Never Enough

Andrew Wilkinson

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.

  • 1 hour 10 minutes
    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

    4 October 2024, 6:00 pm
  • 49 minutes 15 seconds
    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

    3 September 2024, 7:00 pm
  • 1 hour 27 minutes
    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


    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

    9 August 2024, 6:00 pm
  • 47 minutes 55 seconds
    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

    12 July 2024, 2:00 pm
  • 1 hour 8 minutes
    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

    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

    31 May 2024, 5:00 pm
  • 47 minutes 39 seconds
    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

    22 May 2024, 10:00 am
  • 50 minutes 49 seconds
    From Hot Dog Stand to Millions: The Untold Story of Sam Parr

    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

    27 March 2024, 4:00 pm
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