My guest for Episode #328 of the My Favorite Mistake podcast is Emily Aborn, a small business copywriter, speaker, and host of the Small Business Casual podcast. Episode page with video, transcript, and more Emily helps entrepreneurs bring clarity, creativity, and authenticity to their marketing. Before finding her true calling, she owned a brick-and-mortar organic mattress store—a business that looked great on paper but didn’t align with her passions or strengths. Emily shares how this “perfect-on-paper” business became her favorite mistake. Though the store was profitable, she found herself feeling trapped, unfulfilled, and disconnected from the work she truly loved. Through closing that chapter, Emily discovered what she actually enjoyed most—writing, connection, and storytelling—and turned those insights into a business built around her natural skills. Today, Emily works with entrepreneurs across industries to find their authentic voice and create meaningful marketing. In this episode, she and Mark explore lessons about self-awareness, alignment, and how mistakes can guide us toward a more fulfilling path. Emily also shares practical insights on copywriting, understanding your audience, and why genuine collaboration beats fear-based marketing every time. Questions and Topics: What was your favorite mistake, and what did you learn from it? Why did that business seem like such a good idea on paper? What made you realize it wasn’t the right fit? How did running that store help you discover your passion for copywriting? What were some of the marketing lessons you learned from that experience? What are the most common copywriting or branding mistakes you see small businesses make? How can business owners find and express their authentic voice in their marketing? What are “problem-aware,” “solution-aware,” and “symptom-aware” customers—and why does that matter? How do you approach repurposing content the right way instead of just copying and pasting? What has hosting your own podcast taught you about communication and creativity? Have you ever made a memorable mistake as a podcaster yourself?
My guest for Episode #327 of the My Favorite Mistake podcast is Dr. Maya Ackerman, AI pioneer, researcher, and CEO of WaveAI. She’s also an associate professor of Computer Science and Engineering at Santa Clara University and the author of the new book Creative Machines: AI, Art, and Us. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE In this episode, Maya shares her favorite mistake — one that changed how she builds technology and thinks about creativity. Early in her journey as an entrepreneur, her team at WaveAI created an ambitious product called “Alicia,” designed to assist with every step of music creation. But in trying to help too much, they accidentally took freedom away from users. That experience inspired her concept of “humble AI” — systems that step back, listen, and support human creativity rather than take over. Maya describes how that lesson led to their breakthrough success with Lyric Studio, an AI songwriting tool that empowers millions of artists by helping them create while staying true to their own voices. She also shares insights from her research on human-centered design, the philosophy behind generative models, and why we should build AI that’s more collaborative than competitive. Together, we discuss why mistakes — whether made by people or machines — can spark innovation, and how being more forgiving toward imperfection can help both leaders and creators thrive. “If AI is meant to be human-centric, it must be humble. Its job is to elevate people, not replace them.” — Maya Ackerman “Who decided machines have to be perfect? It’s a ridiculous expectation — and a limiting one.” — Maya Ackerman Questions and Topics: What was your favorite mistake — and what did you learn from it? What went wrong with your second product, “ALYSIA,” and how did that shape your later success? How did you discover the concept of “humble creative machines”? What makes Lyric Studio different from general AI tools like ChatGPT? How do you design AI that supports — rather than replaces — human creativity? What’s the real difference between AI and a traditional algorithm? How do you think about ethical concerns, like AI imitating living artists? What do you mean by human-centered AI — and how can we build it? Why do AI systems “hallucinate,” and can those mistakes actually be useful? How can embracing mistakes — human or machine — lead to more creativity and innovation? What are your thoughts on AI’s future — should we be hopeful or concerned?
