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The Unmistakable Creative Podcast

Identifying the Patterns and Underlying Threads of Your Life’s Work with Josh Long

To say that Josh Long is an entrepreneur who keeps himself busy is an understatement. He’s the creator of the to-do list app Cheddar, the podcasting service Simplecast, and oversees sponsorship at the Great Discontent. In this interview he talks to me about the underlying themes and threads of his life’s work and how to identify yours. 


  • Josh’s exposure to entrepreneurship at a very early age
  • Why entrepreneurship is all about creating value
  • The innate entrepreneurial spirit within all of us 
  • Why our low points teach us so much about ourselves
  • Learning to put things in perspective when you’re challenged
  • Why facing your fears head on is the best way to deal with them
  • Looking at your whole life through the lens of design 
  • Finding the things that make you weird to develop your own frameworks
  • The concept of design as a religion 
  • Stripping things down to a core idea 
  • Why should build and create things that you wish existed 
  • Josh’s role in getting projects and funded for The Great Discontent
  • What separates the risk takers from the ones who play it safe
  • A look at the work that Josh did with Seth Godin
  • The cathartic drive that comes from pain 
  • Leveraging the patterns of successful people you admire
  • The difference between getting A’s in life 
  • Why Josh is only focused on serving 1000 people 
  • The role that the story plays in everything you create

Josh Long is a designer and writer with a degree in philosophy and three books under his belt: Execute, Jenius, and Design Evolution. He co-hosts the Happy Monday podcast with Sarah Parmenter, is building the to-do app Cheddar, coordinates sponsorships for The Great Discontent, and is the co-founder of Simplecast.

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Duration:
1h 3m
Broadcast on:
07 May 2014
Audio Format:
other

As you probably noticed this month, we're bringing you our "Life of Purpose" series and revisiting some of our most transformative episodes, tune in to explore expert insights and practical strategies on help, performance, and community well-being, all aimed at helping you achieve personal and professional fulfillment. If you sign up for the newsletter, you'll not only get recaps of the key ideas in each interview, but at the end of the series, you'll receive our free "Life of Purpose" ebook. What you have to do is go to unmistakablecreative.com/lifepurpose. I'm Srinney Rao, and this is the Unmistakable Creative Podcast, where I speak with creative entrepreneurs, artists, and other insanely interesting people to hear their stories, learn about their molding moments, tipping points, and spectacular takeoffs. Hey, Prime members! Are you tired of ads interfering with your favorite podcasts? Good news! 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He's the creator of the to-do list app Cheddar, the podcasting service, Simplecast, and he oversees sponsorship at the great discontent. In this interview, he talks to me about the underlying theme and threads of his life's work and how to identify yours. Josh, welcome to The Unmistakable Creative. Thanks for having me. Exciting. Thanks for taking the time to join us. I've come across you by way of numerous sources on the internet. Things at the great discontent that I know you work on as well as through references from our listeners. Tell us a bit about yourself, your background, your story, and how that has led you to doing everything that you're up to today. Well, I am definitely up to a lot of things, so let me take a deep breath when we can go. How far back do you want me to go? As far back as you feel is relevant to what's led you to today. It was a cool Midwestern night in my mom and my dad, and I was kidding. Basically, my background was, it's always been in business. When I was growing up, my dad started a company in the corner of my bedroom. It was an engraving business. He made employee of the month plaque programs for companies all across the country. Very unsexy business started off making shoe tags for runners. I've always been around entrepreneurship, so I learned a lot. That business built through as a kid, and now it's around 8 to 10 million now, depending on what value you put on what. Do an employee of the month plaque programs. I learned a lot about business that way and just spawned off of that. I'm not involved in that business anymore. I fell in love with design, so I ran with that. Currently, I own two apps, One's Cheddar, which is a Do app. It's a Mac app, Rails app, iOS app. I also own Simplecast with John Buda. It's a podcasting app, actually. You just upload your audio, it builds a site for you and everything. It's a great app. I run patterns school, which I worked with Seth Godin back in July or August of last year. He helped me start this school here in Wilmington, North Carolina, where I live. It's just running, man. That's about it. I helped Ryan and Tina over at the Great Discontent, and I just wrote three books last year. I also do the Happy Monday podcast with my lovely co-host, Ms. Sarah Parmiter. Wow. Yeah. I'm a busy guy. Really, I was going to say is when do you sleep? I do. That's it. Okay. I love this. Like I said, I knew that you were up to a bunch of different things, and it was pretty clear from sort of just a little bit of digging that I had done. I want to go back to the very beginning, which I always do. Let me ask you this. I mean, as you're exposed to entrepreneurship at a very, very early age, it sounds like, and I'm always really curious to see kind of how that shaped and influenced the other decisions you've made and the path you've taken throughout your life, I mean, when you sort of destined and groomed to be an entrepreneur, and you know, what are the implications for people listening? I mean, is it, you think this is something that you're just born with or you're groomed to become, and you know, and if not, what do we do to really hone our skills here? Yeah. I mean, I think it's a little bit of everything, right? I mean, a lot of times we tend to kind of lean towards what we knew growing up, like what our parents did. That's just because of what you're around. You know, you hear a lot of people talk about being artists and stuff because their parents were creative and it kind of goes that way. So I don't think you're born with it. I think maybe you're influenced, but to become an entrepreneur, the only way to really do it is to do it and to have tried a couple of things. You know, like entrepreneurship to me is all about creating value. The thing about entrepreneurship is you can take what seems like nothing and create value from that. So, you know, if there's, you know, assets over here that are being untapped or you have a great idea and you said, you know what, I'm going to go out and do it on my own. So it's being an entrepreneur is very much an earned thing and I don't even really like the word entrepreneur anymore. I think it's completely blown out. But you know, it's the only one we've got. So it's kind of like love, right? Yeah. So yeah, in my opinion, man, you just have to do it. And I think we all innately have this entrepreneurial spirit simply because we just want to make things. You know, if we needed tools, we made tools and at some point people got too busy and couldn't make tools. So they went to somebody and bought someone's extra tools