Derek Sivers

Interviews → Asia Professional Speakers Singapore / APSS

Private call to an association of professional speakers. Tips for giving a good talk, building an audience, keeping people surprised, being social as an introvert, sharing one idea at a time, how inspiration meets us halfway

Date: 2020-02

Download: mp3 or mp4



What I’ve got for you today is not truly a presentation. That would be too meta. Instead, I’m here for a conversation.

I’ve got a couple of questions that were emailed to me in advance, and I hope that while I’m talking, you collect your questions. I have a little bit of stuff prepared. Mostly, I would like to hear what you guys want to know.

I’m going to start with a story that you will appreciate. When I was in my 20s, I was a musician, and I had recently started an online music store called CD Baby. I grew up in Chicago but was living in New York City.

A group that I hadn’t heard of before called The Chicago Music Group emailed me about something. I said, “Chicago Music Group. What’s that?”

He said, “A bunch of musicians get together once a month for a gathering, and we talk about things pertaining to being an independent musician. I said, “Cool. I’d love to come to one of those.”

He said, “Great.”

Later, I said, “I’m going to be in Chicago on April 13th. Maybe I could come that day.” He said, “Yeah. That would be great. Come on down.”

So on April 13th, I found the directions. I was following a GPS, and I think they said, “We get together from 7:00 to 9:00.” I thought, “Okay. I’ll show up sometime between 7:00 and 9:00.”

I got a little lost, and I got there about 7:45. I’m giving you all these details because of what happens next.

I find this dark door in a dark part of town, and knock, and somebody says, “Oh! Derek, you’re here! Oh, great! Oh! I’m so glad you’re here. Great! Let me bring you in this way.”

I thought, “Okay. This is a lot of celebration. Why is he acting like this?”

He leads me down this hallway, and he opens this door, and suddenly, I’m on stage. There are a couple of hundred faces watching me.

They said, “Ladies and gentlemen, Derek Sivers is here. [Clapping] Will you please welcome Derek Sivers. Okay, Derek. Go.”

I said, “What? I just thought I was attending a meeting of your music group.”

He said, “Oh, well, we thought you were coming here to speak.”

I had never in my life spoken publicly before. I was suddenly on stage, and they had put aside 45 minutes for me to talk. And I was late. I didn’t know that I was supposed to be there at 7:00. I just thought I was attending somebody else’s party as a guest.

On the fly, on the stage, I had to think of 45-minutes of things to tell a room full of musicians.

I came up with some things. If you were a musician, we went out to dinner, and you said, “So, what have you learned? Can you give me any tips?”

Then, yeah. I guess I would have had 45 minutes of tips to give somebody.

I sat there on stage and gave people some tips and shared some stories that I thought were enlightening. That was my introduction to public speaking. I still don’t consider myself a speaker, but here are my thoughts.

For one, my opinion is that people come to a talk to learn something new. I think my introduction to watching public speaking, outside of a few conferences, is when I started going to TED as an attendee. I watched tons of 18-minute talks for four days.

I thought about why I was there. “I’m here to learn something new. I don’t want to hear what I already know.”

Later, when I became a speaker, I thought, “I’m only going to say something if I think it’s something new and surprising.”

That leads to #2, which is that people only learn when they’re surprised. If they’re not surprised then you’re just telling them what they already know.

You might spin a great tale, and they might clap. But if you’re not surprising them then everything you’re saying is just fitting in with their existing view of the world. It’s only when you change their view of the world that they learn.

Number three, cut out everything from your talk that isn’t surprising.

This is my Beginner 101 thing when somebody emails me and asks me if I have any public speaking advice. I would say, “First, skip everything that isn’t surprising. Don’t think ’This is my moment in the spotlight. I’m going to get up there and tell my tale. Everybody is here to hear the story of David.’”

