Never Enough

About the episodeIn 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 over1. 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 textAnd so much more. Resources Mentioned- Readwise - Superwhisper- EightSleep- Lomi: Smart Waste Kitchen Composter- Text - Things- Reclaim AI- Basecamp- Fathom- ClayChapters00:00 Intro00:33 Getting to Know Charlie3:17 Charlie’s Typical Day5:15 Charlie’s Journaling Routine11:56 Charlie’s Library of Journaling Questions13:48  Facilitating Deep Work15:39 Dealing With Low Priority Tasks20:09 Avoiding Distraction While in Deep Work21:19 Time spent in Deep Work21:47 Charlie’s Favorite Type of Deep Work23:19 Meeting Recordings, Transcripts, & CRMs26:48 Charlie’s System for Reading31:35 Keeping Track of Interesting Podcast Tidbits34:22 Dealing With AI’s Recency Bias35:57 How Charlie Keeps Consistent With His System38:11 What Drives Charlie to Create Systems42:18 Broken Parts of Charlie’s System44:00 What Charlie’s Looking Forward to With AI45:55 Other Interesting Ways Charlie Uses AI49:30 Products Charlie Really Loves🔗 Find Charlie On:LinkedIn: @charliegrinnell Twitter/X: @CharlieGrinnell Instagram: @charliegrinnell🔗 Find Andrew on:Twitter/X: @awilkinsonLinkedIn: @awilkinsonWebsite: https://www.neverenough.com/Sign up for Andrew's newsletter

About the episodeIn 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. Chapters00:00 - Intro00:19 - Useful Not True03:35 - How Derek Comes Up With Book Topics07:35 - Spending the Past 15 Years Exploring12:06 - Optimizing for Personal Growth14:52 - Burning Ships20:27 - Negative Impacts of Wealth22:14 - The Burden of Philanthropy26:17 - A Day in Derek’s Life28:53 - Is Derek Introverted?30:12 - Derek’s Hard No’s35:35 - Derek’s Nomadic Blood38:01 - Derek’s Fame42:38 - Derek’s Thoughts on AI57:12 - Overcoming Prejudices59:25 - Doing What Scares You1:01:54 - Learning to Appreciate China1:06:48 - Closing🔗 Find Derek on:Website: https://sive.rs/His Now Page: https://sive.rs/nowHis Latest Book: https://sive.rs/u🔗 Find Andrew on:Twitter/X: @awilkinsonLinkedIn: @awilkinsonWebsite: https://www.neverenough.com/Sign up for Andrew's newsletter

