Transcript of 702: Blake Mycoskie (Founder of TOMS) - Hitting Every Goal & Still Feeling Worthless... Gratitude, Mantras, and Hiring Like a Champion

Welcome to the Learning Leaders Show presented by Insight Global. I am your host, Ryan Hawk. 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 TOMS 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 4 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 Jake Mykowski. You have this beautiful background. It's not fake, it's real. What were you doing 90 seconds before we connected here?

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, 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, 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 if 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 was, I just surfed for 3 hours and I probably caught maybe 10 waves total. I was probably on the board standing, you know, less than 5 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 outta 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 water and surf and have all these ideas and then I'd forget 'em 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, doo doo doo doo, talk. And then when I get back, they're all there. So it's cool. I love it.

You mentioned 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, what does that sound like?

So it 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, and I want to make sure that she's happy there and she looks like she is. I mean, 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 them 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 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?

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 7 years. And for 2 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 framework to our conversation because I will honestly say for 5 years I couldn't write 5 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 this success. You're doing well now again. But it isn't easy. But I will say, even during those 5 years when it was so hard, to even think of 1 or 2 things a day. It was something I still tried to do, and 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, is about family and friends.

But, 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 then, I mean, and so it's, 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 5 years.

It's hard to imagine looking from the outside because you sell TOMS. We all know TOMS. We've all 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 is Blake talking about? You got hundreds of millions of dollars, could 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. Yeah. 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 TOMS, 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 it 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 was 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 4 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 company for a bunch of money, but 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, 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 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 has 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 learning, which has been, you know, the greatest experience of my life and has led to my purpose and, you know, doing my No Magic Pill podcast and everything in my life.

It's really come from hitting rock bottom because nothing external could make me feel better.

To me, that feels like focusing on 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/happiness, contentment. Not society's, 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 start going, oh, this guy is like a woo woo, $100 million dude or whatever. And to me, I don't sense the money has anything 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 repatterning 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, is have a daily reminder every day to tell myself, which sounds, you know, 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 re-pattern 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 mental health organizations.

And what I've found, the biggest power actually of the bracelet has been in sharing one with someone else. Because then you create kind of a bond where you're both wearing it, you're both committed to this journey of self-worth. And it's a reminder to both of you that you have someone you can depend on, which especially I think for men, it can be very lonely when you don't feel that you have someone that you can really share everything with. Women typically have that more than men. And so I give the bracelet to a guy friend of mine and we both wear it and we're reminded like, hey, if you're having a tough day, don't suffer alone. Give me a call and let's talk it through. And I think that that's super important. So there's nothing woo-woo about it. It's just like really simple. And, you know, we could do a whole hour or two about the neuroscience behind repatterning our subconscious with a mantra-based kind of meditation, which mine was, I am enough. I've always been enough. And I did that for 20 minutes every single day in the morning and in the evening for 40 days.

So it was really intense, but it worked. It really worked. I started to feel different in my body. And then I started to make good decisions and I, my whole life turned around.

Is there another mantra you do now in the beginning and end of each day, or is there another practice?

I actually don't even really meditate anymore. It's amazing. I mean, I found that there's other things like the gratitude practice and there's just sitting quietly in the morning. I have a practice where I, I really hydrate early in the morning, first thing, and I get some sunlight in my eyes before I go out and spend my day. But if it does sneak back up and I do have some, some feelings of insecurity or some doubts or feeling feeling stressed, then I do go back to the mantra, but it's not something I, I feel like I have to do every day. I feel like I, I need to do it to kind of re-interrupt that negative pattern that had been driving my life. And then the good thing too is for me, it's like once you feel aligned with your purpose, then everything also kind of falls in line. And so now running this nonprofit and giving out these bracelets to people, especially young people, because I think a lot of people, especially because of social media, they're really susceptible to not feeling enough or not feeling worthy because of what they see everyone else is doing.

By working on that every day and then working on my podcast and having people talk about their mental health has really helped me stay in a good mental state.

Somebody asked me recently about like, what's the motivation behind continuing to do this after so many years? And, and I said, it's like that farmer in Iowa who sends you an email saying, your podcast is the Monday night family dinner table conversation with my wife and my kids. And it's led to such rich dialogue. And so I say the juice of it, the purpose is one person at a time, one family at a time. In your case, maybe it's two people at a time, the person who has the bracelet and then gives it to somebody else. Because I think when it comes to your purpose, it has to include, in my opinion, helping other people in some way, shape, or form. There's different versions of that.

Totally.

