At 559 pages, On the Edge is a bear of a book, but strangely, I would not have wanted it shorter. Every page of this discursive book is chock-full of esoteric facts of interest to advisors, eloquently narrated by a world-class storyteller. Silver’s erudition is literally thrilling; the anecdotes involving names such as Elon Musk, Peter Thiel, Sam Bankman-Fried and Marc Andreeson are priceless. Nate Silver (The Signal and the Noise) founded the data-driven political platform Five Thirty-Eight. More lately, he has taken a data-driven deep dive into a world increasingly infused with gambling.

The book distinguishes between two kinds of gamblers/investors. He is most interested in the people who dwell in what Silver calls “The River,” who see every transaction through the lens of expected value. Riverians are totally data-driven in their outlook, question all established truths, and delight in puncturing conventional wisdom. In opposition to the River is “The Village.” Thinking of themselves as elites, Villagers believe, often without rigorous evidence, that they are accurate about the most important questions of the day.

Silver believes that much of the investment theory that advisors learn is deeply suspect. Professional gamblers (at least the good ones) demand rigor. “The stuff that people are willing to put their money behind is usually going to be better,” he writes. Or, as the economist Alex Tabarrok puts it even more succinctly, “A bet is a tax on bullshit.” One key takeaway from the book is that the economy is already well transformed into an AI-driven late-stage capitalism in which the spoils are allocated to those who understand risk.

In an interlude in the middle of the book, Silver lists 13 habits of highly successful risk-takers. Some habits are obvious (“successful risk-takers are cool under pressure.”)  Other habits advisors would be well advised to emulate: “Successful risk-takers have strategic empathy. They put themselves into their opponent’s shoes.” Another: “Successful risk-takers are process-oriented, not results-oriented.”

“The personal is the political” was a feminist rallying cry during the 1970s. The slogan inspired activists to begin with the direct issues with which they have personal experience and move from there to challenging the larger systemic issues. So it is with The Financial Activist Playbook, which reminds financial advisors that the personal is the financial. After all, what are advisors but financial activists?

The book alerts advisors to some fundamental shifts in values and attitudes about money and finance advocated by the emerging cohorts of clients who reject many of the assumptions their elders (and the advisors serving them) display. The author describes the cultural shifts that reposition conventional thinking about finance, for example, transmuting scarcity into abundance, gatekeeping into accessibility, and wealth-hoarding into wealth-spreading. It’s a cogent introduction to an emerging framework about how and to whom money flows, an understanding of which is vital to help advisors reclaim finance as a positive force for the world to better serve younger cohorts who view capitalism negatively.

Consider the way the author defines the objective of the financial activist: growing your money (to help secure a quality of life where all your financial needs and most of your reasonable financial wants are met) while simultaneously growing positive impacts for others (so that communities and the planet can flourish).

If On the Edge deals with transactional risk, Shocks, Crises, and False Alarms offers advisors a framework for assessing macroeconomic risk. Why? Because advisors as a rule are clueless about what to make of the various trends (e.g., public debt, the rise of AI), disruptions (Fed spiking interest rates, semiconductor shortages), and shocks (the COVID-19 pandemic, structural inflation) that characterize modern economic life. Are the events transient gyrations, permanent inflections or false alarms?

This book rejects the proposition that any single framework is sufficient for assessing macro risk. The authors describe the limitations of the quant school, which links data to precise forecasts. It also questions the narrative school, which purports to understand events through data-supported stories.

Philipp Carlsson-Szlezak, global chief economist at Boston Consulting Group, and Paul Swartz, BCG’s senior economist, present a powerful set of tools to recalibrate and reframe macro risks. The secret sauce is for advisors to understand the big picture, discern the trends and forecast the direction of them. If they can do that, it’s good enough.

Start by abandoning an expert-model mentality. Reliance on any single theory or approach will not consistently provide an accurate economic forecast, nor will it immunize advisors against acting on false alarms to the detriment of their clients. The authors argue that confidence in sophisticated-looking models is most misplaced when they are needed most: in times of crisis.

The takeaway for advisors is that risks can be assessed in three core areas: the real economy, the financial setting and the global environment. The real economic discussion considers an assessment of the business cycle, the drivers of long-term growth and issues associated with technology and productivity. The recipe for assessing macroeconomic risk is to develop a situationally aware mindset that is focused on getting the direction of trends right. Macroeconomic analysis should be a debate—a conversation—rather than a lecture.

To Masayoshi Son, the Japanese founder of SoftBank, there are hunters and cooks. Hunters are the people who identify and acquire targets such as Alibaba, Nvidia, Vodaphone Japan, T-Mobile and the British semiconductor company Arm. Cooks are the functionaries who extract fortunes from the acquisitions. Son (“Masa” to his friends) confides that he values hunters more than cooks, a sentiment that spells the end of a long relationship between Son and the author of this book, Alok Sama, who may be a cook, but is, according to this memoir, “a Michelin three-star” cook.

