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Image for Derek Sivers: Lessons from Making (and Giving Away) a Fortune

Derek Sivers

Lessons from Making (and Giving Away) a Fortune

Derek Sivers shares what he’s learned from his wildly diverse life, including how to set better goals, overcome wrong instincts, and separate what’s useful from what’s true.

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Derek Sivers is one of the most interesting thinkers of our time.

He's been a professional touring musician, a circus performer, and a successful entrepreneur who sold his company for millions.

And that's where things start to get really interesting.

Because Derek didn't keep the proceeds from the sale of his company. Instead, he donated them to charity.

In this show, he'll explain why he did that. (He'll also share what his friends and family thought when he did).

Since selling his company, Derek has spent his time exploring the world, doing public speaking, and writing. He is now the author of five books, and I'd absolutely recommend all of them. They are terrific.

Derek has a gift for condensing big, powerful ideas into short, memorable phrases. Some of his quotes have been hugely influential to many, including me. Just Google his phrase "Hell Yeah or No" to see what I mean. It's a phrase I personally reference often.

During our show today, Derek spends some time sharing his gifts with us.

You'll find that Derek has a fascinating outlook on life and how to live it. He's also very generous in sharing the things he's learned through his studies, experiences and travels.

We'd like to share in that generosity by offering you a chance to win Derek's latest book, which is titled "Useful, Not True."

We're giving away 25 copies of the book to listeners like you. Don't forget to sign up for your chance to win.
  • How to overcome self-limiting beliefs (19:44)
  • Why we over-value our instincts, and what we should do instead (22:43)
  • A new (and more useful) approach to setting goals (30:20)
  • The one thing that all of his heroes have in common (41:14)
  • His thoughts on what the best thing is that you can pursue in your life (12:11)

FRANK BLAKE: Derek, welcome. It's great to have you on Crazy Good Turns.

DEREK SIVERS: Thanks, Frank.

FRANK BLAKE: I'm going to start with a general comment and then some general questions before we get into your new book.

My general comment is I have enormous appreciation and respect for people who can put big ideas into compact, short statements.

It's a little like being at the eye doctor when you're going through and something's fuzzy, fuzzy, fuzzy.

Then someone clicks and it goes, "Whoa! I never understood it that way, that is brilliant."

You have done that consistently through each of your five books. I will get, hopefully, a chance to talk about all of them or most of them during this podcast.

That in my mind is a crazy good turn of its own.

DEREK SIVERS: Thanks, Frank.

FRANK BLAKE: Because any of the listeners who pick up your book and read it are going to go, if they're like me, they might go the first read is, "Yeah."

Then the second is, "Oh. Whoa! Never looked at it that way. That is really helpful."

You do that consistently and thank you for that.

DEREK SIVERS: Thank you. That's the ultimate compliment. I really appreciate that.

FRANK BLAKE: It's very true, but it's going to lead ... I have a couple of general questions before getting into a conversation around your book.

One of the questions is from that, I looked on your site on your short self-description.

Your short self-description is, "As a musician, circus performer, entrepreneur, and speaker," those are the four things.

All I totally get, and are totally valid.

What's surprising to me that's missing is "writer," because I think you're a brilliant writer.

Why isn't writer on that list? Or you just, that just didn't occur to you at the time?

DEREK SIVERS: Wow, that's a good question.

I have always thought of writing as a side effect of just sharing what I've learned as I go through the path.

FRANK BLAKE: Yeah.

DEREK SIVERS: My years in the music business, and then on the side I share what I learned.

Then my years starting and growing a company, and sharing what I learned.

Then the philosophical midlife crisis, "Oh my God, what am I doing now that I've sold my company?"

Then I share what I've learned.

But I never really thought of myself as a writer until more recently, after writing a few books. I went, "Oh, I guess I'm a writer now."

But it always felt like a side effect, not the primary aim.

FRANK BLAKE: Well, that's interesting. You are an outstanding writer.

Another question that that led me to was is there a linkage?

I think there is a linkage amongst your books, of both expansion of themes and some through themes.

Do you see that with your own career, as disparate as it is, to say musician, circus performer, entrepreneur, speaker, that there are actually some through lines?

Some things that, because you're a musician, you write differently or you think. What's the through line if there is any on those four things?

DEREK SIVERS: Ooh. Definitely.

The main through-line is I'm very personal, meaning I'm doing this all for personal intrinsic reasons, not extrinsic, external motivation.

It's never that I was trying to get rich, or I was trying to, I don't know, get girls, or something.

I was always trying to see what I could become.

I think as a teenager, I learned about Abraham Maslow and his pyramid of self-actualization. It really reached me.

