The Art of Manliness - #412： The Power of Conspiracy and Secrets

00:00:00.000 brett mckay here and welcome to another edition of the art of manliness podcast back in 2016 a

00:00:19.240 bizarre story emerged in pop culture professional wrestler hulk hogan won a 115 million dollar

00:00:25.780 lawsuit against the gossip website gawker for publishing a sex tape of him that had been made

00:00:30.420 without his consent the victory was somewhat surprising but the real surprise was who is

00:00:34.720 actually behind the lawsuit it wasn't hogan himself but the billionaire founder of paypal peter teal

00:00:39.920 teal had his own axe to grind against gawker and had been honing it since 2007 in fact he had been

00:00:44.780 plotting to take down gawker for almost a decade and what may sound like a tawdry story of celebrity

00:00:49.640 and scandal actually contains surprisingly potent lessons on revenge stoicism strategy perseverance

00:00:55.380 hubris privacy and the underrated power of secrets my guest today dug into the story and its insights

00:01:00.600 in his new books conspiracy peter teal hulk hogan gawker and the anatomy of intrigue his name is

00:01:05.440 ryan holiday had him on the show several times he's the author of growth hacker marketing the

00:01:09.400 obstacles the way ego's the enemy in the daily stoic today on the show ryan and i discuss his

00:01:13.780 latest book and the lessons we can take from a story that reads much like a modern day count of

00:01:18.100 monte cristo after the show's over check out the show notes at aom.is slash conspiracy ryan joins me

00:01:23.520 now via clearcast.io all right ryan holiday welcome back to the show yeah thanks for having me it's

00:01:40.800 been uh it's been a while so yeah it's uh this is a three-peat for you i think you're one of the is

00:01:45.820 that a record well no it's not a record but like there's like it's it's exclusive company i think

00:01:51.340 there's like okay two or three people who've done the three-peat i'll take it well you got a new book

00:01:55.860 out it's called conspiracy peter teal hulk hogan gawker in the anatomy of intrigue so this is a book

00:02:04.160 about one of the most bizarre legal cases in american media history and i'm we'll get into the

00:02:10.200 some of the details later on for those who aren't familiar with it but i'm curious how did you end up

00:02:15.280 being the guy who sort of wrote the history of this weird case involving billionaires a millionaire

00:02:22.820 media mogul and the hulk well how'd that happen i in some ways i have i have no idea it caught me

00:02:30.820 as much by surprise as i think it caught anyone else in some ways i think it's you know a little

00:02:36.160 bit of right place right time but to me it's also this is why you put yourself out there and you take

00:02:41.280 risks and you try to write about different things that i i've written pretty extensively about media

00:02:47.220 over the years and i wrote a column about this case because i was following it in the news just the

00:02:52.180 the idea of this billionaire plotting in secret for 10 years to get revenge was was my initial take on

00:02:59.600 what had happened and i wrote this article about it and peter teal who was that billionaire sent me an

00:03:04.620 email about it after and so he and i started talking and then i wrote a column about

00:03:10.500 why people should stop watching the news how we consume way too much news and i sort of took a

00:03:15.840 philosophical take on this and then i got an unsolicited email after that from nick denton who

00:03:21.660 was the founder of gawker who was the company teal had taken his revenge out on and so i was sort of

00:03:29.340 thinking about doing a book and then i had access to both these two principles it occurred to me i'm

00:03:34.480 probably i was probably the only person on the planet talking to these two mortal enemies

00:03:39.200 and then i just sort of floated the idea to my publisher and it was it was off off to the races

00:03:45.960 and it was really intimidating and scary obviously not having written in this sort of narrative non-fiction

00:03:51.500 form before and you know writing about a guy who just bankrupted a hundred million dollar company he

00:03:57.220 didn't like and you know it was so scary in a lot of ways but to me mostly that those are the

00:04:02.540 exactly the kind of projects you want to take on as a writer and so all those things kind of came

00:04:07.300 together and the book as a result of that and how did you approach this book because okay we'll get

00:04:11.980 into like it's about a sex tape right and so it'd be easy to be just focusing on that and the sort of

00:04:17.880 details of that but you didn't do that you you you seem to take a more of a philosophical approach and

00:04:24.260 how you retold a story and also like what we can learn from it well one of the weird things because

00:04:29.980 this has obviously been an intensely reported story and involves silicon valley and new york media and the

00:04:35.900 media itself and the first amendment and a professional wrestler you know it's it's all

00:04:40.140 these things so it's been covered by journalists a lot and what i felt like they fundamentally got

00:04:44.520 wrong and i think we see this across the board with a lot of media coverage and you know when when

00:04:50.500 people watch sports and have comments or when they follow politics they have comments people want

00:04:55.540 to argue with other people's motivations right so you know peter teal said he did this because he thought

00:05:03.280 it was about justice and it was about you know improving the world and then everyone in the media

00:05:08.940 said no that's not true you did this because you know you were afraid or you were evil or all these

00:05:15.320 things and you can't it's like if i tell you brett that i'm offended you can't argue with me over

00:05:21.520 whether i'm offended or not but what you can do is take the time to figure out why i feel the way that

00:05:28.440 i feel and so what i try to do in the book ultimately and this was a stretch for me as just

00:05:33.120 a human being who had preconceived notions myself is like okay why did this guy who who's worth billions

00:05:40.140 of dollars who could do anything he wants with this time who's founded these enormous companies you know

00:05:45.220 paypal he's a first investor in facebook he's a founder of palantir why on earth would he have spent

00:05:50.880 all this time on this thing it must have been really important to him and he must have had some

00:05:57.220 sincere motivation so i'm going to ask him and i'm going to figure out what that is and i'm going

