Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions (#125)

The tim Ferriss Show with Derek Sivers

“To me, ‘busy’ implies that the person is out of control of their life.” – 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, 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 5 million views of his talks. Since 2011, he has published 34 books, including “Anything You Want,” which I’ve personally read 10+ times.


You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions (#125)

Want to hear another podcast from a tech entrepreneur who built and sold a multi-million dollar company? — Listen to my conversation with Bryan Johnson. In this episode, we discuss his path to building a business worth $800 million (stream below or right-click here  to download):

#81: The Rags to Riches Philosopher: Bryan Johnson's Path to $800 Million

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QUESTION(S) OF THE DAY: In this episode, Derek discusses how he deconstructs the ideas from books into useful “do this” style directives. If you were to write a directive based on lessons from this podcast, what would it be?  Please let me know in the comments.

Scroll below for links and show notes…


Selected Links from the Episode

Show Notes

  • Derek Sivers, the leader of the circus [8:56]
  • A framework for developing confidence [15:41]
  • How Derek Sivers graduated from the Berklee School of Music in two years [19:26]
  • Lessons learned from the Santa Monica bike path [28:31]
  • How CD Baby came to be [34:51]
  • The co-op business model [38:36]
  • How one e-mail helped make CD Baby a remarkable company [41:36]
  • How Derek Sivers responded to those seeking to invest in CD Baby during the dot-com bubble [46:01]
  • On his relationship with money and saying “no” to millions [49:06]
  • The origins of the HELL YEAH! Or No. [57:06]
  • Discussing the Now Now Now project [1:01:21]
  • What inspired the automation of CD Baby [1:03:41]
  • Derek Sivers’s book consumption habits and creating directives [1:12:36]
  • Most gifted books [1:46:36]
  • What purchase of $100 or less has most positively affected your life? [1:49:16]
  • What Derek Sivers listens to when working out [1:51:11]
  • If you could have one billboard anywhere, what would it say and why? [1:52:46]
  • Advice for your thirty-year-old self [1:54:36]

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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138 Replies to “Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions (#125)”

  1. Love these interviews. My favorites are the “practical spirituality” themed programs (and the entheogens, and Jamie Foxx!) but I’m impressed by the breadth of subjects covered. My nomination for your next interview: Esther Gokhale, founder of the Gokhale Method. There’s a 6-minute Ted Talk that covers the basic concept. There’s also a decent article on NPR’s website (although it goes way off the rails at the end, in my opinion). here’s a quote: “She’s helped YouTube CEO Susan Wojcicki and Matt Drudge of the Drudge Report. She has given classes at Google, Facebook and companies across the country. In Silicon Valley, she’s known as the ‘posture guru.’”

    I’m brand new to the method, I’ve only taken a free workshop offered by an amazing teacher named Natasha here in San Francisco, but it’s affected me in a radical way. Amazing how a simple shift in posture can have such wide-ranging effects – emotional, psychological, physical. Gokhale would be an interesting interview for her anthropological studies alone.

    Thanks for the inspiration, Tim!

      1. Outstanding conversation – I can’t wait to comb through Derek’s site! Definitely try to get him back on. I’d also like to hear the full list of directives.

      2. oh man.. me too!

        I came to the show notes in hopes that they might be here…

        I think the list would make a great in-between-isode or whatever you call them.

    1. Would also love to hear rest of that list.

      What he shared was very thought provoking and well thought out.

  2. In terms of directives to live your life by

    I kinda like the one by Sam Berg a fictional character in Terry Pratchett’s book Long Utopia

    * Apprehend

    * Be humble in the face of the universe

    * Do good


  3. What a great interview! I was entertained throughout and walked away feeling very happy..and motivated. Thanks Tim and Derek

    Tim, do you still drink wine while fasting? I’m guessing no, but had to ask the question.

  4. BIG Hell Yeah.I want to hear more from Derek. It was the most precise information,one can get from any person. specifically those Directories. Please make it round Two. Will Look Forward to listen it.

    Thank you so much Tim….you are awesome….i wonder where & how would have learned this amazing Lessons.

    Thank You so much 🙂

  5. BIG Hell Yeah. I want to hear more from Derek.”It will make me happy”. It was the most precise information,one can get from any person. specifically those Directories statements.

    Thank You so much are super awesome. i just wonder sometimes where & how, i would have learnt these lessons…its very helpful.

    Thank You so much :-)!

