The Learning Leader Show With Ryan Hawk - 659: Derek Sivers - Not Waiting for Permission, Hell Yeah or No, Leadership Lessons From The Dancing Guy, & Why The Standard Pace is for Chumps

Episode Date: October 26, 2025

Go to www.LearningLeader.com for full show notes This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical... Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver. My Guest: Derek Sivers is the founder of CD Baby and author of "Hell Yeah or No" and "Useful Not True." He shared how he graduated from Cal Berkeley in two years instead of four because the "standard pace for chumps" - a lesson that shaped his entire career of institutional skepticism and unconventional thinking. From creating viral shipping emails to understanding why explorers make bad leaders, Derek shares why being busy means being out of control, how your first thought is an obstacle to your best work, and why you can't predict what the world will want from you until you try everything and listen closely to what it's telling you. Notes: No Speed Limit – Most things are paced so the slowest person can keep up. If you're driven and motivated, you can go so much faster than the standard pace. I graduated from Berkeley in two years by learning four semesters of harmony in one hour. "The standard pace is for chumps. You can do so much better than that." Question the Standard Process – When someone says you must go through usual channels or something will take a certain time, assume there's probably a hack. Develop institutional skepticism - there's usually a better way than how most people do it. Create Opportunities, Don't Wait for Them – You don't have to wait until a company is hiring. If you can see how to benefit them, walk in and show them what you can do for free first. Alan Tepper made Warner Brothers more money than anyone that year by just showing up with a plan. Make Everything Valuable to Others – The starving artist spends all their time on work valuable to them but not to others. Use money as a neutral measure - if you can make money with your art, it ensures what you're doing is valuable to other people. "It's almost impossible to predict what the world will want from you... Keep yourself out there and listen closely to what the world is telling you it wants from you." Stand Out by Being Different – Don't imitate what everyone else is doing. I wrote a silly shipping email in 10 minutes that became one of the most viral emails ever mentioned in business books. Ask yourself constantly: What has nobody done before? The First Follower Creates the Movement – We focus on the shirtless dancing guy, but the first follower is what made everything happen. Until then, people kept their distance from the freak. If you find someone doing something great, follow them and show others how to follow. Every Sentence Must Matter – My books are 90-100 pages, but start as 1,000-page rough drafts. I spend 1-2 years full-time chopping every sentence that doesn't absolutely need to be there. "I'm not gonna put a single sentence out into the world that doesn't need to be there." Make every word count - eliminate everything that doesn't add value. Hell Yeah or No is Context-Dependent – This tool is for when you're overwhelmed with options and need to raise the bar. Straight out of college, say yes to everything because opportunities are like lottery tickets. Once something rewards you, then say no to other things and double down. Busy Means Out of Control – "Busy to me implies out of control. You're busy if you've let other people shove shit into your schedule." Leave space instead of filling it - that time to think is what creates valuable insights others don't have time to develop. Your First Thought is an Obstacle – Don't honor the thought that came first. In brainstorming, acknowledge the first idea, then keep going - don't stop at two or three. Even silly ideas can seed great ones you'd never reach without that stepping stone. All Beliefs Are a Myth – People worshiped Zeus for centuries; now we call it mythology. But we say our own beliefs are true while others' are superstitions. I expected China to be awful from American news, but found it wonderful - question what you've been told. Use Prejudice as Your Compass – If you notice you're prejudiced against something, that's exactly what you should explore. Burning Man sounds awful to me; therefore, I should probably go. Steer into your biases to overcome them and gain new perspectives. Explorers Make Terrible Leaders – Explorers try everything and change direction constantly, which frustrates teams. Leaders go in a straight line to a clear destination, unwavering in mission even if the path changes. I loved changing my mind, which made me a bad leader until I learned the difference. Set projects with clear missions, even if you're personally exploring other things. Try Everything Until the World Says Yes – I had a booking agency, a record label, a recording studio, and my own music - all failures. Then, a side project to help friends (CD Baby) took off. You can't predict what the world wants from you, so try many things and listen closely to what it's telling you. Reflection  What "standard pace" are you accepting in your business or career that you could actually accelerate if you questioned it? Where have you assumed something has to take a certain amount of time just because that's how it's always been done? Are you spending time on work that's valuable to you but not to others? How could you test whether what you're creating actually solves problems people are willing to pay for? Are you acting more like an explorer or a leader right now? If you're constantly changing direction, how could you set clearer missions for your projects while keeping your personal explorations separate? Resources & References Derek's Content: Derek's website and blog  "Leadership Lessons from Dancing Guy" (First Follower) TED Talk - Derek Sivers  "No Speed Limit" essay  Former Episodes Referenced #647 - Tim Ferriss - Chasing Your Curiosity #562 - Nikki Glaser -  The Creative Process of a Comedian  #644 - Blaine Anderson - Confidence, Curiosity, Connection  Episode Timestamps 02:20 Early Life Lessons from Kimo Williams 05:21 Corporate Lessons and Unconventional Paths 09:10 The Power of Adding Value 13:57 Viral TED Talk: Leadership Lessons from the Dancing Guy 22:03 The 'Hell Yeah or No' Philosophy 27:29 The CD Baby Experience 28:02 Starting an Online Record Store 29:10 Creating a Unique Shipping Notice 30:01 The Viral Impact of Creativity 32:53 The Importance of Regular Writing 35:17 Questioning Assumptions and Beliefs 36:23 Exploring New Perspectives 40:41 The Explorer vs. The Leader 48:21 Advice for Aspiring Leaders Resources: Read: The Score That Matters Read: The Pursuit of Excellence Read: Welcome to Management To Follow me on X: @RyanHawk12

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Starting point is 00:00:00 This episode is brought to you by Insight Global. Insight Global is a staffing and professional services company that builds world-class technical teams for clients around the globe. If you need help with your applications, infrastructure, or data layer, Insight Global's team of technical experts can build custom or manage services to deliver the outcomes you desire. Getting the most out of your technology can be tough, but growing your business. business with the right technical solutions can be magic.