00:06:02.280 to try to express it as vividly and as deeply as he feels it and then on the other hand it's not as

00:06:10.160 if gawker and and we'll sort of i guess sort of drop in little hints of the story but the the reason

00:06:16.740 teal and gawker were opposed to each other is that a gawker writer in 2007 had outed teal as gay

00:06:24.400 now when gawker wrote this article they weren't thinking what's the the cruelest meanest scummiest

00:06:31.840 thing that we can do they were thinking that this was important that this was newsworthy like they had

00:06:38.040 their own motivations there's this line from socrates where he says nobody does wrong on purpose

00:06:42.960 and so one of the premises of the book for me was like let's figure out why everyone did what they did

00:06:50.020 and try to explain it and once we once we lay this all out then the reader can judge who's the good

00:06:57.800 guy or the bad guy i think too much of what we see and read and hear these days is designed to tell us

00:07:05.360 how other people feel rather than get you know rather than get to the truth of that actual feeling

00:07:11.760 if that makes sense yeah that makes sense all right so let's get in some of the get some background

00:07:15.260 for this okay because i want to delve into some points but i think it's important for we got we

00:07:19.360 got to understand that that's sort of the story uh so you mentioned uh there's a website called gawker

00:07:24.440 2008 published an article outing peter teal as gay we'll talk about gawker i mean what what for those

00:07:31.820 who aren't familiar with gawker what is gawker and what sort of websites do they run gawker starts as

00:07:36.780 a blog in in nick denton's living room the first one is about tech gadgets the second is about gossip

00:07:43.060 and it very quickly just explodes tens of millions eventually billions of pages a month and a year

00:07:50.280 and it is a website that sort of revels in being an outsider and revels in critiquing and holding

00:07:59.080 powerful people to account that's how they see it now a couple tweaks on that so one gawker loved to

00:08:06.640 write the stories that other people wouldn't write so if there was a if there was a rumor that someone

00:08:11.800 else was you know didn't feel had been verified gawker would that's that's the kind of story that

00:08:16.720 gawker would love to run if if someone had stolen something and was trying to leak it to the media and

00:08:22.500 the media was like well i don't know where this came from that's the kind of scoop that gawker wanted

00:08:27.500 and then on top of this gawker was the website that pioneered the the strategy of paying their

00:08:33.940 writers at least in part based on how much traffic their articles do so is this explosive

00:08:39.180 controversial media company that starts really small it stays independent and then it becomes

00:08:44.740 incredibly powerful by writing the kinds of gossipy dark no holds barred stories that that readers love

00:08:53.080 to eat up all right so and then 2008 they wrote it just sort of an offhand article peter teal is gay

00:08:59.380 yeah in two in 2007 they published an article and the headline was peter teal is totally gay people

00:09:04.760 and it's an anonymously sourced article that that that posits that peter teal who is essentially

00:09:10.800 an unknown person outside silicon valley at that time is is not only gay but nick denton speculates

00:09:18.240 at the bottom of the piece that there's something that why is he so secret about it what is he hiding

00:09:24.080 why is he ashamed of being gay and this is teal's rude introduction to this media company and how they

00:09:32.280 work and also you know denton is also gay so that was kind of denton is gay and the writer who writes

00:09:37.760 it is gay and and and this is actually sort of an mo of gawker they they they outed they were one of

00:09:43.780 the first to report that anderson cooper was gay they've they've outed a number of other people and

00:09:48.720 t and denton would say that he believed that it was only out of a misplaced sense of decency

00:09:54.320 that media outlets refused to do what gawker was doing so it it is a strange contrarian unusual

00:10:03.120 worldview that denton and gawker has and that's what puts them on this collision course with teal

00:10:09.640 so okay teal got out and he didn't like that i mean what why why is that because like this is 2007

00:10:15.380 it's the 21st century you know acceptance of homosexuals is you know pretty mainstream at this

00:10:21.240 point why was teal so why did this we got to go back why is it we got to go back in time i mean

00:10:25.760 you know prop eight which bans gay marriage in california hasn't even been passed yet it that's months

00:10:32.020 in the future you know like obama obviously hasn't been elected in 2007 and he himself and hillary

00:10:38.720 clinton neither of them have come out in favor of gay marriage so it's it's it it is not what it is

00:10:46.080 today back then but i think primarily what teal objects to is why the hell is this anyone's

00:10:52.740 business like uh i don't know the sexuality of any of the other early investors in facebook

00:10:57.860 and i think his point was what why are you writing this about me what did i ever do to you and and

00:11:04.560 even if you are writing it about me why are you writing it in such a cruel and mean way why are you

00:11:10.660 implying that there's something wrong with me for wanting to keep this private piece of information

00:11:17.560 private and so he stews on this you know he doesn't do anything right away he can't it's not

00:11:22.860 illegal to out someone it's certainly in bad taste but it's not illegal and so for for the next several

00:11:29.160 years literally years he just sort of despairs of being able to do anything about this he meets

00:11:35.100 scotker writers and he asked them and he asked them about it he he talks to a sort of a notorious

00:11:40.840 new york city sort of fixer a lawyer and and pr genius and they're basically like look this is the

00:11:47.200 new reality for you you are going to be a target for these websites you've just got to take it

00:11:52.860 until he just doesn't like that and he doesn't he doesn't want to have to accept that so he stews on

00:12:00.580 it and he kind of i think he kind of resigned to himself to the fact that there's nothing he could do

00:12:04.280 about it because you know gawker could always claim first amendment right yes and that was and it's a

00:12:09.580 big protection for them so totally and and right rightfully so right i mean the it is the media has

00:12:16.180 special protections and centuries of precedent protecting its right to do what it had done to

00:12:23.480 teal and it's so it's not until 2011 so four plus years later that teal has a dinner in new york city

