Long ago, I chatted with Tim Ferriss on Twitter and asked why nobody had turned his podcasts into blog posts.
— Tim Ferriss (@tferriss) December 18, 2015
This article is the result of that conversation and Tim’s podcast interview with Derek Sivers. Like every other thing I’ve ever made, it’s been because I wished somebody else would make it, but just don’t have the patience to wait. So instead of waiting for Tim to write this post, I wrote it myself.
Some of the words below are mine, some are Tim’s and others are Derek’s. Enjoy!
Welcome Derek Sivers
For those of you who don’t know Derek, he’s one of my (and Tim’s) favorite humans on Earth.
Originally, a professional musician and circus clown, Derek (@sivers on Twitter, Derek Sivers here on Medium) created CD Baby in 1998 and became the largest seller of independent music online, totaling over $100 million in sales for over 150,000 musicians.
In 2008, he sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education. He has spoken multiple times on the TED Talks circuit with over 5 million views of his talks.
Since 2011, he has published 24 books, including Anything You Want. While business books are mostly terrible reads, Anything You Want is one of the few business books that I’ve read multiple times and listened to — most recently in Sweden a month and a half ago.
Derek and I first met in 2007–2008 and most often when I call Derek, it’s because I need a sanity check.
When I’m surrounded by people asking me how they should grow their company, I don’t call Derek just to get more options. I call Derek because he’s the type of person who will ask, “Why do you want to grow your company in the first place?”
In addition to asking the right questions (more on that later), Derek is also brilliant at simplifying and breaking things down.
Often, people feel dispensable if what they do is simple and we feel a compulsion to complicate things in order to validate ourselves. We complicate to profit.
This isn’t the case with Derek.
For example, Derek and I were sitting in Times Square on a set of bleachers. I was struggling with how to talk to engineers and on a single sheet of paper, Derek sketched out Sequel and Databases.
You can’t help but admire the willingness to simplify things for greater understanding.
It All Started in a Circus
When Derek was 18 years old, all he wanted was to be a professional musician. Attending Berklee College in Boston, he truly wanted to be a rock star, but he’d settle for making his living from music.
One day in rehearsal, the bass player of Derek’s band remarked that his agent just offered him a gig for $75 playing a pig show in Vermont.
The bass player rolled his eyes and said, “I’m not gonna do it. Do you want the gig?”
“Fuck yeah!” replied Derek. A paying gig?
Derek took the gig playing the pig show in Burlington, Vermont. He could have cared less that he had the cost to travel to and from the show was roughly equal to what he was being paid.
The next day, the agent called Derek again to play another gig, this time at an art opening. He spent another $60 for a bus ticket out to western Massachusetts to make $75 at the opening, but this time the agent was there. The agent was so impressed that he pitched Derek work as a circus musician. He’d still make $75 per gig, but with the circus, he could do three gigs per week.
Derek said yes to everything.
Early in your career, you say yes to everything. You just never know which ones are the winning lottery tickets.
For Derek, the circus was his lottery ticket.
At 18 years old and with no stage experience, Derek slowly progressed from playing music between acts to eventually becoming the ringleader MC of the entire circus. If you would’ve attended any of those early shows, you might have thought this 18-year old was running the entire circus.
For the next ten years, Derek did over 1,000 shows and eventually bought a house with the money he made playing with the circus.
Ten years of stage experience and so many opportunities came from that one little pig show in Vermont. The only reason he started turning down circus gigs was because CD Baby started to grow to a point that he had to dedicate more time to it.
At first, Derek went up on stage thinking that everybody was judging him. It took twenty gigs before Tarlton, half of the husband-wife pair who actually ran the circus) pushed Derek to “give the people what they came for.”
The audience loved it.
“Now that I’ve been on stage thousands of times, it’s really sunk in. You get on stage to give the audience what they came there for. That was my biggest lesson learned and luckily I learned that early on, when I was 18.”
But that wasn’t the only way Tarlton helped Derek see himself differently: she gifted him Tony Robbins’ Awaken the Giant Within when he was 19, which totally changed his life. It turns out, this was exactly the same age and time that I read the exact same book.
