My Favorite Mistake: Business Lessons from Failures and Success

CTO Kevin Goldsmith on Leveraging Failure to Drive Success at Spotify and Distrokid

My guest for Episode #198 of the My Favorite Mistake podcast is Kevin Goldsmith, the chief technology officer at DistroKid, the world’s largest distributor of digital music.
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Kevin is an experienced leader of high-profile, high-performing product, research, and shared technology engineering organizations. An often-invited speaker on building strong engineering teams at conferences internationally – often talking about learning from failure. Has extensive experience building products using Lean, Kanban, Scrum, and Extreme Programming methodologies.
In this episode, Kevin tells his favorite mistake story about the launch of “Spotify Now” when he was an engineering leader at Spotify. Why was there pressure to launch? What mistake did Kevin and team make regarding data from a small group of initial users? How did Spotify leverage its culture of “handling failure well”? What did Kevin learn?
Questions and Topics:
How do you balance the cost of lost customers vs. the cost of embarrassment?
Being surprised by the results of experiments
Was Spotify Now a problem of a bad concept or bad execution? Or Bad design?
Losing customers as “the cost of learning”
Organizational learning to not get into this situation again?
Doing retrospectives on EVERYTHING to remove the stigma?
The Forbes article that Kevin was quoted in
People who strongly believe in “accountability” — punishing failures — can you change their minds?
Failure vs. mistake? — how would you compare those words?
Tell us a little bit more about DistroKid – strengthening this culture of learning from mistakes?
Video and Blog Post by Kevin:
Fail Fast, Fail Smart… Succeed! by Kevin Goldsmith
Blog post version of the story at Spotify
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This podcast is part of the Lean Communicators network.
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ADHD Expert & Entrepreneur Kristen Carder Regretted Spending $10k on a Mastermind Program

Host of the "I Have ADHD" podcast
Episode page with video, transcript, links and more
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My guest for Episode #197 of the My Favorite Mistake podcast is Kristen Carder. She is a serial entrepreneur and mindset coach for adults with ADHD. She's the host of a podcast: “I Have ADHD.”
In this episode, Kristen tells her favorite mistake story about spending $10,000 on a “mastermind” group that was not at all what she expected. Why was there a gap between her expectations and reality? When did she realize there was a problem? What did she do and how did she learn from this, as a coach-ee and a coach? We also talk about mistakes related to understanding ADHD and living with it — at work and in our personal lives.
As she always says on her podcast, she's “medicated, caffeinated, and ready to roll.”
Questions and Topics:
When did you realize it was a mistake? Did you ask for a refund? 3 reasons why not…
When should somebody join a “mastermind” instead of getting 1×1 coaching?
Lesson learned: explicitly lays out WHAT a mastermind is when she sells one
Red flags that you’re getting bad info about ADHD?
Why ADHD is not simply a “gift” or a “superpower”?
How do you define ADHD?
The inability to direct attention
Trouble regulating impulse – attention and emotion?
You were diagnosed in college… I was diagnosed last year at age 48… what led to you getting diagnosed?
Causes? Differences in the brain?
A mistake to tell people at work that you’re ADHD?
Explanation not an excuse
Her FOCUSED coaching program
Please follow, rate, and review via Apple Podcasts or Podchaser or your favorite app — that helps others find this content and you'll be sure to get future episodes as they are released weekly. You can also become a financial supporter of the show through Anchor.fm.
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This podcast is part of the Lean Communicators network.
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Support this podcast: https://podcasters.spotify.com/pod/show/favorite-mistake/support

From Shark Tank and Infomercials: Kevin Harrington’s Cash Flow Crunch - Just the Mistake

Kevin Harrington, from "Shark Tank" and creator of the infomercial.
Welcome to My Favorite Mistake. I’m Mark Graban. This is “just the mistake” — a new experiment.
Today we’ll hear the “favorite mistake” story shared, in episode #1, by Kevin Harrington — one of the “sharks” on season 1 of the show “Shark Tank.” He was the creator of the modern 30-minute infomercial and he shared a powerful story from 30 years ago.
To hear the entire episode with Kevin and his co-author Mark Timm, go to www.MarkGraban.com/mistake1
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Joe Perello, CEO of Props, on Building Strong Work Relationships and a Culture of Learning from Mistakes