You've lived that through Tom's, through what you're doing now and everything in between. How did you come about your purpose and how does that actually come alive in the world?

What I recognized after getting through my, you know, mental health crisis and starting to feel better a couple years ago was that I had such a unique opportunity to be radically honest about everything I went through, everything I tried. So my podcast is called No Magic Pill. And the reason it's called No Magic Pill is 'cause I had all the resources in the world to do everything I could possibly do to try to feel better when I was really depressed and struggling with panic attacks and anxiety. And so I was able to have the best therapist. I got brain stimulation at Harvard to try to wake up neurons in my brain so that I would get outta the depression. I did psychedelic journeys, I did pharmaceuticals, I did retreats in India. I mean, I have done it all. And, and so what I realized was, is Most people won't be able to do a fraction of those things. And what I also realized, which are so important, is most of the things that helped me ended up not costing any money at all. And so I decided to do this podcast called No Magic Pill, where I have people on who will maybe open up about their mental health journeys in a way they haven't before.

So we've had Matthew McConaughey on, we've had Kevin Love, we've had Jewel, we've, you know, had Michael Pollan. And that has become a huge part of my purpose because, and it's the way I'm executing it in a sense, is by inviting people to have conversations that would help someone who might be feeling stuck, who might be feeling depressed, who might be feeling lonely in their mental health journey. And I always say that at the beginning of the episode, I say the only reason we're doing the show is to think about, and please think about the person that just is about to give up, that's just stuck, that's just, and maybe they're just going through midlife and they're just like, I don't think the future is going to be any better than the past. Like, my best days are behind me because that's where I was. And so that's how every day as I work on that along with the Nuff Foundation, I am kind of living out my purpose. And then that actually led to another thing that I feel like, especially as we get a little older, that can really kind of enliven business people.

And that is really mentoring other entrepreneurs that are aligned with your purpose. And so I had the coolest experience 6 months ago. I was speaking at a mental health conference and the guys that spoke before me were these amazing MIT grads, like 26 years old, and they spent the last couple years building an AI therapy app as a research project. And they started it because, you know, they started to hear that people were using ChatGPT or Claude for therapy, and that's very dangerous because those LLMs are built to just make you feel good about yourself. And so if you have serious mental health things you need to talk about, the last thing you want to do is talk to someone who's just going to tell you, oh, that's great. Yeah, you're the right person. No, your ex-wife or wife should never have said that. Like, and we've seen some very bad outcomes. And so these guys were like, you know, we need to build something that is safe and also that will give access to the millions of people that can't afford therapy. Or people who just don't want to go to therapy. I go back to guys a lot.

Like a lot of my guy friends just don't want to sit in front of a therapist, even on Zoom, or have the time for it. And so I met them at this conference and they heard my story and they said, hey, we assume that you probably had some great therapists based on your story. We would love it if you would try it. And so I was really skeptical at first and I was like, okay, I'll give it a try. And I did a session and then I did another session. It's called Sonja is the name of the app. And so I'm talking to Sonya and about the third session, I was like, wow, like that was really insightful. Like, you know, and the other thing that was interesting about it was I was able to be radically honest cuz I was not worried about any judgment from this AI, right? So it's unlike a, you know, even a regular person. So I shared some things that I had some real deep shame around from my first marriage that like I probably hadn't even shared with my real therapist. And all of a sudden it was giving me some insights of like why this happened and this and that.

That was 6 months ago. And so I started using it, using it, and I finally was like, I gotta help these guys. And so I'm now spending 5 or 10 hours a week helping them. It's on the App Store now. I mean, they're just getting ready to start charging, but it's incredible. I mean, it's helped me so much. And the cool thing is, is, is there's no judgment and it has infinite memory. So it'll bring up things from like 4 months ago that we talked about that helped me then to help me now. And so that has really enlivened me as an entrepreneur because now I get to be the coach instead of the athlete, you know? So like they're the athletes, they're the founders, it's their company, and I'm getting to really give my perspective and guidance on the things that I've learned in hopes that they will be able to help millions of people with this. And so I work on Sonya all the time and I love it. And it's been really a good way for me to think about How do I extend my purpose beyond the things that I'm just doing myself?

You mentioned before about your parents. I read that your mom wrote books, diet books. Is that right?

Yeah, yeah. Cookbooks.

Cookbooks. Cookbooks. And your dad was a surgeon?

Yes. Great.

So what was it like growing up with a surgeon and an author of cookbooks? I assume it sounds like high standards, accomplished people themselves. What was your upbringing like with them?

