# The Surprising Benefits of Working Weird and Awful Jobs (ft. Derek Sivers)

An episode of [SOLVED with Mark Manson](https://invisiblenetwork.ai/podcast/1247526593), 28 Feb 2024, 1 h 07 min.

Audio: https://claritaspod.com/measure/pscrb.fm/rss/p/mgln.ai/e/441/dts.podtrac.com/redirect.mp3/episode.flightcast.com/xn1htpzhi6tn7dpgmlplswki.mp3

Successful people talk a lot about what made them successful. But they're rarely asked about all the things that went wrong. What about all of the things that failed? Or all the times they got fired? Embarrassed themselves? Spent time in jobs that were just plain weird or awful? No one asks this stuff. Until now of course. In this episode, I talk to my friend Derek Sivers about the weird and awful jobs that eventually led him to become a millionaire. From circus ringleader to founder of one the most successful music start-ups of our time, this guy has a story to tell. Derek Sivers is the author of four books, founder of CD Baby which he sold for $22 million (then gave most of it away), and just an all-around badass. CHAPTERS Chapters • 00:00:00 Introduction: The Jobs That Didn't Work Out • 00:01:44 The Pig Show That Changed Everything • 00:04:53 The Professional Pest: Getting Paid to Annoy College Students • 00:08:50 Mark's Investment Banking Disaster • 00:13:50 The Metaphorical Time Zone and Corporate Reality • 00:17:48 Class Reunions and Working for Dreams, Not Money • 00:19:46 Telemarketing and the Art of Not Being Yourself • 00:24:30 Identity, Authenticity, and Cultural Differences • 00:26:42 Mark's Three-Week Career as a Bouncer • 00:30:07 The Value of Weird Jobs and Empathy • 00:30:52 Comfort as a Trap and Keeping Your Baseline Low • 00:42:22 Home as a Place With No Obstacles • 00:34:14 Quitting the Marathon: When Goals Don't Serve You • 00:35:25 The Landmark Forum and Life Having No Inherent Meaning • 00:38:10 Investing in Skills Over Paychecks • 00:31:51 The Horizon Principle: Why Hardship Doesn't Feel Hard • 00:39:42 What Cities Whisper: New York, Luxury, and Success • 00:48:12 Being Around Greatness: Geography and Ambition • 00:44:22 How Derek Became a Japanese Rock Star • 00:55:46 Alan Tepper and Creating Your Own Job • 00:58:39 Mark's Career as a Men's Dating Coach • 01:01:40 Transactional Thinking and Missing Father Figures • 01:03:59 The Teacher Learns More Than the Student • 01:06:34 Wrap-Up: Failed Jobs That Made Us Who We Are ⇨ Sign up for my newsletter, Your Next Breakthrough. It will help make you a less awful person: https://markmanson.net/breakthrough ⇨ Get clarity on what actually matters. Try Purpose, Mark's AI mentor app that learns your patterns, challenges your blind spots, and helps you take action. Get started at https://bit.ly/4w46FMH FOLLOW MARK Mark's IG: https://www.instagram.com/markmanson Solved IG: https://www.instagram.com/solvedpodcast/ Twitter: https://x.com/markmanson LinkedIn: https://www.linkedin.com/in/markmanson/ YouTube: https://www.youtube.com/@IAmMarkManson

## Transcript

[0:00] How does a circus clown end up becoming a multi-millionaire? How does a bouncer get fired from a bar and then later get paid to go drink in that same bar? You know, when people do podcasts with all these ultra-successful people, it's always about their greatest successes. What did they do right? What were their best decisions? How did they overcome the obstacles? How did they figure out that genius chess move? Then you're free to check the king.
[0:25] Nobody asked them about all the things that went wrong. All of the jobs and companies that failed, the times they got fired, and of course, all of the times they embarrassed themselves in the career paths that didn't work. So I decided to sit down with my old friend, Derek Sivers, and do just that. See, it just so happens that Derek actually is the circus clown who ended up a multimillionaire. He was the ringleader of a circus in his 20s before he went on to found CD Baby, one of the most successful music startups of the last 30 years.
[0:54] Now, between the two of us, Derek and I have had some pretty weird and terrible jobs. Telemarketing, investment banking, Japanese rock band. Derek got paid to harass college students while wearing a black Lycra suit. I'm not making that up. You'll hear all about it. And of course, I got paid to take guys to bars and help them pick up girls. These are all the hard-earned life lessons of the career paths that didn't work out for us.
[1:18] but inevitably made us who we are today. This is how all of our unexpected failures helped us learn and become successful. And of course, these are also some of the most entertaining and ridiculous stories from our lives. Enjoy. The podcast that's saving the world, one fewer fuck at a time. It's the subtle art of not giving a fuck podcast with your host, Mark Manson.
[1:44] A good friend, the wisest people I know, Derek Sivers. I don't know if you have a place that you would like to start, but I'm curious, how did you get involved with the circus? A very tiny tale and a very tiny lesson. I was 17 years old at Berklee College of Music
[1:59] an aspiring musician. And I was in a band where a bass player, the bass player in the band was more successful. He was playing in like 10 bands around town, so he had an agent. And he said, hey, my agent said, there's a gig, somebody wants to pay $75 for a guitarist to play at a pig show.
[2:18] I don't want it. You want the gig? I said, fuck yeah. 75 bucks. My first paying gig. All right. So it was like a $50 round trip bus ticket up to Burlington, Vermont from Boston to get a $75 gig where I walk around for like four hours playing guitar at a pig show. No direction. Just, yeah, show up there. Somebody will pick you up at the bus station. Just go play music.
[2:42] And and I'll pay you 75 bucks. So, yeah, I got home, got the 75 bucks. But then the the agent called me and said, yeah, I got the report from the pig show in Burlington. You did a really good job. So listen, I've got this circus. Wait, wait, wait. The musician just quit. All right. Yeah. Yeah. What is a pig show?
[3:01] Like, you know, the awards, most beautiful pig. Show your pigs. Weigh the pig. Guess the weight of the pig. I don't remember. I was just there playing music. Okay. All right. I just, you know, I strapped on my acoustic guitar and I just kind of walked around strumming guitar and singing some songs. I don't know why.
[3:22] Ignoring the pigs around you. Yeah. I don't really remember it that much. But I remember what happened after because it was because that one little $75 pig show gig that the agent called me and said, hey, I run this circus. We do about three to four shows a week. The previous musician just quit. We didn't need a musician or basically you've kind of got the gig, but let me just come out and let me see what you can do.
[3:47] So I got the gig. And for the next 10 years of my life, I did two to four shows a week as the ringleader MC of the circus from the age of 18 to 28. And I only stopped doing it when CD Baby took over my life. But yeah, for 10 years of my life, every single weekend, I was up touring the Northeast, performing in front of audiences as a ringleader MC of a circus.
[4:09] It was because I said yes to the $75 pig show gig. So to me, the lesson learned was when you're early in your career, you just say yes to everything. Because you never know what stupid little thing is going to lead to a bigger thing. It just opens doors everywhere to just say yes to everything. Early in your career, you should say yes to almost everything. And then later in your career, once you're established, you should say no to almost everything. Yeah.