Tarlton and Derek had been working together for a year or so when Derek was devastated by an emotional breakup. When he told her about the girl, she told Derek that if some woman doesn’t see Derek for who he truly is, that’s not his problem.
The first hundred or so times she told him, Derek just thought she was being considerate. It took about a year of hearing Tarlton constantly reminding him of who he actually was (not just how he saw himself), before it finally sunk in.
“You are whatever you pretend to be” — Kurt Vonnegut in Mother Night
Derek realized somewhere in there that you can simply choose to become confident. Even when everything is going terribly and you have no reason to be confident, you can decide to be.
Most of my friends, including Derek, who are successful and trace their confidence back to either/or a specific woman and a specific coach or mentor. It always comes down to one or both.
For Derek, it was Tarlton, and a man named Kimo Williams.
The Standard Pace is for Chumps
Two years before meeting Tarlton, Derek was living in suburban Chicago. He’d decided to attend Berklee College of Music to become a famous musician and two months before he was supposed to leave, he noticed an ad in the Chicago Tribune for music typesetting.
He knew he’d have to do at least some sheet music reading at Berklee, so he called up the number. The voice on the other end gave him an address, a meeting time, and hung up the phone.
At the appointed date and time, Derek rang the doorbell at the address he was given. Unbeknownst to him, this was his future instructor’s way of brushing off the large number of kids who would call his number. The vast majority of them just didn’t have their shit together enough to be somewhere on time.
Much like Derek, Kimo asked important questions.
When Derek first called him and told him he would be attending Berklee, Kimo’s first question was simply “Why?”
When Derek provided the response of his desire to become a famous musician, Kimo replied that four years and nearly six figures in debt was quite a large investment just to learn a few bars of music and some theory.
Simply being on time and prepared for his first meeting with Kimo Williams allowed Derek to graduate from Berklee College of Music in half the time it would take.
Kimo held the belief that the standard pace at Berklee was “for chumps,” since the school had to organize it’s curriculum around the ‘average’ student. Since Derek (or anybody else for that matter) could be smarter than that, he could choose to go as fast as he wanted.
“The standard pace is for chumps.” — Derek Sivers
What followed was an adrenaline fueled 2-hour lesson that had Derek’s heart racing and his mind flying. For four Thursdays in a row, Derek learned 2 years of Berklee’s curriculum.
Upon showing up to campus, Derek was indeed able to test out of most of the first two years of Berklee’s curriculum. To top it off, Kimo had mentioned somewhat offhand, that Derek could buy the books for some of the required courses and take the final exam. Derek used both strategies to cut the time necessary to graduate in half, a lesson that applies to almost all formal education processes.
Relax for the Same Result
Much like me, Derek has been very “Type A,” his entire life. We both naturally have a strong desire to burn the candle at both ends and leave as little as possible to chance.
He was known to his grade school friends as “the robot” because they’d never see him sleep, eat, or do anything other than practicing to be the best musician he can be.
When he was living in Santa Monica, a friend introduced Derek to cycling and he immediately began riding the beachside bike path near his home. True to his nature, Derek spent every single ride huffing and puffing, red-faced, pushing himself as hard as he could.
No matter how hard he rode, it always took him 43 minutes to do a complete circuit on the bike path.
However, over time, his passion for it waned. He found himself less and less psyched to go out on the bike.
Derek started to see it more and more as hard work and found himself less motivated than ever to go out. Not wanting to associate negative feelings with something he loved, Derek decided to make a change: to go for a bike ride and just enjoy himself. He finally took time to look around and take in the ride.
There was no red-face.
There was no huffing and puffing.
It was just nice.
When he got back home he checked his time: 45 minutes.
He learned a profound lesson that changed the way he lived his life ever since as he realized that all of his stress and effort was only for an extra 2 minutes.
It was almost for nothing.
He could relax for the same result.
In life and in business, we often focus on getting the maximum dollar out of each transaction, the maximum second out of every minute, and it’s just not always worth the stress.
After a life of head-down forward charging, Derek reminds himself by observing the presence of mental pain when he’s pushing too hard or doing things he doesn’t really want to be doing. He’s found that it’s always either because he asked the wrong questions or is pursuing the wrong outcome.