00:12:31.640 with a young man teal obviously as an investor is always looking for sort of ambitious young people

00:12:37.480 who he can place in startups or invest in and he meets with this this kid really i call him mr a in

00:12:43.560 the book he is not yet been identified and mr a essentially pitches to teal he says look i know

00:12:49.960 what gawker did to you was was was upsetting but not illegal but here's the thing i think they may have

00:12:56.800 done other things that more clearly cross various legal lines maybe it's copyright violations maybe

00:13:04.340 it's invasions of privacy it's intentional infliction of emotional distress you know maybe

00:13:10.160 it's defamation maybe it's libel maybe they've done other like a website that would push the boundaries

00:13:15.860 so far in what they did to you may have pushed it more egregiously so in other instances and he says

00:13:22.260 i have a plan i have a legal firm i think we can work with and i think with about a 10 million dollar

00:13:28.620 budget and three or five three to five years of runway i think we can take these people down and and

00:13:34.800 he says i think the world would be a better place if you did this and teal says to him look i've i've

00:13:40.780 thought about this there's nothing you can do about it and mr a looks him in the eye it's incredible

00:13:46.500 that this 26 year old kid would do it and he says um peter it if everyone thought that way what would

00:13:53.860 the world look like and that's sort of exactly what teal needed to hear and he he ends up backing

00:14:00.040 what i call a conspiracy for the next five years on the spot he basically gives him a an unlimited

00:14:08.180 budget and says uh let's do this okay so there's a lot there's some stuff that's some great stuff

00:14:13.300 we're gonna unpack which some of the stuff you just talked about how did they end up representing

00:14:18.560 or paying for the whole colgan case so how did they connect there so so teal's again though teal

00:14:25.560 puts up this money but it's not money that's gonna win win this sort of war against gawker what teal

00:14:33.600 knows is that he needs the right case right if teal had thrown 10 million dollars again litigating

00:14:38.840 his case against gawker that they'd outed him he would have lost and so what he and mr a do and

00:14:44.700 the lawyer that they ultimately hire and his team do is they begin to troll through gawker's archive

00:14:50.800 to find examples of it potentially violating laws in various places and they don't find anything that

00:14:58.240 immediately stands out and they do this for about a year and it's not until october of 2012

00:15:04.440 that gawker runs a stolen sex tape of the professional wrestler hulk hogan that had been

00:15:10.440 recorded without hogan's consent by his best friend of all things uh that that they realize

00:15:17.780 that that they may have the case of a lifetime here and so again i know some of these sensational

00:15:24.200 details might just seem like uninteresting to people or unimportant but i think what i tried to do in the

00:15:29.640 book and what i think is so important about what teal did here is that he didn't just rush into this

00:15:37.040 first he waits then he assembles the right team but then most importantly he waits for the right

00:15:42.280 opportunity and you know he said to me that that capital wasn't the the scarce resource it was having

00:15:48.980 the right creative idea and so he has his patience to wait literally like several years until this

00:15:56.120 hulk hogan opportunity comes his way that that then they're able to file a hundred million dollar

00:16:02.300 lawsuit on hogan's behalf gawker has no idea that teal is responsible they totally laughed the case off

00:16:08.560 but it'd be it's because teal had the patience like a great investor to wait for the right opportunity

00:16:15.080 that he's able to put himself in a position to win okay so yeah they end up winning the case yes let's

00:16:20.880 talk about like the lessons from that that's what i love about this book it was sort of like um you know

00:16:25.960 something like machiavelli or plutarch would write right they take these like just these you know

00:16:31.160 stories of intrigue and like what can people learn about this about being about morality about strategy

00:16:36.740 etc let's talk about you've written that peter teal is a high agency person what do you what do you

00:16:44.420 mean by that what are the attributes of a high agency person well i'm honestly it's very flattering

00:16:49.000 to me that you said plutarch because that was sort of a model for me writing the book you know

00:16:53.920 plutarch has this this series called parallel lives where you know he sort of contrasts and compares

00:16:59.840 really epic people like a cicero and a caesar and in some ways i feel like nick and peter are people

00:17:06.340 like that so that that's what i tried to do in the book and a high agency individual is also like

00:17:12.420 those epic characters from history that we love i think would fall in that category the phrase comes

00:17:18.440 from from someone who works with peter a guy named eric weinstein who's this sort of brilliant

00:17:22.980 mathematician and and economist and he says that you know there are people who when they hear no

00:17:29.180 accept that they've heard a no and then there's people who hearing no begins a very different

00:17:35.660 conversation for them that they try to see what can be done they don't accept that no and i think teal

00:17:43.620 and mr a are good examples of that originally you know teal said it took him a while to get there to be a

00:17:49.860 high agency person but when he he just doesn't like being told that there's nothing you can do

00:17:56.260 about this situation and i think that's why he stews on it for so long and why he lights up when he

00:18:01.420 hears mr a's plan because he's like oh i don't have to accept this and if if everyone in the world

00:18:07.900 accepted everything that they didn't like things would never change and they would certainly never get

00:18:13.100 better and so he he seizes on this slim but ambitious plan to do something about gawker

00:18:22.620 because he's a high agency individual who does not want to resign himself to the status quo and how do

00:18:29.360 you think you know one becomes a high agency person like there's something about teal's background that

00:18:33.540 is it genetic is a temperament upbringing or can you actively decide like i'm just gonna not take no

00:18:38.680 for an answer no matter what yeah that's a good question i mean look entrepreneurs are by definition

00:18:43.560 high agency individuals like you're trying to make something where there isn't a thing before so that's

00:18:49.760 part of it but i think it's it's about practice you know teal had started one company he'd started

