How a Former Canadian Spy Helps Wall Street Mavens Think Smarter

Shane Parrish was a cybersecurity expert at Canada’s top intelligence agency and an occasional blogger when he noticed something curious about his modest readership six years ago: 80 percent of his followers worked on Wall Street.

The blog was meant to be a method of self-improvement, helping Mr. Parrish deal with a job whose pressures had increased with the growing threat of global hacking. But his lonely riffs — on how learning deeply, thinking widely and reading books strategically could improve decision-making skills — had found an eager audience among hedge fund titans and mutual fund executives, many of whom were still licking their wounds after the financial crisis.

“People just found us,” Mr. Parrish said. “We became a thing on Wall Street.”

His website, Farnam Street, urges visitors to “Upgrade Yourself.” In saying as much, Mr. Parrish is promoting strategies of rigorous self-betterment as opposed to classic self-help fare — which appeals to his overachieving audience in elite finance, Silicon Valley and professional sports. His many maxims cite Ralph Waldo Emerson, Bertrand Russell and even Frank Zappa. (“A mind is like a parachute. It doesn’t work if it is not open.”)

Today, Mr. Parrish’s community of striving financiers is clamoring for more of him. That means calling on him to present his thoughts and book ideas to employees and clients; attending his regular reading and think weeks in Hawaii, Paris and the Bahamas; and in some cases hiring him to be their personal decision-making coach.

“These guys are driven to get that incremental edge — they are competitive, gladiatorial in that respect,” said Mr. Parrish, 39. “We are trying to get people to ask themselves better questions and reflect. If you can do that, you will be better able to handle the speed and variety of changing environments.”

To do that, Mr. Parrish advises investors like Scott Miller, the founder of Greenhaven Road Capital, to disconnect from the noise and read deeply.

“I will leave my computer and go into a separate room to read,” said Mr. Miller, an early sponsor of Farnam Street who is currently reading “Atomic Habits: An Easy and Proven Way to Build Good Habits and Break Bad Ones,” by James Clear. “It feels weird to do this in the middle of the day — but I do it.”

Mr. Parrish’s site has drawn the attention of some of the biggest names in finance. Dan Loeb, one of the more prominent hedge fund executives on Wall Street, is a big fan. And Ray Dalio of Bridgewater, the world’s largest hedge fund, recently did a podcast with him.

“Shane is a special person,” Mr. Loeb said via email.

Few Wall Street obsessions surpass the pursuit of an investment edge. In an earlier era, before computers and the internet, this advantage was largely brain power: Warren Buffett plucking a nugget from an annual report or George Soros making a seismic bet against a currency.

Today, information is just another commodity. And the edge belongs to algorithms, data sets and funds that track indexes and countless other investment themes. This has been devastating for hedge fund and mutual fund managers who make their living trying to outsmart the stock market.

With their business models under attack, they are searching for answers. And Mr. Parrish has a simple solution: reading, reflection and lifelong learning.

“These days, if you are not getting better you are falling behind,” said Mr. Parrish, who is reading “The Laws of Human Nature,” an examination of human behavior that draws on examples of historical figures by Robert Greene. “Reading is a way to consume people’s experiences, to learn something timeless and then apply it to your life.”

Chuck Royce, the founder and former chief executive officer of Royce mutual funds, who oversees $4 billion in investments, said he stumbled on Mr. Parrish’s site and related to it immediately.

Mr. Royce developed a reputation as one of the industry’s most astute fund managers, specializing in small, high-quality companies in the 1970s. But in the recent period of low interest rates, his main mutual fund’s performance has suffered.

“I failed to understand that in this period of zero rates, inferior companies would outperform high-quality companies,” said Mr. Royce, who was part of a group that spent a long weekend talking books and big ideas with Mr. Parrish in Hawaii two years ago.

Mr. Royce has embraced Mr. Parrish’s core principles. He gets up at 5:30 every morning to do his daily reading, which currently includes “Thinking in Bets: Making Smarter Bets When you Don’t Have All the Cards” by Annie Duke, a former poker champion — and a big favorite among investors these days. At the office, Mr. Royce works from a couch strewn with papers. His Bloomberg terminal is in another room.

“It is all about habits,” Mr. Royce said. “Setting goals is easy — but without good habits you are not getting there.”

Some executives have long sought insight from the printed page — and not just in the business section. Emmanuel Roman, the chief executive officer of the bond giant Pimco — who is reading “On Grand Strategy,” an assessment of the decisions of notable historical leaders by the Pulitzer Prize-winning biographer John Lewis Gaddis — called reading “a pure passion.” And Lloyd Blankfein, the chairman of Goldman Sachs, has talked up the benefits of reading books, especially those not related to economics or finance.

Mr. Parrish is an unlikely guru, a computer scientist from Halifax, Nova Scotia, who seems bemused by his sudden cachet. On a recent swing through New York to meet with clients, Mr. Parrish was dressed in a T-shirt and shorts and carried a worn backpack. Slight and balding, he looked more like an unhurried graduate student than a counselor to some of the wealthiest executives on Wall Street.

Mr. Parrish joined the Communications Security Establishment, a division of Canada’s Defence Department, straight out of college. His first day was Aug. 28, 2001, and he was soon promoted in the tumult that followed the Sept. 11 attacks. Suddenly, he was managing a large staff at the age of 24.

Wanting to improve his decision-making skills, Mr. Parrish found inspiration in Charlie Munger — Warren Buffett’s longtime investment partner. Mr. Parrish quickly became an acolyte, drawn to Mr. Munger’s thoughts on multidisciplinary thinking and mental models.

He pored over Berkshire Hathaway annual reports and became a regular attendee of Mr. Buffett’s yearly meetings in Omaha. The name of his site is another tribute to the billionaire investor: Berkshire Hathaway’s address in Omaha is 3555 Farnam Street.

Last year, Mr. Parrish left intelligence work to tend to the site full time. He would not disclose how much his various projects were making. Farnam Street now consists of book lists, essays, podcasts and a vibrant social network — all of which are anchored by Mr. Parrish’s self-improvement musings. There are also branded goodies to be had, such as a decision-making journal and a Farnam Street thinking cap.

Some 190,000 people have signed up to Brain Food, his free weekly newsletter. Mr. Parrish’s more dedicated followers pay $250 a year to become part of his “knowledge community” — a premium site with a private discussion forum and additional content. They have flocked to his social network, trading book ideas and meet-up suggestions in Toronto, Dubai and London.

James Aitken, an independent investment adviser in London who counsels some of the world’s largest investors, was among the readers that came upon Mr. Parrish in 2012. Since then, Mr. Aitken has revamped his work habits, pushing himself to disconnect from all his screens and read books — ideally for at least two hours a day.

“He is so indispensable to me that, beyond becoming a part of his network, I will occasionally write him a check at the end of the year,” Mr. Aitken said.

Mr. Aitken now pushes his clients to increase the time they spend reading and thinking away from their screens. Twice a year he sends out a list of books — including history, biography, finance and economics, self-help, and more — from which clients can choose a number of books as gifts. He has sent out about 2,300 over the past 10 years.

“Every world-class investor is questioning right now how they can improve,” he said. “So, in a machine-driven age where everything is driven by speed, perhaps the edge is judgment, time and perspective.”

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