and it just kind of kind of went on for that. I just think we all kind of want to see some things in the world and we all have a little bit, at least, of that in us. Yeah. Well, let me ask you this. I mean, how has growing up in that environment influenced the choices that you've made in your life as an adult? Oh, man, that's a good question. I think it trained me to keep my eyes open, you know, to see opportunity. Like, that's such very much a trained thing. And even as a designer, being able to really see through the lens of design and entrepreneurship, they're very much a trained thing. So I think growing up in that helped me to see opportunities where most may not see opportunities. And it also showed me the ups and downs of entrepreneurship. So there's really like, there's two ways to really know yourself, right? Like, you can really learn yourself from fighting someone or being very, very low, like as low as you can get. And entrepreneurship, a lot of it has those lows. And you know, seeing my dad go through those lows and how that affected things, like it affects you in all the decisions that you make, you know? Yeah. Well, okay, so let's talk about the lows and navigating the emotional aspects of a journey like this. Because I think that that's something that it's one of those things that we know, but I don't think we really get it until we've experienced it. And I think some people just get completely destroyed by the lows and they can't keep going because of it. I'm really curious. I mean, in your own journey, can you talk to me about sort of navigating the emotional components of it and where you've run into challenges, how you've overcome them, you know, what were the low points and, you know, what are the high points and then how you keep going through a lot of uncertainty? Yeah. You know, I feel like right now is a high point, you know, everything that I do, it sounds like I do a lot of things, but they're all interrelated. You know, I built things because like simple cast, I didn't like the way my other podcasting software was working. So I got with someone to build that. But, you know, with patterns and the books that they're all feeding each other, they're all my experiences. And I'm just kind of like documenting what I learned as I go. Now the lows, I could tell you a story I haven't told a whole lot of people. Just a couple of years ago, I, once I took a photo, a picture of it with my phone actually, I was in my car. It was like a used Lexus like 300 from the 90s. And I'm sitting there and I took a picture in my steering wheel because I never wanted to forget this moment. I was sitting in my car and I literally had to have five grand by the end of the day or my pregnant wife was going to be without insurance and we were going to lose our house. Wow. Yeah. By the end of the day. So when I say like you get lows and you have to survive as an entrepreneur, like those kinds of things happen and those make you a serious person, I mean they make you a woman, they make you a man, you know, like when you have to do it, that's when you learn entrepreneurship because it's survival. Yeah. So how'd you figure out? How'd you get the five grand by the end of the day? I actually, it was a combination of amalgamation, but it's basically like a huge marketing package for like four different people. It was completely undervalued, but I needed it. So yeah, I did websites, website design, video package and everything and just did it and it was a, it was a day I'll never forget. I was literally like on the phone and in between walking from like different businesses like literally like just hustling to get that five grand and whatever it took. It's interesting how resourceful we become in desperate moments, isn't it? I mean, I think that, like I've noticed, I remember, you know, and I've told this story a handful of times, you know, and other podcasts, when I graduated from business school, I literally had no money and I was getting an allowance from my parents, $50 a week, okay? And I had to make $50 a week somehow last for five days in Los Angeles. I mean, I, you know, I would email the organizers of networking events and offer to work the doors. I would, if I went to a bar, I would take a flask with me, order water, dump it out and pour, you know, the vodka that I had brought with me into the glass. I literally survived on peanut butter and jelly sandwiches, but what that all taught me was how resourceful I became when I was when my back was up against the wall. And it's interesting, but the thing is that I think a lot of people would be in the position that you were in and end up homeless, or at least they think they would, right? I'm because I've seen this narrative that that plays out. I've seen it even in some of my personal Facebook pages. I've seen it on my wall with people. And what I'm curious about is is dealing with that narrative so that a moment like the one you had doesn't break you. I mean, clearly it didn't break you. So I mean, how did you deal with the mental aspects of that? I mean, it's almost a scar that never goes away in some ways, but in a good way. You know, you're right. I think the majority of people probably would have like folded and hoped somehow they got out of the situation and went back and got a job or something, you know, like they probably would have folded. But, you know, I just sat there and it's one of those moments where you kind of just like you sit there and you look in the car rearview mirror for a second, you know, and you just look at yourself and you're just kind of like, there is no other option. Like this has to happen. Everything that you've learned and anything that's going on in the world, so like sometimes when I'm like in that kind of position, I say I've got my health, you know, my kids are healthy, like you just you put yourself in perspective, right? And you say this is not as bad as the majority of the world is going through. Suck it up. Go out there and get it done. You know what I mean? And you can't second-guess yourself and the thing is too is you can't really come across as desperate, right? Like nobody wants to buy from a desperate person. So you do you have all of these and this is part of the reason why I like entrepreneurship. I think it's a lot of it is a game and a lot of it psychology between yourself, you know, being able to empathize with people and figure out their needs and like identifying value. Like it is like it's brain work for sure. So yeah, I mean, it's just one of those points where you're like, you just tell yourself there's no other option. Just go, just go, get out of the car and start talking to people. You're not going to, you're not going to get it if you're not talking to anybody. Yeah. Well, I love the idea, you know, that you brought up of not second-guessing yourself and realizing there is no other option. I mean, I look at, you know, one of the other things I like to say is sometimes you just get to a point of no return where you can't turn back. You know, we're, you know, we're the midst of, as I mentioned to you before we hit record, planning our first event. And it was, you know, I think in February, it's like, what the hell have we gotten ourselves into? I mean, this is really in over my head. But what's crazy is that you end up pulling it off and it completely changes. I think the thing that people don't realize is that by the way, that thing that scares the hell out of you, the thing that makes you so uncomfortable, when you lean into it, you actually go past it