The Compound and Friends
The Compound and Friends

How to Play the Money Game with Michael Santoli

August 21, 2026

AI Summary

5 min read

How to Play the Money Game with Michael Santoli

Michael Santoli, CNBC's senior markets commentator and co-anchor of Closing Bell: Overtime, has spent three decades covering financial markets without ever wanting to trade. "I don't have the gambling thing," he says. This temperamental distance from the action—combined with a historian's instinct for pattern recognition and a writer's need to explain—has made him one of the most trusted voices in financial journalism. In this conversation with Josh Brown and Michael Batnick, Santoli traces the psychology of markets, the mechanics of modern trading, and the enduring lessons that separate useful observation from noise.

The Demand for Prediction

One of Santoli's most revealing anecdotes involves a financial advisor he called "Mystery Broker" at Barron's. In late 2009, this anonymous source wrote to say the financial crisis was over and investors should treat it as a new bull market. Santoli mentioned the letter in a column without naming the source, and readers became obsessed. They demanded updates, speculated about the broker's identity, and assumed he possessed secret knowledge.

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What you'll learn

  • 1 (03:12) **The Observer’s Temperament** - Santoli explains why he never wanted to be a trader despite covering markets for decades.
  • 2 (10:38) **The Myth of the Market Guru** - The hosts discuss why people desperately believe someone can predict the market, using the “Mystery Broker” story as proof.
  • 3 (29:48) **Why Trump Thinks Like a Borrower** - The group dissects a 1989 video of Donald Trump complaining that good economic news raises interest rates.
  • 4 (38:03) **Why the Stock Market Is Surprisingly Strong** - Santoli explains the resilience of equities despite high rates, wars, and a cooling AI trade.
  • 5 (41:10) **The Immaculate Rotation** - Santoli describes how the market now moves in mechanical, programmatic rotations rather than on news.
  • 6 (49:42) **Retail Traders: Smart Money or Noise?** - The group debates whether the rise of retail investors is a stabilizing force or a dangerous trend.
  • 7 (52:12) **The Rise of Defined-Outcome Investing** - Brown and Santoli discuss why options-based ETFs (like those selling covered calls) have exploded in popularity.

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Guests on this episode

Show Notes

On episode 256 of The Compound and Friends, ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Downtown Josh Brown⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and Michael Batnick are joined by⁠ Michael Santoli ⁠ to discuss: the surprising strength of the stock market, what’s keeping the bull market alive, interest rates and the growing U.S. debt load, why corporate earnings remain so powerful, and whether today’s valuations can keep climbing. They also get into AI spending and the return on massive tech capex, market breadth and rotation, the rise of retail investors, options-income ETFs, why bears keep moving the goalposts, and what decades of market history can teach investors about adapting when the old rules stop working.


This episode is sponsored by DBMF and Vanguard.


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Investing involves the risk of loss. This podcast is for informational purposes only and should not be or regarded as personalized investment advice or relied upon for investment decisions. Michael Batnick and Josh Brown are employees of Ritholtz Wealth Management and may maintain positions in the securities discussed in this video. All opinions expressed by them are solely their own opinion and do not reflect the opinion of Ritholtz Wealth Management.


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