[4:38] And I found that transition of knowing when to switch over to be very, very difficult. It's almost like retraining your brain over a long period of time. I'm curious, what was your favorite circus act? Oh, um, I,
[4:53] I wonder if the website is still up, but I think you can go to professionalpests.com. And if you see a picture of somebody in a black shadow fabric, that's me in there. It was one of the bits during the show was like a little like dance routine where this woman would like come out of the bags and she would be inside like five layers of bags and keep shedding the bags to this piece of music. And so...
[5:19] Whenever we do a show, it'd be like a one-hour show, a 90-minute show, and then we'd take a one-hour break and come back. So during the one-hour break, I would take her black fabric lycra bag and get inside it and just go running around the audience bugging people. And I had so much fun doing that, just like annoying people inside this black shadow, that later I found out that universities have a student and activities entertainment budget. And so I decided to market myself as the professional pests where...
[5:47] where they would pay me $1,500 to come to the campus and run around and bother people for a few hours. Because it was funny, and I had so much fun doing it. I would put on elbow pads and knee pads inside so I could do really crazy shit, like crawl around on the floor and jump up and scare people. You got paid $1,500 to go fuck with college kids for a day? Yeah, for three hours inside a black shadow bag. Dude, how...
[6:14] That's the best gig in the world. Yeah. I forgot. You know, it's funny. I forgot that as like a gig that I did. Yeah. When I was thinking about my jobs, I was thinking about employers. Yeah. But now this is a thing I created myself. Yeah. So I looked at the university college scene and.
[6:33] Mostly because I wanted to be a successful musician, and this was a way that you could get your band a bunch of gigs. But you had to pay a certain amount of money just to get into the scene. It's called NACA, National Association of Campus Activities. And you had to pay a fee just to be a member. So once you're in as a member, you can submit unlimited acts. So I thought, well, I'm joining this for my band's sake.
[6:55] But as long as I'm here, hey, I guess I could take this thing I do with the circus and I can market that, call it professional pests. But sure enough, that took off, right? Because there are tons of bands, tons of guys with guitars, but there was only one professional pest. It was a really unique act. You're filling a niche. Yeah.
[7:14] Yeah, I conquered that niche. Guys running around in a black shadow bag annoying people for money. And it was so much fun. So yeah, college would just do it unannounced. I was what was called a roaming artist where no need for a stage, no need to announce me, just suddenly on campus that day
[7:32] was like a guy inside a costume. So you'd be kind of in the cafeteria queue getting your food and suddenly there's like a guy, you know, stealing the milk off your tray or crawling between your legs or whatever. And it was just a blast. And then other people would enjoy watching people get scared by it. And some girls would get really freaked out and scared and then some guys would get really aggressive. And it was just funny for people to watch from a distance, like everybody's reaction to the shadow.
[7:58] And this wasn't announced. You would just show up and... Yeah, the college would just pay me $1,500 to come out to Connecticut or upstate New York or whatever and show up and do this for a few hours. My God, man. I'm in the wrong business.
[8:12] Eric, we should bring the pest business back, man. I love it. We're both retired. Come on. I've seen on the internet, people have marketed you as a circus clown. Were you ever a clown? That's my fault. I mean, I did sometimes put on face paint with the circus, but really I was the ringleader MC. Yeah.
[8:32] Uh, if people call me clown, it's my fault. Cause I, uh, I included that in my bio at some point for the fun of it. Oh, gotcha. Okay. We're going to market the shit out of this episode. Derek, Derek, the circus clown. The professional pest.
[8:50] Okay, I'm dying to hear your stockbroker experience. First of all, disclaimer to everybody listening to this. It's really funny, Derek. I often get emails from people asking for career advice. And I always tell them, I'm like, you're asking the guy who has never held down a real job for a career.
[9:06] like more than a couple months. So, you know, take this all with a grain of salt. But this is how naive I was. In college, I got really into poker in college. And I bought all the books and I studied everything. This is back when you could play online in the States. And it was like 2006, 2007. For a college kid, I won quite a bit of money probably probably.
[9:25] between five and $10,000. And all of the other guys that took poker seriously, like my poker buddies, basically, they were all going into finance, obviously. And in my head, I'm like, well, I'm good with math. I like numbers.
[9:41] poker is fun. Like all my friends are going into finance. I should go into finance too. They make a lot of money. Why not? So I actually got a job at an investment bank as like a low level grunt. And I'll never forget first day of training. And I remember looking at my watch when it was like 10, 15 and thinking to myself, how long do I have to stay here before it doesn't look bad if I quit?
[10:05] man, you're like only two hours in on your first day and you're already thinking about quitting. This is a really bad sign. It was very much a lesson in corporate culture. I was a naive 23, 24 year old. I didn't understand why things were the way they were. So to give you an example, I was basically a data monkey. So I'm a,
[10:26] Our job was literally just fill in spreadsheets, collect data, organize things in the charts, you know, fill out forms, shit like that. And I remember after a couple of weeks, I started thinking to myself, I'm like, man, there's like so much of this stuff is publicly available. Like, why don't we just automate this? And I knew a little bit of like basic programming. I was like, I bet I could program like a macro, like scrape some of these things.
[10:50] some public databases and just like automatically fill all this stuff in. And so I got super excited about it. And I remember I went to my boss and I like, I sat down to like, Hey, I got this idea. See this thing that I, me and like the other 20 people on my team are doing all day, every day. I bet we could automate like 80% of this with a simple program. And I started to explain it to him and his eyes just glazed over and, and he like interrupted me and he was like, go back to your desk and get the work.
[11:20] Like he looked at me like I was lazy, you know, like, like this was like I was trying to talk my way out of something. And I remember just being absolutely stunned that not only was my brilliant idea of automation shot down, but that he was he seemed almost offended that I would like suggest such a thing. Now that I'm older and I have a little bit more perspective and I understand what.
[11:42] why very, very large companies operate the way they do. I get it now. It's like, you got this guy, he's in this big corporate job, starts talking about like some computer program he can make. And his only thought is like, man, this is gonna put half the people on this floor out of a job. Like, get the fuck out of here. You know, like, I need my paycheck. I want my bonus this year. I don't, like, don't automate anything. Like, get out of here. Anyway, that was like very...
[12:10] Strange to me. Like, I didn't understand that at the time. Why would you not make something more efficient? The reason I quit, I remember there was one day we were all sitting around, me and a bunch of other 20-something-year-olds. So we were like just data analysts, data monkeys. The path was if you put in a few years of that, say three to four good years, the bank would pay for you to go get your MBA. And then once you get your MBA, you get to come back and,
[12:39] and you get one of the higher up jobs and you start making really, really good money. That was the trajectory that everybody was on. And so my coworkers, the team one day, everybody was sitting around. One of their favorite conversations was to talk about all the shit they were gonna buy
[12:56] once they came back from their MBA and were making like quarter of a million dollars a year, 400K a year, whatever it was. And it was like, this guy, he was gonna buy a boat, and this guy was gonna buy a BMW, and then this guy was gonna buy a lake house, all this shit. It was like, that was the whole conversation. Like, oh man, what kind of boat? Oh, that's sick, bro. Like, I'm gonna get this car. You know, like just on and on. And I remember one day, one of them turned to me and said, what are you gonna do, Mark?