00:18:55.240 another company he'd started a third company he'd done this and he so he'd experienced many times in

00:19:02.360 his life people telling him that things were the way they were for a reason and that they couldn't

00:19:08.440 be changed and that it was impossible for a little guy to beat the big guy or for you know this person

00:19:14.880 to do this or that and so i think he he'd slowly built up this sort of reservoir of confidence that

00:19:21.900 told him i don't have to listen to these people you know he he has a quote that i i have in the book he

00:19:27.760 was talking about he's like actually i'm not that worried he's like i'm not that interested in things

00:19:33.180 that people don't don't think are possible right he's like that those things are kind of interesting

00:19:39.200 to me he's like what's really interesting to me the things that i think i'm really right about

00:19:44.320 are the things that other people aren't even thinking about at all and so what was so incredible

00:19:49.680 about this conspiracy is that no one it's not like people suspected that something was behind it

00:19:56.320 and they just didn't know who it's that literally no one even considered something was happening

00:20:03.220 myself included you know one of the gawker editors uh says this he's like we scarcely could have believed

00:20:09.600 that something so conspiratorial could have happened and of course that's exactly why it happened and so i

00:20:15.700 think teal specializes in finding the things that other people don't think are are are viable and that's

00:20:24.100 what he bets on and ideally he wants to be underestimated or not even considered at all

00:20:30.180 because that's where the really big opportunities are yeah that's uh that goes counter to how a lot

00:20:35.260 of people approach success in our modern world like they want as much attention as possible but teal

00:20:41.220 likes to fly under the radar yeah you know he he has a line i think a lot of us sort of gravitate

00:20:47.280 towards where there's competition right lots of people want to be professional football players so we

00:20:51.920 think that would be fun or we hear you know lots of people go to harvard so we want to go to harvard

00:20:57.700 because it must be good because a lot of people want to go there and i think teal's point you know

00:21:02.880 teal has this line in his book zero to one which everyone should read even if you don't like peter even

00:21:07.900 if you disagree with him and he says competition is for losers and i love that line because it's true

00:21:14.400 you know what you ideally want to do is find where there's no competition where you're the only one

00:21:20.140 you know when you launched uh art of manliness it's not like there was 500 other art of manliness

00:21:25.760 website you know manliness websites and you were just 10 000 times better than them it's that you

00:21:31.660 were the only one and so what's interesting now is like someone might be listening to this and they

00:21:36.120 see what you're doing and they're like oh i'm gonna make a website about how to be a man or how to be a

00:21:41.120 better man and that's that's actually the wrong lesson what you should do is find something new or

00:21:47.020 different that was as new and groundbreaking as art of manliness was when you started it and

00:21:52.800 and so that's what i try to do with my books and i think that's what teal tried to do with this

00:21:57.420 conspiracy he tried to do the thing that no one even thought was possible right yeah so that

00:22:04.060 competition is for losers he makes a point that's a good point about strategy right because um

00:22:07.600 competition is costly yeah you have to spend a lot of money out competing your competition

00:22:12.720 competition in war war is extremely costly you know it's like lives and money but like but the

00:22:18.700 conspiracy thing like okay let's talk so this is basically a story of revenge because i thought

00:22:22.780 it was interesting when i was reading this i was like man this is just like the count of monte cristo

00:22:26.440 yeah and what he did was an act of competition like he had to spend a ton of money sure a ton of

00:22:33.880 bandwidth and a ton of so like how does that jive with his idea competition is for losers

00:22:38.620 and here he is is you know secretly but he's he's competing that's true but but let's think about it

00:22:45.760 the difference between say a war and a conspiracy right so sometimes conflict is inevitable right

00:22:51.460 two people have two competing visions or two people are jockeying for something and so one of

00:22:57.340 them only one of them can be victorious so machiavelli talks about this he says look only the really

00:23:02.880 powerful or the reckless can afford to go to outright war with each other right like two

00:23:08.400 armies in the field clashing but but machiavelli says a conspiracy is more secretive and effective

00:23:15.900 and can be wielded by anyone and so what teal didn't do is sort of announce that he was going

00:23:23.600 after gawker and that he was going to destroy them and he didn't you know nick denton said this to me

00:23:29.120 he's like why didn't teal just write about what his his critique of us and start a conversation about

00:23:35.260 it and teal's point is that that wouldn't have worked that's why he didn't do it what teal said

00:23:40.540 was i'm not going to let them know that i'm coming for them for them i'm going to operate in secret

00:23:46.260 i am going to find a weak point or an undefended you know sort of chink in their armor and that's

00:23:53.960 where i'm going to plow all my resources and so in some ways it's like um you know it's like finding

00:23:59.980 the the the exhaust vent in the death star you're not trying to win a war of attrition necessarily

00:24:06.020 or you're not trying to to just match strength against strength you're trying to put strength

00:24:11.980 against weakness and so what teal did here again first off by just not even pursuing his own case

00:24:18.820 but by pursuing other cases he's already put gawker at a disadvantage because they don't know who

00:24:24.060 they're fighting against but then he looked for the most egregious violations that they'd made

00:24:29.620 and he did it in things that they didn't expect to be attacked for like if you're a celebrity and a

00:24:36.260 stolen sex tape of you is run on a website the last thing you would rationally do is sue about it

00:24:43.180 because you're only going to draw more attention to it and and so what teal did by sort of taking care

00:24:49.720 of hulk hogan and said look you don't have to spend a dollar of your money here and you can keep all the

00:24:55.500 winnings if you win you just have to let me back this on your behalf he was catching gawker off guard

00:25:01.700 because they didn't think hulk hogan was going to go the distance on this hundred million dollar lawsuit

00:25:06.340 they just assumed he would settle at some point and then this would all go away so say on this idea

