Conspiracy by Ryan Holiday Review
A true story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire
You can buy this book in the following link.
Talk about a long subtitle! Conspiracy’s plot is summed up in there, narrating the successful conspiracy made by Peter Thiel (co-founder of PayPal and venture capitalist) against the former website “Gawker” and their founder Nick Denton.
Holiday gets exclusive access to almost everyone involved in the conspiracy, and what a ride do we live through reading!
Being the third book from Ryan Holiday I’ve read in the last couple of months, I believe it’s the most fun. I turned page after page, really immersed in the conspiracy, partly amazed by the planning and scheming as well as the portrayal of Gawker’s owner, Nick Denton.
The way Holiday portrays the story is the one of a mere observer, one can see his influences shinning throughout (I had read Robert Greene’s book that Holiday regularly recommends a few weeks before). The real story is so deep, fun and engaging, I started asking myself how had not Hollywood made a movie out of the story (it supposedly is link here).
The pace is like those found in Michael Lewis’ books, (think of The Big Short, Liar’s Poker or Moneyball). Going from “character” to “character”. You empathize with the outing of Peter Thiel by Gawker, the bullylike attitude, that has seen a rise through Twitter and is common in politics since the Trump era (including Trump’s tweets and bullying received by Trump1). The billionaire is not the only one, you end up empathizing with, Denton ends up as a kind of “victim” as well.
There are no good guys in this book, was Gawker’s existence good for society in general, I don’t think so.
Is going after a company that constantly publishes truths and lies for visits a moral crusade? I do not have an answer.
Did Thiel destroy part of himself by taking down Gawker? Probably.
Did it give repentance to Denton? I’m not sure.
What caught my eye to read this book?
I had read Peter Thiel’s Zero to One (book, review) a few weeks ago and I’m a big fan of Ryan Holiday (this is the third book by him I read and soon I’ll review the fourth). He has become my guide through books the last couple of months, he is a fun and thoughtful writer and really recommend his books, podcast or Youtube channel.
Some quotes I highlighted
What Denton did, in effect, was turn writing, social commentary, and journalism into a video game. Writing wasn’t a craft you mastered. It was a delivery mechanism.2
The distinction between a conspiracy and a feud is as much in the time it takes for one to spring into action as it is in the type of action that one takes. In a fight, one responds to a punch by throwing a punch. In a conspiracy, one holds their punches and plots instead for the complete destruction of their antagonist, while often intending to escape with knuckles unbloodied and untraceable prints.3
Selfish people are easy to understand. They act on motives. It’s when we begin to see that something deeper than self-interest is at play, that they cannot be made to see reason, that we begin to despair of ordinary means of resolution.4
With his first hire, Thiel’s conspiracy is stronger, by virtue of simply existing, yet it is also naturally weaker. This is the risk of combining with allies. The strategic benefit of adding a new coconspirator comes at the cost of substantially increasing the chance of getting caught.5
We are often taught that successful strategy is a matter of boldness, but it has also always been the case that it’s as much a matter of patience and due diligence as it is of noticeable action.6
Deterrence is an important strategy. The more intimidating you are, the less people conspire against you. Yet the powerful must always be very careful with their threats, with their demonstrations of superior resources. Aimed poorly, they have a nasty habit of backfiring.7
Random Thoughts While Reading This Book
This book tells a story, but it’s main topic is one of Power (with a capital P). This was a war between two of the main types of power we know today, media and money. There is no clear winner, even though Gawker filed for bankruptcy and Hulk Hogan won millions of dollars.
There are big questions for society spread out in this book regarding our relationship to secrets, privacy, and the right to tell these secrets by others. It’s easier for us to determine what is right and what is wrong where damage is quantifiable or legally regulated. The difficulty arises when we try to differentiate right from wrong in foggy grounds. Here is when morality and personal responsibility enters the play, we need to think on these topics, discuss them with our friends and practice them on our daily life. Ethics matter. Philosophy gains bigger importance when we incorporate it to our daily lives.
I really like the image of Denton, in the sunk ship that was Gawker, reading Seneca, as Holiday says:
Seneca is the author you read when your life’s work has been destroyed, as Denton’s undeniably has.8
I review books weekly and deepen on some thoughts and send them as a newsletter. You can subscribe here.
Disclaimer: Some of the links in my posts may have affiliate links. I receive some income that helps me finance time spent on these posts as well as preparing other posts. Thanks for your help!
Holiday, Ryan. Conspiracy (p. 17). Penguin Publishing Group. Kindle Edition.
Ibid, (p. 18)
Ibid, (p. 43)
Ibid, (p. 58)
Ibid, (p. 65)
Ibid, (p. 143)
Ibid, (p. 8)