Interviews → Influencer Economy with Ryan Williams

Derek:

I sold CD Baby in 2008 and I think, anybody listening to this, you’re going to have different phases in your life or different things that are important, right? You’re gonna have times in your life when you’re pursuing money, or times in your life where you’re pursuing skill. Say for people off and like if you’re at college or something, you’re just working just on your knowledge and your skills. Your time in college is not about making money.

You’ll have times in your life when you’re focused on romance and just being in love with somebody or finding somebody to be in love with, or whatever. You’re going to have times in your life when you’re focused on freedom or intellectual stimulation.

So I think that times change and we have to update our priorities. Often, just note, sometimes because of external circumstances like pregnancy, sometimes it’s just something runs its course, you know, like for me, making money was something that I had been very focused on from the age of, let’s say, 18 to 38. And, see yeah, so I sold CD Baby for 22 million and I had to break the habit of doing things for money because I’m not even gonna be able to spend that much in my lifetime. So sometimes it’s hard to get out of the habit of doing things for the money or to be focusing on profit, or to think of, ‘How can I make this profitable?’

It’s really hard to stop doing that after 20 years of being focused on that. So, so no I’ve already kind of made a point of not focusing on profit anymore. I do believe it’s a good secondary goal. It’s a good neutral indicator that you’re being of value to other people. People don’t open up their wallets to pay you unless you’re doing something of value to them so it’s a good way to make sure you’re being valuable to the world is make sure that you’re making money, being profitable, but as a primary focus, no. It hadn’t been a primary focus anyway.

When my girlfriend said that she was pregnant and that we were gonna have a kid, it was just nice timing for me, but I was at a time in my life when I could basically take a mini-sabbatical or retirement, or whatever you wanna call it, and just be full-time dad.

Ryan:

And how old were you when you sold CD Baby and then how old were you when you had your baby? Your actual baby.

Derek:

Well, let’s see. I sold CD Baby when I was 38. Had a kid when I was 42.

Ryan:

So you spent 20 years, you know, using the age of 18 just as a guise for thinking about money after college or thinking about getting a job after college/in college. That’s 20 years of life-living that you had under your belt focused on making money, so at that point you had reached a level where you could focus your priorities because that ending of that time, you know. You segwayed into the next part of your career. What about people that are listening, like what kind of thoughts do you have on what you’ve learned that you had to go through the ups and downs of a business, and to get to the point where you could actually prioritize your fatherhood over making money?

Derek:

Well, don’t forget you can always- you’re always in control of your life. People like to do this victim thing. Saying like, “Well no I can’t do this, and I can’t do that, and I have to do this, and I have to do that,” but somebody called me out on that years ago in a really powerful way. Back when I still had my company and I was feeling really frustrated with it, I had 85 employees, mostly reporting directly to me, and it was just, you know. 99 problems and I was complaining and complaining, and-

Ryan:

#FirstWorldProblems

Derek:

Right, exactly, and I was complaining and I said, “Well I have to do this, and I have to do that,” and he said, “Well, you don’t have to do anything.” I said, “Uhh yeah, I do. I have to pay my employees, I have to pay my taxes, I have to ship out orders when customers pay for them. I have to do this.” And he said, “No. You don’t have to do this.” I said, “Yes I do.” He said, “No hold on. I’m not gonna let this go. You need to understand this. You gotta make sure that you remember that you don’t have to do anything. If you don’t do it there are consequences, but you don’t actually have to do anything. You could right now just disappear and go to Bali and not tell anyone your phone number, and stop answering your mail, and disappear!”

He said, “There will be consequences, like when you returned the US there might- your employees would quit, your company would lose some reputation, some people would tell their credit card companies that their order was never shipped and the credit card companies would penalize you for not shipping it. There might be couple lawsuits when you get back for employees that feel you owe them money for time that they worked and you didn’t pay them, but you actually can just disappear if you don’t mind the consequences. Or if you’re willing to pay the consequences.

And he said, “You need to always make sure, no matter what happens in your life, that you know that you don’t have to do anything. You are the boss of your life at all times. Even paying taxes! Yeah the government will charge you interest and come after you to eventually pay it, but yeah! You could even skip-out on paying your taxes for 5 years if you really don’t want to for some reason, you just have to pay it eventually. Or go to jail for a while.” You know?

So I think this is a really important thing for anybody listening, that we all have the tendency to often feel trapped, you know? Trapped in a relationship, trapped in a company, trapped in a job. It’s a good reminder to know that you don’t have to do anything.

Ryan:

So when you left CD Baby, did you feel like at that point you were gonna start travelling? And that that was your next agenda item? And also, I guess diving deeper, you’re very prolific at just writing consistently and you wrote a book about your experience with CD Baby and your overall viewpoint.I guess I look at this as someone who’s creating a book and I’ve had my own businesses and I’m now 38, so I’ve lived enough life where I feel like I can express myself, and it took me a long time to get to this level (and years of therapy), but I think that for your vantage point, when did you realize?

You know, you talk about learning, you know, and in this conversation even, about what you’ve learned from prioritizing fatherhood over business and where you got to that level. But where in your life did you learn, like, “Okay, I’m okay to express myself about this”? Did you have to reach that certain level of success where you felt that was the right decision?

Derek:

Good question. You mean just about writing and sharing my message?

Ryan:

Yeah you’re consistently writing, and your blog, and your website, and even the books, and CD Baby. The book that I have, it’s that photo of you and the sand…

Derek:

No, Seth Godin actually chose that cover. It’s not me. Okay, so the original question of putting yourself out there and writing and sharing advice, I think I first felt that I could do that because I had already been a pretty successful musician, and here I was starting this online record store with a whole bunch of musicians asking me questions about how to be successful. So I thought, ‘Okay, I’m not MIck Jagger but I know a few things. I’ve made 200,000 bucks gigging, I bought my house with the money I made gigging, I can tell you how to get into the college circ, and I can tell you this. I got myself a distribution deal, I got this, like I can tell you how to do these things.

