Here are 12 books that Deep Risk fans have personally recommended if you like Deep Risk. Shepherd is a community of 12,000+ authors and super readers sharing their favorite books with the world.

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Book cover of The Ages of the Investor

Larry R. Frank Sr. Author Of Wealth Odyssey: The Essential Road Map for Your Financial Journey Where Is It You Are Really Trying to Go with Money?

From Larry's 3 favorite reads in 2025.

Why am I passionate about this?

Author Father Grandfather Business founder Planner and thinker Income and longevity researcher

Larry's 3 favorite reads in 2025

Larry R. Frank Sr. Why Larry loves this book

Recently retired, I re-read this series and felt insights I had the first time I read these. What are the many kinds of investment risks? Most people think of the risk of losing their money. William Bernstein dissects this simple view into many different shades of risk and astutely discusses that not all risks are of equal possibility. So while some may worry about a certain risk, they should also consider how possible that event to create the risk may be. Yes, markets go up and down all the time. But, that is not risk! The risk comes from how you react to markets.

The first booklet, “
The Ages of the Investor,” looks at the sequence of market returns.
– There are two different kinds of risk:

1) Savings Sequence Risk
– The sequence of returns does matter when investing periodically and does NOT matter with lump sums when…

By William J. Bernstein ,

Why should I read it?

1 author picked The Ages of the Investor as one of their favorite books, and they share why you should read it.

What is this book about?

"The Ages of the Investor: A Critical Look at Life-cycle Investing" is intended to be the first installment in the "Investing for Adults" series. Just as grown-ups do not believe in the Tooth Fairy, the Easter Bunny, or Santa Claus, “Investing adults” know that there is no such creature as the Stock-picking Fairy or the Market-timing Fairy. Further, there is no Risk Fairy who will write you cheap options that will protect your stock holdings against loss. Investing adults are familiar with Gene Fama, Zvi Bodie, Jack Bogle, and Burton Malkiel, and understand that a mean variance optimizer does not…


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Book cover of December on 5C4

December on 5C4 by Adam Strassberg,

Magical realism meets the magic of Christmas in this mix of Jewish, New Testament, and Santa stories–all reenacted in an urban psychiatric hospital!

On locked ward 5C4, Josh, a patient with many similarities to Jesus, is hospitalized concurrently with Nick, a patient with many similarities to Santa. The two argue…

Book cover of Skating Where the Puck Was

Larry R. Frank Sr. Author Of Wealth Odyssey: The Essential Road Map for Your Financial Journey Where Is It You Are Really Trying to Go with Money?

From Larry's 3 favorite reads in 2025.

Why am I passionate about this?

Author Father Grandfather Business founder Planner and thinker Income and longevity researcher

Larry's 3 favorite reads in 2025

Larry R. Frank Sr. Why Larry loves this book

William J Bernstein's second booklet in this series, “Skating Where the Puck Was,” looks at correlations.
– In a perfect world, investment options would be totally uncorrelated to each other. At one time in history, this was truer than it is today. With communications shrinking the world, events on one side of the globe quickly reverberate through the markets to the other side. The effect is to increase correlation.
– The effect is that strategies that used to work tend not to anymore due to correlations. And new strategies quickly fall on their faces when events turn their ugly head and bite.
– Bernstein ticks off many strategies falling on their faces due to the effect of strategies becoming more widely used.
– My main beef with the tone of this booklet is the focus on beating markets (which may be more to say what the strategies are about, then…

By William J. Bernstein ,

Why should I read it?

1 author picked Skating Where the Puck Was as one of their favorite books, and they share why you should read it.

What is this book about?

Skating Where the Puck Was: The Correlation Game in a Flat World is the second installment in the Investing for Adults series. This series is not for novices. This booklet explores the notion that, as a general rule, no magic policy rich in high-return/low-correlation alternative asset classes exists that will simultaneously preserve upside reward and protect against downside losses. And as long as I'm lowering your expectations, this booklet is most certainly not a blueprint for the “perfect portfolio.” You're an adult, after all, so you know that the future efficient frontier lies well beyond our ken; presumably you already…


Book cover of Reinventing the Bazaar: A Natural History of Markets

Steven K. Vogel Author Of Marketcraft: How Governments Make Markets Work

From my list on how markets really work.

Why am I passionate about this?

I first got interested in how markets really work when I wrote my Ph.D. dissertation on the “deregulation” movement in the United States, Western Europe, and Japan. I quickly discovered that deregulation never happened in the literal sense. In most cases, governments had to increase regulation to enhance market competition. They needed more rules to get “freer” markets. This sounds paradoxical at first, but it really isn’t. It makes perfect sense once you realize that markets do not arise spontaneously but rather are crafted by the very visible hand of the government. So I took that insight and I have been running with it ever since.

