Hey reddit, my name is Ryan Holiday.

I’ve spent the last year and a half piecing together billionaire Peter Thiel’s decade long quest to destroy the media outlet Gawker. It was one of the most insane--and successful--secret plots in recent memory. I’ve been interested in the case since it began, but it wasn’t until I got a chance to interview both Peter Thiel, Gawker’s founder Nick Denton, Hulk Hogan, Charles Harder (the lawyer) et al that I felt I could tell the full story. The result is my newest book Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

When I started researching the 25,000 pages of legal documents and conducting interviews with all the key players, I learned a lot of the most interesting details of this conspiracy were left out of all previous coverage. Like the fact the secret weapon of the case was a 26 year old man known “Mr. A.” Or the various legal tactics employed by Peter’s team. Or Thiel ‘fanning the flames’ of #Gamergate. Sorry I'm getting carried away...

I wrote this story because beyond touching on many of our most urgent issues (privacy, media, the power of money), it is a timely reminder that things are rarely as they seem on the surface. Peter would tell me in one of our interviews people look down on conspiracies because we're so cynical we no longer believe in strong claims of human agency or the individual's ability to create change (for good or bad). It's a depressing thought. At the very least, this story is a reminder that that cynicism is premature...or at least naive.

Conspiracy is my eighth book. My past books include The Obstacle Is The Way, Ego Is The Enemy, The Daily Stoic, Trust Me, I’m Lying, and Growth Hacker Marketing. Outside writing I run a marketing agency, Brass Check, and tend to (way too many) animals on my ranch outside Austin.

I’m excited to be here today and answer whatever reddit has on its mind!

Edit: More proof https://twitter.com/RyanHoliday/status/973602965352341504

Edit: Are you guys having trouble seeing new questions as they come in? I can't seem to see them...

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For people who know the story of Gawker and Thiel, what additional value does the book provide? What was the most interesting thing you learned about the case when writing the book?


To me, this story is not just the story of a ten year revenge plot, it's really the story of all conspiracies. You know we live in this world of conspiracy theories (I happen to live in Austin, the hometown of Alex Jones) but few actual conspiracies. But any student of history knows that the world often pivots on something a few people cooked up in secret. So to me, this book was a chance to tell that larger story. The fact that Thiel was willing to go on the record and explain his process was, in my view as an author, an unprecedented chance to lay out how power really works in a way that few have been able to before. It's ironic, Gawker's informal motto was that they showed "How Things Work"--the story behind the story. But in this case, they missed what was actually happening. So did everyone in the media. What I tried to do here was step back, take judgment out of the picture, and show what went down and why.


The fact that Thiel was willing to go on the record and explain his process was, in my view as an author, an unprecedented chance to lay out how power really works in a way that few have been able to before.



Do you think that Thiel chose Hogan precisely because he knew that the whole "isn't this hogan sex tape gawker court room scene just hilarious" aspect would overshadow his involvement to an extend? I mean, if it was just some random dude who sued gawker over something much less spicey maybe the public story would've been all about "how things work" when it comes to the incredibly powerful


The fact that Thiel was willing to go on the record and explain his process was, in my view as an author, an unprecedented chance to lay out how power really works in a way that few have been able to before

can you describe in one sentence how freaking out of your mind you were when you first found out he agreed to a full interview?


Although this story is fascinating, I’m not sure I’m convinced on the “conspiracy” element that you are selling here

It’s simply a very intersting legal case,


Did it ever come out who leaked Bubba’s video? I live in Florida and used to listen and it was heavily implied that the video originally came from one of his cohosts.


The police reports, which you can pull out from the trial documents off the website of the Pinellas County Courthouse, suspected that the tapes were leaked by a rival radio DJ Matt 'Spiceboy' Loyd. He was never charged with the crime so we should be careful about pointing fingers, but as far as a best guess goes from both the FBI and the Tampa Police, that's it. Even weirder--weirder than this entire dispute being put into motion by a fight between two shock jocks--is that the lawyer who represented the brokering of the sales of the tape was a man named Keith M. Davidson, who later came to represent Stormy Daniels after her alleged affair with the man who is now the President of the United States of America...

Edit: article here about that insane set of circumstances.


That’s the name I had heard as a primary, thanks for replying.


