Reciprocal Sycophancy, or Why It Is Wise to Heed the Fools

Scale-Up VC blog
7 min readJul 15, 2021

When we’re not calculating, scheming, or buying private islands, we VCs spend an astounding amount of time producing content. After actors and gurus, there is perhaps no profession more widely represented on the podcast scene. VCs blog as profusely as a C-list-celebrity-turned-president tweets. Andreessen Horowitz has launched an op-ed section. When we’re not writing books, we’re reviewing books for hallowed publications of impeccable quality, like Bloomberg.

Two aspects of VCs’ prolificness are surprising:

  1. that we have time for this at all in our 70-hour-plus work weeks and
  2. that so much of the content is so banal.

The explanation for #1 is the hope of replacing conversation with broadcasting. Instead of confabbing (repetitively) with existing and prospective portfolio companies and LPs, we create informal, educational, asynchronous, mass interactions. It beats formal business talks where people often prefer to play politics instead of exchanging ideas. Granted, it’s also a cheap-ish way of saying “Look at me! I’m smart with words, so maybe I’ll be smart with your money/company!”.

#2 is more puzzling. VCs are usually the smartest people in the room. Tech founders think they’re the smartest ones in the room, but then VCs come in and tell them what to do, so draw your own conclusions. VCs need to understand business and finance (not necessarily the same thing), law, tech, the science behind the tech, the sociology and psychology of investors, entrepreneurs, users, and competitors, and we need to be affable too. But some of our most renowned thoughts are just … so … hackneyed.

If this is your big idea, maybe think harder? (Image: pxhere)

How bad is it? Perhaps the most revered VC-authored book of the last decade, which was also taught as a course at Stanford, basically argues that capitalists want to achieve monopoly. I know. Take a breath. This concept is so radical that it is perhaps best explained in a 117-year-old board game recommended for eight-year-olds.

When VCs Ape Philosophers and Kings, Banality Results

Perhaps most shocking of all is the lost opportunity. VCs aren’t just bright, we’re also powerful. Tech startups have not only disrupted, but obliterated one industry after another in the last few decades. Just ask your favorite cabbie or newspaper editor. And VCs are the ones propelling that change. Those are our creations. We’re creating annual value that dwarfs many countries and changing the lives of billions, and yet we write blog posts arguing that a successful team needs acute people. C’mon.

Maybe we’re not obtuse despite our power, but because of it. Maybe we’re secretly intimidated by each other’s intellect and accomplishments, maybe we’re secretly really, palm-sweatingly apprehensive about making the wrong move, maybe we’re all just secretly desperate to be liked. Maybe in our desperation to avoid ridicule, we just say the safest thing we can and hope that everyone else is intimidated enough by us to praise it, or at least to fear criticizing it.

Lorenzo: maybe flattering him was pretty hard after all. (Image: Wikipedia)

This is reminiscent of sycophantic court philosophers, like Hegel and Machiavelli. As the rector of the University of Berlin and its prime philosophy professor, Hegel was also the semi-official court philosopher to Frederick William III, the Prussian king. It’s no surprise that he thought history was basically the process of God’s consciousness waking up and realizing itself, with a state that looked a lot like Prussia as its apogee. Machiavelli wrote his most famous book, The Prince, as a how-to guide for Lorenzo de’ Medici, one of the most powerful up-and-comers in early modern Europe. See, Machiavelli had just been imprisoned and tortured by the Medici family, and he thought a book of shrewd advice would reingratiate him. But how could he go wrong telling a 20-year-old duke that he can opt to be either feared or loved? What young, powerful man would not be flattered at the choice of becoming either Thanos or Captain America? Machiavelli couldn’t go wrong.

My thought is that perhaps we VCs all see ourselves as Hegel or Machiavelli, and we all see each other as Frederick and Lorenzo. We flatter each other with complimentary platitudes and hope a favor or two will come our way. The result is a term you’re sure to find on the Urban Dictionary, but to be safe, let’s just call it reciprocal sycophancy.

You Can’t Fool a Fool

Instead of aping philosophers, we might be better off taking fools as our role models, like Triboulet. Triboulet lived around the same time as Machiavelli, and he was the court fool under Louis XII and Francis I of France. He feared no one. Threatened with execution for insulting a mistress of Francis I, Triboulet was allowed to choose how he would be killed. His choice was “Good Sire, … I choose to die of old age.” Or after smacking the king on the behind, he excused himself by telling the king “I’m so sorry, your majesty; I didn’t recognize you! I mistook you for the Queen!”

