Find Things to Do That Will Change People’s Life If You Want to Stay Motivated with Steven Sashen

Steven Sashen built Xero Shoes from a barefoot-running insight and shares how he stayed motivated after achieving financial security. He credits finding meaningful work, recommends Stumbling on Happiness and Fooled by Randomness, and reflects on why retirement felt empty until he rediscovered sprinting and purpose.
Welcome to this edition of the million Dollar Mastermind podcast. This is where we pick the brains of high achievers from all walks of life and get their hard earned real world insights on winning. I'm your host, Larry Wydell.
I'm talking with Steven Sasha. And the thing is, if you stay.
Engaged, stay in the game to some.
Extent, you keep your staff around you, keep your contacts around you, you stay relevant. And then when you get an idea, one thing that will never stop happening to successful people is new ideas. You know, painters always got 40 new painting ideas. You know, mission is always hearing new songs or listening. A comedian is always hearing from. Right.
Always hearing setup material.
I bet you if you ever take time to watch the news, I bet you're thinking, I wish I could get on stage tonight.
Oh, no. But I still write jokes every day. You know, to your, to your point. Oh, wait, I had this thought. It flew right out of my brain. Oh. So my friends ask me, you know, what are you going to do if you sell your company? And I say, I just turned 60 a little while ago. I go, well, I want to. I'm still a master's competitive sprinter. I'm a master's all American. So I go, you know, we're going to do some traveling, we'll do some training. They go, well, I give you right now, there's even money on eight months until I start something new. And my goal is to prove them all wrong. And, and because, I mean, ideas are fine, but I mean, at a certain point, like my wife and I were actually, we were retired. We were cash flow retired from 2000 to 2009. We had enough passive income coming in that it wasn't a lot of money, but it was enough that we didn't have to work for a living. And a friend of mine calls me one day. We had been developing stock trading systems. And he says, I got this system that if you were trading it for about two hours a day, you could make an extra ten grand a month. And I said, brian, I don't need ten grand a month. And he says, yeah, but I mean, it only takes a little bit of time. I said, I don't think you get it. The gap between working a little every day and working none every day is infinite.
Yeah, but what do you say about, you know, well, have you ever put yourself through. Through that stage yourself where you were completely retired? Because usually what I'll tell you, I'll.
Tell you how it goes. All right, well, wait, let me just pause on this. Yes.
Okay. Well, I'm going to tell you how it goes a lot of the time. All right, guys, and this is for the last. These are decades of experience, you know, being in the, in the clubs and the, you know, the executives. Yeah, in the past, it's not a lot of money now, but in the past, the guy would have his company, have his thing, sell out 50 million, 100 million, 200 million, whatever, get the trophy wife, get the yacht, get the plane, travel the world. You know, he's living the life. These are all the things, you know, he wanted to do. Get the dream home and then all the dream things she's got and everything. 18 months, he's ready to commit suicide. Because recreation is not satisfying past a certain point because you're not producing anything. And, you know, so, you know, I've seen guys are, you know, late 70s at the Trump Club in Palm beach, walking around with a, you know, spring in his step in a briefcase. I said, what's the briefcase? He said, he said, unlike most people here, I've got something to do.
I have no question that there will be things that I will do, because when I was in retired mode, there was things that I did, but the bar was raised very high for whether I wanted to do it or not. And money was not a factor in that equation at all. And there's no doubt. But the biggest thing for me right now is that I don't care about knowing what it's going to look like in the future. Something will happen. It's not a concern, but I have no interest in having. In doing it, because I think it's going to make me money. That will be. That will be ridiculous. And luckily, you know, both my wife and I have skill sets that are useful for other people. And even there, the bar will be extremely high for who I would want to hang out with and talk to and help. But, um. So, but maybe, for all I know, I'm going to go to Rwanda and just work at a. At a. At a chimp rescue. Um, I have no idea. So it's not going to be just sitting on my butt eating bon bons, which is a great thing to do for a day every now and then, but. But it's. It's definitely not going to be trying to start a new business, because this is a Herculean task.
