Lessons from Conspiracy by Ryan Holiday

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Books / Tuesday

Conspiracy is only $1.99 this week as a Kindle e-book. Even if you are not going to read it soon, it’s a book that is timeless. So make sure you grab a copy!

I shouldn’t repeat authors (I already talked about Holiday’s Perennial Seller in Week 2) and I didn’t plan on doing so. But his latest book, Conspiracy, was gifted to me by a friend who said that I needed to read it. I am so grateful to her.

Conspiracy is about how Peter Thiel, using an uncommon set of tools, managed to bankrupt Gawker Media. There’s a lot of profiles that can give you the extensive background but the strong version is this:

Gawker outs Peter as gay in 2007. Peter gets mad because of this. He conspires against Gawker by hiring a team of lawyers to look in possible lawsuits that would be a death blow to Gawker’s finances. These lawyers find one with Hulk Hogan’s sex tape that Gawker posted and talked about. Peter finances the lawsuits from behind the scenes and manages to get a $140 million verdict against Gawker which puts them out of business.

That’s quite the story so there are many lessons to learned. Let’s dive into them.

Chutzpah: Progress doesn’t happen on its own

One of the things that we take for granted is progress. We think that given enough time, we will have solved most problems. Things like global warming, water shortages, epidemics. Instinctively, even I think in the next 50 years, these won’t be the issues we will be grappling with.

But that’s just not the case. Progress happens when a lot of smart people use a lot of brainpower and resources to solve a set of hard problems. This isn’t a given fact. Someone needs to put in the work to make this happen.

Thiel saw a problem – Gawker was a salacious bully that was at the mercy of the online advertising incentive structure. The more clickbait-y the article, the more money they make. It’s not difficult to overreach when you’re in this business.

When they overreached with Hulk Hogan, Thiel and his lawyers capitalized on it. Gawker should have seen this coming – when you’re playing on such dangerous grounds as Gawker was, there is no scope for mistakes. But more importantly, Peter didn’t just chose to do nothing about this organization that had infringed on his privacy.

Whatever your views on the verdict or on Thiel’s actions, it is refreshing to see even the powerful get out of their need to please everyone and color inside the lines – to do something that requires chutzpah. That’s how change is made.

Look at how instead of the what

One of the most refreshing things about Ryan’s take on this is that he is unapologetic about his intentions – he wants to explore the idea of conspiracy in his rawest form. It’s not to take sides or make judgements but to understand how power is wielded towards own’s ends.

This is very good because once you know the principles, you can apply it to a cause of your own choosing.

This kind of judgement-free writing and thinking is so rare these days that I want to thank Ryan for this. It truly sets a high bar for others.

Don’t mess up the endgame

My grandfather taught me chess around when I was in 3rd grade. I’d always seen games start off with the full board – this was about the only thing I knew about chess at this point but I felt confident that this was correct! Instead, my grandfather started off with 2 pawns each and our respective kings. His reasoning?

You could do all the work in the world, whittle me down to a few pieces, but if you don’t understand how to use space to your advantage to finish me off in the endgame, it’s all for nothing.

I was completely blown away about this.

Paper.Paper Tools.18.jpg

Coming back to the book and the story, Thiel botched the endgame. By failing to control the narrative around his involvement, Gawker was portrayed not as the bully, but the bullied. Even those who despised Gawker came to its defense because Thiel was a public multi-billionaire. It’s obvious to plan till the moment an action is completed. What separates the good from the great is how you deal with fallout. The 2nd and 3rd order effects. The unintended consequences.

As my grandfather said, if you mess the endgame, all your effort goes down the drain.


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