So at first it was really just me sharing very specific advice with musicians, and then people would ask me more general questions about business once I had had successful business. “How did you do that? How did you do this? How did you keep your business on track?” So it’s more just people often ask you questions. I guess it starts with that, and then I still- if I find that conversationally, if I’ve brought something up among friends, or in a conversation with a friend, or even in an interview like this, that people find very interesting, then I’ll note it and I’ll probably write about it later. Because I think, ‘Okay, that sounds like it’s useful to other people.’

Point is, the ultimate of all of this is just trying to be useful to other people. It would be very easy to lay low, keep your head down, hideout, take it easy, and not put your ass on the line by writing or producing anything and putting it out into the world, but that’s not really useful to others, you know? And I think that people lay low and then they wonder why the world isn’t rewarding them with cash, or fame, or whatever it may be, because you really have to put your ass on the line to keep putting stuff of value out into the world.

So, I’d just keep challenging myself to do that. It would be very nice and easy to just lay low, but I try to keep public, do things for the public, and in public, because it’s more use to others.

Ryan:

And you live in New Zealand, and you could reach people globally without having to leave your kitchen.

Derek:

Right, so, first let’s give a little context for that. So just a few years ago I was living in Santa Monica and I had no interest in travel because Santa Monica is fucking awesome! And I felt like I was at the end of the rainbow. Like, “This is the most amazing place in the world! I love it here!” I was so comfortable, I was so happy, I absolutely loved Santa Monica.

Ryan:

I used to live at 26 and Wilshire in Santa Monica.

Derek:

Ah I love it. Just all of it. I lived at 4th and Ocean Park. Well, 3rd and California and then 4th and Ocean Park.

Ryan:

You can’t go wrong with 3rd and California.

Derek:

Yeah. So cool. I just love that whole area. I’d sit there working all day, and then whenever I’d get a little break in my work, I would just grab my boogie board and jump into the ocean for a little bit and come back.

Yeah, so when I caught myself feeling that Santa Monica was the end of the rainbow, I realized that it violated a core value of mine which is to constantly learn and grow and to expand out of my comfort zone, right? So, when I pictured myself living in the same place for 50 years, like, “Yep, I love Santa Monica! This is where I’m gonna live until I die!” I realized that, no. In fact, what I really want out of life is the opposite. Like, ideally I would wanna live in an uncomfortable place until I’m comfortable, and then move again.

So, let me give a little example. When I was 20 years old, I moved to New York City, and, having grown up in little Hinsdale, Illinois, New York City was fucking scary! Not just because I was 20-

Ryan:

Where did you grow up?

Derek:

I grew up in Hindsdale, Illinois.

Ryan:

Okay.

Derek:

Not only was New York scary, but also it was 1990 and crime was a lot higher then. This is before the gentrification of Times Square. It was a much more dangerous place.

Ryan:

Seedy.

Derek:

It was seedy! Yeah!

Ryan:

I mean, you had Times Square with a lot of, like, strip clubs and there was no ESPN zone.

Derek:

Oh yeah! It was all, like, porno, wino, skid row, all that kinda stuff. Yeah.

So, when I first moved there at 20 it was terrifying and overwhelming, and slowly over the course of 2 years it became comfortable. Like all my friends were there, and I worked there, I worked in Midtown, and just by going to places, and parties, and gigs, I ended up walking down practically every single street in Manhattan. LIke I know every neighborhood. And within a year and a half-2 years, it became my comfort zone. So now I look at New York City and I’m just like, “Aaah New York. Aaah so good to just be back in my comfortable place,” you know? And it’s really cool that I earned that comfort! That’s not immediate comfort, that’s like growing into a new expanded self-definition and understanding of the world. That’s just a deeper happiness, right?

It’s kind of funny that we use the same word happy, whether we mean the really shallow immediate gratification or this deep, deep happiness that comes from doing something difficult and earning it, right? Okay.

So that’s my New York City example, but now imagine what scares me next. Let’s say Rio de Janeiro. Like, the idea of living in Brazil with Brazilians and having to learn Portuguese and all of the crime, and the inequality, and the outgoing, affectionate people there and that kind of very outgoing culture that kinda makes me recoil a little bit. Like, imagine living in Rio until it really feels like home. Like, you speak fluent Portuguese, all your friends are there, it’s as comfortable as any place you’ve ever lived in your life. It becomes your total comfort zone. And then you move somewhere else! Let’s say you move to Shanghai.

Ryan:

Because when we were scheduling this conversation, you were travelling for a couple weeks and months this summer.

Derek:

Yeah, so I became a legal resident of Belgium recently, so I also lived part-time in Brussels so I was in Brussels for the summer and then came back to New Zealand. Summer’s just beginning now, it’s October and the seasons are opposite down here, so October through April is a wonderful time to be in New Zealand instead of somewhere else.

Ryan:

Sounds like another rainbow like Santa Monica.

Derek:

Yep!

Ryan:

So you mentioned prior to, or actually a few moments ago about your book cover that Seth Godin helped advise you on; what type of people give you advice? And is Seth one of those people?

Derek:

Actually no, you know? I turn to books for advice. I prefer books because they’re detached and they remind me that the general advice applies to me, too. What I mean is, I think that we all tend to think that we need a personal mentor, like someone that will know all the nuances and details of our situation and can then give us advice on everything, right?

Ryan:

Well, of course. My mom is asking me about mentors all the time. It’s almost like this generation gone by that when you had a job for 30 years, you most likely had a mentor at work.

Derek:

Right, well I get lots of requests to be a mentor to people, too, and I have to say, “No, sorry.” To me, okay, if you think that you need somebody to know all of your nuances and details in order to give you advice, well, the reason they’re called details is because they’re small and they’re distracting. We get so focused on our personal details that we lose sight of the big picture.

Ryan:

Yeah, totally agree.

Derek:

I think that’s why the advice that you give others (like even when your friend asks you for advice), the advice you give others is often better than the advice you give yourself because you can’t see all of their details. You can actually see the big picture in others. You’re not confused by all of those inner conflicting thoughts that they’re having; you can look at it from the outside and see the bigger picture.

So that’s actually why I prefer my mentors to be books, because they don’t know any of my details so therefore they remind me of the big picture, and the universal truths, and they remind me to downplay my personal details. So no, I actually don’t have any mentors. Just books.