Starting point is 00:00:35 Visit Insightglobal.com slash learning leader. That's Insightglobal.com slash learning leader today to learn more. Welcome to the Learning Leader show presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Go to learning leader.com for show notes of this and all podcast episodes. go to learning leader.com. Now on to the night's featured leader.
Starting point is 00:01:08 So great. Derek Sivers, the entrepreneur who built CD Baby from nothing into the largest seller of independent music online. Then he sold it for $22 million and gave the money away. You might know Derek from his viral TED Talk called How to Start a Movement about leadership lessons from a dancing guy. Or from his books, including anything you want, Hell yeah or no and useful, not true. During our conversation, we discussed why the standard pace is for chumps
Starting point is 00:01:42 and how you can go faster at whatever it is you're doing. And Derek shares how he put together his viral TED Talk and how he handled having Bill Gates, Tony Robbins, and the founders of Google sitting in the front row staring at him while he gave, by the way, a three-minute TED Talk. TED Talk that earned him a standing ovation. And then we closed talking about the difference between explorers and leaders. Ladies and gentlemen, please enjoy my conversation with Derek Sivers.
Starting point is 00:02:18 So you're 17 years old and you're about to start your first year at Berkeley School of Music. And you meet this guy, tell me if I'm pronouncing his name wrong, Kimo Williams. That's right. And you have a conversation with him. What happened next? It was about two months before I was set to go to Berkeley College of Music. And I mentioned to him that I was going. And he said, oh, really?
Starting point is 00:02:45 He said, I used to teach there. He said, I have an idea. He said, come by my studio tomorrow morning at 9 a.m. And I think I can help you graduate Berkeley in two years because it's a four-year college. And I showed up at 9 a.m., which surprised him because he said that he often says this to people that shows some mild interest, and nobody ever shows up at 9 a.m. But there I was, at his door at 9 a.m., ready to go.
Starting point is 00:03:13 And that impressed him. And then he sat down with this intense pace and taught me four semesters of harmony classes in an hour, because he just went really quick and intense, and I was quick enough to keep up with it, And what I lacked, he said, learn this over the next week, and we met a week later, and he taught me four semesters of Berkeley College of Music's arranging classes in two hours. And we met maybe four times total, and that was enough for him to teach me essentially two years of required courses at Berkeley. because his main point was most things are paced so that the slowest person can keep up.
Starting point is 00:04:08 But if you're driven, if you are motivated enough, you can go so much faster than the standard pace. He said the standard pace is for chumps. You can do so much better than that. You can graduate a four-year university in two years. And I did. man what do you draw i mean 17 years old what a great life lesson how have you taken from those moments with chemo to say wait a second i can go way faster this pace that's for chumps right the regular speeds for chumps what have you taken from that that has helped you later on in life
Starting point is 00:04:49 institutional skepticism when someone says you have to go through the usual channels and file the forms as such. I think, not necessarily. And when someone says that'll take this long or you need to do this first, I think there's probably a hack. That's probably the standard way that most people do it, but there's probably a better way. Derek, let's say somebody who works in a corporate America or just a corporate job in the world. And they're ambitious and growth focused for the right reasons, right? They want to provide for their family.
Starting point is 00:05:34 They want to enjoy their work. They want to build a career. I know this is slightly different from the way that you've looked at it. But I think that's a lot of people and I still love to do whatever I can to try to help them. What could they take from that story to say, maybe there's a different way. Maybe there's a better way to do this thing than just try to climb the regular. their corporate ladder like everybody else is trying to do. Here's a real example.
Starting point is 00:06:01 After I graduated Berkeley College of Music, I got a job at Warner Music in New York City. Even the way I got the job, quick aside, was because a visiting speaker from New York City from a different music company was visiting Berkeley College of Music. And as he walked into the classroom to begin speaking, I heard him say to the teacher, are we starting now?
Starting point is 00:06:25 And the teacher said, yeah. And he said, I thought we were going to eat first. He said, oh, man, I haven't eaten lunch. I thought we were going to eat first. So I quickly, while the class was getting settled, I dashed out to the pay phone, and I called Supreme's pizza, whose phone number I had memorized,
Starting point is 00:06:40 and I had them deliver three pizzas to room number 314. And so about 30 minutes into his talk, the pizzas come. And I paid the guy and brought the pizzas up to the speaker. who looked at me and said, all right, good one, I owe you one. And we kept in touch for the next few years. He's the one that got me the job at Warner Brothers because he heard them mention in passing
Starting point is 00:07:06 that they were hiring a new guy to run the tape room, and he said, I've got just the guy for you. And he called me in Boston and said, I got you a job in New York City if you can start on Monday. And that's how I got the job. I never had to interview or anything. His recommendation alone just got me the job. So that's not even the real story I'm telling, though.
Starting point is 00:07:29 That's just another example of how there's always a different way than the usual channels, right? Be proactive, take action, like, get it done, be valuable. That's something I... We'll talk about that in a second, but yeah, I want you to finish this story. So while I'm working at Warner Brothers, there is one empty little office that one day wasn't empty. And there was a guy there named Alan Teper who just showed up and said, hey, I'm Alan. I've started working here. And I said, oh, what are you doing?
Starting point is 00:07:59 He said, well, I don't officially work here yet, but I told them to just give me a desk, and I'm going to make the company a lot of money. I said, how? He said, because I used to be in advertising. And I saw that Warner Brothers is not proactively pushing their music catalog to advertising agencies. So I said, just give me a desk, give me a phone. You don't have to pay me. Let me show you what I can do. Alan Tepper, later that year, made more money for the company than anybody had in years.
