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Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

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An NPR Book Concierge Best Book of 2018!A stunning story about how power works in the modern age--the book the New York Times called "one helluva page-turner" and The Sunday Times of London celebrated as "riveting...an astonishing modern media conspiracy that is a fantastic read." Pick up the book everyone is talking about.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.For years, Thiel had searched endlessly for a solution to what he'd come to call the "Gawker Problem." When an unmarked envelope delivered an illegally recorded sex tape of Hogan with his best friend's wife, Gawker had seen the chance for millions of pageviews and to say the things that others were afraid to say. Thiel saw their publication of the tape as the opportunity he was looking for. He would come to pit Hogan against Gawker in a multi-year proxy war through the Florida legal system, while Gawker remained confidently convinced they would prevail as they had over so many other lawsuit--until it was too late. The verdict would stun the world and so would Peter's ultimate unmasking as the man who had set it all in motion. Why had he done this? How had no one discovered it? What would this mean--for the First Amendment? For privacy? For culture?In Holiday's masterful telling of this nearly unbelievable conspiracy, informed by interviews with all the key players, this case transcends the narrative of how one billionaire took down a media empire or the current state of the free press. It's a study in power, strategy, and one of the most wildly ambitious--and successful--secret plots in recent memory.Some will cheer Gawker's destruction and others will lament it, but after reading these pages--and seeing the access the author was given--no one will deny that there is something ruthless and brilliant about Peter Thiel's shocking attempt to shake up the world.

334 pages, Kindle Edition

First published February 27, 2018

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About the author

Ryan Holiday

88 books15k followers
Ryan Holiday is media strategist for notorious clients like Tucker Max and Dov Charney. After dropping out of college at 19 to apprentice under the strategist Robert Greene, he went on to advise many bestselling authors and multi-platinum musicians. He is the Director of Marketing at American Apparel, where his work in advertising was internationally known. His strategies are used as case studies by Twitter, YouTube, and Google, and have been written about in AdAge, the New York Times, Gawker, and Fast Company. He is the author is *Trust Me, I'm Lying: Confessions of a Media Manipulator*, which is due out in July. He currently lives in New Orleans, with his rebellious puppy, Hanno.

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Displaying 1 - 30 of 702 reviews
Profile Image for Shiri.
100 reviews52 followers
October 20, 2019
Great storytelling, unconvinced by the "lessons"

I generally enjoy Ryan Holiday's writing. It is engaging if occasionally repetitive in the "tell them what you're going to tell them, tell them, tell them what you've told them" style. This book was even more of a page turner than his other books or than what I expected, and I found myself incredibly drawn to reading the next page and chapters even as the end was known from the very beginning.

That said, I came away quite unconvinced by Holiday's thesis about conspiracies and nowhere near as sympathetic towards Thiel as he is. As one online reviewer astutely pointed out, the tenuous connection to Gamergate is extremely troubling, and Holiday missed (or deliberately ignored) the chance to probe deeper into this. My enemy's enemy is my friend, Holiday alludes elsewhere in the book, yet when it comes to Gamergate he steers clear of any investigation as to whether Thiel or the mysterious Mr. A. supported or colluded in any way with this terrible movement. If true, it would be extremely troubling - and have now disturbing implications as well for Thiel's subsequent support of Trump.

Near the end of his book, Holiday cites Michelle Obama's "we go high" quote in order to supposedly argue that taking the ethical high ground is a losing strategy. I'm sorry, but I just don't buy it.

At the end of the day, for all of the intellectual quotes on conspiracy (which got fairly annoying, at least to this reader) and the post-hoc rationalizations, Thiel was able to do what he did mostly due to his money, rather than his secrecy. The same secrecy without the deep pockets wouldn't have amounted to very much. Yes, Gawker's lawyer team seems incompetent in comparison, but had they really been up against Hogan's own legal representation, without Thiel's backing, they would have likely won handily.

I greatly enjoyed the book in terms of storytelling, but came away clearly unconvinced. I'm one of those ambitious people Holiday refers to in his conclusion; I have a strong mission to improve the world. But if scheming in the shadows is what's needed to change this world for the better, I'm not sure I want in. No, the end does not justify the means. Perhaps this resistance is me alone, but I doubt it - Holiday himself anticipates the fact that his thesis will be controversial. Well, it certainly is that, but his arguments didn't sway me... Except maybe to convince me to think about this more. Which, arguably, is already Holiday's success as an author.
Profile Image for Brian S. Wise.
113 reviews2 followers
March 18, 2018
I complain a lot about books (and movies) being overwritten, but “Conspiracy” is the first book in a very long time I wanted to re-edit – in-book, with a marker – and read again. Because as long as he’s staying on topic (the conspiracy to sue Gawker out of business), Ryan Holiday’s book is awesome. He competently lays the foundation and tells you the story in just about as complete a fashion as you could hope for.

But by the sixth or seventh reference to Machiavelli – or the Second World War, the Civil War, or War and Peace, or Eisenhower v. McCarthy, or Caesar, or any one of a few dozen other things – you very much get a feeling of, okay, Holiday reads. And good for him. But not everything needs to be cross referenced. A story just needs to be told.