Hmmm... so will Keith Davidson feature again in your next book? I hope so.


Wasn't Spiceboy an ex employee of Bubba? In fact, didn't Bubba give him that name?


Where would you rank Hogan slamming Andre the Giant at Wreslemania 3, in front of 900,000+ screaming Hulkamaniacs, among the greatest moments in human history?


Somewhere around that moment in 1998, when The Undertaker threw Mankind off Hell In A Cell, and plummeted 16 ft through an announcer’s table.


You’re better than this, please come up with your own schtick.


I don't care how weird/conspiratorial this whole thing was, but after Hulk was taken to the goddamn cleaners by his ex, getting him some money back feels right to me.


To be fair, the lawsuit from his son's car accident wrecked him far more than his wife did. Don't get me wrong, she wrecked him too; but his finances were a mess before the divorce.


How bad did she wreck him?


Probably hiding under a door frame to protect himself from the earthquake caused by the Giant's fall, brother


My user name being relevant to a front page post is one of the greatest moments in human history IMHO


How did you convince both Peter Thiel and Nick Denton to talk to you for this book?


I'm not sure I convinced them, so much as the fates aligned. I happened to get an unsolicited email from Thiel in late 2016--he had read some of my Gawker columns and suggested we get dinner sometime. I got an email from Denton not long after saying he'd read some of my philosophical writing and wanted to know if I wanted to get together. That I was talking to both of them I think was intriguing to them both, and also meant the other would want to keep talking for fear that the project might be too heavily weighted by one side. I also kept the project's direction really open for a long time--was it a book about media or technology or these two characters or was it about revenge? I really didn't know, but that allowed me to ask about a wide range of things so it never felt super invasive or "gotcha"-y. Denton preferred to do his interviews over chat, so our process was also much less of an imposition. Meanwhile, I think Thiel is quite proud of what he had accomplished and was tired of the very biased reporting around it.


You sound like a good journalist :)


In what way did Peter Thiel surprise you the most?


I thought he would seem much more angry than he ended up seeming. I spent enough time with him that if that had been the primary motivation, I think the mask would have slipped--if only for a second. Instead, he seemed very calm, very detached, very strategic about the whole thing.

The other interesting part of Thiel's personality is that he uses the steel man technique when arguing or explaining a complicated issue. This surprised me given that he had taken to calling Gawker terrorists and such. But really, he was always very open-minded when it came to discussing things. For instance, if you ask Thiel a question—about Gawker or Trump or whatever—he doesn't just pull up some half-formed opinion. Instead, he begins with, “One view of these things is that . . . ,” and then proceeds to explain the exact opposite of what he happens to personally believe. Only after he has finished, with complete sincerity and deference, describing how most people think about the issue, will he then give you his opinion, which almost always happens to be something radically unorthodox—all of it punctuated with liberal pauses to consider what he is saying as he is saying it. Even when he does describe his opinion, he prefaces it with “I tend to think . . .” or “It’s always this question of . . . ,” as if what he is about to tell you is simply capturing where his opinion falls the majority of the time when running a thought exercise on the topic, as if he is always in the process of deciding what he thinks. I found that to be very impressive and unusual. It was hard to be a lazy thinker around him.


TIL about the Steel Man technique


Mr. Thiel is a chess prodigy, I'm sure he meticulously thought out his next three moves before he made them.


I try to employ that kind of technique when talking about an important issue to me. Its a strong way of having real discussion and debate today, especially since we are so used to being stuck in bubbles and having to defend our own position outright


as if he is always in the process of deciding what he thinks

This reads a little like Tolkien for some reason. It sounds like a way to describe a Hobbit smoking a pipe haha


One of the narratives about the Hogan/Gawker/Thiel saga has been, in its distilled form: Since Peter Thiel's financial resources far outpaced Gawker's, he shut down the company (personally, I see it as more nuanced, but fair enough). Then the narrative goes on to talk about how dangerous this is for journalism. What's your take? Is Thiel's involvement in this case an inauspicious omen for journalism? Does Thiel himself reveal any kind of dislike for the free press? Any predictions for how this case will be impacting the media ecosystem 5-10 years from now?