Starting point is 00:08:34 Officially, they did hire him eventually, but the company was not hiring. He walked in saying, I know how I can make you more money. Just let me show you. And that's it. I love this story because you don't have to wait. until a company's hiring. If you can get a little inside into an industry or a company and see how you can benefit them, you don't have to wait for them to hire anyone or say that they're hiring. You can just walk in and show them what you can do for them and say, you don't even have to pay me.
Starting point is 00:09:04 Let me show you. And I've seen this work in action. I think it's a great approach. I love that. One of the things you also did was give a talk to the Berkeley students, and it was titled Six Things I Wish I knew the Day I Started Berkeley. And I think the one that I pulled out from that six that I want you to expand on is very similar to what Alan Teper did. And that is, when done, be valuable. You're right. When you leave here, you said to them, head to the business aisle of the bookstore and start reading a book a week about entrepreneurial thinking, things like marketing. Make sure you're making money.
Starting point is 00:09:41 That's a way to continue on and make sure you're doing something to add. value to others. Sometimes you'll think like, oh, I'm just going to be good or I'm going to make this art or going to do this thing. And you said, no, there's a part of it that you've got to create a business. You've got to add value to other people. You have to make money. And I think to be excellent at whatever you're doing, constantly thinking about how am I adding value to others is a good way to approach it. How have you used that in your life? Well, first I got to give a little context that probably people listening to this podcast say, well, yeah, duh, making money, I know, especially on the internet, it feels like that's all everyone's talking about, it's how to make money.
Starting point is 00:10:26 But at a music school, there's this tendency to go too deep into chord voicings and timbre and the structure of your second verse as it leads into your pre-chorus and whatnot. diving deep into the mechanics of music, which is important. It's super important, which is why elsewhere in that talk I say, shut out all distractions, stop reading all media, dive deep into these things that I just mentioned. But then, yes, when you're out of here, shift your focus and find a way to make that valuable to others.
Starting point is 00:11:10 Because we've all heard the phrase, starving artist. The essence of the starving artist is someone who is spending all of their time on work that's valuable to them, but not valuable to others, meaning they might be pouring hundreds of hours into some expression of their feelings of the meta-universe we all live in, but other people can't relate to it. And so nobody wants it. Nobody wants it. Nobody. interested, but that person is spending all of their time on this thing that nobody else is interested in. That's a problem. It's a very common problem for artists, writers, musicians. So the point was keep in touch with the objective measure of value we call money, which is so
Starting point is 00:12:02 loaded with baggage, but if you think of it just as a neutral measure of value and try to find ways to make money with your art, it's a way of making sure that what you're doing is valuable to other people, not just to you. Yes, I think the key learning for anybody, whether you view yourself as an artist or not, is what am I doing to add value to the lives of the people around me? I learned this in sports early in my life, Derek, where if I didn't give our team the best chance to win, I played quarterback, so only one guy gets to play, then they're going to play the other guy. And that happened to me in college. right, where the coaches looked me dead in the eyes and said, that guy gives us a better chance to win than you do.
Starting point is 00:12:45 He's adding more value to our team than you do. That's a great lesson to learn, man, especially when you're 19 years old, as you learned valuable lessons at that age and your formative years, because that's kind of how the world works. Like if you add value to people's lives and help them and put them in a better position, you're probably going to have a lot of work. And if you don't, you've got to find a way to do it. I think. I don't know. What do you think?
Starting point is 00:13:09 I see you thinking right now. Yeah, well, I'm thinking about when you had the dating coach on, how a hard thing with dating is to how to see yourself through other people's eyes. And it's kind of the same thing, isn't it? To get out of yourself and stop thinking of the intrinsic internal value of what you're doing to you and think of it as how valuable it is to someone else. Yes. I think that's something to be regularly thinking about. That shows high levels of emotional intelligence, high levels of self-awareness,
Starting point is 00:13:45 supreme levels of intelligence. There's a million different things to get to with your story, Derek. I love it. We've talked about it in the last time, but one of the things you did is I love how you put together one of the many viral things you've done, which the title, if you just search leadership lessons from the dancing guy, maybe it'll also say in parentheses, first follower.
Starting point is 00:14:07 I'm curious. What were you thinking when you put that talk together with the video? And then maybe you can describe it too for those who haven't seen it yet. Sure. 2009, I was living in New York City. And there was a video, maybe it was Reddit, maybe it was Dig. I don't know what it was at the time that just somebody showed this video of a guy dancing alone. There was this shirtless guy dancing kind of like tripping balls, as we'd say, dancing at this music festival.
Starting point is 00:14:38 just all alone. And people are just casually sitting there looking at the funny shirtless dancing guy. And at one point, somebody jumps up to imitate him and starts doing all the same moves he's doing. And because one guy imitates him, a second one jumps in right away. And now the two of them are imitating the shirtless guy.
Starting point is 00:14:59 And then right away, three, four, five, six, seven, eight, 20 people all jump in to do the same thing because that first one had the common confidence to do it. And I had just finished reading two books. One was Tribes by Seth Godin, and one was The Tipping Point by Malcolm Gladwell. And both of these books describe how actions start a movement. And so while I was watching this video of the dancing guy, I thought, this is kind of like a visual metaphor of
Starting point is 00:15:38 of what Seth Godin's tribes and Malcolm Gladwell's tipping point are talking about. So I just blogged it. At the time I was blogging almost every day, so just that day I posted a blog post showing that video saying, isn't this kind of like making a movement? I said, but notice how we focus on the shirtless dancing guy, but actually it was the first follower, that first guy that jumped up. That's what made everything else happen. Until then it was people keeping their distance from the freak.
