My Favorite Mistake: Business Lessons from Failures and Success

Fired by a Tech Bro: How Getting Sacked from Postmates Launched Author Tash Doherty's True Career

My guest for Episode #302 of the My Favorite Mistake podcast is Tash Doherty, a British-Irish-American author, blogger, and podcaster currently based in Mexico City. A graduate of the Wharton School at the University of Pennsylvania, Tash previously worked in analytics for Postmates and Vox Media.
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Today, she is the creator of Miss Educated—a popular blog and podcast covering business, pleasure, and women's health. Tash is also the author of the coming-of-age young adult novel These Perfectly Careless Things, self-published in 2023. She gained viral attention on TikTok by openly sharing her experiences with birth control.
Fresh out of Wharton at age 23, Tash joined Postmates in San Francisco, working in analytics. When offered a team change, Tash ignored her gut instinct and reluctantly joined a team run by a manager whose working style clashed sharply with her own. Within months, their professional relationship deteriorated, leading to Tash's unexpected firing just two weeks before the company conducted widespread layoffs.
Initially painful, this mistake forced Tash to reassess her career direction, ultimately opening the door to writing, entrepreneurship, and creative independence—turning a devastating setback into her favorite mistake.
In this episode, we also discuss Tash’s insightful critique of technology companies and their unintended contributions to economic inequality, her process of transforming a teenage passion project into a published novel, and practical advice on balancing creativity with financial sustainability.

Questions and Topics:
What’s your favorite mistake?
Were there early signs of trouble with your boss, Sumit, or did problems develop later?
How did you choose Postmates as your first job after graduating from Wharton?
Did your poor relationship with Sumit impact your job performance?
Was it hard to trust another company or manager after that experience?
Did you ever consider starting your own company again after leaving Postmates?
Do entrepreneurs have a responsibility to reduce economic inequality, or is that up to policymakers?
What specific mistakes do you see tech companies making right now?
What led you to write your article, "How Tech Is Ruining the World"?
Can you elaborate on how tech companies like Postmates worsen inequality?
What did you mean when you described tech workers as being "incurious about the machine"?
Is the tech industry truly improving society or causing greater harm?
How should entrepreneurs or policymakers handle technologies that cause harm when scaled?
Tell us about writing your book, These Perfectly Careless Things—how did it evolve over time?
How do you decide when your writing is finished and ready to publish?

Overcoming Setbacks: Jonathan Small on the Career Mistake That Sparked His Success

My guest for Episode #301 of the My Favorite Mistake podcast is Jonathan Small, an award-winning journalist, editor, podcast host, and producer based in Los Angeles.
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As president of Strike Fire Productions, he has built a diverse career that spans magazine editing at top publications—from Child Magazine to Maxim—and pioneering roles in digital media and podcasting. Known for his candid storytelling and willingness to embrace risk, Jon has transformed professional setbacks into defining career moments, including leaving a cushy executive role to reinvent himself in a rapidly changing media landscape.
He's also the podcast of a podcast called "Write About Now." Jon's also the author of a book with the same title.
In this episode, Jon recounts his bold decision to leave a high-flying magazine career in New York for a risky, low-paying production role in Los Angeles—a move that, despite its initial challenges (like parting with his beloved cat and facing financial uncertainty), ultimately redefined his career. He shares insights into the evolution of the publishing industry, the shift from print to digital media, and how even seemingly disastrous mistakes can pave the way for reinvention, new opportunities, and personal growth.
Jon also delves into his extensive experience as a writer and interviewer, offering practical advice on common pitfalls in writing and the art of “show, don’t tell.” He emphasizes the importance of embracing imperfect first drafts, the necessity of reading widely to hone one’s craft, and the value of authentic conversation in podcasting—whether as a host or a guest.
Throughout the episode, listeners are treated to vivid anecdotes from his career, tips for leveraging AI in writing, and reflections on how vulnerability and genuine curiosity fuel both compelling storytelling and effective interviews.

