My Favorite Mistake: Business Lessons from Failures and Success

Nuggets of Advice from NBA Rookie Spencer Jones on Navigating NIL, Personal Branding, and Building a Legacy

My guest for Episode #293 of the My Favorite Mistake podcast is Spencer Jones, a rookie forward with the Denver Nuggets and a Stanford University graduate, where he earned a degree in Management Science and Engineering.
Episode page with links and more
He averaged 11 points per game over five standout years at Stanford, leading the Pac-12 in three-point shooting as a freshman and graduating as Stanford's all-time leader in three-pointers. Before college, Spencer also secured three high school state championships in Kansas.
While his professional basketball career with the Denver Nuggets keeps him on the court, Spencer's ambitions stretch far beyond the game. Passionate about the intersections of sports, health, and technology, he is actively building his brand in the health tech space, leveraging his platform as an athlete to explore innovation and make an impact off the court.
In this episode, Spencer shares his journey from high school state championships to becoming Stanford's all-time leader in three-pointers and his transition to the pros. Spencer opens up about his favorite mistake: hesitating to embrace the Name, Image, and Likeness (NIL) opportunities during his college years due to concerns about balancing individual branding with team dynamics. Reflecting on how this hesitation caused him to miss out on valuable opportunities early in his college career, Spencer explains how he learned to navigate those challenges and is now focused on capitalizing on his NBA platform while staying grounded in his basketball priorities.
Throughout the episode, we discuss Spencer's experiences balancing academics, athletics, and building a brand, including how his Management Science and Engineering degree from Stanford shaped his interest in the intersections of health, technology, and business. Spencer also offers insights into the evolving dynamics of NIL, the challenges of team equity, and the impact of the transfer portal. We explore his presence on LinkedIn as a platform for connecting with alumni and businesses, his passion for investments and startups, and how watching NBA superstar Steph Curry train influenced his own work ethic. Spencer's reflections provide valuable lessons on resilience, legacy building, and preparing for life after sports.

Questions and Topics:
What’s your favorite mistake?
Can you explain NIL (Name, Image, and Likeness) and the opportunities it offers athletes?
How did NIL impact team dynamics, and what was it like balancing individual and team priorities?
Did you consider transferring to another school, especially with the new transfer rules?
What lessons did you learn about balancing academics and athletics at Stanford?
Why did you choose Management Science and Engineering as your major?
What impact did being in Silicon Valley have on your development, connections, and career opportunities?
How much interest is there among players in investing, startups, and business ventures beyond basketball?
What kind of resources does the NBA or players' associations provide to help players prepare for their futures?
How does the G League (formerly D League) fit into player development for someone in your position?
What factors went into your decision to sign with the Denver Nuggets, especially as a two-way player?
How do you approach balancing short-term versus long-term decisions in your basketball and business career?
What led you to build a presence on LinkedIn, and how has that platform benefited you?
What advice do you have for other athletes about building their brand and preparing for life after sports?
How do you manage the pressure of potential mistakes in high-visibility situations like an NBA game?

Why Culture Is Your Secret Weapon for Success – A Conversation with Jessica Kriegel