  6. Great interview, as usual, Tim. Derek Siver is a great man and big inspiration, so thank you for this interview 😉

  7. Another totally lovable interview! This long format is so great and allows for so much depth and breadth!! I’m intrigued that several of the interviews (this one and also Alain de Botton) have gotten in to this concept of “expect the worst” or “plan for the worst.” It just so flies in the face of the overly popular and largely misunderstood Law of Attraction. And you’ve obviously you’ve all used “positive pessimism” to good end.

    I hope you do a follow up with Derek and would also love to hear more directives.

    I *do* think the timing of books is important, but I also believe a really great book will resonate on a larger level with most people whenever they pick it up. Derek is the first person I’ve ever heard say The Magic of Thinking Big didn’t hit a strong chord. And I agree, I didn’t care much for The Happiness Project; Gretchen Rubin’s perfectionism bled through too much for my taste.

    I find value in the idea of distilling things down, but I still appreciate reading the 200-300 page book (maybe not the 600 page one, depending). I think that the way an author lays out his/her thoughts and supports conclusions often helps you understand the point at a deeper level. A thin little book, a short version as a quick reminder or summary, yes; but I want to hear the details of how someone got to their beliefs. For me it’s not so much defending a position as giving it life; otherwise it can feel like skimming the surface and directives can become platitudes.

    I sound like I’m taking issue with some of what Derek said, but really I loved the interview and so much of what he talked about– and that it got me thinking about these things!

  8. Great episode! I’m glad William Irvine’s book on Stoic joy was discussed, this book was an inspiration for a book I am currently working on. I love Derek’s notes on the book (or maybe I should say I had a ‘preferred indifferent’ reaction, lol) very insightful. Can you get Professor Irvine on the show, Tim?

  9. Derek Sivers’s book consumption habits and creating directives [1:12:36]

    Based on reviews

    Personal recommendations

    What seems to be popular

    Chapter skimming and chapter jumping

    Book consumption based on what people deem important and not what seems to be popular. What is “Popular” has been manipulated by big biz.

    If you have two options Popular and Latest, try Latest too.

    We need a – like of all recent Kindle highlights to enable book discovery (hint: funding) in Amazon.

  10. Definitely one of my all time favorites. So many awesome quotes in this episode. “The standard pace is for chumps” and “They overestimate what they can achieve in a day or a week… but underestimate what they can achieve in a year or even two years”

  11. Great podcast. As an addition to your conversation about saying ‘no’ to millions, During my interview with Derek Sivers last year (LESSON 59 of How to Shape Human Behavior –, his response to my question as to as to why more entrepreneurs don’t follow his charitable trust investmant path, he said that:

    “From the feedback I’ve received from people in the past 5 years since I announced that I did this, it seems most people want the big money. They want $22M. They want the ability to buy a $20M home and a $2M jet or perhaps buy another business for $20M. Many would rather leave that entire amount to their kids.

    Most business people have told me I’m crazy for doing this. So I think the whole ‘give it away and live on the interest’ is just not a popular idea with people.”

  12. Just listening to your great Derek Sivers interview – regarding the ‘geek in America’ book were you thinking of Travels in Hyperreality by Umberto Eco?

    I re-read it recently – it’s old – translated into English in 1986- but it’s fascinating and pretty interesting to compare then and now

    1. I paused the episode to comb the comments and try to find someone who had identified this book – would love to know whether that’s the one!

  13. Great interview. I like Derek’s thinking. He really gets at the core philosophies and the “why” he does things.

  14. Questions of the day answer: Ask better questions.

    That is my genuine answer, not the most meta backhand ever. 🙂

  15. Great podcast. We do need some sound clips of Derek Sivers first lesson to 30 year olds about knowing women like sex haha. That would be a meme in itself and I would love to hear all his lessons of actual things to do.

  16. Great episode! Thank you for making these. I also wanted to ask if you’d consider interviewing the pianist Marc-André Hamelin? He’s as close as it gets to a force of nature, especially with those recordings of Godowsky’s music.

  17. This was a really interesting interview. Quick comments:

    – Derek is a great storyteller.

    – Love the idea of saying “no” to everything that isn’t awesome, but I guess you’d have to accept (or not care) that when practicing this rule, a lot of people may label you uncaring / a dick / lazy etc (?)

    – Would love to hear how Derek was introduced to programming, and how he managed to hone his skills in that area while doing all the music / circus stuff.

  18. Excellent! Derek is a very practical guy. Bring him in more often!!!

    As an INTJ, I feel totally reflected by both you and Derek, Tim.