Questions and Topics:
What is your favorite mistake?
What prompted you to leave magazine editing for a role in film production?
Did you consider returning to New York after the move?
What was your role at the movie production company?
What are the most common mistakes rookie writers make?
Can you provide an example that illustrates the difference between showing and telling in writing?
What tips do you have for becoming a more effective interviewer?
Based on your experience, what advice would you offer to guests on a podcast?

Marketing Over Bourbon with Sheila Butler: Data-Driven Strategies & Bold Moves

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My guest for Episode #300 of the My Favorite Mistake podcast is Sheila Butler, a Chief Marketing Officer with over 25 years of experience shaping integrated marketing strategies, building global loyalty programs, and driving customer engagement across both B2C and B2B sectors. 
She's the founder of Butler Marketing Group. Her track record includes leadership roles at Disney, JPMorgan Chase, Choice Hotels, and Axiom Bank.
She has a Bachelor of Science in Music and Business/Arts Administration from Indiana University and an MBA from UNC’s Kenan-Flagler Business School.
Today, Sheila shares her unique journey from a childhood passion for music and a stint at Disney, where she learned valuable lessons about the trade-offs between passion and pay. Despite a career start marked by lower-than-expected salaries and tough financial realities, she found that the relationships and experiences she built were invaluable. Her candid storytelling reveals how her early experiences taught her the importance of seizing opportunities—even when they seem like mistakes in the short term—to build a network that ultimately became a cornerstone for her current success.
Now, as the founder of Butler Marketing Group and host of her new podcast, "Marketing Over Bourbon," Sheila focuses on leveraging data-driven strategies to guide marketing decisions. She emphasizes creating safe spaces for experimentation, the power of testing and learning, and the need to balance strategic objectives with creative expression. Interwoven with her passion for bourbon, Sheila’s insights on marketing resonate with listeners who appreciate both practical advice and a genuine, relatable approach to career growth.

Questions and Topics:
What's your favorite mistake?
What are you drinking?
Do you prefer a bourbon Manhattan or a rye Manhattan?
Have you worked with any small distillers or distilling companies?
What drove you to launch your company?
How do you handle it when data contradicts expectations?
What trends are you seeing with companies becoming more data-driven in marketing?
Is half of your ad spend wasted, or is that changing with improved data insights?

Transforming Brilliant Jerks into Leaders: Luis Velasquez’s Coaching Strategies and Resilience

My guest for Episode #299 of the My Favorite Mistake podcast is Luis Velasquez, an executive coach in Silicon Valley and a Stanford Graduate School of Business facilitator. He's also the founder of Velas Consulting.
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Once a university professor and research scientist, Luis helps mid-level managers to C-suite executives around the world learn, adapt, grow, and thrive by helping them how to reframe their challenges and take the most beneficial next step. 
His new book, available now, is Ordinary Resilience: Rethinking How Effective Leaders Adapt And Thrive.
Luis is a contributor to Harvard Business Review and Fast Company, and was featured in best-selling author Dorie Clark’s book, The Long Game. An avid endurance athlete, he runs marathons, ultra marathons, and ironman triathlons. 
In today's episode, Luis shares his journey from being a university professor and research scientist to becoming a trusted leadership coach in Silicon Valley and a facilitator for the Stanford Graduate School of Business. Luis discusses his new book, Ordinary Resilience: Rethinking How Effective Leaders Adapt and Thrive, and outlines his unique resilience formula—commitment plus persistence multiplied by optimism. He explains that resilience isn't about bouncing back but about unlocking the inherent ability to adapt and thrive by continuously reframing challenges and learning from experiences.
Luis also opens up about a significant mistake in his coaching career. He recounts a time when he delivered 360-degree feedback in a way that was too direct and decontextualized, which led a client to become defensive and ultimately resulted in his contract being terminated. This experience taught him the importance of providing feedback within the context of an individual’s aspirations and personal growth, rather than simply relaying raw perceptions.
The conversation further explores his approach to transforming challenging personalities—like the so-called “brilliant jerks”—into effective leaders, and how embracing and learning from mistakes is key to unlocking resilience and driving both personal and professional growth.