I went, "Yes, that's what I want to do. I want to try to be ..."

I was going to say everything I could be, but that's not accurate. Not everything.

But I wanted to challenge myself to see if I could be a successful musician, to make my living just making music. That in itself is a good challenge.

FRANK BLAKE: Right.

DEREK SIVERS: First you have to be great at music, then you also have to be great at networking.

Then you have to be in a place where things are happening, you have to learn about business.

There's a whole bunch of skills that go into being a successful musician and I wanted to see if I could do that.

For 15 years of my life, from the age of 14 to 29, that was my sole focus. I was just mono-maniacal.

You couldn't get me to hang out and party. I didn't relax, I didn't vacation.

I was just mono-maniacally focused on becoming a successful musician from 14 to 29.

But then I accidentally started the business and I pivoted, as they say now.

Now I was helping other musicians. For 10 years, I was running this thing that was helping my fellow musicians.

Then I became mono-maniacally focused on that thing about helping other musicians, but it was still related to this self-actualization idea of let me see if I can create a successful business to help these musicians.

Every day, I would wake up thinking, "How else can I help my clients? How can I get better at helping them?"

That was my focus for 10 years.

Then after selling the company, I did the default thing at first where I thought I was just going to jump right into my next venture.

I did that for just a few months before I caught myself and said, "Wait, that's not being everything I could be. That's just continuing on the same trajectory I've been on."

Well, I am broader than that. What else could I do?

More recently, I've set out to find a deliberately different path to challenge myself to do what doesn't come naturally to me.

Does that make sense?

FRANK BLAKE: Yes, it absolutely does.

Anybody, again, with the audience who picks up one of your books, I'm sure you're going to do the same thing I do which is underline it furiously, and then lift quotes to your own journals or pages.

In one of your books, I think it's the How to Live, you have a great discussion around mastery and the importance of mastery.

That felt like a foundation of what you were describing. Maybe you want to comment on that.

Look, I could go through ... I have a temptation to go, "God, this is a brilliant insight, expound on it," but the mastery comment was brilliant.

DEREK SIVERS: Well, Frank, that's amazing that you picked up on that particular chapter.

Audience, for anyone listening, the whole point of the How to Live book is it's 27 chapters that are supposed to be trying to make equal arguments for why this chapter has the correct way to live.

Then the next chapter will say, "No, no, no, no, no, this is how to live," and it will disagree with all the other chapters.

You picked up on something, it's really impressive that you got that.

The mastery chapter used to be twice as long up until literally the week before I published it. I gave it to a few dear friends to, "Hey, I finished my book, check it out. What do you think?"

One of my good friends said, "Derek, I know you're trying to be neutral and treat all of the 27 chapters equally."

She said, "It's really obvious that this mastery chapter is the one that you are biased towards."

I deliberately chopped it down a week before publishing to make it half the length and try to make it more neutral.

But yeah, I guess you noticed that that point is still shining through that one has is extra dear to my heart.

FRANK BLAKE: Well, I could do it violence in replicating, but it is something to the effect of, "Mastery is the thing to target because it's the best goal because you can't buy it, you can't fake it, you can't inherit it. It is something you yourself build and own."

DEREK SIVERS: Actually, I'll give Arnold Schwarzenegger some credit on that.

It's a quote I thought I heard from him, though I can't find it anywhere so who knows, maybe I dreamed it.

But it said something like, "Fitness is the best goal because nobody can inherit it, nobody can buy it, nobody can cheat their way to it. You can't fake it."

Or something like that. That quote had been in the back of my head for 20 years.

I realized that, for mastery, it's the ultimate status in a way. If you've mastered something, there's no way that you could have shortcut that.

You couldn't just get rich from your parents and spend money to become a master.

Even if your parents buy you the best tutors, you still have to do the work to master something.

Nobody can steal it from you. It's the ultimate source of pride and status if that matters to you.

FRANK BLAKE: Keeping on a couple of more general themes.

I'm also really interested in your experience as an entrepreneur from two perspectives.

One, you built a successful company and sold it for millions of dollars.

But most interesting particularly for this podcast is what you did after you sold the company.

You might want to describe that to our audience and the why's behind it.

DEREK SIVERS: Okay. Well, I'm going to try something new. I'm going to tell a little fable.

Imagine that you love cookies. You are a cookie aficionado and you learn to bake cookies, and you get cookies from around the world.

As much as you love cookies, as a certain point you have more cookies than you'll ever be able to eat. They're all in your pantry, and they're in your fridge, and they're in your freezer.

Then somebody shows up and says, "Well, congratulations. Dolly Madison has now granted you a lifetime supply of cookies.

