
702: Blake Mycoskie (Founder of TOMS) - Hitting Every Goal & Still Feeling Worthless... Gratitude, Mantras, and Hiring Like a Champion
The Learning Leader Show With Ryan Hawk
Hosted by Ryan Hawk
- 55m
- Transcript
Summary
Written by a model from the transcript; not yet reviewed.
Blake Mycoskie, founder of TOMS Shoes, discusses his journey from building a company that donated over 100 million pairs of shoes to suffering from a deep, multi-year depression after selling the business to Bain Capital for hundreds of millions of dollars. The guest and host explore the dangers of relying on external validation, the role of daily gratitude and mantras in healing, and the importance of shifting focus from work-life balance to harmony. Mycoskie also shares insights on his current projects, including the No Magic Pill podcast, the Enough Foundation, Morning Water, and advising an AI therapy app called Sonya.
Listeners will find value in Mycoskie's candid breakdown of post-achievement depression and the practical steps he took to rebuild his mental health without spending money. The conversation provides actionable hiring strategies, such as trying to talk candidates out of roles to test their commitment, and emphasizes the principle that people attract what they are rather than what they want.
- Make your gratitude specific by naming exact moments, such as seeing a photo of your daughter looking happy at camp. 3:55
- Combat negative thought loops by adopting a daily physical cue and mantra like "I am enough." 14:00
- Test startup candidates by being brutally honest about the negative aspects of the role to gauge their commitment. 42:41
- Focus on life harmony rather than rigid balance to ensure all areas of your life receive attention over time. 50:58
Chapters
- 0:56Post‑Sale Depression and Inner Struggle
Blake discusses the depression he faced after selling TOMS and the feeling of worthlessness.
- 2:15Gratitude Meditation as a Daily Practice
Blake shares how he uses gratitude meditation to shift his mindset and improve mental health.
- 13:47Healing Through Self‑Worth and the “Enough” Bracelet
Blake reveals his journey to self‑acceptance and the creation of the “Enough” bracelet to reinforce it.
- 25:29Parenting Philosophy and Teaching Kids to Be Enough
Blake explains how he applies his healing to parenting, encouraging children to feel worthy.
- 30:00Early Entrepreneurial Ventures: EZ Laundry and Billboards
Blake recounts his first businesses, from a laundry service to a billboard company, and their lessons.
- 33:38The Amazing Race Experience and Its Lessons
Blake talks about his participation in The Amazing Race, the challenges faced, and the insights gained.
- 39:19Balancing Purpose and Business as Chief Shoe Giver
Blake discusses how he balanced his passion for giving with the operational demands of running TOMS.
- 41:42Hiring Principles and Building a Complementary Team
Blake shares his hiring criteria, interview tactics, and the importance of surrounding himself with complementary skills.
- 43:00Hiring Philosophy: Attitude and Integrity
Blake discusses the importance of hiring for attitude, integrity, and commitment, especially in startup environments.
- 44:11Podcast Intro and Host Greeting
Ryan Hawk opens the episode, welcoming listeners and setting the stage for the conversation with Blake Mycoskie.
- 45:07Attraction Principle: You Are What You Attract
Blake explains how personal authenticity and honesty shape the people and customers you attract.
- 46:53No Permission Needed: Entrepreneurial Breakthroughs
Blake shares his belief that success comes from acting without waiting for permission and breaking conventional rules.
Highlights
- 1:45
Surfing and Voice Memo Hacksstrategy
The guest explains how surfing acts as a meditation and how he uses his Apple Watch voice memo to capture business ideas while sitting on his surfboard.
- 5:39
Depression After Immense Successstory
The guest details how selling TOMS and losing external validation led to a multi-year depression and suicidal ideation despite having achieved every societal marker of success.
- 11:37
Emptiness as a Catalyst for Growthinsight
The guest explains that achieving external goals and feeling empty is a designed force to push individuals toward inner personal development.
- 13:44
Rewiring Neural Pathways with Mantrasstrategy
The guest describes using the mantra "I am enough" for 20 minutes twice a day over 40 days to break negative thought patterns and heal his self-worth.
- 21:19
Advising an AI Therapy Startupstory
The guest discusses his involvement with Sonya, an AI therapy app, and how it provides a safe, judgment-free space for individuals to process deep shame.
- 44:45
Hiring for Attitude and Missionstrategy
The guest outlines his hiring philosophy, emphasizing that integrity and commitment to a mission matter more than resume building.
