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

Blake Mycoskie, founder of TOMS Shoes and a serial entrepreneur, shares his journey from building a globally recognized company with a one-for-one giving model

Key takeaways

• External success does not guarantee internal fulfillment; true worth comes from self-validation and inner alignment.
• Gratitude practice becomes transformative when it's specific—focusing on tangible moments like a child's photo at camp or a friend's text message.

Main topics

• Gratitude meditation and its role in mental resilience
• The emotional cost of external validation despite financial success

Notable quotes

I was grateful that my kids are this or grateful, you know, it was about family and friends. But I do think to go back to your question on, you know, a little bit more of the how is what happens when you do this.

Conclusion

Blake Mycoskie's story reveals that lasting fulfillment comes not from achievements or

Transcript preview

Speaker 2 (0:01) Welcome to the Learning Leader Show presented by Insight Global. I am your host, Ryan Hawke. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now, on to tonight's featured leader. Blake Mycoskie is the founder of Tom's Shoes. He 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. Blake eventually sold Toms to Bain Capital for hundreds of millions of dollars. That unfortunately led him to a deep depression. He went dark for almost four years. He hit every marker of success, and he still felt empty and worthless. During our conversation, Blake describes exactly what happened, why, and how he made it to the other side. We also discuss what he specifically looks for when hiring a leader, his morning mantra and how it helps him, what he learned about himself after going on the amazing race with his sister. why you should never wait for permission, and what you should do if you want to get a great spouse. Ladies and gentlemen, please enjoy my conversation with Blake Mycoskie. You have this beautiful background. It's not fake. It's real. What were you doing 90 seconds before we connected here? Speaker 1 (1:45) Yeah, I mean, literally, I'm still dripping with saltwater because the waves are so good in Costa Rica right now. And I'm not even at my house. I luckily brought my computer to my friend's little beach shack and left it here while I surfed. And then I got out, dried off, put a hat and T-shirt on, and here we are. I got this beautiful cat who I don't know right here hanging out with me and waves crashing. And you found me on a little vacation. My kids are at camp this month, so I'm getting some time for myself. And it's really nice. What is it about surfing that you love? You know, I love just being in the water. I usually surf at sunrise. So I get it's also an excuse to see the sunrise every morning. And I think there's something magical about and I've read some stuff about the ions and the waves and how it connects with our energy and charges us up. Also, the thing that a lot of people don't realize that they're not surfers is that most of what you do when you're surfing is just sit on your board. And so it's almost a meditation because you're actually only surfing. I just surfed for three hours and I probably caught maybe 10 waves total. I was probably on the board standing, you know, less than five minutes. So most of it is paddling, which is great exercise and sitting there, which for me gives me a chance to really do things like. my gratitude meditation or to sit there and really think through something that I might rush through in normal life. And so I always come out of the water with a really good mindset and actually something that for people who are like me and probably like you have lots of ideas, especially business ideas. My new hack is I got an Apple Watch and I programmed it to where if I hit the button on the side, it turns on the voice memo. And so I used to sit in the watering circle and have all these ideas and then I'd forget them because I don't have a pad and pen. So now I sit there and every time I have an idea or, oh shit, I need to call my mom back. I just go talk. And then when I get back, they're all there. So it's cool. I love Speaker 2 (3:41) it. You mentioned a gratitude meditation. Tactically, what is that? Are there specific words you say? Are they the same ones or is it, hey, I'm grateful for this? Like, Speaker 1 (3:50) what does that sound like? So it's kind of sounds like a prayer. So depending on what your religious or spiritual beliefs, it's a, you know, thank you, God. Thank you, universe, for, and I think the most important thing is being very specific. So like this morning, I was like, thank you, God. Thank you, universe, for the pictures that I saw last night of my daughter at camp looking like she was having the time of her life in the lake because the camp posts pictures for the parents to see. you know and it's great because this is their first time to ever go to camp and i was you know i want to make sure that she's happy there and she looks like she is i mean i i know my daughter she does not have that smile unless she's ecstatic she's kind of a stoic girl and so seeing those photos just made me feel so grateful and for her experience and then also