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

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. I think the book captures that, but ultimately that will be for the readers to decide.

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

Thiel began looking for cases as early as 2011, but had trouble finding either cases that were viable or plaintiffs willing to publicly go against Gawker. But it's also important to see that from the second the rumors of the tape began to spread--in early 2012--Hogan was very public about his intention to go after anyone who published it. This was well-before Hogan and Thiel were connected. So Gawker's decision to run the tape--and we know they knew of Hogan's comments--was really the unforced error of the century. It's what put Hogan on Thiel's radar and gave him the opportunity he was looking for. There were then subsequent other cases that Thiel either explored backing or did back, in part because early on it was not so obvious that Hogan's case had legs to go all the way or that the verdict would be what it was (much of that came from more unforced errors Gawker made during depositions and the discovery process).

thanks for the answer! I'd like to ask one more question, though.

Because it all sounds a bit serendipitous. It only worked out because

1. Hogan stated his planned course of action very publicly
2. Hogan did so just after Thiel began looking for the right candidate

3. Gawker was arrogant enough to run the tape either way

4. Hogan's involvement got the case a lot of publicity (and the right kind of publicity as well)

5. Hogan was very determined to actually go through with the process even though there was a very good chance that this would not work out and draw more attention to the tape even if it did work our (streisand effect and so on)

6. Gawker failed to hide their arrogance in court and blundered their way into actually losing everyhing

Now obviously this wasn't Thiel's only option he'd ever have but I think it's fair to say that there've been questionable decisions on both ends that were necesseray for this all to unfold to Thie's advantage.

My question: how much do you think Thiel was able to influence the acting parties (directly or not) so everything would turn out like it did? Or was he just lucky that it worked out this well

Pretty simple right? But let's not confuse simple with easy.

There's a line I have in the book from Jim Barksdale, the former CEO and president of Netscape, once put it, “We tend to confuse a clear view with a short distance.” So I think one problem with your summary here is that you're missing just how hard it was to actually do all of that. To keep all the interests aligned, to keep Thiel's involvement secret, to find the right lawyers, to turn down the various settlements and gamble on a verdict, there were literally hundreds of hearings over various motions and issues and losing a single one of them might have taken the whole case in a different direction. Like 500x things had to go absolutely right to win. To me that's the fascinating lesson that people have missed about Thiel. They see this as a big guy picking on a little guy but the odds overwhelmingly favor media publishers, not plaintiffs (for good reason!)

You also have back up and realize that this conspiracy happened to come to a close with a single case (actually it was three cases settled together) but from what I saw and researched, Thiel had many irons in the fire. He was going to keep going until he got the right case in front of the right jury and won. Also an impressive, albeit scary lesson here.

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,

The people who did it saw it as a conspiracy and called it one as they were doing it, which to me is the final word in this argument (which I had many times with my editor!)

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.

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.

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

As someone who just spent the last 20 minutes reading up on it, I agree. Here's a good ELI5 on the Steel Man technique (it's the first google result, so you know I did my research)

And it comes from a gawker media site. Nice.

That's some irony.

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.”

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.

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

Between $10-$20 million is the estimate.

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."?

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.

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

https://twitter.com/film_girl/status/967186983880552448

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.

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.

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.

https://imgur.com/gallery/xULeT

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.

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

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

Or are you saying you're reading the news?

I actually use my own journal (which I won't plug but you can google it). The Stoic practice is to journal to prepare for the day ahead and then at night, journal to review the day just passed)

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

Probably more.

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.

When do you take notes about a book? While reading it or afterwards? Is that part of your daily journaling activity?

I take notes while I am reading (in the book) and then usually 3-4 weeks after I finish (unless it's urgent), I got back through and transfer the notes to notecards. Here's my process: https://ryanholiday.net/the-notecard-system-the-key-for-remembering-organizing-and-using-everything-you-read/

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.

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.

Ryan - I enjoyed two of your other books (Obstacle and Ego). One piece of constructive criticism I would have is that when you create the audio book, could you consider getting a professional book reader? I don't want to sound like a dick or anything, but the hardest part of the Audiobooks for me was that your voice was kind of... monotone-ish.

Thanks!

Look, I wouldn't want to listen to me talk for that long either, but the vast majority of listeners have said they prefer it when I read. So I got with that.

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.

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

It's been optioned. We'll see

http://deadline.com/2018/03/gawker-hulk-hogan-peter-thiel-conspiracy-blackrock-productions-1202315308/

Ryan,

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/

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.

Hi Ryan - been following your great work since 'Trust me - I'm lying' ..