Ryan:

Yeah when I ask people for advice, sometimes mostly I get some anxiety about my details that I’m worked up about, and then people broadly can give advice, but you’re right. Books, they’re agnostic, they’re non-judgmental, they’re anecdotes are just straight up advice actions you can take. But then, what kind of books have you recently read that you could recommend people?

Derek:

Oh man! Okay, anybody listening to this, if you actually want my book recommendations, you are in luck because if you go to Sivers.org/book, you will see the last 225 books I’ve read with detailed notes and summaries and every single one of them, I’ve given a 1 to 10 rating (or maybe 0 to 10). Anyway, I’ve given them a 1 to 10 rating and if you go to Sivers.org/book my top recommendations are at the top, each one with a little explanation of why I recommend them and a link to Amazon if you wanna buy it or whatever.

This was something I’ve actually been doing for myself for years and just keeping it privately on my laptop, because every time I would read a book, I would take detailed notes on that book because I wanted to review those notes later. Instead of having to re-read the whole book, I just wanted to re-read my notes of just the most interesting bits from that book

Ryan:

So you open-source your reading catalog?

Derek:

Yeah! Exactly. So this was on my laptop for years just for myself, and I though, “You know? There’s no reason I can’t just put that out on the website.” So yeah, Sivers.org/book is tons of notes from books that I’m constantly adding every month. So those are my top recommendations.

Ryan:

And when you write a book yourself, what do you find are some topics and themes that you– well, first of all, I guess, stepping back, since you read books for advice, then do you write books for advice? To give back to people?

Derek:

Yes. Good question. I’m working on a project now, if you look at my blog you’ll see a recent blog post is called “Just Tell Me What to Do: Compressing Wisdom into Directives”.

Ryan:

Yeah I really resonate with that, actually.

Derek:

Oh thanks!

Ryan:

As someone who’s writing a book.

Derek:

Cool!

I really like this subject because I found that a lot of the books I read talk around subjects a lot, or they spend 350 pages giving you all kinds of supporting evidence, and andecdotal stories, and all kinds of arguments, but what if you already trust the source and you don’t need to hear all the damn arguments? You just want somebody to like skip all the arguments.

“Just give me the point. Tell me what to do.”

So I found that this is what would happen when I would tell some of my friends about some amazing book I had just read, right? Like, I finish a book and I’m like, “Oh my god that was awesome!” And I call my friend, and I’d say, “Al, hey! You have to read this book!” “Jeff, read this!” And my friend Jeff will say, “Dude, you know me. I’m never gonna read the book, so just tell me what to do.” And I thought that was really interesting, like he trusts me because he knows me and I know him, so he trusts me as an authority saying that if I said this book is amazing, he doesn’t need any supporting arguments. He just wants to know: What does it say he should do? What can he apply to his life? Because isn’t that really the point of everything that we’re reading for knowledge or self-improvement? We want to know what actions are we actually going to take to change something. So I’m now doing a project of going back through 7 years of 220 book notes and trying to compress them into specific advice saying, “Do this. Do that.” It’s a fun project.

Ryan:

And these are books you’ve already that were– do you think you look back that these were the right books to write at the time because you were at a certain place where maybe…

Derek:

No these were books that I’ve read in the past. I’ve only written one book; just that book “Anything You Want”.

Ryan:

Oh that’s it? I thought you had an upcoming book.

Derek:

No that’s it!

Ryan:

What?!

Derek:

I published 36 books about 16 countries in Asia– sorry, 33 books about 16 countries in Asia. Actually wait, to be fair, hold on. About 10 years ago I did do a book for musicians called “How to Call Attention to Your Music” that was more of just like an E-Book but it was never released to a publisher. It was just something that I had been sending to musicians for years.

So no, this is– I’m talking about going back through books that I’ve read.

Ryan:

Interesting because I took it as going through past books because your website itself is like a journal, and you have so many entries. I thought maybe more of those stories were published in books.

Derek:

Nope! Almost none of them.

Ryan:

Okay, because the impression I get is that you’re writing continuously and a lot of times you’ve linked to certain parts of your website. Like for example, you’re like making an IMDB for your personal book collection. I mean you totally– this is like a product here. You could have a search engine looking up a product, like, “What does Derek think about helping people?” And it’s like, “I read ‘Give and Take’ by Adam Grant and I took these three things away. You could buy it if you want, but be a giver!” Right?

Derek:

Well, I love the fact that it all can link together. Because I put this all on my site, then when I’m making some new point in the future, if I’m writing a short little lesson, I like the fact that I can keep my articles really short, succinct, punchy, something you can read in under two minutes because that’s how most people read, you know? Quickly while they’re grabbing a sandwich at work, or something, they surf the web for a little bit. They’re not gonna put aside 45 minutes to read an article online.

So I try to keep my things posted online in under two minutes and just making one point each. Then how nice to be able to link away if you want more information, like here’s an idea I’m mentioning, if you really want to dive into that subject, here’s this book. But, you know, if you don’t want to dive into that subject, that’s fine. You don’t need to. I like that.

Ryan:

Yeah I’ve reached a point with my book where it’s actions. “What can I take? What can I give to people? What can I arm people with that helps their company and gets them to a level where they can explain it more easily or grant it better?” But I think that so often you stop reading books because they are all case studies and anecdotes. It’s almost like if you could– Amazon should make a product where you can annotate books, and you can read an Ebook and annotate and actually if you choose to participate in like a GoogleDoc, you can track people’s changes to add sort of footnotes. Where people are actually like, “I did this from this advice.” Because, you know, so often with books, I’m sure (like the book you wrote), people actually take an action from it. Do you hear back from a lot of readers, actually? From your folks that have taken something that they’ve learned from you and some of the advice that you’ve put into a book, or that now you’re helping clarify from other books, like, do people reach out to you, like, “Hey, I actually took some action from what you gave me as just a piece of content.”?