"We're going to bring 1000 cookies to your door every day from now on for the rest of your life."

You would probably wisely come to the same conclusion that you don't want 1000 cookies to show up at your door every day. That's more than you will ever be able to eat.

That's silly, please give them to someone else.

As much as I love cookies, there's a limit to how much somebody can eat. You could give away the cookies to people who really needed them.

That's what happened to me with my company.

I was the sole 100% owner. I had no investors, it was just me. The company was already very profitable.

I had $4 million in my personal account. That was after I had paid off my mortgage and my parent's mortgage, and the car, and all that stuff.

There was nothing else on earth I wanted to buy and that's when I felt done with my company.

I felt ready to make a change in my life and do something else, and I had this offer to buy my company for $22 million. I went, "Wow! Great. Okay."

But I had few months to think longterm, "What the hell am I going to do with $22 million?"

In fact, I've seen some people, and I'm sure you have too, that end up doing stupid things when they get too much money.

There is such a thing as having too much money. It throws off your whole perception of the world and your perception of money.

People waste it and they act stupid when they have too much.

I thought, "I don't want to be one of those people and I have enough."

This $4 million is plenty because you just stick that in an investment fund and you could just live off the interest for the rest of your life. What am I going to do with this 22 million?

Luckily, my lawyer that was doing the deal for the sale had a background in tax law.

He asked, "What are you going to do with the money?" I said, "Nothing. I'm just going to give it all away."

He said, "Are you serious?" I said, "Very." He said, "How serious?" I said, "Very." He said, "Irreversibly serious?" I said, "Yes."

He said, "Well then, we can structure this deal so that $22 million never touches your hands, that all of it will go to a charitable trust."

I said, "Yes, that's what I want. Make it so it just doesn't touch my hands, I don't want it."

It all went into a charitable trust that pays me a trickle for the rest of my life.

The minimum allowed was 5%, so obviously that's a sweet trickle that's still more than I need.

Yeah, then it all goes to charity and never touched my hands. It's not that I'm so altruistic.

It was just logical, like my story about the cookies.

FRANK BLAKE: Well, with all deference, I've got to say, I know a lot of entrepreneurs and a lot of very philanthropic folks, but I don't know anyone who sold his or her company and gave the proceeds away.

DEREK SIVERS: But you can see how it makes sense, right?

FRANK BLAKE: I'm sure that you had, and maybe this is a good segue into belief systems and reframing, but I'm sure you had a lot of folks around you who were going, "Derek, Derek, slow down, think about that. You might not want to do that.

"Life, there are lots of bumps and bruises in life, it would really help you to have all that money. I can think of things for you to do." Weren't there people like that around you?

DEREK SIVERS: In short, no.

Most of my friends, maybe because of my background, are musicians or artists that only have a few thousand dollars saved up.

To them, I was already the ridiculous multimillionaire that used to be one of them, but they still find it kind of alienating that I had $4 million in the bank.

I think all of my friends agreed that $22 million was unthinkable.

I had just one friend that, when I said, "What would you do with this much money?"

Only one of them said, "You know, that's not a lot of money. It's going to disappear pretty fast."

But no, the rest of my friend circles felt that was an unthinkable windfall. I had good peers.

FRANK BLAKE: I would put it down as a crazy good turn.

I would say that's a crazy good thing to do for other people, so thank you for that. Thank you for the perspective that views it as logical.

That is probably a good segue to your current book because one of the things I've learned from you is pay attention to the first sentence in a book.

Your first sentence in the book is about reframing and the importance of reframing.

The book is titled Useful Not True, which is a great phrase on its own, and it's about reframing. Maybe give the context of that and what got you to write this book.

DEREK SIVERS: Sure. There's so many times in life when I've heard friends feel defeated.

Either defeated in a momentary situation saying, "Well, that's just the way it is, there's nothing you can do about it in this situation. You're just going to have to pay the guy even though it's not fair."

I think, "No, that's not the only way to look at this." That's just one way to look at this.

There are so many others. If you've ever read books on negotiation or reframing in life, you know that there's always another way to look at this.

There's a perspective where you have more options, you have more power.

Then it even goes to life-size, where I have friends who say, "Well, I'm just not one of the lucky ones. I've just never been good at that. I've never been good at this. I'm just not that kind of person."

I think that's a limiting belief. You're deciding in advance that that's an absolute fact, but that's not true. That's just one way of looking at it.

There are some things in life that are absolutely true. A square has four sides. I am clapping my hands right now. That's just a fact.

But so much of the world we live in is a social interpersonal perspective world in our head, where we see a situation and filter it through our beliefs, and decide that that's just the way it is.