[13:25] And I was like, I don't know, I think I'd like take a sabbatical and travel around the world for a year. And if it was a movie, it'd be like a record scratch. You know, like it just like everybody just like stopped and looked at me like I just farted in an elevator. And I was like, man, I am so in the wrong place right now. Like this is just awful. So the takeaway from that is that,
[13:50] It was the wrong fit, but also I feel like you got a lesson in, I call it the metaphorical time zone. Because I live in New Zealand, if somebody in California says, what day is it? It's like, well, it's Tuesday for you, but it's Wednesday for me. If I were to say it's 8 o'clock...
[14:07] I wouldn't be wrong, but it's not the only answer. Just because it's true for me doesn't mean it's true for everyone. And so when you go to your boss saying, we can automate this, it's like, well, that's true, but it's the right answer for you, it's the wrong answer for him, for his needs, his motives are different than yours. One of my really good friends worked at a very large corporation, and I remember telling him this story soon after I quit.
[14:36] And he wasn't surprised. He was like, oh, of course. And I was like, really? Like, why? When you're running a company with 50,000 employees with a hundred billion dollar market cap or whatever it was, you gotta be really careful. Like creativity is destructive, right? Like automating one aspect of data collection
[15:00] not only is it disruptive internally, potentially puts a lot of low level people out of jobs, it potentially affects like what the higher ups need to know and understand. It affects the company's relationship with the data providers. It affects the company's IT department. You know, it's large organizations move very, very slowly for a reason. And it's because it's the status quo
[15:28] It needs to be protected and not out of any sort of like ideological, it's just, you have to be careful. Like stuff breaks easily. And when you've got that many people and that much money on the line, what you have works. So like really only change it if you're really, really sure that the new thing is gonna work. And if some smart ass 24 year old comes in and starts telling you he can program this thing,
[15:54] you know, maybe don't believe him at first blush. And maybe tell him to shut the fuck up, go back to his desk, put in six months, and then come back and talk to him about it, right? Like, I didn't even know how to do my job yet. And I was already trying to think of ways I could...
[16:10] program a computer to do it for me. So an older man now, I get it. But at the time, I was just like absolutely shocked. But again, it comes back to, it's a culture thing, I think. Certain people's personalities are well-suited for certain environments. My personality was absolutely not suited for that environment. And...
[16:27] It taught me, I guess, just because you're good at something, like I'm good at math, I enjoy numbers. Just because you're good at something doesn't mean you should do it. And especially with an occupation or a job, you know, there are a lot of considerations around social relationships, culture, identity. You could be great at the job, but if you're in a terrible environment, then it's not going to be satisfying.
[16:50] Right. Funny thing. I just thought about this. One of those guys on my team came to one of my events years ago. It's funny. He didn't tell me this personally. He like got up at the Q&A time and told the audience. He said that when I quit, everybody was shocked because I told my boss, I was like, I'm going to quit. And he was like, what are you going to do? And I was like, I'm going to go make a website. And my boss was like, all right, good luck. You know, and it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's, it's
[17:19] It's a very competitive environment. And a lot of people who were there fought very, very hard to be there. And this guy at my event, he said that when I left, people made fun of me for a long time. Like, oh, you gonna go create a website? Is that what you're gonna do? Good luck. But he told me later, he was like, yeah, dude, that place sucked. He said almost everybody left after a couple of years. It was just absolutely soul-destroying.
[17:48] You know, I went to my class reunion when I was 28. I was a full-time musician at that time. I was a professional musician touring the world, making my full-time living doing gigs. And I just happened to be in Chicago when I got some kind of announcement that our 10-year class reunion. So ordinarily, I wouldn't have gone to that kind of thing. Yeah, sure. I'm in Chicago. Why not? I showed up.
[18:13] my long hair and my weird purple shirt. And everybody else was 28, but holy fuck, they looked 40. They were all like in suits with double chins and just baggy eyes and just like pushing papers from left to right across a desk for Motorola. Everybody's job was like, I'm a manager at Motorola. I manage the regional Midwest telecom division. Yeah.
[18:40] What are you people doing? I was like, you had dreams. You wanted to be things. What the fuck? And they looked at me with kind of the same kind of thing. I was always like the freak with the heavy metal patches on my jacket and the long hair that they were trying to get into a good college. And I looked like I wasn't going to amount to anything. And at the class reunion, they said a few different people, either in the moment or a few emailed me later, saying that they were kind of like,
[19:08] Jealous that I stuck with my dreams, and they gave up their dreams just to take some dumb job. And it reminded me of something that's worth mentioning in this episode, is that I never work for money. Even as a teenager, nothing I've ever done...
[19:27] has been for the money. Any job I took, it was only if I would have also done that job for free. Because everything had to be a learning experience. It was like it was all leading to something more. I've never worked for money in my whole life. I'm curious, like what was the first job that taught you something? So yes, telemarketing...
[19:46] was my first job because I was 16 years old and I had really long hair. So I was not presentable. And so I went for a job at Time Magazine. I grew up in Chicago. My job was on a huge floor with like 100 people on the phones calling people that already had a subscription to Time Magazine or Sports Illustrated or Life or People Magazine and to renew their subscription over the phone. So...
[20:12] So I worked there for a few weeks where I would call people and say, hi, my name's Derek Sivers calling from Time Magazine. I'm calling to see if maybe you might want to renew your subscription today. And they say, no, leave me alone. OK, thank you. And I did this for a couple of weeks.
[20:33] And my manager was told that she had to fire me because I was terrible. And she said, look, you remind me of my little brother. So I asked my boss to let me give you another chance. So let's do this. She said, come here to my manager's desk. Listen to what George Amos is doing.
[20:52] So I put on her headset and I got to listen in to another salesman that was the top performing guy on the floor. So what George Amos would do is he would call people up. He'd say, hey, I'm calling from Time Magazine in Chicago. You know, is this Mr. Williams? Yes, it is. Mr. Williams, you still living at 321 Main Street?
[21:10] Yes, yeah. All right. Mr. Williams, I'm just calling to renew your subscription today. We've got you in for a much better rate than you had last year. We're going to renew you for three years this time. We see that you've been with us a long time. We appreciate it. So we're going for the three-year renewal. It's going to save you a lot of money. Instead of you paying $50 a year, you're just going to be paying $21 a year, lock you in at that rate for three years. All right, Mr. Williams. All right. Thanks for the call. Bye-bye.
[21:30] Just like that, George Williams was getting these three-year renewals every few minutes, whereas I was struggling to get one renewal a day. So I listened to this and went, wow. All right, for one, lesson in confidence, just assuming the sale, not asking for the sale, just like, yeah, we're going to do this today. We're here to get this done. That's just assumed. But to me, the bigger lesson is...
[21:54] was I don't have to be myself. Like, this is me being myself. Like, hi, I'm Derek. I just want to know if maybe you want to renew your subscription. That felt like the real me. So what I had to do was get on the phone and imitate myself.
[22:10] George Amos. I had to not be myself. So I did it. I got on the phone. I said, Hi, my name is Derek. Is this Mr. Hipkins? All right. Mr. Hipkins, are you still on 23? I'm lame. Yes, sir. All right, Mr. Hipkins, I'm just calling to renew your subscription today. I see that you've been with us a while. I just I appreciate your business. So we're going to give you a much better rate than you had before. Instead of the $52 a year you've been paying, we're just going to renew you for $21 a year. That's our three year subscription rate. You won't have to do anything for the next three years. You're all locked in. All right.