  19. This is by far my favorite interview!!!!!!!

    Conformity vs Rebellion!

    Loved the context of “It won’t make you happy!”

    I would listen to 100 more interviews of his!

  20. I love this episode. Derek sounds like such a cool guy with an amazing outlook on life. You definitely need to have him back.

  21. Another great interview (we’re all really impressed, Tim). What an awesome guy. Such clarity in thinking and confidence in his ability to see what’s right for him. Speaking of confidence, I can’t help but notice Tim bringing this up so often in interviews as if he himself is interested in something he appears to have in abundance. Am I missing something?

    Love the co-op business idea – which Tim also seems to prescribe, that you can just scratch your own itch when starting a business. I’m seeing this duality more and more of trying to create demand on the one side and simply doing what the market asks of you up front. Also loved the 18 bits of advice towards the end.

    Good stuff.

  22. Related to note-taking, (for me) the easiest way to do that is to get a Kindle book, underline as you read, then login to, select all notes from a particular book and copy them to a text file (or whatever). Although I see a great benefit in rewriting too – it’s a kind of recapitulation.

  23. I also think that, for many, figuring out what to do for themselves is part of the journey. Not all directives, “do this,” or just “do that,” will work for everyone — like a recipe. I think people need to search their own inner experience, so they can internalize and learn for themselves ,while taking responsibility for their decisions.

  24. I’m really enjoying these podcasts as a new fan. Is there a strategic reason why you don’t post transcripts? I’d set something public up myself but wouldn’t want to violate copyright

  25. Timothy, I have been an avid listener of yours for about 2 years now and always look forward to the content you provide. This episode did not disappoint. I appreciate all the work you do to bring these excellent knowledge-nuggets into the world.

    -Raving Fan

  26. Awesome interview! It would be cool to hear you elaborate and dig into Introverts and INTJ personality on a future podcast 🙂

    An interesting challenge would be to make an episode en Espanol mi amigo, maybe just a Q&A just to keep it short and not to offend any non Spanish speakers…

    Thanks for inviting awesome human beings on your podcast!

  27. Excellent post, it is so truth to follow you “feelings” , when Derek says that if you -really- are not excited about any task better do not do it. Also about to be persistent but for put a limit if you find your project stuck and persist with your searching, also the human touch in business , well great and new things to learn

  28. I really enjoyed the episode. I had some fun and wrote teaser bullets for my top 10 takeaways (in chronological order):

    * A 4-word sentence that dissolves stage fright.

    * “The standard pace is for chumps” – why, if you don’t set your own pace, you could waste years of your life.

    * The specific steps Derek took that allowed him to graduate from Berkley College of Music in 2 years instead of 4. These tricks work for most subjects at most colleges.

    * “Relaxing for the same result” – how Derek went from being stressed and miserable, to enjoying himself… with only a 4.5% drop off in results. An essential lesson for any type A personality.

    * One question to ask yourself that’ll help you create the best product or service in your industry.

    * Instant pay raise – when you can charge 40% higher prices without creating price resistance.

    * Stick or twist? Derek’s 4-word credo that tells him when to grab an offer, and when to wait for something better.

    * The secret to effective delegation. Do this and you’ll never have to micro-manage.

    * Rich and happy? Just follow these 9 easy rules and you, too, can be broke and miserable.

    * What’s the cause of most misery in our lives? And how to fix it.

  29. I haven’t finished listening to this and I’m feeling super inspired this Tim. In particular his “Hell Yeah! or no idea”, I totally agree. What you’re doing right now is awesome because when I started reading your stuff I had time to read. Now with my own business, two kids and a lovely wife my life is so full that audio is the way I get 80% of my inspiration. So dude, I’m sure at some point we’ll meet but right now its seriously cool being able to listen to this kind of discussion and get everything I need. Cheers Bro.

  30. I haven’t even finished the podcast yet and had to comment because it is another all-time favorite. Thank you, Tim! This was like a Christmas present to your audience. Derek Sivers would have never come to my attention without this podcast, even though he is obviously well known in the business world. I found the interview just so completely enjoyable, entertaining, inspiring. I can’t wait to buy and read his book. Thank you again, Tim…so grateful for how you enlarge and enrich my world!!!

  31. Great episode, Tim. Love the quote that inspired Sivers: “The standard pace is for chumps.” (Kimo Williams) And yes… make the T-shirt.

  32. Thanks Tim for another awesome episode. Please do package “Derek’s Directives” (in Full) as a separate short episode.