My guest for Episode #326 of the My Favorite Mistake podcast is Dr. William Harvey, a manufacturing executive and university professor whose career is defined by developing people, strengthening systems, and driving organizational excellence. A proud U.S. Marine, William carries forward a deep tradition of service and leadership. He also serves as the chair for the 2026 AME International Conference in Milwaukee, hosted by the Association for Manufacturing Excellence (AME). EPISODE PAGE WITH VIDEO AND MORE William shares a powerful early-career story about a mistake that taught him lasting lessons about trust, humility, and psychological safety. When he accidentally derailed a customer order by taking home the wrong document, he feared the worst. Instead, his manager’s calm and compassionate response—and a customer’s extraordinary effort to make things right—changed how William thought about leadership forever. Over time, William applied those lessons to how he leads teams and builds culture. He believes that leaders go first—by admitting mistakes, showing vulnerability, and creating space for others to experiment, fail, and learn. Through daily coaching cycles and methods like Toyota Kata, he helps people develop confidence in problem solving and take ownership of improvement. His goal: to build a workplace culture rooted in trust, respect, and continuous learning, where every person feels safe enough to speak up and strong enough to lead. Key Lessons & Themes: Why trusting your team is critical to avoiding unnecessary errors How supportive leadership responses turn mistakes into growth moments The connection between psychological safety, continuous improvement, and Toyota Kata How to “go first” as a leader—admitting your own mistakes to build trust The link between physical safety and psychological safety in world-class organizations What leaders can learn from Paul O’Neill and his “zero incidents” mindset at Alcoa
In this bonus re-release, we revisit an important and timely conversation with Sabrina Moon, Founder and CEO of The Problem Solving Institute and a certified Dare to Lead™ facilitator. Originally aired as Episode #35 of My Favorite Mistake, this conversation remains one of the most powerful and honest reflections on leadership, shame, and transformation. Episode page with transcript and more 🔍 What You’ll Hear: Sabrina’s “favorite mistake” — using shame as a leadership tool in high-stress environments The culture of command-and-control leadership she inherited (and how she broke the cycle) How Brené Brown’s work on vulnerability and shame helped her lead differently The personal toll of shame-based leadership — on her team and herself Why self-awareness is a skill—and how we can build it The role of grace, compassion, and curiosity in becoming a better leader “We use shame and the fear of shame to motivate, but I think in an unhealthy way. I would utilize shame because it was the last tool in my toolbox and I was desperate.” — Sabrina Moon 👤 About Sabrina Moon: Sabrina is a leadership coach and consultant who helps organizations move from reactive command-and-control cultures to psychologically safe environments where continuous improvement and innovation can thrive. Connect with her at ProblemSI.com or on LinkedIn. ✨ Why Re-Release This Episode? As more organizations reflect on how culture impacts performance, engagement, and well-being, this episode offers essential insights for leaders at every level. Whether you're managing a team or transforming a system, Sabrina's story reminds us that who we are as leaders matters just as much as what we do.
My guest for Episode #325 of the My Favorite Mistake podcast is Phillip Cantrell, EVP of Strategy at United Real Estate, founder of Benchmark Realty, and author of Failing My Way to Success: Lessons from 42 Years of Winning and Losing in Business. EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE Phillip reflects on more than four decades of entrepreneurial ups and downs across printing, real estate, and related ventures. He openly shares how devastating mistakes—including putting “all his eggs in one basket”—forced him to reinvent his approach. What looked like a catastrophe in 2007–2008 became the turning point that fueled Benchmark Realty’s rapid growth to nearly 2,000 agents. “Failure is going to happen. If you don’t make mistakes, you’re not doing anything.” In this conversation, Phillip and I talk about the difference between scaling vs. scrambling, the dangers of playing “not to lose” instead of “playing to win,” and why documenting processes is essential for growth. He also explains why your only real competitor is “the man in the mirror” and how daily reflection helps him learn from mistakes and avoid repeating them. This episode is packed with timeless lessons on leadership, resilience, and learning from failure—whether you’re in real estate or any other industry. “If you play not to lose in business, you’re already losing.” Questions and Topics: What’s your “favorite mistake” from your career? How did putting “all your eggs in one basket” impact Benchmark Realty? What did you learn from losing agents and clients during the mortgage crisis? How did you develop the flat-fee brokerage model, and what risks did you see at the time? Did you ever doubt whether that new model would work? How did you rebuild Benchmark from five agents to nearly 2,000? Why is it important to look outside your own industry for best practices? What do you mean by the difference between scaling and scrambling? How does documenting processes create better outcomes? Why do you say your only real competitor is “the man in the mirror”? What role has reflection and journaling played in your leadership growth? What advice would you give younger entrepreneurs about learning from mistakes?
In this very special solo episode of My Favorite Mistake, Mark Graban breaks down the gloriously ridiculous — and surprisingly instructive — mistakes made by the characters in his all-time favorite film, This Is Spinal Tap. With the long-awaited sequel, Spinal Tap II: The End Continues, now in theaters, Mark explores why Spinal Tap endures not just as a cult comedy classic, but as a brilliant satire of human behavior, team dysfunction, communication breakdowns, and leadership gone sideways. And yes — these mistakes still matter, even four decades later. From the Stonehenge measured in inches… To the foil-wrapped “courgette” in the pants… To the pod that wouldn’t open and the drummers who keep dying… …these moments are funny because they’re true. And they’re great reminders that how we respond to mistakes matters more than pretending they never happened. 🔑 Topics & Highlights: Why This Is Spinal Tap is more than just a comedy The iconic “Stonehenge” prop mistake and what it teaches us about communication How real-life rockstars refused to drum in the sequel (because of the “curse”) Why remembering the courgette as a cucumber is itself… a mistake The brilliance of “We don’t have time for that” and the backstage loop in Cleveland Why doing what you’re told isn’t the same as doing what’s right Mark’s personal story of seeing the film 100+ times — starting with a VHS in high school 🔗 Mentions & Links: 🎬 This Is Spinal Tap on IMDb 🎥 Spinal Tap II: The End Continues – Now in Theaters 📘 The Mistakes That Make Us by Mark Graban 💻 SpinalTarp.com – A curated list of character mistakes from the film 🎧 Subscribe & Follow: If you enjoyed this episode, make sure to subscribe, leave a review, and check out past episodes of My Favorite Mistake — where we talk to leaders, authors, entrepreneurs, and creatives about the mistakes that made them who they are. 🎙️ Listen on Apple Podcasts, Spotify, or wherever you get your shows.