00:25:13.100 of revenge this isn't because you you've you've written a lot of books about stoicism that's we've had

00:25:17.940 you on the podcast talk about stoicism and the stoic would probably tell peter teal well you know

00:25:23.520 if someone writes this mean thing about you and you just ignore it right like you don't have any

00:25:28.180 control over that just move on with your life but he didn't like sure no no that that's a great point

00:25:34.740 and and you're absolutely right the stoics would would say that i mean marcus aurelius has a great

00:25:38.800 quote he says the best revenge is to not be like that right to if you think what gawker did was

00:25:44.360 disgusting and vile your best revenge is just to be a better person and so but again this goes to my

00:25:50.540 original point is i'm not arguing with what teal felt or whether he should have felt that or not

00:25:56.540 he felt that this was deeply wrong and and you know the stoics are also advocates for justice and and

00:26:04.820 and i think what teal felt ultimately was that what gawker did to him and to other people

00:26:11.640 wasn't simply mean or hurtful but was genuinely wrong and needed to be stopped and so i think he

00:26:19.380 told himself that this was this quest of good against evil and i i don't make any judgments about

00:26:25.380 that because that's what he felt and we should try to understand what he felt just as we should try to

00:26:30.140 understand what gawker felt however what what i think that quest allowed him to do was rationalize

00:26:39.840 this partly revenge part this partly this quest of revenge and allowed it to make it bigger than

00:26:46.740 himself so he didn't have to stop and think hey am i doing this for me or is this actually about other

00:26:53.780 people and and look revenge is very dangerous i mean look two two famous expressions about revenge

00:27:00.400 you know revenge is a dish best served cold you know we think that's about taste but the more that i

00:27:05.940 thought about it it's that the dish is hot you don't want to touch the dish right you'll burn yourself

00:27:11.660 and so you need that patience and so that was one of the things that teal had but the other famous saying

00:27:17.120 about revenge is if you set out on a journey of revenge first dig two graves and there's a cautionary

00:27:25.100 element of that story for in this story for that reason i mean teal sets out to to fight this battle

00:27:31.000 for his privacy and he ends up becoming more famous as a result and he ends up you know doing i think

00:27:37.640 some things you could only charitably describe as it's quite dark as in in pursuit of this revenge

00:27:45.260 so it was not without cost to teal either and that's the thing if you're thinking about revenge

00:27:51.660 you've really got to weigh those costs and and benefits because it might not be as satisfying as you

00:27:57.740 think right yeah there's that other line too about be careful who your enemies are because you end up

00:28:02.120 like them or something like that yes yeah and that that was something that one of teal's friends told

00:28:07.320 him and he you know he obviously pursues it anyway but you know there's an argument to be made that in

00:28:12.700 some cases teal and gawker just switch places at the end of the story like at the end you know teal is

00:28:19.940 the powerful one who destroyed someone who uh you know embarrassed and humiliated them the you know

00:28:27.780 there's also the quote uh those who fight monsters must be careful that they do not become a monster

00:28:33.520 and and that so that that's what's so epic about this story and and i think we should remember you

00:28:39.580 know when you read history when you read plutarch or machia valley or or or even homer like the iliad and

00:28:45.320 the odyssey none of the characters are fully good or bad they embody these sort of larger than life

00:28:51.740 traits that we're supposed to learn both what to do and also what not to do and i think there's a lot

00:28:58.320 of that in peter and i definitely think there's a lot of that of of gawker and nick denton you know

00:29:03.500 hubris is probably the main theme on both sides through this book yeah how do you think how do you

00:29:09.760 think i mean gawker's obviously hubristic because they just thought they could do anything and get away

00:29:13.320 with it i mean how did teal display hubris well first i mean he thought he could get away with

00:29:19.060 this right like he not not only did he think he would never get caught at the end as this case was

00:29:25.280 sort of winding towards its verdict and it became very clear to him that they were going to win he

00:29:30.320 still ends up pursuing other cases several other cases on behalf of other clients against gawker that

00:29:37.900 are so sort of over the top and much less legitimate i would say like appear to be much

00:29:43.480 less legitimate than the other than the gawker case and and enough of this happens in a small

00:29:48.780 amount of time plus peter has begun to loosen his lips right he starts telling privately like other

00:29:55.980 people that he's been doing this and eventually all of this contributes to his identity being revealed

00:30:02.460 after the verdict like he could have gotten away with this had he been had had his discipline not

00:30:10.020 relaxed even just a you know a half breath the way that it did perhaps he would have gotten away with

00:30:17.280 it and and i think he regrets that yeah i mean i think a lot of war strategists have said that the

00:30:22.500 most dangerous time in war is at the point of victory and yes that's what happened here yeah i mean

00:30:28.340 robert green talks about this you know do not go past the point that you aimed for and i think teal

00:30:34.860 you know teal wanted to win a knockout blow against gawker but ends up you know piling on after and

00:30:41.860 actually i would talk to holt kogan about this and he would say look that's a lesson that i learned in

00:30:46.220 wrestling is you're winning but if you beat up too much on the other guy the crowd turns on you

00:30:52.820 and the the hero becomes the villain and i think that's part of teal's story i mean look he's a

00:30:58.960 billionaire and he kind of likes you know controversial contrarian things so i don't think

00:31:04.120 it's like keeping it keeping him up at night but you know i do think it would have been easier and

00:31:10.760 better for him had he managed to get away with this entirely and and part of the reason that he

00:31:16.820 didn't is that he just told one too many people because he was so proud of it yeah well so this

00:31:22.540 this book is called conspiracy you call what teal did it was a conspiracy because okay conspiracy is

00:31:27.740 it's a it's a legal term right it's it's something that's done in secret when there's more than one