Derek:

Yeah I love that! Those are my favorite emails to get. That’s so cool, because the kind of person that’s gonna read all the way through my book, or even listen all the way through this interview or whatever, those are my kind of people! You know? So I love hearing from people like that. They’re often kindreds, and I love especially when I get an email from somebody saying, you know, “Hi I live in Sri Lanka and I just read your book.” Then some day when I’m travelling in Sri Lanka, I’ll often end up meeting that person. I tend to do that when I travel; I end up meeting people that have reached out to me at some point.

In fact! The guy that’s working for me now in Brussels (I moved my book publishing company to Brussels, and my sole employee of Wood Egg, my book publishing company) is just somebody that reached out to me because he listened to an interview I did and liked it and reached out. We just got talking and he was a cool dude. I met with him in Brussels and I hired him.

Ryan:

Yeah there’s something about the online world that it’s no longer scary to meet people.

Derek:

Yeah, love that.

Ryan:

The stigma of meeting someone through a network is no longer there like it was when the internet was younger in the early 2000s.

Derek:

Yeah.

Ryan:

Which is wonderful, because it’s like the accessibility of yourself and just reaching out to people IRL (in real life for those who don’t know what IRL means), it’s remarkable. And the connections people have online are– it’s like when you meet someone face-to-face and they actually exist, there’s just something about that that’s just irreplaceable.

Derek:

Yeah, love it.

Ryan:

So when you hear from strangers, like one thing that I love about Mark Cubin, he’s an entrepreneur that owns the Dallas Mavericks, is I remember early on in his career, he says that he answers most every email he gets.

Derek:

Yeah.

Ryan:

And it could just be one word, it could be a paragraph, it could be a no thank you, but there’s something about relating to people that reach out randomly in a way that they feel like they maybe know you a little bit more because you’ve put yourself out there like you’ve talked about before. What’s it like when you respond to people and have some sort of connection with someone that you’ve never met that ultimately helps you build your team? But there’s something about that, like how do you describe that feeling?

Derek:

Well, I think it’s the most rewarding part of an email inbox; that if it’s just anonymous, if you’re just getting anonymous, cold things, then your email inbox is not a very fun place. But when it’s people that are actually reaching out, asking questions, I enjoy it.

I think the point is that everyone gets to live up to their own values, like we all have different values, right? So for example, Tim Ferris and I are similar in many ways, but he just decided early on to be inaccessible. Like you can’t reach him by design. That’s just something that he just decided was an important value to him up front, is that: Being accessible is not that valuable, and being uninterrupted is very valuable.

I know that feeling and it’s tempting and I could do that, like, I understand it. As another example, Ramit Sethi and I are similar in many ways, but he just decided to be tough. Like, he’s really kind of mean and hard on people, so people do contact him and he often kind of like lashes back at them. And I know that feeling and it’s tempting and I could do that, but he’s doing it to be helpful because he feels that people often aren’t hard enough on themselves. Or he feels that their friends are often too wishy-washy or kushy or just saying yes to everything, so he feels it important for him to be tough on people. So he’s kind of mean to people that contact him.

But ultimately, I think the public persona that works best for me is to be nice, to be accessible, and I enjoy answering people’s questions. To be fair, I don’t have email on my phone, so we all draw our boundaries where we want so I don’t let emails interrupt me, they just kind of queue up on my computer and then every couple of days I make a pot of tea and I put aside some time, and I just enjoy getting random questions from the world and putting aside time to think of them.

And sometimes they’re really inspiring. A lot of the articles I’ve posted on my site, and things that even went into the book, were inspired by people’s questions.

Ryan:

That’s great, you’re like answering– they have a problem or a question, you give them a result or an answer, and other people can learn, and obviously there’s a demand for the content already.

Derek:

Exactly! I mean, isn’t that the, you know, getting back to the business angle of that, that’s the jist of what being an entrepreneur is. Like first you need to know what the world needs. You don’t just have some vision and go out into the world and try to push your vision onto the world, ideally you make things that people are asking you to make.

Ryan:

Exactly, I love that. My book is in a GoogleDoc right now and I have 40 people who are friends or listeners of the podcast that are helping me edit it and making recommendations and telling me, “This sucks”, or, “You need an infographic here”, or, “I don’t get this part”, or, “You made a silly punctuation error”. And before I hire a professional editor, this is a much better data set of people who actually are invested in me to make a better product in the end, and it’s this whole collaborative, ongoing effort of people that think they can just create something, and that there’s this romanticized, “Oh I’ve been slaving away in my garage by myself making a podcast”, or, you know? Creating in a silo is the worst thing you can do because often times like if the old phrase, you know, “If a tree falls in the wood, does a...if a tree falls in the wood…” What am I saying here? You know the phrase!

Derek:

“If a tree falls in the forest and no one’s there to hear it, did it make a sound?”

Ryan:

Yeah! I grew up in Iowa, so I say say woods. I think forest is a difficult way for me to think, but yeah! Does it make a sound? And often times if you make something in a vacuum, you often go unnoticed because there’s no product in advance of you launching what your idea is.

Derek:

Yeah, yeah. I love it.

I did the same thing, by the way. My book, that “Anything You Want” book, I had 99 editors. I emailed a mailing list and the first 99 people that replied became editors of the book, and they all got a big thank you at the end of the book and that was really cool.

Ryan:

That’s exactly what I’m doing, totally. And it’s fun! It makes me more confident in the book so…and people feel like they have ownership, you know?

Derek:

Yeah!

Ryan:

And a lot of traditional media people I’ve told that to said, “But won’t people not buy your book because they’ve already read the book?”

Derek:

Pfft yeah! Right, those 99 people. That was your only audience, you’re in trouble anyway. You know, I really loved this book from, I think it was around 2007, there was a brilliant book called “The Wisdom of Crowds”. It is so good. THere’s a similar one, it’s called “WikiNomics”-

Ryan:

Oh yeah!

Derek:

-on the same subject, and both of them absolutely brilliant about example after example of how a collect– a diverse group of individuals is smarter than the smartest individual in the group. And even though I can say that to you right now, and you can say, “Well yes of course”, we still tend to do things that go against that fact. For example, why is it that companies often have one CEO? If we know that a diverse group of people is smarter than any one person, well than shouldn’t a diverse group of people be the CEO of a company? And why do we often have an editor? We have one editor editing the book. Why shouldn’t it be 99 people editing the book? Wouldn’t they be a better editor combined than one person? Yeah, so I love extrapulating that idea and other aspects.