It is.
And, you know, not for the faint of heart. And yeah, once you do it, and.
Once you is, it's the. There's an advantage of being young and all the. Because you don't know but there's also. There's also the one thing we can tell those in the way up is make it work and don't allow yourself ever to quit. You know, what I'm saying is get it up to a point, you know, have. You don't want to be starting over every few years through your life. You know, find something, do your due diligence, find an industry find thing that you're really excited about and go for it. And don't.
Yeah, yeah, and crush fingers, because again, there's so many things that are out of your control. Look, let's talk about the last couple years. Trade, war, pandemic, supply chain issues, logistic issues. You know, these are huge things that we had no control over and that could have. And that broke and is breaking a lot of companies. We are, again, very lucky and working very hard that that's not our situation. We're still doing really well. But. But you never know. But. But to your point, my wife has the best line. She goes, there's enough shoe companies in the world. There's no need for us to have started a shoe company, except that our shoes change people's lives. And if you don't have something that's really changing people's lives, then I don't recommend it necessarily. I know there are people who like doing it just for the money. They like the challenge of that. I'm not saying don't do that, but for. For us. You know what gets me out of bed in the morning is hearing from thousands of people saying, this changed my life. And, and also to your point, if you, if there is the opportunity to grow it big enough where you can put yourself in a position where money is not the delimiting factor for the way you're making decisions, then that's a really good gig. And those are rare. And, you know, happily, we're in one of those situations. I mean, the joke that I have is we, we when and if we sell the company. And I don't know if it's a when or an if, my joke will be that we would have done everything in our power not to make this much money. And what I mean is we thought when we were retired from 2000, 2009, we knew how much money we needed in a suitcase under the bed to never have to work again. And we passed that point with this company many, many years ago, but nobody wanted to buy it then, and no one wanted to buy it when we were twice that size or twice that size or twice that size. So we've gotten to a point now where, you know, people are like interested, where they could have had it for pennies on the dollar many years ago, but they just didn't get it.
Well, let me stick an idea in your head. In the fact that you have a lot of contacts, you have a lot of awareness of what's going on in the world where you can make a difference. And as you grow, should you decide to stay in, you can retire from the process. You retire from things that take up a lot of your time, that are annoying, that you get somebody else to do and you wind and Steven. What I always have the idea, the model for me was if I can get seven to 10 people doing the thing that I think only I can do, then I can move up. You know, you're on it.
And look, this is the point in our business where we're doing this as well. So Lena was the operations finance person and, and now we have a great CFO and a great coo. I'm the marketing product person. We have a brilliant product team. But I'm like the, you know, the last line of defense for product. But on the marketing side, I'm the guy and I've brought in people who can do things that I do. The joke is they take over a quarter of what I do and they're overwhelmed and I'm still doing more. So it's going to take, you know, many more people to do what I do because I've just been doing it for a very long time and. But to your point, I'll say it this way. I got approached by a portfolio company. They own a number of brands in the outdoor and apparel space. And they said, and they're big fans of what we do. And they said, well, what would you do if we wrote you a big check? And I said, well, if you want me to stick around and do what I like and what I'm good at, and it's not an 80 hour a week job, I'm happy to do that. But if you don't think you need me, then you can just come visit me on the island you bought. And they said, well, that's a really smart answer. I said, well, well, what do idiots say? They go, oh, it's my baby, I've got a vision. I go, oh no, it's my baby and I have a vision. I have a side hustle selling vision impaired babies. So I know that there's a lot of things where I can remain useful, where it would be fun. And that is the goal is to find a way to do this before.