My guest for Episode #324 of the My Favorite Mistake podcast is Trevor Schade. Episode page with video, transcript, and more Trevor began his career as a Lean Six Sigma Black Belt with a strong background in coding and process improvement. He consulted on business efficiency and outsourcing before shifting into real estate in 2008. After earning his license, he quickly built a top-performing team of 26 agents with zero turnover over five years. By leveraging a virtual admin team in the Philippines and innovative automation, Trevor’s group generated over a million dollars in commissions. In late 2023, Trevor stepped away from leading that large team to focus on investing, advising, and teaching. Today, he speaks on topics including negotiation, time freedom, and real estate strategy, and he has launched Life Wealth courses to help others pursue similar goals. In this episode, Trevor shares his favorite mistake: jumping into a multi-level marketing business at age 19. The venture wasn’t financially successful, but it transformed his mindset. For the first time, Trevor developed a daily reading habit that exposed him to classics like Dale Carnegie’s How to Win Friends and Influence People and Robert Kiyosaki’s Rich Dad, Poor Dad. Those books gave him a foundation in psychology, leadership, and long-term thinking that continues to influence his work. We also explore: How lessons from Nebraska football and martial arts shaped Trevor’s resilience What Lean Six Sigma taught him about efficiency, quality, and leadership Why he focused on psychological safety and belonging to keep his team intact How he used outsourcing and automation to scale without burnout The importance of setting trajectories instead of rigid goals in business and life Trevor’s story is a reminder that sometimes the most unprofitable ventures provide the richest education — if we’re willing to learn from them. Questions and Topics: What’s your favorite mistake? How did joining a multi-level marketing company at 19 shape your growth, even if it wasn’t financially successful? Did you ever think about leaving earlier, and was staying too long its own mistake? What lessons did you take from Nebraska football and sports about resilience and bouncing back? How did you first get into Lean Six Sigma and continuous improvement work? In what ways did Lean and coding skills help you scale your real estate business? What did you learn about leadership from running a 26-agent team with zero turnover? How did you create a culture of psychological safety and belonging for your team? Why do you emphasize inspiring people instead of “beating them over the head with metrics”? What role have outsourcing and automation played in your business success? You’ve said you set trajectories instead of rigid goals — what does that mean in practice? Looking back, how do you connect these mistakes and lessons to your current focus on investing, advising, and teaching?
In this special episode of My Favorite Mistake, host Mark Graban celebrates the kickoff of football season with a unique perspective: five legendary kickers who know what it means to perform under pressure. Guests include former NFL kickers Jay Feely, Shane Graham, David Akers, Nick Lowry, and University of South Carolina’s all-time leading scorer Parker White. These athletes share their most memorable mistakes and high-pressure moments—from Jay Feely’s infamous game-losing kicks and Saturday Night Live parody, to Shane Graham’s insight that failure and success are inseparable, to Nick Lowry’s persistence after 11 rejections before making the NFL. David Akers reflects on striving for improvement over perfection, while Parker White explains how practice and faith helped him overcome nerves and pass lessons on to the next generation. Across their stories, a common theme emerges: mistakes don’t define you—they prepare you. By reframing failure, focusing on fundamentals, and staying mentally strong, these kickers transformed pressure into performance. Their lessons reach far beyond football, offering wisdom for leaders, teams, and anyone facing high-stakes challenges in business or life. If you’ve ever struggled with fear of failure, performance anxiety, or the pressure to succeed, this episode offers practical, inspiring insights from athletes who’ve been tested in front of millions.
