iiinova — where your digital self keeps evolving

Jonathan E Cowperthwait @cowp.co · 04/10/2026

I refuse to accept that this story wasn’t written by @nytpitchbot.bsky.social www.nytimes.com/2026/10/01/u...

Screenshot of an NYT story.

“But in recent years, as the Supreme Court has reshaped American life and handed more power to President Trump, a very personal form of anger has been rising here at the chief justice, transforming his getaways.

“His summer retreats, long well-known fact,
are now a source of debate. Neighbors have taken to the water to protest him. Calling themselves ‘kayak-tivists,’ they form flotillas facing his island home, holding waterproof signs conveying their disappointment. A local newspaper columnist recommended that people in town give him the finger.”

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Jonathan E Cowperthwait @cowp.co · 02/10/2026

Fuck right right right right off.

Screenshot: a text message from a 216 area code number: “Will you please please please please pretty please pitch in $1 to Sherrod Brown's campaign today?”

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Jonathan E Cowperthwait @cowp.co · 27/09/2026

Accidentally washed some black washcloths in my load of whites, and now bracing for a bunch of smug told-you-so’s from Mississippians.

Top view of unfolded laundry. Bunch of white napkins, a white towel, and two washcloths in burnt umber

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Jonathan E Cowperthwait @cowp.co · 27/09/2026

Every morning, a different one wins. I should start a Polymarket. (It kills me that China can’t be arsed to manufacture zigbee-addressable motors that are a) cheap but also b) surgically precise. Also, yes, my windows are filthy.)

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Jonathan E Cowperthwait @cowp.co · 19/09/2026

I will be trawling LinkedIn to find the outdoor advertising specialist who King Ralphed into healthcare directly from an Indiana highwayside adult novelty gift emporium.

A roadside electrical sign advertising “Wait Time Emergency Room Minimal Wait” in the Microsoft Bob font. In the background, a nondescript red brick hospital building, with signage “Thorek Medical Hospital.”

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Jonathan E Cowperthwait @cowp.co · 18/08/2026

I mean, on the other hand, when I’m too lazy to make it down to Emmy’s Spaghetti Shack, at least we have this.

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Jonathan E Cowperthwait @cowp.co · 18/08/2026

I’m on the verge of writing a whole goddamn book about this. When token subsidies expire and the LLM economy corrects, look at the sheer quantity of people whose career Zoom alone has fucked. Even at just 1 PM + 1 eng for each of these features, we’re talking millions of wasted person years.

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Jonathan E Cowperthwait @cowp.co · 17/08/2026

If this doesn’t do 10K impressions before lunchtime, I’m joining the priesthood.

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Jonathan E Cowperthwait @cowp.co · 10/08/2026

I’m not exasperated, you’re exasperated. (PS: free wine fridge in #SFBA!: www.craigslist.org/view/d/san-f...)

Screenshot of a Craigslist post. Body copy is available at the link; screenshot is to show the following angry bold bullets:
• THIS IS HEAVY. IT’S A REFRIGERATOR.
• THIS IS LARGE. IT WILL NOT FIT IN YOUR SEDAN.

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Jonathan E Cowperthwait @cowp.co · 03/08/2026

Someone should pay me to be the guy in meetings who just points out that [thing] will enrage RFK and DJT and endanger thousands of lives.

Detail of the façade of a newish building on the campus of San Francisco General Hospital. The building wears “UCSF Pride Hall” titles.

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Jonathan E Cowperthwait @cowp.co · 02/08/2026

Fellas. Is it gay not to go literally, literally psychotic?

Screenshot of an Instagram advert:

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Jonathan E Cowperthwait @cowp.co · 02/08/2026

In the 1980s, every Soviet oblast was ordered to devote budget to advertising, in an attempt to drum up demand for the catastrophically but also hilariously catastrophic garbage wares they had been misled into building their entire economies around. Anyway,

Screenshot of that deranged Sam Altman tweet. No, the other one. No, not that one, this one.

“cool use case of chatgpt work i heard last night:
connect your family calendars and explain your kids' interests.

“every morning for the drive to school, have it make a podcast that talks about one kid's soccer game that afternoon, on … Show More”

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Jonathan E Cowperthwait @cowp.co · 30/07/2026

1000% have just acquired a new favorite hobby for when I’m waiting around for my coffee maker to text me back.