By the end of the book I was skipping entire paragraphs, sometimes pages, because they amounted to stylistic flair and had nothing to do with the conspiracy itself; it was padding. Had “Conspiracy” been allowed to be the 250-page book it needed to be, it would have been very strong. As it is, I begrudgingly rate it four stars. When it’s on point, it’s just too good for three stars.
Profile Image for Anton.
323 reviews90 followers
July 26, 2023
Re-read and a radical shift of my opinion. I jumped to conclusions too soon first time round. I finally get this book!

In order to appreciate it, you may want to get familiar with Ryan Holiday through his other writing first. I recommend:
- Obstacle is the Way
- Stillness Is the Key
- Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius

I made the mistake of reading Conspiracy first... Bad idea.

Also, for the greater context of the story, it was beneficial for me to read Robert Greene, Ryan Holiday's mentor. He is famous for:
- The 48 Laws of Power
- The 33 Strategies of War
- The Laws of Human Nature

With all the context above... this story reads like a great case study of the strategic thinking Greene promotes and the moral philosophy Holiday popularizes. So it was much more engaging and insightful this time.

The Audible format also helped. The book is quite bloated. So 3.5 roundup.

Other books that could be of interest here:
- The Founders: The Story of Paypal and the Entrepreneurs Who Shaped Silicon Valley
- Zero to One: Notes on Startups, or How to Build the Future
- Discourses on the First Decade of Titus Livius, Samizdat Edition

--- 1st read attempt review ---

Throwing my towel at 20%.

The premise and the story are incredible! But I just cannot force myself to suffer anymore through the obnoxious writing to enjoy them...
73 reviews42 followers
March 2, 2018
In 2007, a Gawker writer outed Peter Thiel as gay. In 2016, after losing a $140 million lawsuit funded by Thiel, Gawker shut down. Conspiracy is the story of how we got from A to B.

Disclosure: Gawker has tried to get more than one of my friends fired, so I didn’t shed any tears when justice was served. High-fives may have been exchanged.

The central thesis of Conspiracy is that we need more conspiracies. It's clear that nobody is willing to labor for nearly a decade in silence in order to achieve a goal. The closest we have to that is stealth mode, or maybe grad school, but one is temporary and the other appears to be permanent.

If you think of it in terms of an investment—and every decision in life can and should be modeled this way—a conspiracy has negative carry but returns skewed to the upside. Most people, and nearly all organizations, can’t tolerate this, so we have fewer than the optimal number of conspiracies.

This argument is counterintuitive, but not obviously wrong. And it's a good heuristic that when an argument is easy to dismiss but turns out to be hard to argue with, you should default to strongly believing it. If nothing else, when you find out you're wrong you do so in a way that leaves you better-informed than the conformists.

One question people asked a lot in the aftermath of Gawker's shutdown was: do we want to live in a society where a vindictive billionaire can spend years and tens of millions of dollars to ruin someone’s life? A better question is: do we want to live in a society where a blogger can spend fifteen minutes to do the same thing?

Wealth, we can all agree, has some randomness to it. If Mark Zuckerberg had taken the VC money in Boston instead of moving to the Bay, Thiel would be a lot less rich (but, between Founder’s Fund and Palantir, still very, very rich). But blogging influence is even more random. Did A.J. Daulerio pyramid up his social capital from a series of bold, contrarian bets, or did he just kind of stumble into possession of the megaphone? In investing, if you make a huge mistake your next mistake is smaller because you have a smaller bankroll. But a blogger can reset his bankroll by writing another post.

A friend of mine compares the free speech debate to the gun control debate: when they wrote the First Amendment, the Founding Fathers could never have imagined that a high-powered Assault Press like Gawker could end up in the hands of a civilian.

Gawker was simply a misuse of freedom of speech. It wasn't strictly necessary that they be destroyed, but it was a good thing. The Internet used to make society more diverse, by letting people with obscure interests congregate. It still does some of that. But sites like Gawker make the world more homogeneous, by singling out and attacking weirdos. It takes years to develop a subculture, but only minutes to whip up a mob, so Gawker contributed to the Internet's current entropic state: maximum tension, minimum agency.

And speaking of agency: Thiel and Denton are clearly, in the words of Eric Weinstein, "high-agency people." They have a vision and execute on it. That trait is in limited supply, and tends to be selected-against in high-status education and the early stages of high-status jobs. In a sense, Denton was a class traitor, by using his Nietzschean will-to-power to build an institution that mostly swatted other unique people aside.

(This book owes a lot to Girard.)

I found the style... okay.

The style of the book is 48 Laws of Power cover band. We have lots of references to ancient philosophy, ancient war, more recent war, Margaret Thatcher. You know: the cultural currency of someone torn between his love of reading and his desire to be a bro. It came as no surprise when I googled and found out that the author was a protege of Robert Greene. He has absorbed the Greene voice. If you liked The 48 Laws, you'll probably get a kick out of this book.