My guest for Episode #323 of the My Favorite Mistake podcast is Grace Bourke, Consulting Director of the Performance Excellence Practice at Baker Tilly. With nearly 40 years of experience in healthcare quality improvement and industrial engineering, Grace has worked in clinical care, biotech, global public health, and senior leadership roles at organizations including Kaiser Permanente and Sutter Health.' Episode page Grace shares a very personal favorite mistake — the challenges of building a new home that turned into a nightmare of mold, leaks, and structural flaws. What began as a house problem quickly became a more profound lesson in trust, verification, and speaking up — themes that resonate far beyond construction and directly into the world of healthcare. “Trust and verify becomes trust and vigilant, educated verification.” – Grace Bourke She reflects on how her tendency to trust inspections and processes, while ignoring her own instincts, parallels what often happens in healthcare systems when leaders or staff don’t feel psychologically safe to raise concerns. Grace connects her experience to the importance of leadership accountability, patient safety, and continuous improvement, noting that healthcare still struggles to admit mistakes and act decisively to prevent harm. We also talk about the role of psychological safety, second opinions, and lifelong learning, both in our personal lives and in healthcare. Grace shares how hobbies like glass fusing remind her that safe spaces for experimentation and “planned mistakes” can strengthen resilience, creativity, and growth. “We can’t fix the whole world, but we can fix our small piece — and that makes a difference.” – Grace Bourke Questions and Topics: What’s your favorite mistake? Was the mistake choosing this builder, or not verifying inspections before closing? Why do you think you didn’t speak up more during the building process? How does this experience connect to psychological safety in healthcare? What have you learned about yourself from going through this? How do you put the house problems into perspective? Has the builder taken responsibility or apologized? What parallels do you see between this home-building experience and healthcare improvement? Why is it so hard for healthcare organizations to admit mistakes? What role does leadership play in creating safer systems? How do hobbies like glass fusing help you practice learning from mistakes? What do you mean by “the mistake you’re planning”? What gives you hope for improvement in healthcare, despite the challenges?
My guest for Episode #322 of the My Favorite Mistake podcast is Rob Dorgan, a multi-talented professional whose career path has taken him from paralegal to college professor, retail store owner, manufacturing company president, and now licensed massage therapist, certified yoga educator, meditation teacher, and astrologer. Rob is also the author of Awakening the Mystic: A Novel of Cosmic Love and Healing. Episode page with video and more His favorite mistake? Taking what was meant to be a short trip to Europe while working on his PhD — a journey that led him to never return to that academic track. Instead, it opened his eyes to a different pace of life, sparked a reassessment of what success meant to him, and ultimately set him on a more balanced and meaningful career path. In our conversation, Rob shares how that decision — which family and friends initially questioned — allowed him to escape burnout and embrace a life and career that integrates his passions for teaching, creativity, and well-being. He reflects on lessons learned from his “type A” years in academia and business, the importance of slowing down, and how yoga, meditation, and practical stress relief can improve both personal health and workplace culture. We also discuss his experience bringing these tools into corporate environments, where employees not only benefit individually but also feel more supported by their organizations. “Stress comes on so slowly that it becomes your normal — and you forget what life without it feels like.” That realization, Rob says, is what helped him see the deeper value of meditation and mindful living. We also talk about his book’s concepts — from the “five kleshas” in yoga philosophy to the idea of an “inner council” — and how self-awareness can help us navigate life’s choices. Whether you’re navigating a career change, seeking better work-life balance, or simply curious about practical ways to reduce stress, Rob’s story offers valuable insights and inspiration. Questions and Topics: What’s your favorite mistake? How did your trip to Europe during your PhD studies change your career path? Did you consider moving to Europe to teach in that more relaxed environment? What countries did you visit on that trip? How did you go from teaching to starting a retail store and then leading a manufacturing company? Did yoga and meditation help you become a better leader? How did your personal stress experiences influence how you led the company? How have attitudes toward workplace stress changed since the 1990s? How do you make meditation and stress relief practical for corporate settings? How do companies usually find and bring you in for corporate sessions? What types of people attend your retreats, and what do they take away? How did you personally discover the benefits of a consistent yoga practice? How can yoga and meditation help with stress-related physical issues? What are the “five kleshas” in yoga philosophy? How do those concepts connect to ego, attachment, and fear? What is the “inner council” in your book, and how does it work? How did your interest in astrology begin? How can knowing your “council leader” help you in life and work? How did you balance the drive to finish your book with avoiding stress? What’s your advice for building habits like meditation or yoga into daily life?