Ryan:

And there’s something about building your product. You need a community of some sort, whether it’s five people or 99 people or a thousand, to make it better because if they’re your ultimate customer, you want to make them happy as much as possible.

Derek:

Yeah.

Ryan:

And moreover, giving your ideas to other people, like if I support a Kickstarter, or I help with someone’s product to give feedback to make a better tech product, I’m more likely to share that with my friends because I feel like I built it. And the more you hand over the keys to the car to help collectively get wisdom from a crowd, the better propensity it is for them to actually galvanize a group of people that, you know, want to be part of the movement.

Derek:

Right, yeah. Well put.

Ryan:

And I love it, yeah. So there’s this whole book (you’re gonna love the book), but I have to talk about your TED Talk, but only in the context of your video. It’s all about movements (I’ll put it in the descriptions if you haven’t seen it), what is the title of the video? How to Start a Movement?

Derek:

Yeah, How to Start a Movement, or Leadership Lessons Learned from a Dancing Guy.

Ryan:

Yes! So there’s a great context here because I have a chapter in my book about this guy Bernie Berns and a company called Rooster Teeth and they do Machinima videos for gamers, and they started the company 10 years ago in Austin, Texas and they’ve since crowdfunded $2.5 million to make their independent movie of their dream and they have a 20 person gamer conference in Austin, Texas called RTX for YouTube fans of games.

So Bernie was my first guest on the podcast and and in a way he gave me some social proof and credibility, and I got so many more guests because of him. He validated the podcasts and the book idea. So I saw him at this YouTube conference called VidCon where 20,000 YouTube fans and industry people from entertainment and media and the parents of these kids come into this YouTube conference and get selfies with talent. It’s an amazing carnival that I love started by Hank and John Green, and Bernie and I were talking there and he actually told me that he loved that video.

Derek:

Ah! How cool!

Ryan:

And I have a chapter about him in the book and so I asked him for, you know, why? And he said that with his Kickstarter, or I’m sorry, with his Indiegog crowdfunding campaign, he had, I think, 12,000 backers for two point something million dollars and he said those were his first followers. Those were the key catalysts. And in the end, it’s almost like that’s who his community is for, because they’re the ones that are gonna spread the message to their friends and their communities.

Derek:

Right, yeah.

Ryan:

And it resonated– he was telling me this at VidCon, and I was like, “Oh wow! That’s true!” And to hear it from that perspective, it was different because they’ve had such great success, but their true fans, these really ardent supporters,are the ones that have catalyzed and given him the legitimacy to create their movement.

Derek:

Love it.

Ryan:

So what’s it like now giving a successful TED Talk and having people like your dancing on stage at the end of the video?

Derek:

Well, okay, go back a bit. When I sold CD Baby, I thought that my grave stone would say, “He made CD Baby and that’s about it”. Like it was a little depressing. Selling your company is a weird thing. It’s a little bit like graduating college and getting a divorce at the same time, you know. People congratulate you but there’s something kind of sad about it, you know?

I really felt like, wow, that was such a huge success that I think I’ve peaked! It’s a weird feeling that I think most of us will get at some point in life. When you admit that your biggest success is behind you. That was it. You will probably never get that successful again.

Ryan:

For some people that’s crisis inducing.

Derek:

Yeah, well it was kind of for me. I was kind of depressed, I wanted to disappear. A lot of it was actually triggered by the fact that, like I mentioned earlier, I had 85 employees that were mostlyl all directly reporting to me, and things got really nasty in the last year. Like, my employees just decided that they wanted to take the company in a different direction than me and just decided that I was the cause of all of their problems, and just focused all of their anger on me, and it was really, really tough.

So once I sold the company, I just wanted to disappear. Like I seriously looked into legally changing my name and disappearing and just going off the grid and being gone. I thought I would just take my money, and lay-low, and do some open source programming until I die. But then because I had only ever been in music, when I was watching TED Talks, I would get really inspired and I wanted to be in that crowd. I went, “Wow, that would be so cool to be surrounded by intellectual writers and achievers.” So I made it a goal of mine to get invited to speak at TED, and I mean the real TED.

Ryan:

That’s like the thing of the TED Talk, right? Is there’s something about them that you want to be in that crowd.

Derek:

Yeah…

Ryan:

I mean, they did a remarkable job of branding themselves as this intellectual elite that everyone, in some way, either can’t stand or wants to join. There’s no middle ground.

Derek:

Right, but for me it’s like I don’t really watch TED Talks anymore. I haven’t really watched any since 2009 I guess, but at the time, like in 2008 right as I was selling my company, to me this was really aspirational. Like I watched this and just as you said, I wanted to be a part of this crowd. So I threw myself into it. This was a good goal for me. For the first time in a year or so I wasn’t depressed or wanting to disappear, I suddenly wanted to step-up and take responsibility for my existing fame and perhaps even get more famous and be more public. Again, like you asked about earlier at the beginning of the call, doing things publicly, putting your ass on the line, and writing articles instead of laying low, you know?

So I worked for six hours a day on writing short, punchy, surprising, intellectually stimulating articles, and I applied to TED multiple times and I finally got in! Not just once, but at three different TED conferences in a row. ANd this was before TEDX, so these weren’t TEDX conferences.

Ryan:

So these were the big leagues.

Derek:

The big big, like there’s Al Gore sitting in the front row in front of me, you know?

So I did these TED Talks, and now what’s funny is that more people know me from my TED Talks than they do from CD Baby, and then in fact, for a few years after TED one of the most common questions I would get from people is, ,”So what did you do before TED?”

To me that was like this wonderful feeling! YOu know? It’s so cice to know that we can change our career. Like here I thought I had peaked, and it’s like, “Wow! I did it! I made a change!” And so I think it was really encouraging to know that we can always find a path that goes up.