CEO of Props -- ⁠Episode page with video, transcript, links and more⁠
My guest for Episode #196 of the ⁠My Favorite Mistake⁠ podcast is Joe Perello, president and CEO of Props, a first-of-its-kind, marketing technology platform enabling DTC brands. Joe is also a member of the board of directors of New York Cruise Lines.
Prior to Props, he co-founded and led an NYC-based digital agency and bootstrapped it into an award-winning shop.
In 2003, Mayor Michael Bloomberg appointed Joe as the first Chief Marketing Officer of the City of New York. Joe and his team created the first self-funded marketing and promotional engine in the City's history, generating more than $100 million and paving the way for unprecedented results in tourism.
Joe was the Vice President of Business Development for the New York Yankees during some of their most successful seasons, reporting to the late George M. Steinbrenner.
In this episode, Joe tells his favorite mistake story about a “work divorce” that was “really hard” — was it a mistake to separate himself from a company and certain workplace relationships? How did he learn to take responsibility for those relationships? We also discuss how to create a culture of learning from mistakes and creating an environment where you can be wrong.
Questions and Topics:
Work divorces are hard… it WAS the right thing to do
Felt like it WAS a mistake as it happened – turned out to be best…
Fear — no idea what I was going to do next…. — uncertainty or a mistake
It’s always a judgment call – a mistake or not??
The founder dynamic made it more difficult – personal pride
Lessons learned to prevent future work divorces??
Culture of learning from mistakes? “Create an environment where you can be wrong…”
Getting things wrong helps us get it right??
“I don’t want to be right I just want to win”
Direct marketing – test and learn, test and learn
Fail fast, fail often?
Props – how did the company pivot??
Mistakes that marketers make? Being inauthentic or failed attempt at authenticity that didn’t ring true?
Mistaken perceptions of the late George Steinbrenner… public perception vs reality?
Please ⁠follow⁠, rate, and review via ⁠Apple Podcasts⁠ or ⁠Podchaser⁠ or your favorite app — that helps others find this content and you'll be sure to get future episodes as they are released weekly. You can also ⁠become a financial supporter of the show through Anchor.fm⁠.
You can now ⁠sign up to get new episodes via email⁠, to make sure you don't miss an episode.
This podcast is part of the ⁠Lean Communicators network⁠.
 

Ward Vuillemot on the Power of Celebrating Errors and Understanding Customer Behavior for Business Success

Episode page with transcript, links, and more
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My guest for Episode #195 of the My Favorite Mistake podcast is Ward Vuillemot. Ward is a seasoned C-suite executive with over six years of experience leading fully remote teams while building technology organizations from the ground up for companies with 150 to 650 employees in size and $50M to $125M in revenue across the Americas and Europe.
He is currently Chief Product Officer and CTO at RealSelf. He is a technical advisor with his own company, where he advises startup founders and CEOs on technical roadmap and technology organization along with lean approaches to finding market signals quickly.
I invited Ward because of this Forbes article about celebrating errors.
In this episode, Ward tells his favorite mistake story about launching “Amazon Tote” and why there was “too little friction” in user experience. What did he learn about understanding the customer experience? In a separate story, what was Ward's epiphany about seeing an ant on a bus?
Questions and Topics:
Innovation is doing something others haven’t done before
Tell us about the Celebration of Error (CoE) concept – and practice…
Chicken and egg between psychological safety and CoE?
How much Psychological Safety is necessary and how does CoE build more PS?
From Correction of Error (Amazon) to Celebration of Error?
Are all errors created equally in terms of what to celebrate?
Discovering mistakes that had been there for years
As a person who is “high-functioning autistic” – is it ever a mistake to disclose something that personal?
From mindset to document?
IMPACT of the error on business – send to whole company?… why it matters, not why it happened
RESOLUTIONS — short-term and long-term (countermeasures) – fire out, then prevention
ROOT CAUSE – “show your work”
When to use a CoE?
People “NEED” to make mistakes to hit ever-greater goals?
Taking an impersonal, non-blaming approach — easier said than done? Fighting the instinct to blame?
Please follow, rate, and review via Apple Podcasts or Podchaser or your favorite app — that helps others find this content and you'll be sure to get future episodes as they are released weekly. You can also become a financial supporter of the show through Anchor.fm.
You can now sign up to get new episodes via email, to make sure you don't miss an episode.
This podcast is part of the Lean Communicators network.
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Support this podcast: https://podcasters.spotify.com/pod/show/favorite-mistake/support