  33. Hey Tim, Firsly just wanted to say thanks. You have inspired and motivated me and giving me the proverbial “kick up the ass” that I needed, this year. Your work has changed the way I look at things and especially how I approach obstacles, amazing books, great podcasts and recommendations. Keep doing your thing!

    Secondly thought I would “pay it forward” and recommend a few things, I thought may interest you.

    Old School hip hop albums –

    1) Pete Rock and CL Smooth – Mecca and the Soul Brother 1992

    Stand out track – They reminisce over you (T.R.O.Y)

    2) Big Daddy Kane – It’s a Big Daddy Kane 1989 (interesting fact – B.D.K was the one who gave Jay-Z his break)

    Stand out tracks – Smooth Operator and Warm it up Kane

    3) Nas – Illmatic 1994

    Stand out track – N.Y State of Mind (but the whole album is great, actually his whole catalog is great!)

    Old school hip hop tracks –

    1) Brand Nubian – Slow Down and Don’t let it go to your head (you may had heard the second one in HBO’s entourage)

    Old school hip hop movies –

    1) The Wood 1999

    2) Do the right thing 1989

    TV Series and Movies –

    1) This is England movie (Relativly unknown outside the U.K, this is English cinema at it’s best. A movie followed by 3 mini series that follow the same group of friends over a number of years

    2) This is England 86

    3) This is England 88

    4) This is England 90

    5) Skins series 1,2,3,4 (The original U.K version was created by young, unestablished writers and was the spring board for a number of young British actors like Dev Patel, Jack O’Connell and Kaya Scodelario as well as resurrecting the career of Nicholas Hoult)

    6) Peep Show (British TV series , comedy)

    7) The inbetweeners (British comedy 2 movies and and 3 TV series)

    8) Toast of London (British TV series, comedy)

    9) The Hunt (Great Danish film)

    Random –

    Rooibos Tea – South African Herbal Tea that is naturally caffeine free.

    Biltong – Dried meat, South African style. Basically like jerky but so much tastier (and great for your Slow Carb Diet.)

    Droewors – Dried South African sausage (as above)

    Ouma Rusks – like biscotti with a South African twist and perfect with hot Rooibos tea

    Lastly have you ever considered approaching Grant Morrison, the comic book writer for your pod cast. I think he would be a great guest not only in regard to his career but also with his ideas on magic and sigil working. Another really interesting possibility would be Wade Davis, the ethnobotanist, anthropologist, writer and inspiration for 1996 Wes Craven movie “The serpent and the rainbow”. Both great men with a lot to say.

  34. Amazing show Tim and Derek. I have been listening for a long time but the first time I have come on to write (Sorry about that!) Found this episode extremely valuable, great follow up materials and awesome list of books and notes to dig into! Thank you! Please do post the rest of your list Derek, I took notes, pausing and playing the podcast to get them all down. Amazing applicable lessons. THanks gents! Keep it up Tim, you are a rockstar.

  35. This one is easily one of my favorite podcasts of yours. Everyone should listen to this- everyone with a curious and open mind. So much quality content in a short time. Please do have a round 2 or even 3 with Derek Sivers.

    Here are some ideas from this podcast:

    -“You are whatever you pretend to be.” -Kurt Vonnegut.

    You can choose to be confident. And sometimes a person (a woman you value or a coach) can help you reveal your potential.

    I know another great quote about this: “If you treat an individual as he is,he will stay as he is, but if you treat him as he were what he ought to be and could be, he will become what he ought to be and could be.” -Goethe

    -Don’t say yes to things that don’t excite you.

    – From 1:10 to 1:20 I was laughing my butt off.

    Ferriss: Read the f’in book before you ask questions! 🙂 (4HB)

    -All the great directives as to what to do with your life and how to be useful to others. The ones I find closest to my ideas are : 1.have no loyalty to place and corporations, 2. don’t make plans. can help others by becoming rich.

    – Always remember that things can always get worse. Appreciate every minute and the beauty that surrounds you.

    -If there are many things you want to achieve in life but don’t know which route to take, think long term. Do one thing at a time.

    -When you give advice to people, talk about the ideas, not yourself. (This is exactly why I’m very picky about who I hang out with in my daily life, who I listen to online or on tv. I rather sit and stare at a blank wall than listen to someone’s boring life story. American women especially talk a lot about themselves.)

    -Each place/country has its own cultural norm in approach to life, time, convention, rebellion etc. They should be explored. (This kind of thinking is on the brink of extinction.)

