Derek Sivers

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.

The gist

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.

Big reveals

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.'
00:05:36
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.
00:29:56
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.
00:39:36
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.
01:00:10
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.
01:12:46
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.
01:21:48
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.
01:48:02
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.
01:57:14

Things worth remembering

Sivers owns only three drinking glasses and one pair of pants, embodying his 'enough' minimalism.
00:01:04
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.
00:21:44
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.
00:27:44
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.
00:56:26
Sivers learned the Ruby programming language during two weeks offline in a cabin in Sweden, then emailed DHH who replied only 'Not ready yet.'
00:58:02
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.'
01:04:28
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.
01:16:06
He references Sonja Lyubomirsky's finding that happiness is roughly 50% DNA and 50% within your control.
01:39:36
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.
01:40:15
He invokes Kevin Kelly's maxim 'The best option is the option that gives you the most options' to argue against renouncing citizenship.
01:50:16

Recommended in this episode

Books, products and media the guest or host genuinely endorsed here — with the buy link.

Affiliate link — we may earn a commission at no extra cost to you.

Guest’s ownBook

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 00:16:11

Derek Sivers — Finding Paths Less Traveled, Taking Giant Leaps, and Picking the Right “Game of Life”

The gist

Big reveals

Things worth remembering

Recommended in this episode

Anything You Want

Vultr Cloud Compute

Lenovo ThinkPad T400 series

OpenBSD

BookMyName

NETIM

Porkbun

Radicale

rsync

Syncthing

Mailbox.org

Fastmail

Ruby programming language

Stumbling on Happiness

The Moral Landscape

What Everyone Needs to Know About Islam

The 4-Hour Body

The 4-Hour Workweek

A Guide to the Good Life

How to Stop Worrying and Start Living

The Work

Stardew Valley

How to Get Rich

Genghis Khan and the Making of the Modern World

Helvetica

The Art of Learning

Saga

Papaoutai

Topics