No. People aren’t coming to hear your biography and history. You can eliminate all of that. You don’t have to get up on stage and say, “Before I begin, let me tell you something about where I came from. I am this. I am that. I just went here.” No. They don’t care. They’re not here to hear about you. They’re here to think about themselves.

Your job is to help them do that. It isn’t about you; it’s about them.

I cut out everything from my talks that isn’t surprising. I don’t get up there and give context about “First, let me tell you who I am.” Well, I might have done that sometimes in the past, but I regret it. I would not do it again.

Number five, nobody ever complained that a talk was too short. If they wish you would have said more, then I think you’ve said just the right amount. You don’t want to make them full; you want them to still be a little hungry.

When my talk is done, I want the audience to be a little hungry to know more about me instead of feeling like, “I am satiated and full with that guy.”

Ultimately, I think that public speaking is mostly entertainment.

Yes, it’s educational. Yes, it might be motivational. But to me, those are all secondary.

I’ll stop and tell a little story here about the TED Conference. TED sent out an email a month or two before the conference to registered attendees which said, “We’re going to do some audience talks. If you have something you’d like to present to the audience, let us know. You can pitch three ideas.”

So, I did. I pitched two ideas that I wanted to do. Then I looked at this blank that said number three. I thought, “I’ve got to put something there. I read an interesting article this morning, so I’ll put that in as number three.”

Of course, you can guess where this is going. They picked number three for me to do on stage at TED. Not TEDx, but TED. I had to deliver a talk about an article I had read that morning which was about how how announcing your plans makes them less likely to happen. I did a bunch of research.

Peter Gollwitzer, from NYU, had done some research, and I had to present it as if I knew what I was talking about. And I didn’t know anything. I made an entertaining 2 1/2 minutes about this subject, and I presented it.

Ever since, people email me as if I’m some kind of expert on the subject.

They’d say, “Well, what about this? What if I announce my plans, and Đ?” I don’t know. I’m not an expert on this. I just gave an entertaining 2 1/2 minutes on stage.

Those are the points that I prepared. Frederik asked me to talk about why I stopped speaking and stopped being on podcasts. I think that’s because when I was doing this a lot, I started to feel like an expert. I started to feel like a know-it-all. That made me feel a little stuck in my ways.

I like to have more questions than answers. I think when you get into a dynamic where everybody is asking you questions, and you’re the one delivering answers, you start to get into a mindset where you think you have the answers.

I found that was hurting my intellectual development. I did a really high profile interview with Tim Ferriss on his podcast. It got so many listeners that I felt like, “Okay. I’m done for a while. I’ll let that reputation coast while I hit the books and become a student again.”

Now, I’ve got a couple of emailed questions.

Question: First, a question from Siva in India of Hi, Siva. I hope you’re here. Siva asked me, “What are a few ways and tips to build a global followership and global tribe?”

Answer: Here’s my advice. My thoughts on this were first, achieve something interesting.

Audiences want to listen to people who have achieved something, but it doesn’t necessarily mean that you have to go make a lot of money.

Let’s compare two examples Đ two potential speakers. One, someone who made millions because he was an early employee at Amazon. Or, two, somebody who won a memory competition after studying for only one year. Someone who now has a bunch of advice on how you can improve your memory based on what he learned even if he won a chocolate bar.

I would much rather hear from somebody who won a memory competition.

There’s a great book on that called Moonwalking with Einstein. Fascinating! The author was a journalist assigned to write a story about memory competitions. He showed up to this memory competition and said, “This is weird.” And a year later, he won the memory competition. He tells his story about how he did that.

So it’s not about making a lot of money. Don’t think, “I have to go make a lot of money” in order to be an acclaimed public speaker. I think people just want to get advice from someone who has achieved anything. Again, it’s not about you.

Another good example is Tim Ferriss. Around 2005 or 2006 before he released the 4-Hour Work Week, he knew he wanted to be famous. So, he went and achieved interesting things. He won a record in Argentine tango, and he lost 40 pounds quickly.

