The Tim Ferriss Show Transcripts: TOMS Founder Blake Mycoskie — Fear{less} with Tim Ferriss (#551)

Please enjoy this transcript of my interview with Blake Mycoskie from my 2017 TV show Fear{less}. The “less” is in parentheses because the objective is to teach you to fear less, not to be fearless.

Fear{less} features in-depth, long-form conversations with top performers, focusing on how they’ve overcome fears and made hard decisions, embracing discomfort and thinking big.

It was produced by Wild West Productions, and I worked with them to make both the video and audio available to you for free, my dear listeners. You can find the video of this episode on YouTube.com/TimFerriss, and eventually you’ll be able to see all episodes for free at YouTube.com/TimFerriss.

Spearheaded by actor/producer and past podcast guest Vince Vaughn, Wild West Productions has produced a string of hit movies including The Internship, Couples Retreat, Four Christmases, and The Break-Up.

In 2020, Wild West produced the comedy The Opening Act, starring Jimmy O. Yang and Cedric The Entertainer. In addition to Fear{less}, their television credits include Undeniable with Joe Buck, ESPN’s 30 for 30 episode about the ’85 Bears, and the Netflix animated show F is for Family.

Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Music, or on your favorite podcast platform. You can watch the interview on YouTube here.

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Tim Ferriss: I’m Tim Ferriss, author, entrepreneur, angel investor, and now TV host. I’ve spent my entire adult life asking questions, then scouring the globe to find the answers. On this show, I’ll share the secrets of pioneers who have faced their own fears. Dig into the hard times, big mistakes, tough decisions, and how they got through it all.

The goal isn’t to be fearless. The goal is to learn to fear less. Welcome to Fear{less}. I’m your host, Tim Ferriss, and on this stage, we’ll be deconstructing world class performers of all different types to uncover the specific tactics and strategies they’ve used to overcome doubt, tackle their hardest decisions, and ultimately, succeed on their own terms.

By show of hands, how many of you guys own a few pairs of shoes? That is everybody in the room? How many of you own around 10 pairs of shoes? All right, more than half. How many of you do not own a single pair of shoes? All right, that’s a big fat zero. My guest tonight has built a company that’s given away more than 60 million pairs of shoes to those who need the most.

During a trip to South America, he recognized the unique opportunity to blend business and philanthropy. Since its founding, TOMS has given away millions of shoes, helped restore eyesight, and provided safe drinking water to those in need across the globe. So ladies and gentlemen, please welcome to the stage the founder of TOMS, Blake Mycoskie.

Blake Mycoskie: It’s been a few years, man.

Tim Ferriss: Yeah. So Blake and I met quite a while back, and we’ll get to the origin stories of all that, but I thought what we could do is take a look at one of the ways that I was not necessarily introduced to, but reacquainted with Tom. So we have a video that we’re going to start with.

Blake Mycoskie: Okay, great.

Speaker 3 : It’s incredible to think that five years ago, what has now become a global event started with a simple idea on a college campus.

Speaker 4 : I’m going without shoes, so I can know what millions of children go through every day.

Speaker 5 : You don’t really realize what a luxury we have to have shoes on our feet all day. But it’s actually painful.

Speaker 6 : One day without shoes.

Tim Ferriss: So why would I start with this video? Well, there are a few reasons. The first is that clearly, I think it puts in perspective as one event, the good that Blake, and his company, and all the people involved have done. Number two, this is a master of positioning, and PR, and events, and a lot in between. And we’re going to come back to that and take a look at how it all came to be. But the apple doesn’t seem to fall too far from the tree. Butter Busters.

Blake Mycoskie: Yeah.

Tim Ferriss: Let’s talk about Butter Busters. This is going somewhere. Bear with me. What is Butter Busters?

Blake Mycoskie: So Butter Busters is a cookbook my mom wrote on a word processor in 1993, literally in our kitchen, that went on to sell millions and millions of copies. And it was this crazy experience for me being 15 years old, seeing my mom who was married to my dad, he was a doctor.

He was the breadwinner, all this. The next thing you know, she’s getting royalty checks from millions of dollars from the mail because she wrote a book, mainly because she wanted to help people lose weight, and keep their cholesterol down.

Tim Ferriss: Because she had high cholesterol.

Blake Mycoskie: She had high cholesterol. And so basically, the story was, she went to the doctor, and came home, and had high cholesterol. And the doctor suggested her cutting some of the fat out of her diet. And so she started doing that, and she started losing weight as well. And she wanted to share what she learned with others.

And I think I learned two things from that. One, at that very impressionable age, I just saw my mom had an idea that could help people and she acted on it, even though she had never written a thing in her life. Didn’t graduate from college, just did it. And she didn’t think about it, she just acted. And the second thing was you can start something from nothing, and a fortune can be made out of literally your kitchen and a typewriter.

Tim Ferriss: And did she go to a bunch of New York publishers, and they had an auction, and one of them bought the book, or how did — 

Blake Mycoskie: Yeah. You’ll appreciate this with your story. She felt so connected to helping people, and really reaching people directly that she didn’t even go down the publishing route. She self-published it. And actually, the first time that she published it, the publisher was a crook. And her and my dad lost like $50,000, which was a ton of money to our family back then.

And so she got a loan from the bank to publish it again the second time. And she started selling them literally out of our garage. And her big break was she landed the Sam’s Club part of Walmart. And next thing you know, she was selling hundreds of thousands of copies. And we had to get a little warehouse next to our house, which turned out to be a great business thing because she sold over a million copies before she had a publisher.

Tim Ferriss: That’s a lot of envelopes.

Blake Mycoskie: Yeah. So I had no idea that’s where we’re going to start this conversation, but I think it’s actually a wonderful place to start because so many people after you have had some success as an entrepreneur asked you, where did it come from? Where did the drive come from?

And for me, the drive came more from my athletic background, and all the lessons I learned trying to be a professional tennis player. But the understanding of creating something from nothing, and doing it to help people, clearly came from me seeing this experience at age 15 to 18 with my mom.

