Derek Sivers

Interviews → Disruptive Entrepreneur / Rob Moore

Fun questions. Ideas versus execution, why business is about being generous, amplifying your niche, my one wish for everyone on the Internet.

Date: 2020-05

Download: mp3



Hello and welcome to the Disruptive Entrepreneur podcast. The guest on the show today is none other than CD Baby founder, Derek Sivers.

Derek is most known for being the founder of CD Baby. CD Baby was the largest online distributors of independent music. In 2008, Derek sold the company for about 22 million dollars. In this interview, Derek goes into detail about how he accidentally created CD Baby, grew it, and sold it for 22 million dollars.

This is a really diverse and really open conversation. Derek’s got some really powerful insights into dealing with rejection and how to develop your confidence. We talk about relationships. Derek talks about how he got onto tech talks and public speaking skills. There’s a lot of discussion about entrepreneur traits and what makes a great leader.

Let’s get straight into the interview with CD Baby founder, Derek Sivers.

Hello, everyone. I am privileged, excited, and slightly nervous. Derek, you are the person who has rejected me the most for an interview [laughter]. I think it was five or six times.

I’d love to ask you straight off the bat, why did you reject me so many times and then decide to come on this show?


I did an interview with Tim Ferriss, who’s an old friend of mine, and I didn’t realize his podcast was so famous. I gave my email address on the air and over 8,000 people emailed me over the next couple months and it became a full-time job. In fact, I had to hire an assistant just to help me triage all these emails. It was a full-time, 12-hour day job for a couple months just to answer the emails from that one podcast.

After that interview, I decided I wouldn’t do any more podcasts for a while. That was enough. For five years, I didn’t do a single interview. When anyone asked me, I said “no” – no matter how famous they were. A few months ago, I felt ready to start doing them again. Nothing to do with the Corona stuff. It was a few months before that.

Now I’ve built the interviews into my schedule and I’ve got a nice camera and microphone setup. It’s easy for me to step over here and hit record. That’s why it was nothing personal. I said “no” to absolutely everybody for five years.


That’s how I found you, actually. I listened to that Tim Ferriss episode and I was one of those 8,000 people that reached out.


I love that! It was worth it to me.

It wasn’t a mistake. I think it was wonderful because I met 8,000 people because of it, including two women that later became girlfriends and great loves. I was just talking with one of them an hour ago. All random connections just because I gave out my email address. No regrets at all. I think it’s wonderful.


That’s the magic of podcasts and people like you, Derek. I’d like to put myself in the same category. I will reply to every single person’s email and I will give my email out, even in a place where you might get inundated. I like meeting new people. There’s mystery and beauty in that. Everyone else is doing the opposite and they say, “Speak to my agent.”

Whenever I reached out to you, you replied back. We had dialogue. Even when you rejected me, you rejected me politely. I’ll always remember that. When people reject me politely, I have to try again and again. We bonded over certain topics. You moved to England and I’m really into Radiohead. We kept a little dialogue going.


Here’s another lesson in that story: persistence is polite. This is a counterintuitive lesson that’s hard to learn because when we’re teenagers and we have a crush on somebody that doesn’t have a crush back, we learn that persistence is inconsiderate and thoughtless. Persistence means that you’re not taking a clue.

In business, persistence is polite. The alternative is to contact somebody once, and if you don’t get what you want, then you give up and curse them and say bad things about them for years to come. Instead, if you understand that a rejection is nothing personal at all and has nothing to do with you, it’s just their current situation, then that’s actually very thoughtful and polite of you to politely persist.


That’s very true. There were a few reasons I kept reaching out. To be clear, I didn’t hound you. I checked in every six months to a year. First off, the interview with you and Tim lasted for about two hours. I felt like I really knew you after that interview, which I know is crazy. That’s the intimacy of a podcast. I really liked you. You had some very alternative and thought-provoking ideas that stuck with me.

Secondly, I’m sorry if this sounds like a man crush, but I’m an honest guy, you’ve got this beautiful, deep, warm voice [laughter].


Thank you!


I know you received 8,000 emails, but I bet many of those people felt a real connection with you after Tim’s interview.


That’s why if somebody looks over my shoulder when I’m in my inbox, they’ll say, “God, these total strangers are pouring out their heart to you. What the hell?”

I say, “No, I get it, because they just listened to me for two hours. For them to email me a mere four paragraphs is understandable.”

It’s a conversational human reciprocation. If somebody was speaking at you for two hours, of course you’d share something back in return for all this person just shared. It’s totally understandable. In fact, I think it’s usually wonderful. Every now and then there’s one out of a thousand that indulges a little too much and inconsiderately starts to project stuff on to me. But those situations are so, so rare. People think they’re more common, but it’s really rare.

I’m glad I’m not as famous as Tim. Total strangers don’t project onto me that much. I’ve met some amazing people from around the world – not just romances. If I’ve emailed with someone from Mozambique a few times and they pass through where I live, sometimes we’ll meet up in person. How cool is that? I actually get a great sense of security from all the cool people I’ve met around the world.


So you’re saying you had two partners because of Tim Ferris’s podcast? [Laughter].


Yeah. Two and a half. The woman I spoke with an hour ago, we’re just your friends now, but she emailed me the day after the interview went on the air. She listened to it while walking around Prague one day and I ended up checking out my other stuff. She sent me this long email and I thought, “Wow. She’s an amazing person. Absolutely brilliant.”