Apple was no fan of Gawker - especially after the whole iPhone 4 leaking affair ..

Do you think they had anything to do with this case? Or were they just cheering from the sidelines (like many others) .. ?

Well when rumors began to fly that someone was back Hogan, there were a few candidates. I don't know if Apple was one of them, but Denton briefly considered the possibility that the Church of Scientology was responsible.

What do you make of Gawker's arrogance during the whole thing? I recall the child porn comment. It seemed insane.

I would say their hubris was immense, and a large reason for their downfall. Whether they should have run the tape is one discussion, but how I think for many years they did not take the case seriously--assuming that Hogan would settle, that he was an idiot, that people were on Gawker's side. Their decision in 2013 to ignore the judge's order to remove the article (though it was later overturned) was probably the height of that hubris, along with the comments made during the depositions in late 2013, which you referenced. Part of that aggressive exterior may have been motivated by internal insecurity. If you apologize, admit weakness, even admit wrong doing and you're an outlet that publishes first and verifies second, that puts a big target on your back.

What inspired you to move from marketing into journalism?

I'm not sure I did. I see myself as an author or a writer, who also has expertise as a marketing and strategist. I don't see myself as a journalist.

Hey Ryan, how do you think Gawker's hypocrisy at the time possibly influenced the court case? An example I have is Gawker media sites condemning sites for hosting J-Law nude photos, yet posting on their site that they were defying the judge order to take down Hogan's tape. You researched all the legal docs and did interviews, did that ever come up?

I wrote about that many years ago actually http://observer.com/2014/09/spare-us-the-sanctimony-the-gross-hypocrisy-of-online-media-in-the-nude-photo-leak/

Why was Thiel's funding even necessary for Hogan to seek justice? To me, that's an even bigger question.

From what i remember, Gawker refused a takedown order, bragged about doing so, all on a hidden-cam porn of a person taken without their knowledge. What Gawker did was screwed up, no way around it.

So why was a Billionaire needed to fund this?

As Thiel said—and perhaps only Thiel could have said with a straight face—Hogan ‘was only a single digit millionaire.’ This case took roughly four years and cost more than $10 million to litigate. Three years in Hogan lost his endorsement deals and was kicked out of wrestling when his racist comments were leaked. There was no way he could have taken this to a jury on his own. Maybe without Thiel’s help there could have been a low six figure settlement (as Gawker had done in another case) but no jury verdict in my opinion.

I know you apprenticed under Robert Greene, who wrote 48 Laws of Power.

It almost feels like this book is a modern case study for 48 Laws; would you agree?

Yes.

Wait are you the same Ryan Holiday that had that email list thing? I think I'm subscribed lol

I am. That little list started with 50 people and now is about 90,000. It's my favorite thing to do.

What’s your next book?

A secret.

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.

The fact Thiel bankrolled a lawsuit he was not involved in doesn't sit right with me. Now there's the story that Stephanie Clifford (aka Stormy Daniels) is possibly going to be bankrolled in telling her side of the Trump story, effectively lifting a private contract. Don't get wrong either. I'm glad that the dumpster fire that was Gawker went away and Trump's image/brand is slowly getting destroyed.

My question is, knowing that you are not a lawyer, what is your take on the legal precedent the Gawker lawsuit set by treating the courts as weapons of an agenda?

I tried to answer this before in another question, but literally zero precedent was set here in this regard. Litigation is financed every single day. There are lenders who specialize in this exact area and have for a very long time. In that sense, Thiel did nothing that people haven't done for hundreds of years, going back even to English courts. I think the only reasonable argument you could make is that in doing this and the case becoming so public afterwards is that Thiel made some rich people more aware of the strategy but in terms of its actual viability or precedent, that remains unchanged.

It's also interesting to note that after the case, Hogan's Florida lawyers represented Sarah Palin in her case against the New York Times and lost.

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 :)

Well I am glad we were able to have a Trump conversation with neither of us leaving upset or yelling.

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.

any tips for overcoming laziness and procrastination? can I ever not be like this?

The secret to not procrastinate is simple. Break up things in to smaller objectives, don't aim for perfect and start now. Never delay something that takes less than 2 minutes to do.

Just start.

Hard to beat this advice.

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.

I really loved 'The Obstacle Is The Way' and 'Ego Is The Enemy'. But as someone outside of the US media sphere, I'm having a hard time convincing myself to read a book about a wrestler's and some tech guy's sexual escapades.

Reckon I'd still enjoy it?

