đź“– Read the full transcript of this episode
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In this episode, Andrew sits down with Derek Sivers, a writer, programmer, and entrepreneur turned explorer, who challenges everything you thought you knew about success and fulfillment.
From giving away millions to embracing the unexpected, Derek’s approach may be the antidote to our never-enough culture.
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00:00 - Intro
00:19 - Useful Not True
03:35 - How Derek Comes Up With Book Topics
07:35 - Spending the Past 15 Years Exploring
12:06 - Optimizing for Personal Growth
14:52 - Burning Ships
20:27 - Negative Impacts of Wealth
22:14 - The Burden of Philanthropy
26:17 - A Day in Derek’s Life
28:53 - Is Derek Introverted?
30:12 - Derek’s Hard No’s
35:35 - Derek’s Nomadic Blood
38:01 - Derek’s Fame
42:38 - Derek’s Thoughts on AI
57:12 - Overcoming Prejudices
59:25 - Doing What Scares You
1:01:54 - Learning to Appreciate China
1:06:48 - Closing
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Website: https://sive.rs/
His Now Page: https://sive.rs/now
His Latest Book: https://sive.rs/u
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Never Enough Podcast - EP-07: Derek Sivers Source: https://www.youtube.com/watch?v=1bZOWiXh8mo Title: This Entrepreneur Gave Away His $22 Million Dollar Fortune - Derek Sivers on Burning the Ships ================================================================================ an Explorer is a pain in the ass to follow the Explorer may change his mind daily and a leader goes in a straight line a leader says here’s where we’re going here’s how we’re going to get there follow [Music] me what are you interested in right now what are you obsessing over oh my useful not true book not for the sake of selling a book you know I don’t care about that but um just the subject of choosing beliefs because they’re useful not because they’re true last night I spent hours writing and thinking about what is it that makes beliefs useful like what do useful beliefs have in common and I came up with some traits things like you know instead of getting into specific beliefs traits like they help me go directly for what I really want instead of some roundabout way
right so if you’re I mean this is kind of the Never Enough theme right that if you’re thinking that you need a college degree to get status well then maybe there’s a more direct way to go directly to the status instead of four years of college another trait is useful beliefs are often selfless you kind of zoom out and realize you’re just one of many billions on Earth and what’s better for them is the greater good then instead of something that only benefits you and none of them and uh things like that I so just this has been on my mind a lot uh the general theme of beliefs that are useful not true I just did an interview with Mark Manson and uh he I was reading his book before the interview the latest book and he basically says look the world is pointless life is meaningless but you need something to hold on to is it that sort of thing like inventing truths for yourself even though they
are not necessarily inherently meaningful and life doesn’t matter could be see I think Mark is just projecting his value there saying you need something to hold on to I’d say that’s not true that’s just him saying this works for me and I’m going to prescribe it for others because I think many could benefit from this but it’s not necessarily true cuz for example I don’t need something like that I don’t need something to hold on to so that’s not an absolute truth how did you come to write that book what was the thought you kept coming back to it was more that the subject was underneath everything I had been talking about for years like you know my anything you want book I’m saying things in there like business is not about making money business is a way about making a little Utopia where you can make everything the way you want it to be well that’s not necessarily true that’s just that’s just one point of view that helps
me it helps me get more intrinsically interested in creating a good business because money itself doesn’t motivate me so I’m sharing a perspective that I’m choosing to adopt because because it works for me but the harm is in declaring it to be absolutely true like everybody needs to do this I’ve always been sharing beliefs that are useful to me that are not necessarily true and every now and then people would push back on one saying hey that’s not true and I’d say I know it’s not true I never said it was true I choose beliefs because they’re useful to me not because they’re true and after saying this for years I thought I should write a book about this is that generally how you come with your book topics like how do you differentiate between what you would do as a blog or just mention on a podcast or a book this is book number five for me and the five books have come from four different motivations so the
first book anything you want for one I never intended to write a book but you know Seth Goden called me and asked me to so of course I said yes but that one I just wanted to be done with the subject I’m like this is something I did in my past people keep asking me about I just wanted tell my tale and close that chapter of my life the next two books were collections of articles I had already written on my site and I wanted to put them into a book because I knew what was coming next and so my fourth book how to live was a flash of artistic inspiration like I just it was almost like a uh an art piece that took me four years to make like I had this idea for this thing I wanted to exist this book where it had 27 chapters each with a strong opinion of how to live and each chapter disagreeing with the rest I had that moment while
