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Barry Ritholtz: ‘How Not to Invest’

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Oct 7, 2025

Guest

Barry Ritholtz

Barry Ritholtz, co-founder and CIO of Ritholtz Wealth Management, dives into fascinating concepts around investing. He shares his shift from trading to long-term thinking, emphasizing behavioral economics. Ritholtz discusses the power of admitting uncertainty and challenges the allure of forecasts, pointing out their unreliability. He critiques the latte-factor mentality and advocates for using money to buy experiences instead. With insights on avoiding investment blunders and understanding market cycles, he offers innovative ways to rethink wealth management.

01:06:16

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Episode notes

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ANECDOTE

Memorable Ray Dalio Conversation

Barry recalled meeting Ray Dalio and later conducting what he felt was Dalio's best interview after Principles was public.
That conversation marked a turning point in Dalio's public persona and stayed with Barry as a standout podcast moment.

question_answer

ANECDOTE

Ken Feinberg's Heartbreaking Stewardship

Barry described interviewing Ken Feinberg about his role as special master after major disasters and how powerful those stories were.
He called Feinberg an American hero and said the episode was simultaneously heartbreaking and fascinating.

insights

INSIGHT

Avoid Errors Over Chasing Aces

Charlie Ellis taught Barry that investors win by avoiding mistakes rather than scoring big gains.
Focusing on preventing unforced errors beats chasing rare home-run investments for most people.

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From Trader to Long-Term Investor

01:57 • 2min

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How Barry Finds Time to Write and Publish

04:16 • 4min

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Why Barry Started Masters in Business Podcast

08:00 • 3min

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Memorable Podcast Conversations

11:00 • 4min

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Inversion and Avoiding Investment Mistakes

15:06 • 4min

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Why Forecasts Captivate Despite Being Unreliable

18:40 • 7min

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The Power of Saying 'I Don't Know'

26:01 • 3min

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Denominator Blindness and Misleading Numbers

Understanding Secular Market Cycles

32:38 • 6min

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Valuations: Pay Attention but Don't Time the Market

38:56 • 3min

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Why Politics Shouldn't Drive Investment Moves

41:46 • 3min

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How to Disconfirm Your Beliefs

44:53 • 4min

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Why Spending Advice and Consumption Scolding Mislead

48:47 • 9min

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Using Money to Buy Time and Meaningful Experiences

• Mentioned in 44 episodes

Four Thousand Weeks

Time Management for Mortals

Oliver Burkeman

In 'Four Thousand Weeks', Oliver Burkeman offers a contrarian approach to time management by focusing on the finite nature of human life. Assuming an average lifespan of 80 years, the book calculates that we have approximately 4,000 weeks to live. Burkeman argues against the modern fixation on productivity and efficiency, instead advocating for embracing the limits of time and prioritizing what truly matters. The book draws on insights from ancient and contemporary philosophers, psychologists, and spiritual teachers to help readers construct a more meaningful life by accepting and working within the constraints of time. It addresses issues such as the efficiency trap, the pitfalls of convenience culture, and the importance of living in the present while acknowledging the unpredictability of the future.

#44

• Mentioned in 178 episodes

Principles

Ray Dalio

In 'Principles: Life and Work', Ray Dalio shares the principles he has developed over his career that have helped him achieve success. The book is divided into three sections: the first section explains how Dalio's principles were formed from his personal and professional experiences; the second section outlines life principles, such as embracing reality, being radically open-minded, and understanding the importance of pain and reflection in personal growth; and the third section focuses on work principles, including the use of radical truth and radical transparency to transform an organization. Dalio advocates for systematizing decision-making into algorithms, learning from failures, and building a culture where it is okay to make mistakes but unacceptable not to learn from them.

#1535

• Mentioned in 19 episodes

Winning the loser's game

Timeless Strategies for Successful Investing

Charles D. Ellis

In 'Winning the Loser's Game,' Charles D. Ellis explains that investing has become a 'loser's game' where the outcome is determined by the mistakes of the loser, rather than the skills of the winner. Ellis advocates for a focus on developing and adhering to wise and appropriate investment policies, emphasizing the importance of understanding client needs, avoiding high fees, and investing for the long term. The book includes updated chapters on bond investing, investor behavior, and the impact of technology on investment decisions, while reinforcing core principles of successful investing such as indexing and reducing costs.

#6391

• Mentioned in 5 episodes

Bailout nation

How Greed and Easy Money Corrupted Wall Street and Shook the World Economy, with New Post-Crisis Update

Barry Ritholtz

#935

• Mentioned in 27 episodes

How Not to Invest

The ideas, numbers, and behavior that destroy wealth—and how to avoid them

Barry Ritholtz

#1772

• Mentioned in 17 episodes

Expert Political Judgment

How Good Is It? How Can We Know?

Philip E. Tetlock

In this book, Philip E. Tetlock evaluates the predictive abilities of experts by analyzing 27,451 verifiable predictions made by 284 world-renowned experts over more than 20 years. He finds that expert predictions are often no better than random guesses and identifies two types of thinkers: 'hedgehogs,' who are confident in their single, overarching idea, and 'foxes,' who are more eclectic and adaptable. Tetlock argues that foxes are generally more accurate in their predictions due to their ability to consider multiple perspectives and adapt to new information. The book also explores how the media often favors hedgehogs for their confident and decisive statements, despite their lower accuracy.

Today on the podcast, we’re welcoming Barry Ritholtz. He’s co-founder, chairman, and chief investment officer of Ritholtz Wealth Management, a firm that was launched in 2013. He’s the creator and host of Masters in Business, one of the earliest finance-related podcasts. He also regularly posts on The Big Picture, where he’s been covering everything investing related since 2003. He is the author of Bailout Nation, and his latest book, How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth—and How to Avoid Them, has just been published.

Background and Books

Barry Ritholtz LinkedIn

Ritholtz Wealth Management

Bailout Nation: How Greed and Easy Money Corrupted Wall Street and Shook the World Economy, with New Post-Crisis Update

How Not to Invest: The ideas, numbers, and behavior that destroy wealth—and how to avoid them

Podcasts and More

Masters in Business podcast

The Big Picture

“Masters in Business - Ray Dalio Full Show,” Masters in Business podcast, Nov. 30, 2018

“An Interview With Ken Feinberg: Masters in Business,” Masters in Business podcast, Oct. 9, 2015

“MiB: Charley Ellis on Rethinking Investing,” Masters in Business podcast, Feb. 21, 2025

“Why Fear Is an Investor’s Worst Enemy” by Samantha Lamas from the 2017 Morningstar ETF Conference, Morningstar.com, Sept. 12, 2017

“Rabbithole: What Do People Get Wrong About Money?” The Big Picture, March 10, 2025

“It’s Been 40 Years Since Our Cover Story Declared ‘The Death of Equities,’ ” by Peter Coy, Bloomberg, Aug. 13, 2019

Readings

Winning the Loser’s Game: Timeless Strategies for Successful Investing, Eighth Edition, by Charles D. Ellis

Expert Political Judgment: How Good Is It? How Can We Know?, by Philip E. Tetlock

Four Thousand Weeks: Time Management for Mortals, by Oliver Burkeman

Principles, by Ray Dalio

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