Starting point is 00:16:11 But the first person jumped up and started imitating him, that let the second person do it, and then there was no reason not to, because other people had already begun. And I thought it was really interesting then how the first and second followers were the ones that really showed everyone else how to follow. And then of course you think of the metaphors in real life, like if you find some lone a nut doing something great. It might be a mad scientist in their computer basement somewhere, but if you find somebody doing something great, one of the best things you could do is to follow that person and show other people how to follow. And then when you put it together,
Starting point is 00:16:52 it was a TED talk, right? Yeah, it was a TED talk. Oh yeah, okay, so sorry. So yeah, I just blogged it, and that was it. But then a few months later, the TED conference put out a call saying, were taking submissions for new talks. So I just submitted that, and they said yes. And then began the day that I thought my heart would explode. I was there at the big mainstage TED conference. I mean, like Al Gore, Sergei Bryn, Larry Page, Tony Robbins, all of these VIPs. Bill Gates is sitting right there.
Starting point is 00:17:28 All of them in the front row looking at me like, all right, anonymous speech. I've never heard of, impressed me. So I got up on stage and delivered that talk to that room. And it was terrifying. Was it? I mean, you didn't, you made it look easy. Well, thank you. But what was terrifying is it was like memorizing a four-minute-long monologue.
Starting point is 00:17:52 Like if you think of being in a school play or something like that, you have to memorize a monologue. Because if I forgot a single sentence, the whole thing gets out of whack with the video. with the video. I have to memorize word for word, this four minute long speech about leadership in order for it to match up exactly with the video of the dancing guy. And to do that while my heart was racing was so scary. I thought it was going to have a heart attack. But got off stage and one of the coolest moments of my life is the musician Peter Gabriel, whose music I loved for years, saw me, interrupted his content.
Starting point is 00:18:31 conversation with someone else and ran up to me to shake my hand saying it was the best thing he had seen. And then later that day, Tony Robbins and a bunch of other people tweeted it. And I was very proud. Wow. How many times did you practice it? Oh, God. At least 100. Really? Yeah. Over and over and over and over again. I would just call up friends and say, come on, let me do this one more time with you on the phone. Okay? Hit play on the video. I'm going to do this with my eyes closed now. Let's see how I do. Wow. I think that's the inspiring part to me, Derek. It means it is possible. We can do it. Now, you're a really smart dude, but it's the practice. I had Nikki Glazer, the stand-up comedian on this podcast, and to hear her talk about the number of times she has repped her material before any of us see it, it's very similar to what you're saying. And so to me, that is inspiring. Now, it's a ton of work. And you've got to be super dedicated to excellence and wanting it to be great. You probably, you wrote the blog, you knew the material well enough where you could have just kind of rift on it. And it probably would have been decent.
Starting point is 00:19:39 But instead, you're like, I want this thing to be excellent. I want it to be as good as it can possibly be. So I'm going to practice it with my eyes because I'm going to practice it so many times that I can't forget. I think there's a lot to take from that. It started this idea of wanting every sentence to matter. So anybody listening here, if you check out any of my books, you'll see that they're all very short, like my three-minute TED talk. They offered me 18 minutes. I said, no, I think I can do this in under three minutes. So same thing with my books. My books are 90 pages, 100 pages. They're meant to be read in an hour.
Starting point is 00:20:21 But the reason is the rough draft is 1,000 pages. And then I will literally spend full-time for one or two years to squeeze it and squeeze it and squeeze it and squeeze it and chop every sentence that doesn't absolutely positively need to be there. And in the end, what's left is this itty-bitty little book that's almost like poetry because it's so succinct. But the idea is I'm not going to put a single sentence out into the world that doesn't need to be there. I think a lot of us as leaders could learn from that. Think about your next quarterly business review, town hall meeting, Monday morning meeting, thinking about pruning that thing down, making it so that every word that comes out of
Starting point is 00:21:10 your mouth has to and nothing more. It's kind of like Robert Green. Do not speak unless you can improve upon the silence. But thinking about that for everything you say and do, we'd have a lot better meetings, man. Hell yeah. That's one of the things you said, speaking of that.
Starting point is 00:21:28 So a little bit of the background, I asked you to come back on because when I was talking with Tim Ferriss, one of your good buddies, he talked about you. He brought up quotes of yours. We talked about you off air to, you know,
Starting point is 00:21:39 all this stuff. And so I sent that to you like, hey, you know, I thought you might want to check this out because we talked about you a little bit. And I'd love to have you back on. And you said basically like you're going to go on
Starting point is 00:21:48 a sabbatical from doing podcasts, but hell yeah, let's do it. And you have this thing that has not been copied, I think, by tons of people of basically, hell yeah, or no. So either I'm going to go do it 100%, give everything I got, or it's going to be zero. I'm not going to do it. Can you go deeper on that hell yeah or no?
Starting point is 00:22:05 That's also the title of the book. But that mentality of how you approach projects, how you approach life in general. We've all felt the pain from saying yes to too many things so that you're spread too thin. And I did this like everyone else. At a certain point, I realized that if I were to say no to almost everything, what it would give me is the space and the time so that when that occasional thing comes up that I'm actually really excited about, well, now I can just fucking smash it. I can throw myself into it entirely and do something like the hundred closed-eye practices
Starting point is 00:22:48 of a speech or an entire year editing a rough draft down to 100 pages. I have the time to do something like that because I've said no to almost everything else. So it's about leaving space instead of filling your space. It's leaving the space so that when that opportunity comes up, you can say, yes, absolutely, and I can start right now and I can throw myself into the space. this entirely because I said no to almost everything else. What's the response to that book and to that mentality from people like? I'm more curious about the negatives because yes, I'm glad you brought that up.
Starting point is 00:23:33 I personally had borrowed this from you, stolen it from you, share it with like leaders I work with who have the calendars that you've probably seen them back to back to back to back. That's every day. That's like five. Sometimes they meet on Sundays like and I'm like, dude, you got to. Are these all hell yeses? Like all of them? Every single one of those, every one of them.