Yeah, I think I, my dad was a really great surgeon and very smart guy. I mean, obviously still is, not a surgeon anymore. So I think there was a, a level of pressure and achievement that was built into this life. My mom wrote her books when I was kind of out of school. I was like 16, so that was, had less influence on me maybe as a young person, but where my mom's influence really came in for me and my sister, because my sister's an incredible entrepreneur. I don't know if you know her story. But we saw my mom go from a woman that never graduated college. She saw that she had a high cholesterol and she wanted to work on that. And while she did that, she wrote these recipes that lowered her cholesterol and she also lost some weight. And then she just wanted to help people. And so she self-published this book and it became the best-selling cookbook for like 5 years. She made millions of dollars, way outmade my dad. I mean, like my dad was basically retired early and it helped support her career. And my sister and my brother and I are like, wow, like, that's cool.

Like, she went from like no experience to making millions of dollars because she wrote a book to help people. I think that's probably the biggest influence of all was seeing her do that and then believing that you can kind of start something from nothing.

So I think about this as a parent, and I'm sure you do too. You said that you felt maybe pressure to achieve because your dad's this amazing surgeon? Was it talked about, like, Blake, we expect a lot from you, you're not working hard enough, your grades aren't good enough, or you got to get into this school? I know you played sports too, right? Or was it just you just felt it because you saw what they did?

I think it was felt. I don't— I never remember my dad putting too much pressure on me overtly. I think it was more I just had a deep desire. And maybe, I mean, depending on what you believe in terms of how you come into this world. I mean, maybe karmically I came in here to really heal this wound of not feeling enough. And so it might not have had anything to do with my parents and just that I just innately felt that I had to achieve and accomplish to earn love because I never— that was never told to me early.

Okay. So now that you're a parent, how does that impact you as a dad trying to raise, you know, great kids to go up and, and feel enough? But also still leave a positive dent in the world like you're doing. How does that impact your parenting philosophy?

Well, I think one of the most important things I've done is once I healed this wound in myself that I didn't feel enough, I feel like my whole relationship to my kids changed because I think I was putting that pressure on them, whether I realized it or not. And that's why I always tell, especially high performers, I'm like, wear the bracelet and give one to your kids. And my kids wear it. It's like the best conversation you're ever going to have with your kids. I guarantee it. You will not believe the relaxation you will see in them when you tell them, yes, achieve your dreams, work hard, but regardless, you're enough and I love you just for you. And that is the conversation that I hope every parent has with their kids and they have it over and over again. Because what's going to happen is even if I tell that to my 11-year-old and my 8-year-old, They're still going to get the message that you're only good if you're smarter or prettier, or you have this many likes on Facebook or Instagram or Snapchat or whatever they're doing. They're going to still get that message from everyone else.

So it's even more important that the parent is telling them that they are enough just as they are. And so that is at the core of my parenting philosophy. And I've seen a huge difference in my relationship with my kids since I healed it in myself. The second thing I think that is so important if we're talking about parenting, is I just keep going back to like the most important thing is just to be kind. Just to be kind. You never know what someone's going through. You never know what their situation is. Just being known as the kindest person. And so I really work with my kids on what are opportunities to just be kind, kind to strangers, kind to each other. They're not always kind to each other. That's the hardest part, an 8 and 11-year-old. But I will say they're very thoughtful about other people. In other people's situations, and especially when you have resources. Like one of the coolest things happened the other day. I was with my son, we were walking down the street and there was a homeless person. We were in New York City and he said, hey dad, can I give them some money?

And I, I don't really carry a wallet. I usually just stuff some cash in my pocket whenever I'm places. I don't use cash that much, but luckily I had some cash and so I had like a couple hundred dollars in my pocket and so I pulled it out and I gave him like 20 bucks. And he goes, no, give it all to me. And I was like, really? It's like, yeah, we have plenty. And he just went and gave the guy like 350 bucks. The guy just like exploded in happiness. And my son was beaming. And I was like, that might be the best 350 bucks I ever spent right there. I mean, it was like, made me so happy that that was his, it was, it wasn't even a question of how much it was like, no, we give him everything that we have in our pocket. And so I thought that was really cool.

The other part of your story that I enjoyed reading about, maybe because it's selfishly, it relates to like, I went to college to play football and played a little bit after college as well. And you went to college to play tennis on a scholarship.

Yeah.

And then unfortunately you got hurt. What role did sports play in your life, both doing it, being so good that you could go and play in college, and then also how it was taken away from you by injury?