- 47:38
Breaking Rules Without Permissioninsight
The guest shares how starting businesses without prior industry experience allowed him to break conventional rules and succeed.
Quotes
“I created this bracelet that I'm wearing right now. And it says enough on it.”
Unnamed speaker · 13:47 “I think there's some real science behind the message that we tell ourselves for so many years.”
Unnamed speaker · 13:39 “I think integrity is number one, because in this day and age, if you're not highest integrity, it will get figured out really fast.”
Unnamed speaker · 44:45 “You attract what you are.”
Ryan Hawk · 45:28 “Be known for doing what you said you'd do.”
Ryan Hawk · 48:34 “I had no experience. I had never made a shoe before. I didn't know the shoe industry.”
Unnamed speaker · 47:38
Sponsored segments
- Insight Global 0:01–0:10
- Blake Mycoskie 53:01–53:15
About this episode
The Learning Leader Show with Ryan Hawk www. LearningLeader.com https://www. LearningLeader.com The Price of Becoming is a USA Today, LA Times, and Publishers Weekly Best-Seller! www. LearningLeader.com/Becoming https://www. LearningLeader.com/Becoming This is brought to you by Insight Global https://insightglobal.com/learningleader/. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. Blake Mycoskie founded TOMS Shoes in 2006 after a trip to Argentina, where he saw children without shoes and built a company around giving away a pair for every pair sold. TOMS went on to donate more than 100 million pairs of shoes and became one of the most copied business models in the world. What most people don't know is what happened after he sold it, and I'm grateful that he was open to talking about that on this episode of The Learning Leader Show. Key Learnings Make your gratitude specific. Not "I'm grateful for my family." Name the exact thing. Blake's example from that morning: the photos the camp posted of his daughter laughing in the lake, and knowing his stoic kid does not smile like that unless she is genuinely happy. He kept the practice going for five years when he couldn't feel any of it. Blake could not name five things he was grateful for, and he had all the same things in his life he has now. He did it anyway. He credits it as one of the things that kept him going. Surfing is a great thinking practice. Surfing is mostly just sitting on the board. Three hours in the water, ten waves, maybe five minutes standing. The rest is paddling and sitting. That's why it works as a thinking practice. Capture the idea in the moment or lose it. Blake programmed the side button on his Apple Watch to open a voice memo. Every idea he has sitting on the board, he records. They're all waiting when he gets out. He hit every marker and still felt worthless. "I did everything, and I still, deep down in my soul, had this feeling like I'm not worthy, I'm not enough, and I never will be." The external validation was the drug. Selling TOMS cut off the supply. The thing that had been holding up his sense of self was suddenly gone. If you get there and it's empty, don't panic. Panicking is what Blake did, and having money meant he could make expensive mistakes fast. Build the dream house. Get divorced. One thing after another. The emptiness may be the point. Blake's read on it: if achievement delivered what society promises, you'd never go inward. Feeling hollow at the summit is what forces the inner work. He re-patterned the sentence he'd been telling himself since childhood. The old one was "you're not enough." He replaced it with "I am enough. I've always been enough." Twenty minutes every morning and every evening. Forty straight days. It worked, and he no longer needs to do it daily. Sometimes you just need a physical cue to catch the loop. That's the whole idea behind the bracelet he wears. Not magic. A reminder on your wrist that interrupts the thought. Give the second one away. Blake found the bracelet's real power was handing one to a friend. Now you're both wearing it, you're both in on it, and there's an unspoken agreement that neither of you has to have a bad day alone. Men are worse at building that than women are. Tell your kids they're enough, and keep telling them. They're going to get the opposite message from everywhere else, which is exactly why it has to come from you repeatedly. Blake says the relaxation you'll see in them is immediate. Be brutally honest about how hard the job is. Try to talk them out of it. Blake is the last interview in the process now. If he can lay out every negative and they still desperately want it, the commitment is real. "How many people did you convince not to take the role before you got the right person?" Most leaders slip into sales mode, talk the candidate into it, and end up talking themselves into the candidate. What he screens for during the interview process: Integrity first. If it isn't there, it surfaces fast now. Attitude second. The person who never says "that's