driving down the road where I went oh my God I want to do that and it just took four years to make it happen but I knew chronologically it was going to take a few years so that’s why I wanted to put out your music and people and hell yeah or no before that book came out so that my books could be at least somewhat chronological and then this new book useful not true like I said there was just an idea that just kept coming up kind of in between the lines or under the surface and I just thought there’s a there’s something more here to dive into so I spent the last two years learning more about the subject I went and read 20-some books about pragmatism denialism religion cognitive behavioral therapy and all of these subjects around the idea of choosing beliefs that are useful to you not because they’re true and just learned a lot more about the subject and then now I’m sharing what I’ve learned
do you think that you write to sort out your own ideas like is it are you doing self therapy or are you doing it for others so they can benefit from things you’ve already realized that’s a good question the books are for others ooh well I don’t know let me refine that that book how to live that was just for me meaning I needed this thing to exist I thought it was the most beautiful idea I was doing it to put into the public it wasn’t just I knew it wasn’t just going to stay in my private diary but if even if nobody liked it I wouldn’t care cuz I was so happy with it do you do it to codify an idea and then do you revert back to it so do you say like well this is how I live do I go back to my own values or do you just change and in 10 years that book won’t relate to you well that book in particular
I think will always be relevant because it has these 27 different conflicting yeah but the new book useful not true yeah that one did have a different motivation where I was doing it to help me solidify my thoughts how do you say codify something like that my thoughts on this subject and that might be interesting to go back to and refer to in the future do you look at any of your writing and cringe like do you go I don’t I can’t relate to that person anymore no do you do you have you ever had that no I think I’m relatively stable like I look back at Old blog posts and I still generally agree although I know that I’m different and I have different motivations on that topic I’m actually really curious I’m 38 you’re I believe 54 is that correct yeah 54 yeah what was 38 to 54 like so you know going from the period where you’re making money and you sell your business and all that
what was that what’s the last 15 20 years looked like for you and how have you changed the last 16 years have been a lot of exploration I think about the difference between an Explorer and a leader where if you think of the classic case you know I’m here in New Zealand which was the land that was I think most recently discovered on Earth so you think about about the classic case of an Explorer goes off to this new Uncharted land and just starts poking around taking every little turn following Every Little Creek going up hills going into valleys just looking around but an Explorer is a pain in the ass to follow because the Explorer may change his mind daily about what’s worth doing but that’s part of being an Explorer but then when the Explorer finds say a harbor the looks like a great place to set up a town or a port then the Explorer sends a message back to the queen who will an appoint a
leader to get people to set up a a port in this new Harbor that the Explorer has found and a leader goes in a straight line a leader says here’s where we’re going here’s why it’s great here are the benefits you’ll get from going there here’s how we’re going to get there follow me and a leader does not explore a leader just goes one place and that’s why a leader is easy to follow and I think about that internal metaphor where there are times in our life when we’re head down like a leader going one way doing one thing and there are times in our life when we lift up our head like the Explorer and just poke around and try lots of stuff and so I had God 15 years of my life more no God like 20 years of my life 24 years of my life from age 15 until 38 I was head down and focused on one thing I was not an Explorer I did not
read books I did not care to learn new things I spent 10 years just head down going I’m going to be sorry 15 years head down saying I’m going to be a successful musician that’s it don’t distract me with anything else I don’t care to hear about your stupid travels I don’t care about your stupid philosophies I’m here to be a successful musician and that’s all I did for 15 years from age 14 to 29 was head down on this one thing then at 29 while selling my music I accidentally started my company and then I just put my head down for 10 years on that one thing I was like I’m gonna make the best damn little record store and I did that for 10 years and so it wasn’t until I was 38 that I really lifted up my head for the first time in my life you know I kind of where am I what’s going on huh and I started doing things the opposite of whatever
I had been doing at any moment on just day-to-day basis if every in my instinct was telling me to turn left I would turn right and if everything in me was telling me to stop I would go and I did that to deliberately scramble my patterns and force exploration so I feel like that’s still what I’ve been doing for most of the last 15 years when I met you I hadn’t seen you I don’t think in 15 or even 20 years I think we met at the Ted conference in 20 eight or something like that and I looked you up I was in Wellington and we had coffee and you told me you I I was kind of going through a challenging time uh trying to get my head straight trying to figure out what my second Mountain was was I going to be a leader or an Explorer myself and you said something really interesting you said when you sold your company your urge was to do it again