Steven's book list on how markets really work

Steven K. Vogel Why Steven loves this book

McMillan offers a highly readable and concise book on how economists understand market institutions.

I love to assign this book to my undergraduate students because McMillan makes sense of some fairly complex topics, such as auction design. And he covers a wide range of topics of current interest, such as corporate governance and intellectual property rights.

By John McMillan ,

Why should I read it?

2 authors picked Reinventing the Bazaar as one of their favorite books, and they share why you should read it.

What is this book about?

From the wild swings of the stock market to the online auctions of eBay to the unexpected twists of the world's post-Communist economies, markets have suddenly become quite visible. We now have occasion to ask, "What makes these institutions work? How important are they? How can we improve them?"

Taking us on a lively tour of a world we once took for granted, John McMillan offers examples ranging from a camel trading fair in India to the $20 million per day Aalsmeer flower market in the Netherlands to the global trade in AIDS drugs. Eschewing ideology, he shows us that…


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Book cover of Trusting Her Duke

Trusting Her Duke by Arietta Richmond,

A Duke with rigid opinions, a Lady whose beliefs conflict with his, a long disputed parcel of land, a conniving neighbour, a desperate collaboration, a failure of trust, a love found despite it all.

Alexander Cavendish, Duke of Ravensworth, returned from war to find that his father and brother had…

Book cover of The Strategy of Conflict

Avinash Dixit Author Of The Art of Strategy: A Game Theorist's Guide to Success in Business and Life

From my list on economics and game theory.

Why am I passionate about this?

Avinash Dixit is an emeritus university professor of economics at Princeton. He is a member of the National Academy of Sciences and was President of the American Economic Association for the year 2008.

Avinash's book list on economics and game theory

Avinash Dixit Why Avinash loves this book

This is the book that brought game theory to life. Eschewing dry mathematical theorems, and conducting rigorous logical analysis through rich examples of strategic use of threats, promises, and brinkmanship in real life, Schelling opened up a whole world of practical applications of the theory. My own thinking and writing about game theory owes a huge debt to Schelling. You should also read his “Arms and Influence,” “Micromotives and Macrobehavior,” and “Choice and Consequence.”

By Thomas C. Schelling ,

Why should I read it?

1 author picked The Strategy of Conflict as one of their favorite books, and they share why you should read it.

What is this book about?

A series of closely interrelated essays on game theory, this book deals with an area in which progress has been least satisfactory-the situations where there is a common interest as well as conflict between adversaries: negotiations, war and threats of war, criminal deterrence, extortion, tacit bargaining. It proposes enlightening similarities between, for instance, maneuvering in limited war and in a traffic jam; deterring the Russians and one's own children; the modern strategy of terror and the ancient institution of hostages.


Book cover of A Splendid Exchange: How Trade Shaped the World

Avinash Dixit Author Of The Art of Strategy: A Game Theorist's Guide to Success in Business and Life

From my list on economics and game theory.

Why am I passionate about this?

Avinash Dixit is an emeritus university professor of economics at Princeton. He is a member of the National Academy of Sciences and was President of the American Economic Association for the year 2008.

Avinash's book list on economics and game theory

Avinash Dixit Why Avinash loves this book

A brilliant sweep through the millennia of commerce around the world. If you think globalization happened over the last quarter-century, you are wrong by about 5000 years. Find out how and why.

By William J. Bernstein ,

Why should I read it?

1 author picked A Splendid Exchange as one of their favorite books, and they share why you should read it.

What is this book about?

A sweeping narrative history of world trade—from Sumer in 3000 BC to the firestorm over globalization today—that brilliantly explores trade’s colorful and contentious past and provides fresh insights into social, political, cultural, and economic history, as well as a timely assessment of trade’s future.

Adam Smith wrote that man has an intrinsic “propensity to truck, barter, and exchange one thing for another.” But how did trade evolve to the point where we don’t think twice about biting into an apple from the other side of the world?

In A Splendid Exchange, William J. Bernstein tells the extraordinary story of global…


Book cover of Freakonomics: A Rogue Economist Explores the Hidden Side of Everything

Martin Sternstein Author Of Barron's AP Statistics

From my list on statistical insights into social issues.

Why am I passionate about this?

I taught for 45 years at Ithaca College broken by two years as Fulbright Professor in West Africa at the University of Liberia. During my years in academia, I developed several new courses including a popular “Math in Africa” class and the first U.S. course for college credit in chess theory. I’ve always had a passion for and continue to have strong interests in (1) national educational and social issues concerning equal access to math education for all and (2) teaching others about the power of mathematics and statistics to help one more deeply understand social issues.

