From Theory to Conspiracy: Takeaways from Ryan Holiday's "Conspiracy"

I just finished reading Ryan Holiday's latest book, Conspiracy. The book is a tale of a real conspiracy (not just a theory) led by Peter Thiel in which he backs Terry Bollea (you may know him as Hulk Hogan) in a lawsuit against the media giant, Gawker, led by Nick Denton. 

The story is riveting, though I won't try to summarize or sell you on the book at all with this post. Ryan Holiday does an excellent job of telling the story and revealing many of the details and thoughts from the characters themselves that you won't hear anywhere else. 

In this post, I'm going to go chapter-by-chapter and only write down the lessons I learned, rather than try to summarize the book for you. Here are those takeaways:

Disclaimer: these are not suggestions from me to you. They are lessons that I picked up from this book, and if I just so happened to be leading a conspiracy, I would surely find these valuable. That being said, I find them valuable nonetheless, and you'll probably find them interesting as well.

1: Humble beginnings

The much larger conspiracy starts with a much smaller and seemingly insignificant event. These humble beginnings are rarely obvious and might only become clear in hindsight. Nonetheless, there is a beginning to every conspiracy.

In some cases, someone has been wronged in one way or another. Sometimes it is a small infraction, an encroachment of another's power and authority, that begins a slow and steady brew of resentment in one party against the other. 

No matter what it is, conspiracies always have some sort of casus belli—some act or situation that justifies the waging of a much larger war.

2: Decisions and drive

The inciting incident has already come, gone, and in many cases been forgotten. However, the real conspiracy begins when the first vision truly pops into the conspirator's mind. It begins when the conspiracy is confirmed—a decision is made that something must be done.

Willpower plays a role throughout the entirety of a conspiracy. There is a risk inherent in conspiracy that will not go away, but deciding to act makes that risk real... and risky.

The three factors that make a man take the risk are fear, honor, and self interest. When all of those three are present, a decision is made.

3: Conspiracy as a weapon

It takes plenty of effort to ignore a problem and inaction may be just as costly as action itself. Sometimes, action is futile and conspiracy fails—but it is action nonetheless. You can conspire against just about anyone, and it is a weapon available to everyone. It is also a threat to everyone, for anyone may conspire against you.

When a person is forced to act, whether that be the powerful or the pitiful, they can become dangerous. They will exhaust all of their options and turn quickly to conspiracy. 

4: Teamwork

Criminals are simple-minded; their crimes are isolated and serve no larger purpose. They involve nobody else and say little worth hearing with their actions. On the other hand, a conspiracy must involve others. It takes more than one person and has a desired future state involved. It is an effort, part of a larger struggle between good and evil.

In assembling a team for a conspiracy, the roles must be clearly separate and compartmentalized. There is one mind behind the entire thing, and the moving parts are kept to themselves to ask few questions and simply execute. They know what they need to know, and not much else. Nor do they need to. Their needs are met, and to the extent that they understand their role, they are invested. Their self-interest is satisfied with the arrangement. Onward goes the conspiracy.

5: Alternate paths

Patience is key in discovering the most viable path to a successful conspiracy. You may have decided to act already, but you might not know exactly how, and that is perfectly okay. Patience and time, however, will reveal the opportunity.

After endless searching, a solution may become apparent to you, and that solution should also not be apparent to those on the other end of your conspiracy. This is the back door—the entrance that has been left unguarded through which you can invade and destroy the enemy.

6: Ruthlessness

Conspiracy is not without consequence for both ends of the ordeal. People will be hurt and some destroyed in the process. Some of this will happen on purpose and some of this will happen unintentionally. There is no avoiding this. A conspiracy is no benevolent plot. It is inherently destructive, and in order to proceed with such action, you must be able to tear out your heart and continue without it. Ruthless.

7: Defining moments

There is usually one moment (or multiple) in which a conspiracy is truly solidified. This moment often comes in the form of some challenge, change, or instability through which the conspirators power through. The opportunity shows up in an instant and action is taken that gets the ball rolling. At one point, you must seize the sword and attack. This is a defining moment.

8: Prepare for setbacks

More defining moments come in the form of setbacks. Every conspiracy will face these unavoidable events. The conspiracy, at this point, hinges entirely on whether or not the conspirators are able to take advantage of the opportunities that come after the setbacks. An effective conspirator has prepared for setbacks of all shape and size and is ready to deal with them. They may still be overwhelming, but at the very least they should not be unexpected. Expect the worst.

9: Know your enemy

An enormous advantage to have in any battle is to keep your true strength hidden. This may come in the form of posturing when your true strength is marginal at best, but this may also be reversed. It is also an advantage to be thought of as weak when in fact you are of much greater strength. Your enemy will not be able to accurately prepare for you and will plan according to their misinformation. Keep it that way.