I recommend Conspiracy to anyone who wants to see bold plans being executed well. It's unique in that the author has access to both the protagonist and the antagonist. As to which one was which, I defer to you.
Profile Image for Tim O'Hearn.
255 reviews1,171 followers
January 11, 2019
Conspiracy is a not particularly concise showcase of Ryan Holiday's maturation as a writer. His writing style here is eerily similar to Antonio Garcia Martinez in Chaos Monkeys, or, generally speaking, my own, whenever I want to flaunt that I am well-read.

It also tells one of the most compelling and mind-boggling stories of the decade. Yes, Holiday managed to get exclusive, intimate, access to Nick Denton (the CEO of Gawker), Peter Thiel (the billionaire that everyone hates now), and Hulk Hogan (Hulk Hogan). The story has this type of complex awesomeness that is beyond descriptives; difficult to sell to an outsider. I like leaving the storytelling to storytellers, because who the hell am I really, but trust me when I say it's good.

Gawker Media was an enterprise that published gossip and speculatory articles and media. Real bottom of the barrel stuff that violated a lot of unspoken rules that generated a lot of clicks at the expense of making people feel bad about themselves. The premise behind the operation was that they were protected by the First Amendment and that the site helped hold prominent people accountable... or something. How pathetic were the articles? Well, a few years ago, I discovered that one of my coworkers at the time, who had been a college athlete, had been written about in Deadspin (formerly a Gawker company). The Deadspin writer made fun of the guy's name and the fact that he was, at the time, studying to get a Ph.d. The article's existence made me angry, and the 50+ comments under it, to this day, continue to piss me off.

If we're going to talk about "the media" in a book published in February 2018, you know there's no getting away from Donald Trump. Thankfully, the election is relegated to the tail end of the book. In those pages, what is expected to be an epic triumph is actually a party that ends at 9 PM for our conspiracists, Trump's perceived failure kind of being a bookend to the final act that is not nearly as glamorous as once imagined.

By the time you read this book, there's a pretty good chance that you know who won the lawsuit. There's a pretty good chance the media has conditioned you to hate Peter Thiel. It's a given that you spend more time thinking about Donald Trump each day than you do your loved ones. At any rate, Ryan has put together a story that leaves you basking in that post-movie glow. Coming soon to a theatre near you.
Profile Image for Gabriele.
96 reviews
March 10, 2018
Ryan Holiday says this is the best book he's written. I agree.
Profile Image for David.
Author 18 books370 followers
July 30, 2018
This was far more fascinating than I ever expected.

The short version of the story: In 2007, Gawker Media outed Peter Thiel, the billionaire investor who founded PayPal. Angered by this, Thiel embarked on what became a slow, patient campaign to destroy Gawker. The instrument of his vengeance, improbably, was Terry Bollea, better known as former professional wrestler "Hulk Hogan," who had launched a suit against Gawker for publishing a sex video of him banging his best friend's wife. Backed by Thiel's deep pockets, the Bollea lawsuit eventually ended the Gawker empire, driving it and its owner, Nick Denton, into bankruptcy.

That's the short version, but the long version turns out to be detailed, fascinating, and a far-reaching epic story that touches on political biases, the culture wars, and meditations on the nature of conspiracy and revenge.

Many people have opinions about the case based entirely on what they think of the principals. When Bollea aka "Hulk Hogan" first won his lawsuit against Gawker, public opinion was generally in his favor. The trial had shown amply that Gawker didn't care in the slightest about truth or journalistic ethics. They would publish anything without regard for the impact on its subjects. The rich and famous were favorite targets, and everyone enjoyed the schadenfreude of seeing yet another celebrity being humiliated. Worse, they operated on the principal that they were essentially untouchable. "Never start a fight with someone who buys ink by the barrel" - they relied on strong First Amendment protections coupled with the fact that even for a rich celebrity, taking on a multimillion-dollar media empire was doomed to be a losing fight.

But when it was revealed that billionaire Peter Thiel was behind Hogan's lawsuit, essentially providing infinite funds in a deliberate effort to destroy Gawker, opinion turned. Thiel was not beloved by the media, and the fact that he was a libertarian, and later a Trump supporter, cast the case in a new light for many. Now it was a story about a vengeful billionaire crushing the freedom of the press for hurting his feelings.

Any such simplistic summary does not do the story justice, and Ryan Holiday, who interviewed both Peter Thiel and Nick Denton, among others, for this book (and in fact was asked to convey messages between them) does an excellent job of plumbing the psychology of everyone involved and laying out all the complexities.

Thiel, for example, wasn't just a thin-skinned billionaire out for revenge. At the time Gawker "outed" him, his being gay was already an open secret, known to pretty much everyone who knew him. So why was he so upset at the brief story on the Valleywag blog titled "Peter Thiel is totally gay, people"? There were a number of reasons, and none of them involved embarrassment or shame at being gay. Thiel, rich and powerful as he was, was genuinely afraid of Gawker, which seemed to be picking on him, and everyone told him there was nothing he could do about it; media organizations like Gawker could expose, humiliate, and mock anyone they wanted with impunity. He came to see Gawker as a genuine societal problem, and eventually, he was persuaded that not only should someone do something about it, but that he was that someone.