She’s a scientist in Sydney with an amazing background. We emailed a few times and I said, “I want to know you. You’re a really, really interesting person. What’s your phone number?”

We started talking every day on the phone and one thing led to another.

How you meet somebody is not that important. Especially in today’s day and age where so many people meet on Tinder. I think it’s actually much cooler to meet people that find you because you’re putting yourself out there. If somebody was a painter who constantly put their work out there, you’d be more likely to want to meet a person that falls in love with your work, instead of a random stranger at the pub.

It becomes a natural filter if somebody is moved by your art, or writing, or anything you’ve put out there into the world. That’s a part of your soul. And if they’ve already been drawn to that, that’s a much better start than, “Hey, you’re hot after a couple beers.”


What would you say you’re most known for, or what would you like to be most known for?


It’s not just one thing. That’s my real answer.

Because in 2008, I would have clearly said that I’m only known for CD Baby and that’s probably all I will ever be known for. That was a really sad thought to me. When I sold CD Baby, I was afraid I had peaked and that my best was behind me. My gravestone would say “He did CD Baby and nothing since.”

In 2009, I was inspired to become a TED speaker, writer, author kind of guy. And I did it. I nailed it. I spoke at the mainstage TED conference three times in one year. By 2011, everybody I met only knew me through TED. People asked me, “So what did you do before, TED?”

I thought, “Yes! I made it past the CD Baby phase.”

In 2011, my book, Anything You Want, came out and a lot of people only knew me through my writing. They didn’t know that I ever spoke at TED or created CD Baby.

I’d say I’m known for those three things. It’s my writing, my speaking, and then the music company I started long ago.


After selling CD Baby, why did you think that was going to be it?


I’m not money ambitious.

I’m not the kind of person that would say, “Drop me anywhere on Earth with a dollar in my hand and I’ll turn it into a million within a year.”

I’m not that guy because I don’t care that much. I’m ambitious in my ideas, but not in my bank account. CD Baby got successful through smart luck, and being in the right place at the right time. It was definitely really good timing. I started CD Baby at the beginning of the first dot com boom and got out a month before the financial collapse of 2008.

I will probably never create something that big again. But if my articles, and books, and writings spread, that’d be cool. But I don’t think I’m ever going to start a company like that again. But at the time, I was in the entrepreneur mindset that a company is how you leave your mark on the world.


How did you end up speaking at the TED conference three times in one year?


Very deliberately. I spent about a year feeling very lost after I sold CD Baby. At the time, I was watching a lot of TED talks.

I don’t anymore. But at the time, I was really into it. Suddenly, I got this flash of inspiration and thought, “I want to be one of those people! I want the TED conference to invite me to speak.”

Very deliberately and methodically, I wrote something radically interesting every single day so that I could pitch a bunch of different ideas to the TED conference. It was a very deliberate process and I was thrilled that it worked.


You said that you spent a couple of hours preparing for this interview, which I’m flattered by, although it’s not about me, it’s about you. I did the most research for this interview than I’ve ever done with any guest. Because if I’m going to ask you to be on my show five times, I should do some bloody work! [Laughter].

You also asked for my questions in advance, which a lot of my guests don’t do. I thought that if you’re going to prepare, I should prepare, too. I watched as much of your content as I could find.

I find some of your ideas fascinating. As someone who has built my own business and probably learned from the more traditional success classes, you challenge many of those ideas and I really like that.

You’re almost like the anti-success, anti-business, anti-personal development type of person that leads people to success in business and personal development in a weird way.


By the way, that’s intentional, too. I realized that TED talks are only interesting if they surprise you. No matter how emotional they may be, if they share stuff that you already know, or especially if they only tell you their own life story, it’s not interesting. You don’t remember those.

The ones you remember are the ones that make you go, “Huh? That’s weird. That’s completely opposite of what I would have thought. That upends my expectations on this thing.”

So, I try to only release content into the world that is surprising.

If you tell somebody what they already know, then it might help motivate them a tiny bit, but it’s not that interesting.


I’d love your take on how leadership is often over-glorified. Can you share?


Sure. This is from my TED talk called First Follower. It’s a video of a shirtless guy dancing. He gets all the credit for starting this movement of dancers, but if you watch closely, it’s the first guy that followed him that really got everybody else to follow.

Until then, he was just a weirdo dancing and you didn’t really want to follow him. It wasn’t till one person had the guts to imitate him.

Then that person made it cool. Everybody likes the story of a single person taking all the credit. When you say, “No, no, no, it wasn’t me. It was the team.”

Rationally, we say, “OK. I’m sure it took more than this one person.” But on a more instinctual, gut, emotional level, we still think it’s the one person that gets the credit.

A charismatic leader with a bad team will fail, but an uncharismatic leader with a great team is more likely to succeed. To me, it’s proof that leadership is over-glorified because it makes for a more interesting story. But the truth is, it’s the team that makes things happen.


I remember you emphasizing the courage of that second person. Because the first guy is already crazy, but the second one – he’s got something to lose.


Somebody has to make it easy to follow. The first follower shows everybody else how to follow. And if you’re somebody listening to this and you’re the lone nut that wants to pioneer something, but you want people to start following you and contributing, I think the best thing you can do is to make yourself easy to follow.