and suddenly it starts to be normal. You're like, okay. And that all our boundaries and all our limitations are made up, like we create them. And then they cease to exist when we get past them. I mean, you hit two huge things, like, you know, right on the head is you, if you're, if you're afraid of it, hit it, like head on, you know, yeah, you're absolutely right. That's, that was very well said. Thanks. So, you know, one thing I do want to get back to you brought up the idea of all your experiences and how they've tied together, and I do want to start talking about that. Let's get into a few of these other things. I mean, one of the things you also mentioned is that, you know, you have this sort of intersection of design and entrepreneurship, and I really want to talk about the design components. I'm not a designer yet, suddenly in my life, because we work with artists like Sarah Steenland, because I'm inspired by friends like AJ Leon, everything that we do with unmistakable creative, as far as visuals go, is extremely design driven. Like if I look at something, I mean, even our conversations that we have on the air, there's a design element that goes into them, like not a visual design, but there is a design. And you know, you said that as an entrepreneur, you developed an eye for opportunity, and I'm curious what kind of an eye design has trained you to develop, and how that has influenced and shaped all the projects that you work on, and even the, even the actual narrative around the projects that you've worked on. You know, design for me, so when I got introduced to design, I ask a lot of questions naturally. My degree is in philosophy, and I just, I ask a lot of questions, and then when I discovered design, I'm one of these, like, I don't know if you call them weird, but I almost feel like design is my religion in a lot of ways. It's literally the framework for my life. I mean, it's not just making visuals, it's not doing anything. I look at everything through design, like my surroundings, nature, like nature is the absolute best designer we have. I start from that, you know, I look at people like Dieter Roms who, you know, famously designed all of the Brown electronics and things, but you know, he has these, you know, these rules and laws of design. When you hear him talk about those, those are his laws for living design. They're not just his rules for creating electronics, you know what I mean? That's what I do. Like, I literally look through everything through the lens of design, and what that usually means is just saying you're looking at something, and you say, to tie it into your question. When you go to build something, you look at everything, like, I just write everything down, and I try to look at it as a framework, and I say, "This is the thing that needs to exist, so let me break down every single component of this thing that needs to be built, coded, made, and let's just figure out all of the moving parts." And then you get down to the absolute core of the idea, and you build from there. I mean, it's my framework for everything, business, all of it, relationships. It's funny because I have a framework called the Principles of an Unmistakable Standard, which we've turned into a cartoon that some of you guys have seen. I'm very curious. I mean, if somebody is looking to develop their own framework, because I think that, you know, it's easy to think, "My question was going to be, how do we use your framework?" But I think that's actually the wrong question, the real question is, "How do you develop your own frameworks so that we don't perpetuate, you know, pale imitation and mimicry?" You know, I like that idea. You know a good place to start for your own framework is to define the things that make you weird. You know what I mean, like, here's the problem in that business, and we're finally coming out of it, because I think markets got so flooded, we're finally being forced out of it, is someone would start a business and they would look at their competition, right? I mean, that's the first place they went, so they would start to copy people, and in business, you know, from the '80s and '90s into the 2000s, everyone softened their edges. You know, like, no one wanted to really insult anyone or off put anyone or show their weird But the problem is, is everyone rounded those edges, so everyone seemed exactly the same. Like you just said, this mimicry and, you know, businesses didn't have personality. Now I think what you see is people that are kind of like branching out and saying, you know, "I'm going to start a sock company where they're mismatched." You know what I mean, like, you start to see these weird things. You see like Tina Roth Eisenberg, Swiss Miss on Twitter, and her daughter comes home with a really bad temporary tattoo, so she runs off and designs really well, or really well designed tattoos and makes a million dollar business out of it, you know? These weird things are a great place to start for your own personal framework. Find out what makes you weird, and then find out what you want, and then also look at all of the things that you've done in your past. Like what is your skill set, and like what's happened even in like your family life that's made you who you are. And you know, like a personal framework starts with breaking down yourself, breaking down your personality. Like I'm one of these like really strange people where I would do like Myers breaks, right? You do like personality tests, you go to Colby index and you figure out like how do you approach problems, how do you work like best, what environment, you know, like really break down who you are, get a degree in philosophy if you're bored. And then, you know, even do I've done things as weird as like learn how to make my own horoscope chart, just to see if there was something in there that would help me to find who I was and how I needed to approach things. That's just what you have to do. You have to start with yourself and say what's made me me, you know, what's weird about me and why is that so? And then figure out like what fits you and don't copy from other people if you can help it. Well, you know, I think I love the idea of what makes you weird. You know, I always joke like I said, this is what we look, you know, how do we find our guests? We look for what it is about them that makes them weird, which is how we end up as bank robbers and, you know, people who spend in prison as our guests, really popular ones, which by the way, I also said, but don't let that be an excuse for you to go rob a bank or, you know, commit crimes. That's not this idea for how you end up on this show. Yeah, exactly. Yeah, that's amazing. So you know, one thing I want to go back to, you brought up this idea of design as a religion for you, which I love. It may be in fact what I end up titling the interview, but I want to talk about the concept of design as a religion and how that ties into the narrative that brings all the things that you work on together, the apps, a simple cast, pattern school and the great discontent. Does that make any sense as a question? Yeah, no, it totally does. I'm just wondering like, how deep you want me to go because I get, I can get really super nerd. What do you want me to go? All right, well, man, how do I start this? So my journey with design really comes down to like identifying the patterns, right? That's why I called the school patterns is because for me, it's like the most important thing. And if you want to go all the way back to the beginning of