And yes, if you're wondering about all the other creative ways a billionaire could inflict retribution... Thiel thought about them, and discussed options with the chief architect of his campaign. Not purely out of scruples, they elected to follow a 100% legal strategy, eschewing even legal gray areas that Thiel could easily have funded.

Terry Bollea, meanwhile, comes off as very sympathetic and vulnerable in this tale. Sure, he was rich and famous. But he was also busted up after years of pro wrestling. His marriage went to hell, his wife ran off with a younger man and took most of his assets, his son was in prison, and when he went to his best friend's house for comfort and support, his best friend's wife essentially seduced him, and unknown to Bollea, the two of them were taping every encounter.

Bollea didn't know this until years later, when the video fell into Gawker Media's hands, and they published it. Not only did he learn in the worst way possible what his ex-best friend had done to him, but everyone accused him of being just another fading celebrity who'd released the video intentionally for publicity. And Bollea wasn't just taped having sex; he'd vented to his lover, said horrible things about his family in what he thought was intimate privacy, and most infamously, dropped a lot of n-bombs when talking about his daughter's boyfriend. When this came out, it essentially cost him what was left of his career.

Bollea was genuinely crushed by all these events. When he sued Gawker, though, he didn't really have a hope of winning. He wasn't nearly rich enough to take on the Gawker empire. Until Peter Thiel came along.

The ins and outs both of what preceded the Bollea lawsuit and what followed are truly a Machiavellian tale, because this really was a conspiracy. Bollea himself didn't know who the mysterious backer was who was pushing him to take his lawsuit all the way. Gawker was overconfident and would never have been destroyed this way had they known what was really behind the lawsuit; they assumed Bollea would eventually settle, because he had to. They made strategic errors that exposed them legally and financially because they didn't realize this wasn't a faux-outraged celebrity trying to get an apology, this was a billionaire trying to destroy them.

Enter GamerGate and the culture wars and then the 2016 election, and the judgment against Gawker became fraught with implications that went well beyond the politics of outing and whether or not it's okay to publish someone's sex video without their consent.

I listened to this book mostly because I was a bit curious about the story, but it turns out to be truly an epic of modern journalism, American culture, and yes, illustrative lessons in how real conspiracies work. While years from now, this story may become dated as a piece of history from this particular moment in time, I highly recommend it to anyone with any interest in contemporary politics, culture, journalism, Silicon Valley, celebrity media, or the mind of Peter Thiel.
Profile Image for Atila Iamarino.
411 reviews4,425 followers
December 29, 2020
Uma boa discussão sobre direito de expressão, informação na internet e acúmulo de poder de bilionários.

Ryan Holiday sabe contar uma narrativa intrigante, mesmo quando o tema não é tão polêmico assim. Neste livro, ele discute como se deu o processo da Gawker (rede que foi dona do Gizomodo, Jezebel e outros blogs) vs. o Hulk Rogan (com suporte financeiro do Peter Thiel). Uma disputa que envolve muito mais por trás.

Thiel havia sido exposto pelo Jezebel, mas não pôde fazer muito para tirar do ar o conteúdo, dado que o blog contou muito com o direito de "livre expressão" para publicar mesmo conteúdo falso. Mas, depois de se tornar bilionário, ficou atento a oportunidades de dar o troco e encontrou o Hogan a oportunidade de fazer esse estrago.

No fim, o livro se tornar uma discussão importante sobre responsabilidade, ética e conflitos de conteúdo em tempos de redes sociais. Ao mesmo tempo que mostra o estrago que uma pessoa com muito dinheiro pode fazer. Uma leitura bem importante para os dias de hoje. Acabei dando uma nota maior do que teria dado quando li pois o conteúdo continua na minha cabeça mais de um ano depois.
Author 7 books6 followers
March 22, 2018
An interesting yarn about an interesting case, even though Holiday does his best to make the book, like, really deep, man. Holiday is big into Stoicism, and boy does that show. Just about every chapter opens with a quote from Cicero, Marcus Aurelius, Machiavelli, Lucretius, Sun Tzu, blah blah blah. Basically, Holiday is trying to write a Deep Book filled with Deep Thoughts and spends pages and pages waxing rhapsodic about What Is Even A Conspiracy?

Why he'd choose that angle is beyond me, since the subject matter here is interesting enough, and you could fill a book just focusing on the personalities, of, you know, the people involved. Thiel, Denton, and Hogan are all fascinating characters, and you don't need to remind readers on every page that yes, you're a history buff, with random quote-drops from Greek poets.

The book isn't bad, but ultimately left me feeling dissatisfied, like I'd spend a bunch of money on a book that decided it needed to educate its readers on what a conspiracy is, what it isn't, and why that could possibly be important or relevant to this case. Spoiler: it's not. Everyone knows what a conspiracy is.
Profile Image for Paul Hambrick.
10 reviews1 follower
March 16, 2018
I've enjoyed other books by Ryan Holiday. I enjoy his stoic approach to things. He's a fascinating young man with an interesting, if not worldly, misguided insight into how things work.

This is his first bit of journalism. He does a good job investigating and telling the story about a real, honest to goodness conspiracy.