Ryan:

But you spent several time focused on that goal…

Derek:

Yeah of course! Any worthy reward takes work, you knkow. ANd yeah, it wasn’t just luck.

Ryan:

What was your answer to that question about what you did before TED?

Derek:

Oh! I just, “Yeah I had a company called CD Baby,” And they’d say, “Oh, CD what?” Yeah, nobody had heard of it. I get that a lot now, too. In those circles I was in 10 years ago, it felt like CD Baby was a big deal. Now in hindsight I feel like almost nobody I know has ever heard of it.

Ryan:

Did the TED Talk take your career in a different direction? That you reinvented part of what you were doing and creating beforehand?

Derek:

Well it could have, I mean literally in the hour after I had got off stage, after delivering that talk about “The First Follower: Leadership Lessons from a Dancing Guy”, I had like five different agents come up to me at the conference saying, “Oh my god, we’ll sign you to a book deal right now.” Or, “Hey, we’d like to represent you in the corporate speaking circuit,” you know, “ We think this would be a great talk for you to deliver to these Fortune 500 companies”.

So I could’ve taken my career that direction. I could’ve gone and been a public speaker for companies talking about leadership, and I could’ve written a book called “The First Follower: Lessons Learned From a Dancing Guy”, you know? I could’ve gone that path, but I looked at it and it just wasn’t appealing. I just don’t have that much to say about leadership. It was just a three minute talk, you know? I’m no leadership expert, I just made an entertaining three minute talk, so.

I’ve said thank you but no to all those people that wanted me to speak at their companies and all that and, yeah. Instead I was more inspired by the stuff we talked about earlier, about travelling the world, seeing the world from a different point of view and feeling somewhat retired. Like, say for example the only reason you would fly off to Minnesota to speak at some pharmaceutical company about leadership, you’d be doing it for the money, right? Unless you really wanted to see Minnesota.

Ryan:

Yeah it’s a money grab.

Derek:

Right, so, like we talked about at the very beginning of the call, I had to remind myself that I’m not doing anything for the money anymore. It would be completely irrational and stupid to do something for the money since I’ve got more than I’m gonna spend. So yeah, the idea of speaking at corporations; no price could get me to do it.

Ryan:

But you said a bit earlier in this TED context that you at one point wanted to maybe become more well known in your industry. What was…

Derek:

Right, so the writing to me is the better way to do that. I love the fact– it makes me deeply happy when, say for example, I’d go onto Twitter a couple times a week and I’d search for mentions, you know the @Sivers (my twitter handle). and I’d see who’s mentioning me and it’s so nice to see when people referencing an article I’ve written, or two different people are telling each other about it, like, “Hey dude, you need to read this article”. And somebody says, “Oh if you think that, you should read this article by Derek Sivers,” and that’s a really nice feeling! To be a part of the conversation that’s going on out there, you know?

That, to me, that’s more success to me than making a hundred grand speaking at Fortune 500 companies, you know?

Ryan:

And so then, you feel like in the context of the internet when you get someone sharing and tweeting out @Sivers, what kind of feeling do you get without thinking you’re narcissistic? Or, like, how do you stay grounded?

Derek:

Okay actually, okay.

Ryan:

If a TED Talk isn’t enough, you know, because I think that’s a peak. Especially in that context of the era where you did that TED talk.

Derek:

Yes, yeah.

Ryan:

Because now the TEDX have almost franchised out the model, so the barrier to entry is a lot lower and it was a very big deal, and was that a TED Talk that was up in Northern California?

Derek:

Yeah that was at their main... well, actually it was when they moved it to Long Beach, but yeah it was at the big, giant–

Ryan:

But even Long Beach, that was, like, you know, celebrities were starting to go there and people like Robin Williams would to show up.

Derek:

Yep! Oh dude that’s what was so nerve– like, I may seem calm on stage (like when you watch the video), but inside, man, I was having a heart attack! RIght in front of me– right there in the first 10 rows, I mean, there’s Bill Gates, there’s Al Gore, there’s the dude that invented UNIX, there’s two founders of Google, there’s all the movie stars, intellectuals, and Nobel Prize winners are sitting there watching me give my talk, you know, better be fucking good!

It was the ultimate pressure, man, it was terrifying. But anyway, so yeah, so you’re saying I’ve peaked again? Is that what you’re trying to say?

Ryan:

Well I’m saying, yeah! I’m wondering, how do you embrace yourself as a creator without getting too far ahead of yourself or– because often times I work in the startup world. I’ve done– I’ve had a lot of CEOs and executives that, to use a Biggy Smalls quote (that I don’t ever quote): Never get high on your own supply.

Derek:

Right, okay.

Ryan:

How do you not do that? Or maybe you do, but–

Derek:

Okay something...something happened to me in 2007 that was really tragic but useful. It’s that it was in the tech world, I had switched my programming technology from PHP to Ruby on Rails in 2004, and I was one of the first guys to switch to this new technology called Ruby on Rails and I did it very loudly so a lot of people held me up as an example of why their company should use Ruby on Rails.

And then in 2007, I very quietly admitted that I gave up on Ruby on Rails after two-and-a-half years and switched back to PHP. And a few people asked me why, and I kept answering them by email, so finally on the quiet little blog that I had that nobody ever read (it was on a tech site called OReilly.com), I had a little quiet tech blog where I would talk about SQL commands and stuff like that, I said, “Here’s the 7 reasons why I switched back to PHP after two years with Ruby on Rails”. And it was actually literally on my birthday. I posted it at night on my birthday after I got home from dinner with a friend, I posted that article and I went to sleep.

And, Ryan, when I woke up in the morning, there were hundreds and hundreds of comments calling me the biggest idiot in the world, it made top-page news in all of these tech sites where all of my peers and people that I admire read. And here I am, top-page news being held up as a raging idiot for, you know, “What an idiot to do this stupid thing, and obviously this guy is a stupid asshole. People like him are the problem with the world.” And all these scathing comments, and just hundreds of comments saying all of these things about me.

Ryan:

Because you switched back to PHP?

Derek:

What?

Ryan:

Why did they get mad at you, then?

