Tools of Titans: Derek Sivers Distilled (#202)


“If [more] information was the answer, then we’d all be billionaires with perfect abs.”

– Derek Sivers

Derek Sivers(@sivers) is one of my favorite humans, and I call him often for advice. Think of him as a philosopher-king programmer, master teacher, and merry prankster. Originally a professional musician and circus clown (he did the latter to counterbalance being introverted), Derek created CD Baby in 1998. It became the largest seller of independent music online, with $100 million in sales for 150,000 musicians.

In 2008, Derek sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education. He is a frequent speaker at the TED Conference, with more than five million views of his talks. In addition to publishing 33 books via his company Wood Egg, he is the author of Anything You Want: 40 Lessons for a New Kind of Entrepreneur, a collection of short life lessons that I’ve read at least a dozen times. I still have an early draft with highlights and notes.

I posted the following on Facebook while writing this chapter: “I might need to do a second volume of my next book [Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers] 100% dedicated to the knowledge bombs of Derek Sivers. So much good stuff. Hard to cut.”

Here’s a bit of what made it into the first edition — cherry-picked from the nuggets I’ve applied to my own life. Enjoy!

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#202: Tools of Titans: Derek Sivers Distilled

Want to hear an entire conversation with Derek Sivers? — Listen to this podcast, which was Derek’s first appearance on the show, and also a favorite of Seth Godin. In this episode, Derek discusses developing confidence, finding happiness, and saying “no” to millions (stream below or right-click here to download):

Tools of Titans: Derek Sivers Distilled (#202)

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QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

Selected Links from the Episode

  • Connect with Derek Sivers:

Twitter | Website | Facebook

Show Notes

  • Derek has read, reviewed, and rank-ordered more than 200 books. Which are among the most important? [05:04]
  • Kevin Olega tells us how an episode with Derek changed his life. [06:06]
  • It’s not what you know — it’s what you do consistently. [06:49]
  • The best plan is the one that lets you change your plans. [07:43]
  • Who does Derek think of first when he hears the word “successful” — and why is the third person who comes to mind probably more successful? [08:33]
  • Just starting out? Say “yes” to everything — even if it’s playing acoustic guitar at a pig show in Vermont. [10:44]
  • The standard pace is for chumps. [12:40]
  • Advice Derek would give to his 30-year-old self. [15:35]
  • Business models can be simple: you don’t need to constantly pivot. [17:19]
  • Once you have some success: if it’s not a “hell, yes!” it’s a “no.” [19:24]
  • Lack of time is lack of priorities. [21:22]
  • What would Derek put on his billboard? [22:23]
  • On taking 45 minutes instead of 43. [23:10]
  • Why Derek has no morning routines. [28:48]
  • Treat life as a series of experiments. [30:55]
  • The most successful email Derek ever wrote. [31:57]

People Mentioned

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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23 Replies to “Tools of Titans: Derek Sivers Distilled (#202)”

  1. Awesome! I loved the last Derek Sivers episode. I’ve got my copy pre-ordered and am looking forward to everything!

  2. Sivers’s deal to sell CD Baby is frequently described incorrectly, including here. He gave his shares to a charitable remainder trust, which then sold the company for $22 million. Sivers receives $1.1 million (pre-tax) from this trust each year until his death, then the remainder goes to charity. Sivers describes this transaction himself in some detail, and it’s not that wild or unusual. Yes, he’s a charitable dude (fair enough) just don’t imply he gave the company away. Not even close.

  3. Derek Sivers, the master distiller, distilled. That was great Tim. Tasty. Sweet. Short. Great cherry picking. I love all kinds of distillations but this one (along with my neighbour’s hand crafted gin) is in my top 5 at the moment. Derek and you have a similar vibe: humble, street smart, crazy, honest and unpretentious. I’m not surprised you get along. This world needs more distillers.

  4. Looking forward to hearing this! Tim – forgive the unrelated question, but can you share with us the supplier or where you got your Living Wall?

    It’s awesome, and I want one! (I’m sure there are others that like it too). I’m pretty sure you haven’t covered this anywhere else on the blog or the podcasts. Thanks in advance!

  5. Love it Tim. I listened to the Derek Sivers episode three or four times. It’s great to have all the nuggets in one place! I will be returning to it many many times. Thank you both.

    PS – was that you doing the voice over?….

  6. Hi Tim, I really enjoy listening to your podcast! Keep up the good work. Especially love the quote about billionaires with perfect abs!

    PS: Probably you have thought of this before.. I am from Europe so every time you link to a product on I copy the book title and search it on… If you would link to the country specific Amazon page of the respective reader and if you would sign up on the country specific Amazon Affiliate programs you could easily increase your Affiliate earnings quite significantly..

  7. This episode was a blast. Just awesome. Brilliance distilled. I love your podcasts. Keep up the good job. Thumbs up. Your fan from the Czech Republic. Jirka B.

  8. This was great – so many gems that I’m psyched to use! But my favourite? If it’s not a ‘Hell yeah!’, it’s a ‘no’ so I have energy/time to rock the things I really want to do. Thanks.

  9. Tim and Derek, I lived mostly of my life in London and so would hear Land of Hope and Glory once per year…usually…in a family ritual of watching Last Night of the Proms. Now, I get to hear its marching crescendo alongside the highest planes of Sivers’ wisdom! (…And not that a pavlovian response is needed for me to listen to this again and again…). Per Maija, I love the distillation and thank you.

  10. Hey, Derek! You look great by the way… clearly whatever you’re doing is working… you look about 15 years younger! 😉

  11. This is a great format that focuses on reviewing the key nuggets of wisdom from your guests. Keep up the great work.

    Tim, you mentioned Charlie Munger in passing in this episode. I am a big fan of his work on mental frameworks. Have you thought about doing an episode with him? He seems to be a natural fit with your philosophy.

  12. Derek is one of Tim’s guest I admired the most. He has a good philosophy of life, living simply, doing what he loves. On his first Podcast with Tim, he says he answers every email he receives. I wrote to him and I got his answer the same day. A man of his word.

  13. ======== Ring Ball at Nasdq ========

    It’s been a dream of mine for 15 yrs. I’m love the opportunity to experience it.

    Much more success,

    Melanie M

  14. Sivers is so goddamn interesting to listen to. The man has a very peculiar way of expressing himself, and has lots of great life lessons that I find myself very receptive to.

  15. Hi Tim!!!!!!!!!!

    1- LOVE TOT!


  16. Episode 370.5 dropped into my Podcast downloads. I liked Sivers at first but as the show went on, he came across as disconnected from the current world. Another white male millionaire who made is money years ago and is now trying to figure out what to do with his time.