Conspiracy | A True Story of Power, Sex, and a Billionaire’s Secret | Ryan Holiday | Book Summary



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Conspiracy: A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire

Book by Ryan Holiday

According to reports in 2016, you may have come across the news that former wrestler Hulk Hogan sued Gawker, which is well known as the gossip website. Hogan won his lawsuit against Gawker, and the site Gawker went bankrupt. You may be aware of all the information up to now, but what was beyond the visible? How do you think one of America’s most powerful and terrifying broadcast media could not see such a disaster that led itself to bankruptcy?

In this summary, you will understand how Peter Thiel, the billionaire technology shareholder, has astonished the entire media community by secretly plotting to bankrupt Gawker Media. We will find out what is the source of this grudge against Gawker by investor Thiel and how he finally managed to destroy this powerful site with secret plans. We will also see if Thiel supported the case that former wrestler Hogan filed against Gawker and how the Gawker media outlet found itself in a corner.

Chapter 1 – In 2007, Peter Thiel felt that the Gawker site was interfering with his private life.

As quoted by the Roman politician Cicero, “The beginnings of all things are small” So, what happened in the background of this incident was a conspiracy. This little spark was an entry posted on a website full of gossip in 2007, claiming that Peter Thiel, a tech investor, is gay. This entry, written with only 400 characters, was the beginning of a secret plan that cost millions of dollars and will last for years.

To find out why this entry was a major event that started all these events, we need to know more about the targeted investor Peter Thiel and the gossip-spreading Gawker site.

Let’s talk a little bit about investor Peter Thiel.

In 2007, Peter Thiel was already a major investor who added wealth to his fortune. Thiel, who achieved significant success by establishing PayPal, the online payment system, was famous as the first entrepreneur to invest in Facebook. With the knowledge of family, friends, and colleagues, Thiel’s sexual preferences in 2007 were a secret in Silicon Valley that was not openly spoken and kept. Indeed, Thiel was incredibly sensitive when it came to personal life.

Now let’s come to the website that posted this blog entry. The name of this website was Valleywag. Valleywag was originally founded as a tech news site but learned its editorial features from Gawker media, known as its affiliate gossip website.

The owner of the Gawker and Valleywag websites was British Nick Denton.

Denton had a good background in technology, but his main concern was private secrets and gossip. In particular, he loved to reveal information about people’s private lives on his websites, stating that he had a sense of amusement and clarity.

So whose secrets were worth revealing? The secrets of people especially wealthy, strong or celebrated, of course. Employing a team of young and ambitious writers with humorous but derogatory writing skills, Denton has invited these writers to reveal and make fun of famous people and organizations they think are self-righteous or have some secrets. And such articles have enlivened their followers. In 2005, the websites, owned by Denton, especially Gawker, earned an average of $ 120,000 per month from advertising revenue. By 2012, Gawker’s earnings were going towards $ 40 million.

However, Nick Denton did wrong to the wrong person he could do in the entire media community in 2007.

Chapter 2 – Gawker’s sniffing into Peter Thiel’s private life demonstrated his understanding of journalism, which should now be limited.

December 19th, 2007 is the date Peter Thiel began to hate the Gawker site. This was when they exposed him on the Valleywag website with the headline “Peter Thiel is gay, people” Was that the main reason Thiel reacted so much to this simple input and resentment towards the site?

To fully understand the reason for Thiel’s anger towards this media outlet, we must take a look at the sexual perception in 2007 and other events and people revealed by the Gawker site.

When we examine the past with our perception of this period we live in, you may find it unnecessary for a homosexual person to want to hide their sexual preferences from everyone. However, in 2007 our perceptions were in very different directions. Obama would approve gay marriage five years from this year, and it would take Hillary Clinton another six years to support same-sex marriage. In other words, it was a more difficult time to protect homosexual people and their rights.

When Valleywag published the post revealing Thiel, he perceived it as an attack on his private life. And the Gawker company’s disrespect for Thiel’s privacy continued. Later that year, Valleywag shared more content by posting the name and picture of Thiel’s boyfriend. Blog posts on the Gawker site revealing Thiel’s private life were viewed a total of 500,000 times between 2007 and 2008. Thiel, who lived a quiet life until then, and his sexual orientation were on everyone’s screen online.

