My Favorite Mistake: Business Lessons from Failures and Success

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?

My guest for Episode #313 of the My Favorite Mistake podcast is Amber Gaige, a marketing strategist, international bestselling author, and founder of Far Beyond Marketing. With over 20 years of experience, Amber helps entrepreneurs simplify their marketing and drive real results. She’s also the author of The Far Beyond Marketing Guidebook: Stop Being Duped by Bad Marketing, and the creator of the Four Cs of Effective Marketing Framework. In this episode, Amber shares her favorite mistake—spending more than a decade working in a large, multi-division family business. While the experience taught her resilience, leadership, and business fundamentals, she reflects on how staying too long delayed her ability to find her own voice and build something truly independent. She opens up about the emotional complexity of leaving, the pressure of navigating work and family, and how that leap led her to grow—and eventually sell—a marketing business that launched her next chapter. We also discuss common mistakes businesses make when it comes to marketing, especially when selecting agencies or falling for one-size-fits-all tactics. Amber highlights the importance of clear messaging, knowing your ideal customer, and embracing AI wisely—without letting it replace human insight. Her story is one of tenacity, self-discovery, and servant leadership—a valuable listen for any entrepreneur or leader navigating growth, branding, or family dynamics. Questions and Topics: What’s your favorite mistake from your career? What kind of family business were you involved in? Did you choose to join the business, or was it more of an expectation? Was your initial role in the family business something you wanted? Did it feel like a mistake right away, or did that come later? Were you involved in marketing within the family business, or did you have to leave to pursue that? Were your parents both in leadership roles? And were you held to a higher standard? What was the process like for deciding to leave the family business? How did the opportunity to build and spin off your own marketing company come about? Was selling the business to private equity your exit strategy from the family business? How did you apply lessons from the family business to your new venture? What challenges come with hiring or firing family members in a business? How did you transition from operating under the family umbrella to running your own company? What does "Far Beyond Marketing" mean to you and your clients? What does servant leadership mean in the context of your work? Do you have any stories of helping clients recover from marketing mistakes? What are some common mistakes businesses make when hiring a marketing agency? What are some newer marketing mistakes you're seeing, especially related to technology? What’s a smart way to use AI in marketing—and what’s a mistake to avoid? Can businesses be penalized for publishing AI-generated content? How can business owners use a book as a strategic tool beyond just sales? What are your Four Cs of effective marketing? How do you define “brand” beyond just a logo? Is it possible for marketing firms to unintentionally mislead clients?

OOPS! Due to an editing mistake, I had to reupload the file. Again. My guest for Episode #312 of the My Favorite Mistake podcast is Jared Redick, a third-generation ballet dancer, choreographer, and award-winning educator. Episode page with links and more Jared is a full professor and Assistant Dean of Dance at the University of North Carolina School of the Arts. He has performed with renowned companies including the Boston Ballet and Miami City Ballet, and now shapes the next generation of dancers through his leadership, coaching, and innovation in arts education. In our conversation, Jared shares his favorite mistake—one that unfolded during the height of the COVID-19 pandemic while producing a filmed version of The Nutcracker. A critical planning misstep nearly derailed the production when sets weren’t ready for a pivotal weekend of shooting. Facing immense time pressure and logistical complexity, Jared and his team were able to regroup, adapt the schedule, and ultimately find a better way forward. The experience became a lesson in flexibility, communication, and leading with calm under pressure. Jared also reflects on his transition from performer to educator, how he defines effective leadership, and what it means to embrace vulnerability in pursuit of growth. We explore how his equity-focused curriculum changes are reshaping the world of ballet and how earning an MBA is helping him integrate business thinking into the arts. Throughout the episode, Jared’s humility, clarity, and passion for mentorship shine through. Questions and Topics: What’s your favorite mistake, and what happened during the COVID-era Nutcracker production? How did you lead your team through the anxiety of that situation and find a solution? Was the missed set deadline more of a communication issue or a planning breakdown? Were there lasting lessons from that project that apply to future productions? Was anyone blamed or punished for the mistake—or was it handled differently? What role does leadership play in preventing or responding to these types of issues? What stage of the pandemic were you in when filming The Nutcracker? Were dancers masked? Can you tell us more about your personal path into dance and your early training? How does the transition from high school conservatory to professional ballet typically work? How did you navigate your own transition from performing to teaching and leadership? As a performer, how did you deal with the possibility—or reality—of making mistakes on stage? How do performers balance self-assessment with celebrating what went well? Did you regularly receive feedback or review recordings of your performances? How has your leadership style evolved as an assistant dean and teacher? What are “equity-focused curriculum updates,” and how are they changing ballet education? What are some challenges in making ballet more inclusive and accessible? How does bias in dance differ from other performing arts like music? What has been most eye-opening in your MBA program coming from an arts background? How do business tools like project management software support the arts? What does “embracing vulnerability” mean to you, and how does it relate to learning from mistakes?

My guest for Episode #311 of the My Favorite Mistake podcast is Karin Hurt, CEO of Let’s Grow Leaders, a global leadership development firm. Karin is a former Verizon Wireless executive and the award-winning author of five books, including her latest, Powerful Phrases for Dealing with Workplace Conflict. Episode page with video, transcript, and more In this episode, she shares a deeply personal and professionally pivotal story from her corporate days—an impassioned confrontation over a discriminatory hiring decision that, while well-intentioned, caused serious damage to her career. Karin unpacks how her emotional reaction—rooted in a strong sense of justice—ultimately undermined her goal. Despite advocating successfully for her team member, her public and heated delivery hurt her leadership reputation. She reflects on the importance of staying calm under pressure, choosing the right time and place to speak up, and communicating with both courage and strategy. These lessons became the foundation for the work she does today, helping leaders navigate difficult conversations with confidence and compassion. Throughout the episode, we also discuss her transition from corporate executive to keynote speaker, author, and entrepreneur. Karin explains how she and her co-author (and husband), David Dye, help teams build cultures of “productive conflict,” where differences lead to innovation rather than division. From real-world mistakes to powerful communication tools, this episode is full of insight for leaders who want to lead with heart—and get results. Questions and Topics: What’s your favorite mistake, and what did you learn from it? Do you think the hiring manager eventually saw the light, or was the outcome driven by HR? Did that incident influence your decision to leave the corporate world and start your own company? How did your background in HR and operations shape your leadership approach? When did you realize you had something valuable to share publicly through your blog? How did your speaking career take off, and what was the turning point? How do you stay calm in conflict now, compared to earlier in your career? What are the four dimensions of productive conflict? How often do leaders get in trouble for what they say versus staying silent? How do you advise someone to say “no” to their boss without hurting their reputation? What are the dynamics of working with your husband as a business partner? How can teams embrace conflict as a source of innovation, not dysfunction? What’s the danger of trying to fix systemic conflict at the interpersonal level? How do you handle conflict on hybrid or global teams where trust is harder to build? Is it easier to de-escalate conflict in person versus virtual or text-based communication? How do you balance encouraging courage with creating psychological safety?