My 24 Favorite Lessons From Ryan Holiday’s Book Conspiracy: Peter Thiel, Hulk Hogan and the Anatomy of Intrigue

Date Read: 04/23/2018

How strongly I recommend it: 9/10

See Book Here 

In 2007, a short blogpost on Valleywag, the Silicon Valley-vertical of Gawker Media, outed PayPal founder and billionaire investor Peter Thiel as gay. Thiel’s sexuality had been known to close friends and family, but he didn’t consider himself a public figure, and believed the information was private.
This post would be the casus belli for a meticulously plotted conspiracy that would end nearly a decade later with a $140 million dollar judgment against Gawker, its bankruptcy and with Nick Denton, Gawker’s CEO and founder, out of a job. Only later would the world learn that Gawker’s demise was not incidental–it had been masterminded by Thiel.
For years, Thiel had searched endlessly for a solution to what he’d come to call the “Gawker Problem.” When an unmarked envelope delivered an illegally recorded sex tape of Hogan with his best friend’s wife, Gawker had seen the chance for millions of pageviews and to say the things that others were afraid to say. Thiel saw their publication of the tape as the opportunity he was looking for. He would come to pit Hogan against Gawker in a multi-year proxy war through the Florida legal system, while Gawker remained confidently convinced they would prevail as they had over so many other lawsuit–until it was too late.
The verdict would stun the world and so would Peter’s ultimate unmasking as the man who had set it all in motion. Why had he done this? How had no one discovered it? What would this mean–for the First Amendment? For privacy? For culture?
In Holiday’s masterful telling of this nearly unbelievable conspiracy, informed by interviews with all the key players, this case transcends the narrative of how one billionaire took down a media empire or the current state of the free press. It’s a study in power, strategy, and one of the most wildly ambitious–and successful–secret plots in recent memory.
Some will cheer Gawker’s destruction and others will lament it, but after reading these pages–and seeing the access the author was given–no one will deny that there is something ruthless and brilliant about Peter Thiel’s shocking attempt to shake up the world.

Basically as I go through any book that I read, I underline interesting ideas/quotes/paragraphs and then later come back through the book to get the lessons gleaned from these underpinnings and try to figure out what they mean to me and apply them to my own life.

Here were the most interesting lessons in the book for me:

*Never Trust Appearances: Arnold Rothsein fixed the 1919 World Series, a then young Dwight Eisenhower was following the game, but didn’t suspect a thing. He found out years down the road that the game was fixed, and immediately realized how easily we all are fooled by others in life, how quickly we take surface appearances as incontrovertible fact.

*All Things Have Consequences: The whole Peter Thiel, Gawker conspiracy started with one little tiny blog post, outing Peter Thiel as gay, followed by a smug comment by Nick Denton founder of Gawker where he called Peter weird for trying to ‘hide it.’ All things have consequences that you can’t foresee in the beginning.

*Self-Control Is A Virtue: Ryan says “in a fight, one responds to a punch by throwing a punch. But in a conspiracy, one holds their punches and plots instead for their complete destruction without even bloodying their knuckles.” We all feel the emotions swell up when we want to get revenge on someone, and end up trying to go blow for blow with our opponent, who is at least some of the time stronger for us, the smart ones plot behind the scenes, not willing to go blow for blow, but to take them from behind.

*Eccentricity Is Valuable: Peter Thiel believes all progress comes from creating space for the ‘weirdos’ of the world to connect. For the politically incorrect to do odd things and to feel comfortable enough to put out there ideas. And when a site like Gawker punishes anyone who steps out of the ‘norm’ it inherently hinders progress.

*Be A High Agency Person: When you’re told something is impossible or can’t be done, is that the end of the conversation, or does it start another conversation in your head about how you’ll get around this obstacle. This comes from Peter Thiel’s friend Eric Weinstein, and it is the first thing I use when hiring people. I give them some odd, seemingly impossible task to get done for them to get the job, and if the react the first way saying “It can’t be done” I know that I can’t hire them.

*Try The Briefcase Technique: Ryan explains this popular technique that basically says you don’t show up to a pitch meeting with a few vague ideas, you have a full-fledged plan that you take out of your briefcase and hand to the person you are pitching. Even if nothing comes of it, the person is so blown-away by how prepared you came and will see you useful in some capacity.

*The Plenipotentiary Model: In both of Thiel’s companies, early on he hired strong CEO’s and Leaders to execute the day to day while he created the long-term vision he created. This gave him the distance to see the signal from the noise and not be distracted by every little whistle.

*The Definition Of A Start-Up: Thiel says it’s a “small group of people that you’ve convinced of a truth that nobody else believes in.” To me this means two things. It’s your job as a founder of any project to convince the team how great an idea it is, not just for them to ‘get it’ right away and secondly if you don’t have people who think the idea is downright crazy or stupid, it’s probably not going to be anything world-changing.

*Begin With The End: Thiel’s favorite chess player Jose Raul Capablanca would say “to begin, you must study the end. You don’t want to be the first you can, you want to be the last man standing.” Way too many of us are reactive and can only see the shiny thing or red notification alert right in front of our face, but the true strategist makes every decision with the next 10 steps in mind.

*Where Is Nobody Looking? B.H Liddell Hart, the great strategist would say all great victories come along “the line of least resistance and the line of least expectation.” If a bouncer at a club won’t let you in, don’t try to outmuscle him, you’ll lose, don’t even try to smooth talk him you’ll lose. Instead, scope the place out and find a way in through the basement. Ask yourself “where is nobody looking?”