    I can relate to so many ideas in this podcast. Sivers is definitely my kind of person. It has been very uplifting for me to listen to this conversation. Thank you very much Tim and Derek! Looking forward to the second one.

    All the best xx

  36. Is Derek coming here to respond every question as well?

    If he does, Derek, you are amazing!! This is one of the best podcast for me, and I listened to all of them. (Along with Josh Waitzkin).

    Amazing interview, keep up the good work!

  37. Does anyone knows where I can find the complete “to do list” Derek spoke of? The full 3 minutes, or it written somewhere..

    Thanks in advance

      1. Thats awesome Kiraz, but he speaks of a few he has no time to go about on the podcast..

        Even the 30 min keynote lecture. Does anyone has it?

  38. Having listened to Stan McChrystal ‘s podcast whilst on holiday a few weeks back I thought I should download a few podcasts to listen to in the car on my 20 min commute. This was my 1st going to work took 1 and a half hours due to traffic accident snarling up road network coming home took 3 hours. Last time I do this if this is the effect your podcasts have on the universe. Seriously I thought this and the others I had were excellent and a valuable use of my time

  39. Hey Tim – I enjoyed this – listening to two ‘active’ readers. However something just occurred to me – I’ve listened to probably 10-15 of your podcasts but they’ve all been men. What’s up with that? When you mention women it’s only i the context of dating. Why? (one podcast with someone you explain as the wife of someone else doesn’t really count). Bottom line – I guess I’m asking/challenging you to look beyond the dudes to inspiring, interesting women. thanks!

  40. This interview was amazing, Tim. Thank you! Enjoyed Derek’s talk at WDS2015 and he’s a fellow Portlander–what’s not to love? Keep these gems coming.

  41. Looking forward to this one, Tim. Here’s a Victor Frankl quote from the book Man’s Search for Meaning that I think your readers will like…

    “We who lived in concentration camps can remember the men who walked through the huts comforting others, giving away their last piece of bread. They may have been few in number, but they offer sufficient proof that everything can be taken from a man but one thing: the last of human freedoms—to choose one’s own attitude in any given set of circumstances—to choose one’s own way.”

    Love the podcasts, keep it up!

  42. Thanks Derek for being on the podcast. Learned a massive amount from you, and looking forward to a second episode if you feel it would be a hell yeah choice for you. Huge fan of your website and /books page.

  43. Tim, squeezing you’re work space into the ‘fire escape’ is a building code violation… sorry… couldn’t help myself… Great Interview By The Way!

  44. Derek,

    You have beautiful spirit.

    I’ve done the same bike path in Santa Monica down to Marina Del Ray and Manhattan Beach.

    Don’t worry, I’ve had penguins fly over me as well 🙂

  45. Great podcast, Tim. Regarding Derek’s search for books that best describe a countries people, character and culture, the one for Mexico is “The labyrinth of Solitude” by mexican poet Octavio Paz. This book won him THE NOBEL LITERATURE PRICE. It’s an in depth, beautifully written essay and critique on Mexico’s quest for identity and it fills you in on all of the historic events that have made the country, and the people, in all its complexity and plurality, what they are today. It was written in 1950 and still remains as current as if it was written yesterday. It’s very rich in culture, symbolism, history, philosophy, and yet still very deep-felt and poetically written. I’m currently rereading it to highlight the phrases I consider the most beautiful. If you can read it in spanish, it’s original version, it’ll be worth the challenge! Merry Xmas, man! Love your stuff!

  46. Here’s a useless coincidence: Tim mentions the Five Minute Journal (I use it, love it) – and THEY use basically the exact copy of Derek’s CD Baby shipment notification email.

  47. I am huge fan of both Derek & Tim. This is definitely the most valuable interview Tim has done for me.

    I just feel clear. Like I’m out walking after the first snow. My mind is quiet.

    Read the Book! This shirt exists. That phrase is particularly legendary in the culture of a band I love that everybody else hates. Check the link i included.

    The standard pace is for chumps!

    You are the person you pretend that you are!

    Hell yes or no.

  48. Hey guys I wrote down “Derek Sivers – Directives for Living” from this podcast in a blog post. I’m personally a more visual person, so I hope it helps others to see them written out.

    I’d post the link but want to be respectful of the commenting rule. Hopefully someone from Tim’s camp gives me to green light to share the link.

  49. Hey guys I wrote down “Derek Sivers – Directives for Living” from this podcast in a blog post. I’m personally a more visual person, so I hope it helps others to see them written out.