it's great because now i can really relax down here myself and so that was one of the things that i rattled off and i just kind of say him to myself But I try to do it every day and oftentimes I'll write it down if I'm journaling. It's easy, especially today, I feel Speaker 2 (4:49) like for us to complain, for us to highlight and think about the things that are not going well, for the troubles, the challenges, the people that may have wronged us, whatever. It's very easy to go there. What does focusing on being grateful, and I love that you said with specificity, because that's a big word for me. I love specificity and praise. and thanking somebody and complimenting specificity is so critical love notes you know you talk about being with someone you love i think specificity with love notes is very very important so how does being grateful and actually voicing it thinking about it knowing you're going to do it every day how does it help you especially in a world where it's very easy to be a cynic and to be upset about things that maybe where you've been wronged Speaker 1 (5:36) Yeah, and I would say it's easy to go down that negative path. And I'll say just at the top of the show, you know, after I sold Tom's shoes, I got extremely depressed. And I experienced a depression for almost seven years. And for two of those years, it got so intense that I was suicidal. So like, it was really, really intense. And I say that at the beginning, because I think it'll help give a framework to our conversation, because I will honestly say for five years, I couldn't write five things I was grateful for. Yet I still had all the same things in my life. And so I want to really show compassion for someone who might be listening and be like, oh, it's easy for you, Blake. You're in the water surfing. You've got all the success. You're doing well now again. But it isn't easy. But I will say, even during those five years, when it was so hard to even think of one or two things a day, it was something I still tried to do. maybe I didn't even feel it, but I do think it was one of the things that kept me going and kept me on this planet because oftentimes it was things like, I'm grateful that my kids are this or grateful, you know, it was about family and friends. But I do think to go back to your question on, you know, a little bit more of the how is what happens when you do this. is you start recognizing that you actually have a lot more to be grateful than you think so. Because if you do it every day, you're not going to say the same thing every day, right? So I'm not going to be thankful for my daughter at camp tomorrow, even if I still am. So every day you have to kind of build your gratitude list. And so what that does is that forces you to expand your aperture of how you're looking at your life and what are you grateful for. So before you know it, you know what you're talking about? I'm grateful for espresso. I love the buzz of an espresso. I don't drink, I don't do drugs, but espresso is my thing. And so then you're like, ah, I love espresso. And so it really can grow if you can make it a practice. But if someone is listening or watching and saying, man, my life just sucks right now and I feel stuck and I'm not happy and I'm not grateful for anything, okay, I was there. I was there for a good five years. Speaker 2 (7:40) It's hard to imagine looking from the outside because you sell Toms. We all know Toms. bought lots of Toms probably. I know I have, my whole family has. And you get hundreds of millions of dollars in cash. I know you agreed to give at least half of it away. Half of it away, yeah. Yeah. And so you think like, what Speaker 1 (7:58) is Blake talking about? He got Speaker 2 (7:59) hundreds of millions of dollars, can literally do whatever he wants. And yet. you said it's like, what was happening? You see the wire come in or I don't even know. I assume that's how it happens. And you're like, oh my God, my bank account is infinite. Speaker 1 (8:13) And yet you feel bankrupt. It seems like on the inside. Yeah. I mean, basically what happened was, you know, and this is only, I'm only able to really speak to this now after, you know, years of therapy and unpacking it. But the simplest way to explain it is my whole life. I never felt that I was enough. And I basically needed external validation to just get through the day. Now, thankfully, in some ways, I was really good at getting external validation. I mean, I built a company that helped give 100 million children shoes, which put me on the covers of all these magazines, which people celebrated the one-for-one model. You know, I made a lot of money, as you said, but that was really not even what it was about. But that... that constant need for the external validation. Once I sold Tom's, yes, I had a lot of money, but almost like a drug, like that dried up the external validation. I was no longer running the company. I was no longer, you know, with all the people that were working there, I felt isolated. I didn't feel like I had purpose. You know, I actually had moved to Jackson Hole, Wyoming. I was living in the mountains, which was getting dark early every day. The point was, is once I didn't have the external validation, and to make me feel like I was enough. Then it got very dark because I was like, well, I did everything my parents told me to do. I did everything that the society told me to do. I built a great company. I made lots of money. I helped 100 million kids. I got married. I had kids. 