whalin and Associates, a communications firm, and he serves as an acquisitions editor for Morgan James Publishing. Drawing from decades of experience in both writing and publishing, Terry shares a favorite mistake that changed the course of his career—offering valuable insights for first-time authors and seasoned professionals alike. Episode page with video and more His most recent book is 10 Publishing Myths: Insights Every Author Needs to Succeed. Terry’s favorite mistake took place in 2007, when a high-profile publishing event jolted him into realizing just how little he was doing to promote his own books. Despite having secured multiple six-figure advances and a long list of published titles, Terry was receiving negative royalty statements—his books weren’t earning out. That wake-up call led him to take what he calls 100% responsibility for his own success, adopting a daily commitment to book promotion, content creation, and building an online presence. From that turning point, he launched a blog (now with over 1,700 posts), grew a substantial social media following, and became a consistent voice in the author education space. In the conversation, Terry and Mark explore the myths and realities of book publishing—especially the misconception that a publisher will handle marketing. Terry outlines how today’s authors must become active promoters, the importance of building an email list you control, and why giving away ebooks can actually drive print book sales. He also shares hard-earned lessons about evaluating publishers, avoiding scams, and understanding how traditional and independent publishing models differ. Whether you’re writing your first book or navigating your next launch, Terry’s insights are a masterclass in professional ownership and long-term thinking. Questions and Topics:   What’s your favorite mistake? Was it just a bad assumption to think publishers would promote your book, or do they sometimes mislead authors? Is the idea that a publisher will handle marketing one of the common myths in publishing? What specific actions did you start taking after realizing you needed to take full responsibility for your book’s success? Are you actively guesting on podcasts and using social media today to promote your work? Do social media efforts actually help sell books—or is it more about visibility and exposure? What’s your take on claims like “#1 Amazon bestseller”—do those really help authors sell books? Can you explain how the Morgan James model differs from traditional publishing? Why do you ask authors to commit to buying 2,000 copies of their own book? What role does giving away ebooks play in driving print sales? What should authors consider when deciding between traditional, hybrid, or independent publishing? How can aspiring authors avoid getting scammed by predatory publishing companies? What’s the role of an acquisitions editor, and how do you evaluate submissions? Do pre-orders really matter for bookstore placement? Why should authors consider writing for magazines or newspapers to build their platform? Do you think authors give up too early on marketing their books? Is building an email list still essential for authors, even in the age of social media? Should authors be cautious about relying too much on platforms like Facebook or LinkedIn?

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• Losing Her Best Employee Was the Wake-Up Call Betsy Pepine Needed to Reinvent Her Real Estate Company

  My guest for Episode #306 of the My Favorite Mistake podcast is Betsy Pepine, a serial entrepreneur in real estate and the founder of Pepine Realty. Betsy leads a top-producing real estate team consistently recognized by The Wall Street Journal and has built a family of companies that includes a property management firm, title company, real estate school, and a nonprofit. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE She’s also the author of the 2024 book Breaking Boxes: Dismantling the Metaphorical Boxes That Bind Us, which explores the limiting labels and roles we assign ourselves—and how to break free from them. Betsy’s favorite mistake was starting her brokerage with no clear plan. What began as a solo effort out of her home unexpectedly turned into a team, and eventually a company—but without intentional structure or culture. That all came to a head when her trusted assistant resigned right before a long-overdue family vacation. Her assistant’s honest feedback—about the lack of family, growth, and purpose—was a painful but pivotal wake-up call. Betsy responded not by retreating, but by reading leadership books on her cruise, hiring a coach, and reinventing her company with clear values and a defined mission. In our conversation, Betsy shares how she rebuilt Pepine Realty around core values like family, impact, and growth. She talks about initiatives like creating a nonprofit to address housing affordability and designing career paths that include a rare salaried-agent model in real estate. We also discuss the power of learning from mistakes—including how her team shares “learnings” each week in a psychologically safe environment that accelerates growth and prevents repeated errors. Betsy’s story is about far more than real estate—it’s about leadership, self-awareness, and responding to failure with action. Her perspective will resonate with anyone building a team or culture where people feel seen, supported, and inspired to improve. Questions and Topics: What’s your favorite mistake? What did your assistant say when she resigned—and how did that become a turning point for you? How did you respond to that feedback, and what changes did you make in your business? What were the first steps you took to start shaping your company culture? Did you create your mission and core values on your own at first? How did you define and build a “sense of family” inside your business? What inspired you to create a nonprofit—and how does it fit into your overall mission? What’s the purpose behind your unique salaried agent role? How do you help team members shift roles if they’re not in the right seat? What’s the weekly “learnings” segment in your team meeting—and how does it support growth? How do you balance encouraging learning from mistakes without being careless? Do you use checklists or systems to help prevent mistakes? What prompted you to write Breaking Boxes, and what’s the core message of the book? How do we recognize when we’re stuck in a metaphorical box—and how do we step out of it? What are the main fears that keep people in those boxes? Can you share how fear of failure has influenced your thinking over time? What does it take to build resilience to change? What’s your approach to managing fear of loss—especially status or social connections? How did your connection with Barbara Corcoran come about? What lessons have you learned from Barbara as a mentor? What advice would you give someone thinking of starting a business without a clear plan? What do you think are the best reasons for someone to get into real estate? How do you view the role of a real estate agent during high-stress life transitions? How do you create consistency in values across your family of companies? How do you support women reentering society after incarceration—and what’s the deeper “why” behind that work?

