Machievalli 2.0

Conor Purcell
Mar 24 · 6 min read

The man behind American Apparel’s most controversial (and effective) ad campaigns has reinvented himself as a business philosopher. His book, The Obstacle is The Way became a surprise hit among US athletes and his latest, The Ego is The Enemy is set to blast him into the mainstream.

You might not have heard of Ryan Holiday, but he is part of a new breed of authors that is revolutionizing publishing. Holiday, and others like him (writers and investors such as Tim Ferris and Tucker Max), have built personal brands worth millions. Holiday — who dropped out of college when he was 19 — makes his money from books, consulting work (he advises authors, musicians and brands) and from one-on-one phone consultations (costing $33 a minute). He is part of what’s termed the ‘new economy’ — mobile, tech-savvy twenty- and thirty-somethings who promote themselves (hiring a PR company is so passe) and write, broadcast (mainly on podcasts) and consult. They make a lot of money, promote and invest in their friends’ projects and, crucially, are open about the whole process.

The subtext for their fans is: “Yes, you can do this too.” Holiday first made his name not from openness, but from deceit. He was in charge of marketing for American Apparel, the clothing brand renowned for its marketing campaigns — often smutty, often controversial, but always effective. He mentioned one of his tactics in his debut book, Trust Me I’m Lying, a warts and all account of his time as a PR consultant.

To take just one example: American Apparel was about to launch a new range of dog clothes. The day before the launch, Holiday got an intern to fax an image of a dog wearing one of the Halloween costumes to a number of bloggers with the headline: “I work at American Apparel but even I can’t believe what they have done now!” The bloggers bit and the article got massive coverage — taking advantage of the currency of outrage so popular among bloggers — and the clothes sold out. Job done.

When he was promoting Tucker Max’s film, I Hope They Serve Beer In Hell, he defaced the film’s promotional poster with graffiti accusing Max of misogyny and then sent photos of the vandalism to blogs claiming it was part of a real protest movement against Max’s sexism. “I orchestrated fake tweets and posted fake comments in articles online. I even won a contest for being the first one to send in a picture of a defaced ad in Chicago.” The tactic worked: the book the film was based on got a huge amount of publicity, ending up at the top of The New York Times bestseller list.

While these tactics might seem underhand, Holiday claims the new media landscape is fundamentally flawed, an echo chamber of lazy, deceitful bloggers and reporters, increasingly blinded by the need to get eyeballs on stories. Holiday makes no bones about the fact he took advantage of this system to promote his clients’ products, declaring on the first page of the book: “I’m paid to deceive. My job is to lie to the media so they can lie to you.”

There is some disconnect between Holiday the amoral media manipulator and Holiday the author. If Trust Me fell short of being an actual mea culpa, he at least laid the tactics out there, which unsurprisingly did not go down too well with much of the media he had criticised. It was hard to believe he was exposing these secrets because, as he claimed in the book’s introduction, he was “tired of a world where blogs take indirect bribes, marketers help write the news, reckless journalists spread lies, and no one is accountable for any of it. I’m pulling back the curtain because I don’t want anyone else to get blindsided”.

It’s hard to think of this statement as anything other than another manipulation, another tactic to sell his book. But, far from being a PR overlord mired in the New York media landscape, Holiday lives a rather simple life. Holiday is based in a rural part of Texas, and his Instagram feed is full of pictures of his pets (which include goats, chickens and dogs). Like Tim Ferris, he believes in doing nothing that is not necessary.

His work schedule is relentlessly logical: no extraneous meetings, phone calls or e-mails, a daily to-do list written on an index card and at least three hours of writing a day. In the afternoon he runs or swims, and then fixes his schedule for the following day. Unlike many in corporate America, he values sleep; in an interview with the Lifehacker website he said: “I think it’s important to get at least seven to eight hours. I can count on one hand the times I pulled an all-nighter in my life. I think working really late is overrated and usually the result of poor planning.”

He keeps meticulous notes and something he calls a Commonplace Book, which is essentially a filing system. “Every book I read is broken up and digested on 4x6 inch cards, which are all broken up loosely by themes. I don’t have a great exact memory but I know in broad strokes what I have on these cards and whenever I’m writing or speaking and need it, I pull it out and find it,” he told Lifehacker.

This ethic has enabled him to write four books in five years, a remarkable output. In his 2014 book, The Obstacle Is The Way, Holiday focused on a philosophy that has become increasingly popular in the US: stoicism. One of the four principal schools of philosophy in ancient Athens, and the most practical, stoicism is all about maintaining a calmness and a strength of will no matter what troubles you may face. Its most famous exponent, Seneca, believed destructive emotions (envy, shame, greed) result in bad decisions. Seneca practised what he preached, for after being wrongly accused of being involved in a plot to assassinate the Roman Emperor Nero, he was ordered to commit suicide.

In stoic fashion, he did as he was commanded, cutting three veins and drinking poison. Modern stoicism is not nearly as dramatic, and has become a fashionable philosophy among tech entrepreneurs and venture capitalists: men (it’s nearly always men) who believe they can bend the world to their will. It’s no surprise that Obstacle became a hit among that demographic, as well as among US athletes. Indeed, everyone from Arnold Schwarzenegger to LL Cool J to Chicago Cubs manager, Joe Maddon read it.

“Stoicism as a philosophy is really about the mental game,” Holiday says. “It’s not a set of ethics or principles. It’s a collection of spiritual exercises designed to help people through the difficulty of life. To focus on managing emotion; specifically, non-helpful emotion.”

He has returned to this theme with his latest book, Ego Is The Enemy, in which he focuses on everyone from Marcus Aurelius to John D Rockefeller, mining history to show how various figures “remade the world in their image with sheer, almost irrational force… who fought their egos at every turn, who eschewed the spotlight, and who put their higher goals above their desire for recognition”.

What sets Ego apart from other self-help books is the intelligence of the writing and the real-world examples from history — Holiday is no starry eyed optimist, and his tone is relentlessly logical. Cleverly, his books promote the same tactics his company Brass Check offer to clients: promotion, editing, marketing and strategic advice. His clients include many of his peers: Tim Ferriss, Lewis Howes, James Altucher, as well as everyone from Google to Tony Robbins.

In a world where the dominant narrative is one of scarcity (success for you means less chance of success for me), Holiday is refreshing in his openness and, ironically, his honesty. This media manipulator has come of age, and may just be about to hit the big time.

This article was first published in the October 2016 issue of Portfolio magazine, Emirate’s first and business class title.