Positive. I read a lot and I hate books that really just long news articles. They don't stand up well over time. I tried to write a book that would 1) make sense if you had heard of none of the people 2) read like this was history, not news. 3) teach real lessons about power, influence, and strategy.

Do you think this type of "vendetta legal financing" should have legal ramifications? Or pre-trial disclosure requirements?

I mean, what you did there is a great example of what Peter Thiel's colleague Eric Weinstein has called the "Russell Conjugation." You call it "vendetta legal financing" but someone could just as easily call it "Good Samaritan legal financing" or "What the ACLU and the Sierra Club do everyday." If you were hit by a truck driven by Wal-Mart and they were jerking you around and you decided, I'm not going to let these people fuck with me like this and you went to your rich uncle who agreed to give you the money to hire a lawyer, is that vendetta legal financing? Should Wal-Mart be able to use that information against you in court?

I don't know the answer to your question specifically, but I do think a lot of the reactions to Thiel's involvement are preposterously overblown. On the day of the verdict, the New York Times editorial section published a debate of experts, asking about the implications of the case. Two of the three experts would come down against Gawker and for Hulk Hogan, underscoring Thiel’s early goal to predicate the dispute on privacy, not press freedom. One, a law professor and former journalist, wrote, “When human dignity is degraded by depictions of sex, nudity or medical conditions the ‘journalism’ should not be called newsworthy.” The next day the former assistant general counsel of The New York Times would be quoted in another piece published in the paper: “I think the damages are crazy, but I just don’t see this as a terrible blow to the First Amendment.” The dean of the law school at UC Irvine would follow in the same story: “I think this case establishes a very limited proposition: It is an invasion of privacy to make publicly available a tape of a person having sex without that person’s consent. I don’t think it goes any further than that and I do not see a First Amendment basis for claiming that there is a right to do this.” But then when Thiel's involvement was finally revealed, the Times ran I believe six negative pieces in seven days.

So there is quite a bit of spin there, if that makes sense.

"Ego is the Enemy" helped me quit my job! Did writing the book change the way you approach situations, or was this already standard for you by then?

Let's just say that writing a book about ego is a good way to shame yourself into trying to keep your own ego under control. Not saying I'm perfect at it (because I'm not) but I try.

What do you think of your name Ryan Holiday?

My name is ryan and i approve your use of my self proclaimed first name.

If you name is actually Ryan, how is it "self-proclaimed?"

Thanks for putting out so many great suggested reads in the past. I've enjoyed many. My two favorites so far were City of Thieves and The Tiger--I really enjoy good historical non-fiction and also the way Vaillant weaved facts into what was already a great story. Any other suggestions along those lines?

Have you read any of Robert Kurson? Shadow Divers, Pirate Hunters, and his new one, Rocket Men is out soon. Rich Cohen is also a master of this genre (Tough Jews, The Fish That Ate The Whale). I also love Candance Millard (Destiny of the Republic, The River of Doubt and her Churchill book).

Also, when you are working on a book, do you drop all your other projects or do you juggle them?

I try to work on one big project at a time--so only write one book at a time, but then as the book starts to wrap up or go into editing, then I being to explore the next project in parallel to that process.

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.

How much of the verdict money has Hogan (and his attorneys) actually gotten, and is there any hope of them getting more at this point?

The case settled for roughly $30 million. Charles Harder's legal fees were paid by Peter Thiel directly, so I don't believe he participated in the settlement itself.

Can you think of any conspiracy theory that you know to be fake, but you wish it were real, just because it would be a good story?

It'd be pretty insane if we really didn't land on the moon, wouldn't it? My friend, the writer Aaron Thier, has an amazing line in his new novel The World Is A Narrow Bridge

“Some people are so smart they can put a guy on the moon, and other people are so dumb or crazy that they can’t be convinced it ever happened and that’s the problem of human society right there.”

What was the last thing to blow your mind or made you have an "a-ha!" moment?

I'm reading Ron Chernow's biography of Ulysses S. Grant right now. Did you know that Grant stayed in John Brown's parents house on his way to West Point as a teenager? He found their son to be a bit kooky...

Hey Ryan, big fan. I’ve read Obstacle and Ego, and just finished What Makes Sammy Run per your recommendation. Loved all them.

I was listening to The Forward podcast when you were the guest. Any chance you will collaborate with Lance on a book as it was suggested during the show? I think the topic of the potential book was “what to do when your life falls apart”/“starting from scratch.”

Thank you!

I'm interviewing Lance at a conference in New York tomorrow actually. I'm hoping the book will come together!