Ryan Holiday on Conspiracy, Gawker, and the Hulk Hogan Trial
Apr 30 2018

Conspiracy.jpg Author Ryan Holiday discusses his book, Conspiracy, with EconTalk host Russ Roberts. This is a crazy episode about a crazy book about a crazy set of events--the Hulk Hogan lawsuit against the website Gawker, a lawsuit that was secretly funded by Peter Thiel. Holiday explains how this happened and the lessons for all of us related to conspiracies, patience, strategy, and revenge. Along the way, Holiday discusses his techniques for reading and lessons for how to grab someone's attention when looking for a job or opportunity.

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Explore audio transcript, further reading that will help you delve deeper into this week’s episode, and vigorous conversations in the form of our comments section below.


Craig Stevens
Apr 30 2018 at 11:22am

I just finished listening to your interview with Ryan Holiday. It was an interesting interview, and a fascinating topic, as it is not easily portrayed as a good guy vs. bad guy confrontation. However, I was surprised that neither you nor the author commented on one key irony of this legal battle, the fact that Peter Thiel was a key investor in two companies (FaceBook and Palantir) who’s main business models involve the gathering and analysis of individual’s
personal data, in some cases without their knowledge. It makes one wonder if Peter Thiel is really such an advocate for privacy, or only protective of his own.

Antonio de Sousa
Apr 30 2018 at 2:17pm

Very interesting interview. I thought the digression on how how young people should go about applying for jobs and how to take notes was valuable. I forwarded the link to my 14 year old daughter as she asked me yesterday the age old question of how do I find a job if I have no experience. Ryan’s method of taking notes is similar to mine, but I didn’t come up with it myself. As a grade 9 student in the early 80’s I was doing miserably academically, luckily for me there was an intervention and I got placed into a 2 week after school program that taught us the strategy of condensing our learning onto cards. I think I owe my bachelors and master’s degree to that after school program.

Luke J
Apr 30 2018 at 8:31pm

Good stuff

Ben Riechers
Apr 30 2018 at 10:01pm

Another great podcast. After such a smart dialogue, it was unfortunate that your guest, after providing great insights about a variety of quotes…closes with this notion that has become a common narrative from reporters…that if both sides think you were untruthful, unfair, illogical, poorly represented their views, etc., you must have done a good job. I don’t believe you can get through geometry with that kind of thinking.

Ann-Marie Doerhoff
Apr 30 2018 at 11:16pm

Fetal origins theory makes me think the idea of turning schools over to caring parents or philanthropic organizations would not work.

Christian and many other “churches” only give a small fraction of their income to charity. I heard maybe 20%. Americans can look around and see what they are spending money on and it is not poor people. They should open up their doors to the homeless instead of having living humans sleep on their front porch. The same people church’s want to force to have children are the ones that sometimes lead to homeless people. Wait…we don’t know how much they give because they are allowed to conceal their financial information…like our president.

Interesting episode….I do love the show.

May 1 2018 at 9:05am

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Mort Dubois
May 1 2018 at 12:18pm

Great episode, really interesting discussion. Two responses:

1) Re Russ’s wish that private sector would take over schooling – we saw one example of that during the Civil Rights era. White parents pulled their kids out of public schools and set up private schools that reflected their own values. What makes anyone think that it would play out differently next time? What prevents the new schools from organizing around objectionable beliefs?

2) Re conspiracies – how do we know they are so rare? Successful conspiracies, by their nature, don’t announce themselves. I see a lot of evidence that much of what comes out of Congress is the result of hidden moves by wealthy and influential players. Imagine the level of chicanery at lower levels of government.

Jeff W
May 1 2018 at 1:17pm

Mort, to your first point, that largely isn’t what happened. White families moved out of the cities into suburbs where they created public school systems that were largely all-white. They didn’t need a private school system to segregate themselves–they just needed to move. To me this shows that some people will look to segregate their children and a school being public or private has minimal effect on that.

I do agree with Craig Stevens’s point. After this episode, I grabbed Conspiracy on Audible and so far Holliday has characterized Thiel’s interest being around privacy. Would have been interesting to further dig into Thiel’s feelings on the subject. Maybe it’ll come later in the book.

May 2 2018 at 6:50pm

I think there should be another econtalk episode (preferably with Ryan) on finding jobs, interviewing, and the like.

Regarding the “binder” technique, I wonder if that may be a good idea only for certain types of interviews – CEO, University President, head coach, and maybe sales/marketing – where you need to come in with a written plan and the people interviewing you are either your boss or your direct reports. In other types of jobs, the people doing the interviewing may consist of employees at your same level, so coming in with a binder or plan could make them feel threatened.

By the way, the two times in my life where I came into an interview with a written plan, I did not get the job. I think other members of the team felt threatened. I haven’t used a plan since.

May 3 2018 at 7:06am

Jeff W writes

Mort, to your first point, that largely isn’t what happened. White families moved out of the cities into suburbs where they created public school systems that were largely all-white. They didn’t need a private school system to segregate themselves–they just needed to move. To me this shows that some people will look to segregate their children and a school being public or private has minimal effect on that.

I don’t know about the south as a whole, but setting up private all white schools and leaving the public schools for the blacks was common in the southern part of Alabama. I think it was common throughout the state (especially in rural areas) but my personal experience was only in southern Alabama.

John Bussey
May 3 2018 at 2:04pm

Loved the episode. Very inspiring.

I like the concept that some unhealthy institutions appear unassailable but may in reality be quite fragile or have a hidden Achilles Heel. And what’s required is some creativity to get to it.

It makes me think about the duopoly of the Democratic and Republican parties. It strikes me that improving the organizational capacity of funders and voters to coalesce around a single third party candidate is where a weak point is.

Adrian AC
May 3 2018 at 3:15pm

Also important to note that at the time of the Hogan case Gawker properties (led by Kotaku) had decided to go to war with their own readership over #gamergate including deleting 16,000 comments from a forum that were critical of games journalists. It seemed like Gawker didn’t like being Gawked at!

Gamers had undertaken a letter-writing campaign directed at Gawker advertisers showcasing their ‘best work’. This campaign had the intended effect.

This was Gawker’s ‘Hot take’:

Gawker lost millions in ad revenue at just the wrong time and they did it to themselves!

While the business model of Gawker was turning rumour into news and monetising via clicks the 20-year-old journalists were much more interested in using Gawker to push a postmodern neo-Marxist agenda at any cost.

May 3 2018 at 3:32pm

This episode was very different from the usual econtalk material, and although I thought I wouldn’t enjoy it I actually found it very entertaining and thought provoking.

I did have a thought about the last topic discussed on the podcast about vengeance. Although I think that the “dig two graves” and “let go of your grudges” mentality is good, I actually think that there are real reasons we as humans are predisposed to vengeance. It provides a negative incentive to people continuing their “bad” behavior. I think at the Macro level it helps to cement norms that a society needs, although I cede the point that it can also be destructive. I would be interested to hear other people’s thoughts.

Steve Hardy
May 3 2018 at 8:56pm

You don’t need charity to get rid of government schools. Simply take the money now spent on k through 12 schools and give it back to the parents in the form of a voucher, educational savings account, or as a tax credit and let parents shop for the best schools. Billions of dollars in the hands of consumers (parents) will create an entirely new education industry, not unlike the tech industry. The dozen or so billionaire tech entrepreneurs mentioned by Russ should support this idea unless they have no clue as to their success. I can’t think of a case where a government monopoly has provided a good product or service. Yet most support a government monopoly on our most important industry, education. For a comprehensive three-part video shown on PBS supporting this idea watch http://www.freetochoose.tv/broadcasts/school_inc.php?utm_source=direct&utm_medium=email&utm_campaign=201708_03_bc_schoolincpost

Steve Hardy
May 5 2018 at 12:46pm

Here is a better link to the three-part series, School, Inc https://www.cato.org/schoolinc

Stanley Mumford Myrtle
May 23 2018 at 1:15am

This was a sensational episode. Well done Russ. I ordered the book which is, I think, why Ryan does a podcast in the first place so it worked.
I did not hear you discuss the deal terms for the venture. Did I miss that part? Is it in the book? Brilliant idea and I wonder if it is going on somewhere else right now.