The central question of this story to me is, who was the bully? Was Thiel the bully or was it Gawker? Was Peter the billionaire who destroyed a millionaire? Or was he a righteous man who attempted to use his money to solve a problem that only power and money could solve? Was it the media outlet that thoughtlessly outed a then-mostly unknown tech investor? Or was it the billionaire who spent millions plotting against him for it? Was it the website who loved to out gay men or was it the team who would back Trump in the 2016 election, and in the case of Charles Harder, write an 11 page letter threatening to sue Michael Wolff for his book about Trump? Was it Denton who never apologized, who ignored judicial orders or was it Thiel, who never showed his face until after his revenge was complete?

It depends on where you sit, but one thing that has been lost in the coverage since the verdict: Gawker thought they were winning until suddenly, they lost. It was Gawker who had filed endless motions and appeals, who had fought Hulk Hogan with scorched earth tactics, and never apologized for obtaining an illegally recorded sextape and publishing it for more than seven million people to gawk at (and then spent $10M+ vigorously insisting it was right to do so). There was a moment in mid-2014, when Gawker’s lawyers threatened Hulk Hogan, telling him that it was his last chance to drop the case before they went after him for attorney’s fees. More than anything, what the jury and the judge reacted to had been their arrogance. The verdict reflected that.

Nick Denton told me, “The idea that Thiel was terrified of the next Gawker piece is still absurd to me—and given how things turned out, we had much more to fear from him than the other way around." But it wasn’t that absurd at the time, when they were a website with hundreds of millions of readers, when Gawker was the site that had never been challenged in court and published whatever it wanted, Thiel believed that Gawker’s power was partly in pretending that it was more powerful than it was. Now that they're gone...it looks different.

As for who is the bully now? As I said, backing Trump and some of the clients Charles Harder has taken on since give me pause...but that doesn't have the power to rewrite where things were in 2007.


I’m going to buy your book based on how well-written your replies are in this thread. Great job. Looking forward to reading it tonight.

Edit: Just bought it on kindle!


I can't muster sympathy for gawker. They were told by a judge that the original video was too much and they could report on the issue but not invade a man's privacy like that. All other sites conformed to the court order. But gawker defied it thinking they had the right to show a man that hadn't consented to a sex tape being public.


t was Gawker who had filed endless motions and appeals, who had fought Hulk Hogan with scorched earth tactics, and never apologized for obtaining an illegally recorded sextape and publishing it for more than seven million people to gawk at (and then spent $10M+ vigorously insisting it was right to do so).

Really wish this one thing hadn't been lost in the coverage. I have no love for Peter Thiel or his politics, but at the end of the day, Gawker did a stupendously shitty thing, then doubled down on it, throwing their journalistic credibility right out the window. If they didn't want to get sued into oblivion, they maybe shouldn't have opened the door for it.


More than anything, what the jury and the judge reacted to had been their arrogance

They reacted more to Gawker's arrogance than the facts of the case?


Its funny to me when people refer to Gawker as journalism.



This isn’t a super rich guy pulling down the New York Times. It’s a super rich guy destroying the Enquirer.

The world is literally a better place with less Gawker.


Hi Ryan,

I loved your appearance on The Biggest Problem in the Universe, which was 3.5 years ago now. Your problem, Outrage Porn, was great and was rightfully voted to #10 biggest problem on the list.

Since you like researching lawsuits, are you aware of the lawsuit that is going on right now between the two hosts of that show, Maddox and Dick Masterson? What are your thoughts on the suit?


Hi Ryan, What on earth did you do to elicit this twitter reaction?



I have no idea. Media twitter is a black hole of humanity. It explains the mess we're in more than reporters would like to admit, I think.


The real answer should be "who cares?"


She's ex-Gizmodo, which was a Gawker property (and is now the holding company of Univision for the surviving non-toxic assets).

Many of the old Gawker Media staff are still extremely angry about this and believe that they and Denton did utterly nothing wrong during his reign. Probably the most infamous post by a number of staff reflecting this attitude was during the Geithner debacle, when their concern wasn't what led to a particularly ill-researched and sickening article outing him which got shredded by outside observers and commentators - but that corporate had dared to interfere with their journalism and take it down.

Don't remember off the top of my head if she was part of that, but wouldn't surprise me.