But that's not the only way to see it.

So many successful people seem to get successful because they just have a different perspective.

They look at the same situation that everybody looks at thinking it's a dead end and they see a trapdoor. They see that this jail cell is not inescapable. "With patience and a spoon, I can get out of here."

Or, "This is not a dead end. I could climb that wall."

I'm saying this metaphorically of course, but you can imagine it applies to any personal or professional situation you find yourself in.

The beliefs are what changes everything. The actions follow from the beliefs.

As soon as you change your belief and change your perspective, the actions are just a follow-on.

I felt that this was a really underrepresented, important point to talk about. I spent two years diving into the subject.

But of course, since I was writing a book about beliefs, I had to go learn more about it, so I ended up reading eight books about religion.

I read the Bible cover-to-cover, every single sentence on every page. I read the Bible and really put a lot of thought into that.

I also read two books about Hinduism. I read a couple books about Islam, a couple books about Judaism.

I read books about pragmatism and skepticism.

I just kept learning all around the subject about beliefs and tried to condense everything I learned into a very powerful little 100-page book.

FRANK BLAKE: That it is. Again, I could start just quoting from the book, but I'll give another quote that I think is really interesting.

You say, "Your wisdom has to go against your instincts."

I read something like that and I think about it, and I go, "God, that's really profound."

What triggered that for you? Was it an event that triggered that for you?

Was it a process of thinking through how we get to our belief systems? What's the background for that?

DEREK SIVERS: I think I noticed that all of my best perspectives did not come instinctually. They came after my instinct had passed. Your instinct is just a reflex, like your knee kicking when the doctor hits it with the hammer.

Your instinctual response to something is just a dumb, stupid reflex. It should not be given too much value. Then when you take a second to think, that's when you come upon the better perspective.

Say, for example, if somebody-

FRANK BLAKE: We're taught the opposite of what you said, by the way.

DEREK SIVERS: Right. That's why I thought it was ... I try to reduce my books down to only what needs to be said.

FRANK BLAKE: Right.

DEREK SIVERS: I don't want to waste people's time with what they already know.

Let's just think of a metaphorical situation where you're walking down the street, minding your own business. Then somebody next to you yells, "Hey, jerk!"

Your instinct is fight. You're like, "Who said that? How dare you! You're the jerk. What is this about?"

You have to take a minute to realize what just happened. That in fact, they weren't yelling at you.

Or they thought you did something, but it was the person behind you. Or you find that the person has some mental issues and they're yelling at ghosts and it has nothing to do with you.

It takes a second to come to a wiser perspective. Your impulse is not wise.

Same thing with other aspects in your personal life. Somebody cancels last minute on a personal date that you had.

Your impulse is, "You jerk! How dare you."

It takes a minute to use a little empathy and realize that, okay, they must have something going on. This is nothing against me. Our friendship is still strong, this was not an insult.

Same with business situations.

There are business situations where you're in what feels like a bind and everything in your instinct says, "I am screwed. I am so, so screwed. There is no way out of this."

Everything in your body tells you, "This is just bad. This is horrible. This is the worst thing that's ever happened to me!"

It takes a second to get past that and say, "Okay. How else could I look at this? What could be great about this? How could I use this to my advantage?"

Those wiser thoughts are never instinctual. It takes some deliberate acceptance that there are multiple ways to see this situation and you're going to find a good one.

FRANK BLAKE: You have an interesting discussion on perspectives and the kinds of perspectives. Your beliefs, it's not entirely nihilistic, you're giving a framework for things that are more or less helpful.

On the more helpful side, you have a great set of perspectives.

The one that caught my eye though was you phrase it both as selfish and selfless, so that both of those are important perspectives. Can you explain that apparent contradiction?

DEREK SIVERS: Sure. We both know people that take either of those to a fault. Of course, it's possible to be selfish to a fault.

We see many examples of that in the world around us. But it's also possible to be selfless to a fault, where you're always making yourself the martyr in an unsustainable way.

It's important to notice that neither one of those is necessarily right or wrong. Sometimes the selfish thing is the right thing to do.

For example, leaving an abusive relationship. Some people don't leave an abusive relationship because they're too stuck in a selfless mode that they've just told themselves through and through, "Anything selfless is good, anything selfish is bad."

But sometimes you need to value yourself enough to do the selfish thing, which I think it's better to reframe it as self-worth.

It's having some self-worth to value yourself as much as you value others, instead of always less than.

It's important to try to see these things neutrally as just different perspectives without clicking into judgement mode immediately and calling them right and wrong, but to just see them as different perspectives.

FRANK BLAKE: Share a little bit, your process for writing a book like this. Because as you say, you greatly understate I think the work involved in condensing a lot of deep thoughts into 100 pages.