I agree with Steve Hardy on the educational revolution that would be started with ESA’s or some other transfer of funds from the state and federal government to the citizens of the education money spent. Imagine how many schools would be open, reopened or added onto? Imagine the billionaires lining up to sponsor schools…celebrities….Imagine the freedom the students in the worst schools would suddenly have?! The wealthiest 10 or 20 people in the USA could bring this about if they pooled their funds and created a non profit that offered to gift the funds for any school that is opened, reopened or added onto in a state that offered full ESA’s with a scale perhaps for more funds the bigger the per student allotment. This seems to me to be something they could all agree on and could be a real show of force for the importance of fair shot for every student in the US to get a great education.
Imagine if every student in say, Los Angeles suddenly had $29k (estimate of how much is spent per child in the LAUSD) to offer any school that would take them? That is a revolution. And it wold be both sides at once. It would be taking away from the government and giving to the citizens. That effort would change the country in very short order. The billionaires get together and form a non profit and commit between them $1b to start. Let the states know the money may run out so they should move fast. The non profit should create a quick and easy application process for the money as soon as the the ESA’s become law. Imagine the teachers unions trying to win a lawsuit that would close a new school with hundreds of children excelling in it?
Russ, do an entire show on the economics of education. It is a critical issue for the success of the USA. Thank you!

Comments are closed.


EconTalk Extra, conversation starters for this podcast episode:

This week's guest:

This week's focus:

Additional ideas and people mentioned in this podcast episode:

A few more readings and background resources:

  • When do secrets expire? Feature EconTalk (Extras) 2018. Complementary questions for further thought and discussion on this episode.
  • "Peter Thiel is totally gay, people," by Owen Thomas. Gawker.com, Dec. 19, 2007.
  • Nick Denton
  • F. A. Hayek. Biography. Concise Encyclopedia of Economics.
  • Unintended Consequences, by Rob Norton. Concise Encyclopedia of Economics.
  • Revenge. Wikipedia, retrieved May 3, 2018. On the origins of the mot, "Revenge is a dish best eaten cold":
    The popular expression "revenge is a dish best served cold" suggests that revenge is more satisfying if enacted when unexpected or long feared, inverting traditional civilized revulsion toward "cold-blooded" violence.[10]
    <br/The idea's origin is obscure. The French diplomat Charles Maurice de Talleyrand-Périgord (1754-1838) has been credited with the saying, "La vengeance est un met que l'on doit manger froid" ["Revenge is a dish that must be eaten cold"], albeit without supporting detail.[11] It has been in the English language at least since the 1846 translation of the 1845 French novel Mathilde by Joseph Marie Eugène Sue: "la vengeance se mange très bien froide",[12] there italicized as if quoting a proverbial saying, and translated "revenge is very good eaten cold".[13] It has been wrongly credited[14] to the novel Les Liaisons Dangereuses (1782).

A few more EconTalk podcast episodes:



Podcast Episode Highlights

Intro. [Recording date: April 9, 2018.]

Russ Roberts: Our guest today is Ryan Holiday.... His latest book is Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue, which is our topic for today.... Before we begin, I want to let parents who listen to EconTalk with their children know that today's conversation is likely to involve adult themes that may not be appropriate for children of particular ages; you may want to screen this one on your own first. And I also want to say that I did not expect to like this book. It's not the kind of book I usually read. But, I'm a fan of Ryan Holiday; and once I picked it up, I literally struggled to put it down. I read it in less than a day. It's a gripping, incredibly entertaining read, partly because of the twists and turns of the events that it chronicles, which are crazy; partly because of the portrayal of the main characters, which are really extraordinary. But it's more than that, which is why I invited Ryan to talk about it today: It's an extended meditation on power, strategy, patience, revenge, conspiracy. So, let's get to it.


Russ Roberts: Ryan, the story begins in 2007 with the seemingly casual blog post in an online publication of Gawker. Talk about what the Gawker network was at the time, a little bit about what it came to be, and what that 2007 post was about and how it involved Peter Thiel and some of those consequences.

Ryan Holiday: Gawker Media was sort of a rebel, independent media empire. They had a number of sites. They covered New York City gossip; they covered Silicon Valley gossip; they covered sports gossip. And they sort of relished their reputation as the outlet that would publish things that other publications wouldn't touch. So, Gawker famously would pay for sources. They would, you know, publish, in some cases, stolen information. Or, they would post rumors. In fact, Gawker's slogan for many years was, 'Today's gossip is tomorrow's news.' And, sort of informally, I think the attitude was: rumors are a way to get to the truth. So, they sort of saw themselves as the place that would publish things that other people wouldn't publish, and then by doing so, create sort of larger conversations that the rest of the media would then pick up. And so, in 2007, at the prompting of this site's founder, Nick Denton, Valleywag, which was Gawker's Silicon Valley arm posted the article "Peter Thiel is totally gay, people." It's an unsourced article, or at least no attributed sources. And it basically, it sort of pokes fun at and explores the sexual orientation of Peter Thiel, who, in 2007 was best known simply as the founder of PayPal, and then, you know, this early investor in Facebook. The magnitude of that bet hadn't fully been made clear, obviously. And then, at the bottom of the article--and I think this is what Thiel reacts to the most--Denton would post a series of comments, sort of speculating as to why Thiel was so secretive about his sexuality. And so, as you said, it was not just that Peter Thiel was gay--which is a fact, although a not-particularly well-known fact--it was that Peter Thiel was gay and not willing to talk to people about it.

Russ Roberts: And so, Thiel was not happy at this. And at some point, maybe right away, thought about a whole set of things, including that he was angry. That maybe this was good or bad--I'm sure he started thinking about whether this was good or bad for the world, that this kind of thing would become well known, something that a person wanted to keep private. And then, there's a dinner--what year is that dinner in Berlin?

Ryan Holiday: 2011.

Russ Roberts: So, four years go by. What happens in those 4 years, and then what happens at that dinner?

Ryan Holiday: Yeah. It's actually interesting. In Denton's comments, he even alludes to at that time that Thiel may have been threatening or that there may be some sort of reprisal for Gawker running this article: that Thiel was very upset. And yet, nothing really happens for the next 4 years. Thiel does hire an attorney in New York City named Eddie Hayes, who is a character in Bonfire of the Vanities--he's sort of a famous mob attorney and worked for a number of other outlets. And, Thiel hires him just to sort of explore what his options are, not necessarily legally. Like, Thiel ends up meeting with a few Gawker writers, just to sort of see what they--it's as if he's just sort of exploring. He's sort of rudely introduced to this media outlet, that would out him, and also finds out that this is a technically illegal, and, it might not be something that is particularly smiled upon in the media industry but it's how Gawker works. And so Thiel sort of dances around this: he looks at, 'Can I talk to them about this? Can I see why this is happening? Can I come to understand this?' And quickly finds out that that's not the case. But pretty much despairs for the next several years of really any recourse. He famously says in an interview around 2009 that he believes Gawker is the Al Qaeda of the Silicon Valley--if that gives you a sense of how strong his reaction was--but really didn't believe he could do anything. And didn't do anything about it, this entire time. And so, I believe there was both an outrage and a despair. And these twin emotions that are defining where Thiel is for this extended period.

Russ Roberts: And before you talk about the dinner in 2011 that sets the events of the book in motion, without going into any, much, lurid detail: Peter Thiel is not the only person who is struggling with Gawker's revelations. They are publishing--not just [?] about people's, say, sexual activity, but videos online of people's sexual activity; humiliating things. And they seem, at least in your book, to revel in it. And their staff is motivated and incentivized to--to smash celebrities, to humiliate people. That's the way it comes across. I don't know whether that's a portrait of their ethos.

Ryan Holiday: Well, I do think it's a fair portion, and I try to explain where they were coming from. It's a sort of--Gawker is this sort of disaffected generation of writers, sort of show up in New York City and realize that all the glamor is gone. That, there's just hypocrisy and an awfulness. And they sort of see their job as the truth-tellers that say the things that other people won't sell. And, the way that the company is set up, is: writers are paid first with how many posts that they do. And then, second, when that system is less than effective, they are paid partially based on how much traffic those posts do. So, they have a real incentive to go after these kind of salacious things.

Russ Roberts: 8:35 And how was Nick Denton, the founder--how was he doing financially from this experience?

Ryan Holiday: Gawker explodes in popularity. By 2007, it's doing, you know, tens of millions of pages per month. By 2011, 2012, were probably in the billion category. And certainly annually. So, on the one hand there is that force: Like, realizing that if pay people by the Page View, you unlock a very powerful mechanism. But then, I think the other element that Denton had figured out--and this is, I think, key to his success--is that outlets were previously far too conservative. So, the legal department would say, 'Oh, don't publish this: you might get sued. We've got to be careful. We've got to make sure our t's are crossed and our i's are dotted.' Denton realized that although people would often threaten to sue you, they very rarely actually would. There was, in 2005, for instance, Gawker runs a sex tape of a musician. And, the musician sues them for $80 million. And then when Gawker sort of writes out, 'Look, you don't want to do this. Let us explain to you why you don't want to do this,' not only does the musician drop the lawsuit, but he sends flowers to Nick Denton by way of apology. And so, Gawker is both extremely powerful in terms of their actual reach; they are also powerful because they called the bluff. Powerful people like to threaten to sue media outlets, but if you are ashamed of something or you have a secret, the last thing you are going to do is file a lawsuit, which then, you know, puts this in front of the public eye. And opens you up to discovery in a lawsuit.