Because obviously if you're not supportive of Gawker without question you're against us /s


I don't understand how anyone can defend Gawker when by any measure of moral and legal law they were in the wrong?

I always think if Gawker leaked an older woman's sex tape, despite her public protests, the initial media reaction would have been the opposite.


I wrote for a Gawker-owned site for three years and I was glad to see them die out.


I think she's harkening back his first book, Trust me, I'm lying, where he illustrated how click bait sites like Gawker manufacture news


Her profile picture screams crazy


Agreed. That and the fact that her latest tweet says she's leaving journalism to start work at Microsoft, but thinks it's ok to tell some random author to "fuck off," doesn't scream stable to me. If I publicly told someone to Fuck off on social media I wouldn't have a job tomorrow.


She explains it in the following replies. Basically his book.


Did anyone at Gawker ever address the hypocrisy of posting the Hogan tape while Jezebel made a huge deal over the celebrity nude leaks?


I address it in the book.

“Gawker is not in the business of holding back information,” Gawker’s managing editor, Emma Carmichael, would later say in her deposition. If they got it, they ran it. A Gawker writer would defend a similar story a few years later by saying, “Stories don’t need an upside. Not everyone has to feel good about the truth. If it’s true, you publish.” These people had come to believe that “truth” was the governing criterion, and that the right to publish these stories was absolute. As far as their experience was concerned, they were correct: There had never been serious consequences. They had called every bluff. They had published what every other media outlet would have deemed unpublishable and not only walked away from it—the audience loved them for it.

Of course they knew that running stolen footage of a naked person was not exactly right. Jezebel, a Gawker site, had made a name for itself defending women against every kind of slight, defending their rights to privacy, defending them against men who tried to victimize or bully them online. Jezebel would define its views more clearly in outrage over a rival blog that published a controversial story about someone’s sexuality: “Don’t out someone who doesn’t want to be out. The end. Everyone has a right to privacy. . . .” Except Peter Thiel, and now Terry Bollea, apparently.

Less than two months before the Hogan piece, a Gawker writer who would later become the site’s editor writes a piece condemning the rise of “fusking”—the practice of stealing photos from online accounts and posting them. In it, he rejects any attempt to blame the victim, or any excuses made for the “behavior of thieves and creeps” when they steal people’s private things. Gawker had seen the anger and outrage about Hunter Moore when it had written about him and his media site built around so-called revenge porn. Commenters even cheered when Gawker reported that the FBI was investigating Moore. Yet when that tape arrived to its SoHo offices, Gawker would twiddle it down to a highlight reel and run that naked video of Hulk Hogan in front of an audience that numbers in the millions—a video not just of Hogan, but also of the woman he was filmed having sex with, who also had not consented to its publication. Gawker would promote it to their Facebook fans: “It’s probably time you watched this snippet from the Hulk Hogan sex tape with a woman some claim is Bubba the Love Sponge’s wife. Work’s over. You’re fine.”


Hi Ryan. Do you think it's better for a marketer to be a generalist with a broad knowledge across a number of disciplines, or be highly specialized in one?

And do you ever think you'll turn your hand to fiction writing?


I suppose that depends on who you want to be and what kind of career you want to have. Personally, I think it's best to be really good at 3-4 distinct things. This was you have different competencies you can expand or contract based on need, the market, interest, etc. But that's still small enough to develop a solid reputation for excellence in. If you're good at 500 things (if that's even possible) it's hard for people to understand what you do.

Basically, I'd rather be Bo Jackson than Ashton Eaton.


Bo knows this and Bo knows that, but Bo dont know know Jack, cuz Bo don't rap.

-tribe called quest


Hey Ryan, I am always blown away by how much you seem to accomplish in such a short amount of time, while juggling media appearances, your own company, a farm, and a baby (congrats!). My question is, what does your "ideal day" look like when you're busy writing a book?


I think about this one a lot. It's never exactly how I want it to be but usually

  • Wake up early
  • Take the baby for a long walk
  • Journal for a few minutes
  • Write/work until breakfast
  • Write/work after until noon or so
  • Lunch
  • Phone calls/biz stuff
  • Long run or swim
  • Work a bit more
  • Try to be home by early evening to have dinner with wife and kid
  • Put kid to bed
  • Read/watch TV with wife
  • Journal before bed
  • Sleep 8+ hours

I feel exhausted after the 1st bullet point. Well done, sir.