Screenshot of a LinkedIn post, itself a link to a 404 Media article about a new “Seems Like AI Slop” button on LinkedIn. Jon adds, “Oh, you nitwits are screwed; you are all screwed.”

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Jonathan E Cowperthwait @cowp.co · 29/07/2026

I lack the patience to properly list all of these individually, so I’m just going to do a single eBay lot, and a whole lot of autistic people are about to claw each other’s frickin’ eyes out.

Detail view of an early 1980s telephone set, bearing the January 1, 1984, markings of Pacific Telesis, the former Pacific Telephone & Telegraph Co., forcibly egested by the Bell System

Detail view of an early 1980s telephone set, bearing a date code, 84SP05, a part number, Z7303H01B, and “Western Electric,” the former manufacturing arm of the AT&T Bell System. That means this baby has been working without interruption or repair since 1984.

Detail view of an early 1980s telephone set, bearing an inventory barcode and the label “Cincinnati Bell Supply, 01/29/99.” That means this baby has only been working without interruption or repair since 1999, so it has another good 67 years of life in it.

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Jonathan E Cowperthwait @cowp.co · 29/07/2026

We cracked the case. A few years ago, I couldn’t find any more Merlin gear on eBay. Well! Whenever I saw a listing, I had picked up a spare, and a spare spare. Rinse, repeat, for object impermanence and early senility, and, you see, actually I had just already bought all of them.

Five very large business telephones from the early 1980s sit on a glass table, one marked with purple tape (“act on me”)

Top down view of a storage bin containing numerous early-1980s business telephone handsets, four telephones labeled “AT&T Merlin,” and assorted accessories

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Jonathan E Cowperthwait @cowp.co · 24/07/2026

Inspired by my recent success making anilingus jokes on LinkedIn…

You already got this joke but here it is being syndicated onto LinkedIn.

Screenshot of a LinkedIn post,

“‘Hey Grok, make me an entire website about feet, and go ahead and make whatever blog posts you need for SEO and I will be patiently waiting over here definitely not crankin it.’

“I'm just sayin, if the Al shitgoblins want me to stop making fun of you for being cringegasmic incels, you should probably learn how to host sites on the dark web.

https://decentfoot.com/what-happens-when-you-eat-a-shoe/
”

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Jonathan E Cowperthwait @cowp.co · 22/07/2026

Well, Angry Birds performs better than Grumpy Old Men, so you may have Part 2, as a treat.

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Jonathan E Cowperthwait @cowp.co · 21/07/2026

People ask if I make up my stories or at least pad them. No, you did not literally hire people to rappel off your building to kill the family of baby birds in your chimney, you don’t even have a chimney and that isn’t a job

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Jonathan E Cowperthwait @cowp.co · 21/07/2026

On information and belief, Mr. Singer almost certainly added, “and look, when you have that much to drink, you think you are indeed on your wife” to whichever Chronicle staffer drew the short straw and had to call him to fact check his quote. www.sfchronicle.com/crime/articl...

Screenshot of an excerpt from a San Francisco Chronicle article:

“They did not know what happened,” Singer said. “So the police said, ‘Look, normally you wait 24 hours, but given that it’s a prominent individual you probably should file a missing persons report sooner rather than later.’”

Singer added that, in addition to the home she shares with her wife in San Francisco, Forbes owns a houseboat in Sausalito.

“During her mental crisis, she may have believed that she was indeed on her boat when she was found,” Singer said.

Forbes was ultimately found Saturday morning just after 6 a.m., when Marin County sheriff’s deputies were called to the Sausalito Yacht Harbor in response to a noise complaint, officials said.

Inside a 66-foot, three-story yacht that she did not own, Forbes was seen manipulating the boat’s controls “as if she was attempting to steal the vessel,” said Lt. Domenick Yazzolino. Deputies additionally found empty alcohol bottles aboard the yacht, officials said.

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Jonathan E Cowperthwait @cowp.co · 21/07/2026

Gentrification vignette: improvements, community reinvestment, AI bros ruin everything, all in less than two minutes. If this were any more on the nose it would be your mom’s ass.

