What Ghost Writing for Tech Executives Taught Me About the Small Peepee Paradox
And how it explains almost everything
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There’s a strange ritual practiced by lower class men in America. You see, there are only two things that really matter for a man here:
the size of your bank account
the size of your genitals
One is often a proxy for the other.
If you hang out with other working class men, everyone knows that everyone else is broke so there’s no point in trying to flex about having $20 more in your checking account.
Which means that most young men are in a constant poker game, bluffing about the size of their genitals. It’s a strange ritual for sure.
But the ritual is poisoned from the start by a deep, in-your-face homophobia. The very act of verification—the only way to “win” the game—is the ultimate taboo.
Even considering pulling an FDR makes you “gay.” Its one big, stupid, never ending escalator of insecurity bringing you straight to Hell. But there’s a subtle, counterintuitive logic going on here: the larger your genitals, the less you feel like you need to tell everyone.
Think about it. The person who talks the most about how big their dick is, always inevitably has a small pee pee.
This is what I like to call the small peepee paradox.
The more time you spend convincing others that you have a large penis, the smaller it actually is. And those who spend little or no time doing so get branded as being small. Instead of being a celebration of what is, the boast is a desperate bid to fill the void where a big dick should be.
And that’s kind of fucked up, right? It’s strange. It’s crude. But worst of all, the social consensus is the complete opposite of the truth.
This is just one tiny example of insecurity manifested in daily life.
But you can see it everywhere.
You can see it when someone claims they read Dostoyevsky but its obvious they’ve only skimmed a wikipedia page. You can see it every time a boss belittles their subordinates. You can see it every time someone tries to assert dominance.
The foundation of our whole damn civilization is a deep, trembling insecurity.
That’s not a bug, motherfucker, it’s a feature.
For a long time, I was convinced this was a unique pathology of the world I inhereted. The specific, performative masculinity of my white trash friends & family in our cramped, poorly heated living rooms.
But it wasn’t. It’s an epidemic of insecurity from top to bottom. Maybe even moreso at the top.
Desperate to escape my inherited poverty, I sold my soul to the tech bros and joined the laptop class.
It’ll be better, I thought. I’ll be able to drop these caveman status games and focus on building things, I thought. The work will speak for itself, I fucking thought.
After I got in, they booted my ass out of the product side pretty quickly. There was vomit on my sweater already from my spaghetti code.
The thing I was actually good at was technical writing. Teaching people how the code works.
But the tech bros don’t really care about that shit. So instead, the next few years were spent ghostwriting–massaging the big egos and big feelings of the c-suite reptiles.
Executives, founders, even a fucking billionaire.1
And that was when the disillusionment kicked in. Hard.
Because I realized they were doing the same exact thing my white trash brethren were doing. Of course, it was slightly more sophisticated than flexing about their penis size, but not much more sophisticated.
The tech bros did a software update on the small peepee paradox. And like most updates, it failed to fix the bugs and ironically created even more bugs. Enshittification at a sociological level.
They want to be innovation incarnate, heralded as the second coming of Steve Jobs himself.
I knew a founder like this. She wore the mask. Hard. Sometimes, I wondered if there was a person behind it.
She was a Wall Street banker who pivoted to crypto because you can dump on retail without having to actually build or do anything. She liked the money but loooved the validation. I’ve seen recovering meth addicts fiend for their next fix less than she craved flattery.
And damn she got it. From everyone. Regrettably, even yours truly. I was even good at it, God help me.
We had these recurring meetings where whoever was leading the meeting rotated from week to week. One time I had to lead the meeting.
I opened with a poem about what a great leader she is. Tweeted it out later that day and tagged her to RT. Pulled that kind of stuff on a daily basis…
Are you cringing? You should be.
In my defense, this was the first and only time in my entire life I was financially stable. The only time I wasn’t a prime candidate for Squid Game. The only time I could afford to take my cat to the vet.
The entire job was a humiliation ritual, a battle royale to see who could kiss her ass the most.