Tim Ferriss: Let’s talk about SMU.

Blake Mycoskie: Okay.

Tim Ferriss: All right.

Blake Mycoskie: I was only there for 18 months.

Tim Ferriss: Right. So we won’t spend too much time on it, but you chose philosophy. Is that right?

Blake Mycoskie: Yeah.

Tim Ferriss: Why philosophy?

Blake Mycoskie: Well, I started because I originally majored in archaeology because my goal was to become Indiana Jones. That was my career path. No, it’s like, I was never really that into school. I was a tennis player, that’s the thing. But I thought, “Okay, if I don’t become a professional tennis player, what would I want to do with my life?”

Tim Ferriss: Indiana Jones.

Blake Mycoskie: And I was like, I think Indiana Jones is the best job. So what did he study? Say, archaeology. But no one told me, and I set up all archaeology classes freshman year. And I’m in these classes, and they’re more like chemistry, and we’re studying the compounds of rocks. And it’s the most boring stuff in the world. So I was like — 

Tim Ferriss: No whips.

Blake Mycoskie: — yeah, no whips. So talk about tribes, and cannibals, and all the stuff I was excited about getting into, or learning how to stay away from. So I dropped out of the archeology classes because it was like watching paint dry. And I thought, “Okay. So what else could I be interested in?”

But part of my fascination I think with Indiana Jones and this idea of traveling the world, and discovering people, and ancient ruins, and all this stuff, also came with this idea of understanding world religions, and how we got — why some people think this way, and other people think that way.

And so then that led to, okay, philosophy can be a great place to really dig into from an academic standpoint, and learn why people think different things, how we’ve evolved as human beings. Once I got in the philosophy classes, I actually really loved them because they were pretty quickly into stuff that I felt like was relatable to my experience as a human. And so I really enjoyed philosophy. To this day, when I have time for free reading, I read a lot of philosophy.

Tim Ferriss: Any favorite philosophers or books on philosophy?

Blake Mycoskie: Descartes, I like a lot. It’s one of my favorites, Plato, Aristotle, the classics — they’ve been classics for hundreds of years for a reason. And so I feel like you can read some Aristotle, and it’s literally as relevant as another book you might read to improve some part of your life today.

Tim Ferriss: For sure. Yeah, I’ve been infatuated with, and obsessed with these Stoic philosophers when it was 2,000 plus years ago, in some cases, with Marcus Aurelius.

Blake Mycoskie: Marcus Aurelius. Yeah, Meditations, that book is like, if you really allow yourself to slowly read, and allow those words, and allow those phrases to be imprinted in your mind, that book has more — you could read only that book and have all the wisdom you need probably to live a virtuous, a successful, an adventurous life. That’s one of my favorite books of all time.

Tim Ferriss: So Meditations, just to put it in perspective for folks. Meditations was written by Marcus Aurelius, at the time the Emperor of Rome. So he’s the most powerful man in the world. And they are effectively entries in a war journal. So they were never intended to be published. So it’s his notes to himself, which makes it very interesting. And actually, on that point, do you have a journaling habit?

Blake Mycoskie: I do.

Tim Ferriss: When did you start that?

Blake Mycoskie: When I was about 15. And — 

Tim Ferriss: Why did you start doing that?

Blake Mycoskie: It goes back to tennis. I wanted to chart my progress. That’s how focused I was. I wanted to understand if I was really getting better. And I had read when I was young, about other successful athletes, that part of what they did was they journaled, and they wrote positive affirmations. Pregame by journaling it, it was more imprinted in their mind.

And it’s fun to go back and read some of those journals when I was 15, how serious I was as a 15-year-old. It’s also a little scary. But yeah, I started then. And then, very quickly, it became a form of therapy for me as an early entrepreneur when things were really tough, and if you’re going to make payroll, and you didn’t want to tell anyone, because you realize had to show this error of confidence, and everything is going to be great.

So then at night, I can be scribbling about how concerned I was, and confessing a lot of things that were bothering me, or I was worried about. And journaling has been probably the most constant habit in my life. I do it every single morning. Sometimes, twice a day. But it’s interesting, one of the things I always say to people about journaling is, I think it’s one of the most powerful habits you can create.

Because a lot of the journaling, too, is goal setting. And really having the goals, and then writing about how you’re trying to achieve them. And then, going back and seeing which ones you’re achieving, and which ones you’re not, and understanding that. But the other thing is, you can learn so much about the things that end up working and not working.

You can go back and see what led to the success or the failure of that idea through the journal path. And you can also see those things that you thought were so important end up not being at all, especially with girlfriends, and things like that in the early days. So it’s really interesting. I think you can learn a lot from journaling. And it’s something that I tell people all the time. If there’s one thing that can help get your life on a more positive path, journaling is it.

Tim Ferriss: So this is going to be a bit of a left turn from this — 

Blake Mycoskie: From journaling.

Tim Ferriss: EZ Laundry.

Blake Mycoskie: Yes.

Tim Ferriss: Tell me all about it, so EZ Laundry.

Blake Mycoskie: Well, EZ Laundry, I guess was my first real business. I’m playing tennis, chasing my dreams at SMU, I partially tear my Achilles tendon. So that injury is six to eight months, leg cast, and already, I was the last guy on the team. So eight months of no playing, and new freshmen that are more talented coming in. I started to realize maybe my life path is not to be a professional tennis player.

It wasn’t until a couple weeks later, when my roommate and I were discussing my huge pile of laundry that was growing in our room because I couldn’t do it, because I was on crutches. And so the laundry facility is down in the basement and I’m on crutches. And so it was piling up, and this is back and hard to believe, when we looked in the Yellow Pages for stuff, right?

Tim Ferriss: Oh, I remember.

Blake Mycoskie: And you remember that.

Tim Ferriss: I remember.

Blake Mycoskie: Some people listening or here today might not remember the Yellow Pages.

Tim Ferriss: The internet of yesteryear, yeah.

