My Favorite Mistake: Business Lessons from Failures and Success

Dr. mOe Anderson Took a New Job Without Knowing Who the Employer Was

Dentist, author, podcaster, speaker, and more
Episode page with video, transcript, links, and more
My guest for Episode #185 of the My Favorite Mistake podcast is Dr. Monica Anderson, a.ka. Dr. mOe. She is a dentist… she is and does many things… including bestselling author, podcast host, dynamic “mOe-tivational” speaker, cancer survivor, and leader of the non-profit, Drop The Drugs, Inc.
She has been featured in numerous media outlets, including Parade Magazine, Fox News, and ABC’s Good Morning Texas. And now, here!
Dr.mOe couples her business and personal experiences, to share game-changing, powerful life lessons with both humor and passion. And, by the way, I didn't make a mistake in the capitalization of her nickname!
Dr. mOe has published several books, including her 2021 novel, Never Close Your Heart, and her most recent
Dr. mOe has published several books, including her 2021 novel, Never Close Your Heart, and her most recent book Launch Your Self-Publishing Journey: The Busy Author’s Guide to Write, Publish, and Sell Your Book Fast!
Her podcast is “Perpetual mOetion With Dr mOe Anderson.”
In this episode, Dr. mOe tells her favorite mistake story about signing a contract to take a job, without knowing the name of the organization! Why did it seem like a huge mistake to take that job (under those conditions) and how did it turn out to be a great learning opportunity for her through those challenges? What did she learn about the mistakes we can make when changing jobs?
We also talk about questions and topics including:
Not a mistake to leave private practice?
Mistake to accept a job not knowing WHO the client was, signed a contract…
The non-profit she leads, Drop The Drugs, Inc.
As a dentist – what are you taught (school or workplace) about dealing with possible mistakes as a dentist?
Preventing vs. correcting mistakes in dental work?
You've written multiple novels and then non-fiction books including that book about self-publishing — what got you started as a writer?
Tell us about your podcast – “Perpetual mOetion With Dr mOe Anderson”
Find Dr. mOe on social media:
Facebook
Twitter
Instagram
LinkedIn
YouTube
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CEO Bryan Clayton Thought Outsourcing Technology Development Would Be Better Than Building It

CEO of GreenPal
Episode page with video, transcript, and more
My guest for Episode #184 of the My Favorite Mistake podcast is Bryan Clayton. He is the Co-Founder and CEO of GreenPal, an online marketplace that connects homeowners with local lawn care professionals. GreenPal has been called the “Uber for lawn care” by Entrepreneur magazine and has over 300,000 active users completing thousands of transactions per day.
Before starting GreenPal, 10 years ago, Bryan Clayton founded Peachtree Inc., one of the largest landscaping companies in the state of Tennessee, growing it to over 150 people and $10 million a year in annual revenue before it was acquired in 2013. Bryan‘s interest and expertise are related to entrepreneurism, small business growth, marketing, and bootstrapping businesses from zero revenue to profitability and exit.
In this episode, Bryan tells his favorite mistake story about outsourcing the development of an app, thinking all he had to do was the marketing. What went wrong and how did he discover the mistake? What did he learn and what did he learn about mistakes, leadership, and culture in an organization more broadly?
We also talk about questions and topics including:
Where did you get the idea to outsource?
When did you first start discovering that it was a mistake?
Using “Lean Startup” principles?
What was your Minimum Viable Product?
What’s your mindset on mistakes that happen in the company now?
From a culture standpoint, what did you learn from the first company that you applied to the second?
“You get the company culture that you deserve as a leader”
“I made every mistake you could make” – felt victimized
“Took me a long time to self reflect about the mistakes I made.”
Do you ask for feedback from employees about the culture?
Mistakes people make when hiring a lawn care company?
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Psychologist Kristin Neff Was a ”Mama Bear” in Defending Her Ph.D. Student and Had to Apologize

