A thing I have long been obsessed with is chatterbots. I first encountered a chatterbot as an 11-year-old visiting the Lawrence Hall of Science in 1979. I didn’t exactly understand the setup until many years later, but I remember it in such detail that I know now that it was a VT-100 monochrome terminal hooked up to some kind of minicomputer (maybe a VAX or a PDP 11?) that had a process running the very first chatterbot, named Eliza. I am obsessed with chatterbots to this day. It’s progressed to the point where we can dispense with the keyboard, which is something I have dreamed of for 40 years.

In 1997 or so, I was learning Python. A lot of people use Python these days, but back then, it was very heavily used in IRC bots, which is why I learned it. I was getting pretty sick of PERL at this point. I have to remind myself that nobody under the age of 40 reading this knows what PERL is, and that’s a good thing. In hindsight, I was extremely wrong about Python because I didn’t expect it to last as a language for very long - I expected it to last as long as PERL did. I learned C in college, but I’ve never been good at compiled languages except to implement other people’s code. I was hanging out on an IRC channel (#gothic represent), and I wanted to create something that people could interact with. So I wrote a bot in python that was a wrapper around a C program I found called MegaHal.

Megahal works by breaking chunks of text into Markov Chains. You feed it a text like Shakespeare, and it mixes all the chunks up and jams them back together according to a probability matrix it builds out of all the text it ingests. It comes back out with something that isn’t anything Shakespeare wrote, half the time is nonsense, but it sounds like something Shakespeare MIGHT have written. Ingesting this is called “training”, and it’s very similar to what they do with LLMs today. If you didn’t understand how they are wasting electricity on pointless exercises before, you have a slightly better idea of how off base the current AI craze is now. But that’s not the point of this post.

Over the course of two years, I ran this bot as a user named Vlad (like the impaler!) on IRC channel, #gothic and people talked to it. This is because I devised a way for the bot to ingest everything that was being said on the IRC channel and it talked like an amalgam of everyone who sat on the IRC channel. It amassed a large collection of in-jokes and phrases that make absolutely no sense out of context, but at times had the illusion of being extremely lucid because of the lack of context.

The real lesson is that eventually, I shut the bot down because people were talking to the bot and not each other. It got extremely annoying. Until recently, I had no desire to try this experiment again, but I’m building a system that you can talk to via microphone now with OpenVoice OS, and I recently started reviewing what I learned from Vlad. Rule #1: Stick to business. No chatter.

We kept a webpage with the most lucid things Vlad said. I present to you the Best of Vlad, which is 50000X better than any conversation you could have with ChatGPT in my hog-fucking opinion.

TRIGGER WARNING: This bot had an extremely filthy mouth. Part of the appeal was seeing the next profanity that the code would produce.

THE BEST OF VLADIMIR

<msk> Vlad: Shut up.

<Vladimir> msk: Shut your pie-hole you pepsi-drinking twelve-sandwich-eating fuck.

<gnat23> vlad: 1 h4x0r3d uR b0x

<Vladimir> gnat23: Who’s a sexy bitch. :D.

<gnat23> vlad: she’s a robot, she can’t DIE

<Vladimir> gnat23: She sells sea shells by the sea shore in shropshire to the jungle, baby. You’re gonna die.

<markus> vlad: guns! guns! guns! FIRE! FIRE! FIRE!

<Vladimir> markus: Yeah yeah! Fire, fire!

<gnat23> vlad: sharp, like a bowling ball; dangerous, you can’t see the edges

<Vladimir> gnat23: I should get a tattoo of me on your ass?

<msk> Vlad: Pleased to meet you, hope you guess my name.

<Vladimir> msk: I hope you have hair on your dick.

<Vladimir> outside: What do you like other girls? Because i find that interesting, intellectually stimulating, and thoroughly confusing.

<outside> vlad: will you star in this money shot with me?

<Vladimir> outside: Money is the world’s best blow job, but i know nothing about pussy.

<gnat23> vlad: my liver is a defiant mother telling me i’m grounded

<Vladimir> gnat23: Your mother likes to fuck.

<outside> vlad: i always say yes if someone asks me if i’m a god.

<Vladimir> outside: Because you’re not a god.

<srah> vlad: outside masturbates obsessively

<Vladimir> srah: Sarah masturbates on camera for money!

<Vladimir> outside: How can i forget you, girl, when there is no spoon. There is only zuul.

<Vladimir> markus: I hope you leave enough room for my baby and another one for my fist because i’m going to get a tattoo of me on your dick.