to prove to the world that you were not a fluke and you said I wasn’t going to I ended up deciding that I wasn’t going to play the same game that I’d been playing that I’d already done that can you speak to that a little bit I optimize for personal growth not for bank account growth or status growth so when I sold CD bab yeah my first thought was I can leverage this uh I’m going to go to Silicon Valley right now and jump into the middle of that thing and be uh a Serial entrepreneur and I’m going to do it in the place where you know it all happens and I got just a few months into that and I realized that if I were to do that it wouldn’t really be personal growth it would be bank account growth and Status growth but I’d be doing the same stuff I had been doing for 10 years I would just swap out the company name over my
head with a different company name but I’d be doing the same thing I thought well real growth would be to do something truly different not doing the same thing it’s kind of sorry I’m reminding myself of a lovely little quote I heard once that real Rebellion is not wearing black like everyone else real Rebellion feels like wearing a clown suit to high school like that would be true Rebellion so I think that same thing with personal change true personal growth is not doing the same thing you’ve been doing but a little more real personal growth at least for the kind I was looking for was to do something truly different and as soon as I realized that and felt it I halted my plans completely instead of I left uh Silicon Valley and I went to India and Iceland and started traveling the world and like I said I just deliberately made myself do the opposite of what I had been doing I went to New York City was dating
this girl for a while she said well I come from a really strict religious family um I we got I can’t travel with you unless we’re married and everything in me said no I don’t even know you it’s only been a few months so I was like oh all right all right sure I’ll marry you because it was the opposite of what my instincts were telling me and um I could say that some of these things are regrets but in the bigger picture I wonderfully scrambled my life and I I don’t regret it in the bigger sense I think it was the right thing to do it’s led to a much Fuller life and I hope to keep doing it I hope to keep scrambling when we met you used the term burning the boats you talked about how you took radical change to enforce that you would not continue down the path of money and business how did you do that yeah well the the most
direct radical one was renouncing my US citizenship which again again came from this process of saying I love America it’s my comfort zone California New York City most of the stuff in between I just love it therefore I’m going to ban myself from going there anymore but I had said that to myself once before in 2007 or 2008 but yet as soon as things got a little difficult overseas I retreated back to America so this time I wanted to make sure that I wouldn’t Retreat again so I used the metaphor of burning the ships which was an old Legend apparently true who cares of the Navy general with say 100 men on three ships landed on enemy Shores and there are thousands of enemies waiting to kill them and so he turns to one of his men and he says burn the ships no retreat we must push forward and it it was a way of preventing Retreat so I renounced my US citizenship as a way of
preventing Retreat for myself and it’s worked there were a couple times in the Years afterwards where I felt like could just just like to just go back to LA go back to New York and I thought well I can’t so that’s that I have to keep pushing forward you also did that with your finances I remember you told me that you sold the business and you burned the boats there what did you do there cuz I think it’s very very unique I think it’s very counterintuitive yeah thanks for that reminder I hadn’t really thought of that as a burning the ships but oh my God you’re right to give context to The Listener I already had about $4 million in my personal bank account as net profit I was the sole owner of the company it was a profitable business no investors just bootstrapped with $100 and um and I had 4 million in profit and at that point then I had this agreement to sell the company for $22
million and I thought through about what I would do with $22 million and I just thought I just don’t want it I mean the 4 million I had saved up was after expenses I had already bought a car and bought a house there I mean what else are you going to do with it anything you do with it after that is pretty stupid sorry Andrew so um but um so I thought I’m just going to give it away I mean there are people like literally dying because they don’t have money and I’m sitting here trying to figure out what to do with my money well duh give it to people who need it so luckily I had a lawyer that had a background in tax law and luckily he just happened to ask me what are you going to do with the money and I said I’m just going to give it away and he said how serious are you I said very serious he said like irreversibly permanently serious
like no going back I said yeah that sounds great and he said all right well if you’re really serious we haven’t done the deal yet we can structure this so that you can transfer your company into a charitable trust now and instead of the the company paying you $22 million you paying a third of that to the IRS and you giving away 15 million to charity we can structure it so the entire $22 million goes to charity and I said oh I like that because then the money never touches my hands I can never be tempted with it I can never go like oh I’ve changed my mind I want a big stupid boat you know I can’t I thought yeah I like that a lot so that’s what we did and how do you live now what’s your income I mean like I said I had that $4 million and that has grown since then I just stick it in ETFs in a Schwab account and it’s grown a
lot since 2008 and then I got really lucky with timing where um I when what did I do I bought a house in England and then I I sold the house at a point and I and I put everything back into ETFs right in like February 2020 when Co had sent the stock market on a deep sharp dip that just with lucky timing ended up to be the day that I got back into the market and that cash like it almost doubled within you know a year from the day I put it in so yeah things like that just to pay my cost of living and that’s fine I really occasionally turn to my private journal and I ask myself like what would I do if I suddenly had a billion dollars and every time I really think hard I just can’t think of anything I would do with it like just there’s nothing I want so I I still think I did the right thing you’ve got a lot