What is the journal entry in the morning for? Are you setting goals?

Or are you saying you're reading the news?


Does that generally add up to 8 hours of work per day?


Hi Ryan, I'm a huge fan of your work and just finished up Conspiracy last week. I had two questions for you if you'll excuse my greed:

1) What tenet of Stoicism do you find most difficult to practice in your own life?

2) Given that Conspiracy is a departure from your previous works, what unique challenges did you face while writing it?


The truth is all of Stoicism is easy to say, difficult to practice. I think one of the harder ones for me is just not letting my temper or my impulse to react drive my behavior. To me, the Stoic is someone who is deliberate about what they do and say, just part of my personality is to be intense and always do, do, doing. Someone says something, I want to respond. There's an opportunity, I want to take it. There's something that needs to be fixed, I want to fix it. Someone makes an argument, I want to argue back. The problem there is that I'd be better off if I paused and really thought about the best response or whether a response was necessary or not. I would save myself trouble, heartache, frustration, etc if I could do this better. When I look at my journal entries, I tend to find this issue--or something related to it--is central to most of what I am struggling with or having problems with.


If you could meet Marcus Aurelius what would you do and what would you ask him?


"Wait, I thought you died?"


I feel like I missed an opportunity by not just answering with this gif.



How many times did you watch the footage?


What do you think about Maddox's lawsuit against me, Patreon, and several comedians who work for my show (The Dick Show) and their real-life employers for $20 million dollars over Maddox's hurt feelings?

Did you know Maddox's girlfriend Mental Jess has a restraining order for calling people's jobs in an attempt to get them fired? What role do you think Maddox played in that?

Last question, are you morally complicit in Maddox's lawsuit and lynch mob tactics by promoting him and appearing on his show?


In your opinion, what does this case and the bankruptcy of Gawker mean for the future of "free press?"


Look Gawker has been gone for almost two years now. If anything, you could make an argument that we're in a golden age of investigative reporting. The Harvey Weinstein scandals, the reporting on Trump, etc.


I would argue that it's not that we're in a golden age of investigative reporting, it's that we're in a golden age of information dissemination and utilization. Harvey Weinstein was well-known in Hollywood for being a total dirtbag, but the story wouldn't have had the same amount of legs if it wasn't right at peoples fingertips the second it broke, and it certainly wouldn't have been as impactful if it had been told exclusively on printed pages; at that point it would have been relegated to water-cooler chat and forgotten about in a week or two. Social media boosted and changed that one story into an entire movement.


With news outlets actively lying/slanting stories like it's their job, we don't need outlets like Gawker.


What's the weirdest thing you've read in a book by the likes of Seneca or Marcus Aurelius? Those dudes came from different cultures.


I mean a few pages into Marcus's Meditations he congratulates himself for never laying a hand on his female slaves (that is rape them) so that's a pretty good reminder that these guys lived in a different culture. Rome was a dark, violent, twisted place. We can't forget that while some aspects of their lives were shockingly identical to ours--almost as if no time has passed--others are just insanely incomprehensible. I believe the punishment for parricide in Rome (killing your parents) was they would put you in a thick leather sack with a dog, a cat, a snake and a monkey and then throw you in a river to drown and be clawed to death.


Those were the days


There's a great China Miéville story about that last bit, actually.


I believe the punishment for parricide in Rome (killing your parents) was they would put you in a thick leather sack with a dog, a cat, a snake and a monkey and then throw you in a river to drown and be clawed to death.

I wonder how easy it was to get hold of those things in ancient Rome? And if so, were they acquired specifically for that punishment?


I think one of the weirdest things I've seen was when AJ Daulerio joked around during a taped deposition about drawing the line at publishing a sex tape if the celebrity was under the age of four.

Do you get the sense that many people and institutions still shoot themselves in the foot this spectacularly on the regular? One would think with the advent of social media people would become more wary of saying completely stupid things.

Have you ever been present for one of these moments where you thought "I absolutely cannot believe I just heard that."?


That moment when he was confronted about his stupid "joke" was one of the best moments of the trial.


