54 Lessons for Entrepreneurs from Ryan Holiday’s New Book Conspiracy, on Peter Thiel’s Takedown of Gawker Media

Peter Thiel’s takedown of the once notorious Gawker Media has served as a modern-day case study on the ages-old conspiracy, and how to successfully carry one out.

Thiel — the preeminent entrepreneur, venture capitalist and political activist, best known for co-founding PayPal and Palantir Technologies — was driven to bring down Gawker, not only because of a story they ran in 2008 entitled ‘Peter Thiel is totally gay, people’, but because he felt that Gawker’s brand of clickbait journalism would censor the free exchange of ideas, stifle progress and ultimately drive more would-be entrepreneurs and world-changers to depression and suicide.

Ryan Holiday — decorated 31-year-old author of books such as Ego Is The Enemy and The Obstacle Is The Way — got the inside scoop, spending a considerable amount of time with both Thiel, Nick Denton — founder of Gawker Media, and other players on both sides of the conspiracy, distilling his insights and interpretations into his new book, Conspiracy: Peter Thiel, Hulk Hogan, Gawker and the Anatomy of Intrigue. Conspiracy represents a fresh change for Holiday who has made a name for himself by essentially repackaging the works of Stoic philosophers such as Seneca the Younger, Epictetus, and Marcus Aurelius, for a modern audience.

Conspiracy is packed with lessons one can apply, not only to carrying out a conspiracy — which few of you reading this are probably planning to do — but more so, lessons you can apply to business and life more broadly.

Below, I have highlighted my key take-aways from the book, and where I felt the inclination, I’ve added my own interpretations of how they might show up in business and in life.

54 Lessons and Interpretations

1 — The ignorance of how things really work opens us up to manipulation and closes us off from opportunities to advance our own goals.

This shows up in the corporate workplace where one’s diligence and technical competence are often no match for political jostling or a deep appreciation for realpolitik.

2 — The things people don’t say are precisely the things that need to be said.

While an entrepreneur might save themselves and their employee a moment of awkwardness by neglecting to pass on constructive criticism, their business suffers and so does their employee’s learning and growth. This is why author and hedge fund manager, Ray Dalio, swears by radical transparency in the workplace.

3 — Conspiracies have 3 phases:

planning

doing

aftermath

Essentially, the characteristics of any project.

4 — ‘The beginnings of all things are small’ — Cicero

Keep this in mind when building new habits. As James Clear — author of Atomic Habits — puts it, use the two-minute rule. Commit to going to the gym for example, for 2 minutes a day.

After a while, you will tell yourself, “well, I’m already here every day, I may as well train for a little longer”. By starting small, we do away with the overwhelm of seeing the forest from the trees and are more likely to stay the course instead of fall victim to instant gratification, especially once we start to see results.

5 — Conspiracies require patience and fortitude.

Carrying out any Herculean effort requires this. As former US President, Calvin Coolidge, said, “Nothing in this world can take the place of persistence. Talent will not; nothing is more common than unsuccessful men with talent. Genius will not; unrewarded genius is almost a proverb. Education will not; the world is full of educated derelicts. Persistence and determination alone are omnipotent.”

6 — There is evil in not acting, in assuming that a bad situation will resolve itself for you or that others will resolve it for you.

7 — ‘Gossippy newspapers are dogs for the public’s amusement’ Kiekergard

Seems not much has changed in the past couple of centuries.

8 — Negative expected value

Positive EV means that you can expect a positive long term result in a given situation and negative EV is the opposite. As a consequence, you want to bet as much as possible when you have a positive expectation and as little as possible when you have a negative expectation. Source: EVPoker

9 — According to Thucydides, the three strongest motives for men are:

1 fear

2 honour and

3 self interest

I would imagine that sexual conquests would fall under #3… unless of course, one is an altruistic lover. But then again, it’s hard to deny the involvement of self-interest in all forms of altruism.

10 — ‘Conspiracies are weapons of the people’ — Machiavelli

Available to every man

Used by the desparate

Feared by the powerful

11 — High agency person — Eric Weinstein

‘How do you respond when told “it’s impossible” — is that the start of a new conversation or the end of it?’

This is something that I expect of my team members. I never hear “it can’t be done” these days, because it’s not part of our culture and values to think that way. Anybody who does either doesn’t get hired or gets fired fast.

A question to tease this out of people when interviewing:

a) “Tell me about the last time you overcame something that you initially thought was impossible”; or

b) “Who do you admire that has accomplished the impossible, and why?”

12— “Combining with others constitues the most strategic move” — Lawrence Freedman

In business, one plus one equals three — providing you get the right person or people on the bus. Innovation and creativity too, are the result of new insights gained at the intersection of disparate ideas and people. See The Medici Effect.