DEREK SIVERS: Thank you.

FRANK BLAKE: How does that work process go?

DEREK SIVERS: It's the old quote that says, "Forgive me for this long letter, I didn't have time to write a short one."

FRANK BLAKE: Yeah.

DEREK SIVERS: I figure it's my duty, it's my job to not waste the reader's time.

I figure everyone is too damn busy to hear my thoughts unless I can really make them as succinct as possible so that every sentence is worth your time.

My process is to first dump out everything I have to say on the subject. My How To Live book was 1,300 pages long when I finished my rough draft. I went, "Okay."

FRANK BLAKE: Wow.

DEREK SIVERS: "Now I've said everything I want to say."

FRANK BLAKE: By the way, it's a phenomenal book.

DEREK SIVERS: Thank you.

FRANK BLAKE: I don't know if you have favorites amongst your books, but that's a really brilliant book.

DEREK SIVERS: Thank you.

FRANK BLAKE: They're all brilliant, but that one's extra.

DEREK SIVERS: I'm so proud of that How To Live book that I think if I did nothing else with my whole life but that one book, it would still feel like a life that was worth living. That I'm very proud of it.

But yeah, then my job is to take this 1300 pages and then go through critically.

Does that paragraph really need to be there? Isn't that redundant? Or isn't that obvious? What's the most surprising point on this whole page?

Well then, can't I just say that surprising point and skip the rest of the page?

It's ultimately I want to write a book that only takes an hour or so to read. And blows your mind as much as a 10-hour book would have.

I think this is also coming from the fact that I do read a lot of nonfiction books that are too long. We've all felt the pain of reading a book that feels-

FRANK BLAKE: Amen.

DEREK SIVERS: ... in the end like that should have been an article.

FRANK BLAKE: Right, right.

DEREK SIVERS: You really could have said that in 10 pages.

FRANK BLAKE: Yeah.

DEREK SIVERS: I try to be the guy, then, that does say it in 10 pages instead of 300 pages. Yeah, that's all.

FRANK BLAKE: I'm jumping around a bit among your books, but Hell Yeah Or No I quote all the time.

First, for the basic concept, but there is also something I think is really ...

There are lots, but there's one quote in particular that captured my interest, which was about the "purpose of goals is not to improve the future."

Which I think is an unlock of enormous value. Maybe you describe that a little bit to our listeners.

DEREK SIVERS: Yeah. That one blew my mind and I think about it all the time still. Which was realizing that we think of goals as somehow shaping the future.

"If I have the goal to be healthy, then in the future, I will be healthy. If I have the goal to be smarter, then I will be smarter."

But, no. The goal itself does not change the future at all because there is no such thing as the future.

It's what we call our imagination, it doesn't exist yet. That's why it's the future. It literally does not exist.

The only thing that we can do something about is the present moment. It's your actual actions right now are the only things that are real and in your control.

That's when I realized that a good goal is just one that makes you take effective actions in the moment.

Right now, today. It makes you jump out of your warm bed or your comfortable sofa and go do the thing you need to do, to take the action. That's a good goal.

Of course, like all of us, I have felt the pain of setting a goal that seemed good in theory, but didn't actually make me take better actions.

I felt like an idiot. Like, "Oh, man, but that was a good goal and I'm still not doing it."

That's when I realized, wait, then that wasn't a good goal. A good goal should only be judged by, does it make you take action right now?

Goals that are too lofty like, "I'm going to revolutionize the world," don't make you take action because they're not specific enough.

I realize that the best goals are the ones that are so specific like, "I'm going to practice my Chinese through this app every day for 30 minutes."

That's my goal. Not fluency, I'm going to focus on the action.

I'm sorry, I didn't need to do a specific there, we've all got our own specifics.

FRANK BLAKE: The specific is actually helpful. It actually leads me to another question.

I recommend all of our listeners go to your very short URLs that you lay out for different parts of your books and thought processes.

But you have a section on what you're doing now and one of them that I wanted to ask you about was you said you're enamored with China.

What is it that's captured your imagination on that?

DEREK SIVERS: All right. Any Americans listening to this, it's going to blow your mind.

It was only 13 months ago that I went to China for basically my first time.

Actually, you know what, I'll give a background. 15 years ago, I went for a week and it was awful. It was nasty, and stinky, and full of rubble, and smoke.

It felt very much like a Third World country, like you'd expect a Third World country to be. It was not pleasant.

15 years ago, even as I was living in very beautiful, refined Singapore for a while, people from mainland China had a reputation of being rude, and shouty, and spitty, and bossy, and just very uncouth. I kept that impression of China.

