The guest
Derek Sivers: Entrepreneur turned author who founded and sold CD Baby; minimalist writer known for books like Anything You Want, now living in New Zealand.
What this episode covers
Tim Ferriss and Derek Sivers cover an enormous range over Scotch and tea in Wellington, New Zealand. Sivers shares a detailed, notes-driven walkthrough of achieving 'tech independence' by getting off the cloud, running your own server, and self-hosting contacts, files, websites, and email. He then unpacks his philosophy of the 'unoptimized life' and satisficing versus maximizing, and lays out his four-part 'Useful Not True' framework of radical skepticism. The conversation also dives into identity and labels, choosing customers you love, how he uses imagined mentors, and a series of personal 'giant leap' decisions including renouncing his US citizenship and selling his company.
Recommended on this episode
ProductRecommended
Vultr Cloud Compute
Vultr
“Go to a company I recommend called vultr.com”
“the first thing you need is to get your own server, which is as simple as $5 a month. Go to a company I recommend called vultr.com”— Derek Sivers
ProductRecommended
Lenovo ThinkPad T400 series
Lenovo
“find an old used Lenovo ThinkPad, ideally from the T400 series ... they're great”
“find an old used Lenovo ThinkPad, ideally from the T400 series. You can get these for under $200 now and they're great”— Derek Sivers
ProductRecommended
OpenBSD
OpenBSD Project
“the operating system I'm going to recommend, the one I use is called OpenBSD”
“the operating system I'm going to recommend, the one I use is called OpenBSD”— Derek Sivers
ProductRecommended
BookMyName
BookMyName
“My recommended place to get a domain name is a wonderfully nerdy, non-commercial site called BookMyName.com”
“My recommended place to get a domain name is a wonderfully nerdy, non-commercial site called BookMyName.com”— Derek Sivers
ProductRecommended
NETIM
NETIM
“All three of these are really good, reputable places to get a domain name. I recommend them.”
“As a backup, I use NETIM.com. Both of these are French companies”— Derek Sivers
ProductRecommended
Porkbun
Porkbun
“All three of these are really good, reputable places to get a domain name. I recommend them.”
“a third one in Portland, Oregon that I like called Porkbun.com. All three of these are really good, reputable places ... I recommend them”— Derek Sivers
ProductRecommended
Radicale
Radicale
“It sets up what's known as a CardDAV and a CalDAV server ... it's dead simple. Blew my mind.”
“you can set up it's called Radicale. The website is Radicale.org. It's absolutely free. Open source.”— Derek Sivers
ProductRecommended
rsync
“Every computer has this dead simple little program built into it called rsync”
“Every computer has this dead simple little program built into it called rsync. Macs have it built in.”— Derek Sivers
ProductRecommended
Syncthing
Syncthing
“there is a free replacement for Dropbox called Syncthing ... It does that more like automatic style”
“if you're a fan of Dropbox, there is a free replacement for Dropbox called Syncthing. Syncthing.net. It's totally free open source.”— Derek Sivers
ProductRecommended
Mailbox.org
Mailbox.org
“The simplest, cutest little one I've found is Mailbox.org ... They're cute, they're great. They're all privacy focused.”
“The simplest, cutest little one I've found is Mailbox.org in Germany. For $1 a month they do nothing but host your email”— Derek Sivers
ProductRecommended
Fastmail
Fastmail
“the best email client on earth, you go to Fastmail.com. Fastmail.com is amazing.”
“If you want the luxury full premium suite of like the best email client on earth, you go to Fastmail.com. Fastmail.com is amazing.”— Derek Sivers
ProductRecommended
Ruby programming language
“So I love the Ruby programming language”
“So I love the Ruby programming language. And before there was Ruby on Rails, I learned Ruby in a cabin in Sweden”— Derek Sivers
MediaRecommended
Stumbling on Happiness
Daniel Gilbert
“After I read Stumbling on Happiness, I went, "Ooh, that was good. That was a good book."”
“After I read Stumbling on Happiness, I went, "Ooh, that was good. That was a good book."”— Derek Sivers
MediaRecommended
The Moral Landscape
Sam Harris
“The best TED talk I've ever seen. Ever.”