    I’d post the link but want to be respectful of the commenting rule. Hopefully someone from Tim’s camp gives me to green light to share the link.

    1. Thank you for sharing this link, Ben! I was hoping I would find the directives writen somewhere amongst the coments !

      Amazing Podcast… I am never disappointed. I listened to it a month ago in my car… And felt the need to revise Derek’s directives today.

  50. Great interview Tim. Would love to hear more on the directives. In addition, it would be great if you discussed with Derek and other guests you have that are raising children their thoughts on the matter.

    Is it enough to just be a good role model?

    What are key messages you want to get across to your kids?

    How do you know you are succeeding?

  51. Thanks Tim and Derek, especially on your opening up of the simple rules of thumb, heuristics, that keep your life and focus and values in just the right place. Fascinating to hear for example that you hardly spend any time with documentaries, film or blogs, in the focus on reading and writing. This opened a vein of thinking and self-questioning that will influence…

  52. Yo Tim – your podcasts are getting better every time – way to go dude. Q: tried to access Derek Sivers transcript – it took me to a leadpages page – I entered my email – got a link – downloaded – but they’re older transcripts of podcasts. If this is the system, how can I know when the transcript for Sivers is ready and how do I get it now? Happy, healthy New Year man!

  53. According my opinion this is one of the best podcasts until today! (among with the one with Naval Ravikant – I realize that you also promote the one with Jamie Foxx as one of your best podcasts of this year but apart from the “What’s on the other side of fear?” quote i really don’t feel very connected to this one, maybe i have to listen again…)

    What touch me most was the idea that from time to time you have to stop and try to digest the knowledge you receive from books, podcasts etc. otherwise you loose the real power and value of this knowledge.

    1. Hi Stoles,

      I tend to think the reason you connected to Derek’s (as I agree it was freaking great) is that he seems like a super grounded and approachable person. Jamie Foxx was/is a rockstar and I think it came off like that in his interview. I mean how could it not, the dude was partying with P Diddy/Puffy/Puff Daddy/etc.. before he was even famous. It seems like Jamie might be someone you’d struggle to meet, but that could just be the fear we tend to have of famous people and the whole putting them up on a pedestal. I personally think Jamie would be as grounded and down to earth if you ever got the chance to meet him.

      I think both interviews were fantastic, but just for different reason.

      Thanks for all you do Tim, I finally got your book (4hww) and devoured it in 2 days. Luckily for me I have already be working on some of the automation/liberation steps and am currently working from home 2 days a week. My next step is to find my ‘muse’ and start generating some income so that I can free even more time. Your book came at the perfect time and is the extra motivation I needed. Thanks!

      1. First of all, I agree that every Tim’s interview is a real goldmine of ideas and even if you don’t feel “connected” with the interviewee every time there are great ideas to think about.

        i also agree that maybe Jamie Foxx if far away from my “comfort zone” and that’s why i don’t feel this connection on first hand.

        To be honest i feel him far away from my “personal culture” and maybe that’s why i’m not that excited. In any case i will listen again this interview and i’m sure that there are great ideas to think about.

  54. This is one of the best episodes I’ve heard so far. Derek is a world class storyteller. Favorite quote came from the Kimo Williams story. It was something like “The standard pace is for chumps.”

  55. Super uplifting and so worthy of what we would call the modern stoic. I’ve learned so much from this episode. Thanks again Tim + Derek.

  56. I love this podcast but I have to wonder about Siver’s Santa Monica bike story. Maybe I misunderstood, but I believe he said he completed a 25 mile bike course in 43 minutes. If so, he could add cycling world record holder to his bio.

  57. Loved this one (as with so many of the ones you do). Derek is grounded, focused and authentic. I enjoyed the reminders to say yes only when it’s a “HELL yes” and to take notes on what I read. Keep up the fantastic work…it’s priceless to hear these interviews. I can take a lot of this and incorporate into my life today, which is what makes it so powerful.

  58. One great and elegant Wisdom from Derek @1h34min12 sek in:

    How to be useful to others:

    1. Get famous

    do everything in public and for the public , the more people you reach the more useful you are (the opposite is hiding which is no use to anyone) being famous

    2. Get Rich

    Money is neutral proof you are adding value to other peoples life: s. so by getting rich you are 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

    3. Share STRONG opinions

    Those who are undecided or ambivalent can just adopt your stance, but those who disagree can solidify their stance by arguing against yours. – THIS is very useful to others

    4. Be expensive

    placebo pill = twice as likely to have pain disappears when told that pill was expensive, people who paid more for tickets are more likely to attend the performance. So people who spend more for a product or service value it more and get more use of it. BE EXPENSIVE

    Thank you for a great podcast.