Russ Roberts: And, the other piece that's going to be important is that one of their defenses, Gawker's defenses, is the First Amendment.

Ryan Holiday: Yes. They believe that, provided that something was true, it was 100% covered by the First Amendment. Which is not a necessarily inaccurate interpretation.

Russ Roberts: Right.

Ryan Holiday: But, you know, the standard for libel and defamation in this country is extremely high. You have to show actual malice. And so, I think Gawker realized, like, 'Look, if there is a halfway decent journalistic explanation for this, we're probably covered by the First Amendment. And if we're not, we're probably covered by the reluctance of the other side to actually force this issue.


Russ Roberts: So, what happens in Berlin, in 2011?

Ryan Holiday: Thiel sits down for a dinner: I'm sure he has hundreds of times. He sort of recruits young, interesting people to pitch him ideas. This is, as you can imagine, his business as a venture capitalist. And he sits down from a man identified as Man A in the book as a 26-year-old college student, who basically pitches to Thiel a solution to this Gawker problem: that, essentially calling Gawker on the bluff we were just talking about. That, in fact, there are causes of action; and that, if a plaintiff were willing to go the distance, a lot of Gawker's articles might not hold up in a court of law. Particularly in certain jurisdictions. And, Mr. A pitches to Thiel that he thinks it would take about 3-5 years and roughly $10 million dollars to test this theory. And, it's a pretty remarkable pitch for this unproven young man to make. And he makes it to Thiel. And Thiel sort of agrees on the spot. You know, by 2012, Thiel is worth a few billion dollars. Gawker poses both this personal, existential threat to him; but also, being on the Board of Facebook, and talent[?] here, and the business interest that he's now accumulated, Gawker is probably an economic and a financial threat, as well.

Russ Roberts: In what way?

Ryan Holiday: Well, if the website that will run sort of an unsourced, unattributed outing of you, I guess you would also sit there and imagine what rumor they might post about Facebook, or about Mark Zuckerberg, or about, you know, Palantir's data collection methods. You could see how a site like Gawker would post significant liability to anyone whose interests are in the billions of dollars. And I'm actually not trying to imply that Thiel here was motivated by greed. I'm saying, purely from a defensive standpoint, if there's a media outlet that will publish rumors--and I was the Director of Marketing at American Apparel, and we would see articles from Gawker which were very poorly sourced, were very poorly attributed. You know, affect the stock price of the company on a daily basis. You know, the market moves on news. And Gawker was big enough by 2011, 2012, that they had the ability to move the market. They destroyed careers of politicians--for good reason. You know, they'd hit Apple very hard when they got a stolen prototype of an iPhone, for instance. You know, Gawker was a very powerful media outlet. And, Thiel had a variety of interests that were probably threatened by that.

Russ Roberts: So, the rest of the book--a chunk of the book, is the discovery by this process that this 26-year-old starts in motion--that Thiel okays and funds, involving a sex tape of Hulk Hogan, where he brings suit. And Gawker doesn't expect to lose this suit. Because--why?

Ryan Holiday: Right. So, in 2011, the conspiracy goes into motion; and Thiel sort of just looks for an opportunity for an additional year. And it's not until 2012 that Gawker runs this sex tape of Hulk Hogan. And it's sort of the exact opportunity, which I go into in the book, that Thiel was looking for. It's not a First Amendment case necessarily. It's a privacy case. It's got a jurisdiction in a small court in Florida, with very strong privacy, privacy rights in that state. There's also a potential copyright claim. But, again, I think Gawker doesn't take it serious for a couple of reasons. So, one: The case is quickly tossed out of Federal Court. So, Gawker thought, 'Well, of course, it will also get tossed out of Florida Court. But, also, it goes to the fact that Gawker had run tapes like this many times. And the lawsuits had either been dropped, or they'd been settled for, at most, you know, $100 or so thousand dollars. And so, the idea that this case, which Hogan represented by lawyer that too had found that Hogan was going to win $100 million dollars, which was what he had sued for, just seemed ludicrous. And, it seemed liked Hogan was playing the exact same playbook that all celebrities play: Which is, 'You threaten to sue; you sabre-rattle. And then you are not willing to go to trial because you don't want to see this thing broadcast in front of the media over, and over, and over again. And eventually you settle for a token amount.'


Russ Roberts: And, I don't want to give away any of the plot twists. But, suffice it to say that what actually happens in this lawsuit--it's hard to believe. It takes so many extraordinary turns. And what actually we learned about the case itself, Ryan--it's--you couldn't make it up. It's just ridiculous. And riveting. The point, the only point I want to make now, before we turn to the bigger issues around this story: The only point I want to make now is that, as Hulk Hogan goes to trial, and, as Gawker prepares to defend itself against this case--which it assumes it's going to win, in your telling of the story--none of the participants, none of the direct participants--Hulk Hogan, his team of lawyers--has any idea that Peter Thiel is funding it. And that's really the conspiracy.

Ryan Holiday: And, that was, in some ways, Thiel's brilliance. You know, Thiel hires Mr. A. Mr. A hires Charles Harder, who is the attorney; and then Charles Harder reaches out to Terry Bollea, a.k.a. Hulk Hogan, to operate, to actually pursue the case. And this is more or less the same process in a number of ancillary cases that Thiel also pursues, not knowing at the outset that the Hogan case would be so definitive. And so, yeah. So, Thiel has set up a system where his identity is obscured almost--at some point, I guess, three layers deep. And that allows him to operate in the shadows. And it also makes it very difficult for Gawker to have really any suspicion that this isn't just an ordinary celebrity fighting a pretty typical news story in Gawker's archives. And, so, everyone thinks it's business as usual. But, in fact, the calculation has been drastically changed.

Russ Roberts: And, we're not giving anything away--if you are a net savvy person, Gawker doesn't exist any more. You can find the--if you google Gawker, you'll pull up--I don't know what you call it--their tombstone, essentially, their epitaph. The sex tape of Hulk Hogan doesn't exist in any public way. You can't find it. And, at the time of the suit, which I do remember, vaguely, that there was a Hulk Hogan sex tape lawsuit with Gawker--nobody knows it's Peter Thiel.

Ryan Holiday: Right.

Russ Roberts: Which is unbelievable. And yet, eventually, we find out. So, finish this part of the narration. How do we find out?

Ryan Holiday: Well, I think the point which you just raised is a very good one. Which is that, as I looked for this, there is very little in the way of precedent in terms of an individual sort of going to war with a media outlet and then, not only winning, but sort of winning in such catastrophic fashion. Right? There have been large media judgments against outlets before. But very rarely do those outlets force the immediate bankruptcy of said publication--which is what happened with Gawker. And then, for about two months after the verdict--the verdict comes in, in mid-March of 2016--it's not until May, late May of 2016, that even really strong rumors of a backer begin to emerge. And then the story is broken by Forbes; and then confirmed by the New York Times. It's probably because Thiel had begun to sort of become so proud of what he'd done that he told more and more people, and eventually the news got out. The secret was just held by too many people. And, 'Wow, it's happening.' It's not that interesting. But after the event, after the verdict has come in, I think it was only, it was in some ways inevitable that the public that journalists would want to find out how the hell this could have happened. And, so, too, there was a ticking clock on Thiel's secrecy. And Thiel said to me when I interviewed him that secrets tend to have an expiration date, and that this one probably did, too. So, the conspiracy theory becomes confirmed as a conspiracy theory in May of 2016.

Russ Roberts: And ironically that's a story that would have been broken by Gawker if it had existed at the time, perhaps. But it doesn't. It's broken by--

Ryan Holiday: That is very ironic. And [?] that to me--so, what does it say that a journalistic media outlet that specializes in, you know, sort investigative journalism as they saw it? Or, you know, Gawker sort of first and last article was supposed to be, like: How things work? Right?

Russ Roberts: The inside scoop--

Ryan Holiday: The inside scoop. And here, when their life depended on it, they were not able to see the inside scoop or what was really happening. And, in fact, one of Gawker's editors spoke for a documentary about these events, and he was saying, 'We scarcely could have believed something so conspiratorial could have happened.' And, you know, my sort of rejoinder in the book is, 'That's precisely why it did happen.'