More importantly, he turned these into actionable steps showing how you could do the same.

So, I think that achieving something gives you the ability to answer the audience’s question, “Why should I listen to you?”

And the most important thing is next, which is to develop succinct and quotable, actionable steps.

You get famous not from telling your tale, but from keeping your focus on the audience.

Your achievement is the thing that tells them why they should listen to you, but great advice should be catchy and memorable for the audience.

If you tell an interesting point, but it takes a few paragraphs to describe then it doesn’t spread past that room. It takes too long for your audience to explain it to others.

Nobody wants that. They want to hear three, four, or five words that get the point across. I do that for anything I want to spread.

Also, use every medium. Some people only read articles. Some people only look at Instagram or Twitter. Some people only read books. Some people only watch YouTube, and some people only listen to podcasts.

To reach the most people, you have to use every medium.

First, take the time to write great content. I highly suggest hiring an editor to improve it. Look at the Editorial Freelancers Association.

Then, get some catchy pull-quotes from it because first, you have to turn these into articles that you can post because some people only read articles.

Combine them into a short book that you can put on Amazon. It can be even just like 60 pages.

If you’re self-publishing, you don’t need to do that thing that you do to please Penguin. You don’t have to turn it into a 300-page book, so it looks good on the shelves.

My first book was only 80 pages. I never intended to write book, but Seth Godin started a new publishing company. He called me and said, “I’d like you to be my first author.”

I said, “Okay.” You can’t say no to Seth Godin.

He asked me to make a book that was only 11,000 words or about 80 pages Đ a book that could be read in under an hour. So, I did. It’s called Anything You Want.

I get many emails from people thanking me for keeping it short because a lot of people don’t like to read books or if they buy a book that’s over 300 pages, they never finish.

Make videos and audio podcasts of the article. Share it with people in that format. Share the quotes on Twitter and Instagram.

Reach out to be a guest on other people’s shows or sites.

Thank you, Siva, for that great question. I spent an hour thinking and writing about it.

Question: From Dr. Philip Merry in Singapore of Hi, Philip, if you’re here.

Philip says, “It seems like a lot of synchronicities happen to you. They are out-of-the-blue coincidences. What’s your take on synchronicities and entrepreneurship?

Answer: I think that you have to be out there doing things. Phil, I looked at your website. It sounds like you’re already doing it.

Being out there doing things means you’re meeting strangers, trying new experiences, doing a variety of jobs, and always looking for opportunities Đ ready to say yes to anything.

I hear from a lot of people that go to school, go to University, then go straight from University to some office job. Their life has been contained in this narrow track: school, University, office job.

Then they say, “I wish I could start a business. But I don’t know what to do.”

Wishing doesn’t do it. Entrepreneurship is a very different approach to life than getting a job. It’s a hustle. It means being out there. I’ve got three short little stories for you.

I don’t want to indulge in these three stories. Just find the common thread about this synchronicity question in these three stories from my background.

When I was 17, I was in a band with somebody who had a booking agent. He was much more successful than I was. His booking agent offered him a gig playing guitar at a pig show for $75 in Vermont, which was a $50 bus ride away.

He said, “No. I don’t want that stupid gig.” So he asked me, and I said, “Oh, yeah! My first paying gig.”

I took a $50 bus up to Vermont, and I played $75 to play guitar at a pig show.

The booking agent got good feedback and said, “Hey, the musician from our circus just quit. How would you like a full-time gig traveling with the circus?”

For the next 10 years, I was the ringleader, MC, and musician of a circus.

Two, when I was at college, a music school, a visiting speaker came. He was an executive from BMI in New York City, and he was a pretty connected guy in the music industry.

Just as he was walking into class, I heard him say to the teacher, “Oh, I thought we were going to eat first.” The teacher said, “No. I thought you ate already.” He said, “How long is the class?” He said, “Two hours.” He goes, “Oh, man. I’m hungry.”