I thought of China as a very rough, Third World, aggressive, uncouth, uncivilized place.

Then just 13 months ago, my boy had his spring school holiday and asked if we could go to China.

I went, "Really? You want to go to China?" I was like, "Okay, I'll show you."

I took him there expecting to show him how rough it is.

We flew to Shanghai, took the Maglev subway at 300 kilometers an hour from the airport to Central Shanghai.

Got out of the subway station at Shanghai and I stepped out into this pristine, futuristic, beautiful, civilized, extremely pleasant, harmonious place where people are smiling and happy. The place is amazing.

And quiet because all of the cars are electric and the air is clean. It's adorable. It's beautiful.

It's like you would think of going to a Swiss village for your first time. I think of Switzerland as the place that I think of, as the most pristine, beautiful, harmonious, wealthy place on Earth. China outdid it.

The top tier Chinese cities, by which I mean Shanghai, Shenzhen, Chengdu, the top cities in China, I don't know about the rest of the country because I haven't been everywhere, but oh my gosh, they're so beautiful and so pleasant.

The people are kind. It just works. It's a happy, harmonious place that blows my mind because it went against every prejudice I had.

It went against what we're told about China. It went against everything I knew. When you're actually there in-person, you see this really amazing, wonderful place.

Then I went back three times in the past year to go meet with people that have emailed me over the years.

People that are from and raised in China, but that speak English and have emailed me after reading my books, so I went to go meet with them in Shenzhen and in Chengdu.

They're wonderful and they're all really happy. Saying that, "Life is great here. Things are wonderful and we really like it." I see it. It's easy.

I'll finish with this. To me, the metaphor I've started telling friends is you know when you're riding your car or bike on a rough road and it goes [rough vibration].

Then you get onto a decently paved road and there's still this [vibration] as you ride.

Then every now and then, you get onto a newly paved road and your [vibration] turns into shhhhh...

You go, "Oh, gosh, I thought the previous road was paved okay, but this is extra nice." That's what going to China feels like to me. It's extra nice.

FRANK BLAKE: You mention your son. In what ways has he impacted how you approach your writing or your speaking, or the other things that you do? If at all.

DEREK SIVERS: I try to share everything I've learned on the pessimistic assumption that I could die at any minute.

I want to get it all out there so that, if he wants to go back and see more about his dad, that it's all out there.

That everything I ever learned has been shared in some permanent form.

FRANK BLAKE: I will say, as a side note to that, another crazy good turn. You are extraordinarily generous with your commentary.

When you read books, our listeners could go to your site and find the notes that you've made to the books.

Which honestly, having read some of the books and your notes, your notes are more interesting than the book. But a very generous thing to do.

Are there books that you've read that you've said, the most important books that you've said, "This has reoriented how I think about the world?" Would would they be?

DEREK SIVERS: Yeah. If the listeners do go to that page on my website. It's S-I-V-E.R-S/book.

Or if you just go to my homepage, you search my name, or search DEREK SIVERS book notes. There are I think 450 books there with my notes.

You'll see a list of the book covers and the titles. Then for each one, you can click in to see Read Notes and read all of my detailed notes from the book.

FRANK BLAKE: Do it. Honestly, for our listeners, do it just for that. Do it just to read your notes on the books. They're great.

DEREK SIVERS: Thank you. Hopefully it doesn't replace the book because I'm not trying ... They're not summaries.

FRANK BLAKE: For some of the lazier people, it might do that.

DEREK SIVERS: I know. I feel a little bad though when they say, "Hey, thanks for posting the notes. Now I don't have to read the book."

FRANK BLAKE: No, no, no.

DEREK SIVERS: I say, "No! You've missed the whole point."

FRANK BLAKE: No. I'm with that group sometimes.

DEREK SIVERS: They aren't book summaries, but they're my extraction of what I thought were the most interesting ideas from this book. I'm doing it for my own sake so I can reflect on it later.

So I don't have to reread that whole book again, I can just remind myself of that book's most interesting points and reflect upon them more.

But to answer your question. I sort that list with my top-most recommended books at the top of the list.

If you just start with the top, you'll see You Can Negotiate Anything by Herb Cohen, which is not a shallow book about getting a better price on something. It's a surprisingly deep book that gets you into the mindset that all of life is negotiable.

This is not etched into the 10 Commandments on stone tablets. Any situation you see is negotiable. You can always find an angle that's more to your satisfaction in any situation.

He even lays out some extreme examples. There's an extremely colorful example of a prisoner in solitary confinement that wants a cigarette from the guard.