Blake Mycoskie: Yeah. So I looked in the Yellow Pages for someone to pick up my laundry. And there was — 

Tim Ferriss: The slowest Google ever, by the way.

Blake Mycoskie: Yeah. And so there’s nothing that does that. And my laundry is piling up. So it’s a real problem. And I think this is where a lot of entrepreneurial ideas are born out of necessity, out of some of the service you want that’s not offered. And so I went to school at SMU, it’s a private school in Dallas, and there are a lot of kids who had plenty of disposable income, and didn’t like doing their laundry too.

So I thought, “What if we had this pickup and delivery laundry service, and we call it EZ Laundry.” And the idea is we would basically pick up the laundry, take it to a facility, get a bulk rate with them, and then deliver it back the next day or two days later.

Tim Ferriss: Was it true that you guys would do fake deliveries to dorms to try to create the illusion of having a successful business to drum up demand?

Blake Mycoskie: This is true.

Tim Ferriss: Okay. So can you describe how that works?

Blake Mycoskie: So no one wanted to be first and be like, “Oh, I’m too lazy to do my own laundry. I’m going to have someone else do it.” For whatever reason, the psychological herd mentality in college is very strong. And so we’ve somehow, and how we realized this, but we did.

We thought, okay, if we start delivering even though we don’t need to deliver all day long, and all people see is our truck driving around campus, and me or our employees going into dorms, out of dorms, they’re going to think everyone’s doing this and they’re missing out. And that also led to more customers because they’re like, “Man, I see your truck everywhere.”

I’m like, “Yeah, business is great.” And business did become great because they thought that, “Man, if everyone else is doing this service, then I should be doing it too.” So that worked pretty well, and it really did.

Tim Ferriss: And by the way, this is not uncommon at all.

Blake Mycoskie: No.

Tim Ferriss: So case and point, Benjamin Franklin. So most people think of him for the kite with the key, and so on, whatever might be, diplomat, maybe, who knows? But he was very famous as a printer. And in the beginning days to try to drum up business, he would go up and down the street with a wheelbarrow full of all sorts of different printing equipment back and forth, to show how busy he was. To try and get people to come in, and to drum up business. Turned out very well for you.

Blake Mycoskie: I think it’s such an important point. Because the best ideas in the best companies start always come from an entrepreneur who wants a service that he can’t get, a product that doesn’t exist. It’s a frustration. And the solution is not a business actually. It’s like a crusade to get rid of that frustration. And it really is.

And so I always caution people, say, “You can study entrepreneurship, and you can read books about great entrepreneurs. But if you think you’re going to build a great company, it’s got to start with a dissatisfaction, a problem, an issue and a scratch first, and then you build the business.” But don’t think about, “Okay, I want to build a business, what am I going to build?”

Tim Ferriss: So what happened? 18 months, your tenure was up.

Blake Mycoskie: Yeah. Well, and then what happened was is all of a sudden, we had so much demand for this laundry service we started. And we had customers and not just to SMU, but we started to expand to University of Texas, TCU, Oklahoma, and it was clear that there was all this demand. And I was like trying to do my homework at night, running the business during day.

I think we had 30 employees at that point. It was just too much. But yeah, I dropped out. And there were so many days after I did, I was like, “Oh, my God, I want to go back to college so bad; it’s so easy.” Because all my friends are going to a few classes, and drinking beer, and goofing off. And I’m like dealing with these 15 people’s lost jeans every week. And so it wasn’t glamorous by any means.

It’s only glamorous in hindsight, when you’re like, yeah, he’s a college dropout. Bill Gates is a dropout, Michael Dell is — it’s a nice badge to have now, but it definitely wasn’t then.

Tim Ferriss: I have to ask because I honestly don’t know the answer. How did reality TV come into all this?

Blake Mycoskie: In 2001, my sister and I were on the TV show The Amazing Race. I was 25 at the time. And this is the beginning of the reality TV craze and we’re still frankly in. It’s hard to believe all these years later. And really, this 15 minutes of fame. This is a real thing. So all of a sudden, we’re being invited to be on all these talk shows, late night shows, Jay Leno, invited to Will Smith’s birthday party, just this weird stuff.

Because everyone was watching the show, and we’re really one of the interesting characters on the show. And what I found was as I was thinking about this thing was that after the 15 minutes, they moved on to the next season, there was still value, and the entertainment value in the public’s interest in these people.

The network has had to move to the next one because it was time to promote the next show. So my idea was, is why not have a cable television network that would be 100 percent focused on reality? And now, I knew we couldn’t get the big-ticket shows, but I knew we could get the stars after. Because there’s nothing worse than losing your 15 minutes of fame. You’ll do anything to keep it going.

So I could get these people to come on shows for nothing just for their own — it’d be exciting that people to be interested in them still. And then, possibly, you can even create shows that are based off the characters, and then we could — well, I knew we could do is we could buy clips of the shows.

The part that I didn’t know anything about, and which reason this business became a huge disaster, was there’s only five or six companies in the country that controlled the distribution of the content. And so when we went to Comcast, and Time Warner, and DirecTV, and all the different ones, and they’re like, “Well, we have 500 channels right now. Even if people love your channel, it’s not going to change our business, but we’re going to have to pay you for this content. So we’re not that interested.” And it was amazing. It’s such a great business lesson that look, we had a product that the end customer wanted. And we could make amazing content that they actually really probably cared more about than the other 420 channels.

But because the person who was controlling what they saw didn’t have a business reason to do it, we could never make it work. And so after a couple hard years, and running through millions of dollars, and a lot of it is my own money, we had to go out of business. But I wasn’t done. Even though I shut it down, and paid back investors, and fired 40-something people, which was horrible.

I wanted the community go. And so I went into the note first, and only time in my life, where I’ve had actually, some real depression, and got on antidepressants, and things that I never thought in my life I would experience. It wasn’t because of so much that we had failed, and that we had lost money, and we had to fire people, and all that. It was because I still wanted to do this, but I couldn’t.