Take the time to make clear instructions on how to join and how to contribute. Make it appealing and fun. Most importantly, try to develop a system from the beginning where your followers can become leaders themselves, so that the new followers are actually following your followers instead of just following you.


I find that fascinating because like you said, when people give credit to the team, that’s just lip service, isn’t it?


Yes. It’s a difference between head and heart. In our heads we can say, “I know Elon Musk isn’t sitting there making all those cars himself. He didn’t invent everything. I know Steve Jobs himself didn’t invent the iPhone.”

We know that rationally. But our heart still associates Steve Jobs with the iPhone and Tesla with Elon Musk.

We still think it’s one person emotionally, even if we don’t think it rationally.


Something I’ve always struggled with most of my life is the fear of being disliked, ridiculed, not valued, unnoticed, embarrassed, shamed, bullied. I used to be really overweight as a kid. Those demons are still there, but I believe my courage to face them has gotten stronger.

What are your thoughts on having the courage to be disliked? Do you have strategies to cope?


It’s about developing a stance to amplify your quirks instead of downplaying them. Set yourself apart from the crowd at every step.

For example, if you don’t like meeting with people, then move to the middle of nowhere, loudly announce that you don’t meet with anyone for any reason. Amplify that preference. You’ll attract those that wish that they could or would do the same.

You should express your quirks at every stage of the way, like your communication with clients and the way that you email people. Your website should also reflect your quirky personality – not just a template from WordPress.

I was in the music business for ten years and I’d come across these hardcore musicians. They could be hardcore in any way, like a country speed punk metal band. I loved that when you first meet these characters that are part of a speed punk band, they don’t say [nerd voice], “Oh hello Mr. Sivers. I’m calling to get my band on your service.”

No, they say, “Hey what’s up motherfucker! We’ve got this album. It’s gonna rip your balls off, man. We want to get this thing distributed through you. How do we do it, motherfucker?”

They weren’t trying to please anyone. They were loudly being who they are. In fact, that’s deeper branding. They went all the way instead of trying to be generic. We could all could take a lesson from that. Take some extreme niche and go all the way with it.

Imagine you’re a dentist in a small town and you announce that you’re only seeing patients by referral of a quality customer. Even that one little move would put you into this high luxury category.

Maybe you want to be the most mysterious or the most ridiculous. Whatever your niche may be, amplify it.

Another great example is Cards Against Humanity. It’s a party card game. Look up their annual Black Friday promotions. Every year, they do the most ridiculously hilarious things like digging ditches and dumping money into them.

They have such an amazing, creative statement behind them. Right off the bat, their brand says, “No, we’re not just an average Mattel board game. We’re not trying to please everybody. We’re taking a niche.”

If I could be any company today, I would be Cards Against Humanity. I love what they’re doing. But your real question was about the courage to be ridiculed. I think that if you do the type of things I just mentioned, then when somebody ridicules you or makes fun of you, you realize that you’re doing something right.

If you loudly proclaim that you are the most expensive and somebody says, “Get off your high horse.”

You can say, “That’s what I want. I want you to scoff at how expensive I am because that means my niche is being communicated.”

If you go to, my website is very, very plain on purpose. I don’t use any templates or frameworks. I wrote every line of HTML by hand. I don’t stick in a single line that doesn’t need to be there. It is plain and fast and minimal. And that’s my thing.

Same with the way that I write. It’s my niche. About once a month, I get an email usually from a web designer who says, “Oh, God, your site is so ugly. Come on, let me let me design you a better site.”

I go and look at their site, and it’s some typical WordPress template. I say, “No, thank you. The fact that you called my suit site ugly means I’m doing something right.”


How do you not take things personally?


For one, you have to know that the public you is not you. If I could wish one thing for everybody on the Internet, it would be that everyone would have a stage name. Not a single human on earth would use their real name on the Internet.

So, if somebody is criticizing Tracey Rainbows for her ridiculous marketing campaign, Tracey knows that they’re only attacking her avatar/stage name that she put out there.

For example, if somebody criticizes Bono, he knows that they’re criticizing the public persona that he’s put out there – the Rockstar persona. We all have our own version of this.

What Rob Moore puts out into the world is not the whole and complete person of yourself. You put out an aspect of yourself into the world. If somebody attacks that well, that’s not you. That’s a cardboard cutout of you that they’re throwing tomatoes at.

The real you is at home with your family. The public you is not you.

About 13 years ago, I wrote an article that was very, very unpopular and everybody attacked it. I realized that all these people attacking it didn’t know me at all. In that moment, I cut the connection between my public self and my real self. I completely disconnected.

But this also means that if the public you is not you, then you can’t take credit for the praise either. When somebody praises you, they’re praising your public persona, not the real you.

In hindsight, I wish I would have made a stage name, but it’s too late now.

For anybody who hasn’t put themselves out into the world too much yet, I highly recommend making a stage name. Not a ridiculous Tracy Rainbow name like the one I just made up [laughter]. Pick something that’s believable where people might think it’s your real name, but you’ll know that that’s not the real you. It’s one of the best things you can do.


I’ve never heard that analogy. I’ve heard people say, “Don’t think take things personally. They don’t know the real you.” But the way you just explained it is brilliant.