He leaves very few stones unturned and covers what happened very thoroughly.

The problem with this book is at the very end, he suddenly turns it into an opinion piece on his belief that the Trump presidency is a disaster and proves more and more a disaster every day that passes...

What??? Where did that come from? This book would have had to have been written in the final months of Trump's first year as President. How can he possibly conclude that it is a travesty?

I listened to the audio version of this book, and I must say, in the future, Holiday should hires someone to read it for him. He reads in a constant sing-songy decrescendo that gets more and more noticeable by the end of the book. His sentences are very short, which makes for an easy read, but makes for a difficult listen.

If you are interested in the nitty-gritty details of the take-down of Gawker, then read this book.

Otherwise, pass.
Profile Image for Raymond.
377 reviews284 followers
April 10, 2018
I liked the book. I think I would have liked it more had it focused on conspiracies in general and used the Gawker trial as one of many case studies. Holiday references other conspiracies in history which could have been given chapter treatments. And then he could have ended the book with why some conspiracies succeed or fail.
248 reviews13 followers
May 19, 2018
This is a work of non-fiction about the secret plot to take down gossip website Gawker, orchestrated by billionaire Peter Thiel. I did not like this book, which was disappointing since I heard a discussion of it on NPR that made me think it would be fabulous. I think there were a few things that irked me.

1) For some reason the author frequently writes in the present tense. For example (not a real quote, just to illustrate), "In 2012, Thiel goes to the store. He sees his rival, and debates what to say." Perhaps it's my historian bias, but this tense just seemed wrong and distracting.

2) Insufferable frequency of references to the "great MEN" (and there is not a single female agent in this entire book, by the way, unless you include a mostly absent Gawker exec or the woman in Hulk Hogan's sex tape) of history. This focus on a masculine "Great man" theory of history feels like a particularly antiquated way to deal with, oh, something hyper-contemporary like gossip websites. Also, the constant references to philosophy and the "anatomy" of conspiracy felt pretentious AF to me.

3) The author gets there in the end, but there was too much hand-wringing in my opinion about why people virulently reacted negatively once's Thiel's role in the Gawker takedown became revealed. Not that complicated...

That being said, it is a page turner. And, I will say I came away mildly more sympathetic to Thiel's motives in bringing suit.
Profile Image for Devogenes.
51 reviews22 followers
February 3, 2019
An interesting story told well except for rather ham-fisted insistence on framing it within the context of a grand-unified theory of conspiracies. At times I found the author to be almost obsequiously biased towards Thiel. When Mr.A is deceitful, it's sneaky and underhanded; when Thiel is deceitful it's brilliant strategy. When Denton and Gawker dehumanize people, it's callous and arrogant; when Thiel does it it's tactical genius.

It's also easy to forget, amongst all the quotes from Clausewitz and Machievelli and Sun Tzu, that this is a book about a hedge fund billionaire suing a tabloid and not a Tolstoyan grand historical narrative. Bit over the top is what I'm saying.

It is an interesting story though with complex implications. At the end I wound up roughly where I started, which is the general thought that all parties involved are more or less deplorable and that Gawker got what it deserved.
Profile Image for Sebastian Gebski.
1,036 reviews996 followers
August 7, 2022
This book is bad. Very BAD.

1. First of all, there's very little material for a book here. The story is far from complex, there are no twists, no complex plot - just enough material for a single article/blog post, not a book.
2. The words conspiracy appears here a LOT. Seriously, I've seen more sophisticated conspiracies in a grocery around the corner ...
3. The analysis of Gawker, Denton, and even Thiel - is very shallow; it feels like based on Internet gossip site articles instead of professional interviews and investigation (which Holiday claimed to do)
4. In the end, it was simply BORING.

(if you're wondering whether the rating was influenced by my private opinions on the case and its main actors:
* I think the American law system is utterly broken
* I hate sites like Gawker - I'm happy it went down
* I admire Thiel as an entrepreneur and non-conformist
* I don't associate myself with libertarians (quite the contrary)
)
Profile Image for Fabian.
405 reviews49 followers
December 13, 2020
Interesting for sure but lacks depth also one can’t find universal principles of conspiracies by examining one. The book gives courage to those who conspire for the greater good that I really liked other than a few lessons though it’s more a lengthy article. Maybe Ryan pumps out these books to fast and because of that their quality suffer.
Profile Image for LeahBethany.
605 reviews14 followers
September 29, 2023
Conspiracy was a fascinating tale. The author's writing style made it hard to establish a good reading flow but overall I enjoyed learning about the plan devised to take down Gawker.
Profile Image for Jenn Tesch.
54 reviews2 followers
March 9, 2019
Absorbing + fascinating, one of those tales that's impossible to believe is a true story. Ryan Holiday is so quotable throughout the entire book, little nuggets of wisdom on society, moral high ground/obligation, conspiracy, power, history, perspective, decency, wealth, the media, the legal process, strategy, psychology, war-- I bookmarked a few of my favorites. So much to learn from this book, I wish all nonfiction was written this way.

“We used to throw bombs, now we throw tantrums – or worse, tweets.”