Yeah. My whole life was tennis. So I actually moved away from home at age 15 to a tennis academy. Like you read about with the Agassiz and the people of the world. I was never as good as them, but I was one of the better players in the country and I loved it. It taught me discipline. It taught me work ethic. And ironically, it also reinforced the fact that I'm not enough, probably because when you're so good at a sport like tennis, then you play the very best people. And so even though I was one of the best players in the state and one of the top, say, 100 players in the country, I just lost a lot because I kept playing the guys that were the very best. And so my whole tennis career, I always say, is like, I just battled a lot of losing. You know, it was basically, I just kept losing. And in college, I was like the last guy on the team, even though I was on scholarship. But it taught me a lot, and I'm really grateful. And I think sports is a great opportunity, especially for kids to learn, especially hard work and discipline.

You know, having it taken from me was really hard because my whole identity was a tennis player. And so that was a very difficult time, but it ultimately led me becoming an entrepreneur. And so I look back now and I'm like, oh, it all kind of happened for a design purpose. But I'm very athletic now. I mean, I still do a lot of sports and it's a big part of my life.

You said it led you to be an entrepreneur. A lot of us probably think of TOMS, but now I'm reading about Easy Laundry, a billboard company like What happened after you got done playing and you immediately go into this, I'm going to start creating businesses mode?

First off, the funny thing is, is I did not know what the word entrepreneur meant after I started my first business, which is Easy Laundry, which I'll share about. And then I was at the bank cashing a check from one of our customers, and the bank person said, man, you're a young entrepreneur. And I was like, I had no idea what that means. Like, I don't know if that's a good compliment or bad. And I actually, 'Cause back when we had dictionaries, I had to go look at a dictionary and figure out what that meant. And I was like, oh, okay, that's cool. I like that idea. I can be an entrepreneur. But yes, I, you know, basically I had this Achilles tendon injury. I wasn't able to really carry things because I was on crutches. So I couldn't carry my laundry down to the facility at the dorms. I looked in the Yellow Pages back then and there was no place that would pick up and deliver my laundry. And so I complained about it. To my roommate's dad at Thanksgiving, and he was an entrepreneur. Now, I didn't know that, you know, at the time.

And he said, I think, man, that sounds like an opportunity, guys. You guys should start a laundry business. And so we did. We bought an old truck from FedEx. It cost us $1,500. We painted EZ Laundry on the side and we opened for business. And that was the beginning of my entrepreneurial life. Within a couple of years, we expanded it to multiple universities. I dropped out of college. And, you know, I never, never kind of looked back. So that's how it all started.

And then you sell to your partner, right? And then you start another business with the billboard. Like, what was this?

Yeah, billboards. That was my favorite one. I mean, I've, I've had about 8 or 9 companies, I guess now, but that, that one was just, it was so great. So basically what happened was, is I was in LA, which I'd never been to before. And it was after my sister and I were on the reality TV show, The Amazing Race. And this is back, like, we were in season 2, and that's when, like, reality TV stars are, like, real celebrities for about 15 minutes. The 15 minutes of fame, right? And so we were there, and we were going to all the parties and doing all the stuff, and we're staying in Hollywood, and one of the things I was amazed at is there are these huge buildings with, like, big advertisements either painted on or hung on the side, like now we see in, you know, Times Square or whatever, and they were these big movies, and it was all entertainment-oriented. And I thought, wow, that's like the most effective advertising I've ever seen. Everyone in town knows the new Jurassic Park movie's out because it's on the side of this building, 50 stories tall.

And at the time I was living in Nashville, Tennessee, and I had this idea. I was like, I've never seen this in Nashville, but we have country music. And I was like, wonder if I could get the rights to put Garth Brooks on the side of a building with his new record release. And if I did, I bet you George Strait's going to want one, or Dixie Chicks, or Amy Grant, or whoever. And so I spent a couple years, it took me almost 2 years working with the city council in Nashville and they would not allow advertising. So that was pretty much everyone normally would say you're dead in the water, right? Okay. No advertising. But I recognized and convinced them that we would never have any ads. So there would be no price for the album. There would be no call to action. But what we would do is country music art. And country music art would be the album covers because they're beautiful things and that would just leave it at that. And I realized too that there was a lot of egos in town. So once I had one, they would all want a huge picture of their new album on the side of a building.

And that turned out to be a great business. I sold it to Clear Channel and that's when I really think I got the entrepreneurial bug. I mean, doing the laundry is what everyone knows. They know that story because it's the first one, but I was bringing in like $30,000, $50,000 a month as a 20-year-old, you know, selling country music art. That's when I was like, okay, I think I've got a gift for this.