It’s easier to do that when you’ve got a moniker or alter ego. What article did you write 13 years ago article that was so unpopular?


I switched from the PHP programming language to Ruby on Rails for two years. And after two years of trying to make Ruby on Rails do what I wanted, I switched back to PHP. I was a guest blogger on somebody else’s technical site. I wrote a little article for an audience of nobody about the seven technical reasons why I switched back to PHP after Ruby on Rails and I went to bed that night.

When I woke up in the morning, all of the technical blogs reposted it as their top-ranked article. There were hundreds of commenters attacking me personally.

Programming languages are peoples’ religion. It was like I was criticizing someone’s religion. For about a minute they hurt my feelings, and then I disconnected.


I had a really interesting conversation with Mark Randolph, who’s one of the original founders of Netflix. He said something to me that really got me thinking.

Mark said all ideas are rubbish. Ideas aren’t any good until they’ve been tested. All ideas are bad. How much should we fight for our ideas or how much should it be an A/B split test?


Go to I wrote an article about how ideas are just a multiplier of execution.

An idea itself is worth basically nothing if you don’t execute on it. There’s a really interesting guy in New York City named James Altucher.

He says that he writes down 20 new ideas every day and encouraged everybody else to do the same. Something about that bothered me and I wasn’t sure what it was. This morning it hit me.

Let’s take this to two extremes. Say you’re somebody that comes up with 20 new ideas every single day. By doing that, almost by definition, you don’t have time to execute on those ideas.

Let’s take the other extreme. Imagine you’re somebody that comes up with one idea every 10 years. For 10 years, you do nothing but full-time execute that one idea.

Given those two extremes, I’d place my bet on the success of the second person. This idea came out of the blue because I thought about our interview, and I thought about CD Baby.

CD Baby seems like two lifetimes ago. I’m 50 now and I started it when I was 27. I did that one damn thing for ten years. I remember there was a certain point when the company was eight years old that somebody pointed out to me that I hadn’t changed the website one single bit in five years.

I went, “Huh? Wow. You’re right.”

I hadn’t made a single line of HTML code change to the website in five years. It was just churning around and the sales were doubling every single year. I added nothing to it. I added no new ideas. I just kept executing that one single idea for ten years straight.

I think that’s why it was a success. People wanted me to branch out. People would say, “Why don’t you start selling DVDs? You could even make a lot of money if you started distributing porn.”

I thought, “No. I’m not looking for new ideas. I’m executing this one idea. That’s all I can do right now. Everything’s doubling in size every year. So, no, I’m good.”

Whenever you’re not sure where you stand on something, do a hypothetical thought practice of taking it to two extremes.

Spell it out in two very extreme and opposite circumstances. It helps you figure out where you might take a stand on that.


I’m fascinated by this. I could talk about this for the rest of the interview, but I’m going to challenge that a little bit.

I remember watching Ed Sheeran documentary and he said you have to create a lot of rubbish songs to create a lot of great songs

If you’re waiting for that great idea that comes once every 10 years, are you getting the chance to sift through all the rubbish?


If I were to prescribe a recipe for someone, it would be this:

Generate lots of ideas at the beginning. For every single one of these ideas, find a way to put them out there for testing like the book The Lean Startup suggests.

Make fake launching page for every one of your ideas. Whether it’s a physical product or a service you have in mind, make the launching page first before you do anything else.

Tell the world about it and see how many people sign up as interested. Especially if you’re actually asking for a credit card and if people seem willing to pull out their credit cards to pay for this thing.

If enough people sign up, then do the next steps and make the business happen. But if not enough people sign up, then let the idea go.

My prescription would be to do lots of this ideation up front. Then, when you’ve found the idea that the world seems to like and you launch it and it’s working, then stop this ideation process and execute like crazy on that one idea.

In hindsight, that’s what I did. Before I started CD Baby, I did lots and lots of things that failed. Then this one silly little hobby idea of mine took off and that’s what I ended up focusing on for ten years.

So, there’s a more nuanced, specific recipe for you.


I’m trying to put my myself in the shoes of many of my listeners who’ve not yet had their CD Baby idea. I also speak to a lot of entrepreneurs who have convinced themselves they’re not creative and they don’t have good ideas, which is nonsense.

I can see why creating 20 daily ideas can get your idea muscle stronger.

I get better at coming up with ideas by practicing coming up with ideas.


Ultimately, you don’t need a great idea. Business is just helping people. It’s about being a public servant. You’re just helping people with whatever they need help with. If a lot of people in your neighborhood are saying, “I need help shoveling snow or mowing my yard or I need help fixing my website,” help all those people that need it and you’ve got a successful business. Even though there was no brilliant idea. You don’t have to be super creative to help people. You just have to help them.

That’s what it’s all about. I think the feeling of needing to have a great idea comes from the occasional pseudo genius ideas where nobody knew that they wanted an iPhone until it existed.

Nobody knew that the existing Hoover vacuums were not that impressive until Dyson came along and made a better one. That takes a certain level of creative genius. They say that the difference between genius and smart is that the genius is the one that sees things that the rest of us can’t see.

It’s not just about being very skilled at something. There’s a place for those, “wow” innovations every now and then, but 99% of the businesses out there that are successful are not “wow” innovations. A lot of them are ditch diggers. Did you read Felix Denis’s book called How to Get Rich?