Dr. Richard Winters Was Too Transparent in Showing Billing Data to Physicians

Author of the book YOU’RE THE LEADER. NOW WHAT? Leadership Lessons from Mayo Clinic.
Episode page with video, transcript, and more
My guest for Episode #194 of the My Favorite Mistake podcast is Richard Winters, M.D., an emergency physician at the Mayo Clinic. And he’s the author of YOU’RE THE LEADER. NOW WHAT? Leadership Lessons from Mayo Clinic.
As director of Leadership Development for the Mayo Clinic Care Network and as an executive coach, Dr. Winters provides coaching for Mayo Clinic leaders.
Dr. Winters graduated from the Mayo Clinic Alix School of Medicine in 1994 and returned to Mayo Clinic in 2015.
Previously, Winters served as managing partner of a democratic physician group, department chair of an emergency department, and president of an 800-physician medical staff.
In this episode, Dr. Winters tells his favorite mistake story about being a little too transparent with physicians in a meeting at Mayo Clinic. Why did so many physicians get upset about this discussion about data around billing practices? Why did it help for him to admit the mistake? How did he adjust and what did he learn from this mistake?
We also talk about questions and topics, including:
Was it a mistake to be so transparent?
Breaking down hierarchy and hearing the perspectives of others
Burnout in healthcare, not just doctors but nurses and others… bad before COVID, worse now?
Psychological well-being — 6 dimensions
What are key signs of burnout? How to recognize it and how to bring it up??
Is burnout different than depression?
A mistake to blame the person who is burned out? Resiliency training?
Fix the person or fix the environment?
Your book — the “now what?” Implies being thrown into a leadership role… is there enough formal leadership education, development, and mentoring in healthcare?
How are physicians taught about leading — and being parts of care teams — during medical school and residency? Formal education or seeing the behavior modeled by others?
Ronald Heifitz – technical vs adaptive challenges
Key differences in the leadership style at Mayo Clinic?
Responding to clinical mistakes… medical error, patient harm?
To you, what are the ideal leader behaviors?
There’s normally so much hierarchy in HC… what was the “democratic physician group” that you were a part of, what does that mean?
You can now sign up to get new episodes via email, to make sure you don't miss an episode.
This podcast is part of the Lean Communicators network.
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CEO and Investor Kurt Wilkin on Why Being a ”Proud Mistake Maker” is Key to Business Success

CEO of HireBetter and managing partner of Bee Cave Capital.
Episode page with video, transcript, and more
My guest for Episode #193 of the My Favorite Mistake podcast is Kurt Wilkin, a co-founder and CEO of HireBetter and managing partner of Bee Cave Capital. His bio says he's “coach, mentor, entrepreneur… and proud mistake-maker.”
Prior to founding HireBetter, Kurt founded and led The Controller Group (TCG), a professional services firm focused on accounting, technology and recruiting, which was acquired by Tatum in 2006.
He’s the author of a new book, Who's Your Mike?: A No-Bullshit Guide to the People You'll Meet on Your Entrepreneurial Journey. You can learn more at WhosYourMike.com.
His quiz that he mentioned in the episode: WHOSYOURMIKE.COM/QUIZ
In this episode, Kurt tells his favorite mistake story about not having a complementary “execution partner” to help him run a business. How (and why) did he adjust? Why did he step aside from the CEO role and what did he learn from this entire experience that serves him well today?
We also talk about questions and topics, including:
What does it mean to you to be a “proud mistake maker”??”
How do you try to create a culture where people can also be proud mistake makers? Leading by example?
Investing in people who are humble enough to learn…
Learning from mistakes vs. avoiding company-killing mistakes?
You’ve said that you saw your dad struggle as an entrepreneur. Were you able to learn from any of his mistakes?
You joined a failed startup in the dot-com bubble… any lessons learned from that?
Mistake to try to swing for the fences vs. lifestyle cashflow positive business
TELL US ABOUT THE BOOK: A business book for people who hate business books?
Find Kurt on social media:
LinkedIn
Twitter
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Michael Reddington on Learning from a Consulting Sales Mistake: Insights from a Forensic Interviewer