About the EpisodeCan 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 exploreCodie’s journey from working in Vanguard to owning multiple businesses of her ownThe appeal of boring businessesStrategies to help you know whether the businesses you want to buy or start are actually any goodAI and technology’s impact on businesses and the job marketCodie’s perspective on fame, navigating challenges, and her aspirationsPeople and products that she’s been loving latelyMaybe 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 MentionedBalajiJonah GoldbergAyman Al-AbdullahResources MentionedMain Street Millionaire by Codie SanchezThe Triumph of William McKinley by Karl RoveThe Vietnam War by Ken Burns & Lynn NovickBach flower remedyLogitech Casa Pop-Up DeskChapters00:00 - Intro00:42 - Catching Up With Codie5:01 - Codie’s Entrepreneurial Journey8:51 - Why Boring Businesses Are Great13:23 - What Businesses Do You Buy?16:07 - How to Tell If Your Businesses Ideas Are Good18:37 - Weird But Profitable Businesses21:24 - Businesses AI Will Disrupt23:33 - Integrating Tech In Businesses25:15 - White Collar Workers Shifting to Blue Collar Jobs30:57 - Fame’s Impact on Codie’s Life36:00 - Codie’s Goals For the Future37:51 - Dealing Tough Days41:53 - Codie’s Book43:48 - Codie’s Product Recommendations47:38 - People Codie Finds Interesting🔗 Find Codie on:Twitter/X: @Codie_SanchezInstagram: @codiesanchezTiktok: @realcodiesanchezYoutube: @CodieSanchezCTWebsite: https://www.codiesanchez.com/🔗 Find Andrew on:Twitter/X: @awilkinsonLinkedIn: @awilkinsonWebsite: 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 exploreNick’s journey from trying to start a software company in India, moving to NYC and building Museum Hack, to where he is nowThe art of active hosting and how to use it to meet interesting, new peopleDealing with rejected invitations and importance of providing value to the people you meetHis passion for adventure, along with tips for aspiring travelersThe little things that Nick splurges on and uses everydayIf 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 MentionedThe 2-Hour Cocktail Party by Nick GrayStoryworthy by Matthew DicksBuckwheat pillowWeighted blanketTrelloUpworkChapters00:00 - Preview00:50 - Mateina Yerba Mate2:56 - How Andrew First Met Nick5:08 - Nick’s Newsletter6:01 - Starting a Software Company in India to Living in NYC9:30 - Museum Hack11:33 - Benefits of Having A Newsletter14:25 - The 2-Hour Cocktail Party & Active Hosting19:25 - The N.I.C.K. Method23:03 - Prioritizing Adventure Over Money24:34 - Growing Social Circles Through Hosting28:33 - Nick’s Friendship Funnel37:55 - Tips for Hosting41:00 - Rejection With Invites43:23 - Nick’s Favorite Hosts44:28 - Adding Value to People You Meet54:34 - Balancing Adventure With Routine59:11 - Finding Interesting Experiences1:03:01 - Nick’s Views on Travel1:05:22 - Nick’s Blind Date in Tokyo1:09:10 - Nick’s Investments1:11:02 - How Nick Enjoys His Money1:18:15 - Nick’s Daily Routine1:22:43 - Nick’s Productivity System🔗 Connect with Andrew:Twitter/X: @awilkinsonLinkedIn: @awilkinsonWebsite: https://www.neverenough.com/Sign up for Andrew's newsletter🔗 Connect with Nick:Twitter: @NickGrayNewsInstagram: @nickgraynewsLinkedIn: @nickgraynewsYoutube: @nickgrayWebsite: 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 industryLiterature’s place in current societyHollywood’s inefficiency and the future of the creator economyThe impact that fame and wealth has on people and relationshipsMark’s current struggles as well as what he’s looking forward to in the futureCraving 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 MentionedThe Subtle Art of Not Giving A F*ck by Mark MansonOld Man in The Sea by Ernest HemingwayThe Year of Magical Thinking by Joan DidionHemingway by Ken Burns & Lynn NovickWar and Peace by Leo TolstoyAll The Light You Cannot See by Anthony DoerrGarmin watchChapters00:00 Intro0:34 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 Wealth7:04 Wealth’s Impact on Life and Relationships12:10 Achieving Your Dreams Isn’t As Great As It Seems15:17 Is Mark Done With Money?16:42 Mark’s New Aspirations18:31 Fame’s Impact on Mark’s Life18:54 Mark’s Team20:10 Mark on Managing His Team21:23 Are Books Still Relevant Today?23:12 Protecting Mental Health While Working in Social Media24:16 The Advantages of Social Media26:03 Mark’s Experience Making A Film30:13 The Creator Economy is the Future30:51 What Mark’s Does With His Money31:46 Changing Social Circles & Finance Bros36:55 Writers & Books Mark Loves39:57 Mark’s Current Source of Stress41:23 Mark’s Favorite Products42:56 Mark’s Role Models43:38 What Mark’s Excited About🔗 Connect with Mark:Twitter: @IAmMarkManson Instagram: @markmansonLinkedIn: @markmanson Tiktok: @IAmMarkManson Youtube: @IAmMarkManson  Website: https://markmanson.net🔗 Connect with Andrew:Twitter/X: @awilkinsonLinkedIn: @awilkinsonWebsite: 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 appsHow Jason and his co-founder have structured the company to maximize independence and avoid things they don't want to doThoughts on wealth and what he plans to do with the financial success of BasecampCurrent interests and passions outside of work, and what he would do if he couldn't run Basecamp anymoreBooks and favorite productsWhether 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 MentionedDrumeoDecent Espresso Machine1978 Porsche 928Books: The Old Man and the Sea, The Overstory, Rabbit is RichHey CalendarOnceCampfire‍Chapters00:00 - Introduction2:20 - Inspiration Behind Hey Calendar3:47 - Fantastical vs. Hey Calendar4:55 - What Keeps Jason Going7:24 - Why Hey Calendar Caps at $999:09 - Jason’s Commitment to Independence12:59 - Limits to Improvement and Acceptance15:56 - Jason’s Plans on Growing His Business19:12 - Learning to Trust CEO Hires20:59 - Why Jason Decided to Build New Products After 10 Years24:21 - Changing Your Mind & Balancing Growth and Maintenance28:06 - Keeping Businesses Simple32:20 - What Jason Does With His Money36:28 - The Courage to Close A Business39:42 - The Burden of Wealth: Philanthropy and Responsibility42:43 - Finding Joy in Spaces and Experiences45:11 - Alternate Career Paths Jason is Drawn To48:01 - The Future and Existential Worries52:56 - Growing Old, the Younger Generation, and Life59:27 - Things Jason Has Been Loving Lately62:49 - Embracing Fiction: The Power of Storytelling🔗 Connect with Jason:Twitter/X: @jasonfriedLinkedIn: @jason-fried37signals: https://37signals.com/ 🔗 Connect with Andrew:Twitter/X: @awilkinson (exclusive monthly AMAs for subscribers)LinkedIn: @awilkinsonWebsite: 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.Chapters01:03 Sam's entrepreneurial journey and background03:37 The psychology of success and motivation04:34 Innovative approaches to leadership and delegation19:53 Navigating fame, friendship, and trust as an entrepreneur24:48 Personal transformation through fitness and self-improvement27:09 The importance of routine and support systems27:26 Overcoming mental health challenges28:22 Inspirational figures and their impact31:54 Productivity tips and daily routines34:52 Mastering storytelling and continuous learning42:53 Discovering game-changing products and habits46:14 Fascinating people to follow and learn fromFollow Sam on:Twitter/X: @thesamparrWebsite: https://www.Joinhampton.comPodcast: https://www.mfmpod.comFollow Andrew on:Twitter/X: @awilkinson