Professor, author, and researcher on "self-compassion"
My guest for Episode #183 of the My Favorite Mistake podcast is psychologist Dr. Kristin Neff.
Episode page with video, transcript, and more
She is the author of the books Self-Compassion: The Proven Power of Being Kind to Yourself, and the 2021 follow up book — Fierce Self-Compassion: How Women Can Harness Kindness to Speak Up, Claim Their Power and Thrive.
Kristin received her doctorate from the University of California at Berkeley and is currently an Associate Professor of Educational Psychology at the University of Texas at Austin. While doing her post-doctoral work she decided to conduct research on self-compassion – a central construct in Buddhist psychology and one that had not yet been examined empirically.
I learned about Kristin's work thanks to a mention of her by Dan Pink, my guest in Episode 137.
In this episode, Kristin tells her favorite mistake story about passionately defending one of her dissertation students who wasn't passed by a new assistant professor. Why was Kristin being a “mama bear” and why was she called on the carpet by her department chair? What did she learn from this experience and how did she apply “self-compassion” to herself in this instance?
We also talk about questions and topics including:
Before talking about self-compassion, people might have mistaken definitions of compassion… how do you describe the true meaning of compassion toward others?
HBR – self-compassion articles
“Self-compassion vs. self-esteem”
Finding the balance in acknowledging, reflecting, and learning vs. dwelling…
“Having compassion also means that you offer understanding and kindness to others when they fail or make mistakes, rather than judging them harshly.” — can you share an example that illustrates that?
How can we practice self compassion when we realize we have made a mistake in our work?
Important to soothe ourselves before reflecting on our mistake? How we might do that?
Does it help us be self-compassionate when others are compassionate toward us when we make mistakes?
What Self-Compassion is not — mistaken views?
Self-Compassion free survey
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Search Firm CEO Gene Rice: Youthful Ego and an Impulsive Decision Could Have Ruined Him

Chairman and co-founder of Rice Cohen International
Episode page with video, transcript, and more
My guest for Episode #182 of the My Favorite Mistake podcast is Gene Rice, the Chairman and Co-Founder of Rice Cohen International. He's the co-author, with his daughter, of the book Grad to Grown-Up: 68 Tips to Excel in Your Personal and Professional Life. You can learn more at the book's website.
Gene has been in the recruiting industry for nearly 30 years and has been recognized as one of the top Executive Search professionals in the world. He has completed over 1,000 retained searches which have included 211 in the C-suite. Having also filled over 300 Partner, Principal, and Director level searches in the Management Consulting, Performance Improvement, and EdTech verticals, Gene is considered to be the #1 search executive in the space. He has even been recognized by Recruiter.com as one of the “100 Most Influential People in the History of the Executive Recruiting Industry.”
Gene also co-founded Rice Cohen Training & Consulting, the largest training firm focused on improving the skills of executive recruiters. Gene is very passionate about this space and believes in supporting the industry he loves. He has become an Executive Coach to the CEOs of many search firms.
As an active member of the community, Gene finds various ways to give back and contribute. After years of being involved with the Make-a-Wish Foundation and serving on the board, Gene and his wife Michele founded the Plant A Seed, Inspire A Dream Foundation. The 501 c-3 non-profit helps financially challenged youth to pursue their passions. Since being founded in 2008, the foundation has awarded over 700 scholarships and has been featured in People Magazine.
In this episode, Gene tells his favorite mistake story about quitting a job to start a competing live music venue on Long Island and how his “huge ego” led him to be “impulsive” in the decision to do so. Why does he say it “could have destroyed” him, why is it better to make mistakes like this when you're young, and how did he apply the lessons learned in his successful career?
We also talk about questions and topics including:
Coaching young professionals who make mistakes?
Mistakes in working with an executive retained recruiter as a candidate?
Selecting C-level executives? — what helps make for a good match (3 things you really need)
The importance of C-level executives also having personal success and professional fulfillment (not just a job) — get your arms around that as a young professional
Coaching college interns — helping them the first time they fail… looking at failing differently
Charity that he started in 2008 with his wife: “Plant A Seed Inspire A Dream Foundation”
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Thought She Needed to Have All the Answers as Manager: Pamela Kellert

Strategic Leadership Expert
Episode page with video, transcript, and more
My guest for Episode #181 of the My Favorite Mistake podcast is Pamela Kellert. She helps female professionals in STEM sectors transition to senior management roles by learning strategic non-technical skills.
Pamela is a seasoned Strategic Leadership Expert with over 16 year’s experience working in Strategy, Business Development and Project Delivery, heading diverse teams at leading organisations across Australia, Asia, Europe and North America.
She has managed complex engineering projects and profit & loss responsibility of over $100 million with a team of over 100 employees. Throughout her career, Pamela has coached professionals in their leadership journey and created a systemised online coaching program to help women accelerate their careers to senior leadership roles. Learn more via her website.
In this episode, Pamela tells her favorite mistake story about how she thought she needed to have all of the answers when she was promoted into her first management position. If she was promoted for being good at problem solving, shouldn't she be solving all of the problems as manager? How did Pamela realize this was a mistake and how does she help other women learn from her mistakes?
We also talk about questions and topics including:
As manager, how should one integrate the ideas and solutions of others?
When to delegate and when to intervene?
Being promoted to senior leadership roles – what are the different challenges there?
Moving into a new function? Challenges there?
Do some executives never learn the lesson you did?
Challenges / mistakes with STEM women who want to step up into leadership positions and then into senior management… ‘
Is it important to have a female mentor? Also a male mentor?
Getting along by changing behavior vs. trying to change the broader system? How others should react vs. how they do?
Apologizing before saying something… diminishing language? — societal expectations?
Making yourself smaller physically? Women vs. men…
Different advice for women working in very male dominated environments?
Finnish prime minister backlash — compare to Aussie prime minister or Boris Johnson
Being aware of biases
Systemic sexism vs. System racism
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Tech Expert Dave Sobel ”Really Screwed Up” His First Company Acquisition