*Boldness Over Timidity: Thiel says “under the right conditions, a little boldness will make much more progress than timidity will ever protect” and uses this as his guiding principle in his investing. This sort of ties into asking yourself “what is scarce?” If everyone is timid, which is usually true, than injecting boldness makes you rare. A willingness to try things others aren’t can lead to great results if tempered with as clear, rational thinking as possible.

*Finding The Right Tactics: Thiel and his team developed their strategy of how they would approach taking down Gawker, but next was deciding on the tactics, which in this case was deciding what cases they could fund against Gawker. Say your strategy is to “use influencers to grow your online business” well there are 1,000 different tactics you can use to implement that strategy, it’s your job to try a few and figure out which one is bringing the most return.

*Embody Contradiction: Ryan says that Thiel embodying contradiction, keeping two antagonistic ideas in his at the same time is what makes him a brilliant investor, he’s able to see things from many different perspectives. It reminds me of the 5-Hats Theory, which basically says to look at each decision with 5 hats: a white hat could be optimistic, green hat could be from a financial standpoint, red hat could be from a creative perspective, allowing you to see all these different paths.

*A Conspiracy Requires Stamina: Whether it’s a business, politics, or a legal conspiracy like Thiel’s there are so many setbacks, that if you don’t mentally prepare for them beforehand you can lose your head and give up. Ryan uses this great quote from Lucretius who described life as “one long struggle in the dark.” But if you’re willing to struggle long enough, you’ll find that one switch that illuminates a little bit of the room, and that leads you to the next switch, and so forth.

*A Leader Should Be Stoic: Napoleons mantra for leaders was “he must not allow himself to be elated by good news or depressed by bad, in the course of any campaign there will be plenty of both.” It’s back to reactivity, if you follow life’s every whims, which happens to resemble a roller coaster and let you emotions & thoughts follow life, you will end up having a heart attack. Study Marcus Aurelius, Seneca, and Ryan’s Daily Stoic. (Link to all)

*Know Your Enemy. Sun Tzu said you must know your enemy as well as yourself. To not know yourself is dangerous, but to not know your enemy is reckless. Before Gawker even published the sex tape of Hulk Hogan, he made it loud and clear that he would sue whoever did so, his lawyers sent cease and desist letters, and they still didn’t listen and take him seriously when the lawsuit proceeded on and on, instead they laughed and thought it frivolous.

*Cockiness Can Kill You: In The Histories in a war between Sparta and Tegea, the Spartans were so confident of themselves they literally brought chains with them to bring back the men they captured into slavery. But they lost, and were in turn forced to wear the chains they brought themselves. The Gawker team would do much the same by their smugness in their depositions and how carelessly they answered questions, so confident that this whole thing would end, leaving them unscathed, their words became their chains.

*Secrecy Is Key: Ryan says “when people who don’t like what you’re doing know that you’re trying to do it, they are more likely to be able to stop you. It’s that simple.” He also explains that we have a complicated relationship with secrecy, it’s seen as ‘wrong’ or ‘immoral’ but really that claim in and of itself is a power game as people feel the lack of control when secrets are withheld from them.

*Choose The Plan With The Most Options: B.H Lidell Hart would compare a good plan to a tree, saying “a healthy one has many branches, and that a plan with a single branch is but a barren pole.” Our theoretical plans never stand up to the real-world experiments acted out in life, but they are a guiding light to show us the next step, and when we have a plan with many options we’re able to think quickly on our feet and anticipate the next move before it’s even there. One of Thiel’s associates said “Hogan was one iron in the fire at the time. We were constantly looking.” They weren’t banking on Hogan being the winner, no matter how confident, they knew once a plan was set out in the wild it was out of their control.

*Aim For Being Well-Liked, Over Being Feared: “Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection however, is being well-liked.” Because one day your luck will be down and you will be ousted from your powerful kingdom, and in that moment when you’re vulnerable in the middle of the crowd, will people be hungry to attack, or eager to help? This decides your fate.

*It Always Takes Longer Than Expected: Gawker figured the whole case would Hogan would be over in a matter of months, but it had been years. Hogan’s lawyers wanted access to Gawker’s financials. Gawker wanted to about Hogan’s history of marital infidelity & on it went back and forth, tit-for-tat. Always plan for the long-game and have enough resources/energy/stamina to outlast your opponent and know if you think whatever you’re working on will take a few months, it’s probably a few years.

*Find Your Edge: Peter Thiel was not willing to just throw a Hail Mary and hop his funding Hulk Hogan’s case would prove fruitful. He spent $100,000 conducting two mock trials in Florida where the case would be held, something Gawker didn’t even consider. He wanted to know their weaknesses & strengths, asking himself “what do we have to do to beat them?” The edge is always there…

You Must Appeal To People’s Emotions: Peter said “you argue the law to show much you know about the law, but it’s not how you win a case in front of a jury.” The person who wins the jury is the one they like most, the more personable side, the one who tells the best story. It has everything to do with emotion, very little to do with facts or reason. So while Gawker insisted they had a right to publish Hogan’s sex tape, his lawyers appealed to the humanness in the jury by asking them how they would feel if millions of people watched them have sex.

*It Can Pay To Be A Contrarian: Peter definitely backs a lot of ‘out-there’ companies, and most will fail, but a few of them will have such big returns that it makes sense to take these risks. After Peter backed Trump in an unlikely win in the 2016 election he sent Ryan an email “contrarians may be mostly wrong, but they when get it right, they really get it right.”

I hope you can apply some of these lessons from Ryan’s incredible book in your own life…



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