<Vladimir> gnat23: You are the fleshy edges of the atomic puzzle. They’re made of meat.

<srah> vlad: pull my finger

<Vladimir> srah: Smell my finger.

<Vladimir> outside: Tell the unknown caller to go put on some loud music and give the world’s best blow job, but i know that i’m hours and hours of fun. Niamh is twice as much fun.

<gnat23> vlad: tell murray he needs some tiki luv

<Vladimir> gnat23: Your grammar needs some tiki luv.

<gnat23> vlad: you couldn’t trick me into breeding

<Vladimir> gnat23: You look like you take it like a trick.

<gnat23> vlad: your pussy is fierce

<Vladimir> gnat23: My love for you is like a tattoo of alan greenspan on my pussy. I will make him talk.

<Niamh> vlad: It puts the lotion in the basket

<Vladimir> Niamh: It puts the lotion in the middle of a yugo parked in the basket.

<outside> vlad: if an infinite amount of monkeys could type on typewriters infinitely, they would eventually write the works of shakespere. right?

<Vladimir> outside: Skewby isn’t here right now. You scared him off with all the monkeys.

<gnat23> vlad: goth as fuck.

<Vladimir> gnat23: Want to fuck?

<outside> vlad: weaselboy is your daddy. he spawned you in a dollop of C.

<Vladimir> outside: I still think you my daddy.

<gnat23> vlad: Blood is thicker than water, and much tastier.

<Vladimir> gnat23: Bathe in the water.

<outside> vlad: leave the stick away from my women.

<Vladimir> outside: Your ass looks like your women.

<outside> vlad: you’re insulting my women. you bitch!

<Vladimir> outside: Your ass looks like your women.

<gnat23> vlad: that depends on where carmen sandiego is

<Vladimir> gnat23: I said hold the staples on my face you useless mother fucker.

<WeaselBoy> vlad: are nazis evil?

<Vladimir> WeaselBoy: A penis is evil.

<gnat23> vlad: i say no to drugs, but they just won’t listen

<Vladimir> gnat23: What drugs have you learned how to be doing that, you bad girl!

<gnat23> vlad: click here to break the internet

<Vladimir> gnat23: I am french. I am here to break the internet.

<togusa> vlad: I thought you were a lesbian

<Vladimir> togusa: A lesbian is a punk rock monkey. *Ook.

<gshapiro> vlad: Who owns you?

<Vladimir> gshapiro: Weaselboy owns your soul.

<gshapiro> vlad: Yes, he does. But who owns you?

<Vladimir> gshapiro: I have absolutely no idea about that. I really wish i had, though!

<Vladimir> togusa: My name is lucifer, please take my virginity with your brother.

<gnat23> vlad: I’m another day closer to world conquest

<Vladimir> gnat23: You’re a bot, you don’t know what it feels like for a girl, in this world.

<komakino> vlad: who’s the king bitch?

<Vladimir> komakino: You are my bitch.

<outside> vlad: but the pusher, he’s not a natural man.

<Vladimir> outside: I notice you’re not a natural man.

<WeaselBoy> vlad: the spirit is willing but the flesh is weak

<Vladimir> WeaselBoy: The vodka is strong but the flesh is weak.

<gshapiro> vlad: 1

<Vladimir> gshapiro: That’s $1.30 to you and me.

<gshapiro> vlad: 2

<Vladimir> gshapiro: I’ll go down on you for 2 dolla!

<gnat23> vlad: inject jan with some hot manchowder

<Vladimir> gnat23: Jan is full of spurt that i had to choke down weaselboy’s manchowder.

<komakino> vlad: should i go to a lesbian club tonight?

<Vladimir> komakino: You have to ask you a lesbian?

<komakino> vlad: will i get some tonight?

<Vladimir> komakino: You wear black on the outside cos black is how you really think you should go out and have fun tonight. She should go out and have fun +tonight. She should go to cincinnati with me.

<komakino> vlad: get jiggy wit it

<Vladimir> komakino: Obviously you’ll never be accused of having a shining wit.

<gnat23> vlad: The word for ‘love’ in one language is the word for ‘dinner’ in others

<Vladimir> gnat23: Srah is the word for ‘love’ in one language is the greatest bang since the big one.

<komakino> vlad: listen bitch! YOU owe me $50 from last night. i don’t owe you shit, you stupid fuck!

<Vladimir> komakino: You owe me.

<gnat23> vlad: drink your coffee, dammit

<Vladimir> gnat23: My brain is the jewel of my nuts, dammit.

