Derek Sivers on Giving Away His $22 Million Dollar Fortune and Burning the Ships

10/04/24 • 70 min

About the episode

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.
Join us as we explore:

Why he gave away his $22 million dollar fortune.
Why he's an explorer not a leader.
How he has "burned the ships" over and over again.
His annual ritual for reversing prejudices.

And so much more.
Chapters

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
🔗 Find Derek on:

Website: https://sive.rs/
His Now Page: https://sive.rs/now
His Latest Book: https://sive.rs/u
🔗 Find Andrew on:

Twitter/X: @awilkinson
LinkedIn: @awilkinson
Website: https://www.neverenough.com/
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Why he gave away his $22 million dollar fortune.
Why he's an explorer not a leader.
How he has "burned the ships" over and over again.
His annual ritual for reversing prejudices.

Previous Episode

Codie Sanchez on Buying Boring Businesses and The Secret to Wealth

About the Episode
Can the path to financial freedom be paved with boring businesses?
In this episode, Andrew sits down with Codie Sanchez, a founder, entrepreneur, and investor who's redefining success in the business world.

Codie is the founder and CEO of Contrarian Thinking, a digital education company with over 7 million followers, and Main Street Hold Co, a small business holding company. She's also the driving force behind Contrarian Thinking Capital, a firm investing in companies that support small business growth.

In this conversation, Codie shares her journey from working in private equity to becoming a champion for Main Street entrepreneurship. She discusses the power of "boring" businesses, the importance of deal clarity, and why she believes ownership is under attack in the U.S. Codie also offers insights from her upcoming book, "Main Street Millionaire," which promises to be an MBA-level guide to mergers and acquisitions for everyday entrepreneurs.

Join us as we explore

Codie’s journey from working in Vanguard to owning multiple businesses of her own
The appeal of boring businesses
Strategies to help you know whether the businesses you want to buy or start are actually any good
AI and technology’s impact on businesses and the job market
Codie’s perspective on fame, navigating challenges, and her aspirations
People and products that she’s been loving lately

Maybe you’re itching to start your own venture. Or perhaps you’re an investor looking to expand your portfolio. Codie’s insights will surely steer you towards success. Tune in for a powerful conversation that unpacks the secrets of what it takes to win in business.

People Mentioned

Resources Mentioned

Chapters
00:00 - Intro
00:42 - Catching Up With Codie
5:01 - Codie’s Entrepreneurial Journey
8:51 - Why Boring Businesses Are Great
13:23 - What Businesses Do You Buy?
16:07 - How to Tell If Your Businesses Ideas Are Good
18:37 - Weird But Profitable Businesses
21:24 - Businesses AI Will Disrupt
23:33 - Integrating Tech In Businesses
25:15 - White Collar Workers Shifting to Blue Collar Jobs
30:57 - Fame’s Impact on Codie’s Life
36:00 - Codie’s Goals For the Future
37:51 - Dealing Tough Days
41:53 - Codie’s Book
43:48 - Codie’s Product Recommendations
47:38 - People Codie Finds Interesting
🔗 Find Codie on:

Twitter/X: @Codie_Sanchez
Instagram: @codiesanchez
Tiktok: @realcodiesanchez
Youtube: @CodieSanchezCT
Website: https://www.codiesanchez.com/
🔗 Find Andrew on:

Twitter/X: @awilkinson
LinkedIn: @awilkinson
Website: https://www.neverenough.com/
Sign up for Andrew's newsletter

Next Episode

Designing Your Digital Mind: Charlie Grinnell's AI Journaling System

About the episode

In this episode, Andrew chats with Charlie Grinnell, the productivity-obsessed Co-CEO of RightMetric. Together, they get into his foolproof system for getting things done and how AI has revolutionized his workflow.
Tune in to learn how to boost your productivity and achieve more with less.
We go over

1. AI and Journaling: Charlie uses Reflect to transcribe his thoughts while he’s on his morning walk. It’s helped him reduce the friction of journaling.
2. Deep Work: “ I go for a walk and I do some journaling, which we'll talk about in a little bit here. I come back home. I do some deep work until I get to lunchtime.”
3. Keeping Track of Meetings, Book Quotes, & Interesting Podcasts: The Readwise app helps Charlie keep track of everything he reads and listens to.
4. Interesting AI Use Cases: Chatting with notes, journal prompts, and speech to text
And so much more.
Resources Mentioned

- Readwise
- Superwhisper
- EightSleep
- Lomi: Smart Waste Kitchen Composter
- Text
- Things
- Reclaim AI
- Basecamp
- Fathom
- Clay
Chapters

00:00 Intro
00:33 Getting to Know Charlie
3:17 Charlie’s Typical Day
5:15 Charlie’s Journaling Routine
11:56 Charlie’s Library of Journaling Questions
13:48 Facilitating Deep Work
15:39 Dealing With Low Priority Tasks
20:09 Avoiding Distraction While in Deep Work
21:19 Time spent in Deep Work
21:47 Charlie’s Favorite Type of Deep Work
23:19 Meeting Recordings, Transcripts, & CRMs
26:48 Charlie’s System for Reading
31:35 Keeping Track of Interesting Podcast Tidbits
34:22 Dealing With AI’s Recency Bias
35:57 How Charlie Keeps Consistent With His System
38:11 What Drives Charlie to Create Systems
42:18 Broken Parts of Charlie’s System
44:00 What Charlie’s Looking Forward to With AI
45:55 Other Interesting Ways Charlie Uses AI
49:30 Products Charlie Really Loves
🔗 Find Charlie On:

LinkedIn: @charliegrinnell
Twitter/X: @CharlieGrinnell
Instagram: @charliegrinnell
🔗 Find Andrew on:

Twitter/X: @awilkinson
LinkedIn: @awilkinson
Website: https://www.neverenough.com/
Sign up for Andrew's newsletter