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My Thoughts After Reading Conspiracy by Ryan Holiday

Portrait of a reptilian politician

My thoughts after reading Conspiracy.

Conspiracy: A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire, alternatively titled Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue is a book by Ryan Holiday, published in 2019. It details how Peter Thiel took out Gawker, and how he conspired for years before he did so.

Conspiracy brings two things into my mind when I hear the word. Some person manipulating the world from the shadows, using everyone like a chess piece (or a Shogi or Go piece), or, the stupidly executed plans in the three kingdoms. (Read about them on the Farce of the Three Kingdoms!) At times, you come across books which you can’t review, because their subject matter is just too great, or the concepts which they talk about are beyond your capability to analyze. Now, this book is not like Debt: the First 5000 Years, which actually changes how the reader views money. Instead, this book is about revenge, pure, and simple.

When I began to read this book, I didn’t think that I would end up writing an article on it. But as I went through the chapters, I realized that I could express my thoughts about it. But I was terrified to do so. The subject is very controversial to say the least, and though I don’t think anyone would come after a small-time blogger like me for writing my thoughts here, I do know that this entire matter did start with a small blog post.

And yet, I’m gonna write it anyway, and think about the consequences later.

First, some background.

Gawker was a media empire which was created by Nick Denton in the early 2000s. It primarily focused on celebrity news and gossip. Initially starting out as a small blog, it quickly gained in popularity, and pulled in millions of readers until its end in 2016.

Gawker came under scrutiny for posting videos, communications and other content that violated copyrights or the privacy of its owners, or was illegally obtained. They often exposed many private things of public figures, and no one could bring it to heel because it was independent, and didn’t rely on money from other sources.

Personally, this entire era of the internet escaped me. I didn’t have access to a computer until 2012, didn’t learn to use it until 2013, and didn’t look beyond YouTube until 2015 – 2016. I did stop using social media like Facebook very early, though, because their novelty ran out. Granted, I do use them now for marketing purposes, but my marketing sucks, that’s all you need to know about it.

According to the book, Gawker employed writers who weren’t accepted into the field back in the day, people with school and college debt who were promised that they could have everything if they studied. The promise fails to materialize, and when they had a chance to rail against this, they took it with both hands.

Come to think of it, the same thing is still continuing in 2022, with the younger generation railing against the older generation and their promises.

Getting back to the point, let’s know the players.

Nick Denton is the creator of Gawker, aside from other ventures; that is his most successful one. Peter Thiel is an investor who invests in tech startups. He invested in PayPal, Facebook, and Palantir. He also used to play chess, but hasn’t been active since 2003, though he did make the first ceremonial move in the 2016 championship between Magnus Karlson and Sergey Karjakin. He also admires Capablanca, who was the champion of chess during the 1920s. (Read about it here.)

There are a lot of similarities between them. for example, they both are immigrants, and are both successful (They do look successful from down here) and apparently read a lot of books. Reading this book actually made me realize how much people underestimate books these days.

But there are differences as well, and they are quite sharp. Nick likes to gossip, while Thiel likes his privacy. Nick revels in the public attention, while Thiel sort of loses control over the situation if the matter reaches the public.

How did the issue begin?

Gawker outed Thiel as gay despite his attempts to keep it private. Now, it might not raise any eyebrows today (that is a lie; many people will raise their eyebrows even now) in 2007 it was a big deal. This outing could end up costing Peter a lot.

At first, when he thought of what he could do, many people told him that he could do nothing, and that it is the way things are now. But that never agreed with Peter, and he finally decides to conspire in 2011 against Gawker.

“I came to believe that the nastiness of the internet was not a function of a technology or various things that have gone wrong, but the function of one particularly nasty media company led by a particularly sociopathic individual and that if I defeated Gawker, it would actually change the media landscape,” Peter Thiel, chapter 3.

I actually laughed out loud after reading that. Internet didn’t need Gawker to be nasty before Gawker, and it doesn’t need Gawker to be nasty now. I wonder whether he still thinks the same way or not? One thing I do know for sure. Internet has not improved since Gawker was taken out.

Criticism of the book.

Now, when a book like this is written, there are a lot of criticisms for it. However, the main one seems to be that it presents Peter Thiel in too much of a positive light, a hero, a face to the heel of Gawker. I leave that for others to decide. Personally, my own criticism is that it just goes too heavy on righteousness, justice, and “Christian values.”

Come now. Justice and righteousness are hollow concepts. Only the powerful can decide what is justice and righteous and what isn’t. And remember, everyone claims that justice is on their side.

I do think that the book is well sourced; in particular it uses quotes from Prince, written by a certain Italian who’s name I can’t spell. If anything, this book convinced me to actually read Prince, and see what I can get out of it.

Why did I read this book?

I usually ask at the end of my review of a book whether it is worth reading or not. But here, I ask myself, why did I read this book? What did I get out of it?

Well, the first reason is, conspiracies are fun to read in fiction, and they are even more fun to read in real life. Especially when the people involved are still alive and can answer the questions of the author. Second, I learned through this book that the last ten years or so of American politics can be indirectly (and sometimes directly) traced back to this conspiracy. The gamergate controversy? They didn’t start it, but took advantage of it and fanned the flames. The same tactics as the gamergate will be used by political trolls later on. It also helps that Thiel is a huge Trump supporter, and still, he is deeply involved with politics. It also helps that Ryan is a good writer, and at least to me, his explanations came clear and concise.

So, those were two reasons why I actually read this book.

Anyway, this ends my ramblings here. Follow me on Twitter..


Published by Tanish Shrivastava

I'm a guy who likes programming, chess, and writing.

8 thoughts on “My Thoughts After Reading Conspiracy by Ryan Holiday

  1. I didn’t know Ryan Holiday wrote books like this. All I think about when I see his name is Stoicism. To be fair, after your description, I think I’ll give this book a pass, so thanks for roughly telling me what it’s about!

    Liked by 1 person

    1. I’m not much of a big fan of Stoicism, I do plan to read his book about ego and the enemy, (I forgot the title) in the future.

      To be honest, he didn’t come off as a stoic in this book. Instead, he actually supported one party, but I suppose that was the part of the job description for writing this book. In which case, good job? I guess?

      Anyway, you can skip this book. It is interesting, amusing, but not worth the time if you have better things to do. Thanks for the comment, Stuart!


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