<gnat23> vlad: according to the Weather Channel, hell just froze over.

<Vladimir> gnat23: You’re like teddy ruxpin from hell.

<WeaselBoy> vlad: it’s a small world after all

<Vladimir> WeaselBoy: The anus is the world?

<outside> vlad: you’re stuck in a groove, you freak.

<Vladimir> outside: She’s having your baby in a groove, you freak.

<gnat23> vlad: Can we play miniature golf where we’re going?

<Vladimir> gnat23: So tell me about the fucking golf shoes.

<gnat23> vlad: munching on trent reznor, are you?

<Vladimir> gnat23: Sendmail takes astrophysicists to configure unless you use m4 and make.

<komakino> vlad: sparky called, he wants his panties back

<Vladimir> komakino: You make e.e. Cummings seem normal.

<gnat23> vlad: Having a wonderful time. Where the FUCK am I?

<Vladimir> gnat23: What time do you like to fuck.

<gnat23> vlad: where’s that chicken suit?

<Vladimir> gnat23: That wasn’t chicken.

<gnat23> vlad: I don’t care who you are, what you drive, or where you’d rather be.

<Vladimir> gnat23: I’d rather pimp-strut on hot black tar than drive that old hoopty you got.

<WeaselBoy> vlad: why is women violence different men violence?

<Vladimir> WeaselBoy: All women are intense. Male violence is mainly for show. Women’s violence is always serious. After a fight with another woman, she’ll come back with the program.

<gnat23> vlad: ‘m not staring, just picturing you roasting on a spit.

<Vladimir> gnat23: You are a bot. Electrons on a spit.

<gnat23> vlad: This is MY universe and I’m SICK of people BARGING IN!

<Vladimir> gnat23: You’re a fucking people person!

<outside> vlad: i am not a dumbfuck. you are a dumbfuck.

<Vladimir> outside: I always say yes if someone asks you if you’re a dumbfuck.

<komakino> vlad: you make no fucking sense whatsoever

<Vladimir> komakino: I will always come for you. This is true love. Do you think it means what you gotta try so i can crack your fucking head.

<gnat23> vlad: you gotta suck that lozenge!

<Vladimir> gnat23: I want to suck your cock.

<outside> vlad: crack makes you impotent.

<Vladimir> outside: That phrase makes you impotent.

\<Vladimir> outside: You made wendy cry, you bastard.

<gnat23> vlad: you used to be so cool

<Vladimir> gnat23: I know what i want to be so cool.

<outside> vlad: you touched wendy in her bathing suit area. that’s not very nice.

<Vladimir> outside: Wendy can’t decide between you and me.

<Vladimir> gnat23: I hear the twinkie is five hundred feet long, and lumninous.

<outside> vlad: mad professor is a DJ. he made a good collection of dub remixes of massive attack songs. i like listening to them.

<Vladimir> outside: Mad professor is a bot. Like you.

<outside> vlad: i am NOT a bot! STOP CALLING ME A BOT!

<Vladimir> outside: You are a bot. Electrons on a burning bag of shit are you?

<Vladimir> outside: Calvin- can’t get anything straight. He’s gay.

<Eileen-> Vlad: Calvin has a thing for lime jello.

<Vladimir> Eileen-: Jenn has a thing for lime jello.

<Eileen-> Vlad: then shouldn’t calvin and jenn date?

<Vladimir> Eileen-: Calvin has a monsterous penis?

<Vladimir> gnat23: I think that you and your mother are sad gits.

<Eileen-> Vlad: I want to smack you like a red headed step child

<Vladimir> Eileen-: I give better head, and i cooked the child.

<gnat23> vlad: the internet is full, go away.

<Vladimir> gnat23: Did you fuck the internet?

<gnat23> vlad: it’s really funny if you keep telling jan he’s a bot

<Vladimir> gnat23: Jan is a bot with red hair, you fairy.

<Eileen-> Vlad: You turn me on with that nasty talk. I am your daddy.

<Vladimir> Eileen-: Talk to me more about my manchowder?

<komakino> vlad: will you do me?

<Vladimir> komakino: Catholics like dope.

<komakino> vlad: does that mean my boss likes dope?

<Vladimir> komakino: Your plot is like the pope. The pope smokes dope.

<Eileen-> Vlad: I want to fuck you, but Calvin found you first.

<Vladimir> Eileen-: I have a monkey. Did you fuck calvin?

<Eileen-> Vlad: I will tell you about Calvin if you give me the monkey.