How was The Amazing Race? How did you get on the show? I mean, season 2 is early. I love that show. Yeah, early days, early days. How did that happen?

Basically, my sister and I wanted to be on Survivor, both of us, and we both sent in tapes. That's when you sent VHS tapes then to try to get on. And we got pretty far in the selection process, and then they realized that they got down to like the final 20 or 30 people for Survivor, which was already a big feat to get to this final group, that we were brother and sister. And they're like, we can't have a brother and sister on the show, but we have this other show they're perfect for. And so they called us and they said, hey, this show hasn't even come out yet. It's going to come out next year. Basically, it's a race around the world. Do you guys want to do it? We're like, we're in.

Wow. How was it? I didn't see that season. How was it?

Yeah. So it was great. We raced around the world 31 days and we lost $1 million by 4 minutes. And it was my fault.

What'd you do?

So at the end, what happened was we got to San Francisco. Which I had never been to, my sister had never been to, and we were leading the race. There were 3 teams left and we had to get to Pier 31. And I didn't know that the way that the bay is shaped. And so I just said, my sister wanted to get a map and really figure it out. And I was like, we don't have time to go find a store to get a map and all this stuff. Let's just get to the water because obviously the pier is on the water. If we get to the water, we'll find Pier 31. So San Francisco's like this, we're here, we go here, which we really need to go the exact opposite way. So then we had to go all the way around the bay to get there. And, and we still almost won, but we lost by 4 minutes.

Oh my goodness. Wow. Incredible. Well, I mean, Tom's is there, right? So I think a lot of people know the story of Tom's origin story, the success of it. How much of that are you still enjoy talking about? I mean, I don't know if that's the right way to ask the question, or you're like, I just kind of want to move on past that. Where are you at with it?

It's interesting because when I was really suffering mentally after selling TOMS, I didn't want to talk about it at all because I didn't feel worthy of the success that we had. Now I'm extremely proud of what we did. I actually can accept compliments, and I look back at magazine covers and awards in the White House and things, and I'm like, man, I wish I would have enjoyed that more. Like, we did deserve all that. We created a company that changed the world. And now I don't feel like I'm being egotistical saying that, but I really look back at how many businesses have been inspired to create giving or put purpose above profits. And I'm like, wow, that all started after we started Tom's Shoes. Like, so I'm extremely proud of it. And some of my greatest memories of my life are from those 11 years that I was running it. And You know, I'm also excited to talk about the things that I'm working on now.

Yeah.

One of the companies that I'm a co-founder of is called Morning Water. This was something that I did for years myself as a surfer. I would always like make a really big 20 ounces or 24 ounce thing of water and I put creatine in it and I put L-theanine and magnesium and all these supplements. But it was like all these powders all over the place. And my friends would always say, what is that? And I always said, it's my morning water. And then one day my friend Ben, so I really give him credit for this. We were on a surf trip. He said, Blake, that's a good fucking name. Morning Water. I can see that in a store. You should trademark that. And so thankfully I, I was able to, and then I sat on it for 6 years, didn't do anything. And it's a funny story. I was at a men's retreat while I'm at the deepest part of my depression. Like I literally am barely hanging on.. And I'm like, I just gotta get outta the house. And a friend of mine suggested this great guy, Andrew, who runs these men's retreats. He said, just go and get outta the house and be with other guys.

And I did. And I was there. And when I was there, there was this guy, Austin, young entrepreneurial guy. Most of the guys on the retreat were kind of entrepreneurial. He was like a little bit of a fan. He was like, wow. He's like, you're the founder of TOMS. And he's like, what are you doing now? And I'm like, dude, I'm just trying to get outta bed. Like, I have been depressed for the past few years. I'm not in a good place. I got divorced. And he kept pushing me. He kept saying, come on, you have to have something you're working on. And I was like, the only idea I've had in the last 5 years is this thing called Morning Water. And this is what it is. Duh, duh, duh. And he was like, can I do it? And I was like, what do you mean, can you do it? He's like, well, this is great. If you're not going to do it, someone should do it. Like, what if I did it? I'll go finish the formula, get it dealt. I'll come to you. And if you like it, you can invest in it.

And that's how it happened. And so, so we launched Morning Water like 6 months ago and we're actually totally sold out now. You can't even buy it online. We have a waitlist. It's grown so fast. Well, before we thought, but it's been so fun. And so I like, you know, I now I have other things to talk about than just Tom Sheets.