I couldn’t solve a new way to do it. And so that was a tough four or five months afterwards, which I ultimately got through. But man, what a great lesson. The thing is — 

Tim Ferriss: Where were you at the time? You were in L.A.?

Blake Mycoskie: I was in L.A. And so I think the lesson is you’re thinking about business ideas. It is definitely when I think about any new thing, even within TOMS now is like, no matter how good your idea is, you have to make sure that if your success falls in the hands of a few companies, that you don’t even start to go forward unless you can make sure that at least you get one of those companies as a customer.

And that’s why, I think, it was so great. We started TOMS, and shoe business, or apparel or whatever. There are thousands of stores that could potentially buy your shoes. So it wasn’t like I had to get one of the big guys early on. You could just get a couple, and then build from there.

Tim Ferriss: Yeah, you do risk a whole lot. Now, I want to come back to, if you don’t mind, just that period of depression. So I’ve had extended bouts of depression. It runs in my family. And not going to blame it on that, but that’s probably a component. What was it like in your darkest periods during those five months?

Blake Mycoskie: I think the hardest thing was is like not wanting to get out of bed. I’m a very energetic person. I like usually jump out of bed with both feet on the floor, well before the sun has come up my whole entrepreneurial life. And not having a business to go to, having just lost a lot of credibility with potential investors, or because I was now a failed entrepreneur, not just a successful entrepreneur, and having run through a lot of my own financial resources, it was like, “What am I going to do today?”

Tim Ferriss: What did bring you out of it? What were the things that helped get you back on your feet?

Blake Mycoskie: At the time, I was reading a lot of Richard Branson stuff. And I read Losing My Virginity, which was a great book, if you’ve never read it.

Tim Ferriss: Yeah. It’s a great book. It’s one of the books that kickstarted me.

Blake Mycoskie: Yeah. And I loved his approach to taking businesses that had been around forever, and turning them on their head by basically just making them fun, sarcastic, sexy, et cetera. And so I looked at the driver’s ed business, and this is something that’s been around since my parents learned to drive.

And they were brick and mortar buildings. They were usually connected to a sewerage or something. And they didn’t try to accommodate their students. They just pushed them through this like cattle. So I did two things, it’s called Driver’s Ed Direct. And this is how I got the swagger back, because I really got excited about this idea for a number of reasons.

The first is we were going to have no classrooms. So we’re just going to eliminate that cost, and all the classwork would be online. Now, they would have to learn to drive in a car, but the online part, they would make it fun, and then we’d do it online, and we would make sure they’re paying attention because they couldn’t get to the next part of the class until they pass real time quizzes.

But the second thing I did, and this is where I think was the thing that really made it take off, is I recognize, in Los Angeles, you have a lot of models and actors that need part-time work. And they need flexible schedules. Instead of these teenagers learning from old ladies, what if they’re learning from Abercrombie & Fitch models? That’s going to keep a teenager girl’s attention.

If this girl has this hunky guy teaching her to drive, she’s going to pay attention to him. And she’s going to tell all her friends on MySpace how hot her driver’s ed teacher is. And this is the same thing for the guys. And so we hired the hottest models and actors who needed part-time work in between auditions, we were totally flexible with their hours. And it went crazy on MySpace. Every kid is like, I think people signed up who’d already completed driver’s ed just because they — it was crazy.

Tim Ferriss: So we talked about Driver’s Ed Direct.

Blake Mycoskie: Yeah.

Tim Ferriss: Then, in 2006, you went to one of my favorite places.

Blake Mycoskie: A place well, you know well.

Tim Ferriss: Argentina.

Blake Mycoskie: Yeah.

Tim Ferriss: Why did you go to Argentina?

Blake Mycoskie: I would take the month of January off every year, no matter what. No matter what was going on business wise, I would take a month, I would go somewhere that was totally different, have a totally new cultural experience, get away from work, and then come back, and then just immerse myself for 11 more months, and have that month to look forward to.

And so I decided that for my month, this year, in 2006, I would go to Argentina. One thing that I had already noticed, and already had a big impression on me, and this started when we were on the Amazing Race, but even more so in Argentina, was just how much poverty there was only an hour outside the city. And there were kids on the street, not wearing shoes — 

Tim Ferriss: The shanty town.

Blake Mycoskie: The shanty town.

Tim Ferriss: Yeah. It’s like Slumdog Millionaire.

Blake Mycoskie: Exactly. It’s exactly what it looks like. People living in homes built of aluminum siding, no electricity, no water. I couldn’t believe it. And it was on the third week that I was there that I was in this café, this wine café, and I heard some women speaking in English. And they had been doing volunteer work. They’re working with this nonprofit in Argentina.

And one of the things that they were doing was a shoe drive. And they explained to me that it was getting time, about time for school again, the next semester. And there were many kids that were not able to go to school because they couldn’t afford the uniform, or the shoes. And shoes is part of the uniform. They had to wear a closed-toe shoe.

And so I agreed to go on this trip. Man, and they picked me up a couple days later, and we got in a van, and we had a big U-Haul full of shoes. And we went to this town. And at first, not having ever done anything like this, I was a little bit just standing back and watching. And these girls, they were just right on their hands, and knees, and putting shoes on kids, and giving them hugs, and it was just like this joyful thing.

So I very quickly just jumped in, and started trying to figure it out. And I remember that night, I came home, I’m staying at the polo camp still, and my polo teacher, Alejo, he asked me where I was that day because I wasn’t playing polo. And I said, “Actually, I did this.” And he’s like, “Did that on your vacation?”

And he says to me, “Blake, it’s awesome that you guys gave them shoes, but you’re leaving like in five more days. And these women are going back to their countries. Who’s going to give them their next pair?” And I was never prepared for this question. And when he asked this question, because he’s like, kids’ feet are going to grow fast, or they’re going to — it’s the only pair, they’ll wear out of them.