"Perhaps we have too few conspiracies, not too many. Too little scheming, rather than too much. What would happen if more people took up plotting, coordinating how to eliminate what they believe are negative forces and obstacles, and tried to wield power in an attempt to change the world? We could almost always use more boldness, and less complacency.”

"Fights break out. Conspiracies brew.”

"Cunning and resources might win the war, but it’s the stories and the myths afterward that will determine who deserved to win it."

“The line from the Obamas was “When they go low, we go high.” It’s a dignified and impressive mantra, if only because for the most part, whether you liked them or not, it’s hard to deny that they followed it. But the now cliché remark should not be taken conclusively, for it makes one dangerous omission. It forgets that from time to time in life, we might have to take someone out behind the woodshed. How we have lost this. How squeamish we have become. We now blindly demonize what is often one of the most effective forms of action. How vulnerable this ignorance has made us to the few real conspiracies, successful or not, that exist in the world."
303 reviews217 followers
July 30, 2018
I've read every book Ryan has published. This one is different. If you'd put a billionaire VC, Some Machiavelli, Robert Greene strategy books, and a good law thriller into a shaker and shake long enough this book would come out.

The story is fascinating, conclusions are refreshing and an attempt to use those events as a long meditation about conspiracies, in general, is admirable.

Highly recommended.
Profile Image for John Temple.
Author 36 books85 followers
November 8, 2018
Intriguing and worthwhile story, but nearly every event was then explained and re-explained until the narrative suffocated under the weight of all the exposition and historical comparisons -- the present-tense was inexplicable too.
Profile Image for C.T. Phipps.
Author 78 books625 followers
January 16, 2019
After being outed to the public by Gawker and generally disgusted by their treatment of celebrity personal information (nude photos, sex tapes, innuendo, and some genuinely good reporting like Bill Cosby's sexual assaults)--Peter Thiel, founder of Paypal, gave a blank check to a group of lawyers to find cases against the media outlet. Even if you never read Gawker's sleazy coverage, you probably have visited its former sites like Kotaku. Thiel's hatchet team discovers the perfect case in Hulk Hogan who as a sex tape filmed without his consent by his best friend of him having sex with said friend's wife (apparently with said friend's blessing). What follows is a legal battle that lasts years, bankrupts Gawker, and thrusts Thiel in the limelight after he reveals he arranged this.

Ryan Holliday frames this story, which isn't much more convoluted than Thiel agreeing to pay for the legal fees of his enemies, in mythic terms. It's very entertaining but not much of a conspiracy.
Profile Image for Christine.
6,835 reviews521 followers
August 3, 2019
On one hand, I really think everyone should read this simply because it does address what is, to me, the unanswerable questions that freedom of speech raises (and I much rather have freedom of speech than not).

Yet, the book starts at good and then you start wonder.

For instance, Holiday seems far, far more sympathetic to Thiel, which is understandable, but the sympathy is very obvious which undermines the unbias slant the book seems to want to have.

Or, there is the almost complete glossing over of Gamergate. Yes, it was a domestic drama that blown up, but the unsavory and sexist aspects of it are totally disregarded. It wasn't simply an attack on the press as Holiday almost seems to want to make it.

And there is his writing style, which you are either going to love or hate. It's one of those styles.

Still, I really do think you should read this book.
Profile Image for Rowdy Roddick.
18 reviews
March 29, 2018
How far would you go to exact revenge? In "Conspiracy", author Ryan Holiday details the lengths that notorious Silicon Valley venture capitalist Peter Thiel went to achieve the complete destruction of the media conglomerate Gawker after the website published a story outing him as gay in 2007, a personal matter that Thiel preferred to keep private. Waiting nearly 10 years for the perfect opportunity to strike back, Thiel finds an unlikely ally in the way of former pro wrestler Hulk Hogan, who becomes embroiled in a personal public exposure of his own when Gawker posts a video of him having sexual relations with his best friend's wife in 2012. Not knowing who is behind the mask, Hogan throws his trust behind the legal team and strategists that Thiel is able to assemble to completely shut down Gawker through a high profile court case in 2016, leaving the website bankrupt and its owner, Nick Denten, morally defeated.

Holiday profiles this entire ordeal in such a suspenseful manner that its almost impossible to put down. One of the surprising elements of his writing here is he is able to take into account the different perspectives of all involved; the moral quandry of Gawker's invasion of privacy is obviously front and center, but Holiday also explores the issues of racist comments made by Hogan that surface in the middle of the trial, the ethics behind Thiel's use of personal funds to destroy a media company that was publishing content he didn't agree with, and the backbone of Gawker's legal defense from the very beginning: that the first amendement (free speech) trumps the fourth amendment (a person's right to privacy). All perspectives are given their equal share in this account, and though its hard not to root for Hogan and Thiel as the aggrieved underdogs, one can't help but come to some degree of empathy with the Gawker empire and Denten's philosophy by the end as well. By lending all players in the game an equal soapbox to express their views, I feel this book does a great job of making you think over the complexities of the issue, from both a legal and moral perspective, long after the last page has been turned.