Pull, Don’t Push
1998: Derek was in a band but the only way to order Derek’s CD was to mail him a check so he could mail a CD to you. This was simply the easiest way for an independent band or musician to sell their music at the time.
There were a number of other CD distribution sites on the internet at the time, but the only way to get into their system was to get a major label record deal, get in their distribution system, and then you could be sold on the major websites.
Not an easy process.
Derek felt like this could be simpler. He spent $1,000 in setup fees to get a credit card merchant account, figured out how to put a ‘Buy Now’ button on his website, and after a few months of hard work, he had everything set up and ready to go.
A few of his friends (also musicians) asked if Derek could sell their CDs on his website, too.
“People ask me how to grow their business. How they can ‘push’ their idea into the world. I have no idea. I have no advice for those people because I’ve only ever worked on the ‘pull’ method where people ask me to do things for them.” — Derek Sivers
CD Baby just happened because all of his musician friends were asking Derek to sell their CDs on his website.
Eventually, he had to migrate the other band’s CDs to their own website and CDBaby.com was born.
This is a great example of spotting something small, something other people might overlook, and creating an opportunity. Another fantastic example is the automated shipping email that Derek created for CD Baby (it’s a must read).
“Sometimes it’s just these cute little colorful things that you do that set you apart from the rest that make you remarkable.” — Derek Sivers
Don’t Sell Out
For ten years, Derek said “no” to every single person that tried to invest in CD Baby. As a part of the first dot com boom, money was being shoved in his direction from all over and it culminated with MP3.com offering to let Derek name is his price.
He still wouldn’t budge.
At this point Derek was still saw himself as a musician, and less of a business owner. CD Baby was making over $100,000 per month, which easily covered his needs and all of his wants.
He saw taking money as losing control, losing the utopian artist’s dream he’d built at CD Baby, and adding more stress to his life.
All for money he didn’t need.
So he passed on all investment for roughly a decade. Eventually, Derek started passing on most everything that was offered to him.
Hell Yeah, or No
A friend of Derek’s had asked him to attend a conference with her in Australia. Of course, Derek said yes.
Up until this point, it had been Derek’s policy to say “yes” to things whenever he could because, much like working at the pig-show, he never knew when an amazing opportunity would present itself.
After all, it was six months before the actual event. What else did he have to do?
But as the day loomed near and he had to book tickets, he wanted to go less and less.
It was a conversation with Amber Rubarth that changed things for him. She said:
“It sounds like your decision is not between yes and no, you need to figure out whether you’re feeling like fuck yeah or no.” — Amber Rubarth
From then on, if Derek was presented with something and didn’t feel an immediate ‘Hell Yeah, that’d be amazing!” he simply said no.
Most of us say yes to way too many things and the urgent tasks end up overtaking the important tasks. Small, mediocre events fill our days and when you do get a major landmark opportunity, you’re simply too ‘busy’ to take advantage of it.
If you ever find yourself answering the question, “How’s it going?” with a description of how insanely busy you are, there’s a really good chance your life is totally out of control.
The 9-Minute Work Week
One of the most amazing things that Derek did with CD Baby was automate and systematize the company to run without him.
He spent roughly 4 hours on CD Baby every six months, which works out to approximately 9 minutes per week.
But that wasn’t how it always was.
As an INTJ personality type (note: I’m also 100% INTJ on the Meyes-Briggs scale), Derek had built a 20 person team at CD Baby, but everything still had to go through him.
Four years into the company, Derek had built himself into a corner.
It turns out, however, that it only took six months to get out of. For the next six months, Derek worked as hard as possible to teach his staff how to do everything that he was currently doing in the business, all the way down to the hiring. He created a sort of manual for his employees to follow that covered everything they needed to know to run the business.
Books as Mentors
Believe it or not, books guide almost everything Derek does.
Starting in 2007, Derek has taken notes on every single book that he read and, instead of reading the latest article online, he’ll spend ten minutes a day re-reading the notes from a previous book.
But it wasn’t until 2010 that Derek considered sharing them with the world. Which is why, as of today, you can read detailed book notes on every book he’s read since 2007. He’s even given them each a rating so you’ll know which to read first.
He’s even clarified it a step further with the Do This Project where he’ll be turning all of those notes into directives (do this, don’t do that).