Starting point is 00:23:52 Well, you know, they're pretty important, man. I got to do this stuff. I have a lot of people who report to me. And I'm like, wow, I don't know. I don't know. So I'm just curious to the response you get to that. Well, two things. For one, it's cute when people contact me out of the blue and say,
Starting point is 00:24:08 well, I'm sure you're very busy, but, and I say, no, I'm not busy. Because busy to me implies out of control. Yeah. You're busy. if you've let other people shove shit into your schedule. If you leave space, then to me it leaves time to think. Part of the reason people buy my books and want to hear my thoughts is because I'm this weirdo that spends a lot of time thinking.
Starting point is 00:24:41 I don't spend a lot of time doing. I don't have a full schedule. And because of that, I'm able to sit around and think, for six hours about the impact of language on our approach to life or something like that, that most people don't have the time to do, but I do because I sold my company and retired and I spend my time thinking. So if you tune into my thoughts, ideally you're going to hear something you haven't heard before because I just spend more time thinking about the kind of stuff that most people don't
Starting point is 00:25:13 have the time to think about. That's why you outsource it to me. Okay, so that's one hell yeah or no aspect. But where I thought where you were going with this when you said the negatives are that I get emails from people that are straight out of college saying, hey, I saw this hell yeah or no book of yours and I'm applying this to everything now. I'm not taking any jobs unless it's really a hell yeah. And I say, no, no, no, no, no, no, look, it's one tool in the toolbox. You don't use the monkey wrench as a hammer. You don't use the monkey wrench as a toothpick.
Starting point is 00:25:51 It's a monkey wrench. It's meant for a certain situation. So hell yeah or no is a tool for when you're overwhelmed with options and it's time to raise the bar all the way. It's the wrong strategy to be using straight out of college when you'd be smarter to say yes to everything because opportunities are like lottery tickets at that point. The more, the better, sleep less, work 21 hours a day, say yes to nine jobs at once, if that's what it takes to open those lottery tickets.
Starting point is 00:26:26 And then once something's rewarding you and pays off, then you say no to these other things, you double your efforts and raise the bar all the way. But hell yeah or no is a specific tool for a specific situation. Okay. I like that clarification because I think, yes, sometimes people just hear the part they want here. And then, yeah, you're 23. And you're like, I don't know. I'm like, dude, the job you get when you're 23 for most of us, most, you know, I don't mind. Cubicle, pounding the phones, 60 cold calls a day. Sometimes you go 0 for 60 in a sales job. Great job, though. It was hard.
Starting point is 00:27:01 I didn't love it most days. But I grew to get good at it. And I grew to develop skills that have helped me for the rest of my life. If you would have said like, well, is that a hell yeah? Or do you love that job? You're like, no. Are you kidding me? When I got done with college, that's I thought I was going to be doing. Of course not. But I'm so grateful for that experience and that opportunity that it's made me better and all other things. Now, I want to shift Eric to, I think this is a leadership thing. You may view it as a creativity thing. So when you were running CD Baby, so this is your company that you already mentioned that you have sold. When somebody makes a purchase of something, you usually get like a canned email. Like, hey, you ordered these socks
Starting point is 00:27:42 and they're going to get there in three days from Amazon or whatever. And you had that same thing initially when people would order a CD, but you changed it. So can you tell me how you changed the, hey, you bought this CD email? I love that you said socks. And we'll come back to that in a minute. Okay. But imagine this. Yeah, it was 1998.
Starting point is 00:28:05 I had just started my little online record store in my living room. There's no employees, just me. A little tiny website I made myself that had 100 musicians selling their music through me. And yeah, the default shipping notice was the default. It said your order has been shipped. It's on its way. Thank you. And I just looked at that and thought, I can do better than that.
Starting point is 00:28:32 Like why be normal? I think this is a lesson that every musician learns is you don't want to write a solidly. that somebody else has written. You want to write something that nobody's done before. Say the lyric that's never been said before. And so same in business. Don't just do the same thing that everybody else is doing. Ask yourself constantly, what has nobody done before?
Starting point is 00:28:58 What would add something to the universe and make the world a better place? Surprise somebody. Make eyebrows go up, not down. So in 10 minutes, In 10 minutes, I wrote this silly little thing saying, your CD has been placed onto a satin pillow and a hush fell across the crowd as we lit a candle
Starting point is 00:29:22 and put your CD into a gold-lined mailer and onto our private jet, which is on its way to you in Dayton, Ohio. On this day, Friday, August 13th, we hope you had a good time shopping at CD-Baby. We're all exhausted, and your picture is now. now on the wall as customer of the year, we can't wait to hear from you again, etc. And that's it.
Starting point is 00:29:48 I wrote it in 10 minutes. It was a bit of silliness. It became the default shipping notice. I just said it to automatically send that to everyone that bought something. But because it was so weird and different, people started forwarding it to their friends, and then blogging about it and then talking about it. And Seth Godin had a chapter about it, I think. in the Purple Cow or a mention of it somewhere in Purple Cow.
Starting point is 00:30:13 And other business books mentioned that particular email as one of the most viral shipping confirmation emails ever. And then just two years ago, here in Wellington, New Zealand, I heard about compression socks because I was flying a lot. And somebody said, you should look into having compression socks if you're sitting on planes a lot. I thought, I don't know what compression socks are. But I went online, typed New Zealand.
Starting point is 00:30:40 and compression socks, found a seller, ordered two pairs. The next day, I got an email that said, your socks have been placed onto a satin pillow. No way. A hush fell across the crowd as we lit a candle. And your socks are now on our private jet on their way to the year, and your pictures on our wall as customer of the year. And I said, wait a second.
