My Favorite Mistake: Business Lessons from Failures and Success

How Culture Creates Freedom and Profit: Josh Cunningham Returns to Share His New Book

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

The Mistake of Unrealistic Expectations: Mark Struczewski’s Solopreneur Journey

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?

Avoiding Bad Marketing: Amber Gaige on Mistakes, AI, and the Four Cs

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?

TAKE TWO: Ballet, Mistakes, and Masked Performances: Jared Redick’s Story of Grace Under Pressure

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?

How a Mistake in Confronting Workplace Discrimination Shaped a Leadership Career – Karin Hurt on Speaking Up the Right Way

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?

What Nearly Killed Andrew Laws’ Business—and Why He’s Now Grateful for It

My guest for Episode #310 of the My Favorite Mistake podcast is Andrew Laws, Founder of the SEO agency Yeseo IO and host of The Business Amplifier Podcast. Andrew has been working in digital marketing for over 25 years and has seen just about every shift in the SEO landscape. But one of the biggest lessons of his career came not from Google’s algorithm, but from a catastrophic business event involving hackers, a two-year police investigation, and a decision that changed everything.
Episode page
Andrew shares the harrowing story of building a successful web hosting company—only to have it destroyed by cybercriminals just as he was preparing to sell it. The hackers didn’t just crash servers—they triggered legal threats, emotional exhaustion, and a complete shutdown of Andrew’s businesses at the time. But through that painful chapter, Andrew found clarity. He realized he had been doing too much alone and needed to build smarter, more resilient systems—and a team he could trust.
In our conversation, Andrew talks candidly about burnout, delegation, and how the right mistake can become a turning point. He also shares practical insights into what SEO really is (and isn’t) in 2025, why many people misunderstand Google’s algorithms, and why "doing good stuff" consistently still beats gimmicks and shortcuts. Whether you're a business owner, marketer, or just someone who's ever felt overwhelmed, Andrew’s story offers a timely reminder: the hardest setbacks can lead to the most meaningful resets.

Questions and Topics:
What’s your favorite mistake?
How did the hackers get in, and what did the police uncover?
Why did you shut down not just the hosting business but also your SEO company?
Did the hackers have a clear motive—was it ransom, malice, or something else?
What lessons did you learn about web hosting and digital security?
How did that experience affect your approach to business and leadership?
What did you do differently when launching Yeseo?
How do you now decide what to delegate versus do yourself?
What tools or systems help you delegate effectively?
How did you get into SEO in the first place?
What's the biggest mistake companies make when it comes to SEO?
How has SEO evolved, especially with the rise of AI?
Does Google penalize AI-generated content, or is quality still the priority?
Why does “snake oil” SEO still persist?
Tell us about your podcast, The Business Amplifier. Who is it for?
Who do you think is the greatest band of all time—and why?

How Busy Teams Can Better Execute Growth Plans: Andrea Jones on 'Executagility' and Mistakes

In this special bonus episode of My Favorite Mistake, Mark Graban talks again with Andrea Jones, Principal at AJC and CEO of The Executagility Company.
Andrea was previously featured in Episode 105, and she returns to discuss the release of her new book:The Executagility Field Guide: How Busy Teams Can Execute Growth Plans.
Andrea shares a new “favorite mistake” involving lost data from a Typeform survey—an honest example of learning the hard way how software design can trip up even experienced business leaders. The good news? She caught the mistake, learned from it, and adjusted her systems to avoid similar issues in the future.
We also dive into the four pillars of the Executagility model:
Alignment – Are we clear on the goals and priorities?
Available Time – Do our people realistically have capacity to execute?
Competence – Do we have the right skills in-house or need help?
Structure – Do we have a repeatable process to keep projects on track?
Andrea explains how she applied her own framework to the writing and launch of her book—and how it’s helping mid-sized businesses get growth initiatives done without burning out their teams.
"You can’t execute growth if your team is already stretched thin trying to handle today’s work."
"Just because someone’s capable in their current role doesn’t mean they can drive transformation alone. That’s why the glue person—the project leader—is essential."

Burnout to Breakthrough: How La Tonya Roberts Found Harmony by Leaving Corporate Consulting

My guest for Episode #309 of the My Favorite Mistake podcast is La Tonya Roberts, the founder and CEO of Harmony Consulting Group. La Tonya is a fractional COO, HR consultant, and executive coach who helps women entrepreneurs scale their service-based businesses from six to seven figures through systems, strategic planning, and operational excellence. Before launching her firm, she built her career at top consulting organizations like Deloitte and Booz Allen, where she developed deep expertise in organizational change and operational leadership.
EPISODE PAGE WITH VIDEO, TRANSCRIPT, AND MORE
In this episode, La Tonya shares her favorite mistake—staying too long in roles she had outgrown, taking on too much responsibility, and ultimately burning out. After experiencing both physical and emotional fatigue, including a dramatic moment that sent her to the hospital, she realized that her tendency to overfunction in high-demand environments was unsustainable. Those hard lessons eventually led her to rediscover joy in her work by launching her own business focused on operational harmony and intentional growth.
La Tonya explains how she now helps founders—especially women—build scalable, process-driven businesses without sacrificing their well-being. She also shares how she uses tools like ChatGPT to automate repetitive tasks and increase efficiency, both in her business and her clients'. We also talk about the importance of aligning systems, people, and strategy, and how La Tonya’s clients benefit from her experience in both large enterprises and nimble startups.
Listeners will hear practical advice on avoiding burnout, building systems that run without you, and why "work-life harmony" may be a better goal than elusive "balance."

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?

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 Episode 274, where he shared stories about leadership, learning from failure, and what it takes to protect athletes on the biggest stage in American sports.
This time, we’re following up on one of the most anticipated changes to NFL gameplay in years — the "dynamic kickoff" experiment launched in the 2024 season. Dr. Mayer shares the early results from this science-informed safety initiative, including a 43% drop in concussions on kickoffs, and an increase in returns that keeps the play exciting while protecting players.
We also explore:
Advances in helmet technology and guardian caps
The NFL's “guardian-cap optional” equipment path forward
How Dr. Mayer and his team use a systems approach to mitigate — not eliminate — risk in a high-impact sport
Thom reminds us that “the work continues” — a mantra that applies to sports, healthcare, and any field where safety and excellence are the goal.
🎧 Listen now and catch up on his original episode here🌐 Learn more about Dr. Mayer and his work with the NFLPA💡 Subscribe at MarkGraban.com/mistake