And if they need them for school, you’ve now given this pair, but who’s going to give them the next pair? And at that point, I actually questioned whether we had done anything good at all. Maybe what we did that day was just made ourselves feel great, because we got this great feeling and, “Oh, my gosh, we did something nice for someone, and they loved on us,” and we left feeling so full.

But if we just set up a future disappointment, we’d actually cause more harm than good if there wasn’t a way to sustain these kids in shoes. And so talk about some difficult moments in life, I remember going to bed that night having that joy and excitement almost ripped out of me, and thinking, gosh, I don’t know what the answer is. But there’s got to be something, a way to make sure these kids get their next pair of shoes.

And so the next morning, woke up, got the journal out, I have my cup of coffee, sitting on the farm, where the polo camp was. And I was just writing in my journal, and I was saying, maybe I could go and ask all my friends to donate 50 bucks a year, and that would buy four pairs of shoes. And that way, every three months, they get a new pair, or we all have too many shoes in our closet.

I’m sure we could all get rid of half of our shoes, and we would not have any effect on our life whatsoever. Maybe I could get those. And I started thinking, but adult sizes are different than kids’ sizes, and all these things. And I just quickly got to the part of like, I don’t think charity is the answer. I don’t think asking for donations or handouts is really going to sustain this.

Now, this might work for a year or two. But then, it’s going to be even a bigger problem if I don’t get the donations or don’t get the handouts. And then, that’s when my mom — 

Tim Ferriss: And not only that, but you have to spend all your time fundraising, and not focusing on building out the organization and so on.

Blake Mycoskie: Well, yes. But at this point, I’m not even thinking about an organization. I’m thinking about 250 kids. I’m only emotionally connected to 250 kids, not in the world thinking about anyone else, or the fact that there’s kids in Cambodia that don’t have shoes, or kids that have frostbite in Mongolia, or kids that have Podoconiosis in Ethiopia, man, I know nothing about any of this at that point.

But I do care about these 250 kids. I spent all day with them, I connected with them, I saw the joy that they got. And so in my journal that morning, I just turned in a pretty natural flow to business. Every year of my life for 10 years, I’m now 29 years old. So I’ve been an entrepreneur for 10 years. And I had used business to solve problems. That’s the way I looked at entrepreneurship.

Something I don’t like, as we were talking about earlier, or something that I don’t think is fair or right in the world, let’s see if we can change it with business. And so I was just writing in my journal. I said, “What if we started an actual business that had a very simple model. You sold shoes to people who wanted them, and you gave shoes to people who needed them.”

And we’d caught one for one. And that was like, just literally, this much of one of hundreds of journals. But as I’m finishing that thought, the great Alejo, and he’s one of the greatest human beings you’ll ever meet, most enthusiastic people I’ve ever met.

Comes up, and he says, “It’s time for breakfast before the polo match, da-da-da. You’re running late. Let’s go, let’s go.” And I said, “No, Alejo, I think I have an answer to your question.” I said, “Instead of a charity, what if there was a business that sold these shoes, that you guys all wear here in Argentina, and that we don’t have in the United States…”

Tim Ferriss: Alpargatas.

Blake Mycoskie: Yeah, the alpargatas. You remember when you were there. And every time we sell a pair, we give a pair. And over a month, we got the first — it was 250 pairs, were the initial prototypes. Because there were 250 kids in this village that we wanted to come give another pair to after we sold them.

And we stuffed them in three duffel bags we bought at the local, equivalent of footlocker, and put them in, check them in, and got through customs somehow without getting confiscated. And literally got them back to L.A. in my apartment in Venice.

Tim Ferriss: How did you get your first retailer, your first key retailer, if that makes sense?

Blake Mycoskie: So I was going just cold calling these stores. When I found out really quickly, if you emailed, or called a store, and said you wanted to sell them shoes that they didn’t know anything about the brand, you never got a response. You had to go there in person. So I was going in person, but very often, I was going to person on the weekends, because during the week I’m running the Driver’s Ed company still.

And so there aren’t usually shoe buyers working on the weekends. It’s just staff. But luckily, I got on American Rag on a Saturday. Courtney was working that day. And so she’s like, “Yeah, I’ll look at it, whatever.” And she’s a pretty curious, cool, interesting person. And I started the shoes. And even before I get to the story, she thought “This is cool.”

They’re a very progressive fashion retailer. They like the new thing. And she’s like, “I’ll buy.” She’d say, “How much inventory do you have?” And I was like, “Well, I’ve got 210 pairs left. I’ve sold 40 to friends and family, a couple online at a little rinky-dinky website that my parents are reordering from, from Texas and stuff.” But she’s like, “I need a way to tell the story.”

And so I showed her a picture, and she put it by the display. And on a piece of cardboard, we wrote what we thought was our mission, and that was with every pair you purchase, we will give a pair to a child in need, one for one. And we put that there and she bought, I think, 85 pairs, which was a third of my inventory, which I was super excited about.

And the funny thing about that, and that led to so many other things. But the main thing that led to was a woman from L.A. Times saw these shoes. And saw on the cardboard that we’re going to give away a pair for every pair we sold. And this woman’s name is Booth Moore. And at the time, she was the leading fashion writer at L.A. Times, and one of the most syndicated fashion writers in the world.

Everyone read her columns. And so she asked Courtney for my information and Courtney gave it to me. And I did the interview, and was super excited. But I didn’t really have an idea of what this would potentially do to what we were calling this at the time as a project. We’d even call it a business. It was the TOMS project. Because I had a business, it was the Driver’s Ed business. This was the project.

And so I didn’t know what was going to happen with the project when this article came out. But two weeks after the interview, on the cover of the L.A. Times, there were two headlines. This is the calendar section. It was Da Vinci Code Opens with 300 Million in Box Office Sales, which people in L.A. care about these things. And then, the second thing is TOMS Shoes.

Listen to this. We sold 2,200 pairs on our website before noon that day. Now, I only had 130 pairs in my apartment. So this is the first of many supply — 

Tim Ferriss: This is the good news/bad news.