Host of the Business of Tech podcast, and owner of MSP Radio
Episode page with video, transcript and more
My guest for Episode #180 of the My Favorite Mistake podcast is Dave Sobel. He’s the host of the Business of Tech podcast, and owner of MSP Radio. Dave is regarded as a leading expert in the delivery of technology services, with broad experience in both technology and business. He owned and operated an IT Solution Provider and MSP for over a decade, both acquiring other organizations and eventually being acquired.
“The Business of Tech” is a leading IT services focused news and analysis podcast and YouTube show, with thousands of listeners and subscribers. He also co-hosts of the podcast “Killing IT”, and authored the book Virtualization: Defined.
Dave holds a bachelor's degree in Computer Science from the College of William and Mary. He lives just outside Washington DC with his wife and two cats. His interests include travel and food, cheering the Washington Nationals and Capitals, and smoking barbeque… He was introduced to me by Jason Levin, my guest in Episode 161.
In this episode, Dave tells his favorite mistake story about “screwing up an acquisition really bad.” Why did he not really understand the full situation of the company? Was it too late to make adjustments to the business after buying it? How did he apply the painful lessons learned when he sold his company in 2011
We also talk about questions and topics including:
Why did he start a company?
What he learned about being laid off from startups as a tech person
Spent more time on the “paper” and not enough on the “people”
Was it too late to make adjustments?
Did you acquire other companies?
Sold his business in 2011
Applied the lessons learned… was a complete open book instead of withholding information like his seller had
Mistakes that small businesses make in choosing technology?
Examples of companies choosing software or tech because it’s trendy?
How often is the mistake about HOW they implement it?
The *delivery* of the tech is super important
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West Point Graduate Becky Margiotta Thought She Would Get an A for Effort Instead of Managing Outcomes

Cofounder and owner of The Billions Institute, LLC
Episode page with video, transcript, and more
My guest for Episode #179 of the My Favorite Mistake podcast is Becky Margiotta. She is the author of the book, Impact with Integrity: Repairing the World Without Breaking Yourself, a cofounder and owner of The Billions Institute, LLC, and the host of the Unleashing Social Change Podcast.
In this episode, Becky tells her favorite mistake story about thinking she would get an “A” for effort when working toward a bold goal of getting 100,000 homeless people into homes. Why did she “lose track of the outcomes” and how did she adjust and get back on track?
We also talk about questions and topics including:
What was the approach for reducing homelessness?
Looking at measures more continuously along the way
100,00 lives campaign connection through IHI
“Here’s what you’re doing wrong…” actually better ways to say it?
Story about how people don’t want the answer…
Leadership lessons from the Army and Special Operations that are transferrable?
Outcomes focus? Commander’s intent? (McChrystal book)
“Mission first, troops always”
“First woman to command special operations…”
Tell us about the Unleashing Social Change podcast
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CEO Ian Small Was Told He ”Needs to Learn to Listen Better”

CEO of Evernote
Episode page with video, transcript, and more 
My guest for Episode #178 of the My Favorite Mistake podcast is Ian Small, CEO at Evernote, the app that launched a personal productivity movement for knowledge workers around the world. Under Ian’s leadership (since 2018), Evernote found the courage to go back to basics, launching a new era of innovation for the company and building upon a decade of growth.
Ian brings more than 25 years of global product, technology, and business leadership experience to his current role. Trained as an engineer, Ian's career has evolved from designing and building user experiences at Apple into product leadership and large-scale business management as CEO of TokBox and global Chief Data Officer for Telefónica SA.
In addition to his current role at Evernote, Ian sits on the board of directors for Lumentum and is an advisory board member for Alphabet subsidiary Loon (a graduate of Google’s X Lab).
He holds a Master’s degree in Computer Science, a BASc in Engineering Science from the University of Toronto, and has earned more than 10 patents.
In this episode, Ian tells his favorite mistake story about being told, early in his career, that he needed to be a better listener. What were the consequences as he became a manager? How did he realize that he needed to change and how did he work to overcome that bad habit to the point that he can now coach younger leaders to avoid or get out of this same trap? And how did Ian learn to listen better to customers and employees alike?
We also talk about questions and topics including:
Your favorite patent?
Having to change habits… how?
“Listen with a beginner’s mind “ Marc Benioff – Salesforce
The episode with Emily Learing
Overhauling Evernote over 2 years — rebuilt from scratch?
Better listening to customers, employees, and the board/investors
Everybody internally (and customers) could tell you what the problem — why wasn’t it being addressed?
Was Evernote not listening or not taking action?
The mistake of inaction vs. action?
What do you think of the SV mantra “fail fast, fail often”?
How to avoid needing another reboot in 2030?
Mistakes in how users use Evernote or is that not possible?
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Therapist Emily Learing’s Child Care Program Mistake Could Have Been Worse, Opened New Possibilities

