The $100M thought experiment: hobby bets

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In this Talking Shop episode, I sit down with Ashby Daniels for an unscripted, behind-the-scenes conversation about investing, markets, and the behavioral mistakes that quietly derail long-term results. We move freely—from why simplicity keeps winning, to how investors misread risk, to what actually matters when markets feel noisy—without a single hot take in sight. If you've ever wondered how two investment professionals talk when there's no agenda and no sales pitch, this is it.

Listen now and learn:

► Why "beating the game" in investing rarely looks like working harder or knowing more

► How narratives—not numbers—drive most investor mistakes during market downturns

► What gets misunderstood about bonds, diversification, and "playing it safe"

► How experienced investors think differently about wealth, risk, and time

Visit www.TheLongTermInvestor.com for show notes, free resources, and a place to submit questions.

[04:15] – Nick Murray's Lasting Influence on Long-Term Investing and Market Thinking

[05:45] – Why Investing Education Should Be Short, Simple, and Actionable

[08:00] – Challenging Conventional Market Wisdom: Why Time Beats Tactics

[09:45] – The Dave & Buster's Investing Lesson: How to "Beat the Game"

[15:30] – Everybody Ought to Be Rich: The Power of Long-Term Stock Market Returns

[18:30] – The Market Portfolio Explained: Stocks, Bonds, and Investor Distractions

[21:15] – Market Corrections and Bear Markets: Why Trees Don't Grow to the Sky

[24:30] – All-Stock Portfolios and Risk: When Equities Make Sense

[29:45] – Investor Panic Isn't About Volatility—It's About Stories and Expectations

[32:45] – Bond Investing, "Safety," and the Hidden Risk to Purchasing Power

[35:45] – Private Equity, Gold, and Crypto: What Investors Get Wrong

[41:30] – The $100 Million Thought Experiment: Getting Wealthy vs Staying Wealthy

[46:00] – Why Timeless Investing Principles Still Win Over Time

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