He said, "I'll bet you think there's no way that prisoner has any leverage to get a cigarette from the guard, right?" He actually lays out how he would do it if he were that prisoner.

Awaken the Giant Within by Tony Robbins, totally changed my life. Stumbling on Happiness. The Paradox of Choice.

These books that changed the way I live and I think everybody should read, I put those at the top of the list.

FRANK BLAKE: Okay, perfect. Is there someone who in particular inspires you today?

That you go, this is a life being led in what you might think is the best way to lead the life?

DEREK SIVERS: Wow. Kevin Kelly is awfully close.

Wow. Frank, that's a really good question. I would need five minutes of awkward silence to come up with a better answer.

Let's do this. If anybody wants a better answer, go email me and I'll think of a better answer by tomorrow.

FRANK BLAKE: Okay.

DEREK SIVERS: If anybody wants to email me, I'll think of a ... That's a really, really question.

I should think of that more often. Seth Godin is such a role model for me.

FRANK BLAKE: Seth has been a guest.

DEREK SIVERS: Oh, good.

FRANK BLAKE: Yeah.

DEREK SIVERS: I so admire him. Same with Kevin Kelly. But gosh, there's so many others.

Actually, if you don't mind me rewinding to one of your first questions.

FRANK BLAKE: Yeah.

DEREK SIVERS: You asked about me thinking of myself as a writer. It was only more recently when I realized that all of my heroes are writers.

They're not entrepreneurs. They're not athletes. They're not even musicians anymore, unfortunately. They were for many years.

But these days, all of my heroes are writers.

That's when I realized I think that's the direction I'm facing. It's like metaphorically, whoever you're looking up to, that tells you what direction you're facing.

FRANK BLAKE: Wow, yeah. That's a great point of view as well. Back to the entrepreneur, I have one, this is a random question.

I'd love for you to share with the audience how your company, CD Baby, why somebody like me in the hardware business would actually have known what you did with that business that made it exceptional?

DEREK SIVERS: Well, it helped that this was just a record store. It was a music distribution company.

It was fun. This is not financial management. This is not serious business. It's a little bit of levity.

I created a little online store way, way, way back. This is 1997, back when nobody did this. I made a little online store that, at first, had this default settings.

Things like, "Okay, your order has been shipped. Here's your order number. Thank you for your business."

After a couple months I thought, "I can do better than that. That's so dry." This is a chance to make someone smile. This is an opportunity, it's an interaction.

I took 10 minutes and wrote a silly little email that said, "Your CD has been placed onto a satin pillow and our packing specialist from Japan had gold-lined gloves, that we placed it into a special gold box which is being shipped to you on our private CD Baby jet today.

"The whole crowd cheered as the jet left. We're putting your picture on our wall as Customer of the Year.

"We're all exhausted after this, but we want to thank you for coming. We're all really looking forward to the day when you ever come back to our little store. We'll all be waiting for you."

I just wrote this silly thing in 10 minutes and I made it the default shipping confirmation email.

People thought it was so weird and funny that they started sharing it on social media and posting it on their blogs. Then Seth Godin even put it in his book, I think Purple Cow.

Thousands and thousands of people came to CD Baby that otherwise wouldn't because of my silly little shipping announcement email.

I tried to do that in other ways, too. You could pay for things in cash or you could pay for things in pizza.

I said, "Okay, if you don't have enough cash, here's the local phone number to the local pizzeria. We prefer pepperoni pizza. If you need to pay for something, call the pizzeria and have them send CD Baby a pizza and we'll consider that as payment." Things like that.

FRANK BLAKE: Did anyone ever do it?

DEREK SIVERS: Oh, many times. Yeah, it was wonderful.

FRANK BLAKE: Really? All right.

DEREK SIVERS: Oh, yeah.

FRANK BLAKE: Okay.

DEREK SIVERS: Because it makes people laugh. They're looking at two options.

They could pull out their Visa card and give it to me directly, or they could, oh my gosh, call a pizzeria.

Is this for real? Let's test it. Whoa, okay. "Supreme's Pizza." Hi, I want to order a CD Baby Pizza. "Okay, no problem. How many do you want to order them?"

People would test it to see if it worked and it did. Then it makes them both happy.

One of my favorite ones was there was a customer who filled out ... In the special request box we sometimes see at the end of an order, it says, "Any special requests or comments?" He said, "If you have a squid, please include it with the order. If you do not have a real squid, then a rubber squid will do."

He just wrote that to be silly because he was just buying a couple CDs. We just happened to have a squid because some customer in Korea had mailed us an actual shrink-wrapped dried squid that the guys in the warehouse had kept tacked up on the wall.

They went, "Wow. Look, somebody's asking for a squid. Let's send it to them." We included a squid with his order.