  59. It kind of irritates me to hear these guys talk about how being ‘busy’ is a lack of priorities. They are both single guys who are independently wealthy, so they have complete control over their time. If you have a job with set hours, kids who are involved in activities and a spouse who wants help around the house then your schedule is going to be a lot less flexible.

    Try telling your boss and family that you are no longer available much because you don’t want to be busy! You won’t have a job or much of family for long.

  60. Love the tidbits of wisdom from Derek. Thanks Tim for podcast. You mentioned how most of us hear only about successful startups and develop a survivorship bias and it instantly reminded me of this catalog of failed efforts – You’re probably already aware of this, but thought I’d share it here in the comments so other readers may also benefit.


  61. Love the tidbits of wisdom from Derek. Thanks Tim for podcast. You mentioned how most of us hear only about successful startups and develop a survivorship bias and it instantly reminded me of this catalog of failed efforts – You’re probably already aware of this, but thought I’d share it here in the comments so other readers may also benefit.


  62. So I wrote the list out. May not be word for word, but I got the majority of it correct. Enjoy!

    How to be useful to People

    Get famous. Do everything in public and for the public. The more people you reach the more useful are you are, the opposite is hiding. Which is of no use to anyone.

    Get rich. Money is neutral proof that you are adding value to people’s lives. So by getting rich you are being useful as a side-effect. So once rich, spend money to make others lives better you are even more useful to them. You are doubly 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 stance against yours. So even if you invent an opinion for the sole sake of arguing, boldly sharing a strong opinion is useful to others.

    Be expensive. People given a placebo pill were twice as likely to feel better when told the pill was expensive. People who spend more money, are likely to attend the performance. So people who spend more money on something value it more and get more use out of it. So be expensive.

    How to live in an unknowing world

    Prepare for the worst. Since you have no idea what the future may bring, be open to the best and worst. The best case scenario doesn’t need your worrying or attention. So mentally just prepare for the worst case instead. And like insurance don’t obsess on it. Prepare, and carry on with the good times.

    Prepare for disaster. If you ever watched a VH1 Behind the Music story, there is always a point where the narrator says and then things took a turn for the worst. So fully expect that disaster to come to you at any time. You must fully assume that it will 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 is the last time you maybe seeing them.

    Own as little as possible, depend on even less, the less you own. The less you are affected by disaster.

    Choose opportunity not loyalty. Have no loyalty to location, corporation or you last public statement. 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. Choose the plan that let’s you make the most plans. For example renting a house, is buying the option to move at anytime in an ever changing market.

    Avoid planning. For maximum options don’t plan at all, since you have no idea how your mood may change in the future, wait until the last moment to make the decision.

  63. What an Inspirational guy Derek is, been listening for about 6 – 8 months now, mostly during my daily commutes. So I haven’t taken notes, one of my “2016 Resolutions” is to take my own show notes…. HELL YEAH or no…. what a way to live. It’s incredible how much these podcasts have helped me better my life.

    Thanks for being unconventional Tim.

  64. This one stands out. The part about the directives (~1:31:22 and on) is nothing short of amazing. Seems simple, but that demeanor is rare these days. I had to replay it at 1/2 speed to take proper notes… really impactful and fun to listen to.

    btw, Derek is awesome too 😉

  65. The audio plugin kind of sucks, at least on Chrome. Just paused it and, when I returned, I had to start from the beginning and couldn’t skip the ads to get back to where I was previously. This has happened before, so I wanted to let you know. What’s wrong with SoundCloud?

  66. Fantastic Podcast, well done and thank you. I loved the idea of the “directives”, RTFM (Read The Frigging Manual” and how Derek has generated revenue by helping others and sharing.

  67. Hi Tim, Great interview! Do you know where we can get the complete “Do this” list.

    Thank you for creating this content, it’s really useful. Also, congrats on the quality of your guests.


  68. On the “No planning” directive, in which the idea is to, if anything, plan for the worst, but plan at the last moment, because while the day might be perfect out there in New Zealand, tomorrow that could all change, I have a few comments.

    First, I think there are a select few individuals who “take the blue pill” (or was it red) and see past all this nonsense (politics, standoffs in Oregon, etc) and realize that we might be like the Germans living in the Weimar republic, or the nobility so wonderfully portrayed in Miklós Bánffy’s book, They Were Counted (The Transylvanian Trilogy) (Writing on the Wall: The Transylvania Trilogy), soon to see their world drastically transformed. Certainly Bánffy had this ability, watching the frivolous politics of Austria-Hunngary with disappointment, with most of the attention on the balls, parties and horse races.