00:31:31.780 person involved yeah so i mean and i think it's typically something that's like disruptive right

00:31:37.480 like you don't conspire two friends don't conspire to go get ice cream right but you might you know

00:31:42.980 you might conspire to get a the mayor of your town impeached or you might conspire to you know

00:31:50.260 start a protest for civil rights you know like there there are things you can conspire to do

00:31:56.080 they're typically disruptive that's not to say positive or negative but they are disruptive so

00:32:01.640 yeah but we live in a society an age that puts a premium on transparency right we don't like

00:32:07.560 secrets right but you know from reading the book i mean you kind of get the impression that wow no

00:32:12.780 secrets can actually be very powerful a powerful tool in getting things done why why is that why why

00:32:19.460 are secrets so good and getting like why was teals obsessed because it seems like he was a very

00:32:24.000 private person right what what's his background that made him think that privacy secrecy not being

00:32:31.860 fully transparent actually could help you get more stuff done well you know there's this line from

00:32:36.640 napoleon where he says never do what your enemy wants you to do for the reason that they want you to

00:32:42.820 do it right like if someone says you should do something it's probably better for them than it is for

00:32:48.580 you and so i think one of the interesting things about secrecy is the fact that people don't want

00:32:53.400 you to keep secrets is probably evidence that there's something powerful or valuable in secrecy

00:33:00.360 right and so i think teal's point is like why would i tell gawker that i was coming for them if that

00:33:06.540 would make it easier for them to defend themselves you know and we see this now in this social media

00:33:12.440 world that we live in it's like you have to tweet about every freaking thought that you have you know

00:33:17.440 the idea like like people for instance are always asking me it's like what's the next book that

00:33:22.620 you're working on it's like why would i tell unless there was a clear marketing purpose because it's

00:33:28.520 done why would i want to alert my competition that of what i'm working on and give them a chance to

00:33:35.460 beat me you know or give them a chance to undermine my argument or be prepared to undermine it and so i

00:33:42.420 think part of what secrecy is is about planning and trying to do something ambitious enough that

00:33:49.700 there are going to be people who want to stop you and those are precisely the people that you want to

00:33:54.100 keep your secrets from and so i think that that is one element of it the privacy element i think is

00:34:00.420 is is related but distinct i think teal's point about privacy is that look we've got to give people

00:34:07.080 room to have controversial thoughts to try different things to be different or weird you know what of

00:34:14.440 what gawker did was sort of was a was a a non-discriminating hater right like they would make

00:34:22.380 fun of anyone for anything so if you tried something and failed gawker loved that because they would make

00:34:28.880 fun of you for it if you had a weird belief gawker would make fun of you for it if you i don't know took a

00:34:35.200 risk and tried to you know do something different in you know with your clothes gawker would make fun

00:34:40.580 of you for it if you tried to explain yourself about some controversial issue and you failed

00:34:45.520 gawker would nail you for it and so all of this is this sort of intense scrutiny and criticism of

00:34:51.860 people instead of giving them space to experiment and try things and i think that has a a societal and

00:35:00.320 cultural cost of making us more conservative and risk averse and it also prevents you know the the

00:35:08.340 way to have good ideas is to have lots of bad ideas right but if we if we mock and criticize everyone

00:35:14.520 for every bad idea and conversely if we tweet every bad idea that we have we're not going to have the

00:35:22.060 space that we need to filter the good from the bad right yeah because people won't let you live it

00:35:26.740 down i mean that's the thing i've noticed right they'll always remind you that your bad idea

00:35:31.000 and it'll dog you for the rest of your life yeah and and then people who are afraid of that will stop

00:35:37.160 even trying at all and it's very i think teo's point is it's very hard to measure what we lose because of

00:35:44.220 that but it's probably very very costly you know like we want we say we you know we admire someone like

00:35:52.560 elon musk but we don't really create room for there to be more elon musks because we we we hit

00:36:01.020 them so hard early on in their career before they become elon musk that we prevent that from ever

00:36:06.800 happening yeah well the other problem i mean one of the problem with conspiracies is that you have

00:36:12.780 conspirators that are in on the secret right would have been franklin say like once like two people

00:36:17.820 know about secrets no longer a secret right how did teal keep the funding of his lawsuit a secret

00:36:24.920 for so long like you know you had hogan and that could have just bailed on us at any moment he had

00:36:30.180 all these people who knew about it but they didn't disclose like how how did he keep that that sort of

00:36:35.860 um that tightness um for and in the group for so long well that that's a great point because it it

00:36:41.580 also helps you realize like why most conspiracy theories aren't true you know like when people talk

00:36:47.300 about you know it was 9-11 an inside job the amount of people that would have had to be in on that

00:36:52.360 conspiracy for it to be real is just so improbable that it can't possibly have happened but in this

00:36:58.520 case what teal did was teal hired mr a mr a hired charles harter who's the lawyer and charles harter

00:37:07.220 solicits representing hulk hogan so so there are all these layers that are obscuring who's really behind

00:37:15.680 it so the lawyer and hulk hogan both uh are in the dark about who is actually funding this lawsuit

00:37:23.600 they just know that a business person is funding so that was their secret but they didn't even know

00:37:30.180 the secret they were keeping they didn't even know the full secret that they were keeping and i think

00:37:35.140 that was a big part of it like you know let's say you have a company and you have this larger strategic

00:37:40.820 vision obviously certain people in the company need to know it but not everyone in the company

00:37:46.320 needs to know everything about it right down to the the doorman doesn't need to know everything that

00:37:52.980 you're doing and you know apple for instance is a very secretive company and that's part of how they

00:37:57.900 managed to surprise us with all these amazing products is that news isn't getting out as it's