Towards the end of the story, Holiday makes a point that we often look at large obstacles, change in the world we would like to see, but don't take any concrete steps to achieve action because we don't take the time to plan out what steps we would need to take to get from Point A to Point B. Although Thiel had hundreds of millions of dollars in funds he was willing to spare, he was discouraged from the very beginning by the sheer power that Gawker had over all who had tried to go after them in the past via legal action. However, with patience, strategy and discipline, he was able to strike at the right time and realize his mission of destroying a corner of the internet that refused to acknowledge one's right to privacy. With a story like that it's impossible for the reader not to feel inspired to want to start a conspiracy of their own.
62 reviews6 followers
January 26, 2020
I was tempted to give this book a one star rating, but it was kind of an entertaining page turner so I gave it two stars, even though I'm not sure it deserves the second star.

My main problem with this book is that it Ryan Holiday wrote a love letter to the moral monster known as Peter Thiel in the form of this book, without giving a clear picture of who Peter Theil really is. Ryan Holiday will make references to Peter Thiel being a libertarian and having "unconventional ideas" but he never comes out and says what these unconventional ideas actually are. Holiday has neglected to mention that Thiel holds opinions such as apartheid should be brought back, women shouldn't be allowed to vote, and that democracy is evil. Thiel is also tied to a bunch of vile white supremacist/alt right figures through his involvement in the neo-reactionaries/dark enlightenment movement. He's also a champion of the ridiculous sea steading movement, which is an attempt by billionaires to build floating cities outside of international borders in order to keep their money out of the reach of governments. This book presents Thiel as kind of an avenging superhero, and Gawker as the bad guys who wronged him for no reason. However, how would the readers of this book feel about Peter Thiel's glorious victory if they knew that he's a straight up white supremacist? Why did the author write a whole book about this tech-nazi and just neglect this side of Peter Thiel? You have to wonder if at worst, Ryan Holiday must be in agreement with Thiel's white supremacists ideas himself, or at best, he must just be a fascist bootlicker.

Another thing I really hated about this book is it was swimming in annoying references to Machiavelli and Sun Tzu. References to these two historic ding dongs are what all bad writers use when they want to make some fascist dipshit sound wicked smart. When the author wasn't making references to Machiavelli or Sun Tzu he was comparing Peter Thiel to lots of other great men of history, and none of this added anything to the book. It was just an annoying distraction to be taken out of the main narrative and have to read about Peter Thiel being compared to some Roman emperor or World War 1 general every five pages or so.

I wasn't a fan of Gawker for the most part, and it's possible there should have been some regulation in regards to their most slanderous stories, but I don't really think that a billionaire fascist crushing a media outlet is a good thing. The author also talks about how he wishes that there were more conspiracies, but you would also have to possess the massive wealth that Peter Thiel does to do anything remotely similar to what he did to Gawker. Is Ryan Holiday just asking the ruling class to just stomp everything out of existence that they don't like? It seems like he is.
Profile Image for George.
72 reviews16 followers
February 10, 2021
I doubt I'd have bothered with this book if it didn't have "Ryan Holiday" on the cover. I mean, can the story of Hulk Hogan suing Gawker really be that interesting? Who is the target audience - the intersection of "people who are fans of Hulk Hogan" and "people who know how to read"? But Holiday said it was his favourite thing he'd ever written, so I gave it a chance... and the response is a resounding "meh".

Conspiracy isn't terrible; it's as well-written as anything from Mr. Holiday, and I suppose someone needed to document the full story of this unusual lawsuit. It was also interesting to get a closer look inside the mind of Peter Thiel, that most contrarian of billionaires. I certainly have no sympathy for Gawker Media; it and its successors were and are toxic cesspools staffed by evil monsters and I'd celebrate if everyone who ever worked there got incinerated in a fire, preferably one at the Twitter office party, but I knew that before I read the book.

Conspiracy was entertaining enough to keep me reading to the end, but there's a whiff of ridiculousness about the whole thing. Holiday fills the pages with historical analogies, philosophising at length about the nature of conspiracies and relating Hogan's antics to all manner of Machievallian machinations going back as far as Ancient Rome, and it's not boring, but at the end of the day the framing device for all this erudition is still the story of a has-been Spandex-wearer shagging his friend's wife on camera then suing a gossip website. This ain't the Gunpowder Plot.

And while Holiday downplays it, it's pretty clear that, fundamentally, Hogan et al. won not because of any particularly ingenious legal manoeuvring, but because they simply had deeper pockets than the bad guys. That's the American legal system: the richest man wins, and you don't fuck with billionaires. Case closed.

Thiel's free to fund whatever lawsuits he likes - as Holiday points out, rich people do this kind of thing all the time - but one question Conspiracy leaves woefully unexplored is why things have to work like this at all. Maybe one day we'll live in a world where our finest legal minds have more important things to worry about than a wrestler's sex tape, where the disadvantaged can seek justice without needing the help of a sympathetic billionaire, or where the charitable donations of the ultra-wealthy go to more worthy causes than the settling of feuds between rich, high-status celebrities, but sadly we live in the imperfect present. One might be tempted to think that a small group of people could fix this picture if they got together and plotted, but I'm not big on conspiracy theories.
Profile Image for Eperdu.
305 reviews3 followers
March 20, 2018
Another great read ...