[22:39] Okay, great, thank you. That's it. And I was like, bang, bang, bang. I was making these three-year renewals. And within a week, I was the top-selling guy on the floor. A team of like 120 adults and 16-year-old Derek was the top seller on the floor because I was imitating George Amos. I still felt like my internal self...
[22:59] was not the guy that was saying this stuff on the phone. That was George Amis. That's his real self. You know, that's who he really is. Me, that's not really me, but I'm acting like George Amis to sell more subscriptions. Later, when I was the ringleader MC of the circus...
[23:18] I had to do the same thing because, again, they asked me to be the ringleader and I was really bad at first and they were almost going to have to fire me. And they said, just be more sensational. I went, because at first I would just get up on stage and go like, hey, everybody. Well, yep.
[23:37] We're at the circus. So I guess take a seat. And yeah, we'll come out pretty soon and entertain you. You know, I was just being casual. I was being more me. And they said, no, don't be yourself. Be your ringleader. So I went out there like passive aggressively one time. I was like, all right, fine. I went out there and I was like, ladies and gentlemen, what you're about to see is one of the most amazing shows you've ever seen. We are the Mind Circus. We are going to have entertainment. We're going to have this and that. You're going to take your seats and ready for the show. And...
[24:06] I went backstage almost aggressively, like, there! I did what you said! And they were all applauding. They're like, finally! Thank you! That's what the audience needs! And I was like, oh, really? And so that was it. For the next ten years, I would put on the ringleader persona, because that's what the show needed. I was like, wow, alright, that's not being me. But this raises a really interesting question of, like...
[24:30] What is an identity in the first place? And what is authenticity, right? Because, you know, what you did is classically known as like modeling behavior. It's a basically it's one of the fundamental ways that humans learn. But from one perspective, the authentic Derek was, you know, insecure, quiet, nervous, okay.
[24:53] a little bit too casual and he had to take on or assume a lot of traits and behaviors that weren't authentically him. But if you really start thinking about it, what we generally consider authentically us is just learned behaviors from before that we modeled off somebody else at a different time in our lives. Yes. So in a way, like authenticity or identity in general, it's a very fluid thing and we
[25:21] This is actually something we recently did a video about Korean culture. And when I was doing research on that video, I was reading a lot about Confucianism. And one of the things that I discovered is that a lot of East Asian cultures, like in Japan, Korea, China, they don't have this notion of a fixed identity. Like Westerners, we like to think that like, Mark is Mark, whether he's on a podcast, or he's hanging out with his mom, or he's at the grocery store, he's always Mark. Whereas,
[25:48] In some of these East Asian cultures, it's accepted and assumed that you behave differently in different contexts. There is a podcast mark. There is a business mark. There is a family mark. There is a public-facing mark. There is a private mark. Not only is it not seen as inauthentic to be different in all those contexts, but it's actually seen as immature if you are not different in those contexts. You should treat your boss differently than you treat your mother. You should treat your best friend differently than you treat your wife. You should behave differently at home than you do at work.
[26:18] and there's shame in not doing those things differently. So I thought that was really fascinating, that this kind of obsession of authenticity in Western culture, especially recently, it might just be a moving target. I like that. When I was a senior in college, I got a job as a doorman at my favorite bar. And at the time, you know, when you're 22 and your entire life revolves around...
[26:42] girls and parties, this was like the coolest fucking job in my mind that I could have. And I remember it was really interesting because
[26:51] It taught me how arbitrary authority is. You had this bar, I used to go to it all the time, probably two, three times a week. It used to be a line down the block. Sometimes you'd try to like cut your way in, talk your way in, find somebody you knew in line to get in. And then one day I saw that they were hiring and I just went in and applied and I immediately got hired. And the next night, I'm the guy at the door deciding who comes in and who doesn't. And I remember just thinking, I'm like, wow,
[27:17] In less than 24 hours, the dictation of who has the authority to decide who gets to go into what space is like completely flipped. And it's made up. There's no like, I don't know, higher power like dictating you must wait in line. So it just it gave me an appreciation of how I guess fragile.
[27:36] order is in general. Like it doesn't take much to like, just kind of rewrite some rules or, or, you know, put yourself in a different spot. This was probably the first time in my life that I learned that you don't necessarily always want to get a job in an area that you love.
[27:53] So I always assumed that working in nightlife would be extremely exciting and fun, but it turns out it's unbelievably boring and dull. It's very repetitive and it's actually obnoxious because you're basically being paid to babysit all the drunk people who are having fun, which is the most unfun thing you can possibly imagine.
[28:13] I got fired after three weeks because I was talking to too many girls. I kept getting yelled at by the manager because I was like not paying attention or doing my job. Like the whole reason I took the job is because I wanted, I'm like, I want to get paid to be at the party. And it turned out that I wasn't getting paid to be at the party. I was being paid to regulate
[28:33] and administer the party, which was not exciting to me. So it's actually the fastest I've ever gotten fired from a job. It was three weeks. Didn't doing that job, though, give you this insight now? Like, bars are everywhere on Earth. And now every bar you see, you've got a little bit of insight into what it's like to be on the inside. You've got some empathy with the people that work there. Totally. Empathy and a lot of respect, especially, like...
[29:02] the people in the back, the bartenders, but also like the busboys, people like replacing all the liquor bottles, cleaning the floor. Like there's so many thankless jobs in that industry. It's also one thing that's not talked about a lot with that industry is that it completely overhauls your social life because you work such strange hours. Your peak work week is, you know, Thursday to Sunday, like 5 p.m. to...
[29:26] 3 a.m. So you have no social life on the weekends. That's your working. So your free time is Monday, Tuesday, Wednesday, which basically limits you to only being friends and hanging out with other people who work in bars and restaurants. So when you are part of that world, you realize that it's like this weird situation
[29:43] parallel universe that most of us aren't exposed to. And everybody in that industry knows each other as well. So it's like, cause every bar, you know, every bartender was a bartender at some other place. And the, this door guy was used to work at this bar, you know, across town. And so everybody knows somebody somewhere. So it's like, if you really get embedded in that world, which I did not, it's like a whole subculture. It's really interesting. You know, when people ask you for career advice,
[30:07] I feel like I'd almost prescribe this to people. It's like, go work at a bar for three weeks and get fired. Go work in a kitchen at a restaurant for a few weeks. But this idea of like, just even a few weeks of experience with something can help give you an insight into this thing. Then for the rest of your life, you'll be able to understand this little subset of humanity a little better. All of the employment that I've had.
[30:32] I've never lasted more than a couple months. Two of them, I got fired and then two of them, I quit. Like getting fired never bothered me. Like, I don't know. Maybe that's just me being naive, but like I remember the manager threatening to fire me and I was just kind of like, well, yeah, I mean, if I get fired, that's fine. I'll just go find something else.
[30:52] Like, I don't know. There was no deterrence. Like I had no sense of, man, I better shape up and do a better job. I remember when I was young, I lived on a friend's couch for about six months. I built my first websites on that couch. And I remember thinking to myself very clearly, like, this is the point in my life where I'm going to have the fewest attachments.