My guest for Episode #292 of the My Favorite Mistake podcast is Dr. Jessica Kriegel, Chief Strategy Officer of Workforce and Labor at Culture Partners and an internationally recognized speaker. 
Episode page with video, transcript, and more
Known for her transformative 'Culture Equation,' Jessica has been featured on CNBC, MSNBC, CNN, and more. At Culture Partners, she leads pioneering research and strategy with Stanford University, working to reshape the DNA of Fortune 10 and 500 companies for long-term success.
Jessica holds a doctorate in Human Resources Development and Educational Leadership from Drexel University and is the author of Unfairly Labeled, a book that challenges generational stereotypes in the workplace. She also hosts the podcast "Culture Leaders," where she dives into the essence of true transformation.
In this episode, Jessica shares insights on leadership, culture transformation, and her unique journey through pivotal career experiences. Jessica discussed her favorite mistake—a whirlwind promotion at Oracle to Head of Strategy for the Head of Cloud, a role she describes as "seven promotions" above her current position at the time.
Although the experience quickly led to burnout due to overwhelming demands and a relentless work pace, it also became one of her most transformative learning experiences. Jessica credits those six intense weeks as the foundation for her "Culture Equation" framework, which she has since applied to drive organizational change and foster alignment between purpose, strategy, and culture.
The conversation also explored the critical role of leadership in shaping workplace culture and addressing challenges like burnout, disengagement, and generational stereotypes. Jessica emphasized that culture is fundamentally about how people think and act to achieve results, and leaders must align beliefs and behaviors to operationalize strategy. She shared her perspectives on overcoming employee disengagement, fostering innovation through psychological safety, and breaking free from generational labeling in the workplace.
Jessica also discussed her TED Talk, "How to Help People Give a Shit," highlighting how employees' perceived apathy often stems from overwhelm and a lack of agency rather than genuine disinterest.

Questions and Topics:
What’s your favorite mistake?
Would you say six weeks is an unusually fast burnout cycle?
Was the 3 a.m. call part of a broader pattern of disrespect or just a one-off incident?
Are these patterns common across organizations, or are they specific to individual leaders?
How do you define culture?
Did you face challenges getting your TED Talk title approved?
What advice do you have for leaders to address this challenge of employee disengagement?
How do you see leaders' perceptions of mistakes influencing workplace culture?
What led you to write your book Unfairly Labeled?
How do you think generational stereotypes impact workplace dynamics?
Do you believe evolving workplace expectations are driven more by technology than generational differences?

World Series Coach Trent Clark on Mistakes, Leadership, and Building Winning Teams

My guest for Episode #291 of the My Favorite Mistake podcast is Trent Clark, CEO of Leadershipity and Founder of Courage Coach LLC. Having spent his adult livelihood among the top 1% producers in sports and business, Trent is dedicated to empowering people to reach their goals, peak performance, and attain their dreams.
Episode page with transcript, video, and more.
An entrepreneur of 12 companies and longtime Entrepreneur Organization Member, he is best known for being a two-sport Division I Collegiate Athlete and Coaching 12 years in Professional Baseball with three organizations - including three (3) trips to the World Series - working with the Detroit Tigers, two-time American League Champion Cleveland Indians and the 2002 World Champion Los Angeles Angels of Anaheim. 
He’s the author of a new book, Leading Winning Teams: How Teamwork, Motivation, and Strategy Achieve Big League Success, and he’s also the host of his podcast, "Winners Find a Way."
Trent has worked on staff with famed personalities, coaches, and executives, including Nick Saban, Joe Maddon, Tom Izzo, Mike Scioscia, and my favorite from that list… Sparky Anderson.
This episode covers the importance of learning from mistakes, resilience, and the parallels between sports and business leadership. Trent shares impactful lessons from his career, including a pivotal mistake involving contract negotiations that shaped his approach to accountability and preparation.
The conversation explores themes such as embracing failure as a stepping stone to growth, the necessity of adaptability in high-pressure environments, and the role of coaching in fostering continuous improvement. Insights on balancing personal and professional commitments, the evolution of strength training in baseball, and cultivating high-performing teams round out a compelling discussion on achieving sustained success through intentional learning and reflection.

Questions and Topics:
What’s your favorite mistake?
Are you willing to share what the main promises were that the Angels made verbally but never included in the written contract?
Do coaches typically have an agent or a lawyer, or is that something you just handle on your own?
How has the thinking evolved about bulking up in baseball? Is it still considered risky, or is it more about how players approach strength training?
As a strength and conditioning coach, were you traveling constantly with both the Major League and minor league teams? What was that like for your family life?
What can we learn from athletes about bouncing back from mistakes that might apply to entrepreneurship or our own work?
You told me you get excited about mistakes—why is that, and how do people respond when you show that enthusiasm?