Martin's book list on statistical insights into social issues

Martin Sternstein Why Martin loves this book

Steven Levitt, Professor of Economics at the University of Chicago, has written a thoughtful book at the layperson level to help one understand how mathematical and economic tools provide insights into sensitive social issues from racism to abortion.

He delves into predicting the long-term consequences of short-term decisions. This book is not intended for the college classroom, and it is controversial, but I found it to be a fascinating read.

By Steven D. Levitt , Stephen J. Dubner ,

Why should I read it?

7 authors picked Freakonomics as one of their favorite books, and they share why you should read it.

What is this book about?

The legendary bestseller that made millions look at the world in a radically different way returns in a new edition, now including an exclusive discussion between the authors and bestselling professor of psychology Angela Duckworth.

Which is more dangerous, a gun or a swimming pool? Which should be feared more: snakes or french fries? Why do sumo wrestlers cheat? In this groundbreaking book, leading economist Steven Levitt—Professor of Economics at the University of Chicago and winner of the American Economic Association’s John Bates Clark medal for the economist under 40 who has made the greatest contribution to the discipline—reveals that…


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Book cover of Aggressor

Aggressor by FX Holden,

It is April 1st, 2038. Day 60 of China's blockade of the rebel island of Taiwan.

The US government has agreed to provide Taiwan with a weapons system so advanced that it can disrupt the balance of power in the region. But what pilot would be crazy enough to run…

Book cover of Where Are the Customers' Yachts? Or a Good Hard Look at Wall Street

Victor Haghani Author Of The Missing Billionaires: A Guide to Better Financial Decisions

From my list on intelligent financial decision-making in less than 200 pages.

Why am I passionate about this?

I have over four decades of experience working and innovating in the financial markets and have been a prolific contributor to academic and practitioner finance literature. I started my career at Salomon Brothers in 1984, where I became a managing director in the bond-arbitrage group, and in 1993 I was a co-founding partner of the hedge fund Long-Term Capital Management. I founded Elm Wealth in 2011 to help clients, including my own family, manage and preserve their wealth with a thoughtful, research-based, and cost-effective approach that covers not just investment management but also broader decisions about wealth and finances.

Victor's book list on intelligent financial decision-making in less than 200 pages

Victor Haghani Why Victor loves this book

I loved this timeless classic. This book gets down to the essence of how to safely navigate Wall Street, where everyone wants a slice of your financial pie. It’s a quick and hilarious read that challenges the conventional investment wisdom that Wall Street tries to get you to believe.

You’ll become a more savvy and skeptical investor and avoid costly mistakes in your financial life. I gave a copy of this book to all my three children, and they loved it too!

By Fred Schwed ,

Why should I read it?

4 authors picked Where Are the Customers' Yachts? Or a Good Hard Look at Wall Street as one of their favorite books, and they share why you should read it.

What is this book about?

'Once I picked it up I did not put it down until I finished...What Schwed has done is capture fully-in deceptively clean language - the lunacy at the heart of the investment business' - From the Foreword by Michael Lewis, Bestselling author of "Liar's Poker". '...one of the funniest books ever written about Wall Street' - Jane Bryant Quinn, "The Washington Post". 'How great to have a reissue of a hilarious classic that proves the more things change the more they stay the same. Only the names have been changed to protect the innocent' - Michael Bloomberg. 'It's amazing how…


Book cover of A Random Walk Down Wall Street: The Time-Tested Strategy for Successful Investing

Eric Tyson Author Of Investing For Dummies

From my list on getting smarter about investing and money.

Why am I passionate about this?

When I was growing up, I saw family members and friends, who were otherwise smart people who could master other aspects of their lives, have difficulty with personal finance decisions and investing. When my dad was laid off during a recession, he had some retirement money distributed to him, and I got interested in investing as he researched and tried with difficulty to handle this money himself. In my young adult years, I was a sponge to learn as much as I could about personal finance. 

Eric's book list on getting smarter about investing and money

Eric Tyson Why Eric loves this book

I first read this book as required reading for a college course, and it greatly changed how I thought about investing.

Over the years, I’ve read updated editions, and it never gets stale and always includes new information and insights. But the foundational issues have stood the test of time and remain in the newest edition.

I also love this book because it introduced me at a young age to mutual funds and Vanguard.

By Burton G. Malkiel ,

Why should I read it?

8 authors picked A Random Walk Down Wall Street as one of their favorite books, and they share why you should read it.

What is this book about?

