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

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/
Sign up for Andrew's newsletter

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

• Balaji
• Jonah Goldberg
• Ayman Al-Abdullah

Resources Mentioned

• Main Street Millionaire by Codie Sanchez
• The Triumph of William McKinley by Karl Rove
• The Vietnam War by Ken Burns & Lynn Novick
• Bach flower remedy
• Logitech Casa Pop-Up Desk

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

Museum Hack Founder and Author of The 2-Hour Cocktail Party, Nick Gray joins the podcast for an exciting conversation on the power of hosting and the ways in which it changed his life. From giving a tour to the Saudi Arabian royal family to hanging out with a billionaire in Asia, he openly delves into all his fascinating adventures while sharing practical tips on hosting and making friends.

Join us as we explore

• Nick’s journey from trying to start a software company in India, moving to NYC and building Museum Hack, to where he is now
• The art of active hosting and how to use it to meet interesting, new people
• Dealing with rejected invitations and importance of providing value to the people you meet
• His passion for adventure, along with tips for aspiring travelers
• The little things that Nick splurges on and uses everyday

If you’re someone who’s interested in learning about the best way to host a party or simply love a good adventure, Nick’s stories are sure to give you all the fun and insight you need!

Resources Mentioned

• The 2-Hour Cocktail Party by Nick Gray
• Storyworthy by Matthew Dicks
• Buckwheat pillow
• Weighted blanket
• Trello
• Upwork

Chapters

00:00 - Preview
00:50 - Mateina Yerba Mate
2:56 - How Andrew First Met Nick
5:08 - Nick’s Newsletter
6:01 - Starting a Software Company in India to Living in NYC
9:30 - Museum Hack
11:33 - Benefits of Having A Newsletter
14:25 - The 2-Hour Cocktail Party & Active Hosting
19:25 - The N.I.C.K. Method
23:03 - Prioritizing Adventure Over Money
24:34 - Growing Social Circles Through Hosting
28:33 - Nick’s Friendship Funnel
37:55 - Tips for Hosting
41:00 - Rejection With Invites
43:23 - Nick’s Favorite Hosts
44:28 - Adding Value to People You Meet
54:34 - Balancing Adventure With Routine
59:11 - Finding Interesting Experiences
1:03:01 - Nick’s Views on Travel
1:05:22 - Nick’s Blind Date in Tokyo
1:09:10 - Nick’s Investments
1:11:02 - How Nick Enjoys His Money
1:18:15 - Nick’s Daily Routine
1:22:43 - Nick’s Productivity System

🔗 Connect with Andrew:

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

🔗 Connect with Nick:

Twitter: @NickGrayNews
Instagram: @nickgraynews
LinkedIn: @nickgraynews
Youtube: @nickgray
Website: nickgray.net

Most known for his book The Subtle Art Of Not Giving A F*ck, Mark Manson is a three-time #1 NY Times bestselling author and entrepreneur. In this episode, he tackles questions, less about his books, and more about the business of being a writer. Can authors really make a living? Is the pursuit of fame and fortune really as glamorous as it seems? Mark also reveals what it’s like working in Hollywood, explaining why he believes the creator economy offers a brighter future.


Join us as we explore Mark's story and learn about:

• The business of the publishing industry
• Literature’s place in current society
• Hollywood’s inefficiency and the future of the creator economy
• The impact that fame and wealth has on people and relationships
• Mark’s current struggles as well as what he’s looking forward to in the future

Craving honesty over hype? Mark gives you the unvarnished truth. Don’t miss this candid discussion about his journey from broke blogger to bestselling author, the challenges of working with Hollywood, and the surprising lessons learned from achieving everything he ever wished for.

Resources Mentioned

The Subtle Art of Not Giving A F*ck by Mark Manson
Old Man in The Sea by Ernest Hemingway
The Year of Magical Thinking by Joan Didion
Hemingway by Ken Burns & Lynn Novick
War and Peace by Leo Tolstoy
All The Light You Cannot See by Anthony Doerr
Garmin watch

Chapters

00:00 Intro
0:34 Can You Make Money As A Writer?
2:23 Should You Become An Author?
3:25 Is Mark More of An Author or an Entrepreneur?
4:40 Mark’s Journey to Wealth
7:04 Wealth’s Impact on Life and Relationships
12:10 Achieving Your Dreams Isn’t As Great As It Seems
15:17 Is Mark Done With Money?
16:42 Mark’s New Aspirations
18:31 Fame’s Impact on Mark’s Life
18:54 Mark’s Team
20:10 Mark on Managing His Team
21:23 Are Books Still Relevant Today?
23:12 Protecting Mental Health While Working in Social Media
24:16 The Advantages of Social Media
26:03 Mark’s Experience Making A Film
30:13 The Creator Economy is the Future
30:51 What Mark’s Does With His Money
31:46 Changing Social Circles & Finance Bros
36:55 Writers & Books Mark Loves
39:57 Mark’s Current Source of Stress
41:23 Mark’s Favorite Products
42:56 Mark’s Role Models
43:38 What Mark’s Excited About


🔗 Connect with Mark:

Twitter: @IAmMarkManson
Instagram: @markmanson
LinkedIn: @markmanson
Tiktok: @IAmMarkManson
Youtube: @IAmMarkManson
Website: https://markmanson.net

🔗 Connect with Andrew:

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

In world where we’re constantly encouraged to want more, how do you find the courage to say no?

