#Notes Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue

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Conspiracy reads like a modern day version of The Prince, told through a long-form story. It's an interesting way to analyze what goes into a conspiracy by looking at the personal vendetta between Peter Thiel and Gawker Media (and their CEO Nick Denton). It breaks the conspiracy down into three stages and provides a blueprint of sorts for how to execute, act, and plan within each.

If you're not into reading hardcore books on strategy and deception from the olden days (like those of Sun Tzu, Churchill, and others) but want to learn about this stuff I would strongly recommend reading this book. It's a really fun and modern day lens to look at this stuff.

Top Lessons Learned

  1. Secrecy is of the utmost importance, including once the conspiracy has reached its natural conclusion, it's possibly even more important at this stage.
  2. Teamwork is an essential component of the conspiracy but it's important to find something powerful to bind each person together so that nobody turns or drops off part way through.
  3. Conspiracies are a powerful tool of the people who lack police or military power, it's like a guerilla expression of soft power.
  4. Conspiracies (like anything) can be used for good just as they can be damaging and evil.

General Notes

Conspiracy entails determined, coordinated action, done in secret—always in secret—that aims to disrupt the status quo or accomplish some aim.

“What important truth do very few people agree with you on?” -Peter Thiel

There is an option available to many but pursued by few: intrigue. To strategize, coordinate, and sustain a concerted effort to remove someone from power, to secretly move against an enemy, to do what Machiavelli would say was one of the hardest things to do in the world: to overthrow an existing order and do something new. To engage in a conspiracy to change the world.

Machiavelli said that a proper conspiracy moves through three distinct phases: the planning, the doing, and the aftermath. Each of these phases requires different skills—from organization to strategic thinking to recruiting, funding, aiming, secrecy, managing public relations, leadership, foresight, and ultimately, knowing when to stop. Most important, a conspiracy requires patience and fortitude, so much patience, as much as it relies on boldness or courage.


Starting point

All conspiracies start small, some kind of spark that drives somebody to start designing a plan; typically a transgression. The offended may not even know exactly what they want to achieve at this point, but the motivation exists.

Fights break out. Conspiracies brew.

These are the essential beginnings of a conspiracy:

  • First, a slight of some kind, which grows into a larger dissatisfaction with the status quo. A sense that things should be different, and will be different, except for the worse, if something doesn’t change.
  • But then comes a second step, a weighing of the stakes. What if I do something about this? What might happen? What might happen if I do nothing? Which is riskier: to act or to ignore?

Book recommendation: The Fifteen Decisive Battles of the World by Sir Edward Shepherd Creasy

Twenty-five hundred years ago, Thucydides would say that the three strongest motives for men were “fear, honor, and self-interest.”

Machiavelli said that conspiracies were weapons of the people. Only princes could afford to send an army against another army, he observed, but a conspiracy is available to every man. Which is why it is usually the desperate who turn to conspiracy and why the powerful fear them so much.

“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.”

A person son must decide, when they are told that something is impossible or cannot be changed, how they will respond. That usually means that nothing in the normal track of solutions can change things.

Team building

By definition, the first move in the act of a conspiracy is the assemblage of allies and operators: your coconspirators. Someone to do your bidding, to work with you, someone you can trust, who agrees with you that there’s a problem, or is willing to be paid to agree with the sentiment that it’s about time someone, somebody did something about this.

Cut outs can be a useful tool to protect the secrecy of the plot, protect information flow, and delegate the actual work to be done.

Should re-read the CIA’s guide to sabotage and on counter insurgency.

Compartmentalization is essential so a clear leader can remain at the front, guiding the strategic direction.

Hunger is an essential qualification. While it’s dangerous to conspire with people who have a lot to lose, you can’t conspire without someone who is afraid to bet on themselves, who isn’t willing to take a big stake on something that very well could fail. Where these two traits overlap there is often a sweet spot: the man or woman who has something to prove and something to protect, the strong sense of self-belief coupled with that killer instinct.

Finding out “how” and planning
To begin you must study the end. You don’t want to be the first to act, you want to be the last man standing.

  • It is imperative that you find your opponents strategic weakness, the more systemic it is, the better.
  • They should not be able to easily adapt to an attack on this weakness.
  • Side note: this is often why using a strength against an opponent is such a powerful move, because it is not in their best interest to remove that strength.

At a certain point in every conspiracy each participant realizes that proceeding will require of them something that little else in their life ever has. What that is isn’t willpower or resources or creativity, but instead a certain hardness and viciousness—the hard, unforgiving utilization of power or even violence against other human beings.

Machiavelli’s warning once again rings prophetic: “Anyone who is threatened and is forced by necessity either to act or to suffer becomes a very dangerous man to the prince.”


There will always be ups and downs, it’s important to stay focused on the end goal, don’t get thrown off by either.

Remember that even setbacks contain opportunities if you’re willing to step back and look for them through an unemotional lens.

When engaging in warfare, one very effective form of deception is getting the adversary to think about something else. This not only wastes their time but spends their resources and attention very effectively away from what is important to you.

If you know where your enemy is going and can control it, go there first and block/disrupt them further.

Culture eats strategy every time, both the bad and the good.

After the conspiracy

The aftermath is one of the most dangerous times as everyone's guard is down and public perception can shift so quickly.

  • It's important then to have contingency plans.
  • Answer the question "and then what?"

"To succeed you must study the end game before everything else."