Russ Roberts: And then, finally, the other change that happens is that a lot of people who had no stake in the game--we might call Adam-Smith-impartial-spectators--rejoiced when Gawker was destroyed. Because they said, 'There's a nastiness here. We're feeling humiliating things often about not-so-famous people. And, ruining lives.' And some lives, of course, you could argue, deserve to be ruined. But a lot of the, some of lives that were ruined at least in your telling seem like they shouldn't have happened. And so, a lot of people rejoiced when Gawker was destroyed[?]. And then when they found out that it was a really rich person who destroyed it, there was an enormous backlash--that this was a terrible precedent. We'll talk about that in a minute. But, just describe that swing.

Ryan Holiday: Well, that's right. When it was a celebrity versus a media outlet, you could conceivably believe that this was a sort of David-and-Goliath story.

Russ Roberts: And Hulk Hogan--Hulk Hogan is kind of a lovable celebrity. He's sort of a mock-celebrity in a way. Right? He's a professional wrestler--

Ryan Holiday: Yeah. And I think that professional wrestling ties part of this, too, right? We love to have the good guy and the bad guy--that is the plot of basically every professional wrestling match. And Gawker had sort of behaved so egregiously that Hogan was the sort of hero and Gawker was the heel. And so, when Hogan triumphs, it seems like, 'Okay, look, this is a--this is the little guy beating the big guy.' Or, this is some poetic justice here. And, in fact, legally, that was also the interpretation. The New York Times itself had a number of, impaneled a number of experts. And the experts basically go, 'Look, the precedent here is that you can't run celebrity sex tapes. You can write about them, but you can't run the tapes themselves.' That's basically the limit of what the implications of this are. And then, two months later, when Thiel was revealed, the optics suddenly shift. And people are, 'Oh, what is the precedent of this? Is this very [?]?' Well, the legal precedent of course remains exactly the same and does not change. But the idea that a billionaire was able to bring this about--in secret, no less--and over-potentially it's sort of a personal grudge, which is how I think some people saw it--does alarm, if not the average person, it certainly alarms people who write for media outlets for a living. And so, there's been this sort of hysterical interpretation ever since. Which is that, every media outlet is now, you know, in grave danger from Peter Thiel specifically or billionaires generally who want to shut them down because they don't like what they are writing.

Russ Roberts: [24:33] And, we'll talk about that in a minute. But, just to finish up the story--I hadn't thought about this when I was reading the book or till we just talked about it. But, the whole Hulk Hogan lawsuit felt in some dimension like just an extension of the world of professional wrestling. Just theater--you wouldn't be surprised in Andy Kaufman was the--his lawyer. What's reality, here? And people said, as you point out, Hogan was maybe just doing this for publicity; or really wasn't, he wasn't deeply hurt; and what you find out in the book, without revealing any of the details, is that there is a lot at stake here for Hulk Hogan. And there's a, really an extraordinary denouement, for him.

Ryan Holiday: There's an element of professional wrestling in the legal system itself, which is, like, every lawyer, is like, 'We're going to trial. We're going to win this. We've got an amazing case. We're suing you for a trillion dollars.' There's this sort of extremeness and hyperbole in the system. And then, on the other side of things, it's like 90% of cases settle. Or even higher than 90% of cases settle. And they never do go to trial. And the sort of legal system is actually quite boring in that way. And so I think that was part of this, as well.

Russ Roberts: Yeah: This is where the guy hits the other guy over there with the chair and the blood's real. It's not staged. Gawker really does go out of business. I think that really does get, goes into a personal bankruptcy as a result of a--

Ryan Holiday: And there's a wrestling term for that. They call it a shoot. And that's when a match that it scripted, the wrestlers break script and it becomes and actual fight. And there is a moment where Thiel actually passes this down to Hogan through the intermediaries and says, you know, 'They think this is kayfabe'--that's the wrestling term for fake. 'It's actually a shoot. It's going to be a real lawsuit.' And I think in some ways, Gawker was just--never believed this was going to trial. And was so caught off guard when it did.


Russ Roberts: So, let's, now let's get into the issues that are at stake here beyond the entertainment. Which is tremendous. As I said. This is a book that--I couldn't put it down: The twists and turns, the portraits of the individuals are just--you did a superb job. First thing I want to establish: How did you figure out what actually happened? How did Ryan Holiday, not a Gawker employee--how did Ryan Holiday come to be able to give us what appears to be inside information about Mr. A, the person who proposed this, about Peter Thiel, about Nick Denton?

Ryan Holiday: Well, it is weird. One of the things that surprised me about this is that, I thought I would have to be entirely dependent on sort of access to these sources. When I actually sat down and I read the legal documents--there's something like 25,000 pages of legal documents--it became pretty clear to me as I finished them how little they'd actually been read by the media that had reported so extensively on this story. So this goes to that earlier part that, like: Hey, the media outlet says they investigate things, but, in fact, tend to stop at the superficial level. Because they just don't have time. And so, being able to do this as a book, I had a lot more time and a lot more resources. I could step back and actually look at this. But I also had the benefit--I was probably the only person on the planet who has been able to talk to both Peter Thiel and Nick Denton at any sort of length. So, I interviewed those principals. And then, through my access to those people, I had access to AJ Daulerio, who ran the Hogan tape. I was the first and only person to speak to Mr. A., and in fact broke his identity in the book. And Hulk Hogan, and Charles Harder. So, I actually sat down and talked to the people. And one of the things that I did, was, going into this, going, 'I actually want to find out what happened.' I'm not interested in saying whether it should have happened or shouldn't have happened. I think we needed to start with what actually happened. And that intention gave me both access to people, but then also gave me a willingness, a lens to see what actually happened. Whereas, I think, so many other reporters writing about this were so incensed by the outcome, and so alarmed by it, that they frankly missed what actually occurred.


Russ Roberts: One puzzle, which I don't understand--and you may have talked about it in the book, but if you did, you didn't talk about it at length. Why didn't somebody restart Gawker the next day, under Looker, or some other name? Nick Denton--why didn't Nick Denton do it? Why did Nick Denton say, 'Well, that didn't turn out so well; I'm out of money now but this is a profitable idea, writing outrageous stuff. And it only means that you can't run a sex tape--you mentioned AJ Daulerio, you are really, you say he was the editor, I think responsible for running it. He ran it on a Gawker website. Why didn't someone just restart and stay away from running video?

Ryan Holiday: It's complicated. So, one, I think Gawker was less profitable than people thought. Gawker sort of projected its image as being this enormously profitable, huge, intimidating website. But, the truth is, they sort of could barely afford to litigate the case as they litigated it. They were sort of drowning under the legal bills that, as this dragged on. But they couldn't--the real precedent--they were worried about were: If this guy can win, then everybody is going to come after us. So I think it was less profitable than people thought. But it was very much a product of a unique place in time, early in the Internet. So, as this is founded in the early 2000s, you know, Nick just starts this website in his living room. And it becomes very quickly a media outlet that's doing millions, and then billions of pager[?] a year. If you were to start that today, you would need a lot more than a dining room table and couple laptops. So, Gawker had, was created when blogs were new. When they were, this is sort of the new frontier of media. When there is not a lot of sort of taking this medium seriously by both media outlets and sort of businesses and public failures. And so, being this--Thiel's argument to me, when he talked to me about this was, he believed that Gawker was sort of a one-in-a-million company. And if it were to disappear, it not only would not be re-created, but people actually wouldn't miss the service that it provided. That, we would just go about our lives as if it never existed. And, what's interesting is that, now, the domain name, Gawker, is sort of in limbo. But the bankruptcy estate of Gawker still owns this domain. And, who is going to get it is an open question. But a number of Gawker writers put together a crowd-funding campaign. They tried to raise $500,000 to buy the domain back. Which is probably less than it would sell for anyway. So, I'm not sure, even if they could have raised the half million, would have been successful. But, you know, they raised something like 17% of their stated goal. And, so, in some ways, that might be a reflection, too, of the fact that, we enjoy Gawker of this guilty pleasure while it existed. But, it's not as if we wake up every day actually pining for the service that it provided.

Russ Roberts: Well, there are a lot of places that still provide it a version of it, of course.

Ryan Holiday: Sure.

Russ Roberts: You could say the whole Internet is--is somewhat focused on salaciousness, or the latest hot story that people don't know about, and you get the inside scoop.


Russ Roberts: Now, this is a book partly about revenge. But, it's more than that. And a lot more than that. It reminded me of a topic we talk about on EconTalk, the Bootlegger and Baptist phenomenon. In the case where we usually apply it, it's a politician justifying some regulation, using high-minded ideals when in fact there's a self-interested motive that's being covered up. Certainly, Peter Thiel had high-minded ideal--excuse me--had a self-interest motive: he wanted revenge. But he also, at least the way you tell it, had an interest in making the world a better place, and felt that he wasn't just avenging--in justice, he was making the world better. Do you think that--is that accurate in your mind, about his motivation? And do you think it's true? Do you think that the world is a better place--without Gawker?