From Sports Executive to Entrepreneur: How Michelle Rankine Built a Multimillion-Dollar Home Care Franchise

My guest for Episode #290 of the My Favorite Mistake podcast is Michelle Rankine, Ph.D., a trailblazing entrepreneur in the health space who built a multimillion-dollar home care franchise business to address disparities in Black and Brown communities.
Episode page with video, transcript, and more
A former sports executive with roles at major organizations like the U.S. Olympic Committee, Michelle found her calling in senior home care after her brother’s tragic car accident left him paralyzed. Driven by a strong sense of purpose and community, she now owns three Right at Home franchises in the Dallas-Fort Worth area, prioritizing quality care and bridging critical gaps for aging adults.
In this episode, Michelle and host Mark Graban explore her biggest lessons learned: why trust is essential when building a business, how data-driven KPIs can spark growth, and where home care fits into the spectrum of healthcare services.
Michelle shares her personal story of shifting from the security of collegiate sports administration to the uncertainty of entrepreneurship, revealing how she discovered resilience, the importance of coaching, and the power of focusing on the right goals.
Key themes include fostering health equity, measuring what matters, and creating supportive networks—whether for Olympic athletes or for families needing respite care.

Questions and Topics:
Could you share your “favorite mistake,” and how did you learn from it?
Was your realization about needing to trust others gradual, or was there a clear wake-up call?
Which key KPIs helped you decide to step away from handling sales yourself?
How did your team respond when you began delegating more, and did you get any feedback about micromanaging?
What led you from a career in sports management to launching a home care business?
How do the resilience and focus you gained in athletics translate to entrepreneurship?
What are the biggest health disparities you aim to address, and how do your franchises help bridge those gaps?
Could you clarify the difference between ‘home care’ and ‘home health,’ and why does that distinction matter?
Why do some families wait too long to seek help, and how can people avoid that mistake?
What advice would you offer to adult children who find themselves caring for aging parents, especially when roles reverse?

Off for 2 Weeks; Special Kindle Book Price

I’m taking the next two weeks off, but I’ll be back with new episodes on January 6th.
 
Please check out the back catalog of episodes!
 
If you’re looking for something to read over the holidays, my book The Mistakes That Make Us: Cultivating a Culture of Learning and Innovation (that contains many stories and lessons learned from my guests… and my own career) is available for a special price — the Kindle format is just $2.99 (and equivalent prices around the world).
Visit Amazon in your country, or go to mistakesbook.com to learn more and to get a free preview.
Merry Christmas and Happy Holidays!

Lessons in Intellectual Property and Self-Trust with Plagiarism Expert Jonathan Bailey

My guest for Episode #289 of the My Favorite Mistake podcast is Jonathan Bailey, founder of PlagiarismToday.com. He’s also a Copyright and Plagiarism Consultant at CopyByte, with background and education in Journalism. 
Episode page with video, transcript, and more
He’s spoken at conferences worldwide, including four of the International Plagiarism Conferences, three SXSWi Conferences, and much more. He’s also been featured in countless publications, including The Boston Globe, The Guardian, PBS MediaShift, The New York Times, and the BBC, to name a few.
In today's episode, Jonathan discusses his journey as a leading voice in copyright and plagiarism consulting. He shares insights into the challenges of protecting intellectual property in the digital age, offering practical advice on addressing online plagiarism, copyright infringement, and related issues.
Jonathan reflects on a career-defining mistake where he made a fear-driven decision to take an exclusive job, which ultimately led him to realize the importance of betting on himself.
The conversation also spans topics such as effective ways to handle plagiarism, the role of proper attribution, and the differences between copyright and plagiarism, offering valuable lessons for content creators and businesses navigating intellectual property challenges.

