TIP540: Lessons in Life and Business from a Self-Made Billionaire w/ Andrew Wilkinson

TIP540: Lessons in Life and Business from a Self-Made Billionaire w/ Andrew Wilkinson

Trey chats with billionaire entrepreneur and investor, Mr. Andrew Wilkinson. They discuss various topics, including self-care and parenting, as well as exciting deals he collaborated on with Bill Ackman and Howard Marks. Andrew is the co-founder of Tiny, which has been called the Berkshire Hathaway of Tech companies. Andrew turned his first business, MetaLab, into a not-so-tiny conglomerate in a similar fashion to how Buffett turned an old textile mill into the juggernaut Berkshire is today. IN THIS EPISODE, YOU'LL LEARN: 0:00 - Intro 04:50 - The philosophies behind Tiny and how it operates. 10:49 - How he partnered up with Bill Ackman and Howard Marks on some exciting deals. 30:07 - Andrew’s insights from his conversations with Warren Buffett and Charlie Munger. 35:56 - What it means to set “Anti-goals”. 54:03 - The art and science of self care, de-stressing and delegation. 59:00 - Andrew’s thoughts on parenting, philanthropy, entrepreneurship, investing and a TON of amazing resources. Disclaimer: Slight discrepancies in the timestamps may occur due to podcast platform differences. BOOKS AND RESOURCES Join the exclusive TIP Mastermind Community to engage in meaningful stock investing discussions with Stig, Clay, and the other community members. How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets by Felix Dennis. Khan Academy Website. The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It by Michael E. Gerber. The Dhandho Investor: The Low-Risk Value Method to High Returns by Mohnish Pabrai. Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway's Vice Chairman on Life, Business, and the Pursuit of Wealth with Commentary by David Clark. Influence, New and Expanded: The Psychology of Persuasion by Robert B. Cialdini. The Psychology of Human Misjudgment by Charlie Munger Audiobook. Tiny Website. Trey Lockerbie's Twitter. Andrew Wilkinson's Twitter. NEW TO THE SHOW? Check out our We Study Billionaires Starter Packs. Browse through all our episodes (complete with transcripts) here. Try our tool for picking stock winners and managing our portfolios: TIP Finance Tool. Enjoy exclusive perks from our favorite Apps and Services. Stay up-to-date on financial markets and investing strategies through our daily newsletter, We Study Markets. Learn how to better start, manage, and grow your business with the best business podcasts. SPONSORS Support our free podcast by supporting our sponsors: River Toyota Sun Life The Bitcoin Way Range Rover Sound Advisory BAM Capital Fidelity SimpleMining Briggs & Riley Public Shopify Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm Learn more about your ad choices. Visit megaphone.fm/adchoices Support our show by becoming a premium member! https://theinvestorspodcastnetwork.supportingcast.fm

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Programming Update Regarding Bitcoin Fundamentals and Infinite Tech

Programming Update Regarding Bitcoin Fundamentals and Infinite Tech

We will temporarily pause new episodes of both shows. In the meantime, we encourage you to check out our other shows in this feed, including The Investor's Podcast and Richer, Wiser, Happier. Thank ...

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RWH066: Essential Truths w/ Howard Marks, Nima Shayegh & William Green

RWH066: Essential Truths w/ Howard Marks, Nima Shayegh & William Green

William Green highlights essential truths about investing, business & life that emerged from two of his favorite interviews with Howard Marks and Nima Shayegh. This episode also explores powerful less...

22 Feb 1h 30min

TIP793: Thinking Fast & Slow by Daniel Kahneman w/ Clay Finck

TIP793: Thinking Fast & Slow by Daniel Kahneman w/ Clay Finck

Clay explores Daniel Kahneman’s book Thinking, Fast and Slow, unpacking the cognitive biases that quietly shape our investment decisions. While markets often appear to be driven by data and logic, our...

20 Feb 1h

TECH015: OpenClaw and Self-Sovereign AI w/ Alex Gladstein and Justin Moon (Tech Podcast)

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Alex Gladstein and Justin Moon break down the fundamentals of large language models and explore the rise of OpenClaw as a self-sovereign AI assistant. Justin explains context engineering, local infe...

18 Feb 1h 4min

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

TIP792: Vital Lessons From History’s Strangest Financial Stories w/ Kyle Grieve

Kyle Grieve discusses how a series of unforgettable real-world stories reveal the hidden psychological traps that derail investors. IN THIS EPISODE YOU’LL LEARN: 00:00:00 - Intro 00:03:07 - How Ro...

15 Feb 1h 8min

TIP791: Best Quality Stock Idea Q1 2026 w/ Clay Finck

TIP791: Best Quality Stock Idea Q1 2026 w/ Clay Finck

Clay breaks down his best quality stock idea for Q1 2026: Visa. Visa is a global payments network that operates as a toll booth on commerce. Visa is one of the most durable and capital-light business...

13 Feb 1h

BTC259: Bitcoin & Theoretical Physics w/ Jeff Booth, Jack & Nick (Bitcoin Podcast)

BTC259: Bitcoin & Theoretical Physics w/ Jeff Booth, Jack & Nick (Bitcoin Podcast)

Jeff Booth, Jack, and Nick explore a year-long paper linking Bitcoin to fundamental physics, framing Bitcoin blocks as discrete, quantized units of time. They connect concepts from quantum mechanics a...

11 Feb 1h 16min

TIP790: Wealth Beyond Money w/ Thomas Mueller-Borja

TIP790: Wealth Beyond Money w/ Thomas Mueller-Borja

In this episode, Stig Brodersen speaks with Thomas Mueller-Borja, the Global Co-Head of Real Estate and Global CIO for Value-Add Real Estate at BlackRock. They explore how great investors define games...

8 Feb 1h 19min

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