There's no question that that comment, made in a deposition in late 2013, turned out to be catastrophic to Gawker three years later when the case was put in front of a juror. The chapter that I tell that story in in the book is about why you need to both know yourself and your enemy (borrowing from the concept by Sun Tzu). Gawker both had no idea the enemy they'd made in Thiel, had no real understand of how committed Hogan would be and worse, they did not understand how they might come off in court. The result was that they did and said things that came back to haunt them when their fate rested in the hands of some ordinary people in Florida.


How much money do you estimate Peter Thiel spent backing Hogan?


Between $10-$20 million is the estimate.


Did Hogan give Thiel any of the $140 mil?


That’s a damn good investment.


You're not a journalist, yet you wrote in this investigative report in your typical style drawing from history/prior works. Did you ever feel you were stretching to craft a narrative, for example seeing the book on ancient strategy on Theil's desk? Or were their things said in the interviews that lent themselves to the way you crafted the "story?'


It really was insane to see Discourses on Livy on Thiel's shelf in his apartment (not his desk), given that I had just read it as research for the book. And for him to be able to reference the section from memory was just one of those things that made this feel somewhat meant to be. The other funny anecdote is that he gave me a copy of The Fifteen Decisive Battles of the World thinking it was this obscure text that would make me realize what he had tried to do...and it happened that I'd already read it a few years before and had recently pulled my notes from it to see where there might be some insights for this book.

As for stretching to craft a narrative, I would say that the weird thing about the book was that there was actually too much material so instead of stretching the difficulty (or the shaping) came more from what not to include. A question above asked about who leaked the tapes, my decision to make this book about a conspiracies meant that the leakers identity was a lot less important, so it was left on the cutting room floor.

Your question is good though. Authors, journalists, lawyers--we're all telling stories and stories require choices and as a result certain things are obscured or emphasized to the reader. But I think this is better than say me dumping all the legal documents on you and saying: You figure it out. I mean, that's what I'm being paid to do.


Did you get to meet Hulk Hogan? Is he as awesome as I thought of him while growing up? I loved Hulk Hogan and have always wanted to meet him.

Could you have him call me if you're in contact?! It'd make my year, easily!


I did interview Terry Bollea for the book. It was a surreal experience. He showed up in a shirt with his own face on it. I found him to be surprisingly tender and sweet (I actually had the same reaction to Nick and A.J). In any case, Terry deeply believes he did a public service here. He's also quite religious and believes this was all part of plan that God had for him.


He's also quite religious and believes this was all part of plan that God had for him.

Did you ask him if sleeping with his friend's wife part of God's plan for him?

Edit: I wish I could reply to everyone, so I'll just say it here. My intent in saying that was not to condemn a man for [what could be considered] hypocrisy, but rather to test the theological ramifications of his logic. The way I see it, claiming providence like Hulk did (and many other instances by people throughout history) is a pious vanity. By observing discrepancies in this particular claim I am inviting people to change their approach to assessing their lives.


Do you see yourself as a bit of a monumental hypocrite in that you wrote the book confessions of a media manipulator (how you seeded news) and yet you were vigorously anti-gamergate when it was gawker et al in collaboration with some prominent social justice advocates they were banging that actually turned the fight for transparency in gaming journalism into a ideological shitshow?

The real funny to me is that you ended up coming round to my counterculture position and pretending you never thought any differently. Would that be what media manipulators do?



I really enjoyed "Trust Me...", but, since I read it in 2017, it already felt way out of date and all your anecdotes and projections seemed to underestimate what media manipulation via viral sharing could do (e.g. swing an election). Are you tempted to do a second edition where you provide some insider knowledge to these kinds of bigger and more impactful manipulations?


Yeah if anything the book was a tad early and not negative enough. I thought things were heading in a bad direction but I was wrong about just how fast they were heading. Sort of makes all the heat directed at me by reporters at the time seem...well, like the complete bullshit it was. I did an updated version in late 2017 actually, you might have just missed it. It's got a bunch of post election stuff in it. Some thoughts here http://observer.com/2017/11/i-tried-to-expose-russias-media-manipulation-playbook-in-2012-and-nobody-listened-trump-pageviews-twitter/


I've heard an idea that, "You're the average of the 5 people you spend the most time with."