Today's stock market is not for the faint hearted. At a time of frightening volatility, the answer is to turn to Burton G. Malkiel's advice in his reassuring, authoritative, gimmick-free and perennially best-selling guide to investing. Long established as the first book to purchase before starting a portfolio, A Random Walk Down Wall Street now features new material on "tax-loss harvesting"; the current bitcoin bubble and automated investment advisers; as well as a brand-new chapter on factor investing and risk parity. And as always, Malkiel's core insights-on stocks and bonds, as well as investment trusts, home ownership and tangible assets…


Book cover of The Little Book of Common Sense Investing: The Only Way to Guarantee Your Fair Share of Stock Market Returns

Pim van Vliet Author Of High Returns from Low Risk

From my list on change the way you think about risk and return.

Why am I passionate about this?

I’ve spent my career studying the paradox that low-risk investing can lead to high returns. As an author and a multi-billion-dollar fund manager, I’ve seen firsthand how markets reward patience, discipline, and avoiding unnecessary risks. These books shaped my thinking—challenging conventional wisdom, deepening my understanding of risk, and reinforcing why defensive investing works. I love uncovering ideas that go against the grain, especially when they’re backed by data. Whether you’re an investor or just fascinated by how we make decisions under uncertainty, these books will change the way you see markets—and maybe even the way you invest.

Pim's book list on change the way you think about risk and return

Pim van Vliet Why Pim loves this book

Bogle’s philosophy is simple yet powerful: focus on the long term, keep costs low, and let compounding do the heavy lifting. I’ve always believed that great investing is about avoiding unnecessary risks and staying disciplined, and Bogle’s book distills that wisdom better than anyone else.

While I take a different approach than pure indexing, his principles of cost efficiency and long-term thinking are universal. Every investor—whether a stock picker or a passive indexer—should read this book at least once.

By John C. Bogle ,

Why should I read it?

7 authors picked The Little Book of Common Sense Investing as one of their favorite books, and they share why you should read it.

What is this book about?

The best-selling index investing "bible" offers new information and is updated to reflect the latest market data The Little Book of Common Sense Investing is the classic guide to getting smart about the market. Legendary mutual fund veteran John C. Bogle reveals his key to getting more out of investing: low-cost index funds. Bogle describes the simplest and most effective investment strategy for building wealth over the long term: buy and hold, at very low cost, a mutual fund that tracks the S&P 500 Stock Index. Such an index portfolio is the only investment that guarantees your fair share of…


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Book cover of The Duke's Christmas Redemption

The Duke's Christmas Redemption by Arietta Richmond,

A Duke who has rejected love, a Lady who dreams of a love match, an arranged marriage, a house full of secrets, a most unneighborly neighbor, a plot to destroy reputations, an unexpected love that redeems it all.

Lady Charlotte Wyndham, given in an arranged marriage to a man she…

Book cover of The Power of Passive Investing: More Wealth with Less Work

Russell Wild Author Of Bond Investing For Dummies

From my list on investing so that you profit, not your broker.

Why am I passionate about this?

I collected coins a kid. I went to college and studied econ. I worked in a bank. I later became a financial journalist. And later, a professional money manager. I’ve always been fascinated by money…the way it moves around the world, the enormous role it plays in peoples’ lives, the power it gives a select few, the good it can do, and the way it grows. As a fee-only financial planner running my own shop, I'm only peripherally involved with Wall Street. That frees me to step back and look at the key players, the shenanigans, the sometimes awful greed. The books I’ve selected were instrumental in helping others make their money work for them.

Russell's book list on investing so that you profit, not your broker

Russell Wild Why Russell loves this book

I’ve bumped into Richard “Rick” Ferri at a few financial conferences. He’s easy to recognize as the guy getting hate stares from across the room. Ferri thinks most financial professionals charge too much – way too much and he isn’t shy about saying so. One of the reasons he loves passive (index) investing, as I do, is that it can be done at very little cost. If you think you want to be an index investor, but you aren’t sure where to start, I highly recommend this book. It will serve as an excellent pair of training wheels, explaining the whys and the hows of proper index investing. I’d also love to see many financial professionals read it, for they’d become better money managers if they did. Yeah, I’m talking about those guys I see in the back of the room giving Ferri the evil eye!

By Richard A. Ferri ,

Why should I read it?

2 authors picked The Power of Passive Investing as one of their favorite books, and they share why you should read it.

What is this book about?

A practical guide to passive investing Time and again, individual investors discover, all too late, that actively picking stocks is a loser's game. The alternative lies with index funds. This passive form of investing allows you to participate in the markets relatively cheaply while prospering all the more because the money saved on investment expenses stays in your pocket. In his latest book, investment expert Richard Ferri shows you how easy and accessible index investing is. Along the way, he highlights how successful you can be by using this passive approach to allocate funds to stocks, bonds, and other prudent…


Book cover of The Ages of the Investor
Book cover of Skating Where the Puck Was
Book cover of Reinventing the Bazaar: A Natural History of Markets

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