Blake Mycoskie: Yeah, this is the good news/bad news. So it was crazy. Had this little article, it wasn’t a big article, had this response of people in Los Angeles to go on this little tiny website, and somehow trust it, and buy shoes. And the website says you would get your shoes in four to five days because we’re just shipping them out of my apartment one at a time. So now, I have an order for 2,200.

We’ve already charged people’s credit cards, by the way, because it just automatically goes through. I have no idea if Alejo and Juan can make these shoes. I don’t even think they think they’re ever going to see me again. And so I literally landed at the airport, I’ve got a little duffel bag, they’re like toiletries, maybe two things of clothes, and the L.A. Times.

And I’d take a taxi directly to Juan’s house, they’re both there, drinking their maté like everyone does in Argentina, just totally chilled out. They’re like no problems in the world. And I right come in, like bat out of hell. And I’m like, “Muchos zapatos, rapido.” That’s all the Spanish I knew. And that’s all the Spanish I needed. And I shared that article, and they just couldn’t believe it.

And so Juan calls his friend, and their friend, and next thing you know, there’s all these different Argentines making these shoes as fast as they can in the garages, which ultimately became a Barnes, became our first factory down there. Two weeks later, and let me just preface this because it’s important to understand, get a picture of what our apartment’s like at the time.

So we had this apartment in Venice, and I have three interns. So two weeks after that article comes out, I’m walking by, it was in the kitchen. I’m walking by the kitchen area, and the phone rings. So I pick it up and say, “Hello, this is Blake, TOMS Shoes.” And there’s this guy on the airline. And you can tell he’s a little bit agitated from the first minute.

And he says, “Yes, yes. I need to order 100 pairs of women’s TOMS. I need red, I need blue, I need natural. And I need them to go out tomorrow.” Now, I’m like, “Whoa, we’ve had people maybe order two or three pairs, but 100 pairs, one person, this doesn’t make sense.” Because all we’re doing is selling online at this point.

And I say, “Well, gosh. First off, this is amazing, 100 pairs, who is this? Where are you calling from?” He says, “Oh, yes. I’m the assistant women’s shoe buyer at Nordstrom in Seattle, at the corporate office.” Now, I don’t know a lot about shoes, but I know that Nordstrom is the Holy Grail of shoes at this point. People had been talking to me about Nordstrom, Nordstrom.

And I know that they don’t call you at your apartment. You beg to get a meeting with these guys. So I’m a little bit like, “Is this real or is this a prank?” But I can tell this guy is really focused on this order. And so as I’m thinking about this, I realize we have no shoes. We sold out. So I had said to the guy, “Okay, this is awesome, 100 pairs. We can do that. That’s probably going to be about two or three weeks.”

He’s like, “No, no. I need them tomorrow. My boss wants them yesterday. I need them tomorrow.” And I’m like, “Well, we’re sold out.” And he goes, “No, you can’t be sold out. Just bump someone else’s order. This is Nordstrom calling. No one tells us we’re sold out.” So I’m like, “Okay, sir. But I don’t think you really understand this situation. I can’t bump someone else’s order. I literally don’t have any shoes to send you.”

And at this point, the guy gets pissed off. This is what he says to me, he goes — and my phone is about to start beeping. And he’s like, he goes, “Listen, buddy, if you can’t help me, put me in touch with the sales department.” But the best part of this whole thing is, while this conversation is going on, my three interns are sitting there eating breakfast tacos that they just got from Rose Cafe.

And one of the girls, Lina, is laughing because she can overhear this conversation. And after that, I didn’t really know what to say. And so she’s like, “Blake, give me the phone. Give me the phone.” So I literally — it’s about to start beeping, so I just toss it to her anyways. These are my favorite moments in the history of TOMS, without even blinking or hesitating. She just goes, “Hi, this is Lina, head of sales.”

Tim Ferriss: We’re going to pull up a photo of early days. Some TOMS, I think, in one of your original apartments.

Blake Mycoskie: I have a funny story about these bags, too.

Tim Ferriss: Let’s hear about the bags.

Blake Mycoskie: So these bags almost sunk the company. Literally, we were almost out of business because of the bags. And most people don’t know this. And I’m glad you showed this picture because it’s something that never comes up in interviews. I actually had two big ideas of the TOMS. The first idea is that we were going to give a pair to a kid for every pair we sold, and we’re going to help kids in Argentina who needed shoes to go to school.

That’s the idea that became famous that people know us for. The second idea is we were going to be the first shoe company to eliminate the horrible waste of cardboard boxes. Think about when you buy a pair of shoes. What do you do with the box? You throw it away. And most of you probably don’t even recycle it. It is hard. It’s not easy to recycle sometimes.

And especially 10 years ago, very few people were recycling stuff like the boxes. And I hated the fact that there were so much waste being created by the shoe industry. And so I got these recyclable bags, linen bags that were made of materials that can be repurposed. And also, it can be used for something, you could put stuff and whatnot.

And so we are going to be the first company to own these bags. So that worked great when our initial sales were online, because someone would order a pair, you stick the bag in the box, or the FedEx envelopes, or whatever you sent, and you send it. And you did not have to waste another box. But then, when we got into Nordstrom, they said okay — we were just trying to get some press, were in Vogue, it is exciting.

They’re like, “Okay, we’re in, and we’re going to give it a shot. We’re going to be five stores in Southern California.” And they said, “But we need boxes.” And I was like, “No, there are no boxes.” And they’re like, “Yeah, but you don’t understand. The way that our business works is we have stock rooms. And every brand gets a stock room, and they have boxes by size. And so when someone wants a seven, they come and get the seven, it won’t work with bags.” And I’m like, “Well, then we’re not going to do business.” And they’re like, “What?” And I’m like, “Well, we’re not going to create waste in the world with these boxes. So we’re going to use these bags.”

And the buyer was just like, first off, I don’t think anyone ever told Nordstrom they’re just not going to do business. But once again, I wasn’t thinking of it like a business. And I was adamant about this bag thing because I was getting really good feedback, because people love the fact that — they connected with this idea.