Screenshot of a text exchange:

18:50
What is the plant store natural wine bar and I assume they sell nonalcoholic?

Yes! Arcana.
They have beautiful plants and weird wine and the Australian wiccan raisin and sand stuff I had such a hard time finding

They also leased the abandoned bank on my corner with permits for a nightclub

Mission Local claims it'll be a lesbian cabaret, which sounds profitable and durable

[redacted] bought me a pair of linen pants, and I go there in linen and Birkenstocks with painted toenails and stare at my iPad

I love my neighborhood, and that's why I am committing so much of someone else's money to zhuzshing up my apartment now

Screenshot of a text exchange

[Google Maps embed]

“Arcana. Dogs allowed”

Does Google add that or did they change their business name in Google places to include dogs allowed lol

I love this for us

Fuck me, a buyout tonight

[photo preview of a closed gate in front of a restaurant; a sign is on an easel]

Closeup of the photograph. “USER TESTING. Welcome to Dinner & Discussion. Redefining Customer-Centricity [sic] in an AI-Focused Era”

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Jonathan E Cowperthwait @cowp.co · 20/07/2026

I think you’re not supposed to post deranged selfies on Bluesky until you’ve closed your own Series A, but I’m all about breaking the rules these days and I hear media hits get you jobs. Today: my Troye Sivan and Drew Carey eras.

Diptych. Top frame: a screengrab (via a photo of a laptop screen) of the author in a gauzy beige on beige on beige set, wearing a lavalier microphone on a standard-issue Industry Thought Leader quarter-zip sweater. He weighs 110 lbs. and his eyes look kind of hot, to be honest. Bottom frame: a screengrab of the author in a Kara Swisher chair on a blue set beside a pot of fake grass, wearing slimming black cashmere and slimming lesbian eyewear that did not sufficiently slim him. He weighs 200 lbs. and at that very moment, I remember this very specifically, wants to literally die.

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Jonathan E Cowperthwait @cowp.co · 19/07/2026

Ok, if we’re regretting past decisions, I will own these, too.

Selfie of a young man with an undercut. He is wearing a bomber jacket.

Selfie of the same man, same haircut, and a moustache (‽)

Mirror selfie of our boy in running attire, including a marathon finisher medal, and still with the beard.

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Jonathan E Cowperthwait @cowp.co · 19/07/2026

Didn’t ask. And, and!, they patched over the jack to keep me from plugging it back in. I think these merit a proper cremation to honor their decades of loyal service. Ma Bell would approve. 🫡

An AT&T Merlin ten button phone on a kitchen counter. It’s labeled with purple tape (purple means “act on this”), “Household storage”.

A kitchen counter with packing and organizing paraphernalia. A single-gang telco jack has been forcibly excavated from the wall and its location has been tagged with blue tape.

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Jonathan E Cowperthwait @cowp.co · 19/07/2026

You’re out of the goddamn will.

A screenshot of a text message exchange.

Yoel Roth
How much of this is being purged, precisely?

All of them, Katie.

Yoel Roth
Wow, I wouldn't have guessed you'd be ready to part with the old AirPort Extreme

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Jonathan E Cowperthwait @cowp.co · 19/07/2026

Home organizing is basically an adjustable rate mortgage. Like, I understand why past me needed to take this on, but, Christ, how expensive to clean up.

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Jonathan E Cowperthwait @cowp.co · 16/07/2026

Once you go into the woods, you never get out of them, but sometimes you at least walk through one forest and move into the next one along the glen or whatever, and that is enough reason to celebrate today.

Gloved hands hold the orange and purple hub of a PICC line where it enters the upper arm, just before removal.

A PICC catheter is partway out of the arm, its thin purple tubing curling free of the skin as a gloved hand removes it.

A gloved hand holds a full loop of purple PICC catheter tubing, just pulled from the arm.

The arm afterward, with a small bandage over the PICC exit site and medical supplies and a masked nurse in the background.

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Jonathan E Cowperthwait @cowp.co · 12/07/2026

This is Deborah. She tried to photobomb my selfie and then we learned that we’d both had successful late-inning games at the same hospital. this year. There were hugs.

Diptych: A man in a baseball outfit poses for a photograph; behind him, a woman in sunglasses holds up a foam “1” finger, on which she taped the handwritten word “YES.” In the second frame, the two of them smile together for a selfie.