President of InQuasive, Inc.,
Episode page with video, transcript, and more
My guest for Episode #192 of the My Favorite Mistake podcast is Michael Reddington, an expert forensic interviewer and the President of InQuasive, Inc., which provides businesses and leaders with the tools they need to improve their leadership by activating the truth in all of their business interactions.
In his new book, The Disciplined Listening Method: How a Certified Forensic Interviewer Unlocks Hidden Value in Every Conversation (Per Capita Publishing, March 2022), Michael details his innovative listening approach for anyone looking to improve their communication and relationship-building skills. Using his background in forensics and his understanding of human behavior through interrogation, Michael teaches businesses to use the truth to their advantage.
In this episode, Michael tells his favorite mistake story about making assumptions about a client's readiness to work with him. Did “arrogance” lead to him not having a plan or a strategy? What did Michael learn and what did he start doing differently as a result?
We also talk about questions and topics, including:
Making assumptions — Ellen Patnaude episode 141
Started out working in loss prevention — Identifying shoplifters and dishonest employees?
How you introduce yourself… and how has that changed?
What is a Certified Forensic Interviewer (CFI)?
TV and movie investigations — realistic or cliched nonsense? – Hollywood and “24”?
How do you approach getting people to share information about their mistakes (or crimes?) when it might not be in their interest to be truthful?
Leadership coaching, sales & negotiation training…
Tell us about the book – who is this for?
Consultant asking prospect about problems they need to solve? How to get them to open up?
What is the “disciplined listening method” and what makes it “disciplined”?
Tell us about InQuasive and the work you do… who hires you and to do what?
Find Michael and his company on social media:
LinkedIn (personal)
Twitter
YouTube
LinkedIn (company)
This podcast is part of the Lean Communicators network.
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From Pain to Progress: How Psychologist Julia DiGangi Overcame her own Mistakes

Founder and CEO of NeuroHealth Partners, LLC.
Episode page with video, transcript, and more
My guest for Episode #191 of the My Favorite Mistake podcast is Julia DiGangi, the founder and CEO of NeuroHealth Partners, LLC.
Dr. DiGangi holds a Ph.D. in psychology and has worked in the field of neuroscience. She has published extensively in the scientific literature. She is known for her engaging, funny, and relatable communication style, which allows her to help others think about how the brain’s “wiring” affects workplace behaviors such as motivation, performance, and relationships.
She has also worked extensively in U.S. politics, including on presidential campaigns and at The White House Press Office, so she is accustomed to helping people gracefully navigate fast-paced, high-stakes professional environments. She has also given a TEDx talk on the relationship between our brains and stress.
In this episode, Julia tells her favorite mistake story about the very painful mistake of leaving academia. When did it feel like a mistake that “ruined everything” and how did she reach the point of “post-traumatic growth”? We also discuss her expertise in how the brain and the body react to mistakes and how we can go from “avoiding pain” to “choosing the most powerful pain.”
We also talk about questions and topics including:
Did you OVER in your academia work?
Was there a time when it DID feel like a mistake?
“Leaving the pain behind??” – “the brain is a pain detection machine” – the brain will generate pain
How did you end up in politics? This was before academia
What happens when you make a mistake — reaction in your nervous system?
Perfectionism — fear of mistakes
How do we move forward from those feelings?
Leadership & emotional intelligence are key themes
Are we OVERcomplicating E.I.?
Understanding others vs. understanding ourselves?
Upcoming book — tell us about that
“From Pain to Power….”
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From Self-Doubt to Success: How a Positivity Expert Don Sandel Launched his own Business

Founder of GoPositiv
Show notes, video, transcript, and more
My guest for Episode #190 of the My Favorite Mistake podcast is Don Sandel. He’s a former executive turned leadership coach and is the founder of GoPositiv.
He’s been leading talent development efforts for small and large organizations for the last few decades and has transitioned those skills and experiences into GoPositiv and now to books as well. He’s the author of the book Positive Mindshift: Making Good Things Happen in Life and Work.
He began studying the brain and its effect on learning about a decade ago, and discovered compelling and irrefutable research around positivity.
In this episode, Don tells his favorite mistake story about a time when he was working for a large global company and he listened to self-doubt triggered by a comment from his boss. Why did he give the worst presentation of his life? And what did he learn from this experience in a way that inspired him to start studying positivity??
We also talk about questions and topics including:
What sorts of positive self talk would you say before giving a speech??
How to aggressively battle the negative self talk and change that to positive self talk?
What prompted you to study positivity? How did you study this?
Not being a “Pollyanna”?
John Saunders, who introduced us — his episode
Does positivity lead to better medical outcomes if you have cancer or another serious ailment?
Weight loss and motivation — talking about positive motivations instead of negative / barriers?
Losing weight vs. getting healthier??
Is it too negative to think about mistakes? How can we be positive about mistakes?
The definition of optimism – thinking things will be better
“If dream it, you can do it” —- really?
Is “toxic positivity” really a concern? What does that phrase mean to you?
How would positivity have helped in your previous corporate jobs? Were better performing organizations more positive? Experience vs research?
Optimistic salespeople
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