While everybody was still getting seated, I dashed out to the phone and quickly called Supreme’s Pizza, and I said, “Send five pizzas to Room 304.”

About half an hour later, five pizzas showed up, and this executive said, “Alright, kid. Good move. I owe you one.” He gave me his card afterward.

A few years later, after I graduated from college, he got me a great job in New York City at Warner Brothers Đ one of those jobs that’s hard to get unless you know somebody. I had a sweet job in New York City just because I got pizza for a guy.

Lastly, when I was living in New York City, my roommate was an assistant engineer, a lowly engineer wrapping cables for minimum wage at a recording studio. He came home one day and told me that Ryuichi Sakamoto, the famous Japanese musician, was about to go on tour and was looking for a guitarist. My roommate told him about me.

I thought, “Oh, my gosh. I want that gig.” I did whatever it took. I stayed up all night. I got a copy of his recording. I busted my ass, and I got the gig.

At 22, I was playing to audiences of 10,000 in Tokyo, on stage with this Japanese pop star. I got that gig because my roommate was wrapping cables and knew somebody.

I think the answer to your question about synchronicities is not some kind of magical universe thing. It’s about throwing yourself out there, saying yes to everything, trying lots of different experiences, and doing lots of different things.


I received a question about your voice. You’ve got a great voice. It’s fun to listen to. Do you consciously work on your voice?

Also, how important is the esthetic when it comes to being entertaining, being interesting? Whether that’s good looks, good sound, good color, good whatever it is?


Voices mean a lot, don’t they? When I was running CD Baby, sometimes people would CDs of guided meditation to sell.

The music begins [whish sound]. Then the person starts speaking. [Gruff voice] “Imagine a blue light. You are a blue light.”

I’m thinking, “Oh, gosh. No! Come on. You put so much effort into this. Do you hear your voice?”

I think a voice is definitely something you can work on. I practiced singing for 15 years. That might have a lot to do with it. Go to to read my story of how it took me 15 years of practice to learn how to sing.

After 15 years of practicing an hour or more a day, I finally became a good singer.

I have spent many, many hours practicing like [throaty voice], making things throaty if I want to. You can practice with different registers. Then, I think you notice the difference of being a dynamic speaker, even just conversationally among friends.

I have a friend from Sicily, and [dramatic voice] she is one of the most dynamic speakers I have ever heard. She whispers. She shouts, [shouting voice] “Enough. I do not believe. [Whispering voice] I don’t believe that everything has to go around this.”

She’s one of these very dynamic people, and she’s fascinating to listen to. But no voice lessons. She’s not an entertainer. She’s not a public speaker. She’s just Sicilian.

I think varying your voice is very, very useful. When I was 18 after I first started working in the circus, I learned how to vary my voice. I knew how to vary my voice conversationally, but when you’re on stage, you can practice even more.

I was the ringleader/MC of the show. But I would get up there, and say, [flat voice] “Hey, everybody. Welcome to the Mime Circus. Yeah. The show’s going to begin pretty soon if you want to take your seats. We’re going to start our show. So, yeah. Here it goes. Welcome to the Mime Circus.”

I went backstage, and the boss said, “No. No. No. Come on. Be more dynamic.” The next day I’d go out there and say, “Hey, everybody. Welcome to the show.” He’d say, “No! More dynamic.”

Eventually, to be a little passive aggressive, I thought, “Okay. I’ll show you.”

I went out on stage, and said, [melodramatic] “Ladies and Gentlemen, what you’re about to see is the most amazing thing.” I made it an absolute caricature of the carnival barker.

I went backstage, and he went, “Yeah! Now, there you go. That’s what we’re looking for.”

It was a good example that when you’re on stage, you can be ridiculously dynamic, and it seems natural because you’re on stage.

You asked about the esthetics. I’ve been to the TED Conference many times, so it feels it’s a crash course in watching speakers. I don’t remember what any of them looked like.

