Digital Matchmaking

Ryan Holiday

by

Ryan Holiday is a writer and media strategist. He had a successful marketing career at American Apparel and went on to found a creative agency called Brass Check. He writes frequently about marketing, career and philosophy.

He lives on a ranch outside Austin, Texas where he raises cattle, donkeys and goats.

Projects:

Recommending Books:

From Zero to 50,000: How I Built A Big Email List Exclusively About Books I Liked

This post is phenomenally useful. I’ve signed up to his reading list and always end up making a couple of purchases.

Writing Routines

Every week, we go deep into the how, what, when, and in-what-order of writing and the writing life. The result is Writing Routines: A close look at the craft, through the eyes of its very best practitioners.

Check out his own profile Bestselling Author Ryan Holiday on Notecards, Mornings, and the Work

Books

Trust Me, I’m Lying

Trust Me, I’m Lying was the first book to blow the lid off the speed and force at which rumors travel online—and get “traded up” the media ecosystem until they become real headlines and generate real responses in the real world. The culprit? Marketers and professional media manipulators, encouraged by the toxic economics of the news business.

Whenever you see a malicious online rumor costs a company millions, politically motivated fake news driving elections, a product or celebrity zooming from total obscurity to viral sensation, or anonymously sourced articles becoming national conversation, someone is behind it. Often someone like Ryan Holiday.

He used the techniques from the book to get featured in many news reports. The catch? The information he told them was false. The case study was featured at Forbes and generated a lot of conversation in the PR world. The original article was at How This Guy Lied His Way Into MSNBC, ABC News, The New York Times and More.

The founder of HARO, Peter Shankman responded by arguing that one idiot wouldn’t ruin HARO for everyone. Holiday wrote a follow up at Dissecting Peter Shankman’s Hypocrisy.

He even lied to generate press around the book deal. He shared how easy it was to spread misinformation in Exposing the Racket: A Simple Stunt Reveals How Blogs Will Print Anything for Pageviews.

Buy From Amazon

Growth Hacker Marketing

A primer on the future of PR, marketing and advertising — now revised and updated with new case studies. Ryan Holiday explains the new rules in a book that has become a marketing classic in Silicon Valley and around the world. This new edition is updated with cutting-edge case studies of startups, brands, and small businesses.

In 2012, Ryan wrote an article for Fast Company about How Growth Hackers Redefine The Game.

He wrote about book acquisition and the entire launch strategy at Disrupting How Bestsellers Are Made: Apply Startup-style Growth Hacking To Publishing. It is worth reading the entire post and following all the links; the article provides a better overview than I could.

It later became a course.

His goat liked it.

Buy From Amazon

Perennial Seller

Bestselling author and marketing strategist Ryan Holiday reveals to creatives of all stripes—authors, entrepreneurs, musicians, filmmakers, fine artists—how a classic work is made and marketed.

In Perennial Seller, Holiday shows readers how to make and market their own classic work. Featuring interviews with some of the world’s greatest creatives, and grounded in a deep study of the classics in every genre, this exciting new book empowers readers with a foundational set of innovative principles.

Perennial Seller was published in July, 2017. He shared the behind the scenes process in Here (with 2 Years of Exhausting Photographic Detail) Is How To Write A Book.

He also wrote comprehensive guest posts expanding on Perennial Seller ethos:

Buy From Amazon

Conspiracy

In 2007, a short blogpost on Valleywag, the Silicon Valley-vertical of Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel’s sexuality had been known to close friends and family, but he didn’t consider himself a public figure, and believed the information was private.

This post would be the casus belli for a meticulously plotted conspiracy that would end nearly a decade later with a $140 million dollar judgment against Gawker, its bankruptcy and with Nick Denton, Gawker’s CEO and founder, out of a job. Only later would the world learn that Gawker’s demise was not incidental–it had been masterminded by Thiel.

I wrote a book about how Hulk Hogan sued Gawker, won $140M, and bankrupted a media empire…funded by billionaire Peter Thiel to get revenge (or justice). AMA

Buy From Amazon

The Daily Stoic

How a book on stoicism became wildly popular at every level of the NFL

Buy From Amazon

The Obstacle Is The Way

In 2014, Ryan Holiday did an experiment. He joined forces with Tim Ferriss, publishing the audiobook under his new imprint, and featuring the book as part of the book club he was starting? It turned out that this little decision was probably the single biggest direct driver of book sales that Ryan had in his career. In Behind The Book Campaign: How to Sell 30,000 Copies in Six Weeks, he takes you behind the scenes of that collaboration and launch—numbers and all.

He collaborated with Joey Roth to create a print.

Buy From Amazon

He has also written Ego Is The Enemy, Stillness Is The Key and the Daily Stoic Journal.

Check out this comprehensive reading list if you want recommendations for other about books on Stoicism.

Favourite articles

Writing and Marketing Books

How I Did Research For 3 New York Times Bestselling Authors (In My Spare Time)

By the time he was 21, Ryan Holidays research had been used by #1 New York Times Bestselling authors like Robert Greene, Tim Ferriss, and Tucker Max. Was he a slave to study? Did he have to become a library hermit to accomplish this? No, he did it all in his spare time —on the side, often with just a few hours of work a week.

7 strategies for writing 3 books in 3 years

Though authors are unquestionably helpful to each other, they don’t always give the best advice. Think how many times you’ve heard this old trope: Just put your butt in the chair and write. It’s true, but that doesn’t help you right now, does it? Ryan Holiday doesn’t give you advice like that. Instead, he shows that there is a way to publish prodigiously while baking the marketing into your work.

The Right (and Wrong) Way to Market A Book

So many people attempt the easy way out when creating books for passive income. Their goal is often quantity over quality. And this is understandable, especially if you are trying attracted to the kindle model over other income streams that involve a bigger time investment. Ryan Holiday points out the flaws in this marketing strategy, arguing that “the most important marketing phase of a book actually comes while you’re writing it. If you don’t realize that now, it’s a big missed opportunity.” It’s a must read post, regardless of what type of book you are marketing.

There’s an emerging trend of companies that will attach your name to a generic book — and it’s horrible for entrepreneurs

Yet I still tell the vast majority of entrepreneurs and thought leaders I meet that they should not write a book — even though I could very easily profit from encouraging them to — because I know how hard it is to do it right. I know that the success the internet marketers tell them is right there for the picking is actually quite rare, and requires much more work than it appears. More directly, I know this: If the entrepreneur is already looking for shortcuts, they definitely won’t find the rewards they are looking for in books.

Troll/Outrage Culture

How the Online ‘Diversity Police’ Defeat Themselves, and Leave Us All Much Worse Off

As readers and as writers, it’s not quotas we should be chasing. It should be truth. And very rarely does what is featured in the author photo—or in the case of ancient books, the classic bust featured on the back—have much bearing on the truth of the work.

I Helped Create the Milo Trolling Playbook. You Should Stop Playing Right Into It.

“The déjà vu is not accidental. Numerous leaders of the alt-right movement read the book I published in 2012, which outlined exactly how this media strategy works. Several have told me Trust Me, I’m Lying is their bible. It’s a sad irony for me, since I wrote the book as an explicit warning about how broken our media system was and why it needed to be fixed. As I would say in interviews, the strategies that I used were designed to market books and clothes for companies like American Apparel, but I was exposing how they worked because I worried how others might soon use them to sell something more nefarious.”

Writing

Why Do You Write So Much?

So You Want To Write A Book? “Want” Is Not Nearly Enough

Reading

Career

Other:

Favourite Interviews:

Influences:

Robert Greene

Robert Greene’s Best Advice On How To Create A Classic