not my job." Whether they're building a resume or joining a movement. Find the people who cover what you're bad at. Blake is a storyteller, a vision-sharer, and high energy. He is not a supply chain guy, not a finance guy, and he has trouble saying no. So he hired around it. That's what let him actually be the chief shoe giver instead of pretending to be a CEO. Don't wait for permission. Most people stand in line at the front door. Blake looks for side doors. In Argentina he had no investors and no plan, just an idea and the words One For One. Ryan's version for his kids: everyone can apply online. Drive to the restaurant and go talk to the manager instead. Having no experience was the advantage. He'd never made a shoe, so he didn't know which rules he was breaking. Same with outdoor advertising. Same with driver's ed. He learned it from Richard Branson: ask forgiveness, not permission. Nashville wouldn't allow advertising, so he sold art instead. Blake spent two years with the city council and got there by removing the ad from the ad. No price, no call to action. Just album covers on the sides of buildings, called country music art. Once one artist had one, they all wanted one. He sold the company to Clear Channel. You don't attract what you want. You attract what you are. Want honest friends, be honest. Want peace at home, bring peace. Want trust, practice it when nobody's watching. Blake applies it to customers too: sloppy companies attract sloppy customers, and that's usually the real reason the business fails. Charlie Munger got asked how to get a great wife. He said: deserve one. Be known for doing what you said you'd do. Early on Blake didn't have the skills, so he built the reputation on execution instead. Move fast, keep it simple, do it with integrity. Momentum is a form of trust. The other half of that is not overpromising. Blake's own failure mode is getting excited, feeling falsely confident, promising something big, and missing. When it happens, own it fast and be honest, and the relationship usually survives. Be careful using a general-purpose chatbot as a therapist. Blake's warning, and the reason the founders of Sonia built a purpose-built tool instead: the big consumer models are designed to make you feel good about yourself. If you need to hear something hard, that's the last thing you want. He went from skeptic to advisor in six months. Blake met the Sonia founders at a mental health conference, tried the app to be polite, and by the third session was getting insights he hadn't gotten elsewhere. He now spends five to ten hours a week helping them. His reason for loving the work: "Now I get to be the coach instead of the athlete." Stop chasing balance. Design for harmony. Blake picked this up from an executive at Cannes who said she'd given up on balance. He goes hard in phases. Full dad mode with the office waiting on emails. Then all in on a launch and missing things at home. The measure isn't evenly split day to day. It's whether, over a year, everyone in his life feels like they got what they needed to thrive. Including him. Reflection Questions What did you actually feel grateful for today? Not the category. The specific moment. What is the sentence you've been repeating to yourself since childhood, and is it true? In your last hire, how hard did you try to talk them out of it? Or did you spend the interview selling them, and then sell yourself? More Learning #598: Sam Parr https://learningleader.com/samparr598/ - Bold. Fast. Fun. Living by a Mantra & Building a Media Company #547: Dr. Michael Gervais https://learningleader.com/mikegervais547/ - Stop Worrying About What Other People Think of You #676: Jesse Cole https://learningleader.com/bananas/ - Built for The Fans (The Owner of the Savannah Bananas) Episode Chapters 00:00 Meet Blake Mycoskie 01:38 Surfing is Great for Deep Thinking 03:41 Make Your Gratitude Specific 05:39 Blake Sold TOMS and Fell Apart 11:20 Advice for Those to "Make It" and Feel Nothing 13:23 "I Am Enough" and the Bracelet on His Wrist 17:35 The No Magic Pill 19:41 The Risk of Chatbot Therapy 22:42 A Surgeon Dad, a Bestselling Mom, and the Pressure Nobody Said Out Loud 25:13 Telling Your Kids They're Enough 31:31 How He Got Country Music Art on the Side of Buildings 35:15 Learning to Be Proud of TOMS Again 38:49 Hiring Around Your Weaknesses 41:25 Try to Talk Them Out of the Job 45:07 You Don't Attract What You Want. You Attract What You Are. 46:54 Don't Wait for Permission 48:34 Be Known for Doing What You Said You'd Do 50:02 The Champagne Question: Harmony, Not Balance 52:28 EOPC
Transcript
11,376 words · 2 speakers
Speaker names marked are inferred from speaking time and the show’s known hosts — they are not voice-verified.
Topics
- TOMS
- Morning Water
- No Magic Pill
- Sonya
- EZ Laundry
- Nashville
- The Amazing Race
- Journeys
- San Francisco
- Costa Rica
Page updated · transcript and summary are machine-generated