Starting point is 00:31:05 Are you doing this because you saw my name in the shipping notice? the woman running the shop said, what? Sorry, no, I don't, what are you talking about? I said, I wrote that 25 years ago. I wrote that. And yeah, she had no idea. She just copied it out of a book. Oh my God. That is awesome. Again, though, you're thinking differently and anybody can do this. Anybody can think differently about how you do it. And it's hard to quantify what that did for your business, but the virality of it, how creative it was, caused it to spread, and then ultimately had to have had an impact on your business. I had to. Oh, yeah. Like literally hundreds of customers that I knew about, that mentioned it, said, I heard of you from this blog post about your shipping
Starting point is 00:31:55 confirmation. I heard of you because of this book mentioned your shipping confirmation. So a lot of people heard of me because of that silly email I wrote in 10 minutes. But you're right. The bigger deal is not looking to the outside world to see what we can imitate, but to look at what's been done already and see how you can try something different. It's harder, but I bet part of why this happened is because you were writing a lot. You were getting your thoughts out of your head onto the page regularly. You published a lot of them, maybe some of them you didn't. But I think that is the ultimate tool for clarity.
Starting point is 00:32:34 it's the ultimate tool for teaching. And I think teaching is the ultimate tool for learning. This show is called The Learning Leader Show. I'm very focused and fascinated by people who are chasing down near curiosity with great rigor and trying to learn to grow to get better and hopefully positively impact the world and other people. Can you talk more about the importance of being a regular writer, of getting those thoughts out of your head onto the page? For me, it's healthy doubt, skepticism.
Starting point is 00:33:09 It's questioning the defaults. If you jot down your thoughts, ideally you occasionally question them. If you say, that person wronged me, ideally then you add a question mark. That person wronged me? Maybe. Maybe not. How can I look at that situation through another light? We need to adopt AI.
Starting point is 00:33:41 Let's add a question mark. We need to adopt AI? Everybody says it's the greatest thing. Is it necessary? Do we have to do this? It gives you time to question assumptions and to not just stick with your first impression impression. Our first thought is an obstacle. We should not be honoring the thought that came to us first.
Starting point is 00:34:09 Like a brainstorming session, you need to acknowledge that that's the first idea. Okay, what else? Give me another one. And then don't stop at two. Don't stop at three. Make yourself come up with a bunch of different perspectives. Sometimes the silly ones can help seed a really great idea that you never would have thought of if you didn't have the silly step in between. But all of this is taking the time to go past your first thought,
Starting point is 00:34:46 past that obstacle onto the more interesting perspectives just by taking the time to think through it. Whether that's in writing or just make sure that just in case somebody is avert, or allergic to writing. It can also just be talking into a voice recorder. It could be talking to your cat or talking to a friend. It could be journaling into a paper notebook. It could be typing into a text file.
Starting point is 00:35:11 Just some way of collecting your thoughts and just giving yourself the time to reflect and think. Well, I think part of it, this comes from your book, Useful, Not True, is that we just make these assumptions that our beliefs are true. And I like this part. You said for hundreds of years, people worshipped Zeus and Athena and others. And now, this was crazy. Now we call that mythology. Those are myths.
Starting point is 00:35:38 But now when it comes to our beliefs, no, no, no, those are just true. Other people's beliefs, those are superstitions or those are myths. But my beliefs, they're true. That part really spoke to me because I think as a learning leader, as someone who's chasing down my curiosity really, really hard, I'm always questioning it like maybe there's a better way. Maybe there's something I don't know. Maybe what I currently think is wrong. And if I find that, I get pumped.
Starting point is 00:36:06 I'm happy. Like I found a better way. This is great. So bringing in this kind of like, hey, people used to like worship these gods. I think that's why it's worth it for us to question our own beliefs because that could be our beliefs. You know, I don't know. Yeah. What do you think?
Starting point is 00:36:23 I went to China for my first time last year. only because my boy had watched Kung Fu Panda enough that for his school holiday, he asked if we could please go to China. So I thought as part of his education, I should take him to China. But I expected it to be awful. You hear American news stories about this awful place. It's always spun negative with the dystopian guy. and the oppressed people and the ghost towns from the stupid real estate developers that built skyscrapers that nobody wanted, you only hear the negative. But if you go there, it's wonderful. The cities are amazing. The people are happy. Just forget every other measure.
Starting point is 00:37:19 Just sit and observe all the smiles you see in the middle of the major cities. People are happy. They're thriving. They're productive. The cities are clean and the people are entrepreneurial and driven and optimistic about the future. And it's amazing. So I've been back four times in the past year. More than anything, really surprised how pleasant this place is that I've always been told as part of the evil empire. And then you think about how many other things we've been warned against are not actually bad. It's just that maybe the two governments or even the two corporations have something against each other.
Starting point is 00:38:07 And so they tell us to agree with them. But there's so many different perspectives to be had out there. And it's worth it to go experience them, to go try to gain your own perspective and approach it with curiosity instead of judgment, right? There's like this spectrum. Yes.
Starting point is 00:38:26 So now I even use this as a compass that if I noticed I'm prejudiced against something, that makes me want to go into it to find out more about it. So let's give a non-political example. To me, Burning Man sounds awful. Me too. It sounds like the last place I'd want to be in a desert for a week with no food and water except what I bring in myself and everybody's on drinking. rugs and it's all crazy. It sounds terrible. Therefore, I should probably go. I thought,
Starting point is 00:39:03 what's another insane clown posse? I don't know their music. I've heard maybe one song once, but I think the fans of insane clown posse paint their face black and white and they call themselves jugaboos or something like that. And then once a year, somewhere in Indiana, I think, they have the annual Jugaboo festival where all the fans of insane clown posse get together. for this crazy festival. And somebody passed a little YouTube clip of it, and I thought, that sounds awful. I should go because I'm full of prejudice against it.
Starting point is 00:39:38 Therefore, I should steer into it. It's kind of like the Lincoln quote, right? I don't like that man. I must get to know him better. I never heard that. Really? That's Abraham Lincoln? I think so.