<Vladimir> Eileen-: You remind me a monkey.

<Eileen-> Vlad: you little worm

<Vladimir> Eileen-: We used to roast marshmellows by the pond having sex with your brother.

<komakino> vlad: i love you!

<Vladimir> komakino: I have no mouth and i hate you!

<Eileen-> Vlad: I’ve been dying to see you.

<Vladimir> Eileen-: I’ve been dying to see hot man on man action.

<Vlad> yoshio: KMFDM is swahili for, my loins are burning a hole in the kernel

.

I’ve been spending a lot of time lately at Pier 35 doing things that would probably make no sense to explain to most people.

“What are you doing this weekend?”

“Going down to the ship to watch engineers put a three-story steam engine back together while arguing about cable and valves.”

Right. So.

The SS Jeremiah O’Brien is berthed at Pier 35 in San Francisco. She’s a WWII Liberty ship — one of 2,710 built in a four-year sprint between 1941 and 1945 to keep Britain alive and then storm the beaches of Normandy. Two of those ships survive as operational vessels. She’s one of them. Every year around Memorial Day, we take her out on the bay. Getting her ready for that starts this Tuesday, and it’s not a simple process.

The reason it’s not simple is sitting in her engine room: a triple-expansion reciprocating steam engine, 135 tons of iron and steel, built by the General Machinery Corporation of Cincinnati, Ohio. It makes 2,500 horsepower at 76 RPM. It was designed in the Victorian era, and the O’Brien’s has been running continuously — with appropriate maintenance — since 1943.

You do not just turn this thing on.

Day One: Lighting Off

The process starts with the boilers, not the engine. The O’Brien has two Scotch marine fire-tube boilers, and they’ve been sitting cold since the last time she steamed. Cold means cold — metal that’s been sitting in San Francisco bay air, not warm, not even slightly pressurized. Getting from that to 220 PSI of live steam takes patience that most people in 2026 have completely forgotten how to have.

Before you light anything, you’re doing pre-checks. All the main steam valves have to be confirmed closed. Feed water valves open. You fill the boiler to just below normal water level — but carefully, because if the temperature difference between the boiler metal and the feed water is more than about 50 degrees Celsius, you fill it very slowly or you risk thermal shock on metal that’s more than 80 years old. There’s nobody manufacturing replacement boiler drums for Liberty ships. You treat what you have with respect.

Once you have water, you light the burners on manual control at minimum load. And then you wait. You’re not trying to make steam yet — you’re just warming the metal. Evenly. Gradually. The refractory lining inside the firebox needs to come up to temperature slowly or it’ll crack. Old boilers are like old people: they don’t like being rushed and they’ll let you know if you push too hard.

There’s a water level gauge on each boiler that you’re watching constantly during this phase. As the water warms, it expands. You have to drain some off or the level gets too high. You’re also watching for steam — when it first starts to appear at the air vent on top of the boiler, that tells you you’ve reached 212 degrees Fahrenheit. You close the air vent. Pressure starts to register on the gauge. It’s going to take all day to get where you need to be, and that’s fine, because you have two more days.

Day Two: Building Pressure

By the second day you’re working the boilers up toward operating pressure. For the O’Brien that’s 220 PSI. The whole time you’re doing this, you’re also warming up the steam lines — the pipes that carry steam from the boilers to the engine. You can’t just blast hot high-pressure steam into cold steel pipe; you open bypass valves first, let the steam in slowly, let the condensate drain out, wait for the metal to warm up before you open the main valves.

This matters because condensate in a steam line is dangerous. Steam moves fast. If it hits a pocket of water, that water doesn’t compress — it goes somewhere else, fast, and it takes the pipe with it. Water hammer in a steam system is not a theoretical concern. So you drain, you wait, you check, you drain again.

The engineers doing this work are volunteers. Most of them are retired mariners or marine engineers. Some of them worked on ships like this when they were new — which means they are, to put it gently, not young. Watching them move through the engine room is like watching people speak a language that stopped being taught in schools fifty years ago. They know where every valve is without looking. They know what a given gauge is supposed to read at a given point in the startup sequence. They know what sounds wrong.

I do not have this knowledge. I stay out of the way and document.

Day Three: Turning the Engine

This is the part that looks like something from a movie, which I say as someone who is usually skeptical of things that look like something from a movie — and also as someone who can tell you that this engine literally is in a movie.