I loved it.


I absolutely loved it. Remember when he made the point that some of the most successful business people he knows are the ones that are literally digging ditches and doing sewage management and waste management? He said, “Everybody really wants to chase the exciting, glamorous idea. Everybody wants to be a Hollywood movie producer. But the most successful people I know are the ones that are doing the humdrum work that needs to be done. They’re not big idea people.”

I’d rather pop this notion that you need to be a big idea person.


I am really glad we pushed a bit on that question. There’s too much pressure for an idea to be a great one. That’s the problem. For example, Tetra Packed milk cartons made a family and all their future generations billionaires.

99.99% of ideas are simple solutions to problems hidden in plain sight.

We can’t help but be influenced by the media. Things get glorified. They’re not releasing glory stories on the ditch diggers that are making billions.


Can you share your idea about how often the first idea that comes to mind is not always the best?


I think that the first and second thing that come to mind aren’t very interesting because they’re an automatic reflex. Again, we’re influenced by mass media. So, if somebody says, “Name a famous painting,” you say, “Mona Lisa.”

That’s not very interesting, right? We all went there in our head.

“Name a genius”


These answers are too obvious. It’s not interesting.

Don’t say the first thing that comes to mind. Who’s the second genius that comes to mind?

“Richard Feynman.” That’s still pretty obvious.

Who’s the third genius that comes to mind? You can think slowly and ask yourself, “Genius of what? Genius of cooking? Genius of wordplay?”

You can take a minute to go beyond your first reaction.


You could apply that thought process to a lot of things you do. Ask yourself, “What’s the third best idea?”

Anything that could take you places you’ve never gone before.


I do this a lot in life. I doubt myself a lot.

I’m a skeptic in the original, philosophical, Michelle Montanye version of the word where I don’t even believe a word I say.

When I tell myself, “I want to travel,” I question it. “Do you really want to travel? I don’t know. I doubt it. Let me prove it.”

Whenever I hear myself express a preference, I try to shoot it down. This is how I get to the interesting ideas. This is when I pick things apart and get closer to something interesting and true.

Most of the time, like with my Mona Lisa example, the first thing that comes to mind is some habitual thing that our media has saturated us with.

What do you do on Mother’s Day? Call your mother.

Did you question that? Is that the best thing to do on Mother’s Day? Why?

To make her feel special? Isn’t that about the least special thing you could do if you think about it?

I love picking things apart and doubting yourself and going past your first reaction. It’s one of my favorite things to do in life.


Do you doubt yourself because you like to guess and second question yourself? Or is it because there’s something deeper in there?


Our actions reveal our values much better than our words do. If you’ve been saying for years, “I want to start a business,” for years, but if you haven’t done it, then I think you would be very wise to ignore your words and start looking at your actions.

That’s just one example. It could be that you want to quit smoking or that you really want a serious relationship.

Then why do you keep sleeping around with people at bars? Whatever it may be, your actions reveal the truth better than your words do.

Sometimes we echo things that the people around us believe. If enough people around us say it’s important to come up with lots of ideas, then you’ll start to repeat, “It’s important to come up with lots of ideas.” You might find yourself echoing something because the people around you say it.

You could also be saying something that used to be true for you 10 years ago and you’re still saying it out of habit without stopping the question if it’s true anymore. But life changes, you change, circumstances change, the world changes.

You may be declaring something that is true for a long time without questioning it. It can be really useful to stop and pull apart and doubt everything you say.

If you deconstruct it and at the end of it, you say, “No, this is actually still true.” Then that’s great. Now, you took the time to take apart that machine and put the machine back together again. It’s great proof that you still know that the machine is solid and well-built. It’s healthy regardless. If it’s still true and you can reprove it true, that’s great. But if it’s not true, then now’s the best time to find out.


I have a few questions.

Why did you go five years with no interviews?

And why were you so clear that you don’t want to start another company?


I found myself up on the metaphorical podium giving answers to everybody’s questions. That accidentally put me in a mindset of feeling like I had all the answers. I wanted to be the person with the questions, not the answers.

In fact, I have started saying “no” to all interviews again. I’m doing one more interview next week and then that’s it for a long time. Because I found myself accidentally once again feeling like I had the answers. That’s a dangerous mindset.

I’d rather be questioning everything than answering everything.

As for your company question, I didn’t like having all the responsibility. I had 85 employees. I didn’t like that I couldn’t completely disappear.

During my last two years of the business, I could kind of disappear. The business was running completely without me. But being the figurehead of the company, people still dumped their problems on me, or rather, they blamed me for their unhappiness. I didn’t like that responsibility.

I much prefer the work habits of a novelist or a painter who makes things alone. I’m a natural introvert. I really, really like solitude. I love doing things by myself. So, this idea of having a team of people reporting to me? I don’t really want that again.


What do you fill your time with now?


If I’m not with my kid, I’m writing – whether that’s writing computer code, writing my next book, writing emails, or preparing for an interview like this. My fingers are almost always on a keyboard if I’m awake. And I love that. It’s my favorite lifestyle.


I’m going to tell you a little fear I have and something I’ve never figured out, which is the perfect way to traverse from one question to the next in an interview.