Although Gawker’s posts about Thiel were rather immoral, these things were completely unimportant to it. The Gawker company was quite famous for its ambition to publish stolen information and reveal secrets of unknown origin. In 2005, it disclosed a secretly seized sex video of Fred Durst, lead singer of Limp Bizkit. Gawker site writers congratulated themselves for being more courageous than traditional media outlets to say and publish certain things openly. So what happened when some of those who suffered so much from Gawker articles tried to claim their rights? Gawker was only amused by those seeking their rights, as he was well aware of the strict freedom of expression that prevails in America.

Realizing these methods of Gawker, Thiel named Gawker as MBTO, which is the abbreviation of “Manhattan Based Terrorist Organization”. And he saw the urgent need to eliminate those gossipers, being pretty sure that they are scary and harsh.



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Chapter 3 – Dealing with Gawker was a challenge, but Thiel had many methods to use for this purpose.

During 2008 and 2011, Peter Thiel was pondering how the Gawker Company could be harnessed and how to stop it from disclosing people. What was the way to damage the site? No one has ever been successful in dealing with the American media. An old saying advises: Never mess with anyone who buys their ink in barrels. So, journalists cannot be bullied.

Sure, Peter Thiel had a fortune and was pretty smart, but those around him thought the Gawker Company would never be defeated.

So what was the reason why Gawker was so protected?

America’s First Amendment, which covers freedom of expression laws, gave journalists a solid assurance to prosecute anything they expressed.

Gawker Media, on the other hand, would never regret what it did. Had Thiel got into a conflict with Gawker founder Nick Denton and accused this company of bullying, Denton and his ruthless writers would have published even more provocative articles about Thiel. They would reap gains for their reputation from a revenge fight with a wealthy investor.

As a last resort, Peter Thiel couldn’t just buy the Gawker Company and change his journalistic orientation. It was a free media outlet that was not affiliated with anyone but Denton, and Denton was not inclined to sell this media kingdom that he owned.

However, Peter Thiel was also used to dealing with difficulties.

By 2011 he finally found a way to eliminate the gossiper. Thiel planned to start a new company with a single goal, with a young business partner known only as Mr. A, whose name he did not reveal to the author. This secret company managed by Mr. A secretly started employing investigative journalists and advocates. Their only job was to review all articles posted on Gawker’s sites to determine whether the company was doing anything illegal.

Mr. A and his employees sought to check whether there was some illegal work that was not subject to the freedom of expression law. So what was the reason for this? Because the American justice system was very serious about the lawsuits against freedom of expression.

However, Gawker’s crimes were important to Peter Thiel. If the article review team could find any illegal practice that would constitute a crime in court, he and Mr. A. Gawker would try to destroy it.

Chapter 4 – Thiel’s long-awaited moment was when former wrestler Hulk Hogan sued Gawker for breach of privacy.

Mr. A and his team of detectives reviewed and passed on every piece of information disclosed on Gawker sites to Thiel. Thiel was thus sure that Gawker had to be destroyed immediately. There should be no end to what this immoral website is doing. Even secretly shot nude photos of famous women were featured on the site. But how could Thiel and his lawyers be involved in this court trial?

Luckily, the opportunity they were waiting for came in 2012.

In 2012, former wrestler and actor Terry Bollea, known as Hulk Hogan, fell prey to Gawker. A few years ago, Hogan was secretly filmed having sex with his best friend’s wife. This sex tape shot without Hogan’s knowledge and permission was transmitted to the Gawker website in 2012, and the site did not see any harm in publishing it. Hogan, who was shocked and embarrassed, sent a warning to Gawker with his lawyers that he would sue the site if the sex tape recorded without his knowledge and permission was not removed from the site.

The very confident site, as always, did not take this warning seriously. Hence, Hogan’s lawyers sued Gawker.

Thiel’s long-awaited opportunity came to him when former wrestler Hulk Hogan sued Gawker for breach of privacy. Hogan’s lawsuit against Gawker was outside the scope of freedom of expression found in American law. Hogan’s case was an example of Gawker Media’s crime of violating one’s privacy. Although it has a very close separation, the protection of privacy and the right to freedom of expression were two different legal rights. Hogan could have won his lawsuit against Gawker, as it was easier to be guilty of breaching privacy than freedom of expression.

Waiting in line to demolish Gawker, Mr. A met with Hulk Hogan and asked if he would like to sue Gawker with help from an unknown person. Thiel did not want anyone to know about his desire to destroy Gawker. If the Gawker company sensed his purpose, it could quickly spread immoral rumors and embark on the fight. There was no limit to the lies they would invent about Thiel and the slanders that would destroy his reputation.