13 — The briefcase technique

Something to try in your next sales meeting or job interview. Check out this two-minute video.

14 — ‘If everyone thought that way what would the world look like?’

This is how you win over ambition individualists with a soft spot for Ayn Rand’s novel, Atlas Shrugged.

15 — Plenipotentiary model: empowering trusted, skills people on your behalf to exwecute the bold vision you have craeted.

This is common amongst many high profile entrepreneurs, including the likes of Richard Branson, who when asked what the secret behind his success is, says, “I hire people smarter than me, give them a worthwhile mission and the tools they need to succeed, and get the hell out of the way”.

16 — ‘A startup is a small group of people that you’ve convinced of a truth that nobody else believes in’ — Peter Thiel

An interesting definition from Peter Thiel, and one that puts small business operators in a very different bucket — something I tend to agree with, because the nature of a startup is fraught with ambiguity whilst the nature of opening a barber shop or a gymnasium, nowhere near as much.

Another definition I like comes from Steve Blank, “I’ve concluded that great entrepreneurs are artists, artists in the true sense of the word”.

17 — ‘Patience and time — there is nothing stronger than these two’ — Field Marshall Mikhail Kutuzov (fictional character from Tolsyoy’s War and Peace)

See Calvin Coolidge quote above.

18 — ‘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.‘ — Jose Raul Capablanca

“Begin with the end in mind” — Stephen Covey, the 7 Habits of Highly Effective People

19 — Eye for an eye, tooth for a tooth — you just become what you hate.

20 — ‘All great victories come along the line of least resistence and least expectation- — BH Liddell Hart

In business, this applies when you’ve landed upon a value proposition that wows, one that solves big problems in a way that excites people, and in a way that is easily monetisable. As the author of 80/20 Sales and Marketing, Perry Marshall, says, when startups are struggling to gain traction “it’s not a marketing problem, it’s a value proposition problem”.

The opposite is joining a bloody red sea of a market, where you have to undercut competitors, work hard for tiny margins and essentially spend a ton of money on marketing, rolling a boulder uphill before you run out of steam (or runway) and it flattens you.

21 — ‘What do I know about this company that other investors don;t know?

Information asymmetry 101 — a key to not only investment but gaining a competitive edge in almost any domain.

22 — Only with information assymetry can you beat and dominate the market.

23 — ‘With the right conditions, a little boldness will make much more progress than timidity will ever protect.

24 — Slow and steady wins the race. But you need to decide which race to run.

So profound. As Peter Drucker said, there is nothing worse than the wrong things done right.

And as I said on the Startup Story podcast recently, there are thousands upon thousands of people — especially young people — who will never reach their potential in the corporate environment.

We should always look to cultivate a career at the intersection of purpose, our natural strengths and inclinations, autonomy, growth, and the ability to earn. Anything short of this often means we wind up being lesser actualized versions of ourselves and as a result, feel incongruent, depressed and turn to stimulants for a reprieve.

25 — Thiel’s default state is contradiction. Seeing trades and investments from a dozen perspections. He holds two antagonistically opposed ideas in his brain at the same itme.

Strong opinions, loosely held. Always challenge your own assumptions and look for what is most right, because absolutely right usually doesn’t exist and is limited by the information processed at our disposal.

26 — ‘A conspiracy is one long struggle in the dark’ — Lucretius

Like entrepreneurship.

27 — ‘Battle plans are great but ultimately subject to friction — that is, delays, confusion, mistakes and complications — Clausewitz

Or, “Everybody has a plan until they get punched in the face” — Mike Tyson.

28 — ‘The problem with Silicon Valley is that we often confuse a clear view with a short path — Jim Burksell

29 — The essential trait of a successful man is not only to persevere but almost a pervese expectation of how difficuly it is going to be. The earlier you spot and anticipate setbacks, the less demoralising they will be.

In business and in life, the healthier your relationship with adversity, the better you will respond when difficult situations inevitably arise, putting you in a league of your own.

As Ryan Holiday put it in his previous effort, the obstacle is the way.

Cultivate this relationship by getting out of your comfort zone often and try to learn new things that ultimately challenge your ego, all the while reminding yourself of Zig Ziglar’s famous maxim, “anything worth doing is worth doing poorly until you can do it well”.

30 — The general must not allow himself to be elated by good news or depressed by bad = Napoleon

A rather Stoic position, echoing the thoughts of Seneca and Marcus Aurelius over 1,500 years earlier. While we should indeed acknowledge and celebrate our wins, we shouldn’t get carried away with them, nor should we place too much emphasis on the applause of crowds, which are often misguided and empty.

By becoming overconfident, we can become complacent.

Don’t forget the hard work and luck that ultimately got you that success in the first place.

31 — It is difficult to study an enemy you don’t know exists.