“go search for Sam Harris. Moral Landscape. The best TED talk I've ever seen. Ever.”— Derek Sivers
BookRecommendedISBN verified
What Everyone Needs to Know About Islam
John L. Esposito
“I recently read a book I can recommend for anybody called What Everyone [Needs to] Know About Islam. And it was really good.”
“I recently read a book I can recommend for anybody called What Everyone [Needs to] Know About Islam. And it was really good.”— Derek Sivers
BookRecommendedISBN verified
A Guide to the Good Life
William Irvine
“Whoa! Oh, my God. I thought this was just me. Like, this is everything he's talking about.”
“finally in 2010, I read A Guide to the Good Life ... Whoa! Oh, my God ... This is the way I've been thinking”— Derek Sivers
BookRecommendedISBN verified
How to Stop Worrying and Start Living
Dale Carnegie
“It's a great book, by the way, folks. How to Stop Worrying and Start Living by Dale Carnegie.”
“It's a great book, by the way, folks. How to Stop Worrying and Start Living by Dale Carnegie.”— Tim Ferriss
BookRecommended
The Work
Byron Katie
“And I found personally very useful. Super, super useful.”
“There's something called "The Work" by Byron Katie, which is very much this. And I found personally very useful. Super, super useful.”— Tim Ferriss
MediaRecommended
Stardew Valley
ConcernedApe
“If you want to play a great game that is also non-greedy ... Stardew Valley is wonderful.”
“If you want to play a great game that is also non-greedy ... Stardew Valley is wonderful.”— Derek Sivers
BookRecommendedISBN verified
How to Get Rich
Felix Dennis
“the audio book is exceptional ... I love that book.”
“Felix Dennis's book called How to Get Rich ... the audio book is exceptional ... I love that book.”— Tim Ferriss
BookRecommendedISBN verified
Genghis Khan and the Making of the Modern World
Jack Weatherford
“Great book ... Especially the first half or so, is really exceptional.”
“I read Genghis Khan and the Making of the Modern World ... Great book ... Especially the first half or so, is really exceptional.”— Tim Ferriss
MediaRecommended
Helvetica
“Helvetica, which is a great documentary about type font typefaces and fonts ... Really cool doc.”
“It wasn't Helvetica, which is a great documentary about type font typefaces and fonts and so on. Really cool doc.”— Tim Ferriss
BookRecommendedISBN verified
The Art of Learning
Josh Waitzkin
“I loved his book, The Art of Learning.”
“I loved his book, The Art of Learning. And I've listened to his interviews, and I really admire him.”— Derek Sivers
MediaRecommended
Saga
Brian K. Vaughan and Fiona Staples
“Highly recommended, by the way. Saga. Best graphic novel.”
“He's read the Saga comic books ... Highly recommended, by the way. Saga. Best graphic novel.”— Derek Sivers
The guest's own work
BookBy the guestISBN verified
Anything You Want
Derek Sivers
“Anything You Want. I recommend people check it out. I've read it multiple times. It's a great book.”— Tim Ferriss
BookBy the guestISBN verified
The 4-Hour Body
Tim Ferriss
“It actually reminded me of something you said in The 4-Hour Body about yoga studios”— Derek Sivers
BookBy the guestISBN verified
The 4-Hour Workweek
Tim Ferriss
“your introduction to the world in four hour workweek, giving so many wonderful examples of how you don't have to accept the world's norms”— Tim Ferriss
Also referenced (named, not recommended)
BookReferencedISBN verified
The Paradox of Choice
Barry Schwartz
“if you have not read The Paradox of Choice by Barry Schwartz, he talks about maximizers and satisficers”— Tim Ferriss
MediaReferenced
Sartorial Talks
“So I looked at Sartorial Talks — an interesting YouTube channel diving deep into like the the craft of fine clothing”— Derek Sivers
BookReferencedISBN verified
Excellent Advice for Living
Kevin Kelly
“Kevin Kelly in his new book, called Excellent Advice for Living, said, "You know how you have that bad pen? Throw out the bad pen."”— Tim Ferriss
ProductReferenced
Mailgun
Mailgun
“for sending I actually use a service called Mailgun that just handles the sending so they take care of all the deliverability”— Derek Sivers
ProductReferenced
SendGrid
SendGrid
“I think SendGrid does handle some of this as well ... SendGrid. Those guys have done such a good job”— Tim Ferriss
ProductReferenced
Ruby on Rails
David Heinemeier Hansson