Questions and Topics:
How long is an ultramarathon compared to a standard 26.1-mile marathon?
Given your diverse career, what is your favorite mistake—and what did you learn from it?
Should we express our degree of certainty when stating facts?
How do you define resilience in leadership?
How do you identify and connect with high-value, challenging employees—is it via referrals or direct outreach?
How often do you coach not only the “brilliant jerk” but also intervene with their teams?
What role does fear play as a catalyst for growth—is it simply about reframing it?
Have you observed leaders effectively fostering optimism among their teams?
What does “embrace the suck” mean to you, and why is it a pivotal concept in your book?

General Hospital Actor and QVC Host Andy Paige Turned a Bold Misstep into a Beauty Revolution

My guest for Episode #298 of the My Favorite Mistake podcast is Andy Paige. She's a soap opera actress, podcast host, QVC guest host, and national beauty/image/lifestyle expert. As Pearl on ABC's General Hospital, she brings real-life QVC flair to captivating audiences with innovative advertising.
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She hosts “The Dating Lab with the Hillbilly Yenta,” where she explores modern dating challenges with humor and diverse guests. Her international bestseller, Style on a Shoestring, earned her the title “Budget Bombshell” and inspired frugal style makeovers on TV worldwide.
With standout appearances on NBC’s Celebrity Apprentice, Starting Over, and TLC’s Ten Years Younger, Andy is the go-to expert for red-carpet style and practical image advice. She also delights radio audiences nationwide with playful style tips and has launched successful product lines including her patented GirlyGoGarter® and related accessories.
In this episode, Andy shares the dramatic story of how a miscalculated cliff jump not only resulted in a severe injury but also sparked a journey of innovation that led her to create the revolutionary Girly Go Garter. She reflects on the lessons learned from this life-altering mistake and discusses how it transformed her approach to both her career and personal growth.
She offers insights into the creative process behind her products, the challenges and triumphs of working in fast-paced television environments, and how embracing mistakes can lead to unexpected opportunities. Tune in for an inspiring conversation on resilience, reinvention, and the art of turning errors into stepping stones for success.

Questions and Topics:
What’s your favorite mistake?
Did you hit the edge of the rock when you jumped?
Was your foot catastrophically injured during the fall?
Did you expect a long rehab period and time away from the camera?
How many design iterations did the Girly Go Garter require—and is it still evolving based on feedback?
Did you try pitching your product on Shark Tank?
Did the Girly Go Garter play a role in landing your QVC gigs?
Is QVC always broadcast live?
How far in advance are soap opera episodes completed?
How did your role on General Hospital come about?
As a mother, how do you help your kids learn from mistakes?
Do you allow your natural accent to shine through on set?

Aviation Safety Explained: MIT’s Arnold Barnett on Why Flying Remains Incredibly Safe

In this special bonus episode of "My Favorite Mistake," host Mark Graban welcomes back Arnold Barnett, a renowned expert in aviation safety, to discuss public perception of air travel safety in light of recent air incidents. They explore common misconceptions about aviation risks, temporal fluctuations in safety data, and the factors contributing to the continuing improvement in aviation safety. Professor Barnett reassures listeners with data-driven insights and addresses the psychological biases influencing our perception of risk.
Episode page with video, transcript, and more
 
Key Discussion Points:
 
Public Perceptions vs. Reality: Arnie Barnett sheds light on why recent air travel incidents have caused public apprehension but insists that aviation remains incredibly safe.
 
Understanding Spasms of Events: Discussion on how statistical anomalies can lead to clusters of negative events but don't necessarily indicate a trend.
 
The Role of Probability: Barnett explains probability through coin toss analogies, emphasizing that rare clusters of events are expected even when the underlying system is safe.
 