So anyway, the guy who was a buyer said, “Fine. We’ll try it. But I’m telling you, this is going to be really — 

Tim Ferriss: Hard to stack bags.

Blake Mycoskie: — really hard to stack bags. And if our associates who make money on commission have trouble getting your shoes, they won’t sell as well.” I was like, “Well, let’s just give it a shot.” So the first week, it’s actually pretty easy to stack bags. Our sales of the first week are doing great. I’m calling, I’m so excited, whatever. Second week, it’s like an abrupt halt.

I don’t think a pair sells. And I’m like, “What happened?” And he goes, “Go to La Brea and Nordstrom, and look in the stockroom.” I go in there, it’s a tangled mess, because each bag has a string, and then a tag on it, and they get caught. And literally, you can’t pull these bags apart. So now, when the customer comes in, and says, “I want a size seven.” The person is not going to waste their time and lose commission. It’s like, “Well, how about a pair of Vans instead?”

We’re sold out. That was the thing, everyone was saying they’re sold out. They’re not sold out, they’re in there. And so literally, Nordstrom said, “Until you get boxes, no more business.” And so we actually got kicked out in Nordstrom’s. It took us about six months or so before we finally got into boxes, because it wasn’t so easy getting any old box, we want to design the box and all this.

And so literally, it’s so interesting because I feel like in business, breaking rules sometimes leads to innovation, and new companies, and all those things. But you’ve got to know which rules to break because there’s some rules that you just can’t break. And we have boxes today. And it’s funny. Those early memories are so great, but hopefully, it shows other entrepreneurs, and people thinking about businesses.

They all start in a garage, in an apartment, with an idea, with a group of people who believe in it before anyone else, you struggle with all these crazy things. And then, if you just keep at it long enough, enough good things start happening.

Tim Ferriss: So what I want to do, we have — there’s so many things. We could go for five-hour talk here. But before we do that, what I like to do is take some audience Q&A.

Blake Mycoskie: Great.

Tim Ferriss: So we have some questions that were gathered during the break. And so I’m going to start with, as an entrepreneur, we all face fear. What was your greatest fear in business? And then, part two, what does failure look like to you?

Blake Mycoskie: That’s a really good question. So I had different fears of different businesses. But I want to stick to TOMS because I think it was probably the most motivating fear. I think, sometimes fear can paralyze you in business, or in life, or in relationships. And sometimes, it can be the greatest motivator and the greatest catalyst for success.

So I go to Argentina after that first giving trip. We’ve given 10,000 shoes. We originally try and do 250 kids. So 10,000 is amazing, right? But also, what I created now is 10,000 kids need another pair of shoes. So the very problem that I was trying to alleviate through the business idea actually was exasperated with that initial success. Because I was not thinking about 10,000 kids when I had 250 shoes made.

I was thinking something that seemed very manageable. And that is these 250 kids, getting them shoes. But now once we sold and gave away 10,000, I left that trip, not as excited as I should have been. I left thinking, “Oh, my gosh, I can’t let these communities down.” They think we’re coming back in four months and giving another 10,000 pairs of shoes away.

So I’ve got to make sure that I can sell the shoes and frankly, I didn’t know how I was going to do it. We had had some luck with this media, and we got some momentum, but there was no guarantee that anyone was placing more orders for 10,000 shoes. And so I remember, I was barely sleeping, I was definitely not healthy in terms of the hours I was working.

And it wasn’t because I was loving it, or it was fun, or I was having the high from the joy of the kids. I was literally afraid of having to go back there and be like, “We don’t have any more shoes, and we only sold 2,000 pairs. So only 20 percent of you get shoes.” So fear really was a motivator. And has been in many different chapters in TOMS not because I was afraid of failing as a business, I’d already done that before with my reality channel.

But failing other humans is a much heavier burden to wear, especially when they have so little, and they’re expecting so much. So that’s really how fear has been a great motivator for me.

Tim Ferriss: What are two to three books you can’t live without?

Blake Mycoskie: The 4-Hour Workweek.

Tim Ferriss: I did give him a 20 earlier.

Blake Mycoskie: I didn’t have the mental toughness to get to The 4-Hour Body. But in all seriousness, that book was a huge influence, as I said before, which I’m super grateful for. I’d say the books that have had the biggest impact on me in the last few years. One of them is called The Art of Power by a Vietnamese Buddhist monk named Thich Nhat Hanh.

And the great thing about it is it talks about the — when he’s talking about The Art of Power, it’s definitely not the way we think of power in the West. But really, the power of mindfulness and really, of being able to be present in the moment in everything that you’re doing.

And I found that that book, which I’ve read multiple times now, is that a huge, huge, huge influence on just how I try to approach my day, my business, parenting, my marriage, everything. So I highly recommend that book if you haven’t read it. Meditations, we talked about earlier.

Tim Ferriss: Marcus Aurelius.

Blake Mycoskie: Marcus Aurelius is another really, really great one. I think, depending on where you are in your journey, I think both of Howard Schultz’s books are amazing for entrepreneurs. His first book was called Pour Your Heart Into It, it’s the early story of Starbucks and how it was created. And I think it really illustrates a lot of amazing things that entrepreneurs can learn from.

And then, his second book, which was a really important book for me to read at a point in which I actually left the business for a while, and then came back to it was called Onward. And that was about some of the struggles that Starbucks went through, and how they rebuilt the culture in the company in the last 10 years.

And so I’m really thankful that Howard was so vulnerable, and open with that book, because I think it answered a lot of questions I was having at the time as well. So those are a couple of good ones that I would recommend.

Tim Ferriss: And note on Thich Nhat Hanh, the Vietnamese Buddhist monk, he was nominated for the Nobel Peace Prize by Dr. Martin Luther King Jr. Really fascinating guy. And his first book, which was like Meditations in the sense that it wasn’t intended to be a book called, I believe it’s Peace Is Every Step.

Blake Mycoskie: Peace Is Every Step, yeah.