the universe, like if you really want to get really, really super nerdy, I, for meditation, a lot of people do yoga or they do different things. And meditation, me, I actually draw geometry, like the actual act of drawing geometry and geometric shapes. Like if you go to my Instagram, you can see a couple of them. Like I approach everything from the smallest little inkling of what it can be. And then I just look at everything with design. Like if you, if you draw these perfect circles and perfect lines, you can see how these patterns make total sense. They're almost mesmerizing when you look at them. So I apply that same thing to apps, books, anything. And what you do is you literally say, okay, what is the value proposition or like, what is the thing that makes this, you know, at its core? Like, for instance, if you have a hot dog stand, right, like you just, I'm rambling and jumping around a little bit. But if you have a hot dog stand, you can take everything back except the hot dog. If you move the hot dog, it's no longer a hot dog stand, right? So anything that's a problem, like building a podcast app or anything, I say, let's take away all the condiments and get it down to exactly what makes it that. It can no longer be a podcasting app if you can't actually like upload the podcast, right? So you get it down to the core idea. And then you build off of that, like you have to start with the smallest possible thing that you have and build on that. And to give you an example of like how that applies is with software, it's a guess when you're building an app or you're doing anything, even a book, it's all a guess. And if you don't build like the smallest possible version of that, some people call it MVP. That's another term that makes me kind of nauseous. But if you don't get it down to that core and introduce it and test it first, you can spend like two, three years building some software that no one's going to use. And I've seen it happen over and over and over again and it's heartbreaking and it's killing like it'll bankrupt somebody. So applying the principles of design, you really, you have to get to the core and you have to say, as you're building this thing, you're building it up, but you're also trying to subtract it, right? So you've heard simplicity is ultimate sophistication from DaVinci, but you know, it's kind of like once you get the core, now it's your job to get it out into the world and then we do the hard work of simplifying it, right? Is it a business? Is it an app? Is it a book? Like you have to do the hard work of simplifying it and John Mayda will tell you the she method, right? You either subtract, you hide or embody elements between things. So what I do is I literally just try to expand it and build it, but at the same time always forcing constraints and trying to cut things down. So that's what nature has done too, you know, when I say design is a religion, if you look at nature, it has to survive and, you know, if you're a lizard and you no longer need your tail to survive in the wild over thousands of years, it disappears. You know what I mean? And nature basically says if it can't survive, then it'll go away. And that's exactly what apps and books and businesses should have like no waste basically. So you're always like really close to the core and you're always questioning everything that you do. And that's that's what a designer does. Spark something uncommon this holiday with just the right gift from uncommon goods. The busy holiday season is here and uncommon goods makes it less stressful with incredible hand-picked gifts for everyone on your list all in one spot. That spark joy, wonder delight, and that it's exactly what I wanted feeling. They scour the globe for original, handmade, absolutely remarkable things. 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Then I want to start specifically talking about each one of them and what their impact does. The common thread is I wish that they existed. For myself. You know what I mean? In my book execute that I wrote with Drew Wilson, that was really at the heart of it. If you're building something that you wish existed and you're building it for yourself, you really can't fail because it was something that you needed. When you start to build a business or an app or write a book, something that you need that's an honest approach to a business. If you go out and you say, here is some weird topping ornament or something, you're like, "I'm just going to get this thing because I know I can make a lot of money from it." That's not going to get you through the hard times of entrepreneurship. People do it and there's nothing wrong with that but from me personally, it kind of starts with that. The common thread is, "Did I need it?" You know what I mean? Then you have a conviction that you can both drive the product and also hold the product too. That makes sense. Yeah. It makes all the sense in the world. It's funny. Somebody asked me, "What was the motivation behind creating your event?" I said, "I created the event that I've been wanting to go to all along." Perfect. Yeah. Let's talk specifics. Let's start talking about the great discontent. I mean, where did that entire concept come from? What's it all about? What are the core themes, the key messages? What is it? You talked about the idea of you wishing something existed. Why did you wish that existed and how was it benefiting other people? Well, the greatest consent, I actually didn't start. Yeah. That was started by Ryan and Tina S. Maker. They were a couple that were living in Michigan. Tina was a social worker. Ryan was a designer. Tina is also an excellent copywriter. She's a great writer. It's something that they wish existed. They wanted an interview. They were going to do a physical magazine, but the internet made it more cost-effective. Now they're doing print. They did a big Kickstarter. It was something that they wish they existed. It had this integrity. It was basically my favorite site on the web. Most people have these star moments when they meet people and stuff like that. When I met Ryan at Brooklyn Beta, which is a big conference in our industry, I just went up to him and I just told him exactly how I felt about it and I'm glad that he did it. Then a friendship ensued and I just stepped in and did the business of it. I made sure that it was funded. For a while, it got a lot of the big projects that the great discontent does now. Just funded and off the ground. What's the underlying theme or comment? With a name like the great discontent, it almost seems to me like there's a social commentary about what's going on in the world because I feel like we really are living in an age of great discontent. I had Sean Acor, the happiness researcher here, and he said job satisfaction or job dissatisfaction is at an all-time high. I am really curious. What is the underlying theme of the great discontent? Is it that we are in an era of great discontent? It's more about risk and creativity to be honest. A lot of times when you build things, so if you're really, really happy, a lot of times unfortunately there's not this catharsis that's involved where you have this pain that you want to fix and you need to design something that will fix it. If you're super happy and you're laying on a beach, you're not exactly motivated to do something amazing. The greatest content I think is a common thread with all the interviews is there came a point where they faced a crossroad. They could either compromise and keep their job or play it