The Accidental Millionaire
The Most Interesting Man on the Internet? Getting to Know Derek Sivers
If you have any interest in marketing, business, or creativity I recommend checking out Derek Sivers and his books. Derek is a professional musician and started CD Baby back in the stone ages of the internet. It initially was a side hobby to give his independent musician friends an outlet to sell their music. He eventually started to charge for the services and the business later netted him $20,000,000 when he sold it.
Late last year I had the privilege to purchase all his books directly from Derek. He designed the entire process himself. He built the online store and self-publishes his books. He narrated the audiobooks, and they sound great too. Derek’s background in music, technology, and writing is a unique talent stack.
Derek is an incredibly nice guy too. He makes a strong effort to answer emails and connect with everyone. I really appreciated it when he responded to my emails.
Anything You Want is Derek’s story of starting and running CD Baby and the lessons he learned. In short chapters Derek tells his entrepreneurial story and all the mistakes and gory details that go along with it. Of Derek’s four books, this one is my favorite.
Some highlights include:
How Derek became an accidental entrepreneur. He started CD Baby as a hobby, and it slowly grew into a company with employees.
How Derek learned to delegate by having his employees create internal documentation so they could consult it instead of running to Derek for every question.
How Derek refused outside funding and consultants and instead obsessed with pleasing customers.
How Derek got into an accidental tiff with Steve Jobs.
How Derek hired a guy to digitize all the CDs who later goofed off on the job for months before being found out. It caused lots of headaches for Derek who had to work overtime to get things caught up.
How Derek abdicated all major HR and employee benefit decisions to his employees. When Derek had to pump the breaks to avoid financial ruin it caused his employees to turn on him and alienate him completely. He never returned to his office again before selling CD Baby.
How Derek made a legal mistake by using his dad’s company for CD Baby’s bank account. (In Derek’s defense, an incompetent banker suggested it. It wasn’t Derek's idea.) Doing that unintentionally gave his dad most of the ownership. It cost Derek a ton of money later to sort it out.
How Derek sold CD Baby for $20 million. He put the funds into a trust that pays him 5% a year. When he dies, the funds are donated to benefit musical education. I think that’s a brilliant estate plan! That protects his assets during his life, gives him plenty of income to pursue his own interests, and ensures most of it will go to charitable causes.
Your Music and People are the lessons Derek drew from his experience as a musician and on his way to starting CD Baby.
In short, you must learn how to market yourself. If you do it well, you are doing the world a favor.
Some highlights
How Derek connected with a record producer who was a guest lecturer at a college class and complained he missed lunch. Derek snuck out of the room and had pizzas delivered. The producer was impressed and later helped Derek’s music career.
How rock stars would lament to Derek how the record labels controlled them and bossed them around.
A band found it’s best marketing tool when a drunk audience member said they’re like “hillbilly flamenco”. Before they struggled to get into festivals and when they pitched themselves with that phrase they had an easier time getting in.
Hell Yeah or No is a collection of heuristics and life lessons that Derek has learned.
Some highlights:
If someone asks you to do something and your reaction isn’t “hell yes”, you should consider saying no and politely declining.
What’s obvious to you is amazing to others. Don’t be afraid to share what you think is “obvious”. It may be mind-blowing to other people out there who don’t share the same insights as you.
Life has no speed limit. Derek was able to graduate college in two and half years because he learned how to go faster from a mentor. The mentor taught him how he could teach himself at an accelerated pace and test out of entire semesters of classes.
Assume you’re below average. Everyone thinks they’re above average at driving and most other things. That is statistically impossible. Instead, assume you’re below average and see what you can learn. It will take you farther.
Relax for the same result. Derek tells a story of how he would take aggressive bike rides going 100% effort. He felt exhausted and sore afterwards every time. One day he decided to go slower and enjoy the ride. To his astonishment, it turned out the slower ride was only a few minutes longer and a lot more enjoyable.
How to Live is Derek’s latest book as of November 2023. It’s a collection of 27 different philosophies of life. Being the fastest or the richest or the most travelled or the most connected or the most family-oriented and so on. It ends with a short conclusion that ties it all together. I won’t say what it is😉.
This is Derek’s shortest book and it felt like the longest to read. Derek’s writing is usually more about his individual experiences and the valuable lessons he learned. How to Live is much more philosophical and abstract in contrast.
Check out Derek
All the books are short and punchy. You might not agree with everything, but he has a unique take on a lot of topics.
His personal website and blog are at sive.rs. I recommend checking it out.
If you don’t want to get these books right now, some of the content from his earlier books can be found for free on his blog sive.rs/blog.
All the profits from his books go to charity as explained here sive.rs/575k.
He has a “now” page where he frequently updates where he’s at and what he’s working at sive.rs/now.
As I mentioned earlier, Derek is easy to contact and makes every effort to respond. See sive.rs/contact.
As of late 2023 he’s actively working on his fifth book “Useful Not True”. A sneak peek is this post at sive.rs/pnt. It’s one of Derek’s most powerful pieces and makes me excited for its publication.