Who are the people you talk to or spend the most time with?


First!! Greetings from Finland Ryan! I am enjoying the book on Audible! Can you tell more about choosing this Project? Also are you planning more same kinds of books?


My view is that a writer has to push themselves or they are betraying their craft. This was 50x harder to write than my previous books. I read something like 25,000 pages of legal documents. It was really my first time using interviews in my writing. First time I had to tell a story chronologically. So I was attracted to it because it was just really hard and I wanted the challenge.

The other part of this is that it's just an incredible story. I mean Professional Wrestler Has Sex With Best Friend's Wife, Takes On Media Outlet Who Broadcast the Hidden Tape Of It...would be insane enough. That a billionaire funded the entire thing? I mean you can't make that up. The whole thing is something that could make for a Shakespeare play.


I read something like 25,000 pages of legal documents

What tools/techniques did you organize the information you extracted from that?


Loved your book start to finish.

However, what was the relevance in planting the anti-Trump rhetoric towards the end of the book and as each day passes, Thiel's decision was "obviously" bad.

While I understand your disdain for the man, is it necessary to keep tucking it in blog posts & books? Is that truly a Stoic response?


I mean no disrespect to you personally, so please don't take it this way. But I think you'll agree that it's strange that just a few months ago the charge was that liberals were snowflakes who couldn't handle information or opinions they didn't like...and yet whenever someone says something negative about Trump, his supporters claim that it's unfair or mean. Turn your comment around and imagine I'd criticized Obama at the end of the book. Do you think it would bother you like this?

Dude, "planting rhetoric?" What are you talking about? First off, it's my book so I'm "planting" anything. But more importantly, it would have been downright irresponsible, if not unethical, for me not to address the parallels between Gawker's style of communication and Trump's! Thiel justified his conspiracy as opposition to cyberbullying...and then backs Trump. It's a very real contradiction.

As for whether the passing of each day shows whether backing Trump was a mistake or not...Thiel himself has predicted there is a 50% chance of the presidency ending in catastrophe. I think he's wrong. I think it's already happened.


No disrespect taken. Also, not offended or really a Trump "supporter".

All great insights and great points, thanks for giving me something to think about/digest.

Have been following you for several years now and have noticed his name appearing more and more in your content. Was just curious is all :)


I fucking hate Trump. Still not seeing the relevance, and the fact that you assume that if it had been about Obama I wouldn't have cared is pretty telling. Whether Thiel was right in terms of Gawker has precious little to do with Trump.

Other than that, I think you've done good work.


from this layman's position, this feels like sour grapes from Gawker for losing a lawsuit. why is it so important that Peter Thiel funded Hogan's suit? is it not important that Gawker was wrong for posting the sex tape? why should i care about Peter Thiel's 'revenge' against Gawker for outing him as gay?

thanks for your time!


The weirdest part of all this was the judge allowing Hulk Hogan to wear his bandana. What kind of legal ramifications did this have? How can a fictional character(WWF Hulk Hogan) sue? FYI I'm glad he won.


Hes allowed to wear because we have constitutionally protected rights to wear religious garb (yes hulk-a-mania is a religion)


Only 3 commandments: say your prayers, take your vitamins, and listen to your parents


Was Gawker the worst, or the worst?


This sounds like a good read. When does the movie come out?


If there is a Gawd, I hope for Fincher to direct from Sorkin's script starring Brad Pitt as Hulk Hogan and Kevin Spacey as Peter Thiel in his comeback performance!!! I can smell the Oscars.


Hey Ryan, since Machiavelli said that conspiracies are weapons of the people, why do you think there are so few of them today?

How are you so prolific? What systems/routines had the most impact on your life?

I'm halfway through the book and loving it!


One of the things I explored in the book was why we seem to have this aversion these days to secrecy. A lot of people have said, "Why didn't Peter go public with what he was doing?" The other way to think about that is why the fuck should he have to? This idea that you have to tweet about every thought you have, or write a press release about every opinion or place is not only a ridiculous feature of our social media age, but it's bad strategy! Gawker wanted Thiel to have to expose himself so they could have been better prepared to fight him in court about it. The line from Napoleon is "Never do what your enemy wants you to do for the reason they want you to do it." If you were plotting to get Trump impeached, should you have to give him a heads up?