Questions and Topics:
What is your favorite mistake?
What is your best definition of plagiarism in both academic and business contexts?
How do you handle gray areas in plagiarism, such as overly close paraphrasing or using someone’s ideas without credit?
What inspired you to start Plagiarism Today?
What advice would you give to content creators dealing with websites that copy their work without permission?
How does the DMCA process work for addressing online copyright infringement?
What mistakes do people make in assuming online content (like photos or videos) is free to use?
Can you explain the difference between “free” and “royalty-free” content?
How can podcasters or creators avoid legal pitfalls when using music or other media?
Are there connections between your haunted house work and intellectual property issues, such as using copyrighted characters?
Why is copying and pasting content on platforms like LinkedIn or Threads a problem, even when attribution is provided?
What steps can platforms like LinkedIn take to address copyright infringement?
How should creators respond to claims that unauthorized use of their work is "helping give it exposure"?

Randy Scott of ESPN: The Live TV Blunder That Became His Favorite Mistake

My guest for this bonus episode of the My Favorite Mistake podcast is ESPN anchor Randy Scott. He shares a hilarious yet humbling story from his early days on live television. Reflecting on an on-air blunder during Highlight Express, Randy reveals how the moment taught him resilience, the power of adaptability, and the importance of laughing at yourself.
Join us as Randy takes us behind the scenes at ESPN and shares valuable lessons learned from his favorite mistake!
See video, transcript, and more
 

From CIA to CEO: Rupal Patel on Leadership, Resilience, and Owning Your Weird

My guest for Episode #288 of the My Favorite Mistake podcast is Rupal Patel - she’s a former CIA analyst turned serial entrepreneur, who has embarked on an unconventional journey from military briefing rooms in jungles to corporate boardrooms and international stages. 
Episode page with video, transcript, and more
Her newly released book, From CIA to CEO: Unconventional Life Lessons for Thinking Bigger, Leading Better, and Being Bolder, is not just a memoir but a comprehensive ops manual and tradecraft toolkit for leaders and entrepreneurs. 
Serving primarily under President George W. Bush after 9/11, she became an intelligence expert on Afghanistan. She advised Four-Star Generals, earned War Zone Service Medals, and was recognized by the CIA Director for “superior support to the President of the United States.”
After leaving the CIA, she earned her MBA and started her first award-winning business over ten years ago. Rupal is a sought-after international speaker and corporate advisor who has spoken in front of thousands and delivered leadership and talent development programs for Fortune 500 companies around the globe and the White House.
In this episode, Rupal shares her journey from briefing four-star generals in war zones to advising Fortune 500 companies in boardrooms. She reflects on a defining moment at the CIA, where a false accusation taught her the importance of standing up for herself and overcoming self-blame. Rupal discusses lessons in leadership, the value of emotional intelligence, and the power of “tactical ignorance” in decision-making and problem-solving. She also explores how owning one’s uniqueness—what she calls “owning your weird”—can unlock potential and authenticity in leadership and life.
Questions and Topics:
What’s your favorite mistake, and what did you learn from it?
How did the accusation from your supervisor affect your working relationship?
Did that experience lead to your decision to leave the CIA?
What motivated you to join the CIA, and how did that opportunity come about?
How did your CIA experience shape your transition into business and leadership?
What CIA methods or mindsets do you think are most applicable to business strategy?
How do you balance strategic planning with the unpredictability of real-world situations?
Can you explain the concept of “tactical ignorance” and its role in decision-making?
What advice do you have for leaders or entrepreneurs facing setbacks or mistakes?
What inspired you to write From CIA to CEO, and what was the writing process like?
Did you need CIA approval to share details in your book?
What does “owning your weird” mean to you, and why is it important for leadership?