[31:10] I'm going to have the fewest things to lose. And if I can be comfortable with nothing, then like nothing can ever control me. If I'm never afraid of being broke, then nobody can control me with that. No paycheck is ever going to feel more important than, to your point, like doing something that feels more important. That resonates on a very deep level for me. I think I've always been the same or usually been the same. I also just think that like I don't really mind hardship like –
[31:38] it doesn't seem to bother me as much as it bothers a lot of people. And it's not to say that it doesn't suck. It does suck. But like I'd rather be doing what I like with my time than,
[31:51] and be broke than the opposite. Okay, I'm gonna sound like a new age asshole for a second, but the saying hardship sucks, to me it's like the, it depends on where you're focusing. I've never felt that hardship sucked because my eyes were always up here on the horizon. I was always looking there towards where I was going.
[32:18] And if I tripped over a rock for a second or stubbed my toe, who cares? All right, whatever. I'm going there. Whereas I think that if people get too present-focused or too kind of narrow-focused, they metaphorically might just be looking down at the muddy trail they're on. And they're like, oh, man, there's rocks. It's muddy. But it's like, I don't care. I'm looking up here. Don't look down. Look up where you're going. And sorry, I know that sounds like such a cliche, but...
[32:45] There was a time when I was running a CD Baby, I was speaking at a conference, and the panelist, the moderator, asked for questions from the audience. Somebody from the back said, what's the hardest, most difficult thing you've ever had to do running this company? It's been the hardest time. And I sat there and I thought for a second, I'm like, nothing. Nothing's been hard. There hasn't been anything hard about running the company. And the guy came up to me later after the panel was done, and he said...
[33:14] I think you've just got a positive mental attitude. He said, I'll bet you, you've actually had difficult things happen in the last 10 years. You just don't even think about them. You're just not focused on them because you're focused on something else. I guess, I don't know. To me, it really does sincerely feel like, no, I haven't had any difficulties. Nothing's been hard.
[33:33] There have been no setbacks. Everything's been great. But maybe, like maybe if I went back into my diary, I'd go like, oh yeah, five years ago, that was tough. But I'm just not thinking about it. I just keep my eyes up here on the horizon. Well, it's also you, if you enjoy...
[33:49] whatever you're struggling against, then it doesn't feel like suffering. It actually feels the opposite. It feels invigorating. I look at my own experience and like writing is a great example. Some people writing is torturous. And I mean, for me at times too, it can be difficult, but like, it's a difficult that I like, I enjoy it. Like there's, it's very satisfying and
[34:14] Actually, I've run into this recently in terms of fitness. So I started training for a marathon a couple months ago. And I discovered I worked up to about 13 to 15 miles. And I discovered something, which is that anything under eight miles, I really enjoy. And it's like even if I push myself and I'm exhausted and I'm like trying to go for a best time or something, if it's like a 10K or something, I really enjoy it.
[34:42] As soon as you get up over eight or 10 miles, it fucking sucks. It's a suck that I don't enjoy. I don't like the struggle of plotting at a very slow pace for two and a half hours. So I said, fuck it. So I gave up that goal and I said other goals. And...
[34:59] Nice. And it's funny because like a lot of people in my life are like, no, you can't do that. You've been training for two months. Like you can't stop now. Then there are other people who are like, what is your audience going to think? And I'm like, my audience is going to get a lesson and don't stick with a goal that makes you fucking miserable. Like it's not worth it. If you find the struggle you enjoy, you don't suffer through it. Wait, have we talked about landmark before? No. I'll just say this quickly.
[35:25] This landmark forum, two of my dear friends are really into it and said I would love it. One of them basically made me go. She basically signed me up against my will and said, there, I just signed you up. Just show up Saturday. Go. And it was dreadful and awful, but it had a wonderful punchline. Dreadful and awful. I'm going to get a excuse from the CIS letter. I know it. No, it had a wonderful punchline.
[35:55] That basically nothing has any inherent meaning. Life is underscore. That word is blank because life has no inherent meaning. Nothing has any inherent meaning. This microphone does not have meaning. This podcast does not have meaning. It's just a podcast. If you say it means something, that's you putting meaning into it.
[36:17] And they kept emphasizing this point over and over and over again to me. And it was just like, oh, I love this. So, yes, I hate this weekend, but I love the punchline. I liked it so much that I signed up for the Advanced Landmark Forum a month later. So I went to the Advanced one and kind of like you after the eighth mile...
[36:35] I was like, I don't like this. This is all about like group dynamics and like, I'm just not enjoying this. And I think for what I want in my life right now, it's not this. There's other things I want to be doing with my time right now. So two hours into it, they said, okay, we're going to put you into groups of six. So, you know, literally just 30 seconds after they put us into a group, I turned to the other five. I said, guys, I'm leaving.
[37:01] And they said, no, they said, that's you're breaking your integrity. No, this means it's something, something you have. And they kept telling me all these things that it means. This is what it means that I'm leaving. I said, no, like, it doesn't mean anything. It means I'm leaving. That's it. It has no other meaning. I'm leaving now. Goodbye. And they're like, no, you can't because, because integrity, because I was like, goodbye.
[37:23] Your goal should serve you, not the other way around. Yes. Just because you set a goal doesn't mean you have to be a slave to it. And I think there's a little bit of a romanticism of like, you got to grit through it. You got to suffer, bro. You got to like fucking nearly die to get there. And it's like, do I really? Like, I don't know.
[37:42] I'm okay. Yeah, it's like, well, I'm doing this for my health. Yeah. And there are other things I can do for my health. This one makes me want to die, so that's not good for my health. Yeah, and not to mention that running a marathon is actually not that healthy. Yeah. I like what you said about when you were talking about finding a better reason than money. It reminded me of like when I was starting my online business and blogging, I made no money for like a year, two years. And...
[38:10] There was a period of time that I was living with my girlfriend at the time, and she was financially supporting me. And I remember talking to her and telling her, I said, you know, it's even though I'm broke now, I feel like I'm learning skills that are going to serve me for the rest of my life. Say like take marketing or copywriting. I was terrible at it the first year or two, and I didn't sell anything. But I had to go through that to get to the point where I could sell something.
[38:39] Anything. And that's a skill that's served me ever since. It's almost like it's an investment. Like it's, it's like putting money into a retirement account or something. Like there are a lot of things in life that you can do that actually end up being a more positive ROI than just a paycheck in the long run. Way more. Way more.
[38:59] And I think that that relates to your like keeping your eyes on the horizon thing. Like if you're always just looking at where the next paycheck's coming from, you're not thinking about, well, maybe I take less money to learn this skill that will help me develop my career. And then five, 10 years from now, I'll actually be in a much better place. And not to mention the psychological benefit of having that long-term vision and goal for yourself.
[39:20] which keeps you motivated, keeps you happy, keeps things feeling not difficult, even if there's some struggle along the way. Yeah. And again, it sounds like such a cliche, but it puts everything into perspective. You know, whatever you stumbled over today is no big deal if you keep your eye on that. Mm-hmm.
[39:42] I wonder about your former colleagues, if they were happy when they got the BMW there. Did it. I'm guessing not. I'm guessing they needed a Porsche or a Ferrari or something. I don't know. I've met enough people to know where that ladder goes. I remember...