Historic Comparisons and Data Trends: Insights into how aviation safety has followed a trajectory similar to Moore's Law, with risks decreasing significantly over decades.
 
Risks in Aviation: Highlighting the contrasts between accidental risks and potential threats from deliberate actions, such as terrorism.
 
Psychological Aspects of Risk: Exploration of how psychological biases, like availability bias, affect public perception of aviation risk.
 
Guest Bio:
 
Arnie Barnett
 
Arnie Barnett is the George Eastman Professor of Management Science at MIT Sloan School of Management and a pre-eminent expert in aviation safety. He has been recognized with the 2002 President Citation from the Flight Safety Foundation for outstanding contributions to safety and has received multiple teaching honors from MIT Sloan students. Barnett holds a BA in mathematics from Columbia University and a PhD in mathematics from MIT.
 
Previous Appearance: Arnie Barnett's favorite mistake story in Episode 169: https://www.youtube.com/watch?v=-ffe6bNtxlg
 
MIT Article: Explore the article on the MIT website detailing aviation safety trends and Moore's Law analogy, as discussed in the episode: https://news.mit.edu/2024/study-flying-keeps-getting-safer-0807
 
Memorable Quotes:
 
"If you see a little kid at an American airport, then that kid...is five times as likely to grow up to be president as to perish in the forthcoming flight." — Arnie Barnett
 
"Fears are deep, and when I respect them, I know many people who are afraid to fly, but I believe this is something we shouldn't be afraid of." — Arnie Barnett
 
Actionable Takeaways from the Podcast Episode
 
Stay Informed, Not Anxious:
 
Guidance: Understand that aviation safety is statistically very high, even amidst rare bursts of incidents. Arnie Barnett explained that the risk levels are closer to zero than perceived, as discussed with the "availability bias" and the statistical explanation regarding recent safety events.
 
Implementation: Arm yourself with reliable safety data and trends when feeling anxious about flying. Remind yourself that the perception of risk is often inflated by isolated incidents, which are outweighed by the overwhelming safety record of aviation.
 
Leverage Sound Arguments:
 
Guidance: Use metaphorical insights, such as Barnett's coin analogy, to effectively communicate the nature of rare events. This helps in understanding that a sudden occurrence of incidents does not necessarily indicate a systematic issue.
 
Implementation: When discussing risks, employ similar analogies to articulate to others that rare sequences of events do happen without indicating a broader change in safety. This approach can not only assure others but also help you internalize and remain calm about flying.
 
Focus on Broader Safety Trends:
 
Guidance: Be aware that deliberate attacks are an area of potential concern, but reassurances on trends are clear from Barnett, who discussed continuous improvements and the extraordinary safety levels in countries like the US, UK, and Canada.
 
Implementation: When planning air travel, focus on the historical safety record of airlines and recognize that current safety measures are stringent and continuously improving. For example, choosing airlines with exemplary safety records can further mitigate rare and unanticipated risks, providing peace of mind during air travel.

Learning from Mistakes: Norman Wolfe’s Guide to Building High-Performing Teams

My guest for Episode #297 of the My Favorite Mistake podcast is Norman Wolfe, the Founder and CEO of Quantum Leaders.
EPISODE PAGE with video, transcript, and more
Norman's journey as both a successful executive and a trusted coach to countless leaders has been driven by one central question: How can we improve our ability to achieve the results we want? His pursuit of this answer led him to master a wide range of business disciplines—from leadership and strategy to operations and finance—while also deeply exploring human potential, personal growth, and even spirituality.
Norman's mission now is to help others transform their thinking and approach to more effectively achieve their deepest desires.
In this episode, I chat with Norman about how mistakes can spark profound growth and innovation in leadership. Norman shares his favorite mistake story—from his early days as a first-time manager, where a harsh performance review challenged him, to the lessons that fueled his journey toward becoming a top leader at Hewlett-Packard. He explains Wolfe's Law, his formula that highlights the exponential impact of relationships and context on achieving outcomes.
We also dive into the principles of quantum leadership, discussing how a holistic, people-centered approach—blending practical leadership with a touch of spirituality and systems thinking—can transform organizations into dynamic learning ecosystems.