“there was this guy named David in Denmark who was doing something with websites and Ruby ... then Rails came out about eight months later”— Derek Sivers
ProductReferenced
Shopify
Shopify
“I was thrilled later to find out that Tobi's little e-commerce thing was Shopify”— Derek Sivers
MediaReferenced
Wicked
“we found ourselves right in front of the West End musical, Wicked ... Yeah, let's do it. Let's go see Wicked.”— Derek Sivers
BookReferencedISBN verified
Think and Grow Rich
Napoleon Hill
“Napoleon Hill talked about the mastermind. Imagine Abraham Lincoln is there. What would Abraham Lincoln say to you?”— Derek Sivers
MediaReferenced
Somebody That I Used to Know
Gotye
“Gotye. (singing) "You didn't have to cut me out. Now you're just somebody that I used to know."”— Derek Sivers
MediaReferenced
There's Something About Mary
“I suddenly, after watching There's Something About Mary with my kid, I said, "I wonder what ever happened to her."”— Derek Sivers
MediaReferenced
The Last Emperor
“What is at the end of the movie The Last Emperor. This guy has been through this big giant arc.”— Derek Sivers
Big reveals from this episode
- Sivers recounts his Iceland scuba diving panic attack and rescuing a panicking German diver the next day, teaching him that categories like 'panic-attack person,' 'hero,' or 'rescuer' can be involuntary and that empathy means recognizing 'this might be you.'
- He lays out concrete tech-independence steps: get a $5/month virtual private server from Vultr, run OpenBSD, generate SSH keys to disable password logins, and lock the firewall to port 22.
- Self-host contacts and calendars with Radicale, file sync with rsync or Syncthing, your own static HTML website, and get email onto your own domain via Mailbox.org, Fastmail, or your own server with Mailgun for outbound sending.
- The 'cardboard box' story: an unplanned eight-hour wander through London with his son led to the boy's favorite moment being a cardboard box, illustrating the value of an unoptimized, plan-free life.
- Sivers introduces 'Useful Not True' as deep skepticism, framed by the four tenets: almost nothing is objectively true, beliefs are placebos, rules and norms are arbitrary games, and refuse ideology by taking ideas piecemeal.
- The Oslo hotel story: a 'risque' tale of a liberating realization that he'd done nothing wrong despite an angry hotel clerk, teaching that you're free from authority and judgment as long as you don't break the law.
- He reveals he renounced his US citizenship in 2011 to 'burn the ships,' now calls it one of his biggest mistakes, and explains it raised his taxes and reduced his options.
- His mentor method: he hasn't actually talked to his mentors in years (one doesn't know he exists) because writing a succinct summary and predicting what they'd say resolves the dilemma himself.
Worth remembering
- Sivers owns only three drinking glasses and one pair of pants, embodying his 'enough' minimalism.
- One business idea he's considering is '100-year hosting' - legacy personal websites set up in a trust to last 50-100 years after you die.
- He cites a tech-savvy Singapore entrepreneur who lost 10 years of his kid's photos by merging his Gmail with a Google Apps for Business account.
- Tim's effectively-'fuck off' email address and the story that Tobi (Shopify's founder) once taught Sivers Ruby on Rails over the phone for $100.
- Sivers learned the Ruby programming language during two weeks offline in a cabin in Sweden, then emailed DHH who replied only 'Not ready yet.'
- He put an offer on a nicer house, got it accepted, then yanked it the night before the deposit after realizing 'I'm already happy.'
- He cites split-brain patient studies where people confidently invent false reasons for their own actions, supporting his point that you shouldn't even believe what you tell yourself.
- He references Sonja Lyubomirsky's finding that happiness is roughly 50% DNA and 50% within your control.
- Sivers had independently held Stoic beliefs since age 16 (from his grandmother's copy of Dale Carnegie's How to Stop Worrying and Start Living) and only read formal Stoicism at age 40 via William Irvine's A Guide to the Good Life.
- He invokes Kevin Kelly's maxim 'The best option is the option that gives you the most options' to argue against renouncing citizenship.
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