Bollea v. Gawker

If Ryan Holiday held a conference for his 1,000 true fans, I might claim a badge. I subscribe to his newsletter, read Meditations, and filter through his regular book recommendations. I’ve debated Ego is the Enemy. Thought long and hard about writing from the notes in Perennial Seller. I don’t have his face tattooed on my arm, or anything to the extreme, but I have purchased most of his work. Yet, for whatever reason, I put his book on the titanic First Amendment battle of Bollea (aka Hulk Hogan) v. Gawker aside, waiting in a way. Perhaps, the content hit too close to home. I once worked for a great company, idealistically, that helps manage some of the world’s largest media companies. CNN. The NY Times. Content Management Systems (CMS) have a long reach. Some technology can last forever. And as a salesperson, those who call this a profession, advocate for their clients.

After a brief hesitation, I recently took the plunge. Channeling Robert Greene, Ryan’s focus for this broader tale is narrow. Conspiracy. To begin, he cited,“What important truth do very few people agree with you on?” I’ll give you mine to close this short preface: Perhaps we have too few conspiracies, not too many. We could almost always use more boldness, and less complacency. We could use less telegraphing of our intentions or ambitions and see what secrecy, patience, and planning might accomplish. We could use a little more craziness and disruption, even from the people we disagree with.

Yes, “The beginnings of all things are small,” Cicero reminds us. And told through that lens, Ryan deftly describes the tale of Nick Denton’s multi-million dollar media empire, arguably hiding behind First Amendment principles, battling against the man behind the curtain, a billionaire. No one had challenged Gawker and won. In fact, almost no one had ever challenged the American media, period, and won. After the series of famous Washington Post stories by Bob Woodward and Carl Bernstein about the Watergate scandal in 1972, President Nixon not only fails to destroy the paper’s publisher, Katharine Graham, he destroys himself in the process and officially ends the traditional deference between the press corps and the presidency.

Like most of Ryan’s books, this is a fast read. A popcorn tale filled with complicated actors, bankruptcy, betrayal, conspiracy plots, and the WWF. But, I felt, he left too much on the table to hit a deadline or beat another writer to market. Ryan’s work dances up to journalism’s inner ethos and philosophy, but never asks the prom queen or king out on a date. In the future, I hope someone else digs deeper on a few challenging topics:

  • With the fate of social media being debated to the ends of the earth these days, he could have explored the role of technology disruption. How has Denton’s page view economics impacted the role of journalism? Why do media companies relentlessly attack Facebook today? What are the economic incentives for each party? Do they attack Facebook because of the platform’s inability to control fake news? Or, is it centered around advertising revenue pie?
  • Yes, technology can drive a company, but culture matters. How did Gawker’s no holds bar attitude limit growth? What made other organization’s make the turn, while others don’t? Denton built a CMS to challenge the likes of Drupal, WordPress, Adobe, etc., but why isn’t the technology more prevalent today?
  • The American legal system is driven by money. The average person can’t put up 25 million to win a court case.
  • And … perhaps most important … how did a Florida jury, after million’s of dollar’s invested, make the world realize that you shouldn’t be able to say whatever you want. Human decency. The art of being a good person. Honor. Friendship. Doing what’s right. Playing the long game matters.

The author brushed on these, but if only he would have delved deeper. I hope there is a second edition. Great read. Made me ponder.

Quotes and Highlights:

The Role of Decency in Business:

  • He didn’t understand how and why people would treat other people like that. There must have been a way that Gawker reminded Thiel of the self-righteous people he had been railing against since he was a conservative polemicist in college: the people who claim the moral high ground, who claim to be about freedom of choice, but who bully everyone who doesn’t choose their way of freedom. For a complicated man with specific opinions about complex ideas, one might suspect that the gravest threat Gawker posed—why it seemed to him to be a form of terrorism—was the tendency for its trenchant, snarky reporting to become reductive and to cause collateral damage.
  • But a rich man has feelings, just like a poor man, worries and fears and opinions like a regular man. The difference is that the former has a way of thinking that he ought to spend his money doing something about them. And rich men don’t tend to like feeling small, feeling that same powerlessness they had once felt at a young age that had driven them to accomplish the things they had accomplished.

Always Look Over Your Shoulder:

  • There is a story that Herodotus tells in The Histories about a war between Sparta and Tegea. In it, the Spartans were “so confident of reducing the men of Tegea to slavery” that they literally brought chains with them. But they lost, having dreadfully underestimated their enemy, and with poetic justice the prisoners were “forced to wear on their own legs the chains they had brought.”
  • They didn’t take any legal matter seriously because they never had to. But the past is no indicator of the future— ask the fattened Thanksgiving turkey or the proverbial man stacking straws on a camel’s back. It’s Rome telling itself that no one could ever cross the Alps. Then one day Hannibal appears in Italy with his elephant. Shit, they can do that?
  • There were signs, though, if anyone had wanted to look, that they might have made an enemy who would be difficult to appease. The mansion that Hogan filmed his reality show in had once been worth $25 million. It sold in 2012 for $6 million. The other houses, the friends, the family, the glory days—they were all gone. His wife had taken 70 percent of their marital assets in the divorce settlement and promptly settled in with a younger man. How long and how far had Terry Bollea crawled from the shipyards of Tampa to get to where he got? How many chairs did he take to the head? How many dingy arenas did he perform in to build this character? How much did he love being loved, by children and their parents alike, as the caricature of American excess and goodness in the Cold War? This is the man who got to play the hero for a living and now much of that is gone. And here some New York blog was humiliating him by parading his best friend’s betrayal across the world wide web and putting his naked, aging, balding body on display in a sex tape he had never asked to be in. He was a man with little to lose.
  • Hillary Clinton spent her whole life trying to become president. She began her final campaign nearly two years before the election, cutting off at the pass anyone within her party who might seriously challenge her. She raised more money than you could ever possibly need. Donald Trump was underprepared, erratic, constantly in his own way. But it cannot be said that he did not want to win very badly. He wanted to win even more than Hillary. The last few weeks of the election made that fact indisputable. She had already won in her mind, she felt she deserved it. Trump, on the other hand, was willing to do anything, go anywhere, bear any shame, tell any lie, ally with any group if it meant he could take it from her. And he did.
  • To not know yourself is dangerous, but to not know your enemy is reckless or worse.

The Best Advice, Being Liked:

  • Being feared, Machiavelli says, is an important protection against a conspiracy. The ultimate protection, he says, however, is to be well liked. Not simply because people who love you are less likely to want to take you down, but because they are less likely to tolerate anyone else trying to, either. If a prince guards himself against that hatred, Machiavelli writes, “simple particular offenses will make less trouble for him . . . because if they were even of spirit and had the power to do it, they are held back by the universal benevolence that they see the prince has.”

Incentive Models Impact Company Culture:

  • It was like a textbook example of a Marxist exploitation. He had the most equity in it and he had a lot to lose, whereas the slave wages they were paying their writers meant that the writers had nothing to lose.” Denton was as misaligned culturally as he was financially.
  • But the incentives were built into the core of the company. The writers had no stake in the business, only in the notoriety. They were measured in page views, and they knew the best way to get them was to say and do the things that no one else could—or would. And yet Denton also knew that he could not afford for them to be too much nicer anyway. He needed the traffic to show the growth to lure in new investors to pay the legal bills he was now drowning in. He needed to keep the audience entertained, too. They were fickle, they did not appreciate his predicament. They have their own problems, and don’t care about his.
  • Denton would explain in an interview with Playboy that this kind of radical honesty was partly a defense strategy: “The easy way to insulate yourself against snark is to preemptively snark. Snark before anybody else does. That’s a kind of classic defensive humor. Make fun of yourself before somebody else does and lower everybody’s expectations. . . . I lower everyone’s commercial expectations. ‘Oh, nothing to see here. There’s no business here. This thing has the revenue of a hamburger stand. We have no journalistic ambitions. If we ever commit journalism, it’s by accident.’”
  • One can’t shame the shameless. Gawker had embraced a role that meant it didn’t have any. It had preemptively made itself next to impossible to criticize. It was the bully that had convinced people it was the underdog, and was so confident in it, it even told everyone that’s what it was doing.

Other Good Stuff from the Book:

  • Just as rules are meant to be broken, it seems, secrets are meant to be shared.
  • It’s said that gangsters look good up until their last fifteen minutes, when it turns really ugly and sad.
  • Scipio Africanus, the general who defeated Hannibal, would say that an army should not only leave a road for their enemy to retreat by, they should pave it in gold.
  • We live in a world where only people like Peter Thiel can pull something so intentional and long-term off—and it’s not because, as Gawker has tried to make it seem, he’s rich. It’s because he’s one of the few who believes it can be done. To borrow a line from Zero to One, to believe in conspiracies is an effective truth.
  • Anyone who is threatened and is forced by necessity either to act or to suffer,” writes Machiavelli, “becomes a very dangerous man to the prince.”
  • There is something popular with ambitious people called the “briefcase technique.” You don’t show up to a 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.
  • Peter, if everyone thought that way, what would the world look like?” “Just hearing that was so refreshing,” Peter would say later, “because of course what you always heard were these incremental things that wouldn’t quite do it.”
  • A start-up is, in Peter’s definition, “a small group of people that you’ve convinced of a truth that nobody else believes in.”
  • Peter Thiel likes to ask: What do I know about this company that other investors don’t know? In other words: Do we have an edge? It’s only with some sort of informational asymmetry, goes the thinking, that one can not only beat the market but dominate it.


  • I needed a picture of Machivellia’s famous tome for this post. However, I felt the story had a small amount of the Illiad. Two lesser gods squaring off against one another, almost unknowing that one of Olympian’s finest waited to destroy the other.