Ryan Holiday: Well, I think it, you know, goes back to Thucydides, that the sort the three motivations that he said, you know, exist, are, fear, honor, and interest--or self-interest. And I think Thiel is motivated in a way between all three, right? Because there is fear of his private life. There is his potential business interest. And then there is this sense that, as a sort of, idealist, big thinker, that maybe this is not a force for good in the world. And so, I think it's all three of those. Whether this was a good thing or not, I think is really complicated. And it would almost change on a daily basis as I was writing the book and thinking about it.

Russ Roberts: Talk about it. Talk about that evolution of your own feelings.

Ryan Holiday: Well, you know, I went into this as someone who has not only worked for and with people that have been very unfairly treated by Gawker. But, myself, have appeared on Gawker--in 2011, I was working at a company that was being sued by someone, and then mysteriously my emails were hacked into and then they show up on Gawker. You know, Gawker had written negative things about me before. So, when I went into this, there was an element for me that just said, 'This is very much deserved.' And yet, it's very hard to talk to someone who, you know, ends up having to mortgage their apartment to pay, to, you know--as part of bankruptcy proceedings, and rented out on Airbnb, or to see, you know, 300 people put out of work, and not, kind of go, 'Wow. That's harsh.' Right? That is a lot. So, just dealing with the people involved on all sides, sort of makes you invariably see this in a more human way. So then that was part of it. You know, [?] backing Trump, and then the 2016 election which I think paints a color on some of this, as well. So, I think--I would go back and forth on it. And I never--I tried--ultimately, I decide not to a stand one way or another; but it was, as I was saying earlier, just kind of show how it happened and then leave it to the reader to decide a little bit more what it means. But I do think it's it hard to argue that the world in 2018, from a media standpoint, is better than how it was in 2007 or 2011. How much of that has to do with Gawker; how much has to do with, you know, a number of other forces I think is impossible to clearly state one way or another. But I don't necessarily know if the world is like, been magically transformed by what happened.


Russ Roberts: Yeah. You wrote a thoughtful essay--you've written a number of thoughtful essays in the aftermath of publishing the book. And we'll try to link to as many as I can find. And you'll help me. But, you write, in one of them, you speculate--and you do this in the book as well--it's kind of a shocking speculation that we don't have enough conspiracies. You say, "What would the world look like if people changed things, conspired negative worse to change things they found injustice, unfair immoral"? And you actually raise the question about whether we have too few conspiratorial activities. Normally people look down on conspiracies. It's a negative word. It's shadowy. It's secretive. It usually means--there's something nefarious about it: "Conspiracy." And it's not just because it's a secret. It's basically a plot. And, you actually raise the question of whether we should do more of these. You want to try to defend that?

Ryan Holiday: Sure. Well, part of this is sort of, is, it comes from Thiel. And, you know, Thiel is this contrarian. He's really good at sort of posing interesting questions. And maybe we wouldn't have considered otherwise. Famously he gave, in an interview he gave with Marie [?] he was talking about whether corruption--he was talking about corruption in South America. And he's speculating: You know, Is the reduced corruption a good sign or a bad sign? Maybe that means that actually the economy there has become less dynamic. And, so, one of the arguments that I thought to make in the book is that, although we can disagree with whether this should have happened or not, or there is some subjectivity about whether Gawker was evil and whether it's good that they are gone or not, I am at least heartened or impressed by the sort of ruthless efficiency and the hypercompetence on Thiel's--and in fact, was sort of repeatedly appalled and disappointed by the incompetence and mismanagement of Gawker. And so, what I'm arguing in the book is: You can't dispute that Thiel set out to produce a change. That he thought Gawker was a force for evil in the world. And now they are no longer in the world. Right? There might be some unintended consequences, some blockback [blowback?]. But he does accomplish what he set out to accomplish. And this was a thing that many, many powerful people agreed with him on, but despaired of being able to do anything about. And so I am heartened by this sort of efficacy of it--that he managed to do this. He managed to do it in secret. He managed to actually get a fair amount of people on board--you know, agreeing with, at least, the outcome. And he did it because the sort of traditional remedies had failed. Right? Gawker wasn't a problem you could solve by writing an op-ed about. Or signing a petition. It required this sort of, you know, extra means. And you did it legally--right? You did it within the legal system--

Russ Roberts: within the constraints of the First Amendment. You didn't get the First Amendment abolished. And then, 'Oh, great. And then we'll get Gawker.'

Ryan Holiday: Right. There's no travesty of justice here. There was no criminal enterprise. There was no assassination attempt. What he did was he said, 'Okay, look: The way that this should work, isn't working. What's something that other people haven't tried?' And, you know what, it is alarming, right? You look at our legal system and you think, 'Uh, look: The people with the best case win.' But had Hogan not been backed by Thiel, it is almost certain that this case never would have gone to trial. And he wouldn't have gotten the verdict which the jury later said he deserved. And so, um, what--I guess my proposal is--what other things are people quote-unquote write about. But that writeness[rightness?] isn't translating to might? And, should more people try to test that?


Russ Roberts: And that's one of the most provocative ideas in the book. And it's an idea that haunts me a little bit--I think listeners will understand. F.A. Hayek quote, which I love, 'The curious task of economics is to demonstrate to men how little they really know about what they imagine they can design.' A conspiracy is a design. It's a design to accomplish X. You point out that X was accomplished. That seems like, really, impressive. In theory. And you put the word "Right" in quotes because, well, that happened to be one that, well, we're somewhat sympathetic to, perhaps.

Ryan Holiday: Yeah.

Russ Roberts: But, there are a lot of, we could think of, we're not sympathetic to. Let me pick one that I am sympathetic to. And, just, maybe you can think out loud with me about it. I've often wondered whether the wealthy people of Silicon Valley--and we're not going to name them; there's about 10 that we're talking about--but between the 10 of them, they have a lot of money. What if we could get all 10 of them--and we'll throw in some people outside Silicon Valley--there's two in Seattle that might come to mind. Let's get these 12 people. And let's say, let's get them in a room; and let's get them to recognize they all actually agree about already, that the American public school system is not very good.

Ryan Holiday: Mmmhmm--

Russ Roberts: And, we should do something about it. They all think that's true, I think. They are all appalled at the current state of education in the K-12 [Kindergarten-through-12th grade] arena. And, let's say they all could agree on what needs to be done. And in my strange, peculiar world view that would be to get the government out of the funding of public education and out of education. And to rely on self-interested parents. And philanthropic institutions to protect people who don't have the means to pay for school on their own. That's my crazy world view.

Ryan Holiday: Sure.

Russ Roberts: Crazy world view scares a lot of people. Some of you who are listening, you think that's a bad idea. You have a lot of affection--and I could be wrong about my view. Your affection may, should be, is appropriate: that the public school system is the backbone of the American way of life; and we should do everything: We should have a conspiracy to make it better. But my view is it's the other way around. So, these 12 people get together. They don't tell anybody, because that could mobilize the Teachers' Unions, everybody else. And they conceive of this end-around system that might involve MOOCs, might involve education, it might involve political action. It might involve some things that were not so attractive--planting stories in the media about bad things the public school system does. Is that a good thing? I don't know. I don't know the answer to that. My first thought is, 'Oh, it's a good thing.' And then my second thought is, 'Well, I like it because it's in my direction'--

Ryan Holiday: right--

Russ Roberts: because if it weren't in my direction, maaaybe I wouldn't like it so much.

Ryan Holiday: That is the interesting element of it all. I mean, the work, the methodology, is neutral, right? It's just that it's a strategy like any other strategy. It just happens to be the least transparent of strategies by definition. And, I think that's typically why conspiracies tend to be used in desperate situations, right? It's sort of the means of last resort. Because, you are: by keeping the secret, you are almost admitting that you are keeping the secret because if you told everyone what they are doing, they would as, even in your example, mobilize against it. But, the hypothesis is that: If I were to achieve the result that I want, things would be transformatively better; and everyone would thank me for it or the world would be a better place. And so, that is the complicated element of it. I mean, a couple of interesting conspiracies for me. And you could argue in some ways, a lot of the sort of Civil Rights Movement were somewhat conspiratorial. You know: Rosa Parks doesn't--the idea that she was just riding a bus one day and said, 'You know, today I've had enough,' is just factually not what occurred. Right? 'This was a planned, this was a planned event; and it was planned to bring about a specific end.' And, more conspiracy theory: Right now people are speculating that someone is funding Stormy Daniels' legal bills against Donald Trump. And so, what's interesting to me about the Stormy Daniels example, is that the same people who were appalled by Thiel's playbook are probably cheerleading the exact same playbook being operated against a different opponent, in a different scenario. But, the conspiracy is essentially the same, and it's using a sort of technicality of the legal system the same way. And so, it is interesting. And, to me, the book was to sort of put this bigger, kind of uncomfortable question out there, and get us at the very least to think about it. Because I think one of the things that allows the really bad conspiracies to happen is that we are so unaware of them. And, perhaps, Russia--a more, sort of conspiratorial country, has used that to our disadvantage in some ways. We sort of believed the Cold War was over, and people didn't do stuff like this any more.