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• How a ‘Happy Mistake’ Led to a Leadership Journey in ADHD Education — John Willson of SOAR

  My guest for Episode #305 of the My Favorite Mistake podcast is John Willson, Executive Director of SOAR, the world’s premier outdoor adventure program serving youth with ADHD and learning disabilities. Episode page with video and more With over 30 years of experience, John is a passionate advocate for experiential education and life skills development through structured, strengths-based environments. SOAR, which stands for Success Oriented Achievements Realized, supports young people ages 8 to 25 through summer camps, boarding schools, and gap year programs focused on building confidence and resilience. John’s favorite mistake took place on Mount Katahdin, the northern end of the Appalachian Trail, where he unknowingly summited a false peak in poor weather conditions. Faced with a difficult decision—turn back through a dangerous route he already knew or forge ahead into unknown terrain—he pressed on despite worsening conditions. Although it was arguably the “wrong” decision in the moment, it led to a powerful sense of accomplishment and a safer descent than expected. John describes this as a “happy mistake” that taught him about risk, perseverance, and the sometimes unexpected rewards of pressing forward. In our conversation, John shares how this philosophy of “failing forward” underpins SOAR’s mission. He explains how their structured programs help kids with ADHD and learning differences build critical life skills, develop self-awareness, and form friendships—often for the first time. We also explore the importance of creating environments where neurodiverse individuals are supported, understood, and encouraged to take safe risks, with a strong network behind them. John and I also discuss the evolving understanding of ADHD, the challenges of diagnosis, and how labels matter less than building strategies that work. He shares practical advice for parents and adults alike, emphasizing the role of support systems, coaching, and compassion. Whether you’re a parent, educator, or someone navigating your own neurodiversity, this episode offers insights into how mistakes—when supported by reflection and community—can lead to breakthroughs. Questions and Topics: What’s your favorite mistake? Is it true that one of your most common mistakes is people misspelling your last name? Did you go back and climb Mount Katahdin again on a clearer day? What do you mean by “summit fever”? If that decision had led to a bad outcome, would it change how you reflect on it? What lessons did you take away from that pattern of decision-making? What are some ways the SOAR summer camp is tailored for kids with ADHD or learning disabilities? How much of the benefit comes from being with other kids who share similar strengths and challenges? How does being in that kind of environment help kids feel more accepted? How does SOAR help kids who struggle to make friends build relationships? When were you diagnosed with ADHD? How did that diagnosis shape your connection to SOAR and the work you do? How many SOAR staff members also have ADHD, versus being trained to support it? What kind of person tends to thrive on your staff? What’s your take on people wondering if they have ADHD or if it’s anxiety or something else? What matters more—getting a diagnosis or developing the right coping strategies? What advice would you give someone recently diagnosed with ADHD—or who suspects they might have it? Can you talk about the role of support systems in success for neurodiverse individuals? What’s your view on younger people being more open about neurodiversity in the workplace? Can you share some practical first steps after receiving an ADHD diagnosis? Why is identifying your support network such a crucial part of success?

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