He was so blown away that he went on YouTube and recorded a six-minute video telling the story of how CD Baby gave him the squid he asked for.

He was so blown away by that. You just do these silly things. Honestly, it makes everyone happy. It makes you happy doing it.

You're laughing while working. How many of us get to do that? The customer is thrilled and they go, "Oh my God, they just blew my mind."

I think another company that currently does this well is Cards Against Humanity.

It's a silly card game, I believe. It's a card game that's somewhat rated R, let's say. Not rated X, but rated R.

They end up doing snarky, silly things like on Black Friday, they actually raised their prices on Black Friday just as a way of spoofing the world.

It makes them laugh, it makes the customers laugh. People do actually choose to buy things from them on Black Friday at a higher price just because it's ridiculous and funny.

I love these moments. It's a wonderful reminder that when you create a small business, you've got such an advantage over big businesses because you can do small silly things that don't need to please investors.

You don't need to justify yourself to others. You can make it wonderful.

You can make it your own little world where you control the rules and can make the world like it should be in your little sphere.

FRANK BLAKE: Do you know now what your next project is going to be? Or is that a discovery process?

DEREK SIVERS: Ooh. I have a folder on my computer where every time I get super inspired and get a great idea, I start typing furiously and I spec it all it. I say how it's going to happen and how I'm going to do it.

Whether I'm going to program it, how I'm going to find the team, why this is worth doing. Here's exactly how it's going to play out.

I dump everything I can into it. Unfortunately, I have over 350 of these in a folder called "Ideas." Then it's a matter of choosing at any given time which one is worth doing.

It's usually the one that I can't stand not doing any longer. Where I'm feeling psychic pain, my soul is pained at the fact that I'm not doing this, that's the one that has to be done next.

Honestly, I've been wanting to learn Chinese for 20 years now. Even despite everything I said about the country earlier, I just thought it's a rough, dirty, filthy, nasty place, but the language is fascinating.

I really want to learn the language.

Now that I see that it's also an extremely pleasant, wonderful place to be, that just bumped way up my priority list.

Now every day, no matter what, I do spend an hour a day practicing or learning new vocabulary and practicing my Chinese because I want to become fluent.

FRANK BLAKE: Wow. Well, that's a good goal.

DEREK SIVERS: It is affecting my actions in the moment, so yes, it seems to be a good goal.

FRANK BLAKE: I ask everybody who appears on the podcast, who has done a crazy good turn for you?

DEREK SIVERS: Ooh. Let's do Seth Godin actually. Seth has been so generous. I have turned to him in many times where I really felt stuck, or confused, or muddled.

I've emailed him and he so sweetly takes a minute and stops and gives my situation his thought, and gives me some custom advice for me.

Seth Godin blows me away with how generous he is with his time.

If you notice, he almost never has an ask. He just continues to put himself out there and just gives.

Gives his thoughts. Writing on his blog every day Seths.Blog every single day for whatever, 20 years now, there's a post. Amazing.

And even personally. Even the times when I've met up with him in-person, he rarely says anything of himself.

He really seems to enjoy to the core keeping his focus entirely on the other person, whether it's in his writing or his group making, his cohorts that he makes, or even in-person with friends.

There's my nomination.

FRANK BLAKE: Well, I'd say you share with him the instinct to broadcast in the best sense of that word, broadcast your learnings and creativity.

DEREK SIVERS: Thank you.

FRANK BLAKE: It's much, much appreciated. This has been just beyond a treat, having you on the podcast. Really appreciated it.

We will be giving away copies of your book, but what is the best way for our listeners to learn more about Derek Sivers?

I suspect most of them already know, but just in case there are some.

DEREK SIVERS: I suspect most do not. Just honestly, I also, every single day, I answer all of my email.

Sorry, I should say every work day. I spend days going away with my kids. But every week, I answer every email.

I really enjoy it. I hear from people around the world. And it's so interesting to hear from Bangladesh, and Peru, and who knows where.

I just got an email yesterday from somebody from Zimbabwe living in Japan. Oh my gosh, it's so interesting. I asked her why.

I love getting emails from people, that's my point. Go to my website, S-I-V-E.R-S. There is a link that says Contact Me, and please go email me and introduce yourself and say hello.

Because honestly, that's why ... I wanted to meet Frank. Hi, Frank.

But audience, the reason I come onto podcasts like this is because I like connecting with people who listen to them, so email me. That's the best.

FRANK BLAKE: I hope everybody does. Thank you, Derek. This has, as I said, been an unbelievable treat and a real honor. Thank you for your time.

DEREK SIVERS: Thank you. I appreciate it.

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