My guest for Episode #321 of the My Favorite Mistake podcast is Cynthia Kane, founder and CEO of the Kane Intentional Communication Institute and author of several books, including How to Communicate Like a Buddhist and The Pause: How to Keep Your Cool in Tough Situations. Cynthia shares a pivotal mistake from early in her life: letting other people’s opinions matter more than her own—especially after a college professor told her she’d never be a good writer. That moment stung, but it also eventually propelled her toward a path of mindfulness, self-trust, and transformational communication. Cynthia explains how her journey through loss, meditation, and Buddhist principles helped her develop a more intentional way of communicating—not just with others, but with herself. We explore how mistakes, reactivity, and emotional attachment can all be reframed through mindfulness and self-awareness. Cynthia offers practical tools for staying calm during high-stakes conversations, including pausing, resetting the nervous system, and learning to speak from an “empty place”—a state of clarity without judgment or reactivity. “Every mistake leads us to something better.” Throughout the conversation, we also unpack the difference between being nice and being kind, how communication impacts stress levels, and why helpful language is honest, kind, and necessary. Cynthia’s insights are especially valuable for leaders, teams, and anyone who wants to communicate more effectively under pressure. As she says, “Every mistake leads us to something better.” Questions and Topics: What’s your favorite mistake? When did you realize that listening to others more than yourself had become a pattern? How did the loss of your first love influence your journey of self-awareness and healing? What led you to start writing again after being discouraged? What is creative nonfiction, and how does it differ from other forms of writing? Did working with an editor bring up old doubts, and how did you manage that feedback process? How does Buddhism shape your view on mistakes? Does that mindset help you approach writing mistakes differently? How do you balance detachment from mistakes with still caring about your work? What does “communicating like a Buddhist” mean in everyday life? Can you give examples where helpful vs. hurtful language is more subtle? What’s the difference between being nice and being kind? How does changing our communication style help reduce stress? What inspired your newest book, The Pause? What’s an example of a workplace situation where not pausing leads to regret? What should someone do if they need a pause but the other person won’t allow it? How can we calm ourselves in the moment to respond more intentionally? What does it mean to respond from an “empty place”? What breathing techniques do you recommend in tough conversations?
🎙️ In this bonus episode of My Favorite Mistake, Mark Graban welcomes back Dr. Jen Heemstra, Charles Allen Thomas Professor and Chair of Chemistry at Washington University in St. Louis. Jen joins us to talk about her new book, Lab Work to Leadership: A Concise Guide to Thriving in the Science Job You Weren’t Trained For. She shares how the book was inspired by her favorite mistake—realizing that a research career in science unexpectedly came with a leadership role she wasn’t trained for. What began as a personal challenge turned into a passion for mentorship and a practical guide to help others in the sciences (and beyond) succeed as “accidental leaders.” 👉 Learn how Jen approached this transition, what others in academia and technical fields can take away, and why leadership training is essential—even if it’s not part of your job description (yet). 🧪 “People are counting on you to get this leadership thing right.” – Jen Heemstra 🔁 Listen to Jen’s original episode (#262) where she shares her favorite mistake: http://markgraban.com/mistake262 🎧 Listen to all episodes at https://www.markgraban.com/mistake
My guest for Episode #320 of the My Favorite Mistake podcast is Damon Lembi, CEO of Learnit, a live learning and development platform that has helped upskill over 2 million professionals. Episode page with video, transcript, and more A former college baseball player and now a two-time bestselling author, Damon shares the story of how youthful ambition and overconfidence led him to push Learnit into a rapid, unsustainable expansion during the dot-com boom. Despite his father’s cautious advice, Damon got his way—and then faced the harsh reality of a collapsing market and near bankruptcy. In our conversation, Damon reflects on the hard-earned lessons from that pivotal mistake, including the dangers of comparing yourself to others, the importance of thinking through worst-case scenarios (what he now calls “purposeful awfulizing”), and the humility required to be a “Learn It All” leader. His resilience and willingness to grow through adversity helped him guide Learnit not only through the early 2000s tech crash, but also through the 2008 recession and beyond. “If you’re always right, you’re not listening hard enough.” Damon shares how his background as a competitive athlete shaped his mindset around failure, feedback, and agility—traits that now inform how he builds his team and company culture. We also talk about his podcast, The Learn It All Podcast, where he continues learning from top authors, leaders, and changemakers. Damon’s story is a powerful reminder that mistakes can be an expensive—but invaluable—education. “Make new mistakes, learn from them, and move forward.” Questions and Topics: What’s your favorite mistake? How did you go from playing baseball to becoming CEO of Learnit? What lessons did you take from your baseball career into business? Did you ever regret turning down the chance to play minor league baseball? Was anyone cautioning you against overexpanding Learnit? What did you learn from that experience as a young CEO? How did you apply those lessons during the 2008 recession? How has your leadership style evolved since then? What does “being a Learn It All” mean to you? What kind of people do you look to hire and why? How do you balance vulnerability and confidence as a leader? What did you learn about receiving feedback from your time in sports? How do you avoid letting one failure affect your next decision or meeting? What’s the difference between failure and a mistake? Can you share more about your Learn It All podcast and what you’ve gained from it?