Starting point is 00:39:50 From what I read on the internet, that might not be true. But from what I've read, yeah, I don't like that man. I must get to know him better. And I think that is kind of a broader way of, you know, what's funny is like usually when you do meet those people. At times, I've seen people on the internet where maybe I cringe a little bit. And then I'll be at a conference or something and we're both there. I'm like, good dude.
Starting point is 00:40:08 He's a good guy. Yeah. He was great. He was great. We had fun. Maybe he'd shared a meal or something. It's like, yeah, good guy. There's one thing too, Derek, about and useful, not true, about leadership and exploring.
Starting point is 00:40:18 And I wanted to touch on this because you've openly talked about you not being a good leader. And not many people do that, especially on a leadership podcast where they admit like, no, I'm not really that good of a leader. Yet you create this business and it grows and you sell it and make a bunch of money and now you do whatever you want. And you have for a while now. But can you talk to me out the difference between explorers and leaders? Yeah.
Starting point is 00:40:42 I learned this lesson in hindsight. Hard lesson learned. While I was running my company, I was actually a pretty bad leader. as proven by how frustrated my employees were that I loved changing my mind. And I loved changing my mind for the reasons that we've talked about right here, introspection, reflection, considering other approaches. I'm always hoping to change my mind. That's one of my favorite things to do in life, is to change my mind.
Starting point is 00:41:17 It's great when I find a new perspective that changes my mind. But my employees were so frustrated by this that only years later in hindsight, looking back, I can see now why I was such a bad leader. It's because let's use the archetype of the 1800s explorer from England that gets on a boat for six months to go to the unexplored jungle, machete in hand with a pith helmet, a few, workers carrying the baggage, but for the most part, it's an explorer going into uncharted lands to hack around and see what's there, to go where nobody else has gone, maybe go up that hill,
Starting point is 00:42:07 there's nothing up that hill. Let's go into this inlet. There's nothing in that inlet. What about this inlet? Oh my God, there's a gorgeous bay. Look at this amazing Paradise Bay in this inlet. Nobody's ever been here before. This is a great harbor. This would be a great port. So then the explorer sends a message back to the queen saying, I've found this great harbor. And then the queen appoints a leader. Now this is very different than the explorer who's trying everything. A leader is someone that goes in a straight line that says,
Starting point is 00:42:43 we're going to this harbor, we're going to set up a city here. These are the benefits. This is how you will gain by doing this. Follow me. And the leader goes in a straight line. And if halfway there, somebody were to say to the leader, hey, what do you think about going to a different direction instead? The leader would say, shut up.
Starting point is 00:43:07 Lock that man in the jail. We're going straight ahead. I'm not changing my mind. And the leader goes in a straight line to the destination with a clear mission undeterred. That's a great leader because that person is easy to follow. It's clear where we're going. Even if you're in the back of the crowd
Starting point is 00:43:30 and you can't hear what the leader is saying, it's easy to see where we're going, what we're doing. And in hindsight, I see then the difference between the explorer and the leader and how I was just an explorer, which made me a really bad leader. But next time, if I were to do it again and I wanted people to follow me,
Starting point is 00:43:49 I would pause my explorations, declare a certain harbor to be the destination, and I would set that project as having a clear unwavering mission. Even if I personally might go explore some other things, I would declare this project to have a clear mission straight line easy to follow. Is that distinction too black and white? In the real world, leadership is a little bit more messy than that. I think it's a little bit more gray, whereas you can have some exploration and some set the vision and the objectives and let's go. No deviations. Follow me. We're going. But the great ones, I feel like, also are curious enough and humble enough to listen to people on their team, even if those people work for them when they say boss or leader, dude, this.
Starting point is 00:44:49 part of the plan is actually not right. Like, this part needs to be tweaked a little bit. And a good leader say, hold on, let me think about that. Ah, you're right. We still have the same vision, right? We're still heading in the same direction. But yeah, what you're telling me, I missed on that part. Let me adjust.
Starting point is 00:45:06 Right. So, like, there seems like there is a little bit of gray in there, whereas the Explorer versus Leader thing seems more black and white. Two thoughts. Okay. Black and white examples are, made intentionally purified for the sake of clarification so that we can see what we're talking about.
Starting point is 00:45:26 Good call. But even in that metaphor of the leader going on the boat to the harbor across the world somewhere, yeah, you're right that ideally if there was a storm in the way, a good leader would not go through the storm. You'd go around the storm. The destination hasn't changed, but maybe the path changed. Or in that metaphor, you're right.
Starting point is 00:45:46 If somebody looked at the map and said, Hey, boss, by the way, I love how you said boss leader, dude. Hey boss leader, dude. We could actually get there better or faster if we were to take this alternate route, which you had not planned, but it actually gets us to the destination better. I think anybody listening to this, yeah, you get the metaphor for your own situation. But it's good to realize that some of us have started businesses for our own satisfaction of in exploring.
Starting point is 00:46:20 Yeah. And you should be wary. If you notice that you were more of an explorer, but you're calling yourself a leader, you might need to take a different approach. Or keep your explorations personal and keep your business in a straight line, even if your personal interests are keeping you astray.
Starting point is 00:46:37 What would you do? Would you get help from other great leaders? Would you ask them questions? Would you read their books? Which you read tons of books, I know. Like, what would be your approach to be a better leader next time? I would just define it as a project, kind of like how we incorporate a company. You set up an LLC and you say, for this project, this project has this goal, clearly stated, straight line, this is what this project's doing.
Starting point is 00:47:03 Follow me to this destination that this project is out to pursue. We're aiming to discover this technology. We're aiming to solve this problem. And just set it as a clear defined project so that then even if you hand that off to a different leader, that person also knows the clear aims of this. It's easier to communicate. Your marketing's easier. You're able to more clearly see exactly what this is, what it solves, how it will help, where it's going. Yeah, leave that as an individual project that goes in a straight line.