Questions and Topics:
What is your favorite mistake?
Did the negative review or your mentors provide specific, actionable feedback for improvement?
Is the formula you mentioned what you call “Wolfe’s Law”?
Could you state Wolfe’s Law for us?
Does your formula imply that relationships are exponentially more important than activity and context?
How does spirituality fit into your framework—does it fall under context or serve another role?
How do you assess whether individuals (or teams) are mature enough for increased responsibility?
What should be eliminated versus managed when dealing with ambiguity and risk?
From your experience, why is it essential to reframe mistakes as positive learning opportunities?
Do you believe that making mistakes fosters adaptation and growth?

How a Brutally Honest Communication Mistake Sparked Growth: Sherianna Boyle

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My guest for Episode #296 of the My Favorite Mistake podcast is Sherianna Boyle, a renowned psychic healer, speaker, and founder of Emotional Detox Coaching® and The Cleanse Method®. She has written over ten books, including the best-selling Energy in Action: The Power of Emotions & Intuition to Cultivate Peace & Freedom.
Her latest book is Just Ask Spirit: Free Your Emotions to Energize Intuition and Discover Purpose.
With over 25 years of experience in mental health and wellness, Sherianna integrates psychology, energy healing, and spirituality in her work. Her "Just Ask Spirit" podcast is in the top 5% globally, and she has been featured in major media outlets like Psychology Today, Yoga Journal, and Prevention.
In today's episode, we explored the idea that mistakes, particularly those born of brutal honesty, are vital opportunities for growth. Sherianna shared that her favorite mistake was being so candid—delivering feedback that wasn’t always received well—that she later recognized as a catalyst for learning and deeper self-awareness. She explained how that raw honesty, while sometimes painful in the moment, ultimately taught her the importance of embracing and processing emotions rather than suppressing them. By owning her truth and inviting forgiveness—from herself and others—she discovered that these so-called mistakes could pave the way for more authentic, supportive relationships and a greater alignment with her inner guidance.

Questions and Topics:
What is your favorite mistake, and why does it stand out?
Can you share a specific story that illustrates this pattern of brutal honesty?
Reflecting on those experiences, would you do anything differently in similar situations?
Can someone be prepared—or "braced"—for the impact of brutal honesty?
What advice do you have for those struggling with the aftermath of a mistake?
How can someone uncover the root of their emotional triggers, and what resources would you recommend?
In your work, how do you define "spirit" and its role in emotional healing?
Who is the ideal audience for your book, and in what situations would it be most helpful?

The Mistake That Cost Hundreds of Thousands: Josh Chernikoff on Business Growth and Sales

My guest for Episode #295 of the My Favorite Mistake podcast is Josh Chernikoff, a seasoned expert in the education sector with nearly 20 years of experience in EdTech, sales, and entrepreneurship.
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Josh is the founder of the EdSales Elevation Experience, a 12-week program designed to help education companies build lead-generation engines that consistently book 12-20 high-quality sales calls per month.
He has worked with hundreds of thousands of students and educational leaders, helping businesses scale with innovative, repeatable sales processes. Josh is also a Milken-Penn GSE Competition Judge, StartEd Mentor, and host of the podcast "Breaking the Grade."
In this episode, Josh Chernikoff shares the hard lessons he learned from choosing the wrong business partners and how that misalignment impacted his second company. He reflects on how personality fit and communication styles can make or break a business relationship, emphasizing the importance of testing collaborations on smaller projects before fully committing. Josh also opens up about a pricing strategy misstep that led to significant financial losses and the unexpected impact of the pandemic on his after-school enrichment business.
Beyond mistakes, we dive into what makes a repeatable, scalable sales process—why businesses struggle with lead generation, how to refine messaging, and the importance of credibility in attracting the right clients. Josh explains his Raise Your Hand campaign as a way to identify high-quality leads and tailor sales efforts to what potential customers actually need. We also discuss the power of having one clear offer, the role of objections in refining sales strategies, and why he stays laser-focused on education sales despite his methodology’s broader applicability. Toward the end, Josh shares stories from his early career as a TV sports broadcaster, including lessons learned at Northwestern’s Medill School and the intensity of live television.