safe and they jumped, right? They took that risk. Every interview there was a point where they hit a fork in the road and the reason they're on that site is because they man or womaned up and said, "I've got one life. My insides won't be quiet." It's the greatest content. My insides are screaming to get this work done and to do something that I'm not going to regret later, each one of them took the risk road on the left instead of taking the safe road on the right and that's why they're on that site. Let me ask you this, on that note, when people reach that crossroads and I feel like I reached it about a year ago when I realized I would probably never be able to get hired at a normal job again by admitting that I'd been fired from all of them and that was bit by bit, it led to a lot of other interesting things, even to you being here today, talking to me. There's obviously four years that go into all of that, but the question for me is when you get to those crossroads, you said the road on the left and the road on the right, what separates the people who choose the road on the left from the ones on the right? The ones who choose the one on the right, what separates the risk-takers from the ones who play it safe? I think it differs for everyone, but if I were to give you an answer to that, I would almost say because they had to. There was at some level, they just absolutely had to do it. They weren't going to be able to sleep at night and they knew they were going to hate themselves later because they didn't do what they were passionate about. I think that pain has to be, the level has to be high enough, you know what I mean? Maybe that's where the great discontent really plays into it too, is because that yearning and that necessity to really go out and do something that few are doing, it has to be so strong that it outweighs the safe I'm okay by going home at five o'clock and playing video games. You know what I mean? When you do something on your own, you don't really clock out. I think it just, that desire outweighs comfort. You know, I mean, it just, to me, it boils down to that, like your passion or that gut wrenching, fire, pain, it just outweighs wanting to be comfortable. Hey, everybody, it's Srini. I want to take a quick break to tell you about a new initiative that we've launched called the Unmistakable Salon, our monthly live event series in which you'll be able to interact with one of our former podcast guests and ask them your questions. The very first one is right here in our own backyard, Los Angeles, with our very good friend and creative instigator, Justine Musk, or we're going to talk all about creativity. You can get tickets at unmistakable salon.com and don't worry, I know you don't all live in LA. If you want us to bring the salon to your city, send me an email at Srini@unmistakablemedia.com and now back to the show. If there's one thing that my family and friends know me for, it's being an amazing gift giver. I owe it all to Celebrations Passport from 1800flowers.com, my one-stop shopping site that has amazing gifts for every occasion. With Celebrations Passport, I get free shipping on thousands of amazing gifts and the more gifts I give, the more perks and rewards I earn. To learn more and take your gift giving to the next level, visit 1800flowers.com/acast. Hey I'm Ryan Reynolds, at Mint Mobile we like to do the opposite of what Big Wireless does. They charge you a lot, we charge you a little. So naturally, when they announced they'd be raising their prices due to inflation, we decided to deflate our prices due to not hating you. That's right, we're cutting the price of Mint Unlimited from $30 a month to just $15 a month. Go to try at MintMobile.com/switch $45 up from payment equivalent to $15 per month, new customers on first three month plan only, taxes and fees extra, speeds lower above 40 gigabytes of detail. Hey Prime members, are you tired of ads interfering with your favorite podcasts? Good news! With Amazon Music, you have access to the largest catalog of ad-free top podcasts, included with your Prime membership. To start listening, download the Amazon Music app for free, or go to amazon.com/adfreepodcasts. To catch up on the latest episodes, without the ads, expand the way you work and think with Claude, by anthropic. Whether brainstorming solo or working with a team, Claude is AI built for you. It's perfect for analyzing images and graphs, generating code, processing multiple languages and solving complex problems. Plus, Claude is incredibly secure, trustworthy and reliable, so you can focus on what matters. Curious? Visit claud.ai and see how Claude can elevate your work. Hey there, it's Greenie and Hembo, and we are back and better than ever. Got your answers is for sale, and if you are interested in winning every sports debate you have for the rest of your life, this is the book for you. We take the 100 biggest sports debates and answer them, settle them once and for all. Meanwhile, Hembo, what's your favorite part of the book? 100 sneaky Hembo trivia question. All that and a whole lot more, it's called Got Your Answers. It's available anywhere you get your books right now. Yeah I love that you brought that up. It's the idea of comfort. The fact that you've got this burning desire that outweighs wanting to be comfortable. If there's one thing that I have consistently taken away from any of the work that I've done and any of the people that I've come across, it's often moments of discomfort that end up being the catalyst for their greatest progress or their greatest growth. We had a guy here, you guys will have heard this by now probably, when you're listening to this, the guy who used, he's a math genius who hacked OK Cupid and Wired had a great story on him, but he said one of the things he did was he literally not for monetary reasons, but just because he wanted to create intentional discomfort in his life, he basically packed up all his stuff and storage and moved into his cubicle in his PhD lab at UCLA. It's kind of interesting because he said it was intentional. He didn't have to do that for financial reasons, but he said he knew that something would come from creating intentional discomfort and turned out to be a huge catalyst for growth in his life. Yeah I mean it goes back to why Steve Jobs said stay hungry, stay foolish. You know what I mean? If things are too good and some people, and I think it gets you this too, you know, sometimes when things are too good, I've seen myself kind of like nudge it back to stay motivated. You know what I mean? You know that can't, you know, to extremes it's not going to be healthy, but no, I think there's a lot to be said of that man, I mean you have to stay hungry and you're not hungry if you're fat and you've got everything that you need, you know that it goes back to pain makes the greatest art. You know I learned from Seth Godin like I don't look at art as someone that paints because like Thomas Kincaid, they're great paintings, that's not art, you know what I mean? And I look at someone that's a speaker or someone that, you know, hand makes their own jewelry with a soldering kit, you know, that is art and pain makes the greatest art. Like name me, you know, your favorite songs and I guarantee you they probably weren't positive, happy songs all the time, you know what I mean? It's just something about us being human. Like we like to get that cathartic drive from, you know, discontent. Yeah. Well I think that I love what you said about pain making the greatest art. And you