Derek:

It’s a little bit like religion. In the programming world, if you insult somebody’s programming language–

Ryan:

Because you sold out?

Derek:

No it was more like, just people have their favorite programming language and they think that theirs is the best and the other ones suck. So if you say that you’re using a different one than them, or that you’ve decided not to use the one they’re using, it’s like you’ve just said that Christianity sucks, you know? You’re gonna get people upset.

Ryan:

So it’s like gangster mentality? Like, PC Vs. Mac, or people that take their Android phone a little too seriously Vs. an Apple device.

Derek:

Right, so for the first couple minutes, I was upset, but then almost right away something snapped in me where I said, “You know what, all these people saying all of these negative things about me, they have no idea who I am. They don’t know my context, they don’t know the real me, they’re just responding to something that has to do with them. This actually isn’t about me at all.” In fact, if I were to make a visual representation, it was like they were attacking some sort of cardboard cutout cartoon of me over here. That’s not the real me.

And so, that was the day, man. The day after my birthday in 2007 that I disconnected from my public persona. Now anything I do publicly is not the real me. Even if it’s whether people are saying mean things or nice things, I feel like everybody’s talking about this cardboard cutout over here.

Like, the public you is not the real you. You’re showing one side of yourself to the world, and people that are responding to it don’t know the real you, they’re just responding to the bit of content, you know, words or music or something that you’ve put into the world. They’re just responding to that. Not to you as a person.

So, no I don’t believe– I don’t take to heart any of the praise or criticism

Ryan:

So is this why you do less talks or interviews? Because you’re just trying to keep your sanity to the internet you VS. the real you?

Derek:

That’s more just a matter of time because I’m not pitching anything. The main reason that people do interviews is to pitch something or they want to be more famous. like I don’t want to be more famous and I’m not pitching anything, so the main reason I do interviews is honestly I just like the challenge of getting difficult and challenging questions which makes me think of things that I ordinarily wouldn’t unless somebody asked me a difficult or interesting question. So yeah, that’s the main reason I do them.

Most of the time I’m just lost in my work, I’m not very conversational, so. Yeah that’s the main reason. It’s not really having to do with the public criticism, but no. To answer your question about, like no, when I search, you brought this up because I mentioned searching @Sivers on Twitter.

Ryan:

Well everyone does it!

Derek:

Yeah!

Ryan:

It’s why we use media, like social media, as in likes, and favorites, and @ replies.

Derek:

Yeah, so it’s nice to see, and also comments (all that I just said, by the way– I think what’s really useful by the way, is when you post one idea at a time on your blog), it’s really nice to see the comments where people might have misunderstood it. So say for example the thing we talked about earlier of me trying to compress the wisdom I’ve learned from the last 225 books I’ve read, how to compress those into advice and directive for others. When you read the article about that and you look at the comments below, it turns out that everyone thought I was talking about doing cliffnotes. They thought I was going to compress each book into a succinct version of that book.

And I realized that I had been completely misunderstood, so something in the way I described it must have been wrong. It was my fault that I must’ve described it wrong because I never intended to compress individual books, I just meant how can I take everything I’ve learned in the last eight years and turn it into advice.

So I think comments can be very useful to let you know when you’re not being clear.

Ryan:

And so what (just talking about books and content), what are you watching on TV now? Do you watch much TV?

Derek:

Oh I haven’t since I was 18, no. Dude I never watch anything! I’ve actually never listened to a podcast, I haven’t watched a TED Talk since 2009, I haven’t seen any TV shows that I hear about. I just realized recently, somebody asked me, “Oh have you watched this TED Talk? Have you seen this movie? Did you see this TV show?” I had to think about it for a minute, and I realized I don’t watch anything! I don’t watch videos. I don’t listen to anything, I don’t watch anything, I just spend all of my time reading and writing and hanging out with my kid,

Ryan:

And so, with your friends, then, what do you talk about? Because that’s all I talk about with my friends.

Derek:

TV?!

Ryan:

No not TV! But what I’m reading is a big part of it, but the TV is a great shared community thing with your friends or your people. Like my wife, essentially. I don’t know what we’d do after 8 PM when our kid goes to sleep if we didn’t have, you know, Justified or Orange is the New Black.

Derek:

Funny! I think most of my friends right now are talking about, god we actually just end up talking about like personal romance. Everybody I know is like single and dating and sharing their stories and their heartbreaks, and that stuff, or we talk about career stuff, or just life. I don’t know. It’s like Seinfeld, you just talk about life.

Ryan:

Yeah, just you’re catching yourself and whatnot. I’m actually–

Derek:

You see what I just did there? I made a TV reference! You proud of me?

Ryan:

Yeah, I think that was really subtle. I didn’t even pick up on it. Because I thought, you know, you watched TV in the era when Seinfeld was on.

Derek:

Actually our mutual friend Meredith and I used to watch Seinfeld every night at 11 when it was in syndication. We both lived in New York City and every night it was on from 111 to 11:30, we’d watch it at 11 and then call each other at 11:30 to talk about it.

Ryan:

Back when there was a thing called a water cooler at work, and there was nothing called social. Media.

So I have a few couple more questions and then we’ll wrap, but I had a guy, a friend, who listens to the show, and he said he met you in Singapore and he was doing something called Mopex and then he ended up– he bought Film Baby from CD Baby and just randomly he emailed me that. But his question was, what type of stuff have you learned through your professional of working at CD Baby through 38 that you feel like you’re hoping to instill in you child? He’s a recent father and that’s why he’s asking.

Derek:

Ooo wow.

Ryan:

It’s deep.

Derek:

But first, by the way you know what’s funny? I was actually a part owner of Film Baby, and nobody ever– because I never talked to the, because we had bad blood, I never heard from the old people so, I was actually owed some money from a FIlm Baby sale. Nobody ever reached out to me.

Ryan:

Well, he said he never emailed you to tell you that because he thought it was funny because he had met you randomly in Singapore, and he said, “You know, I wanted to always follow-up with him and tell him that I bought Film Baby.”

Derek:

Well tell him to email now, I guess he’s probably listening.