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. And so that's why it got so dark so fast. in my situation because there's nothing left I could do. Like I did everything and I should, and the world was telling me I should feel great. I sure couldn't tell anyone about it. So I went dark on social media for almost four years. You know, I didn't do a single post after being prolific on social media. And it was because I just couldn't lie to people anymore. I couldn't act like my life was great and I was happy when I was so suffering. Because I was ashamed because like, who am I to say I'm suffering when people are struggling paycheck to paycheck? And so that I think is a very, and I'm sure a lot of people listening and watching this are entrepreneurs and business leaders. Some might relate to that. And that was why I was excited to come on the show because it can be extremely lonely if you achieve everything you set out to do and yet you don't feel whole inside. So there are probably people who experience this on various levels. They may not sell their Speaker 2 (10:47) company for a bunch of money, but maybe they're super accomplished. They're achievement oriented and they've achieved, they've done the things, they beat the goals in a huge way, whatever. What are some things that if that person thinks like, well, once I do that, I will feel this. And then they do it and they go, oh. I don't feel like I thought I would. In fact, maybe they feel worse or they feel bad. Like, what am I supposed to do? What would you say to that person? Maybe they're, they're about to have that happen to them. Maybe it just did happen to them. What advice would you give them? I Speaker 1 (11:20) would say the first thing is don't panic because that's what I did. I panicked. And so then I really made a mess of my life because I was like, okay, well. If I build the dream house, then I'll feel better. If I get divorced, I'll feel better. If I do, and I just, one kind of mistake after another, which you can do a lot of when you have a lot of money. So I say, don't panic and recognize that I believe that this is been designed in almost a divine way to not give you the satisfaction. Because if you have the achievement and you get there and you realize that it's not everything that everyone in society told you. I believe it was designed to feel empty so that that will be forcing you to go inward. And that's really, I think, where the big adventure in life starts and what I call the inner adventure. Because if you have been someone who has put so much emphasis on the external to feel good, then there's clearly something you need to work on on the internal. And that was the case for me. And that started my healing journey, which has been the greatest experience of my life and has led to my purpose. you know, doing my No Magic Pill podcast and everything in my life, they really come from hitting rock bottom because nothing external could make me feel better. To me, that feels like focusing on Speaker 2 (12:35) your personal purpose, your core values, your critical behaviors, like all of the ways that you live your life, having the internal scoreboard of what it means, your own personal definition of success slash happiness, contentment. Not societies, not what you see on Instagram, but your own version of that. And that takes work. That takes being super thoughtful, reflective, probably a lot of writing, talking with people who could be helpful. That's how I would, I feel like, and I've tried to do that. How is that for you? Like going inward? Because sometimes you hear the word like journey and all this, and people will start going, oh, this guy is like a woo-woo. hundred millionaire dude or whatever. And to me, I don't sense the money has anything Speaker 1 (13:17) to do with it all. It's purely about doing work. It's actually incredibly practical. So once I did some healing around this with some deep traditional therapy and really went back and saw where this came from my childhood and how I've been trying to. deal with it my whole life, I was able to do some real healing around re-patterning my neural pathways. And I think there's some real science behind the message that we tell ourselves for so many years. Mine was, you're not enough. Well, I had to change that to that I am enough. And so one of the very practical things that I did is I created this bracelet that I'm wearing right now, and it says enough on it. The idea was to have a daily reminder every day. to tell myself, which sounds so simple, I am enough, I've always been enough, I'm enough, I've always been enough. And if you do that for long enough, you start to repattern that subconscious thinking, which I think can have a real impact on someone's life. And the thing is, is that sometimes we just need a physical cue. to catch ourselves in a negative thought pattern loop. And so since I started feeling better and using the bracelet, we now sell the NF bracelets and we donate 100 % of the profits to