Well, we just got our beautiful packaging pumped.

Oh, great.

You got it.

Pumped. Awesome.

Just got, yeah, literally just mailed. I was, wait, what is this? And then I was like, well, this is beautiful. I'm excited to like dig into it, man.

It's, yeah, it's a, is it 30 days? Just try it for 30 days. Yeah. That's what we tell people. You really need I don't know if you use creatine now, but you really need about 30 days for it to kind of— you really feel the effects and you just take it first thing in the morning. You just put it in water and chug it. And yeah, love it. Love it.

Really, really cool. I want to talk a little bit of like business stuff and business building. And so we can go from any of the businesses, but you were the CEO, but you didn't really want to call yourself that. You wanted to call yourself the Chief Shoe Giver. So how did you balance being the Chief Shoe Giver and being the business CEO guy too? Because I think others may have the passion and purpose behind what they're doing, but the other part is also necessary. And so figuring out how to balance those two could be useful. I'd be curious to hear how you balance those things.

So I would say, as I've reflected on my career, the thing that I'm probably most proud of in terms of how I work, and I think one of the things I'm best at, is finding amazing people to complement my weaknesses. So I am a great storyteller. I'm very creative. I'm very good at sharing a vision, and I have lots of energy. What I don't do well is necessarily run a supply chain or work on the finances, or I have trouble, you know, saying no to everyone, you know, like, so I needed some real guardrails. And so very early on in TOMS, I surrounded myself with people who were who really cared about the mission. You know, there was a woman named Candace who was kind of my right hand on the giving side. And there was another woman named Jill who was the right hand on the sales side. And then we had a great CFO. And I think that's where I was able to truly be the Chief Shoe Giver. I mean, that was, that was a title, but it was actually very representative of what I loved doing and what I did that helped the business the most.

And that was out giving shoes to kids and then telling stories about it. I mean, that was, you know, really what was so unique. And, and it was a very unique time too, because we didn't have the proliferation of messaging that we have now. And so a story like Tom's, I could reach a lot of people through some basic channels like People Magazine, CNN, the New York Times, and then Vogue Magazine. Now it'd be much harder, no matter how good a story you have. I mean, we're seeing this with Morning Water. I mean, my social media presence has helped us get a lot of people and then get other ambassadors, and we're kind of learning that game. But it is definitely different than it was then. But to answer your question, I feel like I've always been really good at surrounding myself with people who are really good at the things that maybe aren't my passion.

I think that's a commonality among leaders who have sustained excellence over time, is they're really good at that part. They're understanding that they become the people who they surround themselves with. So let's get tactical for a second when it comes to hiring. So you're a great storyteller. There are certain areas you're good, and then you have enough awareness to realize there are certain areas where you need help from others to be good. When you're hiring to add leaders to your team, okay, let's broaden that a little bit. Okay. What are some of the must-have attributes that a person needs to be a leader to work with you, as well as what questions are you asking? Like, take me inside the room or the conversations or however you're finding and then hiring these people. What do they have to have? And then what do the conversations sound like to ensure you're not getting fooled through the interview process?

Yeah, this is a very relevant question because this is what I'm doing for Sonya, the AI therapy app right now, because these guys are young, they're 26 years old, they're AI geniuses. They know how to build an incredible product that has helped a lot of people. But when I said, okay, I'm going to help you guys, one of the areas they said is you interview our key people as we're building because they're growing really fast. And that's what I've been doing is helping them. And I think I hopefully helped them, you know, avoid a hire that I don't think would have been a good hire, you know, about a month or two ago. And the way is I really am brutally honest about how hard the job is going to be. And I almost try to talk people out of the job. I mean, I explain, maybe I do it even in a dramatic way because then I'm like, okay, if I can, basically try to talk to this person out of the job and they still desperately want the job, especially at a startup where they're not going to get paid a lot, then there's probably a real commitment to the mission.

Because that's what I'm really looking for. I'm looking for attitude. Is this a roll up my sleeves, I'll do whatever it takes, I'm a team player person? Because that's what's key, especially in a startup. You got to have everyone feel that way. And then the other thing is, is are they looking to be building a resume or do they want to build a movement? So like with Sonia, I was very clear with this person that we were potentially hiring and being like, this has a big, big mission. I mean, these guys think that they're going to change the world of mental health. They're going to provide therapy to people who've never been able to access it. And in order to do that, and especially with the competitive nature of an AI company, we're all working a crazy amount. Even though I'm just advising, I'm still advising well more than I thought I was going to be advising. And so if you're going to take this role, it's going to be your whole life for a little while. And so I think that's one of the things that I try to do is just be brutally honest about the negatives of a role versus a lot of people, I think when they start hiring is they start getting in sales mode of trying to convince the person why it's such a great role.