I highly recommend go find the podcast called Conversations with Tyler Cowan. He’s an economist at George Mason University. His podcast is so damn interesting because he gets these amazing guests on the show and he’ll research them for 50 hours.

He’ll read all of their books and consume all of their past works before they’re on the show. He comes prepared with the most specific questions. He’ll get a politician on and he’ll say, “Why is Russian ballet superior to French ballet?”

And she’ll say, “Wow, I’m amazed that you know that about me! Here’s exactly why Russian ballet is French ballet.”

Then, Tyler will ask, “What’s your opinion on the food of East India versus West India?”

She’ll say, “Oh, East India is best because. . .

The reason he has these specific questions is because he did so much research. He knows that his interviewee has strong opinions on Russian ballet versus French ballet or East versus West Indian food. He peppers them with these non-sequitur questions.

It’s fascinating. It’s a problem for every single favorite interviewer I’ve ever known. Don’t feel bad about jumping to the next question with no sequitur.

Let’s practice. Pepper me with a few questions.

I would be pretty bad at being the interviewer. I admire that you’re putting your ass on the line and doing this. Thank you for doing it.

Let’s do Rapid Fire for the next five questions.


What’s the best advice you’ve ever received?


I have never received good advice.


What’s the worst advice you’ve ever received?


Get married.


What is one thing that you feel is wrong with the world that you would love to change?


Entrepreneurs thinking of themselves first.


What advice would you give your 75-year-old self?


[Laughter] Drink laxatives?



If there’s one person that you think I should interview alive on this planet, who would it be?




What does the word disruptive mean to you?


That we should all stop ‘rupting [laughter].

Before our interview, you asked me this question in advance. Why don’t you need a business plan or big ideas?

I sat with that one for a while and I thought, “Why does anybody think that they need this?”

I think that it’s become one of these little things that people say we need. For example, I don’t think anybody in nature would have decided that midnight, this moment when the sky is black and stays black, is when it becomes the next day. That’s a very contrived thing that someone, somewhere came up with.

Creating a business is like being a public servant. You’re there to serve. You’re saying to the world, “What do you need? How can I help? I’m at your service. What can I do?”

You don’t need a business plan to be a public servant.

That wouldn’t even enter your head. But people tell us that we need it. It’s another weird, false statement that we hear from others.


In our quickfire, you said entrepreneurs need to stop thinking of themselves first. Can you elaborate?


I didn’t really boil that idea down until in 2015.

They were re-releasing my book from 2011 called Anything You Want, which Seth Godin published it in 2011 with his publishing company.

In 2015, he sold it to Penguin. So, Penguin re-released it and they wanted a blurb for the inside cover.

They wrote something for me, they said something like, “Follow your passion.”

I thought, “Oh, God, no, no, no, no, no. Follow your passion? That’s not the point of the book at all.”

They said, “OK then, what do you want us to write? Because we want to put something there.”

That was when I asked myself, “What does it all really come down to?”

I had to ponder this. It was going to get printed in my book on the back cover. The best answer I came up with was generosity.

The thing that separates the really appealing businesses from those that aren’t, is generosity. If you’re running a business, you’re already probably luckier than most people in the world. So, you can afford to be generous.

Businesses stand out because of generosity, even if it’s just one person providing a service. It’s doing more than is necessary. It’s the opposite of being greedy. I find that the businesses that we detest are those who put their own needs above ours.

So, that’s the one thing entrepreneurs need to stop doing. Entrepreneurs need to stop thinking of themselves first.

If you put your clients’ needs above your own, so much that you might even take a loss on this sale, that’s the best thing you could do.


As you mentioned, your last book is called Anything You Want.

Is generosity the one thing you need to get anything you want?


No, the best thing you can do to get anything you want, is to want much, much less. And I’m not just being a Daoist dude on the top of a mountain saying that.

I’ve been thinking about that a lot lately. We’re recording this in May 2020 with the whole Covid-19 situation.

I’ve been thinking about worst case scenarios a lot, which got me wondering about the minimum I need to be happy.

In four weeks, I’m moving. I asked myself, “What do I really need to be happy?”

I came up with four things.

1. I need quiet.

2. I need a decent temperature where I’m not sweating or freezing.

3. I need to be near nature so I can go out for a walk.

4. I need somewhat of a view. It doesn’t have to be a view from the top of a mountain, but something more than looking at another wall out of my window.

Those are the only four things that I need to be happy, because if I have that, well, then I can flourish. Everything on top of that is not necessary. I realized that I’ve done this so many times in life. I’m lowering and lowering and lowering what I need to be happy so that everything on top of that feels like an extra bonus.

I did that with money long ago at the age of 22. I saved up $12,000 dollars, which to me meant I was rich because my cost of living at the time was eight hundred dollars a month.

At that point, I quit my job. I wouldn’t have to work for indefinitely because I was making around $1,000 a month and spending eight hundred dollars a month.

I’ve just tried to keep my needs low at all times.

So, how do you get anything you want? Think deeply about what you really want and then try to want as little as possible.


That’s fascinating. I don’t have this minimum viable happiness thing. I want to challenge myself because I’m surrounded by very expensive stuff, and I can’t get caught in the trap of Lamborghinis and Ferraris. But if you took that stuff from me today, I’d be cool with that. I want to enjoy it, but not let it get the best of me.