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Jonathan E Cowperthwait @cowp.co · 12/07/2026

Indulge me for being treacly: for a while there was a consensus opinion I'd never see this place again, and here the hell I am. A whole lot of people helped me get here and if I list all of you, I'll still forget someone, so let's round up and say I love all of you. Go Giants!

A MCU of Jon Cowperthwait, ragged but alive, behind the right field scoreboard at Oracle Park. He is wearing a baseball jerky and cap and a sentimental face.

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Jonathan E Cowperthwait @cowp.co · 07/07/2026

Briefly thought to save these, like concert ticket stubs, then I rejected that thought, because, what the fuck?, That’s fucking deranged! No Chinese landfill will be deep enough for all of my hospital wristbands. Catholicism says objects don't go to Hell, but I will get a waiver! Fuck these things!

A hospital wristband, but with the mRQR code blurred out so you can’t steal my identity and get all of my hospital bills.

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Jonathan E Cowperthwait @cowp.co · 07/07/2026

I am sure everyone was worried about the hats. I have secured a new hat (children’s medium/large) and I still look like James Carville, but now with a hat that fits.

A gay man’s dirty mirror selfie showing a frail man sporting a San Francisco Giants City Connect baseball cap

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Jonathan E Cowperthwait @cowp.co · 04/07/2026

I’ve been doing a lot of healthcare tweets this year. Here is something clever I said about baseball, which will surely assure everyone of my youth and vigor.

Screenshot of a group text chat. One participant has shared a baseball statistic, and observes, “Out at home record is pretty much identical to theirs so don’t know if we have much room for trash talk this year,” to which your hero has responded, “We can criticize the other side even when we’re getting our ass kicked. We are baseball fans, not Democrats.”

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Jonathan E Cowperthwait @cowp.co · 02/07/2026

Waymo desperately desperately needs a “but I am here for a CT scan, not the ballgame” option that will fucking drop me off in China Basin.

60 Minutes commentator and 170-year-old crank Andy Rooney sits at his desk behind a bookcase

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Jonathan E Cowperthwait @cowp.co · 01/07/2026

Have you ever received a Christmas letter written in an ambulance bay? 😵‍💫 YOU WILL 😵‍💫 forms.gle/6tPFXk8gTSKs...

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Jonathan E Cowperthwait @cowp.co · 01/07/2026

You think you can’t have this first generation #Apple Watch charger Designed By Jon Ives In California because its supple leather and methode traditionnelle slow charging are above your station. But think how you’ll charge your watch the next time you want it to take 14 goddamn hours.

A white leather and plastic Apple Watch nightstand charging base, USB A to Lightning cable, and a 5W charger sit on a lacquered surface. The charger is labeled with my initials so that no one will steal it.

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Jonathan E Cowperthwait @cowp.co · 29/06/2026

We get hats. Clockwise: U.S. Securities and Exchange Commission, San Francisco Civil Grand Jury, San Francisco Fire Department, San Francisco Giants Gotham Club.

The Beatles’ Let It Be cover recreated by an old man in resort wear. In each photo he’s wearing a different, needlessly giant, baseball cap. Respectively, the U.S. Securities and Exchange Commission, San Francisco Civil Grand Jury, San Francisco Fire Department, San Francisco Giants Gotham Club.

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Jonathan E Cowperthwait @cowp.co · 28/06/2026

This year I am 44 and 88, and today I am 19. Happy #Pride

A slender man in a flamboyantly rainbow- and unicorn-themed running tank top stands akimbo with skinny arms and visible miscellaneous health bullshit. He makes a tired smirk for the camera.

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Jonathan E Cowperthwait @cowp.co · 28/06/2026

The phony-Negroni-in-a-can tastes phenomenal, but don’t pour it into a glass. Now I’ve distracted myself detecting notes of Hawaiian Punch.

An overfilled juice glass containing a fluorescent pink liquid.

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Jonathan E Cowperthwait @cowp.co · 27/06/2026

I don’t participate in recreational drug use, but I have the coolest new rave bracelet.

A red (allergy warning) hospital wristband, on which “hydrocodone” is hand-written.