Russ Roberts: Yeah.

Ryan Holiday: And that's why we were caught sleeping.

Russ Roberts: Yeah. The other part of it, though, which I alluded to but didn't make clear, is that it's not just that it might something I don't agree with. It's going to achieve something that any conspiracist might imagine. It could achieve some things we have no idea about. So, the unintended consequence idea--that, it's not just that--well let me say, let me rephrase that. In a complex world where reality is emergent, it's very hard to steer things. So, conspiracies in some sense are inherently difficult. This is a very narrow conspiracy, that your book's about: destroying a media outlet. Transforming the American education system: transforming public attitudes toward--you pick it, whatever is your key area--those things are: One, because of complexity they are hard to achieve. Much harder to achieve. And Number Two, you don't control them, after a while. They take on a life of their own.

Ryan Holiday: Right--

Russ Roberts: And they conspire a lot of control. And it just raises an interesting moral question, that I struggle with and have mentioned on the program in passing, that: You know, it's hard to be active when you are not sure that every action you take is inevitably going to lead to something that's good. It can lead to a form of passivity. I know you are a Stoic. I am, I have a bit of Stoicism in me. And it's my Hayekian Stoicism that often leads me to say, 'You know, I don't feel confident to do anything about x, y, or z.' And yet, at the same time, I know that if I just sit around and observe the world passively, I feel I've failed.

Ryan Holiday: That's the tension, right? Um, you know, the famous example is that the republican Senators conspired to assassinate Caesar, who has made himself dictator. And they cause, they succeed in killing the dictator; but then they cause a civil war, in which, you know, many, many people died. And then Rome permanently ceases to become, ceases being a Republic. And Octavian then becomes Emperor. And so, what's interesting--you know, my other books are about Stoicism--there is this tension in Stoicism itself about conspiracies: Do they make the world better? Do they make the world worse? Are these unintended consequences? And, you know: Do you stick with this sort of purity of your motivations and do nothing? Do you have your idealism that your conspiracy can change everything? When, the truth is, there are always these unintended consequences? And, you know, the other example would be sort of the history of the CIA [Central Intelligence Agency], is like, sort of, blowback after blowback. Every time we try to conspire and get involved somewhere, it tends to, you know, not necessarily make things better. However, it strikes me as being very alarming that the solution to that would be, or that the response to that would be resignation, or, you know, as a friend, Tyler, has sort of called this 'complacency': Do--is the threat of unintended consequences justification for the sort of morass of complacency that we have as society? I'm not sure that's any better.

Russ Roberts: Yeah; I raise this in the Jordan Peterson episode, when he talks about a principle, one of his 12 Rules for Life that I'm very fond of. Which, you know, in many ways try to live my life by. Which is: Fix your own garden before you end up trying to solve everybody else's problems.

Ryan Holiday: Sure.

Russ Roberts: And, there's something very beautiful about that. It's really a--it's a fundamental statement about epistemological humility. It's saying, 'I don't know enough to fix your garden, Ryan. I'm not going to tell you how to run your life.' And yet, at the same time, if that's what everybody does, some nefarious folk can take over the parts of the system that do have levers. And do a lot of really evil things that make it really hard to fix your own garden. So, there's a tradeoff there that's not--I don't think it's solvable. I think it's something a person should be aware of.


Russ Roberts: Let's talk about Mr. A. I found it strange that you didn't identify him in the book, and you didn't tell us why you didn't identify him. So, I'd like you to mention that in passing. But, I'm really more interested in an essay you wrote recently about, what you learned from that dinner--

Ryan Holiday: Yeah--

Russ Roberts: about auditioning versus interviewing, that I think is very profound, and extremely useful. Especially for young people who might be listening.

Ryan Holiday: Well, what was fascinating to me--my first interview with Thiel as I was thinking about doing this book, he sort of offhandedly mentions this Mr. A character. And, this is one of the most reported stories probably of the last decade--the idea of, you know, professional wrestlers who have a media outlet and then their ability to be involved--the idea that there was still a secret, that there was still a whole person, and not only did no one know their name, but they didn't even know that they played a role in what happened was just--astounding to me.

Russ Roberts: And just to review, just to review--this is the 26-year-old kid who comes to Thiel at a dinner in Berlin. It's basically a one-time opportunity for this kid to put something interesting in front of Peter Thiel. And of all the things he puts in front of him, it's not an idea for a unicorn company in Silicon Valley that's going to be worth a billion dollars, some app. It's a strategy and a game plan for personal revenge. That--the 3-5 year part turned out to be exactly right. I don't know about the $10 million part. But--I don't know if he got that right, in terms of the budget.

Ryan Holiday: Certainly in the ballpark. And, so, yeah: So, I was the first one to talk to him. And, the only one, as far as I know. And our arrangement was that he was willing to talk to me provided that I wouldn't name him. I do know his name. It struck me as a pretty minor compromise. In exchange for getting the perspective of the person who, 1. had the idea and, 2. executed the vast majority of it--to be able to add that perspective but not necessarily put a name on it, it struck me as--to do the opposite, to not include it because I couldn't give his legal name--struck me as a ridiculous, you know, a ridiculous logic. So I ended up making the exchange. I don't belabor it in the book. I sort of feel like it's on other media outlets, to take the ball and run with it. If they do that, that's great for them.

Russ Roberts: And he's--it's discoverable. But you did mention, earlier in our conversation today that you reveal his name in the book. I read every word of the book, as far as I know. I don't think--

Ryan Holiday: No, no, no, no. I'm the first to reveal his identity as--

Russ Roberts: His role. Not his identity--

Ryan Holiday: His, role. Correct.

Russ Roberts: His character in the plot.

Ryan Holiday: Yes, exactly. And, to go to your point about what happened: The idea that, you know, it struck me, like--I've actually had--not dinner, but I went to an event at Thiel's house when I was about 26 year's old--I was probably 25. And, I remember flying out there, and 'This is going to be really cool.' And I just wung it--I just winged it. I just said, 'Oh, I'm going to Peter's house. This is very cool.' You know, it was interesting to think like: 'Oh, man,' this guy was just operating on a whole other level. He went in there. He had an idea. He had a plan. He'd researched it. He'd mapped out what he hoped to accomplish from this chance encounter. And it was a similar receipt[?], that, in football they talk about this: There's sort of a coach that goes in and goes, 'Hey, I'd like the job.' And then there's the coach that comes in with a binder, that describes exactly how they are going to do the job, what conditions they want the job under; you know, what sort of budget, what their timeline is; etc., etc. And it just struck me that there was a lesson there, in this 26-year-old. Again, you can agree or disagree with what he pitched. But, you can't, you can't argue with the fact that his pitch was successful and that it wasn't transformative for the parties involved. And so, I just liked, the sort of ambition--the willingness to put yourself out there, despite really having no qualifications whatsoever. You know--it struck me as very earnest and impressive in that way.

Russ Roberts: Well, I think Peter Thiel was impressed with it, too. And he might have been impressed even if he hadn't--if he didn't think that the particular plot and plan in that binder was going to successful. I think that's probably true of so many football[?] coaches, when they interview. The owners may not think, 'I don't like that idea,' or 'I think we shouldn't practice on Tuesday afternoons.' But, whatever it is, the fact that there's a meticulousness--which I think appeals to everybody, regardless of the quality of it. Meticulousness has a certain, has a certain virtue in people's minds. Maybe not always justified. But, it certainly is impressive. But, I think the phrasing I loved in your essay, 'an audition versus an interview.' So many times, especially when we are young, don't know much about the world, we go into an interview thinking, as you point out in the article, 'I'll wear a good suit. I'll make sure my hair looks good. I'll brush my teeth.' And, 'I'll make sure I don't fiddle with things while I'm talking.' You know, you have a whole set of rules.

Ryan Holiday: Yeah.

Russ Roberts: But what you don't think about is two things: How much research do I need to do before this meeting, to be prepared for it? And, more importantly, or as importantly: What do I need to do with that research to be appealing to these folks? And, you give an example in your essay--and I think I've probably mentioned on the air--so many times, young people write job letters where they talk about how much they want the job. How much it would mean to them. How valuable it would be to them. As if their urge, their desire, is a selling point. When, in fact, they should be thinking about something else, which is: What can I do for you? Why is this good for you? Not good for--we know it's good for the interviewer, the interviewee. The interviewee needs to make the case for why it's good for the interviewer.