Tim Ferriss: It’s fantastic. It was actually a guide intended to be given to new monks and visitors to his center in, I guess, it was at the time, perhaps it was in Vietnam. He’s — 

Blake Mycoskie: It’s in France.

Tim Ferriss: It’s in France, right. Fantastic, fantastic book.

Blake Mycoskie: Oh, one more just because we’re in California. And it’s someone I’ve also looked up and learned a lot from is, and it just came out with the, I think, maybe the 10 or 20th year anniversary version is Yvon Chouinard, who started Patagonia, Let My People Go Surfing.

Tim Ferriss: Great book.

Blake Mycoskie: It’s a fantastic book about company culture. It also shares some really tough times in the Patagonia ups and downs, that I learned a lot from. And also, I think it was interesting, because when he wrote the book 10 years ago, it was the beginning of internet sales. And it really shows how they did not risk their business by having too much of their sales in one place.

They have a wholesale business, they have retail stores, they have online, they have a catalog. And that’s something that we’ve done with TOMS over the years is to move away from just online to now wholesale, and now, we’re spending a lot of our energy building our own retail stores.

Tim Ferriss: This next one is, if you lost everything today, what would you be thankful for?

Blake Mycoskie: Well, the truth is, it’s impossible for me to lose everything today. Because everything that I have has very little to do with what I have materially. The experiences that I have, the memories I have, the friends, the family, that’s what I have. And that literally can’t be taken away.

And no one’s really asked me a question, but I could respond that quickly because that’s immediately what I think about when I think of the greatest memories and moments in my life. And that’s why this has been so much fun is I’m getting to go down memory lane. And those are memories that even if the business blew up tomorrow, I would still have those memories.

Tim Ferriss: Have your experiences, let’s just say at TOMS, but it could be across the board — and I also want to highlight one thing for folks, which we — well, I glossed over there. I didn’t dig into. So you mentioned all these businesses that seemed to have nothing to do with one another, but what are the meta skills that you’re developing?

You’re learning to negotiate, you’re learning how to attract, and manage talent. You’re learning how to mitigate or evaluate risk. So even though the businesses, the industries seem totally unrelated, the skills he’s developing do carry from one to the next. They’re not domain specific. So how have your business experiences affected how you parent?

Blake Mycoskie: Yeah. I’m really glad you asked this question because it’s something that I have a lot of personal energy around right now. One of the big things is me and my wife have is a monthly calendar date. I say date, it’s really not a date, sometimes a battle. But it usually ends pretty good because we drink enough wine to like — 

Tim Ferriss: Smoothen the edges.

Blake Mycoskie: — compromise, yeah. But the calendar is king. If you have a busy life, if you’re driving hard, and work, and family, the calendar is the king because we put things on the calendar, they stick. That’s our thing. And so we make sure, if I want to say my goal right now is to spend either two mornings, or two afternoons every week at home with our son, just me and him.

Not with my wife. Just we either take him on a hike in the backpack, take him to the beach, just play in his room, whatever. But that’s my goal. And it will never ever happen if it’s a goal in my journal. It will only happen if, in my case, my wife, my assistant and I, all put it on the calendar. Because if it’s on the calendar, you’re accountable to it.

She’s like, “You put this, no meetings, and then nothing is scheduled.” So for me, the way that we do it is very much focusing on booking things, and scheduling even little things, which might seem ridiculous. You put play with your son on the calendar, that could seem — they could come off like really, I don’t know, just off putting. But the truth is, if it’s on the calendar, it happens.

And even if that seems ridiculous, as long as it happens, that’s what’s the most important thing. Yeah. And that’s also beyond just time with my son. One thing that I’ve always had is a lot of hobbies. I love to surf, I love to snowboard, I like to fly fish, I have lots of friends that like these hobbies, we climb together in the summer.

And so it’s the same thing. Just as I’m planning that business trip to Asia, to do a press tour, because we’ve opened in a lot of stores there. If I’m going to give two weeks to that, I’m also going to make sure I’m giving two weeks to doing stuff with my buddies, and making sure I stay connected to them. Because one thing you find as we get older, and especially, unfortunately, this happens more with men, I think, than women, is we really lose touch with our guy friends.

We focus on our family. We focus on our jobs. And that’s one of my dad has always said, one of his biggest regrets is he’s had this amazing life. He focused so much time on his family, in his jobs, and my mom, that he didn’t — when he got older in his 40s and 50s, he looked around and he didn’t have guys to really depend on.

And so that’s another thing that I’ve always, since learning from my dad, that have placed an importance on. It didn’t have to be a lot of time, but it has to be quality when you do it. And that usually comes from, once again, scheduling it on the calendar.

Tim Ferriss: Yeah. If it’s not on the calendar, it’s not real.

Blake Mycoskie: Yeah.

Tim Ferriss: For sure. If you had a gigantic billboard, or a side of a building, and you could put any message on it, meaning, getting it out to a lot of people, what would you put up there?

Blake Mycoskie: It’s the easiest question you’ve asked because it’s something that has been — it’s really been my mantra since I was 19 years old. And that is “Carpe diem.” Seize the day. Because we have very little control whether we’ll be on this planet tomorrow. I could die in a fatal car crash on the way home, and that’s it. And so if I don’t literally live every day as if it might be my last, then I am not doing a service to the life I’ve been given.

And unfortunately, that became my mantra after one of my best friends died in a plane crash when I was 18. And I realized I could do nothing to get him back, but I could honor his life by living every day if it was going to be my last. And so every email you’ve ever received from me, there’s never a yours, or a thank you, or truly, I signed every email, every letter carpe diem, and I have since I was 19.

And some people that don’t know me feel like that’s a little cheesy, that’s a little too optimistic, that’s a little too much to think of, like seizing every day. But I believe that is the mantra that has served me so well because I’ve committed my life to doing that. If I do that, then I’m giving the most I can to what I’ve been given.

Tim Ferriss: Ladies and gentlemen, Blake Mycoskie.

Blake Mycoskie: Thanks.

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