So what I would say to you, this is just me and you talking, but what I would say to you to consider, okay, consider staying in the game. Because I heard this a long time ago and it actually made sense that five minutes of your time would be five hours of a lot of people's time. And I'll tell you this, with your company and in your company, five minutes of your time is probably going to be worth five months of somebody else in the executive thing. And just, you know, if Gates had been able to, Microsoft would have not gone through their lumpy dumpy stage when he got out and turned it over to Steve, whatever the guy's name is. Yeah. And had Gates been able to figure that out, how I could just stay. Because he's in the CEO, chairman of the board, but it's some kind of executive thing. Because in Paul Allen's book, he talks of a story where Gates was telling him, you know, he said, paul, you can't believe it. He said, I've got my office, I've there, you know, founder, whatever, run it. He said, the day after, I gave up the reins the day after and appointed somebody else, and they're in charge now. He said, I go into my office and making phone calls and I hear him talking out, hear these guys talking down the hallway about an idea. And, you know, he said, it's something right up my alley. He said, I was right on. I had a lot of, you know, know, time invested in this thing. And he said, I rushed out of the office to say, you guys talking about this, that and the other, boom, boom, boom, boom, boom. You know, he had like five minutes worth of insight, you know.
Yeah.
And he said, I could just see from the first word out of my mouth their eyes rolled back in their head.
Yeah.
Now, if he figured out a way where he could have had, still had, you know, that five minutes of impact where they had to pay attention to what he was saying. Because, you know, Gates is not going to run out of his office with something that is not, you know, meaningful. You know what I'm saying?
At the same time, though, I don't know Bill, I haven't met Bill, so I could be talking totally out of my butt when I say this, but he's found the thing about him is he is such a polymath. I mean, he, he is so smart about so many things that if he just stayed just in that role in Microsoft, it wouldn't have allowed him do a lot of what he's doing now where he's frankly making a bigger impact, a more interesting impact. And I would argue probably looking the last time I saw an interview with him and he pulled the books that he carried with him to go on vacation and it was a stack 2ft high. They were so varied and so, so boy in the weeds on any given topic. I would argue that he's probably more satisfied now doing that than he was focusing on what Microsoft does.
Yeah, well, my point for you is that you have those kind of interests and as long as you have and what he's got, he's got that big foundation and then Buffett, you know, Buffett long ago put 35 billion in and you know, putting more. So the thing is, if you get into a situation, I see that a person like yourself I think would be fulfilled in that kind of role rather than go work in Rwanda with, I don't know.
Well, you know, I think, look, you.
Could fund that and you could go down there and show them how to.
Really do that, rather than they'll show me.
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But I get your point and I actually agree because you reminded me of something where I got invited to be part of a think tank for a day. It was around a topic that I knew nothing about. Everyone else in the room, there was eight other people in the room. They were all multiple PhDs. And what became very interesting was that A, and I'm not trying to pat myself on the back when I say this, this is literally just talking about how do you plan your future? A, I had more and more creative ideas than everyone else in the room combined. And B, the part that was really freaky was I knew enough about each one of their multiple PhD specialties to ask them really specific detailed questions about it. When it got, when I got to like the fifth one, the others were going, who are you? And I'm just a guy, you know, who didn't get Ritalin as a kid. So I like to know about a lot of things. And so. No, you're right. I mean, if I could put myself in that kind of a situation, it would be a blast. Now, that said, the end of that day, my brain was shot for a week. It was super fun, but I needed a week off after that. So, you know, who knows?
I'm. I'm reminded when you're saying that a story that I was talking with a music instructor guy was really educated on it, and he said, you know, the thing is, the, the take about classically trained musicians is they can't improvise. And if you take them to. You take them to a jazz club, they're going to be kind of lost. And he said, he said, and that's not true. He says it's not that they can't, it's just they have it. And he said, you give them a. Two or three or four days in there, and they're just going to be humming along with everybody. So they never thought about doing it. And so the fact that the improvised improvisational aspect of your mind is pretty adapted, like, you have to be as an entrepreneur and a comic.
Yeah.
If you're in a academic setting or something, and you're, you know, you're piling up the degrees and you're teaching a particular subject step by step, you're not in there, like, reinvent physics for us today. You know, it's like, no, you're teaching fundamentals of physics and you're in that type, you know, keeping all the blocks stacked like that way. So you're just not used to, you know, they would probably be. They would probably be better on day two, is what I'm saying. Yeah.