know, I mean I think the interesting thing is, you know, when you have a success of some sort, my, you know, we always say well how do you create the unmistakable standard? It's like okay, make amazing art, set the standard and obliterate that standard over and over again. Until, you know, I mean it's like we, you know, we had a big success with something and the downside of a big success is it scares you because you're like, great, now there's only, there's nowhere to go but down from here. But at the same time, you're like okay, how am I going to totally destroy the standard and reset it again and again and again and I think that that's what, you know, that's what makes somebody like a Steve Jobs, Steve Jobs, right? I mean, even AJ Leon, he says, you know, the number one way to do that is to always exceed people's expectations. Hmm. I like that. Is that the whole under promise over deliver thing? Yeah, I mean, he said every single time exceed their expectations and you know, you look at the work that he does, you know, we, we see that, you know, if you go to a conference that he has in Fargo, every element of it is so handcrafted, it's, it's ridiculous. You look at it and you're like, this is crazy. Yeah. So that's wow. Well, you mentioned Seth and I, you know, I definitely want to talk about this a little bit, I'd love to hear about, you know, your work with Seth and sort of the influence that that had on a lot of the other things that you've done. And then I want to start talking a bit about pattern school and we'll start wrapping things up here. Okay. Yeah. You know, I, I've, I've been a huge fan of Seth's for years. I mean, I want to say back to like 1999 or something when he, he wrote permission marketing. The thing that I always loved about Seth is you could see he was a business mind. But if you look at his, you know, like chron, chronological order of his books, you can see that even though he was a business guy, his books became more and more about art, more and more about, you know, like personal art and standing out and being honest. I mean, speaking of weird earlier, he has a book called We Are Weird, you know, like he sees these things and he's, he's kind of a futurist and he is a really good philosopher. And you know, I, I think even in my industry and web design and things like that, I think there are a lot of industries that don't realize how much of a gem Seth is. And when you work with him, you see it even more because, you know, he was an inspiration for, for patterns as much as design was, you know, I, we, we would pose ideas to him. And it was so fun to watch because he would literally listen to your idea. And if he, if he didn't think it had any weight, he would just dismiss it because we don't, nobody has time for that, right? Like, it was, it's just a really bad idea. Let's just kind of like put that to the side. If it's a decent idea and it triggers something in his head, he does this really cool thing where he like, he puts his hands on the back of that beautiful bald head. He has, you know, and he, he leans back in his chair and he looks up. And the reason I kind of like said, you know, this has to be called patterns is because you could literally see him take that idea and run it across all of the patterns that he's experienced. Every one of his friends that's ever had a business, any business he had, any process he had, the people that he's known, the great businesses that have been built, you could just see him like cross checking it across all of those things for validity. And it's an amazing thing to watch. Like, okay, so maybe not everyone cares to watch that. But for people like us, it really, it's a great thing because he just, he's got an ability to point out value and he's got an ability to point out validity that you only get from doing what he's done in his life. I love that. Yeah. It was great. So talk to me about how that's made its way into, into what you do. I mean, talk to us. I mean, what is patterns? And then, you know, how has that whole process, which, I mean, that sounds brilliant. And I think that's something that it's funny because I can, I can see elements of that and coming four years later, somebody asked me, how has 400 interviews influenced your worldview? And I said, well, imagine all the patterns between all these people starting to finally connect in your brain. It's a very, very strange thing, but I don't think it would have happened without four years of doing this. No. And you know, that's, that's the beautiful thing that I'm trying to almost tap in or, or hack, I guess, for lack of a better term. But, you know, one of the first things that you do when you come to patterns is I basically ask everyone to come in and bring me the three people that you admire the most. And a lot of times we even use the great discontent since, because it's so story driven, I mean, you mentioned that you love stories. I say, bring me the three projects or the three people that inspire you the most or that you, you want to pattern your own life after the most. And we literally just break down like what made them successful, what made them who they are, their back stories. And we, we, we treat a person just like you would treat a business. You just break it down all the way down to its elements. And what that does is it just shows people that A, it starts with an idea and it's a passion. B, it's work. You know what I mean? It didn't happen overnight and overnight successes are always seven years in the making. And it also just shows them like the different things. It shows them a framework without having to like kind of go through those four years. Like you said, it says, Hey, this person, you know, I don't know, was from a broken home or, you know, they, they lost a parent or, you know, they were put on the street. They were an orphan. You know, whatever it was that made them who they are, when you go through that exercise, you can see it in yourself. Like, that's what we do, right? When we read something or we go shopping or whatever, we're always projecting whatever it is onto ourselves. And that's exactly what it is. You learn to dissect things and that patterns and in design, if you can't break things down first, you have a shaky foundation. So that's what we do. I mean, that's, that's what I learned. You just, you bring in the people that you admire most and just break them down. And that's how you learn how to break yourself down. Mm hmm. So let me answer this. There's a lot, a lot more questions around this. I love this idea of breaking yourself down and all of that. So I want to talk about that. I mean, what was the, what was the major motivation for, for creating this? And is this a challenge to our current modern form of education, which clearly has led to a lot of problems? In a lot of ways it is, yeah. You know, again, my motivation for it was I wish it existed. Mm hmm. You know, in a lot of ways, I'm trying to do what the ancient philosophers did. You know, with their academies, they sat around, they asked a lot of questions. You know, I don't think people are asking enough questions. And I don't think that our current education system is supporting art for what it needs to be. Like you do not learn, you learn techniques and you go to school and you learn humanities, which is one thing that people like need to remember. Let's don't kill education. We need our humanities. But as far as like your art, your personal art, finding yourself, like you're not trained to find yourself in school. You're actually