Okay so, what did I learn from– I think the only parenting thing I’ve learned so far is about being undistracted, right? Like if I would have tried to have a kid 10 years ago when I was in the middle of running my company I would have been a terrible dad, but I love the fact that I’m just in this phase of my life where I can just– every time I’m with him, I just completely shut everything off. Phone is off, computer’s off. I don’t just put it to sleep, I shut it down. I power down and no clocks, no schedule, I just don’t even bring the phone with me, I don’t want to know what time it is. The time is whatever he tells me it is, you know? If he says it’s time to eat, then it’s time to eat. If he says it’s time to go to sleep, then it’s time to go to sleep, but not until then, you know? So I don’t do this thing of trying to force a kid into the hour hand on the clock schedule that is kind of more of an adult construction, you know. I think that’s, to me, the biggest friction I’ve heard is the hardest part about parenting is when they’re trying to force their kids into an adult schedule. So, I mean granted my kid is three, so.

Ryan:

Like, “Oh, it’s 8 o’clock. Time for bed.”

Derek:

Right.

Ryan:

“Why?” “Because it’s 8 and I said so.”

Derek:

Right! Yeah, I don’t do that.

Ryan:

It’s what we do!

Derek:

I don’t think lessons learned from running CD Baby apply to parenting at all. I haven’t found any crossover there at all.

Ryan:

Would you want your son to be either a musician or an entrepreneur?

Derek:

I have no expectations for him at all. He could be a ballerina or a gravedigger for all I care. Whatever he wants to do is fine with me. That’s totally up to him. I have no expectations for that.

Ryan:

And that’s like a good parent. That’s a trick question, I was seeing if you’re– no.

Derek:

Oh! Thank you.

Ryan:

And then the final question is when, you know, you look at where you are in your early 40s and where you started out with CD Baby, or in college, or in New York City watching Seinfeld with Meredith, or calling her afterwards…it sounds like you’ve reached a lot of different journeys that have taken you starting things and closing them out. Do you think that’s important for people? Where you start a company, you sell it, you move on, you travel, you end your trip, you move to New Zealand, and you’re living this phase of your life. Like you seem to have a very philosophical viewpoint of the phasing of life.

Do you think that it’s important for people to look at themselves in smaller chunks Vs. trying to think where they wanna go in 20 years and where they wanna be?

Derek:

No, I try not to be prescriptive with this stuff. And if you’re asking me questions about me, I’ll say, “This is me, this is my preference”, but I’m not saying that anybody else should. It’s more about being honest about what really works for you. Like noticing when you’re thriving, when you’re at your best, when you’re happiest, and noticing what drains you.

So for example, I call this The Compass in Your Gut. I think that there’s like a compass in your gut that points to directions: Is this exciting me? Or is this draining me? If something is draining your energy, you need to stop doing that thing right away because nothing’s worth that, you know? I saw that so many times in the music business that musicians would get into music because they loved, say playing the drums for example, they loved playing the drums, this is their big love, and somebody said, “Well, you know, if you’re gonna get into the music business you need to read this book about contract negotiation, and you need to read this book written by this lawyer about how to negotiate a record contract, and you need to understand cross-collateralization and royalty agreements,” And pretty soon this person has lost all interest in playing drums because he said, “Ah, never mind”. You know?

So, I think we we each need to be honest about what works for us, so a friend of mine, same age, grew up in the same place, we have almost the exact same upbringing, but she just wants to stay in one place her whole life. She bought a house about 8 years ago and she has said many times, and so has her husband, that this is the house they’re gonna die in.. This is it. They are done. They are never moving; this is their place. And she just wants to stay in one place her whole life, she has no interest in travel, and I don’t know. Even when I tell her the amazing things about Asia she just rolls her eyes and like, “I have no interest in ever going there.” She has no interest in ever travelling, doesn’t want to, just–

And so, I’m not gonna say that somebody like that should start thinking of their life in short little chunks and making lots of changes because nope. She just wants to do one thing until she dies and stay in one place and that’s just her.

So yeah, other people find their calling and they just wanna do that for their whole life. They wanna just keep deepening their passions, say, you know, Stephen King writing novels. He’s just lived in Maine and continued to write novels and novels and novels his whole life. He doesn’t switch gears, unless you count each novel as switching gears in a minor way, but okay, so the point is you just need to pay attention to what works best for you.

So some people just want to do one thing for their whole life, I think of Stephen King writing novels his whole life, and other people. I actually really like the musician comparison. If you look at some music careers, like look at AC/DC Vs. David Bowie, right? Like AC/DC has done the exact same thing since 1974 and David Bowie, for example, has been doing very different things since then. He’ll do industrial for a while, now he’s Ziggy Stardust, now he’s this kind of blonde-haired soul singer, and now he’s this, and I think for me, I just gravitated towards that approach. I just like the challenge of changing things up, but to each his own.

Ryan:

So do you think– my final question is, then, talking about putting yourself out there and creating content like your writing on the web, for example, I have a podcast. And some people feel like that’s what they wanna do to challenge themselves, others feel like it’s not part of their routine so they don’t need to do so. But do you think in this era, since everyone is using online media in some capacity to publish their ideas, that people need to do that? And not just a flat yes or now, but you have to put yourself out there on the line now in the business world.

Derek:

Well if you’re not on the line, it’s like you don’t exist.

Ryan:

Yeah.

Derek:

You know, there’s a great book called “Show Your Work” by Austin Kleon that– people often talk about networking, like going to networking parties and meeting people– instead, how about you just use the network? Like, “Show Your Work” online, share what you’re focused on, share your work on the network. Meaning the net, the internet. That’s the network. That’s where your work reaches out.

So yeah, I do think that a lot of people have a resistance to that idea because it’s scary to put your ass on the line and put yourself out there for criticism, but ultimately you have to ask yourself this question: What’s more useful to other people? Is it more useful to be hiding in my bedroom and not sharing what I’m doing? Or is it more useful for me to be putting everything out there in the public? And you know the answer.

Ryan:

Yeah absolutely. Uh, hide! No...do-don’t hide. Um, get out of the closet and start publishing stuff!

Derek:

Yeah

Ryan:

Cool! Thanks for coming on.