You know, look, good jazz guys can do the basics really, really well.
Right.
They don't. They don't not practice the basics. And, and the thing with, with classical people who then, if they decide to, they want to play with jazz, part of what they're doing when they make that transition is sort of something we talked about before is, is basically looking for counterfactuals. Like, here's the way my. Been taught to do it.
Right.
How do I find something outside of that box? And they're. And if they don't know anything about jazz, it can be very interesting because they're not then burdened by an understanding of jazz. So there's this is. I'm. Again, I'm not trying to pat myself on the back when I say this one. I've got a number of patents and a number of design ideas that are in our footwear. That I said to a guy who'd been designing footwear for 40 years, one day, how come no one's done this before me? He goes, because you didn't know anything about footwear.
Ah.
So I was just viewing it from the ground up, literally foot up, and coming up with ideas instead of just regurgitating what other people had done for years.
Right. Because that's the way you have, you know, that's your pattern of looking at things. And it served you well over the years.
It is.
But.
But. But I want to highlight that because it's not just. I mean, yeah, my brain tends to do that, but this is a really good thing to do in general, is like, look for the things that everyone's doing or look for the way it's always been done and look for the way that everything is. Looks the same, and just start asking questions about, what if it was the opposite of that? What, it was 90 degrees off from that. What if it was, you know, 233 degrees off from that and just play with these ideas. Now, I will confess, I've done that a bunch of times with this business and been wrong. I designed a piece of hardware that I thought was utterly brilliant. I spent $20,000 designing it and molding it and producing it. And as soon as we got the first sample, it's like, wow, completely doesn't work. And when I realized why it didn't work, that led me to the much simpler, much more elegant, much better version that works better than what anyone had ever designed, really.
Okay, so talk about, you know, and the one thing about the think tank you don't like, you like to think backwards. The interesting thought is, who put together that think tank because they were smart enough.
Yes.
To get that group of PhDs and throw in the wild card.
Yeah, yeah. It's. It's. It's a very good friend of mine. Mine, who knows that if he needs to hear some. Some idea that no one else had thought of in some context on the. Got a call so that I have a friend who is an academic. And what he does, whenever he's about to go on sabbatical or start some new research project, he calls me and says, all right, rip it apart. And the reason we're good friends is that not because I can rip it apart, but because he. Because we both learn something when we both dive into it and find the implicit beliefs or implicit biases that neither of us necessarily knew about before we kind of dove in there. And he finds that fun. The way I got to wait. I'll tell you this story. One of my best friends calls me 20 years ago, 25 years ago, and starts the conversation by saying, you know what your biggest problem is? And I went, oh, this is going to be good. He says, you like telling people when they're factually inaccurate, logically inconsistent in some cognitive bias, or basically just wrong because you think they're going to go, oh, wow, I didn't realize that. Thank you. He says, your mistake, Bacon. And I. And I. I literally. I went, oh, my God. I. I never put it two and two together that way. You're absolutely right. That's exactly it. He goes, see, you just did it.
Yeah. And this goes back to what you said earlier, is the follow up on. That is eventually they may become your friend again, you know, down the road.
Once they realize do some don't.
They may. Well, may was the word.
Well, you know, I. There's. My friends know that if I say something, if someone's saying something, and I say, do you want to have some fun? You know, that's code for, I'm about to make your brain explode. And I have some friends who are into it and others who are like, no, no, no, no. I believe the earth is flat. That's all I need to know.
You remind me of a manager I had working for me in Atlanta decades ago, and he had a friend, had a radio show where he interviewed odd people. You know, my guy would show up once a month under different guises. You know, he would, you know, he would come in. He would come as the guy who wanted to do away with Santa Claus. We've got to make Santa Claus illegal. And then all the lines, oh, my God. Would fire up, who is this son of a bitch? You know, and then he came in with the thing one time where we got to outlaw cheerleaders. You know, cheerleaders, your old men, you know, and the thing, the fantasies and the, you know, it's not healthy flipping them in there. And then the phone lines would light up.
