Book cover of Conspiracy by Ryan Holiday

Conspiracy

by Ryan Holiday

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Introduction

In 2016, the media world was rocked by a shocking revelation: Hulk Hogan, the famous wrestler, had successfully sued gossip website Gawker for $140 million, forcing the company into bankruptcy. But there was more to the story than met the eye. Behind the scenes, a billionaire tech investor named Peter Thiel had been quietly orchestrating Gawker's downfall for years. Ryan Holiday's book "Conspiracy" takes us deep into this fascinating tale of revenge, privacy, and the power of determined individuals to change the course of events.

The Genesis of a Conspiracy

A Small Beginning with Big Consequences

As the Roman politician Cicero once said, "The beginnings of all things are small." This couldn't be truer for the conspiracy that would eventually bring down Gawker Media. It all started with a seemingly insignificant 400-word blog post published in 2007 on Valleywag, a tech gossip site owned by Gawker Media. This post outed Peter Thiel, a successful tech investor and entrepreneur, as gay.

Peter Thiel: A Private Man in a Public World

To understand why this blog post was so significant, we need to know more about Peter Thiel. By 2007, Thiel was already a major player in the tech world. He had made his fortune as a co-founder of PayPal and gained further recognition as Facebook's first major investor. Despite being open about his sexuality with friends, family, and colleagues, Thiel preferred to keep his personal life private. He was known for being intensely guarded about all aspects of his life outside of work.

Gawker Media: The Gossip Empire

On the other side of this story is Gawker Media, founded by Nick Denton. While Denton had a background in tech, his true passion lay in exposing secrets and spreading gossip. Gawker's mission was to reveal the hidden truths about the rich, powerful, and famous, often in a witty yet contemptuous tone. By 2005, Gawker and its sister sites were bringing in $120,000 in monthly ad revenue, and by 2012, that figure had skyrocketed to nearly $40 million annually.

The Fateful Post

When Valleywag published the post outing Thiel, it was just another day at the office for Gawker Media. They had no idea that they had just set in motion a chain of events that would lead to their own destruction.

Gawker's Controversial Journalism

Pushing Boundaries and Crossing Lines

Gawker's outing of Peter Thiel wasn't an isolated incident. It was part of a larger pattern of boundary-pushing journalism that had become the company's trademark. In the mid-2000s, the world was a different place, especially regarding LGBTQ+ rights. Same-sex marriage wasn't yet widely accepted, and many public figures still felt the need to keep their sexuality private.

A History of Controversial Stories

Gawker had built its reputation on publishing stolen material and anonymous leaks. In 2005, they had released a stolen sex tape of Fred Durst, the Limp Bizkit frontman. Gawker's writers took pride in saying and publishing things that more traditional media outlets wouldn't touch. If their targets tried to fight back, Gawker would only mock them more, confident in the protection of America's strong free speech laws.

The MBTO: Manhattan-Based Terrorist Organization

As Thiel learned more about Gawker's tactics, he began referring to them as the "Manhattan-Based Terrorist Organization" or MBTO. He became convinced that something needed to be done to stop this seemingly unstoppable media juggernaut.

Thiel's Quest for Revenge

The Challenges of Fighting Gawker

Between 2008 and 2011, Peter Thiel contemplated how to take on Gawker Media. It seemed like an impossible task. There's an old saying in journalism: "Never pick a fight with someone who buys ink by the barrel." This means it's unwise to battle against those who control the media. Even though Thiel was a billionaire and highly intelligent, many of his friends believed Gawker was untouchable.

Gawker's Armor

Several factors made Gawker seem invincible:

  1. The First Amendment: America's free speech laws provided strong legal protection for journalists.
  2. Shamelessness: Gawker couldn't be shamed into changing its behavior. Any public criticism would only fuel more inflammatory articles.
  3. Independence: Gawker was privately owned by Nick Denton, who had no interest in selling.

Hatching a Plan

In 2011, Thiel finally devised a strategy to destroy his nemesis. Working with a young business associate (known only as Mr. A), Thiel set up a shell company with a single purpose: to find a way to bring down Gawker. This company hired investigative journalists and lawyers to comb through thousands of Gawker articles, searching for evidence of illegal activity.

Importantly, they focused on finding wrongdoing unrelated to free speech laws, as those cases were notoriously difficult to win in the American justice system. If they could find something that would hold up in court, Thiel and Mr. A planned to sue Gawker into oblivion.

The Hulk Hogan Opportunity

A Golden Chance

As Thiel's team investigated Gawker's past publications, they became more convinced than ever that the website needed to be stopped. Gawker had published leaked nude photos of celebrities and seemed to have no ethical boundaries. But what could they use to win a court case?

In 2012, the perfect opportunity presented itself.

Hulk Hogan's Sex Tape

Terry Bollea, better known as professional wrestler Hulk Hogan, found himself in Gawker's crosshairs. Years earlier, Hogan had been secretly filmed having sex with his best friend's wife. This footage was anonymously sent to Gawker in 2012, and the company quickly published it on their website.

Shocked and humiliated, Hogan sent Gawker a cease-and-desist letter through his lawyers, threatening to sue if the sex tape wasn't removed. He explained that the video had been filmed without his knowledge or consent. Unsurprisingly, Gawker refused to take down the video.

A Perfect Test Case

This was exactly the kind of case Thiel and his team had been waiting for. Hogan's claim against Gawker wasn't about free speech; it was about privacy rights. This subtle difference was crucial, as privacy laws were easier to challenge in court than free speech protections.

Secret Support

Mr. A reached out to Hulk Hogan, offering financial backing from an anonymous third party to sue Gawker. Thiel wanted to keep his involvement secret to avoid Gawker's potential retaliation. Hogan didn't care about knowing his benefactor's identity; he just wanted the sex tape removed from Gawker's website.

