Never Enough

Hosted by Andrew Wilkinson

Business Entrepreneurship Technology

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Latest episode

May 2025

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EN-US

About the show

I talk to interesting people for a living. You get their cheat codes. Join me as I go deep on what they do, how they do it, and the messy realities of success.

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11 recent

May 18, 202540 min

Hacks: Productivity, AI, and Minimalism with Sam Corcos

In this episode, Andrews chats with Sam Corcos, founder of Levels. Sam, a software developer, shares his unique systems for productivity, time management, and life hacks. He delves into how he maximizes his time and energy while juggling work and family. We talk about: Time tracking & prioritization: Aligning your actions with your goals. Life transitions: How marriage and parenthood impact productivity. Minimizing distractions: Creating buffers and using alarms. Learning on the go: Audiobooks and AI for knowledge consumption. The future of work: AI in software development and the changing role of developers. Living intentionally: Minimalism, decision-making, and the benefits of co-living. Life hacks: Meal prepping, and more! Resources Mentioned: Mack's silicone earplugs Cotton blankets The Anxious Generation by Jonathan Haidt Notebook LM Replit Cursor Chapters: 00:00 Intro 0:56 Get to know Sam 1:47 Marriage and parenthood’s impact on productivity 4:21 Building systems to minimize distractions 6:43 Health hacks 8:51 Setting alarms for important events 10:58 Audiobooks & AI for learning 15:32 AI as coding tools 17:52 Sam’s thoughts on AI & jobs 27:10 Minimalism 30:51 Management in business 35:52 Co-living and raising kids 38:00 Meal prep 39:17 Closing Find Sam on: Linkedin Twitter/X Levels Follow Andrew: Twitter/X LinkedIn Get a copy of Never Enough Weekly recommendations

May 12, 20252 hr 34 min

How I Built a $180M/Year Business Without Making Myself Miserable

Wouter Teunissen cold emailed me and asked if I'd come on his podcast. I told him, sure, come to Victoria and interview me in person (thinking he's from Europe, there's no way he actually will). He did. And it turned out to be one of the best conversations I've had in ages. This episode is reposted from Wouter's podcast, Biography . Watch this if you want to: Design a business that serves your life (not the other way around) Learn how relationships are the highest ROI growth strategy Get tactical advice on productivity, decision-making, and purpose Hear how I turned burnout into a $180M portfolio—and found peace Chapters: 00:00 – Intro 01:52 – Using Money In Interesting Ways to Make Your Life Better 06:00 – Creating a Friendship Funnel for Exponential Growth 22:07 – Why Every Business Should Be a Lifestyle Business 30:52 – Why Andrew Decided to Become an Investor 42:21 – Auditing Your Life and Building Narratives as a Coping Mechanism 53:43 – Andrew’s Productivity Stack Using AI, Lists and Tools 1:15:54 – Why The Biggest Opportunity to Make Money is in Relationships 1:28:43 – The AI Revolution 1:49:07 – Andrew’s $100 Million Framework 2:16:53 – Philanthropy Follow: Wouter | https://x.com/WouterTeunissen Andrew | https://x.com/awilkinson Subscribe to Andrew's newsletter: https://neverenoughnewsletter.kit.com/signup

January 6, 20251 hr 15 min

From Bouncer to Starting a $100M Health Empire with Derek MPMD

About The Episode Eight years ago, Derek suffered a leg injury while working as a bouncer at a bar in downtown Vancouver. Unable to walk, he began writing articles on health and fitness online. Today, he runs one of the biggest YouTube channels for that niche, alongside three other successful businesses. In this episode, he discusses the importance of maintaining your audience’s trust while opening up the current struggles he faces as an entrepreneur. Join us while we talk about Derek’s journey from bouncer to content creator and entrepreneur. Calling out celebrities and his interview with Joe Rogan Entrepreneurs with false health claims Derek’s perspective on health, how that has evolved over time, and general advice Products and services that he has been loving Resources Mentioned Gorilla Mind Gorilla Energy Marek Health Intelligent Outlived by Peter Attia The Drive podcast by Peter Attia Eight Sleep Timer from Amazon Death Clock Chapters 00:00 Introduction: From Bouncer to Blogger 00:42 Daily Routine and Night Owl Lifestyle 03:18 Building a Business Empire 05:54 The Journey to Success 13:41 Transparency in the Fitness Industry 38:35 Navigating Fame and Public Perception 41:45 The Double-Edged Sword of Fame 42:38 Managing Wealth and Business Strategies 45:28 The Challenges of Product Development 47:19 Exploring Digital Products and Content Creation 49:39 Personal Enjoyment and Financial Management 52:25 Investment Strategies and Wealth Management 59:37 Productivity Hacks and Tools 59:51 Book and Product Recommendations 01:04:14 Sleep Optimization and Final Thoughts Follow Derek: Twitter/X Instagram YouTube Follow Andrew: Twitter/X LinkedIn Get a copy of Never Enough Weekly recommendations

November 11, 20241 hr 0 min

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 - Superwhispe r - 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

October 4, 20241 hr 10 min

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

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

September 3, 202449 min

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 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

August 9, 20241 hr 27 min

How to Become a Friend Billionaire with Nick Gray

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

July 12, 202447 min

From Party Boy to Millionaire Bestselling Author: Mark Manson on the Business of Books

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

May 31, 20241 hr 8 min

Building a Software Company and Saying 'No' to Millions with Jason Fried.

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

May 22, 2024Episode 247 min

From Architecture to Headhunting, A Million-Dollar Exit Story with Marshall Haas

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