I have a friend who, Who's a very big deal psychologist who's been on Oprah a number of times. And I said, how do you prepare to get on Oprah? And he says, I think of the most innocuous thing that I teach, and then I think of the most incendiary way to present it. I said, give me an example. He goes, okay. I went on Oprah. I said, my opening line was the best Thing that could happen to a relationship is an affair. The place went insane. And when they finally calmed down, he goes, because an affair, an affair in my experience only happens because of an unspoken truth. And so if you take the opportunity to recognize that and then tell the truth, it could. And what we've seen every time is it brings the relationship together because you've just cleared this thing up and the affair had nothing to do with it and becomes meaningless. It was a red herring. And then everyone's like, oh, because how can you argue with. Tell the truth?
Yeah, let me, you know, let's not, let's not leave part company without me hearing the story of how you got into the shoe business.
Oh my gosh.
At least, you know, fluke. So by the way, I'm gonna, I'm gonna say I'm gonna. People need to go check out is what I'm saying. You know, you need to go check out zero. Is it zero shoes or zero shoes?
Xero shoes.com. although if your computer makes you type in zero, it'll still get to me. Yeah, I mean it's been, it's a crazy story. So I got back into sprinting when I was 45 after a 30 year break. And I was getting injured pretty much constantly for about the next two years. And a world champion runner that I knew, which in Boulder means your neighbor because they're everywhere. He said, why don't you take off your big padded, motion controlled, arch supporting shoes and see if you learn anything from running barefoot. Now I'm not trying to tell people to run barefoot, although it did change my life because what I learned was that I had a form problem that I couldn't feel when I had a big thick padded shoe. And getting out of the shoe, I could feel it. And more importantly, it naturally corrected because basically when you're running barefoot, doing it wrong hurts and doing it right feels great. So that barefoot experience, my form changed, my injuries went away. I became faster. I became a master's all American sprinter. And I wanted that barefoot like experience all the time because it was so clearly valuable. Built up strength in my feet change. I used to have crazy lifelong joke level flat feet. I developed an arch in my fe. And so I made a pair of sandals based on a 10,000 year old design. Something to protect your foot, something to hold it on your foot. That's all you need. I had some, you know, rubber that I got from a shoe repair place, some cord from Home Depot, laced them up and away I went. And people started asking me for Pairs. So I made. They told two friends, they told two friends. And after I made, I don't know, 50 or 60 pairs, a guy says, if you treated a sandal making hobby like a business and had a website, I could put you in a book that I have a contract to write. Well, I've been an Internet marketer since 1992. I've built hundreds of websites. So I rushed home and I pitched this incredible opportunity to my wife who assured me it was a complete waste of time and I was a moron for thinking about it. And I said, yeah, you're probably right. So I, I said I wouldn't build a website. And then she went to bed and I built a website and she kind of growled at me the next day. And I said, look, we had actually started a search engine marketing business because I was literally one of the first guys to figure out search engine marketing back in 1992. And I said, it'll be a case study. I'll own the keywords that I care about in about three months. We'll just use it as a case study. Maybe it'll be a car payment. And I was wrong. It only took me six weeks. And it was clearly going to be our full time job right away. And so that's how it began. And you know, and my wife, being a brilliant person that she is, when she saw that it was going to be a real business, she says, okay, I'm all in. I'm in charge of finance and operations. It's like, great. And so that's how it all started. Out of the floor of a corner of a spare bedroom in 2009, where we literally had a debate about whether we should buy a table to get shit off the floor. And then another discussion about whether we should get a second table. And then, and then here we are 13 and some odd years later with 70 employees and, you know, a full line of casual and performance boots, shoes and sandals that people use for anything you could think of.
Well, your first, your first clients came from passive. You know, they saw you and they ask you now, how did you go from, from passive to now we're going to be selling this stuff. Do you remember what your first step were?
Oh, yeah.
First steps.