For the most part, people are facing your direction. Their eyes may be looking your way, but their mind is completely on themselves. I think they’re not really thinking of you.

So I think the esthetics don’t matter that much, except for the obvious. If the sound is bad or the lighting is bad, that’s distracting.

But as long as you’ve reached some base-level, you don’t look horrendous, you don’t sound horrendous then it’s more about the message. Then it’s about your voice.


What about the accompanying material that you present? Like slides and other visuals?


It doesn’t have to be the most handsome, but you don’t want to be so ugly that it’s distracting.

I would refer to the typical advice out there on slideology.

Seth Godin takes an interesting angle. He never puts words on his slides. He only uses images that go with what he’s says because he doesn’t want people to get distracted by copying down what’s up there.

But sometimes, f you’ve found your takeaway phrase, those little three to five words, it does help to put it on a screen. I watched an interesting thing happen over the last 20 years of doing this. It used to be, when you made an interesting point, heads would go down because they’d write it down.

Now, when you make an interesting point, their phone comes up because they take a picture of the screen. Put your takeaway quotes on the slide, not bullet points, because people are Instagramming it.


Let’s talk about podcasts. Why bother making one and competing in that space? You’re in this waterfall, this ocean of all kinds of noise, and you may be saying something in there, but why? I’m curious about your thoughts behind that.


That would be like, why bother writing? The words have already been said. Why bother speaking? People have said everything.

To me, everything starts with writing. First, you write something really fascinating. Then once you’ve composed your words, you use every medium.

Once you’ve written something that you feel is worth spreading and sharing then it’s almost routine to use every medium that people listen to. At first, I felt the same way about podcasts. Why start another one?

People have asked me for years, “Will you make a podcast?” I said, “No. I’ll just go be a guest on everybody else’s podcast.”

But then, I realized that the podcast was another medium to share the articles that I was writing. So my podcast,, is just me reading my articles.

I didn’t want to create another Joe Rogan style podcast where I sit down with a guest every week, and have a two-hour conversation. Other people can do that. I see it as another medium for sharing my articles.


Can you talk to us about minimalism?


There’s minimalism publicly and privately.

Privately, that’s a preference. If you like to have a home with nothing in it and if that makes you happy, good for you. If you like to have a home with lots of stuff in it, and that makes you happy, good for you.

But publicly, I think it’s considerate. It’s editing. It’s removing what’s unnecessary.

I learned the hard way. For 10 years, I ran an online music store called CD Baby. It had a couple of million customers. Whenever I sent an email out to everybody, it meant that I sent it to a couple of million people.

If I had one sentence that was unclear, I would get over 5,000 replies from people asking me to explain what I meant by that. It takes a lot of time to answer 5,000 emails, but I would do it because shame on me for saying a sentence that was not as clear as it could be.

Each time, I would look at every sentence I had written and think, “Is there any way this could be misunderstood?”

We think that the goal of communication is to be understood, but I think you could flip it and say, “The goal of communication is to not be misunderstood.

To go back to the speaking materials we talked about, you should look at the quality of your slides and say, “Could this be misunderstood?”

Before sending out millions of emails, I had to fix the sentences that could be misunderstood. But I also found out that if I wrote an email that was longer than say nine sentences people might miss the most important point. So those people would reply back by the thousands.

Say I wrote, “We’re starting a new program. It’s going to give you these benefits.” The 9th or 10th sentence would say, “Here’s how to do it.”

Five thousand people would reply and say, “Great. How do I do it?” Because if it falls in the 10th or 11th sentence, people just didn’t notice it.

I think that’s where my super-succinctness in public communication began. I realized the more sentences you use, the less likely they are to hear them.

I also really like that my three TED Talks that are out there are under three minutes. I think that whatever you put out into the world, whether an article or a talk, should try to include just one idea Đ so that the takeaway is just one thing. If you have another idea, make another article or another talk. Don’t try to fit 10 ideas into one thing.