How might you use this against your adversaries?

33 — Psychologically, people want to brag about things they’re not supposed to brag about.

The main weakness in any conspiracy is usually human nature — the more people involved, the higher odds of betrayal or reveal.

This is so me.

34 — Anybody with a guilty conscience can easily be led to believe that people are talking about them — Machiavelli

Sound familiar?

35 — The art of deception and confusion — Maskirovska(Russian)

36 — ‘Subvert him, attach his morale, strike at his economy, corrupt him, sow internal discort among his leaders. Destroy him without fighting him.’ — Sun Tzu

This is resonant US military strategist John Boyd’s OODA loop — observe, orient, decide, act. Providing you can get inside your enemy’s OODA loop, you can disorient them and defeat them. It is a form of what Napoleon knew as ‘controlled chaos’.

More specifically, it reminds me of the CIA’s Simple Sabotage field manual.

37 — Nero poisoning the soup

This is just a cool story.

Tasters routinely sampled all drinks and dishes to guard the family against poisons. But every system has its loopholes, and Nero exploited one of them. Since it was winter, wine was drunk warm, mixed beforehand with hot water. Britannicus’ cup was duly tasted and passed to him. But the drink had been made too hot for the young man’s liking. He pushed it away, and an obliging servant added melted snow to temper it. The drink, now containing the poison, was not tested a second time. Britannicus sipped it and fell stone dead.

38 — Being feared is good protection from a conspiracy. Being liked is the best protection.

Basically, don’t be a dick.

39 — If the ties that bind you are strong, you have a sense of purpose and mission, you can withstand great trials.

This holds true bigtime in entrepreneurship and in personal relationships. Values alignment is key. If I believe in radical transparency and extreme ownership, but my colleague believes in niceties and excuse-making, we are not going to have a meaningful working relationship.

40 — ‘What is the thing they have not planned for?’

Always be looking to attack adversaries here.

Resonant of, say, Norse Vikings, who would look for weaknesses in city gates and walls, where they would launch an attack from to increase their chances of successfully sacking a city.

41 — It’s a game of spouses too.

If you want to win someone over, win over their spouse.

42 — Culture transcends strategy.

To quote the ever-quotable Peter Drucker again, “culture eats strategy for breakfast”.

43 — ‘What our worst case and how does it stack up against their best case?’

44 — Hope is rarely enough against an opponent consumed by their cause with victory in sight.

Especially when that opponent has nothing to lose.

See the Vietnam War on an opponent consumed by their cause.

45 — ‘The greatest sin for a leader isn’t in being defeated. Iti’s in being surprised.’ — Frederich the Great

This is why you must measure, monitor and take action accordingly.

Seek out information from different people in your team, and outside your team, to gain a true understanding of market conditions.

Napoleon had generals provide him with regular reports from the field. It wasn’t that there were countless reports — there were few — but what made it work was the diversity of the reports. With this comes pattern recognition which sets the scene for better decision making.

46 — ‘It is much better to be the last mover’ — Peter Thiel

The contrarian strikes again and goes against the notion of ‘first mover advantage’.

I don’t know, Airbnb and UBER seem to be doing okay, despite numerous copycats that came afterward. Having said that, I’m falling into confirmation bias here — because Facebook came along long after other social networks like Myspace did. Not to mention Snapchat.

47 — ‘There is only one danger to a successful conspiracy; when someone is left who may avenge the dead prince’ — Machiavelli

So you must crush your enemies totally — Robert Greene

This is like those 1980s Jean Claude Van Damme movies where Kurt Sloane, or whoever, has the opportunity to finish his opponent, but for whatever reason, shows remorse and doesn’t, and inevitably and oh so predictably find ourselves with an additional 20 minutes of action.

Having said all of that, I’ve got a sudden hankering to watch Bloodsport.

48 — The best defence to speech you don’t like is to develop a thick skin.

Sticks and stones, people.

49 — Contrarians are usually wrong (Bezos).

The may be mostly wrong, but when they’re right, they’re really right. (Thiel)

Oooh…

50 — Amor Fati — love and embrace the good in what has happened

Another bit of Stoic goodness. In truth, there is a silver lining to any situation, no matter how bad it might seem in the moment. Getting broken up with for example, not only builds resilience but opens the door to a new and more fulfilling relationship.

51 — Realpolitik — the way things actually get done

a system of politics or principles based on practical rather than moral or ideological considerations

52 — One person’s liberation can be another’s oppression.

53 — Automation means the only thing left for human’s is:

Audaciousness

Vision

Courage

Creativity

A sense of justice

Something to remember for whenever the “AI will take our jobs” and “UBI” conversations come up.

54 — In these times of flux and upheaval, we need ambition the most.

Without ambition, there is only regression.

‍