Learning from Havana: CEO Steven L. Blue’s Reflections on Mistakes & Success

My guest for Episode #287 of the My Favorite Mistake podcast is Steven L. Blue, the CEO of Miller Ingenuity, a global manufacturer and supplier of railroad parts and high-technology rail safety systems and services.
Episode page with video, transcript, and more
He’s a recognized expert in business transformation. With 50 years of experience leading companies across diverse industries like manufacturing and publishing, Steve has a proven track record of turning businesses around and driving massive profit increases.
A best-selling author and regular media personality, Steve is also a sought-after keynote speaker who has spoken at prestigious venues like Harvard Business School, The United Nations, and Carnegie Hall. His leadership insights have been featured in major outlets like The Wall Street Journal, Fox Business, Forbes, and CNBC.
In this episode, we dive into the pivotal lessons learned from mistakes, exploring how past successes can plant the seeds for future missteps. Steve shares his story of a bold but ultimately flawed business venture in Cuba, unpacking how ego and faulty assumptions led to failure—and valuable insights.
We discuss the importance of testing assumptions, inviting challenges from peers and boards, and fostering a culture that learns from, rather than fears, mistakes. Steve also highlights the transformation of Miller Ingenuity, offering wisdom on leadership, rebranding, and building a culture of continuous improvement that empowers employees to innovate and adapt.
This conversation is rich with reflections on the intersection of humility, risk-taking, and the resilience required to navigate today’s business landscape.

Questions and Topics:
What is your favorite mistake, and what did you learn from it?
What was the event at Carnegie Hall where you spoke?
How did you approach navigating the challenges of broadcasting from Cuba?
Why do you think there was low interest in the U.S. for the Cuba broadcast?
What lessons did you take away about making assumptions in business?
How do you accurately forecast interest in new ventures?
What role does ego play in decision-making, and how can it lead to mistakes?
Why is failure an important part of learning and eventual success?
How do you test assumptions before making significant investments?
What’s the role of a board of directors in challenging and validating assumptions?
How do you navigate resistance to new ideas within your team or board?
What was the process behind rebranding Miller Ingenuity?
How did you ensure the rebrand was successful and aligned with your business goals?
What role does culture play in Lean manufacturing at Miller Ingenuity?
How do you foster an environment where employees feel safe admitting mistakes?
What’s your approach to hiring and ensuring cultural fit within your teams?
How do you balance empowering teams with stepping in during a crisis?
What leadership attitudes are most likely to lead to business disasters?
What steps do you take to prevent and respond to unforeseen disasters?
What advice would you give to other leaders about sustaining a culture of continuous improvement?

Nancy Ho on Losing $300K in 5 Months: Lessons on Overcoming Failure, Life Purpose, and Work-Life Integration

My guest for Episode #286 of the My Favorite Mistake podcast is Nancy Ho, a distinguished Life Strategist, Clarity Messenger, and State of Mind Specialist with over 26 years of experience guiding individuals toward holistic success. 
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Episode page with video, transcript, and more
Throughout her illustrious career, Nancy has empowered over 10,000 clients, including C-Suite executives, mid-level managers, and business owners, to navigate the intricate balance between professional achievement and personal fulfillment.  
She’s co-author of the book Success Redefined with Jack Canfield.
In today's episode, Nancy shares the story of her favorite mistake—losing $300,000 in just five months pursuing a lifelong dream of opening a wine bar. She reflects on the critical lessons she learned about the importance of due diligence, trusting gut instincts, and recognizing misaligned partnerships. Nancy discusses how this experience shaped her approach to coaching, helping clients uncover their life purpose, navigate the paradox of professional success, and integrate work and personal fulfillment. She offers practical strategies for managing stress, addressing incomplete tasks, and shifting from fear-based thinking to resilience and clarity. Nancy’s insights provide inspiration and actionable advice for anyone striving to align their career, values, and sense of purpose.

Questions and Topics:
What is your favorite mistake?
What were some of the biggest challenges you faced during this venture, and how did you handle them?
What lessons did you learn from this experience, and how do you apply them in your work today?
Do you have any regrets about walking away from the business?
What is your life purpose, and how do you help others articulate theirs?
What do you mean by the “professional paradox,” and how do you help clients facing career and life challenges?
How do you approach unraveling the root causes of professional struggles for your clients?
What strategies do you recommend for managing stress caused by incomplete tasks?
How do you help clients shift from fear of failure to a mindset of resilience and growth?
How has this mistake influenced your approach to life and business coaching?