And damn did it get kissed—so much so that there was no ass left, just a glob of lipstick that stretched out for 6-7 inches behind her, leaving a synthetic, animal tested, deep red for a trail.
But the worst part was the cruelty.
You would stay up to 10pm ghost writing her “thought leadership” blog and she would call it “cringe” and demand you do it again. One time, the entire marketing department dropped everything for a month to help her write one blog… on her PERSONAL BLOG.
And she scrapped it anyway.
She was the ringmaster, and we were the dancing monkeys. If your dancing failed to amuse her, she shot bullets at your feet until you “took ownership” and upped your game.
It was like the most extreme sexual humiliation fantasy you’ve ever heard of, but without any of the sexiness—or consent—performed daily on Slack & zoom for years.
The “oh fuck, this woman is the devil” didn’t happen online though, but at a company offsite.
During a morning run, she got stung and went into anaphylactic shock. A coworker, a genuinely great guy, carried her panicked, swelling body back to the hotel so she could get an ambulance.
It was a traumatic, human moment. At the next all-hands meeting, she tearfully recounted the story, praising the “hero” who saved her. And…
She named the wrong person.
SHE NAMED THE WRONG FUCKING PERSON.
She accidentally thanked someone else with a similar sounding name. No one corrected her. The moment came and went with the same casual callousness we knew all too well.
Shit like this is just the tip of the iceberge–the things I can easily share without providing a wall of context or identifying details–but this kind of thing was the disgusting, banal norm.
That guy got a tiny taste of what her favorite ghost-writer’s daily, lived experience was like.
She made my life a living hell.
I was mad for a while. A long while. But for as mad as I should be, I can’t help but to feel a hollow, aching pity for her.
It wasn’t personal because it couldn’t be–there wasn’t person in there. Only a sad sociological feedback loop that was as toxic for her as it was for us.
I always wondered: what has to happen to a human being that they act like this?
Maybe her daddy didn’t love her. Maybe she was second best to a superior sibling. I don’t know and probably never will. There was, however, something horribly, horribly wrong with her. Like, “do you have a god damn soul” type shit.
She always reminded me of that one dude who always found a way to segway the conversation to his penis size. “I need to call Guinness world records, one of these days, bro.” Then you pull his pants down and see something smaller than a clit.
This overwhelmingly obsessive striving for status is a sign of less, not more.
It’s a cope. There’s something missing.
Ignorance where insight should be. A narcissist where a leader should be. A baby carrot where a penis should be.
It’s the small peepee paradox all over again. Or, whatever the gender-neutral Sillicon Valley equivalent is.
And you might not believe it when I tell you, but this woman–this monster–was the rule, a rule I never saw an exception to.
Tech is a petri dish for this pathogen. The disease I’d observed in my youth mutated in the rarified air of corner offices, growing far more sophistictaed and sadistic than it had any right to.
Maybe this is what Jesus meant when he said, “it is easier for a camel to go through the eye of a needle than for someone who is rich to enter the kingdom of God.” I don’t think he was saying rich people are going to Hell. Maybe they’re already there.
We live in a society where its trendy to post guillotine memes and tweet #EatTheRich but after having intimately known some of these motherfuckers…
I just kinda want them to get some help.
For their sake. For our sake. For civilization’s sake.
Because whatever was wrong with my former ringmaster is wrong with a lot of them.
Sadly, I cannot name and shame, but there is a good chance I worked for someone you have heard of. But I’m not trying to get Epsteined, so we’ll leave it at that.





The framing that helps me understand people better is that 1 out of every 40 people don’t have a functioning conscience, and the other 97% don’t realize that our brains are stuck 100,000 years ago hunting and gathering with large cats stalking us. 99% of our problems would be solved if all of us truly grasped that we can’t escape the Savannah and if we let fewer anti-social people have control of society.
Another extremely relatable post. We worked so hard to escape these performances only to perform for new people in different ways.