Questions and Topics:
What’s your favorite mistake?
Did you realize it was a mistake right away, or did that realization develop over time?
What lessons did you take from that experience?
How can someone evaluate whether a business partnership is the right fit before committing?
Can you share more about the pricing change that didn’t go as planned?
How do you differentiate between handling objections in sales and truly learning from objections?
Why limit your business to education sales when your methodology could apply more broadly?
What are the most common sales mistakes you see, either in education or in general?
How important is it to focus on finding the right leads versus just generating more leads?
How do you identify high-quality leads and refine your targeting strategy over time?
What role does messaging play in sales success, and how do you help clients improve it?
How did your career start in TV sports broadcasting, and what led you to leave?
What lessons from broadcasting have helped you in your current work?
Was there a broadcast journalism equivalent to the Medill F?
How should professionals use LinkedIn to position themselves effectively?
What advice do you have for people struggling with lead generation?
How do you know when it’s time to pivot your business strategy based on market feedback?

How Authenticity and Resilience Shape Leadership Success: Mandolen Mull’s Insights

My guest for Episode #294 of the My Favorite Mistake podcast is Mandolen Mull.
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She has worked with global clients in various industries, helping organizations with change implementation and leader development training. The daughter of a master stone mason entrepreneur, Mandolen has a great appreciation for the responsibility of leaders in building trades and manufacturing realms. 
Mandolen has written a leadership handbook and is currently publishing her multi-series memoir titled Mullings, Mullivation, and MullMentum.
She was born in Fort Worth, TX, and inspired by her family's history in politics, she obtained a bachelor's degree in Political Science & Psychology and an MBA in International Business at McLane College of Business from the University of Mary Hardin-Baylor. 
Amassing over a decade of corporate leadership experience, she obtained her Ph.D. from the Soules College of Business at the University of Texas at Tyler in Organizational Development & Change. 
In this episode, we explore powerful leadership lessons drawn from personal experiences, including the importance of authenticity and earning credibility in challenging environments. Mandolen shares a defining moment early in her career when she stepped into a male-dominated workplace and made an impulsive decision that led to a valuable lesson about humility and resilience. She reflects on how listening, observing, and building trust with her team helped her become an effective leader, emphasizing that leadership is not about asserting authority but about connecting with people and addressing their needs.
We also delve into the impact of adversity on her leadership journey, including her experience with dystonia and how it shaped her perspective on resilience and empathy. Mandolen discusses the inspiration behind her memoir series, including themes of grit, transformation, and navigating complex relationships. Through candid stories about her personal and professional life, she offers insights into building trust, overcoming challenges, and fostering a leadership style that prioritizes connection, transparency, and growth.

Questions and Topics:
Can you share an update on your memoir series? What themes are you exploring in these books?
What’s the story behind your favorite mistake, and what leadership lessons did you take from it?
Was your initial approach to listening and observing natural for you, or did someone advise you to take that approach?
How did your father’s lessons and perspective shape your leadership style?
What advice did your father give you to help overcome challenges in leadership?
How did your team’s feedback inspire your transition to becoming a professor?
What is it like coaching ironworkers to become effective leaders and instructors?
How has your experience with dystonia and other health challenges influenced your leadership journey?
What inspired the title and concept of your first book, Grit for the Pearl?
What are the key themes of your upcoming books, and how do they connect to your life and work?