My guest for Episode #319 of the My Favorite Mistake podcast is Sapna Pieroux, award-winning author of Let’s Get Visible!, a branding consultant, and the founder of Inner Visions ID. Episode page with video, transcript, and more With a background spanning 20 years in media and experience working with major brands like Toyota, Sony, and L’Oréal, Sapna shares the defining mistake that led her to a new level of impact: believing that her great work alone would speak for itself. Early in her entrepreneurial journey, she hid behind a company logo and resisted putting herself out there—fearing criticism, judgment, and even considering a pseudonym for her book. In this honest and inspiring conversation, Sapna shares how she overcame those fears and the societal pressures—especially those that affect women and people of color—to stay small or silent. Through her own evolution, she discovered the power of personal branding and visibility, not just for business growth but for personal confidence. She now helps leaders and teams align their business and personal brands so they can show up with clarity, confidence, and credibility in a noisy world. We also explore common branding mistakes—like trying to DIY logos without strategy—and how Sapna’s signature “Do-Say-See” model helps entrepreneurs and professionals build trust and influence. Whether you're just starting out or trying to get unstuck, Sapna’s insights on visibility, imposter syndrome, and brand alignment will give you practical tools and thoughtful encouragement. Questions and Topics: Is branding more about how others see you—like a nickname—than what you say about yourself? What was your favorite mistake? How was hiding behind your logo hurting your business? How close were you to publishing your book under a pseudonym? Was your publisher encouraging you to publish under your real name? What do you now teach others about personal branding as a result of that mistake? Why do you think many women hesitate to talk about their accomplishments? How did red become such a key part of your brand? What are some early steps someone can take to build their personal brand if they’re nervous about putting themselves out there? What gave you more confidence to show up consistently? How did entering awards help you boost your visibility and credibility?
My guest for Episode #318 of the My Favorite Mistake podcast is Matthew Neal Davis, an attorney, entrepreneur, and author of the provocative book The Art of Preventing Stupid. Episode page with video and more Matthew is the founder and managing partner of Davis Business Law, which has grown more than 1,000% in six years, earning a spot on the Inc. 5000 list. In addition to running a multi-office law firm across several states, he’s also the frontman of a heavy metal band called Geriatric Steel. In this episode, Matthew shares how not fully recognizing the leadership lessons from his Eagle Scout experience early in his legal career became a favorite mistake—and how it shaped the way he leads his firm today. Matthew reflects on the hiring and leadership missteps that stemmed from overlooking those early lessons—particularly how applying Ken Blanchard’s Situational Leadership framework helped him better support team members through growth phases. He explains how understanding where someone is on the spectrum from “excited beginner” to “self-reliant high achiever” has transformed how he mentors attorneys and minimizes costly turnover. These insights, combined with structured systems and data dashboards, now fuel a high-performance culture rooted in learning and ownership. ...we have rituals around this. Every Wednesday is WINSday—we celebrate successes. Every Friday, we have a firm huddle where we talk about what kicked our butts that week. We put it all on the table. That’s how we learn. That’s how we build trust and improvement into the culture. We also talk about the core idea behind Matthew’s book: that most business problems come from one of three vulnerabilities—catastrophes, ignorance, or ill-discipline—and how leaders can build a "business immune system" to prevent them. From mismanaged Google Ads campaigns to ill-advised partnerships, Matthew brings humor and clarity to how we can all learn faster, prepare better, and focus on growth. His story is a compelling reminder that being proactive beats being reactive—and that embracing mistakes is the best way to strengthen your systems and your culture. Questions and Topics: What’s your favorite mistake? What did you overlook from your Eagle Scout experience that later became valuable in business? What specific mistakes did you make in those early years of running the firm? How do you apply situational leadership in your law firm? Can you share an example of helping someone move through that “frustrated learner” phase? What lessons from Scouting translate to business leadership? Did you ever think growing the firm beyond a solo practice was a mistake? What do you mean by “preventing stupid”? Can you explain your framework for categorizing business vulnerabilities? How do you distinguish ignorance from stupidity in business? What are examples of ill-discipline you’ve seen in your firm? Have you created checklists to avoid repeating mistakes? What is the Strong Protected Business System? How does your business immune system tool work? What do you mean by circular systems in business? How do you think about culture as your firm grows? Have you managed to avoid hiring narcissistic or toxic attorneys? How often do you get to play with your band, Geriatric Steel? Are your original songs available on Spotify or anywhere online?