When you’re putting together one of these talks or articles, are you trying to communicate clearly to a smaller group or a larger group?


I think in large-group now, maybe because of my history with CD Baby.

I feel that everything I say publicly has a big audience now.

You’re in Singapore. I love the fact that in Singapore, you can’t assume that English is everyone’s first language. Growing up in America, it was too easy to assume that.

Assuming that I have a big audience of all different kinds of people helps me focus on saying things clearly and succinctly, so I’m not misunderstood.


You have a reputation of making observations and sharing your insights. What’s your state of mind as you go through life? Do you look out for these things, or do they just happen to you?


There are two different mindsets that you can have. They’re head-up and head-down.

When I am head-up, and I’m actively looking for new ideas, new connections. But you have to be head-down to focus in order to turn an idea into finished output. At those times, you shut yourself off from new stimulation in order to get something done.

For example, I was very much in head-up mode until about Christmas. Then I realized I had some projects that were not getting done because I’d been so head-up, inspired, and doing so many new things that some unfinished things we’re getting completed.

So the last two months or so, I’ve been very much head-down. I haven’t read anything new. I’ve deliberately shut out new inputs to finish the things that I started.

I think you can be very deliberate about inspiration. If you’re feeling like you want more ideas, then instead of blindly walking around and hoping to have new ideas, read books from different fields. Read a book on how the root systems of trees work or read a book on ostrich farming in Mongolia, Then you can make these unique connections. You can think, “How could this be a metaphor for something else, or how is this like that?”

I wrote a simple Linux database where I could catalog all the ideas I’d come across in a database. Then I wrote a little program that shuffles them up to match them with other ones. So imagine two spinning roulette wheels. It randomly matches say idea #17 and #83. Then I think “Hmm. How are these things similar?” in a way that I wouldn’t have ordinarily looked for.

I did this because I noticed the things that I had put out into the world that were the most rewarded and celebrated were things where I had made this lateral thinking metaphor accidentally.

For example, I talk about how to start a movement in a TED Talk.

That idea came after watching a little YouTube video that somebody was spreading around. It was at a concert where this guy starts dancing, and everybody joins in.

I saw the video and thought it was cool. But I had recently read the book Tipping Point by Malcolm Gladwell and Tribes by Seth Godin. Those ideas were still echoing in my head.

So I went, “That video is like what Malcolm Gladwell was talking about with how things turn into a movement, and it’s a little bit like what Seth Godin was talking about in Tribes.”

So in half an hour, I wrote an article about how the dancing guy video is like leadership. Then, the TED Conference asked me to turn that into a talk.

But you can approach that deliberately. You don’t have to just walk around, hoping for inspiration.

A lot of songwriters talk about this kind of thing, but there’s a wonderful metaphor that if you personify inspiration as a muse, like any worthy romantic partner, she’ll never make the first move. You always have to make the first move, and then she’ll meet you halfway.

So never wait for inspiration. Sit down at your desk. Start writing without inspiration, and once you start working, inspiration will come and meet you halfway.


What drives you to keep creating and putting yourself out into the world? What drives you to do it over and over again?


Good question. There are two things. I’ll do them in reverse order.

Number two, I like meeting people. It’s why I asked Frederick to ask you to email me questions in advance. I really enjoy the direct connections that I make.

Anytime I do a podcast or something, I ask people to email me afterwards. I say, “If you’ve made it all the way to the end of this interview, please, here’s my email address. Send me an email.” I’ve met some of the coolest people that way.

Some of my best friends now are people I met because they heard me on a podcast and emailed me out of the blue. I’ve also met really interesting people like a shoemaker in Slovenia. I think, “Cool. I know a shoemaker in Slovenia now.” We email every now and then. My Sicilian friend I’m visiting now is somebody who sent me an email after an interview.

So number two, I like meeting the people I meet because of these things. I hope you guys send me an email afterward because I think it’ll be cool to meet you. Go to My email address is in big letters there.