Another living reminder that, much like the circus, his site isn’t about him and it’s more important to give the people what they came to see. This is, coincidentally, the exact same advice he gives to people preparing for a TED talk:
“Speak only about what is surprising and skip everything else” — Derek Sivers
How to Be Useful to Others
Do everything in public and for the public.
The more people you reach, the more useful you are.
The opposite is hiding, which is of no use to anyone.
Money is neutral proof that you are adding value to people’s lives.
So by getting rich you’re being useful as a side effect.
Once rich, spend the money in ways that are even more useful to others. Then getting rich is double useful.
Share Strong Opinions.
Strong opinions are very useful to others.
Those who are undecided or ambivalent can just adopt your stance.
But those who disagree can solidify their stands by arguing against yours.
So even if you invent an opinion for the sole sake of argument, boldly sharing a strong opinion is very useful to others..
People given a placebo pill were twice as likely to have their pain disappear when told that that pill was expensive.
People who paid more for tickets were more likely to attend the performance.
So people who spend more for a product or service value it more, and get more use out of it. So be expensive.
How to Thrive in an Unknowable Future
Prepare for the Worst.
Since you have no idea what the future may bring, be open to the best and the worst.
But the best case scenario doesn’t need your preparation or your attention, so mentally and financially just prepare for the worst case instead.
And, like insurance, don’t obsess on it, just prepare and then carry on appreciating the good times.
If you ever watched the VH1 Behind the Music, you know that like every single success story had that moment where the narrator would come in and say “and then, things took a turn for the worse”, so fully expect that the disaster to come to you at any time.
You have to completely assume that it is going to happen, and make your plans accordingly. Not just money, but health, and family, and freedom. You have to expect it to all disappear.
Besides, you appreciate things more when you know this may be your last time seeing them.
Own as Little as Possible.
Depend on even less.
The less you own the less you’re affected by disaster.
Choose Opportunity, Not Loyalty.
Have no loyalty to location, corporation, or your last public statements.
Be an absolute opportunist. Doing whatever is best for the future in the current situation, unbound by the past.
Have loyalty for only your most important human relationships.
Choose the Plan with the Most Options
The best plans are the ones that lets you change your plans.
For example: renting a house is actually buying the option to move at any time, without losing money in a changing market.
For maximum options don’t plan at all.
Since you have no idea how the situation or your mood may change in the future, wait until the last moment to make each decision.
Rapid Fire Questions and Answers
What is the book you’ve given most as a gift?
A Geek in Japan by Héctor García
What $100 or less purchase has most positively impacted your life in the last six months, or recently?
I took my 3-year-old kid to a cafe that had a huge box of toys, little figurines, cars, dolls, monsters, and he was in the zone for 2–3 hours, completely engrossed. So I was like yeah, I can’t push my minimalism on him, so that night I went onto eBay and found someone selling a huge box of old used toys, just like that. You know, figurines and cars and stuff. 20 bucks. Endless hours of entertainment since, best $20 I spent in a long time.
Do you have a favorite documentary or movie?
No, I really don’t watch hardly anything. I really prefer books as my medium of learning and input.
If you could have one billboard anywhere with anything on it, what would it say?
I wish I could remove all billboards in the world, and ensure they were never replaced. But I know that that wasn’t really what you’re asking, so my better answer is : I think I would make a billboard that would say, “IT WON’T MAKE YOU HAPPY”, and I would place it outside any big shopping mall or car dealer
What advice would you give your 30 year old self?
At 30, well let’s see, I had just started CD Baby, that I think the biggest advice I would give to my younger self is that women like sex.
I think the more interesting answer is that my advise to my 30-year-old self would be don’t be a donkey.
It’s a fable about a donkey that is standing halfway in between the pile of hay and a bucket of water. And he just keeps looking left to the hay or right to the water, trying to decide hay or water, hay or water, he’s unable to decide. So he eventually falls over and dies of both hunger and thirst.
So the point is that a donkey can’t think of the future. If he did he’d clearly realize that she could just go first drink the water and then go eat the hay.
So my advice to my 30 year old self is don’t be a donkey.
“You can do everything you want to do, you just need foresight and patience. “— Derek Sivers