trained to die to self and be a cog in a system. I mean, you are not, you only get an A when you do what you're told. And in life, if you want to support your art, the only way you get an A in that is, you know, is if you just completely throw us to throw a stick in the spoke of everything. You know what I mean? Like you have to, you have to break things to be successful to find things that are unique and that's not what we're trained to do. Yeah. Well, you hit one of my hot buttons. I mean, I can go on an education. We could literally have a two-hour discussion about, you know, the fails of modern education. I mean, I always say I've been over-educated to a fault. I like that. You know, and it's true. I mean, and I guess that the challenge, of course, is part of, I think the reason projects like yours exist is because it's not happening from within a system that is so ingrained into a way of doing things and so brainwashed into their own mindsets that I think it's going to be a very long time before we can, I think for them to see the reality of what's coming based on the system they've set up. The only way it's going to happen is when they see how severe the consequences have become. Yeah. I couldn't agree more. And that's really unfortunate. I mean, so you brought up this idea of breaking down yourself and I love the idea of patterns. I mean, can we, can you talk about how we might apply that entire framework in our lives and then tie that into creating our personal art? Man, how can we start this? It was a long, great question. I've been known to do that to people. Yeah, no, it's amazing. I mean, it, you know, again, as a person, like breaking yourself down and figuring out who you are, you can actually define like what your art is through that process. I mean, you can just, you can kind of see like what you honestly like, not what you think is going to be, you know, not what's going to make money or, you know, not what you think your parents want you to do. You know, you're not what's going to be socially acceptable. You know, here at patterns, it's almost like we want you to come up with something so crazy that it's not socially acceptable because the whole point here is Kevin Kelly's a thousand true fans. Like when you come to patterns, my main focus and even in my life now is just serving a thousand people really, really well. I'm not trying to build anything that's the next Twitter. I'm not trying to build an empire. I don't really care about legacy, like none of that matters to me. I want to find a thousand people that are just absolutely die hard passionate about what I do. And that to me is gold in an individual's journey to support their art. A thousand people. That's all you need. And Kevin Kelly said that he was like, if you have a thousand people that buy everything you make, you'll never need for anything again. And you know, when you're breaking things down and you want to apply it to your art, like first find your art, like find it, find what would get you up in the morning, find out who you are and do the hard work of finding out who you are. Like that's harder. It sounds simple, but that's actually really hard for people to admit, you know what I mean? Like going through breaking yourself down and objectively saying like, who am I? Like, what do I feel like my purpose is? Like what's this existential dilemma that I'm having about myself? Like that's more painful for people than they admit. Yeah. And that's, that's where you need to start, I think. Well, I guess that that's what Seth would call emotional labor, right? Yes, exactly. It's yeah, that, that honestly is, is much harder. I love that you brought up not what will make money, not what your parents will approve of and to really even look at what is so crazy that it may not be socially approved of. I really, I really appreciate that perspective because I think the three things that you mentioned are the, the first, that's, that those are sort of our first line of defense or our first filters through which we run any, any inkling that we have of that, that internal desire to create, it's almost like we have this instinct to go right to those filters because that's what we've been taught to do our entire lives. Yeah. It's our, it's our safety mechanism. You know, some people call it the lizard boy, Seth called it the lizard brain rate a book about it. And they're like, that's exactly what it is. It's a, it's a, it's a safety mechanism is like when you have this idea and you're like, oh, this is great. I love it. The first thing you do is protect yourself from it. It's like we have to get through that, that thinking and that training because, you know, the, the key to being successful at what you do is try to be as weird as you possibly can without being illegal. You know what I mean? Like there's a thousand people, no matter what you do, I don't, I don't care if you decided that you wanted to do nothing but make the best blue sock you could possibly make. That's a weird thing to do. But I guarantee you, there are a thousand people out there that if you showed them the process that you went through to make this blue sock, the care that you put into this one blue sock, there'd be a thousand people out there that would buy pairs and pairs and pairs of these socks from you. You know what I mean? It's like, I hope that makes sense. I hope it's not too ridiculous, but like literally like, yeah, whatever makes you weird, like that is what's going to make you successful. You just have to find a way to, you know, package it, I guess. Yeah, I guess that, that really, you know, I love the idea of packaging because I think that really brings us full circle. You know, I said, whatever makes you weird is what makes you successful. And I think that the really sort of me, for me, that the key element of that, if you kind of dissect it and strip it down, is there's a story behind it, right? And we're, you know, what brought you and I together was something about the stories that you guys share really intrigued me and that's, that's, you know, one of the things I like to do is story is sort of the driving force behind the unmistakable creative. And even with the blue sock, right, I think that what appeals to people about something like that, as crazy as an example as that is, is not the sock itself, but the story that leads to the creation of it. In a lot of ways, yeah, yeah, absolutely. And you know, everything is a story in one way or another. And why stories are so powerful is because a lot of times when we buy something, that's our justification to ourselves to buy it. We have very little needs in, you know, but I mean, I live in the States. I know you do too. Like in the States, there's, there are definitely people that are in need, you know, but if we have time to do this podcast right now, we have very little needs that aren't met. So after that, it becomes wants and it becomes the stories that we tell ourselves and the things that we buy are a reflection of the story that we're telling ourselves, even though no one's really looking at us like we think they are, if that makes sense, that makes total sense. So two final questions and we'll wrap things up. Okay. You know, one is around the story that we tell ourselves, you know, in some ways for some people that story serves them, for others, it sabotages them. And I'm curious how we turn it into one that actually serves us. That is a really good question. And again, it's different for everyone. I think some people, I think some people have