00:38:03.240 happening and so we don't have super high expectations each time we're we're kind of caught off guard we're

00:38:08.400 like wow i didn't even know that i wanted that and then so so secrecy is important for a lot of reasons

00:38:13.620 and there's a lot of ways to do it you know there there's this line from a from a roman general that

00:38:19.180 i quote in the book and one of his men says you know what time are we moving out tomorrow you know

00:38:25.360 are we marching and the general says if my shirt knew the answer to that question i would burn it

00:38:31.240 right like he's like no one is going to know except me and that's going to give us an edge over our enemy

00:38:37.180 because the more people that know the more likely it is that the enemy will find out

00:38:41.580 so how did this how did all the players in this story turn out like what happened to denton like

00:38:47.180 he lost his hundred million dollar company yeah a 300 million dollar okay 300 million that's that's

00:38:53.400 a big deal it's like what happened to him so so right so the verdict comes back it's 140 million

00:38:58.380 dollar verdict it bankrupts the company they have to sell it off denton denton leaves the company

00:39:04.100 the sort of two interesting players are are nick who's the owner and founder of the company

00:39:08.540 and then a guy named aj delario who is the editor who ran the story of the the hogan sex tape and

00:39:15.720 what's so interesting about them you know what i say in the book is that although teal wins there's

00:39:20.880 very very rarely much character in winning right like winning sort of doesn't often make you better

00:39:27.100 but on the other hand denton and delario lose everything and there often is a lot of character

00:39:33.760 in in losing everything because it forces you to question so many things and and one of the weird

00:39:40.840 twists of the story and and why i was motivated to write the book is that it turns out that both

00:39:45.900 denton and delario turned to stoic philosophy and and actually happened to have read my books because

00:39:52.580 they were they were looking at how to sort of pick up the wreckage of their lives and move forward

00:39:58.020 because that's the only thing that you can do and so you know aj uh ends up you know going into recovery

00:40:04.580 and and and and and gets clean and sober and he has a family now and he's trying to sort of rebuild his

00:40:10.760 life as a writer and then you know it is it gotten married and is thinking about starting a family

00:40:17.000 and has moved to europe and it's just sort of exploring what he wants to do next but what i

00:40:22.340 think is so remarkable is even if you think that they deserved what happened to them it would also

00:40:27.840 follow that both of them would be bitter about the experience i mean to have been destroyed by this

00:40:32.780 person who is so much more powerful than you over something you totally forgotten that's a bitter pill to

00:40:38.700 swallow and yet neither of them are and and i think that's to their credit both of them are are are resilient

00:40:45.500 strong people who just said look i'm i i can't control that this happened to me i'm not going to

00:40:52.220 let it ruin my life i'm going to move on and i'm going to do something next and that that's where they

00:40:57.860 they both are and look to a certain degree we we have to give a little bit of credit to peter

00:41:02.140 and that peter was willing to settle and let this thing go you know he wasn't he didn't want to salt

00:41:08.480 the earth after his victory or destroy them completely he was willing to let them move on and so i think

00:41:14.940 if there's any happy ending in this it's that you know everyone has sort of moved on to to to

00:41:22.000 whatever they're going to do next did teal and denton ever meet face to face after this thing

00:41:27.300 happened they they did it was i mean just the idea of that is so insane that both these men who'd spent

00:41:32.760 tens of millions of dollars fighting each other that one had destroyed the other in court the other

00:41:37.440 had humiliated the other in in the in the media and they end up meeting after the verdict because

00:41:43.820 you know even though it was a large verdict eventually you know these things can be appealed

00:41:48.360 and fought and and they can drag on for years to the point where no one actually gets the money it's

00:41:53.960 like the the saying is that the lawyers are the ones who always win and uh teal and denton meet they

00:42:00.160 meet first at the house of a friend and then later again in a conference room in new york city

00:42:04.140 and they kind of they hash this thing out and they say you know both of them are very suspicious of

00:42:10.480 each other neither of them you know is willing to budge much but they they they they come to kind

00:42:16.700 of a hard piece and so far that piece is held and they've both gone on and done other things it had

00:42:23.740 the hulk turnout in all this is the the sex tape gone well the the sex tape is mostly gone and and look

00:42:30.780 he walked away with many millions of dollars so i think he's doing he's doing all right but again you

00:42:37.100 know i having won i'm not sure how much sort of reflection and character comes from winning

00:42:43.480 i think he's actually quite proud of what happened i think he thinks he improved the world by it again

00:42:49.320 that's his opinion and we we should you know sort of probe that and and grant it what well not

00:42:54.920 necessarily agreeing with it wholeheartedly but i think he you know he saw this as kind of the

00:43:00.680 a big part of the third act of his life yeah i mean the hulk had had a rough go going up into that

00:43:07.660 thing uh sons in jail why his wife divorced him for and left him for a younger man daughter you know

00:43:14.860 career really wasn't going that great um so this kind of yeah this was this was a dark this this the

00:43:22.220 tape itself was the sort of culmination of like the darkest period of his life and so perhaps the case

00:43:28.620 ultimately is sort of closure and what allows him to move on and and you know do whatever he's going

00:43:34.900 to do next so i think there was a catharsis in it for him for sure so i mean this yeah throughout the

00:43:40.460 book you not only talk about sort of strategy and how to get things done but you're also using it as

00:43:45.840 a chance to explore our current media age yeah and after this thing happened the the verdict came in

00:43:52.340 favor for hogan and people found out that teal was the one that funded it there was like you said in

00:43:57.680 beginning there's all this hand wringing like what does this mean for media does this mean like that

00:44:00.920 billionaires can just take out media companies they don't like what do you think are the implications

00:44:05.740 of this case going forward in the the media i actually think the the precedent legally is much