And then they end up convincing themselves that the person's a good fit. And when really what success I think looks like is how many people did you convince not to take the role before you get the right person?

So you're in there, I assume before they get to you, they've probably already checked some boxes.

Oh yeah. I'm the last one.

You're the last one. So you're the one trying to talk them out. And if they're like, nah, Blake, dude, this is what I'm doing, man. I'm committed. You're looking for commitment and attitude and a willingness to get after it, even when it's really hard and you're not getting paid very much.

Yeah. In this particular situation, obviously, if someone's hiring people and there's a leader of a Fortune 500 company, it might be very different. But I still think, you know, the most important thing of all the things I've learned, and I had, you know, we had 350 employees at Tom's. So I've done a lot of hiring and I've seen a lot of things. 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. And the second thing is, is really attitude that you're the type of person that is not going to say that's in my job description or not. Like you're just like, this needs to get done. Let's figure out how to get it done.

You posted a, I don't know if they're still called like a thread anymore on Twitter, but there's a few of them that I just wanted to riff on. Is that cool?

Right. Yeah, sure.

Yeah. Okay. So one of them is you don't 'Attract what you want. You attract what you are. Want honest friends? Be honest. Want peace in your home? Bring peace. Want trust? Practice it when no one's watching.' So talk to me about— you don't attract what you want, you attract what you are, especially in relationships.

I mean, in business and personal relationships. So the best way to find, in my opinion, a romantic partner is to work on yourself, just to really work on your own inner work, your own issues, and to try to clean yourself as much as you can from anything of the past that's holding you back. So then you can attract someone who will be a good partner. I think in business it's the same thing. I even think your customers, like, I think you attract great customers when you are a really great company. And I think when you're a company that is maybe not the most ethical or not the most forthcoming about your purposes, then you attract crappy customers. And ultimately that is the reason why the business doesn't work. And so I really do believe that there's this— and this is probably more woo-woo, but there is this energetic thing about a person and how they attract other people or, or aspects of the business that really represent who they are at that moment.

It reminds me of that Charlie Munger story. He was speaking somewhere and someone came and was like, hey, Charlie, how do I get a great wife? And he paused and he looked at me, he said, deserve one. And I thought, ah, you know what I mean? You don't attract what you want, you attract what you are.

Okay. I love Charlie Munger.

Yeah, me too. Next one. Don't wait for permission. Most people stand in line at the front door. I look for side doors. In Argentina, I didn't have investors or a plan. I had an idea, one for one. So, but this idea of like, well, they didn't say they were hiring, so I don't know. It's like, no, I try to say this as a dad. I like go, hey, drive to the place, knock on the door, talk to them. Even if it's like, this is a serving job we were talking about, I go drive to the restaurant, go talk to the manager. Everyone can apply online. Everyone can do that. You can't, no, we're not waiting for permission. We're gonna go make it happen. So talk to me about the idea of not waiting for permission.

I mean, I think that's been the key to my entrepreneurial success, honestly. I'm so glad you brought that up because I always say to people, the reason why I was able to have success in the different places I have is I had no experience. Like, I had never made a shoe before. I didn't know the shoe industry. I didn't know any of the rules about shoes, so I was able to break them. I didn't know anything about outdoor advertising or the contracts you gotta have with the different cities and all this, so I figured out a way to do country music art. I had an online driver's ed company. I'd never been in the driver's ed business. At that time, it was all in classrooms. That's where you had to go learn at the mall and the Sears. And so I thought a better way of doing this is online. So, and I really learned that from Richard Branson. I want to give him credit. He's been a mentor to me and I think he's one of the greatest entrepreneurs of all time. And I really learned that first by reading his books and later getting to spend some time with him.

But you know, he loves, I mean, he has a whole book, I think it's called Break the Rules or something, A Guide to Renegade Entrepreneur. And it's a great book. And it really is about breaking the rules, asking for forgiveness, not permission.

Let's do one more.

Sure.

Be known for doing what you said you'd do. This seems obvious, but it's not. People talk and then they don't execute. Early on, you didn't have skills, so your reputation was all about execution, moving fast, keeping it simple, doing it with integrity. Momentum. You're right, I like this momentum. Is a form of trust. Be known for doing what you said you'd do.