Ryan Holiday: Well, I get a lot of those emails myself. I've been sort of mentored and trained by a writer to become a writer. I get a lot of emails. And they're very nice. And I certainly feel a little strange complaining about it. But the emails basically go like this: They go, 'Hi, Ryan. I'm a huge fan of your writing. I want to do what you were about to do for Robert Green. Please hire me. I'll work for you for free.' And, in their thinking, the lack of payment is what makes them a compelling candidate. And, if you wrote--I thought this when I was their age, as well; it wasn't until I got older and worked for more people and set up my own business, that I realized that most companies don't have sort of--it's not like there's a whole stack of tasks over here that a company isn't doing because it can't afford to pay someone to do them.

Russ Roberts: Yeah.

Ryan Holiday: It's that they either don't know that they have anything that needs to be done, or that there's a shortage of good people to actually do them that they feel like they can trust with those things. And so, it's actually--it's not how little are willing to be paid, but what expertise are you bringing to the table? What are you especially good at? What can you do that can make the life of the person you are hitting up easier in one way or another, that's going to get you the answer you want. Those coaches that came in, that we were talking about earlier, it's not like, they are like, 'Hey, I have a really good plan. Also, I'll do it for free.' Actually, they are demanding to be paid a lot of money. It's that they have, they are demonstrating or signaling how seriously they are going to take it, and how much value they are going to give in exchange for that salary.


Russ Roberts: Yeah. And, of course, when you are young you don't have much to offer. I get--a lot of people ask me for advice sometimes about how to get a job in x, y, or z. Maybe not as many as you, I'd guess. But, I always say to them, 'You have to be aware of the fact that you don't have much to contribute. And that your desire to work there is not one of those things.'

Ryan Holiday: Totally.

Russ Roberts: And so, you've got to figure out a way that you are a value. One way to do that, of course, is to do that research to show that when you come to a task, you give it your all. And, it's not so much, necessarily, what comes out of the research, but that you signal in advance that you are a hard worker. And that you will persevere. And that means you may be of value, just for that skill. It's not a trivial skill, by the way. It's an incredibly rare and important skill. Simply--and we know that because many of listening out there are, say, under the age of 30, of which we have many listeners who are, are going to hear this and maybe not always implement it. It's unpleasant, to do a lot of research before an interview. You say to yourself, 'Well, I'll just answer the questions and I'll sound smart.' But, a lot of times, you know--the famous example, just to stick with football, is, you know, Peyton Manning, when he came out of college and was ready for the NFL [National Football League] draft, a lot of teams talked to him, of course, beforehand, and worked him out or saw him work out. And, the teams that took him, that wanted to take him, were overwhelmingly impressed--the Colts being the team that ultimately took him--were incredibly impressed by the fact that he ran the interview. He asked the questions. He wanted to show--he wanted to know that they were worthy of him, not the other way around. Now, there's an arrogance there that can turn someone off. But, the idea that--you have--just make it simple, in terms of advice: When you go into an interview, as a young person, you want to have some questions. Not just to answer the questions that the interviewer asks. You want to have some questions that you want them to answer for you, about the nature of the job, and what it involves, and whether you'll learn anything; and what are the opportunities for personal growth. And to show that you've done some research on the company in advance. That's really, really important.

Ryan Holiday: Well, I tell a story in my book: The obstacle is the way, the way about George Cluny: George Cluny went to audition after audition as a young actor. And very rarely had much success. And, it wasn't until later in his career that he realized that the audition is a problem for the people giving the audition. That, they want to find an actor for the role. It's not as if they are not going to cast the role. And, so, going into it, realizing, 'Oh! If I present myself as the solution to your problem, rather than the person who is, you know, dying for your approval, that's going to come off very differently, and in fact increase my chances of success.' And I think that's similar to, and that's probably why it works with Peyton Manning, or Nick Saban, or whatever: when they are interviewing him, they are going, 'Oh, this owner, or this GM [General Manager], is desperate to get a head coach.' They don't want to have to interview 97 candidates, and waste a bunch of time. They want someone who can show they have what it takes. And, as you said, it's not how badly you want the job that they are looking for it--

Russ Roberts: 'I've always been a Colts fan,' is not a good argument. But, it's interesting how appealing that argument is. Just to close this part of the conversation: I just want to emphasize this distinction you used in the essay: an addition versus an interview. An interview is someplace where you get asked questions and you answer them. An audition is where you present yourself in as best a light as possible, to make yourself appealing. And I think it's just an, it's a very different mindset going into it. And, it's very useful to think about it that way. I've told this story before, but to me it's worth telling again, of, you know, Fed Ex would interview candidates--supposedly, but it's true--where they'd put 20 people in a room and they'd say, 'We're going to give you half an hour to craft a 5-minute talk to introduce yourself.' And, this is a job interview setting. These 20 people all want to work for Fed Ex. Fed Ex is going to see how they do on their feet and how well they craft their speech. And so, the people immediately start busily taking notes and planning their talk. And then they, one by one, get up and give their talk. And what FedEx does--supposedly--or did; I don't know if they still do it. But, what they do is, they don't grade the people on the quality of their talk. They grade the people on the quality as audience members. They are looking for people in the audience of the job applicants to see how they signal to the speaker that they are empathetic, that they are rooting for them, that they are trying to be helpful. The people--you'd think this was a good strategy--the people who, during the other people's presentations, keep scribbling and polishing their 5-minute talk are actually hurting themselves, because Fed Ex is noting, 'Oh, they are just self-interested. They just want to use this time to the maximum. They don't feel any camaraderie with the other speakers. That's just an amazingly clever thing on every count. I just love that.

Ryan Holiday: Totally.


Russ Roberts: Were you afraid to write this book? I got the intuition at various points that you were a little afraid of it. I was a little afraid to interview you, actually; because there is an ominous power that hangs over the book of things happening in the dark, wheels turning in the background that you didn't want to see, that crush unknowing individuals--and certainly Gawker was steamrolled by Peter Thiel's strategy. Talk about that.

Ryan Holiday: I was, to be perfectly honest. I mean, first I'd be writing a book about a guy that just, you know, destroyed a media outlet because he didn't like what they wrote--on the superficial level. And then it's also a case that has very much radicalized the media. So, the media--it was a delicate line to walk. On the one hand, you don't want to egregiously offend the person who took down the media outlet. But then, if you are at all too positive about that person, the media will attack you. And, also, reputationally, the last thing I want to do is be seen as carrying water for anyone. And so, there were some logistics, some administrative details to nail down. You know, when I was sort of wooing the various sources that I needed to talk to--the conditions that I was willing to give or not give--that was part of it. And also just the delicate subject matter that has been very polarizing. And then on top of that, I was scared just because it's very different from my other books. And, so the fear there was just sort of--failing. What if I can't do the material justice? So, that kept me up at night quite often, as well. It was a really ambitious timeline on the project, as well. So, from start to finish, I would say terror was probably the predominant emotion I felt as I was writing.

Russ Roberts: There are a lot of great quotes in this book, many of them taken from classical writers--Roman, Greek. I think you quoted Thucydides earlier--that's, I think, a first for EconTalk. So, congratulations. But, one thing that struck me--if you'd asked me, what quote would have belonged in this book, I would have said, 'Revenge is a dish best served cold.' Which is a reference to the fact that Thiel--and there's a lot in your book about patience--Thiel waited 9 years, and he probably would have waited longer, to deal this death blow to Gawker. And yet, I'm pretty sure that quote is not in the book--

Ryan Holiday: Yeah--

Russ Roberts: Instead, there are a bunch of quotes I didn't know, which I loved. And part of that is, I think the naive reader of the book will say: You wrote this--you had this lurid, gossipy, X-rated story to tell; and then you decided to add some quotes. So, you looked up 'revenge' in a book of quotations. Or you looked up 'patience' or 'conspiracy'. But I'm pretty sure that's not what you did, because I've read an essay you wrote about how you read. And I would love for you to talk just a little about how you keep track of quotes or ideas that you want to have for later. And, most of us don't do that. I've mentioned on the air that I, until recently--meaning maybe 10, 15 years ago--I never wrote in a book that I read. I keep my books--until 15 years ago, I kept my books literally pristine. Not only did I not write in them, you'd have trouble knowing that I'd read them. I didn't like cracking the binding; I wouldn't open them all the way. And people who opened books flat on a surface or turned them, to my horror, upside down to hold their place--you know, on page 173, which I know eventually cracks the spine and the pages fall out--those kind of things, just--I, I, I, they made me deeply uneasy. But, in later years, recent years, I've gotten better at that. I don't mind that my books are well-thumbed and that I've written in them. And I regret that I didn't write in them more, or do something else. You do something else. Talk about what you do.