And number one, we call it creative expression, but sometimes, I think it’s the curiosity about the realization of an idea.

I spent around 15 years as a songwriter before I started CD Baby and then did that for many years before I started public speaking.

With songwriting, I think it often starts with curiosity. For example, you could have a melodic idea, and you wonder, “Could I combine it with this harmonic idea or this lyrical idea? I wonder how that would work?”

You make this thing, and when you’re done, you think, “Cool. Now, let me see if it’s reaching other people the way it’s reaching me. Am I the only person that thinks this is interesting?” Then, you put it out into the world.

I like that we call it release. You release an album. You release a book. It’s not yours anymore. It belongs to the world. I think of articles and talks in the same way. I put it out to the world because I think it’s the final test.

It doesn’t even mean you’re searching for adoration or applause. You just want to see if it’s reaching other people too.

Then the world gives you feedback. They might say things like, “Ugh, it’s too slow to start.” Or, “You lost me in the middle.”

Then you realize, “Oh, yeah. You’re right. It could be improved if I change this.”

I still think of the stuff I put out in the world like that. If I think something is an interesting idea, I wonder if other people will think so too.


Now we have some questions from our online participants.


Derek, I like how youŐre into stoicism and quite an introvert.

With a social window of two to three hours, how do you suggest that speakers approach things in order to meet people and also have enough personal space and time to think and be introspective?


I don’t listen to many podcast, but one of my favorites right now is called Conversations with Tyler. It’s hosted by Tyler Cowen. He’s an interesting intellectual at large who interviews really interesting guests, and they have an intense intellectual conversation for an hour.

He recently interviewed somebody who has a public speaking background. He asked, “You’re an introvert and also a public speaker. How do you reconcile those two?”

The guy instantly said, “Being a public speaker is a great thing for an introvert to do because I hate chitchat. I really get uncomfortable if I’m at a party, and people are chitchatting. When you go on stage, it’s the ultimate way to talk and not have to engage in any chitchat. You can look incredibly social and have to do no chitchat at all.”

The other part is, sometimes, even if something is not your nature, you can fake it anyway. I used to attend a lot of conferences even though I kind of hated them. I would turn on my extrovert side for one hour.

You go into the lobby with a whole bunch of people, you chitchat, you meet people, and you say, “Hi. What do you do?” You remember people’s names, and you use all these conversational skills you that you can learn from books on how to talk to people.

You do that stuff for one exhausting hour or three tops. Then, you retreat back to your hotel room. That can be enough.


When you’re putting your message out to millions of people, as you’ve been doing in the past, there must be that small percentage of people who are either drunk or crazy or don’t understand, or have good points going against what you have to say.

How do you handle and manage that kind of feedback, especially the ridiculously mean, hurtful comments that you can get online when people are hiding behind their keyboards? How do you manage all of that negative energy that comes at you when you put yourself out in a very public way?


One, I like letting go of the need to be right. When somebody, especially those people who make good points that disagree with yours, I don’t debate. I don’t like to debate because I’m not ever trying to convince somebody to my way of thinking.

When somebody says, “I completely disagree with you, and here’s why.” I hear them out, and I say, “Cool. That’s a really good point. Thank you.” Then, they’re acknowledged, and they’re happy. That’s it.

I’m not going to go, “No! I’m telling you why I’m right.” Even if I think that their thinking is completely flawed, I might just say, “That’s a good point.” And end it with that just to be polite.

Some people do, but I don’t enjoy debating.

Here’s a different angle to that same question. Ten years ago, Mac and Windows people used to fight about which one is better. Programmers still do that. If a programmer has invested years of their life into learning Java, and somebody comes along and says, “No. Ruby is better,” They get mad. They will fight to the death over which language is better.

In my 30s, I used the Ruby on Rails programming framework for a couple of years. Then I stopped, and I switched back to PHP. A bunch of different people asked me why by private email.