My guest for Episode #316 of the My Favorite Mistake podcast is Davina Frederick, founder of Wealthy Woman Lawyer, host of the Wealthy Woman Lawyer Podcast, and a business coach who has helped women law firm owners scale their practices to seven figures and beyond. Episode page with video, transcript, and more In our conversation, Davina shares why going to law school—an unconventional move at age 38—turned out to be her favorite mistake. Despite building a successful litigation practice, she realized that the traditional lawyer lifestyle wasn’t aligned with her long-term goals or well-being. "I realized I didn’t want to spend the rest of my life sitting behind a desk or in a courtroom." After stepping away from her first firm, Davina leveraged both her marketing background and the painful lessons of burnout to build a second, more sustainable law practice. That experience—and the power of hiring business coaches—ultimately led her to launch her own coaching firm. Today, Davina specializes in helping women lawyers grow their firms with clarity, confidence, and systems that reduce overwhelm and create balance. We also dive into what it means to create a systems-driven law firm—and how that principle applies across professional services. From breaking the “grading papers” bottleneck to resisting perfectionism, Davina offers practical strategies for founders who are ready to scale without losing themselves in the process. Her journey is a powerful example of learning from mistakes, listening to your inner voice, and having the courage to change course. Questions and Topics: What’s your favorite mistake? Why do you see going to law school as a mistake? What was your career before law school? What inspired you to make law your second career? How did you come to the decision to leave your first law firm? What happened between your first and second law firms? Why did you choose to launch a virtual firm in 2011? How did others react to your decision to work virtually? What did you do differently the second time to avoid repeating mistakes? What does it mean to have a systems-driven law firm? How do you help lawyers stop being the bottleneck in their business? Can you share examples of systems you recommend, especially for marketing? How do you coach lawyers through the fear of hiring after a bad experience? What mindset shifts help women lawyers move past perfectionism and indecision? What led you to focus exclusively on coaching women law firm owners?
My guest for Episode #316 of the My Favorite Mistake podcast is Jim Schleckser, founder and CEO of The CEO Project. Episode page with video, transcript, and more Jim is a seasoned business leader, bestselling author, and trusted advisor to CEOs around the world. With experience spanning 42 countries and multiple industries, Jim has spent decades helping leaders grow their companies and think more strategically. He’s also the author of Great CEOs Are Lazy and Professional Drinking, and he’s a certified sommelier—something we get to at the end of the episode! In our conversation, Jim shares a formative early-career mistake—being too optimistic as a leader. His enthusiasm led to overpromising revenue, under-delivering on results, and ultimately damaging his credibility to the point where he had to leave the organization. Jim reflects on how he’s since learned to balance positivity with realism, buffer commitments, and truly listen to skeptics on his team. His story is a powerful reminder that leadership isn’t just about vision—it’s also about judgment, humility, and learning from painful experiences. We also dive into what it means to be an effective CEO, including why Jim says great CEOs are lazy. He shares how high-performing executives focus their time on removing bottlenecks, not micromanaging, and why a trusted CEO peer group can be a game-changing support system. Plus, for fellow wine lovers, we cap off the episode with a fun bonus: wine mistakes, how to order like a pro, and Jim’s best tip for getting the most out of a wine list. Questions and Topics: What’s your favorite mistake, and what did you learn from it? Can you share specific examples of how your optimism led to overcommitment or missed expectations? How did that mistake affect your credibility and position in the company? How have you learned to balance optimism with realism in leadership? What’s your approach to setting stretch goals versus achievable targets? How can unrealistic goals create dysfunction or unethical behavior in organizations? What’s the best way to avoid data manipulation and maintain integrity in performance reporting? What is The CEO Project, and how does a CEO peer group provide value to its members? You say “great CEOs are lazy”—what does that really mean, and how does it work in practice? How can CEOs identify the biggest constraint or bottleneck in their business? Why do some CEOs struggle to admit mistakes, and how does that affect their leadership credibility? How do peer groups foster psychological safety for leaders? What inspired you to become a certified sommelier? What are some common mistakes people make when ordering wine? What’s your best tip for confidently ordering wine at a restaurant? If someone only drinks Napa Cabernets, what’s a good way to branch out? Have you observed gender bias in how sommeliers treat guests at the table?
My guest for Episode #315 of the My Favorite Mistake podcast is Kat Halushka, a business and visibility strategist for coaches, consultants, and speakers. She’s the founder of Profitable Impact Academy, where she helps entrepreneurs grow their audience, automate marketing, and land clients through speaking and streamlined funnels. EPISODE PAGE Kat’s favorite mistake? She followed the classic advice to “go to networking events and have coffee meetings” to get clients—so she did, hundreds of times. But after exhausting herself with back-to-back coffee chats every Friday, she realized the ROI just wasn’t there. Kat had a breakthrough when she nervously gave a short talk at a networking event—and walked away with two new clients that day. That lightbulb moment launched her on a mission to get in front of the room instead of meeting people one-on-one. Over time, she built her credibility by hosting her own events, attracting hundreds of attendees and growing a thriving business community. This shift helped her discover that strategic speaking, not endless small talk, was the true key to visibility and client conversion. Today, Kat teaches entrepreneurs to stop chasing every opportunity and instead focus on clarity, messaging, and scalable systems. She shares powerful lessons on why most new speakers fail to connect—and how you can avoid those pitfalls by making offers that speak to your audience’s present-day pain points. Whether you’re brand-new to business or looking to scale with less hustle, Kat’s insights on visibility, messaging, and mistake-making will help light the way forward. Questions and Topics: What’s your favorite mistake? How did those endless coffee meetings affect you and your business? What changed after that first speaking engagement? How did you start landing more speaking opportunities after that breakthrough? What was the origin story behind Profitable Impact Academy? What are some of the most common mistakes entrepreneurs make when trying to grow through speaking? How can business owners get clearer on what their audience really needs? Why is it a mistake to create too many offers or talks? How do you help clients identify and refine the one talk that drives results? What are the differences between speaking as a business vs. speaking to grow a business? When offered a speaking fee, how do you decide whether to accept or negotiate for something else? Can you explain what you mean by making an “offer from the stage”? How do you structure a win-win-win when working with event organizers? What’s one way speakers can make a compelling call-to-action without sounding salesy? Can you give an example of a “gift” that actually gets audience engagement? What’s your final advice for new entrepreneurs or aspiring speakers?