Ryan Holiday: I'm looking at my to-do list here for today, and it says: Notes on two books. So, I read; and as I read--I read a lot; obviously it's partly my job--I read a lot, and I fold pages and mark things that I like as I'm reading them. Anything that catches my attention, I mark. And then a couple of weeks later, I sit down and I go back through that book, and I transfer all that material onto 4x6 notecards. And so, today, I'm going to do that with at least two books that I've read--

Russ Roberts: Which is crazy, Ryan! Don't you know that we live in a digital age? Just read 'em in your Kindle and highlight 'em.

Ryan Holiday: No; it's the process for me, of, 1. Marking it down the first time; then letting it marinate; then forcing it to sort of actually transfer it by hand. Although sometimes with really long passages I might type them up. But still, again, having that sort of flow through me: print it out, write it out, put it on a card, then have that physical card--I mean, I'm staring behind my computer is the box of notecards that Conspiracy was built around. And so there's like 18 chapters in the book, then and intro and conclusion; so, let's call it 20 different files. And in each file is the note cards of the material that that part of the, that the sort of raw materials of that chapter. So, quotes, stories, research, things that came up in my interviews, dates on the timeline of this whole, insane series of events. And so, yeah: so, I read very actively; I transfer that information; and then I organize that information. And that's what I build it around. You know, the quote--you mention 'Revenge is a dish best served cold.' I sort of didn't use it on purpose, just because it has kind of become a cliché.

Russ Roberts: Yeah; it's too easy.

Ryan Holiday: Yeah. And actually, I don't know who actually said that. So, I try to use things that I can attribute in one way or another, as well.

Russ Roberts: I'm not cheating here; I've put my phone on airplane mode and I close all my browsers when I'm interviewing folks. I want to say Gore Vidal. I don't know if that's true. We'll find out, and I'll be corrected.

Ryan Holiday: I don't think so. I'm pretty sure it's much older than that.

Russ Roberts: Yeah; I suspect that--well, I bet there's a version that's 3000, 2500 years old, that may not be worded that exact same way, because that sounds Latin or Greek--

Ryan Holiday: That's right--

Russ Roberts: Because it's a pretty deep truth. I think. There is a--the hot revenge--the dish--revenging it yourself quickly is one's first thought. And one's second thought is the point of that quote, which is: Maybe wait a while.

Ryan Holiday: Thinking about that quote for this book, I guess I always thought that 'served cold' meant the actual food item--right, like, that you don't want--like: Is the pizza hot or cold? Right? And then it was only in researching this book and thinking about that quote specifically more deeply, I realized that it's that you don't want to burden yourself carrying the dish. That's the truth of that quote.

Russ Roberts: Hmmm. Oooh.

Ryan Holiday: And I think that's what's so impressive about what Thiel did here, is that he was careful enough--although you could argue there was still some burdening--but he was careful enough that this didn't explode all over him. He had the patience to wait until he was rational to set in motion his plan rather than reacting emotionally.

Russ Roberts: Yeah, that's a really deep insight. Because, you are right--you might be totally right. Because, it could have been worded 'Revenge is a dish best eaten cold.' The fact that it's served cold, it reinforces your point about just letting the explosive aspect of it calm down. But they both could be true.

Ryan Holiday: Sure.

Russ Roberts: But the other point is that, I think revenge is a really bad emotion to harbor. So, it's an interesting question of whether it should be served at all, or eaten at all. To me it's--it's--grudges are better laid aside if you can handle it. Or at least find a way to lay them aside.

Ryan Holiday: Absolutely. And there's sort of one expression--I don't know where this one is from--but, 'When you set out on a journey of revenge, first dig two graves.' So that's one. And then the other is, and this one is from Marcus Aurelius, he says, 'The best revenge is to not be like that.' And I think that that--that's how I personally try to live my life--you know, is that the best revenge is just to not be like the person that you're trying to get revenge on. Because, very often--like--I don't think it was particularly fun to be Nick Denton. Nor would I have wanted to work at Gawker. I think these people were suffering--suffering through their very sins. However, the world--injustice is still injustice, and somebody has to do something about it. So, it's more complicated than just saying, 'Oh, well, I'm not going to be a bad person.' Someone has to do something about bad people.

Russ Roberts: But I do think it's important, when you think about what career to take, to try to find a career that isn't based on a zero-sum game, that isn't based on deception, that isn't based on fraud. And, ideally market forces make those kind of careers not very lucrative, or at least in the long run. But we know that's not true in the short run. There are many ways that people harm other people through their jobs. And, I think, you can get really rich sometimes doing those things. And it's better to make less money doing something else, because--you're digging two graves--that's a different point than you are making with revenge, but I think it's true.


Russ Roberts: Let's close with--the book has been out for, what, a couple of months? A month or two, now?

Ryan Holiday: Yeah.

Russ Roberts: What kind of reaction have you gotten? And what kind of criticism have you received personally, and how are you dealing with them? If any.

Ryan Holiday: It's been really interesting. You know, it was my first book to be reviewed in the Times. It was reviewed in the Post. I've heard from a number of like, really important sort of powerful people that liked it. So, it's been interesting in that sense, just the sort of validation of like, 'Oh, I think I got this right,' and you know, you reached out to me; it was very nice to hear from you. And I was particularly heartened by the fact that you said you didn't think you would like the book and you ended up liking it. To me, that's sort of high praise, for a writer. And then, you know, it's been interesting. It's just so different than my other books.

Russ Roberts: It's like Dylan [Bob Dylan?] going electric. A lot. Well, a little. Maybe not.

Ryan Holiday: I wouldn't make that parallel myself, by preaching[?] it. So, you know, it's just been interesting. You take career risks. And, I think it's paid off in the short term. But how it will pay off in the long term remains to be seen. And so, I'm just, I'm going to put my head down and start the next project. I'm very happy with the book. And I've loved the reactions. And then I'll let the sales be what they are.

Russ Roberts: Have you received any criticism for the way you told the story, that you left out certain things? My impression is that some people have been critical of the way that you framed or that you left out this, that, or the other?

Ryan Holiday: Yeah--

Russ Roberts: Which is inevitable, when you have a book this is--it's a shortish book; it's not a long book. But, it's inevitable that a book of finite length leaves things out. But, what are some of those issues, and how would you respond to them?

Ryan Holiday: Well, clearly there are not many people at Gawker who loved the book. Which was to be expected. I thought it was interesting, you know, that the media loved writing about the sensational elements of the case. But then, I feel like, maybe the book's sort of deeper meditation on the deeper issues got sort of, was too complicated, for, you know, a television appearance, let's say. So, that's been a somewhat disappointing aspect of this. And yeah, there's been lots of criticism. There's been people who were like, 'Oh, you are in bed with Thiel.' Other people, on Thiel's side of things, have said, 'Oh, you are in--how could you defend these people?'--these people being Gawker. So, to me, one of the things I took from it is like, look, if you piss off both sides, that's a pretty good sign that you actually did your job. So, none of the criticism has been, let's say, factual--like, I got the facts wrong. And none of it has been stylistically that I didn't do a good job writing it. And so, if people love it or hate it, that part of it is outside my control, and not what I focus on.

Russ Roberts: So, I want to close with a quote, and you can comment on it and we'll wrap it up. Or you can just let it sit. You say the following--this is a quote from the book:

In a time when computers were replacing many human functions, it will eventually come to be that audaciousness, vision, courage, creativity, a sense of justice--these will be the only tasks left to us. A computer can't practice secrecy or misdirection, a computer can't feel an urge to remake the world.

Only humans can be that crazy.

What you will do with this lesson, what ends you will put it to, are up to you. All I can say is that it is in these times of flux and upheaval that we may need that ambition most.

Ryan Holiday: Yeah. I guess I could just leave it hanging there, because those are sort of the last lines in the book. But, to me, that was the ultimate lesson of what happened here: it was not whether to or should have shut down Gawker or not, but that if you set out to do this crazy thing that everyone warned him against doing, and he did it, to me, is in a weird, perverse way, very inspiring. And, again, I think we are staring in the face of a lot of issues that we have come to despair solutions to--whether it's the education thing that you were talking about, or maybe it's the Second Amendment, or maybe it's our economy. Whatever it is. We're sort of butting up against these walls. And I don't want people to go, 'Oh, there's nothing you can do about it. Let's do nothing.' I'd like them to think more creatively and more ambitiously about what they can do about it. And to me, that was the lesson that I tried to conclude the book with.