[40:02] When we met, you gave a talk. We met at a conference many, many years ago, and you gave a talk at that conference. And I remember the thing that stands out to me that you said at that conference, and this is notable because at the time I was not wealthy and you were. So you said luxury is a trap because it's enjoyable for a short period of time and then your brain adjusts and then anything less than that feels like suffering. And so I remember you had this whole thing about...
[40:29] you know, intentionally choosing high friction things, you know, fly economy, stay in a shitty hostel, walk,
[40:40] to a place that feels a little bit uncomfortable to walk to because it just keeps you grounded and keeps resetting your baseline expectation of what life should be giving you. I still avoid comfort. I still do that. Yeah. I was thinking about my kids' education because the New Zealand school system's not very good. And so I feel like it's kind of more up to me. Now I'm gonna hear from landmark people, New Zealand parents. I'm gonna, this episode, we're gonna get a lot.
[41:09] All dismal. I was thinking about like, okay, if it's all up to me, what are the life skills, the know-how that I want my kid to have? So I came up with some myself. Then I just decided to search the web for other ideas. And there was this one that was like, you know, I think it was maybe on the art of manliness or something. It was like...
[41:27] gotta know how to make a good steak. You know, you gotta know how to, like, make a good gin and tonic or something like that. And I was like, no, these are all just fucking pleasure things. That's not survival. That's like, who are you trying to impress? Your buddies at the bank, right? Yeah, right. You know, Mark makes a good steak. Maybe we should give him a promotion. What the fuck is that? You know? That's some fucking hedonistic pleasure shit. No, I'm talking about survival. Yeah. I want my kid to be able to
[41:55] survive in any situation, like survive in a crowd, survive in a disaster, survive in a new country where he doesn't know anybody. And, you know, making a good gin and tonic is way... because those are pleasure things. And again, I just realized, like, yeah, I do not value pleasure at all. What's the most pleasurable thing you do? Well, I think of it all as removing obstacles. So my definition of home is,
[42:22] This subject came up recently with friends. We were talking about, like, what's home to you? To me, home is the place with no obstacles. Because ultimately, I'm a live-to-work guy. I exist to work. I love my work. I don't think of it as...
[42:40] My work, obviously, for money, I think of it as like my life's work. This is like my reason I'm on earth, or I've decided to make it my reason I'm on earth. It's like my kind of primal I am here, I exist statement. This is what I'm doing. And so, of course, I'm fucking driven completely by...
[42:58] I don't sit around and hang out and do nothing. I try to use every single hour I can to work. So to me, home is the place that has no obstacles to my flourishing, which means my work. It's not too cold or too hot. It's not too noisy. That's what feels like home is the place with no obstacles. So if I'm seeking pleasure, it's really more of just like seeking to remove obstacles. Interesting.
[43:26] I think you're more balanced than me when we've talked about this. I'm actually really glad that you're more successful than me. I feel very like monomaniacal driven. And I think it's really kind of reassuring that I think you've had a more balanced approach to life and yet completely thrived. That may be the first time anybody has called me balanced. Really? Yeah. Yeah. I...
[43:52] You play games. You have a healthy relationship. That's true. I mean, yeah, I would say balance is a relatively new thing in my life. Okay. But I'm similar. When I kind of get obsessed with something, I have trouble not going all in on things. And similar to you, I've actually had to... My problem has often been I have to consciously stop myself from working to allow space for other things in my life. So...
[44:22] You had an interesting career as a musician from a circus to playing in a band in Japan professionally. What was that transition like? And what are the lessons there? Okay. Circus clown and Japanese rock star, Derek Silver. Yes, yes, exactly. Okay. The tale is, I was 22 years old. I was living in New York City.
[44:47] I was renting an apartment with three roommates. We were paying $333 a month each. One of my two roommates was an assistant engineer at a recording studio in New York City. And the Japanese pop star Ryuichi Sakamoto was there recording. My roommate was just the assistant, like, wrapping cables and stuff. But he came home one day and he said, hey, Ryuichi said he's going out on a new tour. He's got the drummer from Peter Gabriel, the bassist from Miles Davis, and he doesn't have a guitarist yet. Do you want the gig?
[45:17] Fuck yeah, I want the gig so bad. Oh my God. And so he got me a recording of like the tracks that they were working on. He took it home for the night. Like he got home from the studio at 11 o'clock at night. I took the little recording and I stayed up all night long, literally till sunrise, writing guitar parts for Ryuichi's new album that had no guitar on it.
[45:38] And I brought it into my little home recording studio, wrote guitar parts for it, recorded it, mixed it back onto the tape, gave it back to my roommate at seven in the morning. As he's like on his way to work, I was like, here, give this to Ryuichi, tell him I want the gig. So he was able to give Ryuichi his entire album now with my guitar on it. Then I had to do like two more days I spent, like I transcribed every cello part on his previous album, like in the, you know, bass clef on staff music, whatever, you know, with the quarter notes and eighth notes and sixteenth notes.
[46:06] I transcribed it myself, handed my roommate that. I said, tell him I really want the gig. And then finally I got the call a couple days later saying, yeah, come on in. You've got the gig. So at the age of 22, I got to tour Japan. I was so fucking cloud nine. I was so happy. Great gig, but it's like I got it. I think the lesson learned is...
[46:30] When a gig comes up that you want, don't be casual. Like, go fucking over the top, all the way maniacal until you get the gig. Because that's what you have to do to prove that you want it. It'd be so easy for somebody to look at that story and be like, oh, he's so lucky. But it's, I mean, yes, there is some luck that your roommate happened to be the engineer. When...
[46:51] luck gave you an inch and you took a mile essentially like you literally put everything you could have done into the next 24 hours yeah to make it happen when life does hand you those opportunities which we all get them they're very rare but they do happen like that's what i always tell myself is i'm always like i won't regret staying up another couple hours because
[47:15] I would regret not staying up a couple hours, right? Exactly. So stay up a couple hours. The luck thing, there's another minor lesson from this, which is to be in the place where things are happening. That, yes, it was lucky that my roommate was the assistant engineer, but that luck happened because I moved to New York City, even though I could only afford $333 a month rent. I lived in Queens in a shitty apartment with three roommates because that's what it took for me to be in New York City in the middle of things where things are happening.
[47:44] I think it's still true. Even in the phone it in, work from home, internet age, I still think there's so many more opportunities that just happen if you're in the place where things are happening. For sure. I think Scott Galloway talks about this a lot. You know, one of his primary pieces of advice for talented young people is just go to a mega city, regardless of what career you want to get into. When you're young, you have few attachments, get to a big city and,
[48:12] Because it's just the concentration of talent, the concentration of industry, of companies, of opportunities, it's all there. You never know who you're going to run into. It's funny because I grew up in a place that is now a great place to go for opportunity. But when I was a kid, Austin was not a happening spot. And from the age of 15 or so, I just knew I got to get to the East Coast. Okay, I'm going to wing it and to talk about something I've never talked about before, but...
[48:38] When I'm in New York City, I feel that I'm surrounded by greatness. And it makes me want to be a better person. I feel like it, in a real way, makes me work harder. It makes me lift my expectations of myself.
[48:54] I set higher expectations for myself because I'm in New York fucking city. Not only that, I'm in Manhattan in Union Square. Some of the best writers ever have walked these streets right next to me or are walking these streets right next to me right now. Or are just a block away writing a great book and I'm right here. It elevates my expectations. And I even get that from...