In this special bonus episode of My Favorite Mistake, host Mark Graban welcomes back Josh Cunningham, founder and CEO of Rokrbox and guest from Episode 244. Josh returns to share insights from his brand-new book, Culture Is the Key: How to Unlock Massive Profits and Freedom. We dive into: How Josh built a culture-first company that’s thriving—even in a tough real estate market Why cutting costs doesn’t have to mean cutting people or quality The inspiration and process behind writing his book What it means to create a Five-Star Company Culture Josh also reflects on what he’s learned since his last visit, including the power of simplification, scaling with intention, and how purpose has driven Rockerbox's explosive growth. “Culture isn’t just a vibe—it’s the engine behind every result.” “We asked: What’s the least amount of work a person has to do to move the needle—and how can we reward them more for it?” 📕 Grab the book: Culture Is the Key is available now on Amazon and Barnes & Noble 🎧 Listen to Josh’s first episode: My Favorite Mistake #244 Subscribe for more stories about leadership, culture, learning from mistakes, and growth. 🔔 Don’t forget to like, comment, and share if this resonated with you! #CompanyCulture #Leadership #Entrepreneurship #SmallBusinessGrowth #JoshCunningham #Rockerbox #CultureIsTheKey #BusinessBooks #MarkGraban #MyFavoriteMistake #StartUpLife #FiveStarCulture #WorkplaceCulture #BusinessLeadership
My guest for Episode #314 of the My Favorite Mistake podcast is Mark Struczewski, also known as “Mister Productivity.” Mark is a Houston-based productivity coach, speaker, and host of The Mister Productivity Podcast, with over 1,300 episodes to his name. He helps overwhelmed professionals cut through distractions and focus on what truly matters. Episode page with video, transcript, and more But before becoming a go-to expert on focus and effectiveness, Mark made a classic entrepreneurial mistake: thinking that launching a website would instantly attract a stream of clients. Spoiler alert—it didn’t. Mark’s favorite mistake was stepping into solopreneurship with unrealistic expectations. After being fired from his corporate job in 2005 and officially launching his business in 2011, he quickly found himself burning money on coaches, conferences, and tools he didn’t need—without any real plan or payoff. The financial pressure eventually forced a mindset shift: instead of trying to do everything, he began focusing on the right things at the right time. That turning point not only saved his business—it became the foundation for his productivity philosophy. In our conversation, Mark shares hard-earned lessons about clarity, focus, and sustainable productivity. We explore how he helps clients move past the illusion of “busyness,” why joy is an essential ingredient for productivity, and why it’s okay to slow down or even stop when your body and brain need a break. Mark also offers insight into how he uses tools like ChatGPT to streamline content creation and why being intentional with time is more powerful than packing your schedule. Whether you're a solopreneur or leading a team, this episode will challenge how you define and pursue productivity. Questions and Topics: What’s your favorite mistake from your career so far? Where do you think your unrealistic expectations as a solopreneur came from? How did you decide to stick with entrepreneurship instead of returning to corporate life? What specific changes did you make to turn things around in your business? How did you learn to focus instead of trying to be everywhere online? What’s the difference between productivity and effectiveness in your view? How do you help clients decide what’s truly worth their time? Can you share your definition of productivity? How do you tailor your coaching to each client’s unique situation? Why is clarity such a central part of your productivity approach? What’s your advice for getting clarity when feeling overwhelmed? How do you define success without falling into the “always working” trap? What are your thoughts on rest, recovery, and avoiding burnout? Do you believe productivity levels naturally fluctuate day to day? How do you personally manage high- and low-energy days? How do you use LinkedIn and DMs to build real relationships? What’s your take on scheduling content in advance vs. staying spontaneous? Can you tell us about your new ebook and how you used AI to create it?