With this alliance formed, Peter Thiel was one step closer to his day in court with Gawker.

Gawker's Fatal Mistake

Underestimating the Threat

As the lawsuit approached in 2016, you might think Gawker Media and its CEO Nick Denton would be worried. Surprisingly, they weren't too concerned. There were several reasons for their overconfidence:

  1. They didn't know Hogan had a billionaire backer. Gawker assumed Hogan was paying his own legal fees.
  2. Gawker was heavily insured for legal costs and believed Hogan, as a "single-digit millionaire," couldn't afford a lengthy court battle.
  3. They expected Hogan to settle out of court for a much lower sum than the $100 million he was asking for.

A Costly Miscalculation

Gawker's assumptions proved to be a massive mistake. When they finally offered to settle just before the trial, they proposed $10 million with no apology. With Thiel's unlimited resources behind him, Hogan easily rejected this offer.

The Trial Begins

Once the case of Bollea v. Gawker went before a jury, Gawker quickly found itself in trouble. They had failed to consider several important factors:

  1. The trial was taking place in Florida, Hogan's home turf, far from Gawker's New York City base.
  2. The jury was made up of local citizens who admired Hulk Hogan as a hometown hero.
  3. Gawker's arguments about free speech fell flat with jurors who saw only a beloved local figure being humiliated by snarky, out-of-touch New Yorkers.

The Verdict

In March 2016, the jury found in favor of Hulk Hogan, awarding him a staggering $140 million in damages. Thanks to Peter Thiel's long-term planning and perseverance, Gawker's fate was sealed.

The Aftermath

Gawker's Downfall

Faced with a $140 million judgment, Gawker Media had no choice but to declare bankruptcy and shut down its operations. Nick Denton's media empire, which had seemed untouchable for so long, crumbled in the face of this massive legal defeat.

Thiel's Revelation and Backlash

Shortly after the verdict, Peter Thiel's role as Hulk Hogan's secret backer was revealed. Although he had kept his involvement hidden during the trial, Thiel couldn't resist sharing his victory with a few friends once the case was won. Soon, the story was international news.

Thiel was unprepared for the media backlash that followed. While many journalists had initially supported the verdict against Gawker, opinion quickly shifted when Thiel's involvement became known. The narrative changed to portray Thiel as a vindictive billionaire threatening free speech by using his wealth to destroy a media outlet.

Thiel's Perspective

Thiel was hurt and confused by this reaction. He believed his actions had been philanthropic, striking a blow against a bullying media organization on behalf of ordinary people who couldn't afford to defend themselves. In his mind, he had done something noble and necessary.

Ethical Considerations

The author of "Conspiracy" encourages readers to form their own opinions about the ethics of Thiel's actions. However, he suggests considering the following points:

  1. Legality: Although Thiel's methods were secretive, everything he did was within the bounds of the law. Given his vast resources, the fact that he chose to operate legally should be noted.

  2. Personal qualities: Thiel demonstrated remarkable long-term focus, drive, and a refusal to accept the status quo. These traits were as crucial to his victory as his wealth.

  3. The power of conspiracy: In troubled times, when the status quo seems disturbing, perhaps we need more people willing to carefully plan and execute long-term strategies for change.

Lessons from the Gawker Conspiracy

The Power of Patience

Peter Thiel's conspiracy against Gawker took nine years to come to fruition. This demonstrates the importance of long-term thinking and persistence when tackling seemingly insurmountable problems. Thiel didn't let initial setbacks or the apparent impossibility of his task deter him from his goal.

The Danger of Hubris

Gawker's downfall can be largely attributed to its own overconfidence. The company believed it was untouchable and failed to take the threat of litigation seriously until it was too late. This serves as a cautionary tale for any organization that becomes too comfortable in its position of power.

The Complexity of Ethics in the Digital Age

The Gawker case raises important questions about privacy, free speech, and the role of wealth in shaping media landscapes. It highlights the tension between the public's right to know and an individual's right to privacy, especially in an era where information can spread globally in seconds.

The Importance of Strategy

Thiel's success came not just from his wealth, but from his careful planning and strategic thinking. He identified Gawker's vulnerabilities and patiently waited for the right opportunity to strike. This underscores the value of thorough preparation and strategic patience in achieving difficult goals.

The Power of Individuals to Effect Change

Despite Gawker's seeming invincibility, a small group of determined individuals managed to bring it down. This demonstrates that even in the face of powerful institutions, motivated people can make a significant impact if they're willing to commit to a long-term strategy.

Final Thoughts

The story of Peter Thiel's conspiracy against Gawker Media is a fascinating tale of revenge, strategy, and the power of determination. It cost Thiel around $10 million and took nearly a decade to execute, but in the end, he achieved his goal of destroying the media outlet that had invaded his privacy.

Whether one views Thiel's actions as justified retribution or a dangerous attack on press freedom, there's no denying the audacity and effectiveness of his plan. The Gawker case serves as a reminder of the complex interplay between wealth, power, privacy, and freedom of the press in our modern digital age.

As we navigate these issues in the future, the lessons from this conspiracy will undoubtedly continue to resonate. It raises important questions about the limits of free speech, the responsibility of media organizations, and the power of individuals to challenge the status quo.

In the end, the story of Gawker's downfall is more than just a tale of personal revenge. It's a case study in long-term strategic thinking, the dangers of underestimating one's opponents, and the potential for determined individuals to reshape the media landscape. As we move forward in an increasingly complex digital world, the implications of this conspiracy will continue to be debated and analyzed for years to come.

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