Mental Health Professional, Children's Book Author, and more
My guest for Episode #177 of the My Favorite Mistake podcast is Emily Learing, LMFT, RPT-S. She is a mental health professional based in South Dakota, at her practice called Encompass Mental Health.
Episode page with links, video, transcript, and more
Emily has an MA in Marriage and Family Therapy and a BS in Human Development and Family Studies. She’s a licensed Marriage and Family Therapist and a Registered Play Therapist. She has a blog called Disciplined Children.
Emily is the author of a fantastic children’s book: Henry Knows Best!: A Story About Learning From Mistakes and Listening to Others. I read it and found important lessons and reminders for me as an adult.
In this episode, Emily tells her favorite mistake story about setting up a child care center that was intended to attend to mental health needs — but the phone rang off the hook with people wanting and needing typical day care services. Why did she close the door to that program and how did that open the door to other possibilities? How did Emily manage to keep this in the realm of a small mistake that wasn't catastrophically expensive?
We also talk about questions and topics including:
Tell us what inspired you to write the book? Again, the title is Henry Knows Best!: A Story About Learning From Mistakes and Listening to Others
Oppositional Defiance Disorder vs just liking to say no?
How many kids are like Henry?
The consequences of always knowing best – damaged relationships?
Overconfidence vs. narcissism
“If you think you need help, you probably need help…”
Some of my previous guests have admitted that they didn’t listen to experts when they should have — that they knew best… Congressman Will Hurd and Jim McCann founder of 1-800-FLOWERS.
You say “I’m not a perfect person… I make mistakes… I don’t expect perfection… that’s not reality” — how does admitting that help clients, how does it help you work with clients?
Does it help others open up to you?
Having to live the values you’re stating about not being perfect…
Being a play therapist
On your blog, you write about games that can be used to help kids with ADHD develop their attention spans. Tell us about that…
Tell us more about the podcast… “The Informed Parent” (coming soon)
A BONUS favorite mistake from Emily
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Canadian Journalist & Author Mike Ulmer Learned From a Conflict With a Colleague

Publisher, book coach, and more.
Episode page with video, transcript, and more.
*** I WANT TO WRITE MY BOOK *** (AD)
My guest for Episode #176 of the My Favorite Mistake podcast is Mike Ulmer. While he specializes in helping business people write their books, he has written 13 books with a total of nearly $1 million in total sales revenue.
His latest book (March 2022) is Show and Tell Writing: A Great Short Business Book About How To Write A Great Short Business Book.
His other recent titles are Drop The Mic Marketing with Jason Hunt (2022), The 50-Year-Old Millennial: The Leadership Gap Exposed By Millennials And How To Close it with Marc Petitpas (2021) and The 40 Ways of The Fox (2021) with Ron Foxcroft.
He worked as the in-house storyteller for the Toronto Maple Leafs, Raptors and TFC as the senior writer at Maple Leaf Sports and Entertainment.
He has written for The Toronto Star, National Post, Southam News Bureau as well as news organizations across Canada.
Interesting fact — With 170,000 in sales, his book, M is for Maple is the bestselling alphabet book in Canadian publishing history. His website is https://www.mikeulmer.ca/
In this episode, Mike tells his favorite mistake story about striking a journalist colleague while in flight on a plane. Why did his sense of “grandiosity and recklessness” lead to this moment that changed his life? Why was this a “favorite mistake”? How did this moment make Mike realize that he needed help so he could now lead a better life?
We also talk about questions and topics including:
As a cancer survivor, why is it a mistake to use the phrase “battle with cancer?”
Why should people write a business book? You say in your book “everyone should” — why is that?
Even if you’re not a writer?
Credibility… Mistake to assume you can also speak?
Mistake to write with the audience in mind?
“Have to take a contrarian stance”
Publishing mistakes?
Predatory people in the publishing system?
“When I see the term best seller… bullshit”
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