If you read up on Stoicism, that’s what they originally prescribed. They said go ahead and own wonderful, nice things, but don’t get too attached to them. Don’t deny yourself the pleasures. Have all the pleasures, but just know that they might disappear at any time.


More importantly, know what your pleasures are. Be agile in adjusting your expectations to the environment and the situation. That will help this mental health crisis and the constant chase that a lot of entrepreneurs face.

What areas outside of business, have taught you the most inside of business?


I don’t have a good answer for this, unfortunately.

The best answer that I can think of is psychology. My whole take on business is that it’s not business plans, financial plans, spreadsheets, and profit loss statements.

Business is serving individuals. That’s my whole personal perspective on business. So, the only thing I can think of that really applies to your question is psychology.

Isn’t it all psychology? Marketing is all about psychology. Pricing is all about psychology. It was fascinating to learn that people were given a placebo pill and told that it’s an expensive medication. These people reported more relief from their pain than people who were told that this placebo pill was cheap.

In another example, people who paid more money for tickets were more likely to attend the show. These things are fascinating.

The psychology of pricing, the psychology of where you fit into the marketplace and the friendliness of your town versus your standoffishness, and how some people prefer the standoffishness and they aspire to be in the luxury crowd.

It’s all psychology. It feels like a non-answer to me because it’s so obvious.


Was there anything that you held as truth for a long time but recently changed your mind on?


I want to travel. I want to live in a multicultural city. I want a dog. The best school is what’s best for my kid. Minimalism means bringing nothing with me when I move. I like having smart and famous friends.

Those are those are seven off the top of my head.

I’ve been saying that these the things I want most in life, but t I’m realizing that I might not want them if I’ve been saying it for years.


Do you think they’ve changed for good?


Earlier, we talked about the previous version where it was true, and now I believe the exact opposite. For a long time I said that I wanted a dog and now, I do not want a dog. For a long time I said I want to travel. Now, I do not want to travel.

Granted, as you can hear in some of these, there’s a common thread that many of these are recent 2020 changes. Travel and living in a big multicultural city were a lot more appealing five months ago. Now it’s not. Five months ago, I would have said that those are two very, very essential things and that I very much value those.

I picked those ideas apart and asked, “Do I really want to travel?”

I used to think that I really wanted to get on a plane and go to places. Now, I want to learn about places in a different way, not just because of Corona.

Physically getting on a plane and visiting can be a bit of a red herring or a placebo in itself. It makes you think that you’ve understood this place because you’ve walked around and smelled it.

But maybe having one on one conversations with people from that place, watching the top five films from that place, reading four books about it, and learning some of the language, you might spend the same number of hours doing that as you would walking around the marketplace. But you’d learn much more from the former than the latter.

Up until recently, I really loved having smart and famous friends. Now, I realized that I like having smart and famous acquaintances. I like having smart and famous conversationalists.

But friends? That’s a different category. That’s about emotional trust and intimacy. I realized that true friendship is purely emotional. I don’t care what somebody has achieved in their life or how book smart they are. It’s all about your emotional trust with somebody that makes a real friendship.

Someone could be the most smart, intellectual, interesting, famous person, but if you don’t feel an emotional safety with that person, they aren’t really a friend, they’re an acquaintance. They’re a conversationalist.


In last three years, I made a few very famous friends and I really like them. Almost more than friends I’ve held for many years. So, I’ve had almost the opposite view.


I find that a lot too sometimes. It’s a truism that I started projecting a while back that your old friends are your best friends. I found that I was changing so often and moving so often that I had almost nothing in common with my old friends anymore. Whereas the friends I met during my newest situation, I could relate more to because I felt like it was the most current version of myself.


I get that.

To go back to your travel comment, I’ve never really been into travel.

There’s a lot of fantasy around another city with all of its culture and cosmopolitan and art and music scene. But sometimes you haven’t seen what your own city has to offer. We can live somewhere and not truly see it. Because we’re always wishing we were somewhere else, we can’t see what’s beautiful about where we are.


A lot of people’s travel desire is to try on being different versions of themselves. I think we all have different aspects in our personality, different selves inside ourselves.

Could I be a New Yorker?

Let me go to New York and see how I feel in New York. Let’s allow the New York side of my personality to come out and see how that feels.

I think I’m going to go live in the Australian outback for a year and see how that crocodile hunter side of myself comes out [laughter].

What if I were to live in Paris and be oh so continental.

People want to try on these different aspects of their personality. Sometimes, it really does click. Somebody from the middle of Iowa might visit Italy and go, “Oh, this is the real me.”

Actually, I’m thinking of a specific person that I know really well. At the age of 19, one of my best friends went from the middle of America to Italy and never came back. She’s fluent in Italian and hasn’t been to America in 20 years. Italy is her place. She needed to make that switch.

I left America 10 years ago and I hope to never go back. It doesn’t feel like my place anymore. There are many people who also bounce around the world and finally come back home and see it in a new light. A lot of New Zealanders do that.

New Zealand is paradise. These kids grow up in paradise. Then, at the age of 20, they have to get out. They have to go see the rest of the world because it’s this isolated island in the Pacific.

They actually call it OE in New Zealand, which stands for overseas experience. Everyone says, “Go do your OE.” Then, at the age of 30, they come back to have kids and stay put. It ends up just being this little journey that you make to get to know yourself a little better and maybe make you appreciate home even more.