of friends that are very very wealthy how do you see wealth negatively impact their life it seems to throw off perspective my first anti role model on this subject was a year before I sold my company I met a friend who had sold his company for 30 million a year before mine and he talked about how he bought his house in London and he said yeah it was a nice house and it was only 10 million pounds so we thought yeah why not and I was like God I hope I never say that I hope I never say it was only 10 million pounds I think that’s harmful I think that’s we should never lose perspective on how much money that is and how much that money could be doing for the world and sorry if I sound like a hippie like this but I do often like I don’t see a big distinction between me and others like I don’t think I’m so much
more important than other people so I’m often thinking in these terms of like well what I’m already good my basic needs are met what does the world need like the world doesn’t need me to have a boat the world doesn’t need me to have a six-bedroom mansion it’s like the goose that lays the golden eggs you don’t want to sacrifice the goose so I do look after myself I’m not sacrificing myself but after that it just doesn’t make sense um so any sorry to answer your question I think the only downside is people who kind of lose perspective on how much money that is did the money that you put into the foundation become a burden at all like I mean that’s a lot of money $22 million to give away how did you give it away if it would have been one of those public foundations where people would have come to me all the time going please give me some please give me some that
no way I would hate that that would oh God wouldn’t that be awful it would be like choosing to live on the street with all the homeless people like it would be choosing to subject yourself to that every day like oh God God this is making me feel awful you know to just like so no no no I set it up so that while I’m alive the charitable Trust keeps that 22 million and it it invests it and re and compounds it and so when I die hopefully it’s like a 100 million by then and that’s when all the money goes to charity when I die so I’m not even the trustee it’s out of my hands it’s totally out of my control out of my hands when I die it all goes to charity so no it’s no constant handout one of the things that I hear from people who do philanthropy though is that it makes them feel good to do it while they’re living
and enjoy that giving so you’re not going to get to feel that is there a reason why you did that versus just like giving it all away to a charity and getting to enjoy that feeling of giving it away versus it happening after you’re dead I don’t get that much joy from charitable giving I get a little it’s more just it feels rational like well here I’m not using it you can use it um I don’t think it makes me a good person um I don’t get warm and fuzzy from it it just feels like all right well it’s just logical here I’m not using this money you guys need it here it is I remember um I had a a very wealthy client when I was running my web design agency and I met with them on a day where there was a school shooting and it was a really sad event but this person was so affected by it and they were working on gun legislation they were
trying to you know do an assault weapon ban or something in the United States and the exact weapon that they had been trying to ban was used in this school shooting and so they felt the weight of the world on their shoulders and I often think for you know philanthropists are basically saying I can solve The World’s problems and I think that’s incredibly stressful you know you’re holding a boulder up the moment I was trying to avoid is having to make the moral decision of saying yes or no to people that are asking for money that’s what I didn’t want to have to do people coming to me saying please we need this it’s for the children and somebody said please need you know we did this it’s for the people dying of this disease and then somebody else might say please we need this to preserve Our Heritage it’s like well I don’t know where do I draw the line your heritage but save the kids
the kids but save the disease I don’t know I wouldn’t want to have to spend a minute of my day thinking like that I’d rather just get back to doing what I intrinsically motivated to do so that’s what I was I was trying to more avoid the the confrontational decisions all the time so that’s why I kind of like just put it in trust that goes to the ETFs when I die it goes to give well.org they’ve already done their nerdy uh calculations of what is the best usage of money to save the most lives I get to stay out of it I don’t play favorites I don’t say well this is the cause that I believe in and this cause moves me and that one doesn’t instead of just say all right there just none of this really moves me I’m actually not that interested in it so since then you’ve left the idea of accumulating money behind and now how do you spend your time
like what what does the day in the life of Derek Sivers actually look like a typical day for me is I don’t know why I wake up at 4:00 or 5 a.m. I wish I didn’t I wish I slept more but for some reason every morning about 4:30 or 5 in the morning my brain goes I’m ready let’s go and I get up and I start writing and I am either writing Diaries books code emails basically finger on Keys writing from 5:00 a.m. till about 10 or 11 p.m. with some short breaks to eat maybe take a walk in the forest uh play with my kid but for the most part 5:00 a.m. to 10 p.m. is writing and that’s my day and then I do it again and you have a newsletter you have books you blog what how do you look at each of those different things and what does it do for you what are you exploring in each of those Realms I don’t really have a