thoughts and passions and it can be a very destructive thing or a very constructive thing, you know what I mean? And, you know, I think turning those stories into something positive, I mean, it all comes down to attitude, I think, you know what I mean? If you're, even if you're like a skeptical person and around your friends, your note is the person that's like Debbie Downer, like a skeptic constantly and always knocking things down, you could just sit around all day and just knock people down. It's not going to be a very, not a very lucrative thing and not a very fulfilling thing. But if you're that kind of person, become a critic, you know what I mean? That's the story you tell. Put a positive spin on it, you know what I mean? Like, I keep going back to this, but like finding out who you are and building from that. You know, there are so many things in this world and so many passions that we have that there's a narrative constantly going in our minds. And if we have taken the time to really dissect and be honest about that narrative, I think we can put a positive spin on it. If not, I think it becomes, you know, destructive behavior and a lot of it comes down, especially in entrepreneurship, things like that. Being able to write your own story, like the story either happens to you or you make the story happen. The people in the great discontent, they sat there one day and they became proactive rather than reactive. And to me, that is where the story changes. Does that make sense? Yeah, yeah, absolutely. Well, so one final question around sort of the art, I mean, you know, our show is called The Unmistakable Creative and I always say, you know, what separates the guests, you know, what makes somebody a guest on our show is that they are unmistakable. So, you know, based on all the things that you've experienced, you know, the patterns that you've seen through all the work that you've done. And you know, when we're creating art, I mean, what is it that makes somebody or something in this world today unmistakable? Doing, being honest with themselves and doing their work, you know, like, I think what makes someone unmistakable is being themselves. We're all very unique. We all have so many like different desires, interests, things like that. And when you see someone like doing their work and you really see someone in their element, that element of pure passion and doing what they love and whatever is an extension of them as a person, that's unmistakable because it's unique to them. To me, that is kind of like the Holy Grail. If you can define your art and it's completely like authentic and true to who you are and you can find a way to sustain yourself from that, that's the Holy Grail to me. I love it. Well, Josh, this has been really, really amazing as I expected it would be and I can't thank you enough for taking the time to join us and share some of your insights with our listeners here at Unmistakable Creative. It was an absolute honor. Thank you for having me. And for those of you guys listening, we'll wrap the show with that. You've been listening to the Unmistakable Creative podcast, visit our website at unmistakablecreative.com and get access to over 400 interviews in our archives. Expand the way you work and think with Claude by Anthropic. Whether brainstorming solo or working with the team, Claude is AI built for you. It's perfect for analyzing images and graphs, generating code, processing multiple languages and solving complex problems. Plus, Claude is incredibly secure, trustworthy, and reliable so you can focus on what matters. Curious? Visit claud.ai and see how Claude can elevate your work. Hey there, it's Greenie and HEMBO and we are back and better than ever. Got your answers is for sale and if you are interested in winning every sports debate you have for the rest of your life, this is the book for you. We take the 100 biggest sports debates and answer them, settle them once and for all. Meanwhile, HEMBO, what's your favorite part of the book? 100 sneaky HEMBO trivia question. All that and a whole lot more, it's called Got Your Answers. It's available anywhere you get your books right now. Sprouts Farmers Market, we're all about fresh, healthy, and delicious. Step into our bulk department to scoop up as much as you like from hundreds of bins filled with wholesome grains and limited-time goodies. Visit your neighborhood Sprouts Farmers Market today where flavor fills every scoop. Have you ever felt a twinge of worry about AI taking over your job or diluting your creativity? Well, what if you could turn that fear into create a fuel? We've just published an amazing new ebook called The Four Keys to Success in an AI world and this is more than just a guide. It's a deep exploration into the human skills that AI can't touch. The skills that are essential for standing out and thriving, no matter how much technology evolved. We're talking about real differentiators here like creativity, emotional intelligence, critical thinking, and much more. Inside, you'll find actionable insights and strategies to develop these skills, whether you're a creative person, a business person, or just simply someone who loves personal development. This isn't a story about tech taking over, it's a story of human creativity thriving alongside AI. Picture this AI as your creative co-pilot not just as a tool, but a collaborator that enhances your unique human skills. The Four Keys ebook will show you exactly how to do that and view AI in a new way that empowers you instead of overshadows you. Transform your creative potential today. Head over to unmistakablecreative.com/fourkeys. Use the number four K-E-Y-S that's unmistakablecreative.com/fourkeys and download your free copy. Thank you. You [BLANK_AUDIO]

To say that Josh Long is an entrepreneur who keeps himself busy is an understatement. He’s the creator of the to-do list app Cheddar, the podcasting service Simplecast, and oversees sponsorship at the Great Discontent. In this interview he talks to me about the underlying themes and threads of his life’s work and how to identify yours. 


  • Josh’s exposure to entrepreneurship at a very early age
  • Why entrepreneurship is all about creating value
  • The innate entrepreneurial spirit within all of us 
  • Why our low points teach us so much about ourselves
  • Learning to put things in perspective when you’re challenged
  • Why facing your fears head on is the best way to deal with them
  • Looking at your whole life through the lens of design 
  • Finding the things that make you weird to develop your own frameworks
  • The concept of design as a religion 
  • Stripping things down to a core idea 
  • Why should build and create things that you wish existed 
  • Josh’s role in getting projects and funded for The Great Discontent
  • What separates the risk takers from the ones who play it safe
  • A look at the work that Josh did with Seth Godin
  • The cathartic drive that comes from pain 
  • Leveraging the patterns of successful people you admire
  • The difference between getting A’s in life 
  • Why Josh is only focused on serving 1000 people 
  • The role that the story plays in everything you create

Josh Long is a designer and writer with a degree in philosophy and three books under his belt: Execute, Jenius, and Design Evolution. He co-hosts the Happy Monday podcast with Sarah Parmenter, is building the to-do app Cheddar, coordinates sponsorships for The Great Discontent, and is the co-founder of Simplecast.

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