[49:17] places I live. When I lived in Singapore, I was actually really inspired by the story of Lee Kuan Yew and what he did to lift Singapore out of the muck and into greatness from 1968 to 1988. That was really inspiring to me. It made me want to be a better person. And again, I felt like it set higher expectations for myself.
[49:40] And I've thought about that now that I'm living in very comfortable New Zealand, but it's just comfortable. It's a lot of nature. And I'm missing that sense of being around greatness. And I've noticed that I have to really generate it myself. I have to get it through the internet. But I miss that energy of my time living in Los Angeles, my time living in New York, my time living in...
[50:02] Even London, I lived in London for just a year, but just walking W1, West London, just like, oh man, such greatness has happened here. I wanna make something this great. It inspired me in a real way. It's funny, all my friends from New Zealand and Australia say that that's why they left when they were young, because they aspired to do something great. And New Zealand and Australia are amazing places
[50:28] But they're comfortable. And they're countries that are very optimized for a very comfortable life. And if you're really trying to do something extraordinary or push yourself extremely hard, it's not conducive. It's funny. Paul Graham has this thing. He says that every city is quietly whispering something to you when you're there.
[50:49] Actually, no. Sorry, I've got the little essay memorized. Oh, you do? It's one of my favorites of his. It's, um, New York is you should make more money. Boston is you should be smarter. Los Angeles is you should know more people. Bay Area, let's say, is you should have more impact. Funny, because that's what drew me to New York, and it's also why I left. Because...
[51:11] it felt like no matter how successful I got, that feeling never went away, that I wasn't doing enough, that I wasn't earning enough, that I wasn't successful enough. And I saw it too in my successful friends in New York. You know, I would hang out with guys who had 10 times the money I did, and they still felt that way. They still felt like they weren't doing enough, that they weren't earning enough. And I was like, man, this is fucked. Like if that guy feels this way, like.
[51:39] Yeah. I should not, this is not a healthy place to be. I actually, I have a very contrarian take on New York in that New York is best experienced broke. Interesting. Because all of the great things about New York are free. Or not free, but they can be experienced relatively inexpensively. Like the great thing about New York is the proximity. The density. And you can experience that when you're broke. As long as you're in the city and have enough money to like buy a sandwich or...
[52:09] a coffee, you can experience it to some degree or another. When you really try to actually like build a nice life, the city doesn't let you.
[52:19] Interesting. To use your term, you cannot remove all the obstacles. The city will not let you. And part of that is what makes it so great because it keeps people like striving and fighting. But yeah, when you're broke in New York, you feel like you're getting the best bargain in the world. When you're rich in New York, you feel like you're getting screwed every which way constantly.
[52:40] I could see that. I'm curious, what did you learn from Ryuichi Sakamoto? Yeah. The one thing was, I don't have imposter syndrome. I was 22 years old. The other guys in the band were all closer to 40. They were super accomplished. I mean, holy fuck, Victor Bailey on bass. He was like cover of Bass Player Magazine three times. This dude played with Weather Report, Miles Davis, and oh my God, Manuka Chase.
[53:05] my favorite drummer in the world, the guy that played on that song Sledgehammer by Peter Gabriel with a, it's got such a style. And there's me and I'm 22. And I felt just like, all right, fuck it. You hired me. I'm here. You're stuck with me. And it's like, I've got a valid reason to be here. I'm not, uh, the best guitarist, but I can do my little James Brown funk thing very well. And that's what was needed for this gig. So I have every right to be here. And, um, yeah,
[53:34] Yeah, I was a bit of the punching bag.
[53:37] of the rest of the guys like really made, you know, I was 22 years old. And I, you know, I've got a very, I'm an enthusiastic dude. Yeah. I'm the opposite of jaded. Yeah. And, uh, so of course you'd imagine me at 22 in Japan for the first time. And it's even amplified. I'm like, wow, this is amazing. And all these like jaded, you know, 39 year olds that have seen it all been there, done that. They're like, yeah, for them, this was like the Ryuichi gig was just another gig. They're just like, dude, calm down.
[54:04] But they made fun of me a lot. But I mean, the main lesson I think was giving it all for getting the gig. But then even doing it, just this feeling of like, I have just as much right to be here as anyone. But... Do you think you had to earn that feeling, like through practice and...
[54:23] developing your craft. There are some people who practice incessantly and are excellent at their craft, but they still feel imposter syndrome. I had the right to be there because I knew I could do it. And I knew from the audience's point of view or, and even Ryuichi's point of view, I was playing the parts he wanted me to play. By the way, I never, I didn't connect those two. He basically hired me to just play what I had played that sleepless night on the demo I made. He said, just do what you did. I said, okay.
[54:51] And so it's like, all right, he's basically saying, I like the way you play. Be you. I'll pay you. Come on stage. Okay. I have to tell you the Alan Tepper story before I forget. So imagine this. So I'm working inside Warner Chapel Music Publishing in New York City, Midtown Manhattan,
[55:07] But the year was 1992, which in hindsight, I found out was like a pretty deep recession. I didn't know it at the time because I just had my job that I would just show up at. It was minimum wage. But it was a tiny office. Maybe only 20 people worked there, 15 to 20.
[55:22] But there was one room that wasn't being used, one tiny little windowless room, about the size of the little room I'm in recording right now. And one day, a stranger showed up there and was working in that room and said, oh, hey, I'm Alan. I'm going to be working here now. I said, oh, OK. Hi, Alan. I said, I didn't know you were hired. He said, no, I'm not actually hired. I'm just going to be working here.
[55:46] I went, okay. Alan Tepper, it was a recession. He had been laid off from inside an advertising gig. And he looked at the world of music publishing. Music publishing owns the copyrights. So if you hear a Stevie Wonder song in a commercial, Stevie Wonder gets some money, but his publisher gets half the money. You know, the money split 50-50 with the publisher and the artist.
[56:11] So Alan Tepper came in and he looked at Warner Chapel Music Publishing, which was the largest music publisher at the time, and he said, you're not doing enough to get your music into commercials. I think I can get your music into commercials better. Just give me a desk. You don't have to pay me.
[56:28] Give me a desk. Let me show you what I can do. Because Warner Chapel was not hiring at the time. This is the key lesson here. They were not hiring, but he looked at their business and said, I think I can make your business a lot more money. You don't have to do anything, but just give me a desk and a phone and let me say that I'm working for you. Yeah.
[56:45] And they said, all right, show us what you can do. And within one year, Alan Tepper made more money for that company than everybody else in the rest of the office combined. He ended up becoming like the highest paid guy and like the biggest success story of Warner Chapel Music Publishing for years afterwards.
[57:01] But he made a job for himself. They were not hiring. So when I hear people say like, I can't get a job, I think, well, just you got to have some gumption. You got to have some insight. You got to just look at a company that you like. Have some, what's that word? Impetus to make something happen. Look at it and you can make yourself a job. It doesn't matter if they're hiring or not. If you go to them and show them that you can make them more money, you can make things happen. And to me, Alan Tepper was the...
[57:28] Perfect example of that. Find a way to add value. Make yourself a role. I get a lot of cold emails, people pitching me on stuff. And there's maybe one or two a year that I'll actually bite, I'll respond to. I mean, obviously there's a lot of terrible ones, but the ones that kill me is they'll have a great subject line, a great hook, and they'll have a great subject line.