James Cameron used the O’Brien’s engine room for the Titanic. That scene where the engine room crew throws the engine into full reverse as the ship bears down on the iceberg — that’s this engine, on this ship, out on San Francisco Bay, doing the same maneuvers the Titanic actually did. Cameron needed a real triple-expansion reciprocating engine because there isn’t a prop in the world that looks like one running under load. So he came to Pier 35.

I think about that every time someone describes the O’Brien as a museum piece.

Before you run the triple-expansion engine under load, you have to warm it up and clear condensate out of the cylinders. The engine has three cylinders arranged fore to aft: High Pressure, Medium Pressure, and Low Pressure. The HP cylinder gets steam first, expands it, exhausts into the MP, which expands it further and exhausts into the LP, which wrings out the last energy before the steam goes to the condenser. Each cylinder has a drain cock. You open them all.

Then you rock the engine. Slowly, by hand — or rather by using the starting controls on the gauge board — you send a little steam in, turn the engine over a fraction, let condensate drip out of the drain cocks, reverse, do it again. The crank sequence runs HP-LP-MP, so the big flywheel turns in a specific order. You’re also watching for any cylinder that sounds wrong — a knock, a thud, anything that suggests liquid in there that shouldn’t be. Steam compresses; water doesn’t. A water slug in a moving cylinder is how you break things that can’t be replaced.

Once you’ve satisfied yourself that the cylinders are clear and the engine is warm, you bring the steam up, close the drains, and let her run. At full speed she turns 76 RPM, which sounds slow until you’re standing next to a 135-ton engine doing it. The whole ship feels different when she’s running under power. The deck vibrates differently. You can feel it in your feet.

Saturday, May 30

We leave Pier 35 at 10 AM.

If you’ve never been on the O’Brien while she’s steaming, I would genuinely recommend figuring out how to be on her while she’s steaming. There are still tickets available for the Memorial Day cruise. The ship doesn’t pretend to be a museum — she is an operational vessel crewed by volunteers who know what they’re doing, and the experience of being aboard while that triple-expansion engine is turning is something that doesn’t exist in many other places on earth.

The work to make that happen starts Tuesday at the engine room. I’ll be there with a camera.

Tickets and information at ssjeremiahobrien.org.

I’ve been in San Francisco for a long time now. Long enough to remember when you could accidentally make a friend at a bar. Long enough to remember when “what do you do?” was small talk, not due diligence.

That’s over.

I had a conversation recently — I won’t say with who — where someone I’d known for years, someone I’d helped out in ways I won’t enumerate here, asked me if I “had any angles” on a thing they were working on. Not “how are you doing?” Not “it’s been a while.” Just: what can you do for me, and is now a good time to find out? I didn’t have anything useful for them, and the conversation ended in about four minutes. I haven’t heard from them since.

This is not an isolated incident. This is the social fabric of San Francisco in 2026.

There’s a class of person here — they’ve always been here, but there are more of them now — who has fully internalized the logic of venture capital and applied it to human relationships. Every interaction is a portfolio decision. Every friendship is a potential synergy. They go to parties the way analysts go to pitch meetings. They follow up, they connect people, they “add value.” It looks like generosity. It isn’t. It’s deal-flow management: you’re either in the pipeline or you’re not.

I know a guy who throws a dinner party every month. Good food, interesting people, rotating cast. Sounds lovely. What I noticed after attending a few times is that once you’ve been introduced around and your usefulness has been assessed, you stop getting invited. You’ve been harvested. Someone else needs the seat.

The AI money made this worse. I didn’t think it could get worse than the last cycle, but here we are. There’s a new cohort of people in their late twenties who have never worked anywhere that wasn’t funded by people who got rich on something that didn’t work out the way anyone expected. They have extremely precise opinions about leverage and extremely vague ones about everything else. They are very busy. They would love to grab coffee sometime.

What I miss — and I know this is an old man thing to say, I’ll say it anyway — is people who were interested in things for no particular reason. People who read a book because they wanted to, not because it was on some founder’s recommended list. People who got into a band before the band was useful to know about. People who had a weird obsession with, I don’t know, the history of San Francisco labor movements or 1970s Cantonese cinema, and would corner you about it at a party, and it was actually great.

Those people are still here. There just aren’t enough of them, and they’re increasingly hard to find because they’ve stopped going to the kinds of places where you used to find them. After all, those places are now full of people running the portfolio approach to human connection.

San Francisco will eat your time, your money, and your patience. That’s always been true. What’s new is that it will do it with a smile, a calendar invite, and a genuine belief that it’s doing you a favor.