    (This is not a new idea, note the story referenced is one from the biblical times, the story of the writing on the wall. Tim has greatly reminded us of the ancient wisdom of the stoics, and so too in the bible. This particular story is rather interesting to those with puzzle-solving natures, as Daniel interprets the writing on the wall (MENE, MENE, TEKEL, PARSIN) first as nouns, then as verbs in order to decrypt their meaning.)

    Secondly, I wonder if there is a geographical aspect to this sense of possible impending calamity? This point was an important part of James Clavell’s Shogun, in which he theorized that the Japanese, due to living under extreme conditions, in a land that could be hit by typhoons, or earthquakes, suddenly wiping out everything, creates this “live the life to the fullest” philosophy. Perhaps Tim (and Sivers, since he seems familar with Japanese culture too) might have encountered this in their travels?

    Well, I highly recommend these books, they should be read and enjoyed in their entirety.

  69. Hi Tim, I have just listened to this podcast which I found incredibly beautiful and inspiring. I feel so close to what Derek says and I am happy having found him now. May I suggest you read a book by Theodore Zelding that I have just finished. The Hidden Pleasures of Life. It’s on Amazon. Really really mind blowing.

  70. I just told my 17 year old daughter that if she could listen to two podcasts that would set up her framework for life it would be this one and the Seth Godin interview from last week. WOW. Many times I was blown away in both of these however the biggest takeaway was when Derek talks about wanting to move to Kauai and get rid of the noise….did I ever relate. 8 years ago I did that. I left my business to run it ‘remote’…as a fellow INTJ I just couldn’t take the noise and distractions…I lost everything. I ended up moving back in ruin and building it back and wouldn’t take that lesson back. Thank you Tim for the continued excellent content and great humour….

  71. Hi Tim and Derek. During the podcast there was an “ask” for books on culture. Scrolling quickly through the show feedback, I did not see a response so here’s mine:

    1. The godfather of cultural insights is Hofstede. And the cultural tools link on this site can help you compare the cultural traits across countries:

    2. Beyond Culture by Hall is good book. Hall’s work also appears in SteelCase’s 360 magazine culture code issue.

    This is a fascinating article with many experts contributing to designing work environments that foster creativity and innovation based around local cultural preferences.

    3. Finally, selfish plug: You can follow me on twitter at @collabspaceguru, where I explore the impact of local cultural on collaboration technologies.

    Thank you,


  72. I love the way you guys think! I’m an INTP or INTJ (it’s close). I’m going to have to read more about stoicism. It sounds like it’s for me.

    Whoa, wait… What? Women like sex? That’s awesome news!

  73. Possibly my favorite of all your podcast episodes Tim! Astoundingly useful advice as I build my own business and venture through life. The amount of wisdom you’re able to extract from incredible human beings is remarkable… A million thanks for creating a program so damn insightful and useful!

  74. This is one if the best podcasts. I wish Tim would have let him read out more of his summarized lessons.

  75. FUUUUCCCCKKKKK!!! Sivers offered all of his bullet points directives on how to live, not published ANYWHERE and you cut him off, and asked him to just through two sections? WTF is the matter with you. Where’s the fire? why couldn’t you let him tell us? He wasn’t eager to leave. Why not let him finish. Who the fuck cares if your podcast is 2 hours or 3 hours? Ever heard of Dan Carlin?

  76. Loved this one..

    I have enjoyed every podcast I’ve listened to..over twenty I think now..

    Would love to hear you interview

    B J Fogg..


    Simon Sinek.

    Both preferably..their work has influenced my thinking also.



    I am glad you are here.


  77. Just listen to this podcast because I just read his part in Tool of Titans.

    So awesome, thank you!

    Seems to me that Tool of Titans was inspired by the idea of compiling Notes on books, but here from your podcasts instead. Which is even better, because I’m discovering so much great podcasts now.

  78. Thanks for taking the time, Tim and Derek. This was an amazing conversation; one filled with takeaways.

    Many of the ideas are concepts that I’ve been thinking about recently, but didn’t have the words to say. For example, I’ve been wrestling with the idea of conserving my time and saying no to more – ‘Hell Yeah or No’ hit this on the head.

    I’ve already listened back through this episode in full 3 times and I’m sure I will come back to it again in the future.