[57:50] They'll offer something really intriguing. And then the close of the email is, if you want to find out more, reply and we'll get on a call. And I'm like, no, just send me the fucking work. Like, dude, if you can live up to everything you just promised, just send me the work. And I feel like a lot of people...
[58:09] they get really insecure about like, oh, well, I can't work for free or I can't give away my work for free. It's the best way to sell your services. It's the best way to convince somebody that you're valuable. If somebody gives me a day's worth of free work and it's valuable, my immediate thought is, fuck, I should hire this guy. Like he did this for free. Imagine what he'll do if I pay him. Holy fuck. People's brain doesn't go there for some reason. I don't totally understand why.
[58:39] But it drives me crazy. It absolutely drives me crazy. No, I'm not going to hop on a call with you. Just send me your fucking ideas. And if they're good, then I'll pay you. And if they're bad, I'm not going to use them anyway. So, oh, man. Well, speaking of, we were talking about relationships earlier. I worked as a professional men's dating coach for a number of years. So that was my first. I'm so glad you're going to talk about this. You're going to talk about it? Yeah. Yeah.
[59:03] I learned a lot, man. I learned a lot. So for people who don't know, my first online business that got traction was men's dating advice. And I kind of, it's a long story. I happened into it.
[59:15] kind of unwittingly. Next thing I knew, there were a bunch of men in Boston who were like, hey, if I pay you 500 bucks, will you like take me out and help me talk to girls? And I was like, sure. Like what better way to earn a living? First of all, there are a lot better ways to earn a living. Like anything, again, it's the lesson from the bar all over again. It's as soon as you monetize an activity, it changes your relationship to it. And in some cases,
[59:44] the monetized version of that activity is way less fun or way, way less satisfying than the hobby version is. And I think that's true about a lot of things. And I think it's just important for people to be aware of. I actually struggled very much early on in that career because it felt like a lot of my social relationships became objectified. You know, it's like if I went on a date with a woman and it didn't go well,
[1:00:09] Suddenly that's like a professional liability because it's like, what if I'm out and some potential client sees me with a girl and she's shooting me down. It became really weird. It was definitely a mind fuck. But the biggest things I learned doing that job was I was shocked how most of the men, when you really got down to it, I did it for about five years. I worked with probably
[1:00:33] around 100 men, when you really came down to it, I think most of the men, it wasn't about, I don't know what to say, or I'm nervous around girls, or help me buy a shirt that doesn't look like I'm a homeless person. It really just came down to a lot of men had very unrealistic expectations about gender, dating, and sex. Their map of reality was very warped, either based on,
[1:01:03] a fucked up family background or exposure to like some adverse events when they were young, you know, a girl who broke their heart, you know, they just had very strange understandings of, of women and dating and sex. And it was like, a lot of it was just kind of like,
[1:01:22] correcting that map, just be like, well, no, no, no, you don't have to say or do all that. No, you don't have to pay for dinner. Like you do just be normal, like chill out. I was very shocked at how many, I'd say probably 90% of my clients had no present father figure in their life.
[1:01:40] a lot of it seemed like there was kind of this desperate need for a male role model. And I, whether consciously, probably unconsciously, but like part of my job was to kind of like be the stand-in as that role model to basically just tell these guys like, you're okay, you're a good dude. Like, yeah, you deserve an attractive woman.
[1:01:59] There's nothing wrong with you. It surprised me at how many of the clients it really boiled down to that. The worst part of the job was the clients who they saw relationships very transactionally, which was why their relationships with women sucked because viewing women transactionally is not a huge turn on the women. It's not a shocker there. But again, kind of coming back to this like inaccurate maps of relationships and dating and intimacy.
[1:02:29] I found that a lot of men just like could not, they literally did not understand non-transactional relationships. They just like didn't, they couldn't process it. And if I tried to explain it, they just saw it as like another tactic to like, oh, I see what you're saying. So, okay. So I make it seem like I like her unconditionally because then that's gonna turn her on and get laid. And I'm like, no, no, no.
[1:02:55] No, that's actually the opposite of what I'm talking about. So that was always frustrating. Ultimately, I found it to be a very draining job. I honestly, I came away from it with the conclusion that most of these men actually need a therapist much more than they need a dating coach. Lines don't really matter.
[1:03:14] tactics don't really matter. Like those are placebos to kind of just get guys over their anxieties and fears. It was very interesting. It was really just an insane amount of education into like human nature and psychology and relationship dynamics, understanding how men and women see each other and react to each other.
[1:03:34] I honestly think a huge percentage of my whatever insight I have that people enjoy is a lot of it came out of that period from just intense amounts of like extreme social interactions. Because you weren't doing this just for the money. This was it was not five weeks. It was five years. Yes. So did you feel even at the time like, OK, well, I'm not just doing this for the money. This is helping me.
[1:03:59] I definitely learned, you know, that cliche about the teacher learns more than the student. I definitely found that to be true. I would usually learn way more from the guys I worked with than any women we met or talked to. You were dealing upfront and personal with a lot of men's insecurities and vulnerabilities and seeing the patterns among those. Especially, too, at a time where, like, those sorts of things weren't really talked about.
[1:04:23] publicly. There was like, I mean, there still is stigma, but back then, especially, I mean, a lot of stigma around guys admitting they're insecure or, you know, anxious or depressed. So yeah, it was, it was extremely educational. It was not satisfying.
[1:04:40] It really wasn't. I mean, there were some clients that it was. Like, every once in a while, you get like a really good guy and he'd kind of have a breakthrough and meet a nice girl. But yet, you currently are putting yourself into counseling type situations. You're still choosing to help people. So, you still get something out of it. What is that driving you that still wants to help people?
[1:05:05] individuals? Well, it is really fun to help somebody. I think the difference now is that I get to choose who I help. Whereas back then I kind of just took anybody who wanted to hire me towards the end. There were a number of clients who, you know, we would go out
[1:05:22] to a club or something, start talking, whatever. And then within an hour, it's just clear. It's like, okay, this guy is an emotional wreck. And I would just kind of pull him aside. We'd go to a restaurant or something and we would just spend basically the entire session basically kind of being a therapist. Cause I just realized, I'm like, that's what a lot of these guys need. Like they just don't have anybody to express this shit to. Like all their guy friends, judge them for it, you know, call them a fag, make fun of them.
[1:05:52] dad's not around. There's no brother. Like they literally have nobody to talk to this stuff about. So I realized that after a while that it's, they just need a fellow dude who will like listen to all their insecurities and be like, no man, it's all right. You're, you're all right. It's going to be fine. That felt more impactful than the, you know, Oh my God, I got her number. She's so hot.
[1:06:17] Do you think that's what put you on the path then of writing articles from what you learned? Totally. Yeah. What I learned is that there's not really such thing as a dating advice. It's really just a dating problem is just an emotional problem that is being experienced while dating.
[1:06:34] That's all for this episode. Be sure to follow and subscribe to the podcast and leave a review. It really helps us out. It helps us get great guests like Derek. And, you know, it helps make sure that this is not another failed career path for me. Derek, of course, can be found at sive.rs. He's the author of four books, founder of CD Baby, and just an all-around badass. Of course, we'll be back next week with some more counterintuitive life advice. Until then, try not to get fired. Stay frosty.

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