After answer the third or fourth email, I thought, “I’m going to post this on my technical blog that nobody reads.” I had zero readers at the time.

So on my birthday, when I turned 36, I wrote, “Here are the seven reasons why I switched back to PHP after two years of using Ruby on Rails.” The next morning when I woke up, for some weird reason, I saw that the article had been picked up by all these aggregator blogs like Reddit and Slashdot and other sites where programmers gather.

There were many hundreds of comments calling me the worst insults I had ever seen in my life like, “This guy is a raging idiot. These mouth-breathing lunatics with not a brain cell in their heads. These guys are the problem. Obviously, this guy doesn’t know anything.”

It hurt my feelings for about 10 minutes until I realized, “Wait a second. All these people are insulting me but for one, they don’t know me. Two, they’ve never seen a single line of my code. They’re calling me a bad programmer, but they’ve never even seen my work.”

It was on that day, and forevermore since, that I detached from my public persona.

My kid is only eight years old. My advice for him when it comes to the internet is that, “You have your real name, and then you have your internet name.”

The first time he wanted to do an online game, I said, “You have to make up an internet name.” He said, “An internet name?” I said, “Yeah. Your internet name is the one that the people on the internet will know you as because you never use your real name on the internet.”

The point is, I like this disconnect between your public self and your private self. If somebody is attacking your public self, it’s like a cardboard cutout of you. It’s not the real you. In fact, if you were sitting there watching people throwing tomatoes at a cardboard cutout of you, you might actually think it was funny. It’s not the real you. The real you is sitting there, observing the spectacle. This is how I think of public persona.

But when you detach from your public persona, it also means you can’t take praise personally either. So in any comments, in anything that I’ve put out online, I don’t take any of it personally. If people are attacking it, I go, “Huh, cute.” If people are praising it, I go, “Oh, cute.” I’m just detached from it.


Derek, what I love about your style, both in your videos and tonight is that you’re very present. Through this evening, I’ve been able to feel you palpably. Can you give some tips? What do you do to stay present?


Thank you. It’s short and intense.

I think if I had to do this for more than this short amount of time, I’d probably have to turn off. There’s an on-face and off-face. There’s on-face, which is this. Like if you’re smiling, and then you hang up the phone, and you go [off-face motion]. The muscles in your face drop.

Nobody has ever asked me this before, and I’ve never said this before, but whenever I do these video interviews, I do a very unnatural thing, which is [pointing to screen], I only look at this blue, little dot on my screen. I haven’t looked at anything else except when I’ve had to look over to my notes.

Even when doing these video interviews, maintaining eye contact helps so much. I’m not a naturally social person, so a lot of the social things I’ve learned are from books. I’ve actually read most of these books on how to be social, and put a lot of their advice into practice. It doesn’t come naturally.

I practiced and tried these techniques I learned. I went to events when I was with CD Baby. I had 200,000 musician clients. When I went to an event in New York City, there were 250 clients who wanted to meet me. Sometimes, they would actually queue up.

I thought, “How can I do this in a sincere way that’s not faking, but it’s not completely authentic?” To be completely authentic, I might have had to say, “I don’t want to talk to any of you. I’m going to go back to my room to read a book.” But that would be too authentic. Instead I tried to think of ways that I could do it.

That’s why I learned these things about asking people questions, maintaining eye contact, and other little tricks. Those techniques actually work, and they keep me focused on the present. They keep me focused on the other person, which then keeps me present.


Well, with that, I’m going to call to an end today’s really, really fantastic meeting. I know everybody has had a good time. Thank you very much.


I really meant it. I actually do enjoy hearing from everybody. I put aside time to answer every single email I get, and I like it. It’s one of my favorite parts of my day.

I really loved living in Singapore, and I miss it a lot. This is how cheesy it gets. Every morning, I drink a type of tea that’s made by this company called Singapore Breakfast Tea. It actually smells like the Singapore coffee shops. So I especially love hearing from people from Singapore.