Yeah, I think it's just, and even more so than ever, especially for young people, it's like, if you say you're gonna do something, you can't flake. I mean, it's just, it's that simple. Like, it's just like, people have zero tolerance for that. There's, there's someone else that wants a job. There's someone who else wants the gig. If you say you're gonna do something, then you do everything you possibly can to do that. Now, that's important for parenting, that's important for relationships, but I also think it's really important for business and especially entrepreneurs that are trying to get large customers. So for instance, in the shoe business, you know, getting Nordstrom is a huge deal, right? Or getting Journeys is a huge deal. If you don't follow through with exactly what you say you're going to do and ship those shoes when you say you're going to ship them, you're out. So it's really important to be someone— and that's also about don't overpromise either. That's the other thing. I think that's something I have made a mistake in the past. I get so excited. I have some false confidence and I overpromise something and then I can't deliver.

And that's always painful. But if that does happen, just own it and be honest about it. And then you'll have that relationship with that buyer or that customer for a long time.

Okay. This is awesome, Blake. One more question before we point people to where to go. And that is, um, let's, let's fast forward a year. You are exactly one year from today. You are surrounded by all of the people that you love the most, right? Friends, family, everybody you love the most. And you guys are, popping bottles, you're spraying grape juice on each other, whatever it is that you want to be popping, right? You're celebrating like crazy. What are you celebrating?

Hmm. Well, that's a great question. I love that question. I think my, my biggest goal or desire right now is to design a harmonious life. I actually recorded an Instagram post that's probably going to go live on Monday about this because it had something that a woman said. I was just at the Cannes Ad Festival and this woman who is the head of, I think, Google Health said, I gave up on life balance this year and started focusing on harmony instead. And it really struck me because so much of my life I've thought about trying to balance it all. And I think that's like not really who I am. I go really hard and get really excited about things. And so sometimes I am full in dad mode and everyone at the office is like, when are you going to respond to those emails? We can't do this until you respond. And I'm so into dad mode that I don't care. And then sometimes I'm like, you know, when we launched the No Magic Pill podcast a few months ago, I was like all in doing tons of press, everything I possibly could to get that launched.

And I missed some things with my kids. So my point in this is, is what I would be celebrating is if I have found a way to really make it working in harmony and everyone in my life feels that they are getting the attention that they need to thrive, you know, so that's my romantic partner, that's my kids. And that's my business interest. And then myself, you know, I can't forget myself. So, so that's really kind of what I'm— my biggest thing is to really stop worrying about the balance of it all, but look at it like on a year-long kind of experience of harmony. I feel that I'm, I'm on my way. So very cool.

We'll definitely be checking on that in a year from now and I'll be following up. This is awesome, dude. I really appreciate it. Where would you send— there's a few different things you're doing. So where would you send people to learn more about everything you got going on?

Yeah, probably just my Instagram. It's @blakemykoski. And then also I have a website, blakemykoski.com, and it has the list of all the different projects and things that I'm working on. And, and that's how you can find out the best. Yeah, blakemykoski.com or @blakemykoski.

Perfect, man. Thank you, especially while you're down in Costa Rica for joining me. I love this and I would love to continue our dialogue as we both progress, man.

Thank you so much, Ryan.

It is the end of the Podcast Club. Thank you for being a member of the End of the Podcast Club. If you are, send me a note, ryan@learningleader.com. Let me know what you learned from this great conversation with Blake Mycoskie. A few takeaways from my notes: make your gratitude specific. Don't just stop at, well, I'm grateful for my family. Name the exact moment, like that photo of your daughter laughing at camp or a specific text from a friend. Specificity is important. It makes it tangible. It makes it real. That goes for giving compliments, giving thanks. Be specific. Then you don't attract what you want. You attract what you are. You want honest friends? Be honest. Want peace in your home? Bring peace. Want trust? Practice it when no one is watching. As Charlie Munger once said, how to get a great wife? Deserve one. You don't attract what you want. You attract what you are. And then be known for doing what you said you'd do. Blake said early on, I didn't have all the skills, so I built a reputation for execution. Move fast. Keep it simple. Do it with integrity. Follow through on your word.

Do what you said you'd do. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two, hey, you should listen to this episode of The Learning Leader Show with Blake Mycoskie. I think it'll help you become a more effective leader because you continue to do that and you also go to Apple Podcasts and Spotify and you subscribe to the show, you rate it, hopefully 5 stars, you write a thoughtful review. By doing all of that, you are giving me the opportunity to do what I love on a daily basis. And for that, I will forever be grateful. Thank you so, so much. Talk to you soon. Can't wait.