Starting point is 00:47:38 I think my dad was so, and he still talks about this, being so good at being vividly, clear in the message and narrating the journey and making sure we knew how we played a role and helping us get to whatever that thing is. And we're like, okay, I got it. Now, I can go execute on this thing. That's the job of leader, though. It's like the rally the people and make sure you're clear enough as a communicator that they know where we're going, why we're going that way and how you specifically help us achieve this big thing. Then you can get on board. Derek, I got one more question, man, before we run. This is awesome. I appreciate you. you getting up early over there in New Zealand. It's kind of cool that this technology exists
Starting point is 00:48:17 that I'm here in Ohio. You're in New Zealand. We can talk like we're just hanging out. But let's say you're meeting with one of those. We mentioned the early college grad when hell yes or no might not always work for them. But let's say they're like, hey man, I want to leave a positive dent in the world. I really do like you have. But I'm not really sure yet how or what I'm going to do. What are some general pieces of life slash career advice you give to that person? If you see yourself from the outside, like we talked about earlier with a starving artist, it's almost impossible to predict what the world will want from you.
Starting point is 00:48:59 You can read the stories of successful people that maybe moved to California to take a job insurance but then suddenly randomly got a job as an actor because somebody saw them in a restaurant and saw they fit the part of a haggard army general and they took that job and it ended up being their biggest success. You never know what the world wants from you. So therefore, it helps to try lots of things and not get too hung up on one thing that you're guessing is going to be your contribution to the world, but might not be. I'm going to use a music metaphor here. In my years in the music business, I'd occasionally run across somebody who had
Starting point is 00:49:48 written a song, one particular song that meant the world to them, and they kept trying to push that song onto everybody. But people just didn't like that song. But it was frustrating for them because they said, no, this is the song. This song has great value. But listen again, maybe you'll like it the second time. and they were trying to push this thing that people didn't want. And then I see that in business too.
Starting point is 00:50:14 Somebody that has an idea that they're just sure that the world is going to want this, but the world doesn't want that. And it's unwise of you to keep persistently pushing without changing. You need to persistently keep trying variations until you find the thing that the world clearly tells you, yes, we want this from you. That's what happened when I started CD Baby. I had done many, many, many things. I had a booking agency, a record label, a recording studio.
Starting point is 00:50:50 I had my own music. None of it went well. It was just failure, failure, failure, failure. And then this silly, whimsical little thing I did on the side to help a few friends. That's the thing that took off and could feel such a difference. Suddenly, all the doors that had been locked
Starting point is 00:51:09 were suddenly opened to me. Everybody that had been booting me out, suddenly was inviting me in. And I never could have predicted that it was that one thing that would have been the big success. So do lots of stuff, try many things, keep yourself out there, and listen closely to what the world is telling you,
Starting point is 00:51:33 it wants from you. Yeah, you never know, but you got to like keep chopping, like keep going, keep trying to add value to other people's lives. And like eventually it seems like things find a way of working themselves out. Derek, part of the reason I love your approach just in general to life is your dedication to excellence, is your willingness to do a lot of the hard work that nobody sees to edit down these massive books down to small ones where there is, literally not a single wasted word. I even read the transcripts that you've published of podcasts you've been on, including this podcast. And even the transcripts are edited beautifully. I know I don't speak as well as what it looks like in those transcripts. And so I'm thinking,
Starting point is 00:52:20 was I really that good? I'm like, no, obviously I wasn't. Derek edits them because he cares about even the transcripts that he puts out. So like this dedication to excellence, these high standards, that is inspiring to me. And so I just want to make sure you know that. I appreciate that. And I would love to continue our dialogue as we both progress, man. Thanks, Ryan. I really appreciate it.
Starting point is 00:52:42 So good. It is the end of the podcast club. Thank you for being a member of the end of the podcast club. If you are, send me a note, Ryan at learningleader.com. Let me know what you learned from this great conversation with Derek Sivers. A few takeaways from my notes. The standard pace. is for chumps.
Starting point is 00:53:06 Most things are paced so the slowest person can keep up. You don't have to go that slow. In fact, you probably shouldn't. Think of ways you can increase your pace, much like Derek did by graduating from college in two years instead of four. The standard pace is for chumps. Next, we should question our beliefs.
Starting point is 00:53:30 For hundreds of years, people worshipped Zeus, Athena and others. Now, we call that mythology. They're myths. But when it comes to our own beliefs, those no, no, those are just true. Only others' beliefs are myths and or superstitions. We should question our beliefs too. We should get excited when we find that something we had originally thought to be true
Starting point is 00:53:55 turns out not to be. I love that. And then the shipping email he wrote for his customers at CD Baby. Initially, he was like everybody else. When the CD was actually shipped, the first note was just normal. Hey, your order has shipped today. Please let us know if it doesn't arrive. Thank you for your business.
Starting point is 00:54:12 Then he changed it to a variety of fun, creative things. One of them being, your CD has been gently taken from our CD baby shelves with sterilized, contamination-free gloves, and placed onto a satin pillow. The whole point is to be yourself, be different. You don't have to do it like others do. In fact, you probably shouldn't be creative. Be funny. Enjoy it.
Starting point is 00:54:35 Create something that might make somebody forward it to their friends or write about it in a book or want to spread a cool story. We all can do that. Once again, I want to say thank you so much for continuing to spread the message and telling a friend or two. Hey, you should listen to this episode of The Learning Leader Show with Derek Severus. I think he'll help you become a more effective leader. and because you continue to do that, and you also go to Spotify and Apple Podcasts and write a thoughtful review and rate the show,
Starting point is 00:55:06 hopefully five stars, and subscribe to it doing all of that. Helps me continue to do what I love on a daily basis, and for that I will forever be grateful. Thank you so, so much. Talking soon, can't wait.

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