Of course, Triboulet’s content was different from Hegel’s or Machiavelli’s. The fool never wrote a book, and old fashioned “yo mama!” jokes aren’t really explicit critiques of the monarchs’ power. Rather, the critique was implicit in Triboulet’s very existence. Just being there, the fool served to remind everyone that — no matter how much they might believe in divine right — the king, queen, and courtiers were also just people, not gods. They, too, could laugh and fart and make mistakes.

The fool didn’t critique what the powerful did; rather, he reminded them of what they really were (i.e. just people) and shielded them from the temptations of their own egos.

Get Real. Like the Fool.

To recap: when producing content, many VCs grandiosely propound banal ideas, just like court philosophers who flattered their patrons, whereas fools brought their benefactors down to Earth with derision.

I’ve implied that the fools’ approach is superior, but that’s not obvious. Why not flatter your peers by wrapping banal ideas in extravagant rhetoric? Why not play it safe by publishing uncontroversial, obvious ideas that your peers will accept and identify with? Why not cultivate an industry-wide self-perception of superiority? If superiority didn’t matter, neither would (having more) money. What’s the virtue in things like humility and fallibility anyway?

What is obvious is that we all — VCs, limited partners, founders, Uber drivers, “sandwich artists” — are all just people. For all our differences, we’re all capable of brilliance and gaffes. The frequency distribution is just a little skewed.

An aura of superior depth and infallibility, though, is just that. An aura. A phony projection. An unnatural glow. Reciprocal sycophancy relies on flattery, and flattery is just one party nurturing another’s idealized self-image. And since images are imposed upon an underlying reality, they require maintenance. Otherwise, cracks will appear, and the underlying reality will shine through.

Ironically, then, the underlying reality of the fallible, vain, covetous people is infallible. It’s reality. It doesn’t crack, and it can’t err. However, the image of infallibility, brilliance, and inherent superiority cultivated by the production of superficial (and superfluous) content, is fallible. It’s just an image — ephemeral, costly, fragile.

Wherever there are court philosophers, there is a king/queen/emperor. Wherever there is such an artificial hierarchy of images that deny the underlying reality that we’re all just people, it is just a matter of time before the fallible images of infallibility succumb to the infallible reality of fallibility. The scenario from the emperor’s new clothes, in which reality comes crashing through the image, revealing any assumed superiority to be false and the court philosophers to be worthless flatterers, is the inevitable outcome.

In fact, the court philosophers and their flattery are worse than worthless. They don’t just annihilate gains; they induce losses. Think about it: someone who can endure a fool’s mockery and accept the reality that the fool reinforces displays character. That’s someone who can take a joke, make a mistake and — perhaps most importantly — laugh at and learn from their own mistakes. Taken well, a fool’s derision can elevate a regular person to a person of character.

The emperor who succumbed to the court philosopher, however, doesn’t just fall down to the level of a person like any other, but falls down to the status of a vain idiot. The emperor wasn’t just duped, but duped thanks to his own vanity.

For VCs, vain dupability is more than embarrassing. It can be fatal. Remember the tailors in the story of the emperor’s new clothes? They were confidence men who recognized the emperor’s vanity, his ministers’ willingness to reinforce his image in the face of a contradicting reality, and the opportunity that this fragility offered. Silicon Valley is full of them. If a vain emperor is a fool (in the sense of an idiot, not a derisive reminder of reality), and a fool and his money are easily parted, these are the ones doing the parting.

So what’s the takeaway for vain VCs tempted to try their hand at writing or podcasting or vlogging and to play philosopher king?

Better to remain silent and be thought a fool than to open it and remove all doubt.

My ultimate point isn’t that VC is just a frivolous activity demanding mockery, like it’s all just a joke so whatever. My point is that VC is too important for hollow sycophancy. Our choices are monstrously consequential, so let’s get real with each other. The truth hurts — at least worthwhile truths do. If it doesn’t sting a bit, is it saying anything worthwhile?

If you want to find who’s really the smartest guy in the room, yellow boots and a feathered cap are dead giveaways. (Image: VirgoGem)

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