It was simple. A, built a website and B, made videos showing how to rip off my entire company, literally. Here's how you can do it on your own. You don't need to buy anything from me. If it's easier to buy stuff for me, here's where to do it. And so I put Those videos everywhere on the Internet. And I, and I got involved in conversations about this whole barefoot running, natural movement thing without trying to sell anything, but just try to offer as much value as I could. Not just about coming to buy our stuff, but literally, you know, I was one of the few sprinters in that world, so I just wanted to contribute as much as I could. And basically, it's a variation of a thing that a marketing guy told me years ago. He said, if you want to make money, it's really easy. Figure out where the money is flowing and get in the way of it.
Yeah.
So in the same way, figure out where the conversation is flowing, where people are having problems and get in the way and offer solutions. And that's what I did.
Now, were these short videos were there. You know, you said videos in the.
Early days of YouTube, you, you had. The video had to be under 10 minutes. So I had like, I made three videos that were like, part one, part two, part three. Because that's how long it took to teach someone how to make a sandal from scratch. And, and so, no, they weren't short. And this whole idea about short videos, that people only want to watch short videos, I've proven that wrong again hundreds and hundreds of times. Again, when someone says this is the only way to do it, the first thing I do is test the opposite. And I often find that. Not always, but often find that the opposite or basically what everyone's telling you to do is just lemmings. And, you know, if everyone says, here's a way to do it, then you can stand out by doing something different. Yeah.
Well, Stephen, this has been really fascinating. A whole lot of fun and eye opening for me on your shoes, and I'm looking forward to following up on that. And maybe I'll come by and see your place in Broomfield. I'm not that far away.
Come on by. I know a guy who knows a guy. He can hook you up.
Okay, well, thanks so much. And any last words that you want to leave with people as we, you know, because there's a lot of people, and I know you care about people being successful and, you know, you know, the.
The only one I. That I. That occurs to me to reiterate is just, in fact, in fact, I can do it this way. The two books that are my favorite books that sort of snap me out of a lot of wasted time and effort when it comes to business have nothing to do with. Well, one has a little to do with business. One has nothing to do with business. The One that has nothing to do with business is Stumbling on Happiness by Daniel Gilbert. And that's the book that really goes into why our brains are constantly looking to figure out the imagined happy future and why that doesn't work. And there's a TED Talk that he did as well. You can find that if you don't want to read the book. And then the other book is Fooled by Randomness, which was Nassim Taleb's first book. And the subtitle I'm probably paraphrasing is I think the Hidden Role of Chance in Markets and Life. And where he's similar, he's a contrarian. And that's how he made billions of dollars a couple of times by. When everyone's saying, here's the thing that's happening, he's like, well, I'm going to place a bet that they're wr, because if they're wrong, it'll have a bigger, faster impact. And his analysis of cause and effect and how that applies to business was one of those moments where it literally changed my thinking from that day forward.
Fantastic.
Thanks so much, Steven. Wish you the best. And let's check back in down the road and I want to hear about the new adventures.
Well, this adventure's gone for a while, so we'll see where that takes us.
But I mean, how with this company, you know, like it's getting into bigger and bigger areas. Conscious, you know, people are aware of it.
No, no, you said it earlier. You know, the, the business becomes a whole different thing at multiple, multiple inflection points. Right. We're at one of those now. And so it's going to be very interesting to see we are where we are in six months. I mean, just for the fun of it, we had something really fun happen two days ago where someone started texting us photos or images they had taken from dailymail.co.uk of Billie Eilish wearing our shoes.
Really? Wow. Yeah.
How'd that happen? So, you know, we're. And we have a bunch of NBA players and NFL players and, and baseball players. I mean, people like, big deal people in every sport I can think of who are starting to discover what we're doing. So my hunch is six months from now, this will be unrecognizable.
Absolutely. And of course, I, I've got to say, you started your business organically, which is pretty much how Nike got started, you know, because they were looking for a kinda.
Kinda kind of.
Yeah. And so anyway, congratulations and looking forward to talking.
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