Sama, at age 51, was already one of the world’s most distinguished investment bankers. Having risen through the ranks of Morgan Stanley, he joined SoftBank as CFO in 2014. The Money Trap recounts Sama’s adventures with SoftBank and its legendary founder through five years of hopping around the world in pursuit of deals, including the infamous WeWork debacle.

Readers who want to be in the room where multi-billion dollar deals happen are treated to detailed accounts of the back-and-forth gamesmanship required to massage egos and close deals. Readers will also thrill by the luxurious surroundings—the corporate jets, the sea urchin sushi that the author craves, and the $5,000 per night hotel suites that are used for little more than showering between meetings.

The author rarely challenged Masa’s dealmaking. When he did, Masa should have listened. Sama saw through Adam Neumann’s WeWork bluster. Masa ignored the author, and SoftBank lost a cumulative $14.4 billion through its disastrous bet on Neumann. Sama left SoftBank in 2019 and enrolled in a creative writing class at NYU. The Money Trap is the worthy result.

Fans of “Downtown” Josh Brown, the co-founder and CEO of Ritholtz Wealth Management, star of CNBC’s Halftime Report, and creator of The Reformed Broker blog, arguably the most popular financial blog in the world, will delight in You Weren’t Supposed To See That: Secrets Every Investor Should Know. The book—a combination of memoir, manifesto, expose and screed—is always illuminating.

The chapter called “Everyone is a Closet Technician” is a good example. “Everyone is a closet technician,” Brown writes, “and in a panic or market correction, this truism is even more, um, truistic. A technician is someone who cuts right to the chase and studies actual prices and behavior instead of puzzling over the causes of prices and behavior like everyone else.”  Discussing causes is a much more interesting conversation and accounts for most of the blather on financial shows. Discussing price—and all the rigor that goes into it—tells investors the truth about what’s actually going on. That’s just one of the many secrets promised by the subtitle.

Brown’s conversational style suggests that the secret ways of seeing the investment world are available to any reader who dips into the book. The book discloses the overlooked tools, hidden truths and traps deliberately designed to confuse investors. Brown is a business owner as well as an investor and, thanks to his blogs and broadcast events, has interviewed virtually every important investor, entrepreneur, and player in the industry. From each, he extracts tips and hacks that advisors can implement right away.

Private Equity: A Memoir recounts Carrie Sun’s experience as personal assistant to the fabulously wealthy Boone R. Prescott, the pseudonym of the founder of an equally fictitious private equity firm called Carbon. (It’s been reported in the publishing trade press that Carrie Sun’s book originally identified the private equity firm and founder she worked for as Tiger Global Management and its founder, Chase Coleman III. But a lawsuit was threatened, hence the pseudonym. Sun has neither denied nor confirmed the actual identity of the company or founder she worked for.)

From her initial job interview (she had to endure a total of 14 interviews, including one with the wife of the founder) to the moment when Sun decided she had to quit for the sake of her health. In between, the gig came with many perks and expensive gifts. Sun learned a lot, but in the end, she felt trapped by a never-ending cascade of demands no mortal could possibly fulfill. Rarely do we get such an intimate glimpse of life and work at the very pinnacle of late-stage capitalism.

Private Equity reveals what it takes to sustain a fabulously successful private equity firm. The costs and privileges arrive in roughly equal measure, with the costs for the workers usually outweighing the privileges for the boss. The memoir also reveals the inner ordeals of a privileged young woman trying her level best to succeed in a world determined to make her doubt herself.

It’s well known that stock and currency traders in New York are a rowdy bunch. But even the Wolf of Wall Street has nothing on the profanity and sheer alcoholic excess displayed by traders in London. In this memoir, we meet Gary Stevenson, a striving 19 year old, who by virtue of real mathematical ability, improbably gets admitted to the prestigious London School of Economics. There he wins a contest—the “trading game” of the title—and thereby earns an internship and then a lowly job at Citibank trading on the London STIRT (short-term interest rates trading) desk.

Along the way, he explains FX trading—both in theory and operation—in clear and simple language that is worth the price of admission to this memoir. Trading is actually a series of swaps: lending one currency while borrowing another and pocketing the small differences in the interest rates of the two. Traders are gamblers betting on the direction of interest rates in multiple currencies. Here, the author invokes some of the gambling themes described in Nate Silver’s On The Edge: “The ideal strategy [for FX trading] depended on the level of player against which one was playing; that weak players could be beaten with simple arbitrage; that the more complex players. … could be thrown off by aggressive loudness.”

Like most successful traders, Stevenson was probably more lucky than smart. In 2008, the global financial meltdown prompted most central banks to reduce interest rates to zero or even lower, offering unprecedented opportunities for interest rate arbitrage. He inevitably suffers a setback, prompting this observation: “Every trader has a pain threshold. Every trader has an amount they can lose. You could have the best trade in the world, but if you hit your pain threshold, it doesn’t matter, you’ll lose all your cash.” That lesson prompts the author to offer two rules for trading (and life): first, be right in the end; second, be alive at the end.