00:44:13.040 less than people are are worried about because the truth is most media would never run this story to

00:44:20.120 begin with and so teal nailed them on a very narrow sort of invasion of privacy claim and and i think

00:44:28.480 before teal's involvement was revealed that's what most legal experts thought as well it's just when

00:44:34.580 the what the context changes when you find out a billionaire brought it about but i think the general idea of

00:44:40.800 using these using a lawsuit as a weapon to destroy someone to go after an enemy i think there is

00:44:47.920 some larger precedent there i mean look alex jones just got sued multiple times for defamation

00:44:54.220 donald trump might get brought down by the stormy daniels case james o'keefe the sort of

00:44:59.940 conservative media provocateur is is fighting a number of legal battles i think people are realizing that

00:45:06.340 oh you know just criticizing someone you know in an op-ed isn't really doing it anymore and if you want

00:45:13.800 to stop them you have to pursue other perhaps more involved or permanent means of doing so

00:45:22.900 do you think other like blogs like ocker like this was a wake-up call for them to like actually kind of

00:45:28.800 have some ethics about what they decide to publish or not publish i i think so i mean uh for probably for

00:45:36.300 better and for worse right on the one hand the media is going to be more conservative about

00:45:41.340 you know tacking potentially litigious people on the other hand you know they gawker should have

00:45:49.280 thought twice before they ran this hulk hogan tape they really like there's some argument for instance

00:45:54.660 over whether denton even knew that the hulk hogan tape was in gawker's possession and that they were

00:46:01.820 thinking about running it until after it was posted which is insane you know the the publisher of a media

00:46:08.320 company should know before his website does something like that and and so hopefully it makes

00:46:15.860 them more it makes them better at crossing their t's and dotting their i's but hopefully doesn't make

00:46:23.700 them unafraid you know i'm glad the new york times ran its its expose on harvey weinstein or that the

00:46:30.780 media reported on bill cosby and it's embarrassing and shameful that they didn't do it earlier but if you're

00:46:36.700 going to do those stories you better make sure you know you you you better make sure you're bulletproof

00:46:44.060 and so that that's i think the balance that the media is going to have to figure out so you know

00:46:49.880 after writing this book it's curious what do you think were the big takeaways you got from just about

00:46:55.520 getting stuff done strategies these are these are ideas you've been thinking about a long time so

00:47:00.440 what do you what were the big takeaways for you personally well so one i think that idea of patience

00:47:04.760 right you don't rush in you know few i i say like a a fight breaks out a conspiracy bruise

00:47:12.000 and so part of t i think teal gives gives us a very interesting example here of just patiently waiting

00:47:17.800 and then uh you know you get you've talked about john boyd uh before and on articles and on the podcast

00:47:24.200 you know he had this line he said a fighter pilot always goes through the back door never the front

00:47:30.200 and what he means is that the the the fighter pilot looks for the the weakness looks for the opportunity

00:47:36.480 they don't go head on and and i think that's a strategic lesson here too right the reason teal was

00:47:43.500 able to win is that gawker was overconfident and undefended in this area where they were taking risks

00:47:51.520 that they shouldn't have been taking and then look i think um teal's willingness to to to sort of get

00:48:01.080 his hands dirty is a lesson too you know it's very satisfying to go march in a protest or to donate

00:48:09.580 money to a politician or a cause that you support or to sign a petition right but how effective are

00:48:17.720 these things actually and how often do you actually see if you've accomplished what you set out to

00:48:22.400 accomplish and so i think what teal did is he was like i'm gonna solve this he's like no one else is

00:48:28.220 gonna solve it i'm going to take matters in my own hands and i'm gonna work really hard for a long time

00:48:34.240 to solve this and i think there's some strategic lessons there too you know if you're i'm relatively

00:48:39.900 pro second amendment but if you if you think we need gun control in this country well don't just yell

00:48:45.900 about it but figure out what can actually be done and that's going to involve compromise that's going

00:48:50.860 to involve collaboration that's going to involve patience that's going to involve the long game

00:48:55.720 you know if you think donald trump is evil don't just tweet about it man you're gonna you're gonna

00:49:00.780 have to you're gonna have to work at removing him from office or or you know if you think there's a

00:49:07.240 problem with suppressing free speech on college campuses well maybe you've got to find like teal did the

00:49:13.620 perfect representative case that helps you set a precedent that you want to set that protects the

00:49:19.860 people that you want to protect you know and so on and so forth so i think there that's the real

00:49:24.640 strategic lesson which is that change is possible but it's not going to come just because you think

00:49:30.440 that it's right it has to be made real well ryan this has been a great conversation where can people

00:49:36.000 go to learn more about the book so the book is uh conspiracy it's on amazon everywhere books are sold

00:49:41.940 and uh you can go to my website at uh ryan holiday.net all right ryan holiday thank you so

00:49:47.340 much for time it's been a pleasure thank you my guest today was ryan holiday he is the author of

00:49:51.660 the book conspiracy it's available on amazon.com and bookstores everywhere also check out his website

00:49:56.820 ryan holiday.net while you're there sign up for his reading list email newsletters one of my favorite

00:50:01.840 newsletters i get he shares what he's been reading gotten a lot of recommendations from that also check

00:50:05.780 out our show notes at aom.is slash conspiracy where you can find links to resources where you delve deeper

00:50:11.040 into this topic well that wraps up another edition of the art of manliness podcast for more manly tips

00:50:27.460 and advice make sure check out the art of manliness website at artofmanliness.com and if you enjoy the

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00:50:42.160 you for your continue to support until next time this is bratt mckay telling you to stay manly

00:50:45.600 you

The Art of Manliness - July 31, 2025

#412： The Power of Conspiracy and Secrets

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