Fortunately, Hogan wasn’t too interested in who this benevolent person was. His only interest was the deletion of the sex video recorded with his friend’s wife from Gawker’s website.

Peter Thiel was close to the day of reckoning with Gawker in court.



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Chapter 5 – Gawker had not assumed Hogan was dangerous until he saw the facts.

In 2016, Peter Thiel’s plan to destroy Gawker finally worked. A judge ruled that Hulk Hogan could get a massive $ 100 million in damages from Gawker for breach of privacy against him; Bollea and Gawker appeared before the jury.

After this decision, Gawker Media and founder Nick Denton surprisingly didn’t care about it instead of worrying.

This was no big deal for the Gawker company and Denton until the lawsuit that Hogan accused the site of breaching privacy began. One of the reasons for their recklessness was that they did not know that Hogan was paying his lawsuit fee with the help of a wealthy investor. Unfortunately, Gawker Media thought Hogan was paying the court fees out of his pocket. Gawker Media, who was heavily insured for the price of its legal fees, thought that Hogan, who was not in a very good financial condition, could not pay all court fees.

Hence, Denton and company lawyers thought Hogan would withdraw from the case with compensation for much less than $ 100 million.

But this time Gawker was trapped. Gawker finally called for an agreement before the case went to court, offering Hogan $ 10 million and did not apologize to him. Knowing he had a strong source behind him, Hogan refused to accept the deal.

It is highly probable that Gawker Media would pay dearly for its previous reckless behaviors.

When Bollea and Gawker went to court, Gawker realized that it was trapped. Also, this case was not being held in the courts of the great New York City, but Florida, located on Hogan’s borders. People in the Florida jury included people who had a lot of respect and love for local celebrities like Hulk Hogan. The Gawker Company’s lawyers argued that all obscene articles and published sex tapes were a manifestation of freedom of expression, but what they said was not justified by anyone. The jury considered a successful local celebrity to be discredited by a cynical and cruel organization being unaware of other worlds.

What was the verdict? In March 2016, the jury ruled in Hogan’s favor, awarding him $140 million in compensation. Thanks to Peter Thiel’s set of conspiracy plans and determination, Gawker is now gone.

Chapter 6 – Gawker went bankrupt because of the damages paid to Hogan, and there was a strong media reaction against Peter Thiel.

What would your reaction be if a court asked you or your company to pay $ 140

million in compensation? If you’re a free outlet like Gawker Media, doing it like Nick Denton would probably be the only solution: Announcing your bankruptcy and ending the company.

Surprisingly, Peter Thiel was not happy with this decision but worried that he was also at great risk.

After the trial, news quickly spread that Peter Thiel was the person who supported Hulk Hogan. During the court process, no one knew that he was involved in the Gawker case, but it was impossible to celebrate his joy at the win of the case. Despite sharing this information with some of his friends, the rumors quickly spread throughout the country.

Thiel, who has been conspiring to the finest detail for years and plotting for every situation, was very surprised by the negative reactions from the American people. At first, many journalists found the jury’s compensation decision for Gawker to be justified, but they gave up on learning Thiel’s support. Suddenly, the media that branded Peter Thiel as a vengeful rich began to present his hatred of a brave media outlet as his hatred of freedom of expression.

Thiel suffered from this reaction and could not understand it. He thought his support served a good cause. This success was a victory over the tyrannical media that pressured ordinary Americans everywhere, especially those who could not afford to defend their rights against the media.

Do you think Peter Thiel is right about this? The author thinks that you should make your own choice on this topic. However, you should take into consideration the following before making a decision.

Thiel had kept his plans in secret, but they were not illegal. Because of his wealth, he always preferred to use his opportunities to the extent permitted by law.

Finally, there is one more thing you should think of, according to the author. Thiel refused to accept and submit to the current situation alongside his plans and personal ambition, which he devoted much time to preparing for Gawker’s disappearance. Probably, these personal traits are equated with his fortune in winning this case. Against the top political authorities trying to impose the current situation on us, all people can learn from Thiel’s long-term plotting and dedication. In other words, perhaps even more conspiracy plans are needed to fix the disturbing world order.

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday Book Review


Peter Thiel’s conspiracy plans to beat Gawker lasted nine years, and eventually, the wealthy investor spent about $ 10 million in the process. In the process that started with a short entry revealing Thiel, one of the most followed and hesitated media outlets in the world became history with the lawsuit including a well-known ex-wrestler. Whether you agree or disagree with Thiel’s behavior, it is a fact that this incident was the most daring conspiracy of the recent past.




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