The rooster can be forgiven for thinking that the sun rises to hear him crow.

When a chicken does it, it’s a harmless cognitive bias. Much more foul is when advisors mistake cause and effect. Cognitive biases are well-studied phenomena. It’s the belief that one’s internal thoughts or that specific words or rituals can influence the external world. Superstitions are one form of magical thinking. Manifestation statements, whether couched in the negative (“the universe is out to get me!”) or the positive (“the universe wants me to prosper!”), are really conspiracy theories, because they play into the narrative that the universe magically cares about individual outcomes.

While magical thinking is an age-old quirk, a bug in the brain’s operating system, the author says that magical overthinking is a different animal: “distinct to the modern era, a product of our innate superstitions clashing with information overload, mass loneliness and a capitalistic pressure to “know” everything under the sun.”

Like other books on this list, The Age of Magical Overthinking was born out of the chaos of the COVID-19 pandemic. While not a memoir, the author delves candidly and sometimes painfully into the ways magical overthinking has disrupted her life.

In a moving chapter on the sunk cost fallacy, Montell describes how she justified staying in a detrimental romantic relationship with a man she calls “Mr. Backpack” long after she realized she was getting lost in the relationship. Through it all, Montell is intimate about how she herself has succumbed to many of the cognitive biases described in the book, giving the reader an unfiltered glimpse into the mind of a brilliant yet unsophisticated woman painfully determined to move into the light.

Has a client or prospect ever asked you to recommend a children’s book about money or investing? Finally, there’s a book that fits the bill. Priceless Facts about Money, illustrated by Caitlin Stevens, is at once informative and charming. Mellody Hobson is perfectly positioned to write such a book. She is co-CEO and president of Ariel Investments, the first African American-owned mutual fund in the U.S and serves as chairman of Starbucks as well as on the board of JPMorgan Chase & Co. Time magazine listed her as one of the 100 Most Influential People.

Hobson’s passion for financial literacy shines through this book designed for children from age 6 to preteens. It starts with a short history of money, from bartering to stocks and bonds. Children will learn about allowances, compound interest, supply and demand, inflation, profit and loss, the origins of credit, and why money gets such creative nicknames (“bacon,” “bread,” “dough,” “bucks,” “clams,” “greenbacks,” C-notes.”). I learned something new in the section that demystifies the meaning of the numerous symbols on U.S. currency.

At only 76 pages, Priceless Facts about Money is easy bedtime reading. The questions it asks will prompt useful conversations about the important role that money has played in families and nations since the beginning of history. Advisors would do well to have copies of the book on display in their waiting areas.

“Like most kids, I knew the price of candy, but I also knew that a steak cost more than a hamburger. My mom used to show me the phone bill, the electricity bill, and the water bill. (Yep, water cost money.) She even told me how much we paid each month to live in our apartment. These added up to the ‘cost of living.’”

On the other side of risk (the subject of many of the books on this list) lies reward. Once you have been rewarded with billions of dollars, you are faced with the existential challenge of what to do with it. For billionaire Asher Jaffee—aging, white and living in the fantasy that his riches were self-made—philanthropy is the response. He is finally ready, he thinks, to give most of his billions away. But giving away money, as most advisors know, is messy. Entitlement is set in the glitzy intersection of the commitment to acquire money and the unequal commitment to relinquish it. Entitlement puts wealth and philanthropy on trial.

Enter Brooke Orr, a privileged young graduate of Vassar College. She becomes Jaffee’s program manager at the foundation. (It’s fun to compare the casualness of the fictional job interview in Entitlement with the very real job interview ordeal Carrie Sun endured in Private Equity.) Jaffee soon regards the new assistant as the embodiment of his daughter, who died on the trading floor of Cantor Fitzgerald on 9/11. Soon Brooke becomes Jaffee’s protégé. He challenges Brooke to identify a worthy cause that the foundation can support. To his credit, Jaffee takes his role as a mentor seriously; while his thoughts can stray, the billionaire’s behavior with Brooke is impeccable. The same cannot be said of Brooke.

Humiliated and seduced by the wealth surrounding Jaffee, Brooke goes off the deep end and painfully betrays her mentor, blows up a good job and sacrifices the important relationships in her life by succumbing to the corrupting power of wealth.

A slowly boiling sense of entitlement unravels whatever integrity Brooke had. It is said that money, like power, corrupts, and absolute money corrupts absolutely. So it is with Brooke. The proximity to Jaffee’s billions causes her to go off the deep end. “She thought she knew who she was, that most fundamental of things, but proximity to Asher Jaffee had somehow obscured her sense of herself.” By the end of the book, she is free because she has lost everything and is at peace, a reference to an earlier observation about Jaffee’s truest philanthropic attitude: “So, he was declaring it aloud: he would get rid of his money until he was left with only peace.”