The other reason is I think we see few conspiracies is related to the first point. People are afraid to get their hands dirty. They like signing petitions, walking in marches, changing their Facebook profile picture in solidarity...but real change is often brought about by nasty means. Lyndon Johnson passed the Civil Rights Acts...but he was a corrupt asshole. He also knew how power worked and how to wield it. Part of the reason I wanted to write the book was to show how conspiracies work, and how they can be used for good and for bad.


Really well-stated in the 2nd paragraph.


Do you ever wake up at night with Ashley Feinberg standing over you?


Do you know how Peter Thiel consumes news?


would also like to know this. I guess he's not reading gawker (anymore).


What is the most loathsome fact you discovered about Gawker while writing this book?


Would you rather someone illegally download your book and read it, or not read it at all?


There are these magical places that give away free books called libraries. I'd point the person in that directly.


“Nobody Speak” chronicled this pretty well. Does your book have any additional insight for those of us that have already watched that?

Love your work-thanks for doing the AMA!


I'm not sure it did. The documentary does not feature Thiel, Bollea, Charles Harder, Mr. A (you know, the people who actually drove the vast majority of the events of the documentary purports to cover). In fact, half the documentary is about some other media outlet in Las Vegas that has nothing to do with the case at all. I had high hopes for the documentary but generally felt that it contributed to a kind of 'Lost Cause' myth about Gawker that the facts (and the legal proceedings) don't really support.


To me it seemed like it was 2 hours of Gawker trying their best to paint themselves as the victim


What do you think the stoic perspective is on your doxxing of Violent Acres? Was there virtue in it?


You know, I had forgotten all about that. But when I think back to it, I am embarrassed at what was an immature and defensive reaction. I was a kid, blogging under my own name, with basically no readers and then here came this enormous, anonymous blogger who just attacked me out of the blue. Just ripped into me and completely ripped my writing out of context and made me look like some sort of monster. When I responded, it was from that position, and in retrospect I'm not proud of it and I feel bad if I hurt her or her feelings in doing so. I'm actually going to go see if those articles are still up and if so, take them down. If she and I were ever in the same room, I would certainly apologize to her directly.


Hey Ryan, followed you for quite some time and daily stoic is on my breakfast nook table open every morning.

What would you say are the top three qualities for a marketer to be successful in the next 10 years? Skills? Traits?


Ryan, how did you personally feel about Gawker?

The site elicits are a lot of strong reactions around the web (especially here on Reddit) with people being strongly in favour of the work they did or despising it.

Where do you stand? Do you think it was a particularly vile institution or was it no different than any internet blog/'news' site - just a lot bigger?


I started out with very strong opinions (I'd written about Gawker in my first book, Trust Me I'm Lying and also in my Observer column). I'd also been attacked by Gawker several times and the subject of some preposterously inaccurate stories. So I actually went into the book with a bit of a bias, but I found myself considerably softened talking to Nick, talking to A.J, reading what many of the writers wrote in their eulogies of the site. What I tried to do in the book ultimately was remove judgement as much as possible and just show what happened. I think that's a more important lesson.

Whether Gawker deserved what happened to it doesn't change what actually happened and to me that's where there is something to learn. How did Thiel do this? What were his motivations? How did no one suspect it as it was happening? Why was Gawker unable to fend him off? How did Gawker actually work as a company? What were its motivations for publishing the story? Why has the coverage since been so slanted in their favor since losing? Those were the questions I tried to answer.


What are your thoughts on Jordan Peterson? (And the reaction positive or negative towards him)


I had a quick lunch with Jordan towards the end of 2016, before all this recent controversy and success. I think he's a smart guy--I don't agree with him on everything--and I found his responses in that long, manipulative interview that went viral to be remarkable for their restraint and self-control. I think we need more smart people like him, and certainly our public discourse would be better with a diversity of voices, both intellectually and gender/race/perspective.


Hi Ryan, how do you think, what's the biggest benefits of writing?


Writing helps you figure out what you think and know. It's also inherently humbling in that way. You think you understand something, then you try to write it and it's clear you don't. So you have to go back and really figure it out in a fundamental way.