I’ve long been a fan of Ryan Holiday, so take that for what it’s worth, but I believe this to be yet another book that seeks to enlighten and educate.

I was understandably confused when I learned that his latest book was about Hulk Hogan, Gawker, and Peter Thiel. It seemed really strange to me. I didn’t immediately pre-order it, I waited. I had to know, why this book, why this story? After release, the reviews and thoughts began trickling out and I knew I had to read the story.

Ultimately it’s not about the key players, it’s about our history and the history of conspiracy, as an act. It’s a story of a modern day conspiracy and the players happen to be Hulk Hogan, Gawker, and Peter Thiel. But it’s more than that. It’s about our world and our current landscape, political and social.

It gave me insights into a few questions I’d had in the past year and it also gave me a lot to think about (and an even larger stack of books to read!).

Ryan is always engaging and easy to read, he uses quotes liberally which is refreshing and often “cheating” at writing, but it works well for the things he’s trying to convey.

Profile Image for Ramón Nogueras Pérez.
610 reviews304 followers
August 2, 2020
Un libro interesante y bien escrito sobre cómo un billonario se venga de un periodista y el medio que dirige, y donde todos acaban siendo detestables. Hay que decir en favor del autor que narra los hechos con una imparcialidad casi total, aunque a veces patina un poco en favor de dar ciertos dilemas como resueltos cuando no, no lo están.

Me parece una lectura tan interesante e ilustrativa como Trust me, I'm lying, y lo complementa perfectamente. Un gran libro para entender algo mejor cómo funciona esta Internet y estos medios que nos hemos dado, y la enorme farsa que es el libertarianismo que los billonarios dicen perseguir. Lo recomiendo muy fuerte.
March 13, 2018
Next to the really crazy story this might be Ryan Holiday's best written book up to date. The tone of voice and neutrality through which he communicates the story really add to the whole experience and truly get you sucked into the story.
Profile Image for Heraa.
52 reviews3 followers
August 8, 2020
This book was an account of the conspiracy Peter Thiel spearheaded to take down Gawker Media after a blog post that outed him in 2007. There is no good guy to root for here — Gawker was a callous gossip site that encouraged bullying, published sex tapes, and delighted in its negative press. Peter Thiel, on the other hand, is a tech billionaire who went on to support Trump after masterminding the lawsuit that brought down Gawker. Is it unethical for a man with endless funds to exact revenge on a media site for outing him? Is it worth defending a media company that posted (and refused to take down) a secretly-recorded celebrity sex tape because of its “newsworthiness”? And then there is the man Peter Thiel was funding to sue Gawker: Hulk Hogan, a pro wrestler who is caught on tape self-proclaiming that he’s “a little racist” before hatefully saying the n-word in regards to his daughter’s boyfriend. There are no heroes here.

However, it can’t be denied that the events that transpired are fascinating, as well as chilling. Peter Thiel spent ten years trying to take down Nick Denton, the founder of Gawker, and he almost pulled it off in secret — it makes one wonder what other conspiracies are out there that have yet to be uncovered.

The facts in this book are well-reported, even if the author spent a bit too much time quoting Machiavelli and Shakespeare and referencing various conspiracies in history for my taste. This is definitely a solid read.
Profile Image for Nadia.
130 reviews36 followers
July 30, 2019
Moods: informative, reflective
Pace: Medium

Strong character development? It's complicated
Loveable characters? No
Diverse cast of characters? No
Flaws of characters centre-stage? Yes

I thought there'd be a lot more drama and action in this book than there was.

While there certainly was intrigue, I did find the pace slower than I expected, especially with Ryan Holiday re-iterating multiple times the ideas around conspiracies and what happens when people feel wronged/vengeful, rather than focusing on the details of the story.

The book's narrative does take an interesting turn into politics and aims to inspire people to take action during those times when they want to but feel they can do nothing about a certain situation — however, it fell short for me in being wholly inspiring.

It does succeed in being reflective though — causing you to think: is it ever right to seek revenge when you've been hurt? Is it right to destroy an individual or institution that you think is incredibly damaging or hurtful to a wide range of people? The word 'conspiracy' tends to be viewed as automatically 'bad', but Ryan forces his reader to question that. Ultimately, I remain unconvinced with Ryan's hypothesis that we need more conspiracies in the world than we currently have.

There were a handful of extracts that were motivating with regards to my work. Turns out there are quite a few similarities between running a startup and pulling together a conspiracy.
Profile Image for MM Suarez.
671 reviews54 followers
January 6, 2021
Audiobook narrated by Ryan Holiday (author) 11hrs 39 mins

No matter what side of a First Amendment argument you fall under this author does a very entertaining job of telling this crazy but true story. I heard about this case back when these events took place but was not fully aware of how it all came about, after reading this book and looking at our world these many years later, I am not at all convinced that this case taught anyone any "lessons" if anything things have gotten worse!

The author does a competent job of narrating but sounds somewhat monotone at times, could have been done better by a professional narrator.
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