Founder and CEO of 37signals (makers of Basecamp, HEY, and ONCE) Jason Fried joins the podcast for a wide-ranging conversation covering software products and services, saying ‘no’ to millions, learning drums, and more. Jason shares his unique perspectives on building and running a hugely successful software company while staying true to his values.

Join us as we explore Jason's story and learn about:

• The motivation behind Basecamp's recent expansion into new products like email and calendar apps
• How Jason and his co-founder have structured the company to maximize independence and avoid things they don't want to do
• Thoughts on wealth and what he plans to do with the financial success of Basecamp
• Current interests and passions outside of work, and what he would do if he couldn't run Basecamp anymore
• Books and favorite products

Whether you're a tech entrepreneur or simply fascinated by the career of one of the industry's most unconventional and opinionated leaders, Jason's experiences and philosophies are sure to challenge and inspire you. Tune in for an honest and spontaneous discussion touching on the deepest questions in life and business.

Resources Mentioned

• Drumeo
• Decent Espresso Machine
• 1978 Porsche 928
• Books: The Old Man and the Sea, The Overstory, Rabbit is Rich
• Hey Calendar
• Once
• Campfire

‍

Chapters

00:00 - Introduction
2:20 - Inspiration Behind Hey Calendar
3:47 - Fantastical vs. Hey Calendar
4:55 - What Keeps Jason Going
7:24 - Why Hey Calendar Caps at $99
9:09 - Jason’s Commitment to Independence
12:59 - Limits to Improvement and Acceptance
15:56 - Jason’s Plans on Growing His Business
19:12 - Learning to Trust CEO Hires
20:59 - Why Jason Decided to Build New Products After 10 Years
24:21 - Changing Your Mind & Balancing Growth and Maintenance
28:06 - Keeping Businesses Simple
32:20 - What Jason Does With His Money
36:28 - The Courage to Close A Business
39:42 - The Burden of Wealth: Philanthropy and Responsibility
42:43 - Finding Joy in Spaces and Experiences
45:11 - Alternate Career Paths Jason is Drawn To
48:01 - The Future and Existential Worries
52:56 - Growing Old, the Younger Generation, and Life
59:27 - Things Jason Has Been Loving Lately
62:49 - Embracing Fiction: The Power of Storytelling

🔗 Connect with Jason:

Twitter/X: @jasonfried
LinkedIn: @jason-fried
37signals: https://37signals.com/

🔗 Connect with Andrew:

Twitter/X: @awilkinson (exclusive monthly AMAs for subscribers)
LinkedIn: @awilkinson
Website: https://www.neverenough.com/
Sign up for Andrew's weekly newsletter

Marshall Haas is the Co-founder of Shepherd (now Somewhere), who recently sold a majority stake in his company. Watch as we dive into the incredible journey from architecture to headhunting, leading to a million-dollar exit.

Marshall offers valuable insights from his diverse ventures, including selling iPhone cases, running an Airbnb business, and building Shepherd. He discusses the challenges of growing a company, working with influential partners, and the emotional aspects of selling a business.

Chapters
00:45 - Introducing Marshall Haas: From Architecture to Entrepreneurship
00:57 - Entrepreneurship Journey: First Businesses to E-Commerce Success
03:51 - Diving into Real Estate: The Airbnb Experiment
04:57 - Headhunting and Starting Shepherd
10:11 - Selling Shepherd Behind The Scenes
15:50 - What’s Next?
20:29 - Building a New Home
22:03 - Life After the Big Deal
23:49 - Finding Purpose Beyond Wealth
24:34 - Exploring Hobbies and Building New Connections
27:09 - The Power of Time Tracking and Delegation
28:39 - Books That Shape a Business Mindset
32:40 - Innovative Health and Productivity Hacks
33:36 - The Joy of Delegating Leadership
35:15 - Business Ideas and Future Ventures
41:10 - Essential Tools for Productivity and Creativity
42:37 - Exploring New Career Paths

🔗 Connect with Marshall:
Twitter/X: https://twitter.com/marshal
Instagram: https://www.instagram.com/marshallhaas/
Website: https://www.needwant.com
Website: https://www.somewhere.com/

🔗 Connect with Andrew:
Twitter/X: https://twitter.com/awilkinson (exclusive monthly AMAs for subscribers)
LinkedIn: https://www.linkedin.com/in/awilkinson/
Website: https://www.neverenough.com/
Weekly recommendations: https://bit.ly/4bT6IRv

Andrew sits down with Sam Parr, a serial entrepreneur known for his successful ventures like The Hustle and the My First Million podcast. Sam shares his unconventional journey, starting from his humble beginnings with a hotdog stand and moving on to building thriving businesses. He opens up about the lessons he's learned along the way, mistakes he has made, the importance of surrounding yourself with industry disruptors, and his latest focus on his latest venture Hampton, an exclusive community of high-growth founders.

Chapters
01:03 Sam's entrepreneurial journey and background
03:37 The psychology of success and motivation
04:34 Innovative approaches to leadership and delegation
19:53 Navigating fame, friendship, and trust as an entrepreneur
24:48 Personal transformation through fitness and self-improvement
27:09 The importance of routine and support systems
27:26 Overcoming mental health challenges
28:22 Inspirational figures and their impact
31:54 Productivity tips and daily routines
34:52 Mastering storytelling and continuous learning
42:53 Discovering game-changing products and habits
46:14 Fascinating people to follow and learn from


Follow Sam on:
Twitter/X: @thesamparr
Website: https://www.Joinhampton.com
Podcast: https://www.mfmpod.com

Follow Andrew on:
Twitter/X: @awilkinson