When you are viewed as weaker than you actually are, your enemy will act with great confidence in the knowledge they seem to possess that you will inevitably be defeated. This confidence will make them weaker and open them up to attacks that otherwise would not be possible.

10: Being secretive is key

Being secretive can hide your true strength and disable your enemy from knowing who you are as their enemy. In general, it must also exist among the conspirators to keep all the parties in tact and operating according to plan. In World War II, it was kept a secret that the Allies had broken the Enigma and were able to decode all of the messages of the Axis powers. However, if this was not kept a secret, the enemy would have quickly adjusted and the advantage would have disappeared.

If transparency is allowed to exist in too much abundance, the true motives behind the conspiracy will be made clear and the narrative on which the entire ordeal hinges will quickly fall apart. Allow your enemy to deceive itself by thinking that they know everything.

11: Dazed and confused

Secrets are passive and simply exist in the midst of a conspiracy, but deception is active. It is deliberate. By way of many attacks on many fronts, all of which seemingly unconnected and uncontrolled, you will send your enemy into a spin of constant defense and force them to fight a war on many fronts. One small skirmish will not win the war, but many small skirmishes will weaken the beast. 

Confusum est, quidquid usue in pulverem sectum est.

Essentially, when the large plot is split into many small pieces, it is no longer recognizable as one big plan. A big picture makes sense, while the shredded version of the same picture dazes and confuses.

12: Culture and strategy

Success in both business and in a conspiracy can often be boiled down to the culture surrounding the efforts of the group. Are everyone's interests well enough aligned to achieve the desired result? Does everyone hold the same beliefs about what they want out of all of this? When culture is cohesive, it is usually a good thing.

However, cohesive but negative culture can be just as bad. A large group may all be bound together by their collective selfishness and ruthlessness. In this case, they are all similar—all bred under one culture—in that they will all quickly abandon each other when the appropriate time comes. All the strategy in the world won't fix that lack of good culture.

13: Have faith

The odds may not consistently grow in your favor. They will fluctuate wildly and this is a test of your faith in the scheme as a whole. Have faith. The conspiracy may go on much, much longer than expected—and you even expected delays. Have faith. The side that becomes demoralized as the war goes on will be the one that loses. You will be struggling for your own survival and question whether any of this is worth it after all. Have faith.

14: Willpower

You do not deserve victory, especially in a fight that you have decided to pick. You are not guaranteed victory at any point, even after the deed is done, and you must truly desire the end that you aim for throughout the entirety of the conspiracy. Make sure your enemy remains overconfident, because they won't want to win as badly as you do. They will simply believe that they deserve to win. That is not want. That is not will. That is not enough.

15: Earn favor

There are outside parties, those that are not your enemy and not your teammates, that you must win over. A conspiracy must have favor in the eyes of others to succeed. This may come through sympathy or guilt or pride or any other viable emotion. No matter what, others must come to support you and advocate for your conspiracy for a victory. You must win them over decisively and they will lead you to the desired end.

16: Aftermath

Once the monumental moment that is supposed to represent victory comes to pass, the end is not near. The conspiracy must still be kept under lock and key for the foreseeable future. It is a mistake to bring it out into the open too quickly if at all. You will fail or at least weaken your effect if you haven't actively thought about what you will do once the deed is done. It is tempting to reveal yourself, but it is too soon. Maintain your secrets and remain hidden. The dust has yet to settle.

17: Settlements

The desired end is to have your enemy thoroughly defeated and debilitated that they cannot be a true threat to you ever again. This is the end. If anything less is done, your enemy will continue to be your enemy and you will have an ongoing war to fight. Don't let this happen. Settle, and settle for good. 

18: Oops

At the end of any conspiracy, there will be unintended consequences. There will be people affected that you did not wish to harm, even when peace has come. New precedents may be set once you are revealed as a conspirator, your actions may spawn actions by others with similar motives, and you may embolden other people to do similar things for less noble reasons. These are made apparent at the end of a conspiracy, but perhaps they are better suited for the mind of the one who simply contemplates conspiracy. Don't underestimate what you will do on accident.


Again, these are takeaways from the book and not my own pieces of advice to a conspirator. I don't particularly think you should or will be inspired by this book to go start a conspiracy and see it all the way through to its finish. It's a rare feat for even rarer circumstances, but it exists for a reason.

I highly, highly recommend that you go read the book for yourself. If nothing else, it is an amazing story, and along the way you will be sure to pick up plenty of valuable life lessons. This is only a small selection of what you might learn through this book.

As Ryan wrote in my copy of the book, use this book for good. Or at least try to.

Diego Segura