newsletter to be fair I I have my blog and I have my books and that’s it I thought when we met you were like I just got back from India and I had you know 14 random people that were from my newsletter that I just met up with for the fun of it what was that I have an email list of people that have emailed me over the years so there’s like a quarter million people that have contacted me but it’s it’s a two-way conversation it’s not a newsletter blast it’s people who have contacted me over the years and introduced themselves and we email back and forth and then when I’m coming to wherever they live whether it’s uh Uruguay or Helsinki or Brazil um then I’ll email them and say hey I’m coming to Montevideo would you like to meet up and that’s where I kind of meet people that have emailed me over the years but I just want to be clear it’s not like a substack newsletter
I don’t have like I don’t have a stream of content I diary a lot to sort out my thoughts on various things whether it’s programming or just life decisions or just thoughts about random things that come up in life I do most of my writing private when I come up with something that seems worth sharing I’ll make a version for the public which is much more succinct than my rambly thoughts in a diary so you might spend like 16 hours and you’re just dwelling on a problem that you’re thinking about and are you what kind of writing tool are you in oh I just use Vim in the in the terminal um yeah everything’s in terminal in in Vim if you’re spending 16 hours a day writing and kind of being on your own are you introverted yes and no I am super super interested in people it’s actually a bit of a circumstance that I am where I am in New Zealand because I moved here to raise my
kid but the thought was that we would leave here by the time he was seven or eight to go to somewhere more Cosmopolitan more multinational and instead his mother got a job at the New Zealand government and this is where all her friends are and she just didn’t want to move so I never intended to be here more than a few years but I I both fell in love with the country and have the circumstance of my boy’s mother uh needs to stay here so I would much rather personally be living in a super Multicultural place like Dubai London um something like that where I’d like to be meeting with more people from around the world and getting to know different viewpoints but since I can’t do that in person I think that’s why I keep my email inbox open and I love hearing from people around the world and emailing with them every day so you wrote a whole book called hell yeah or no I’m curious what are
some of the things that you are hard no on how what are rules you’ve created for yourself to prevent yourself from going in bad directions never do heroin um that’s a good one here’s one when I say something like oh man I I just went to Dubai for my first time and by the way we should talk about that later because it’s one of the most interesting things that’s happened to me in years um and I’ll say oh man I wish I was in Dubai and every now and then somebody will say well why don’t you go then and I’d say well because my boy’s here and they say he’ll be okay without you and I’ll say no no hold on you’ve missed the whole point and this is the answer to your hard no question there are a hundred other things I could be doing right now but I’ve made a really clear decision that my boy is my top priority I’ve only got one kid this is
it I’m not going to have others he’s my top priority above all else so even though there are other things I’d like to be doing number one is I I want to be with him he and I talk almost every day uh we I’m a part of his life we’re like best friends and he wants me to to be here in his life so I want to be here where he is even though I know I could just hand him off to his mother and go be somewhere else he’s my top priority so I think my only real hard no in life is anything that would hurt our relationship but you’re you’re separated from your his mother do you guys do custody like do you have a week off and that’s when you could travel and you won’t travel in that week it’s like half week each every week so you know half the week with me half the week with her I like that a lot I just um
unintentionally had a trip and it I did it was the week I didn’t have the kids and um I planned a trip with a bunch of meetings and you know stuff for the book and talking to reporters and all this stuff and then I realized that my son’s grade one graduation was on the day that I had a meeting with the Wall Street Journal and I did the Wall Street Journal thing and I completely regret it and feel really sad about it and so hearing you say that I think is reaffirming to um Implement that rule I think that’s important depends how much it meant to him I don’t know if he cares it’s hard to gauge but you know when you’re in grade one like you don’t really emote to that degree let me do a flip side and this matters because my kid is 12 now so he is able to articulate things there was a time six years ago let’s say
where I had the opportunity to go to the Ted conference that was going on in Arusha Tanzania I’ve never been to Africa and here I was supposed to attend Ted Global in Arusha Tanzania I was so excited I know they’d been sending out their announcements about Ted conferences in you know England and Vancouver I was like eh I was like holy crap Arusha Tanzania yes absolutely holy crap hell yeah um signed up paid booked the flights booked the hotel not only that I was going to go to Tanzania a week beforehand to the island of Zanzibar where I was going to be staying at the house of a musician’s collective in Zanzibar I was like God I’m so excited I was so excited to do this but then a week before that trip was this Esperanto conference I went to in Seoul Korea and and uh so I went to the Esperanto conference in Seoul Korea and then as I was in Singapore for a couple days about