Sounds like you already appreciated your home, but a lot of people don’t appreciate it until they’ve gone away and realize, “Oh, relative to these glorified places, it’s actually more awesome.”


On your website, you said you were spending about one to three hours a day getting interviewed on people’s podcasts.

When you were in the flow of these interviews, why were you doing that?


At first, I didn’t know. I had a list of 180+ people who asked me to be on their podcast and I would say “no” to every single one. I would make a little note in my database for every person that wanted to interview me.

At least a few times a week, I was saying “no” and the list kept growing. I thought, “It’s been five years. Maybe I should start to do this now?”

But I didn’t really know why. You can tell I’m not here promoting anything, but as I’ve gotten into it, I think that the questions I get asked are great writing prompts.

I dig into them a lot and sometimes I accidentally spend five hours preparing answers. I don’t prepare the answers word for word, but I like thinking through the subjects.

For example, somebody asked me yesterday, “What is your definition of success?”

I thought, “Huh? I’ve never thought about that. What is my definition of success?”

I sat there for two hours writing on that subject. The best thing I came up with is that success is whatever makes you feel proud. That’s it. But it took me two hours to get there.

But right now, I need to take a little break because my third book is unfinished and some other programming I’m doing is unfinished because I’m spending hours a day doing this stuff and not doing that. I need to get my priorities straight again for a bit and I will continue doing these again.


Something I personally believe people get wrong is the definition of happiness.


How so?


People think happiness is contentment. There’s a huge, common theme of minimalism and doing less, but that is against human nature of evolution and the striving for growth and progress.

When people say, “I just want my kids to be happy.” I think that’s one of the worst ways to raise your kids. Because your kids need to be independent. If they don’t go through a challenge right now, they’re not going to be disciplined. If you don’t actually put them through stuff that they don’t like, how are they going to get a sense of growth and achievement?

I don’t I don’t feel like the goal in raising the kids is for them to be happy. I feel like the goal in raising kids is to show them what the world is really like for when they go into it. I’m no parenting expert.

I can honestly say my greatest sense of happiness was immediately after one of my worst experiences in my life. When you overcome that challenge, it’s amazing.

I broke the world record for the longest public speech, and it nearly killed me. My voice went away, and it was the hardest thing I’ve ever done. Afterwards, I felt such elation.

I thought, “For everyone who thinks happiness is contentment, you’re missing this. You’re missing what we’re supposed to do as human beings, which is to strive and to grow and to evolve.”

What are your thoughts on the drug war is happiness?


I think a lot about deep happy versus shallow happy. You just described it perfectly.

Shallow happy is what you call contentment. Deep happy is what you described after your long speech. I love the fact that I have been teaching my kid about this since he was two or three years old.

I said to him, “That’s deep happy versus shallow happy.”

He said, “What does that mean?”

I said, “Shallow happy is when you eat ice cream. Deep happy is when you invent your own flavor of ice cream and you give that ice cream to everybody in your neighborhood and it makes you really happy.”

He said, “But I don’t like ice cream.”


I said, “OK, well, let me think for another example. Deep happy is when you do something difficult. You set out to do something difficult and then you do it and you’re really, really deeply happy because you’ve done something difficult. You’re really proud of yourself.”

He understood that example better.

I said, “What’s a little sad to me is that a lot of people just focus on being shallow happy. They don’t know how good it feels to be deep happy. A lot of people just eat the ice cream and they watch TV and they never know deep happy.”

So, we had that conversation and I thought that he probably would forget because he was three. But a month later, he came to me and said, “A new kid came to our school today and I told him about deep happy versus shallow happy.”

I thought, “Yes! He remembered!”

I said, “What did you tell him?” And he echoed it back to me.

He said, “I told him that anybody can be shallow happy. That’s easy. That’s just doing something fun. But deep happy is when you do something difficult and then you finish it.”

You can also look at what you want now versus what you want most. That one really stuck with me. I can’t remember what random book I read that from. Shallow happy is doing what I want now. Deep happy is doing what I want most.


I’m very privileged to have such a long conversation with you.

I know you said you don’t come on this podcast for a promotion, but I would love for people to be able to find you and get your book.

Have you written two books now?


I’ve written three. I’m writing my fourth, but only one is out there today. Depending on when this hits the air, my next two might be released.

The first book is the one I wrote in 2011 for Seth Godin. It’s called Anything You Want.

My next book coming out is for musicians, and it’s called Your Music and People. My speed punk, country metal example from earlier, that was a story from that book.

A friend of mine that’s a real marketing guy said, “You’re saying that this is a book for musicians. But this is a book about marketing and positioning. You can read it metaphorically.”

You might find Your Music and People interesting even if you’re not a musician because you can read metaphorically.

My next book after that is called Hell Yes or No. Which is a collection of my best articles from the past 10 years.

Then, my fourth book that I’m still writing right now, I’m so damn excited about. It is called How to Live.

To find me? You can go to Everything I do is there. My email address is still widely out in the public. There’s a contact page with my email address in a big font.

Please send me an email and introduce yourself because that is one of my favorite things.


I’d love to stay and talk all day. I’m really grateful to you. I’ve really enjoyed this. It was everything I’d hoped it to be. Thank you.


Thanks, Rob. I really appreciate it.