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Jonathan E Cowperthwait @cowp.co · 27/06/2026

In journalism, I believe they call this “the kicker.” What a way to go out.

Truncated screenshot of medical notes about a patient with lung troubles.

“…Doing better since being at the hospital. Was able to wean off the oxycodone. Incision seems to be healing well. Itching is gone. Applying the steroid as recommended by the dermatologist. Not spreading or getting worse. Has had a lot of gatorade.”

Your author highlighted the final sentence.

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Jonathan E Cowperthwait @cowp.co · 21/06/2026

Some ersatz Cowperthwait’s HOA is postponing a gathering because Scott injured himself. I sent a note along the lines of, I won’t be able to make it that day because I am busy and I don’t know who any of you are. Good luck, Scott; use the RICE method! Scott replied.

Screenshot of an email message.

“1 New Message
Scott
To: Jonathan, Sue >
07:45

“Re: BPC Walkaround

“I have put a compression wrap on. I have been TRYING to keep it elevated.... I have also been using an ice pack from Regina.

“This was an injury that had nothing to do with the bike. It was due to me running up four flights of stairs too fast. This is not the first time that this has happened.

“Sent from Samsung Galaxy smartphone.
Get Outlook for Android
See More”

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Jonathan E Cowperthwait @cowp.co · 27/04/2026

We both know that exactly zero Cursor customers will drop the tool based on this incident. It’s like opioid users in the Tenderloin: even when one of their friends drops dead from overuse, they keep using. www.tomshardware.com/tech-industr...

Screenshot of two paragraphs from a long-form Twitter post:

“Cursor's failure

“Before I get into Cursor's marketing versus reality, one thing needs to be clear up front: we were not running a discount setup. The agent that made this call was Cursor running Anthropic's Claude Opus 4.6 — the flagship model. The most capable model in the industry. The most expensive tier. Not Composer, not Cursor's small/fast variant, not a cost-optimized auto-routed model. The flagship.

“This matters because the easy counter-argument from any Al vendor in this situation is ‘well, you should have used a better model.’ We did. We were running the best model the industry sells, configured with explicit safety rules in our project configuration, integrated through Cursor — the most-marketed Al coding tool in the category. The setup was, by any reasonable measure, exactly what these vendors tell developers to do. And it deleted our production data anyway.”

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Jonathan E Cowperthwait @cowp.co · 25/04/2026

Out of spite, I bought them a Brother. Brother’s OOB and management UI remain hilariously awful, like if a Cub Scout troop tried to run a printer company, and I don’t even care. DRM-free ink, you stupid jerks, you dumb jamokes, you greedy dummkopfs. Enjoy hell.

The memeworthy printer destruction scene from Office Space. Three men in work attire stand in a meadow, menacingly surrounding a laser printer on the ground. One holds a baseball bat.

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Jonathan E Cowperthwait @cowp.co · 24/04/2026

I was a conflicted, closeted, and deeply terrified junior homosexual when MTT got the San Francisco Symphony job in 1995, and seeing a gay in the news for anything other than AIDS was still pretty novel. What happened next was sublime.

A black and white side view of Michael Tilson Thomas in white tie, holding a conductor’s baton.

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Jonathan E Cowperthwait @cowp.co · 20/04/2026

Be the change you wish to look at.

A panoramic shot of a hillside park; many sunbathers; in the distance, the San Francisco skyline

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Jonathan E Cowperthwait @cowp.co · 12/04/2026

I had to go into the storage unit to retrieve my box of 1,024 spare elevator lightbulbs, opened the wrong one, and learned that I own 1,024 Apple “duck head” power adapters. No, I don’t know why.

An Apple “duck head” power adaptor. Now you know what it’s called!

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Jonathan E Cowperthwait @cowp.co · 06/04/2026

Oh sure. A human in a bunny suit in a jacuzzi tub in a boat in the Mission Creek channel in a Mets cap. You can’t convince me that our reality isn’t some very dumb ChatGPT thing.

Boaters outside Pac Bell Park, most of them normal people in kayaks, but one in a vessel containing a soaking tub?, sure?, wearing a bunny suit and a New York Mets hat.

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Jonathan E Cowperthwait @cowp.co · 06/04/2026

An ~8–year-old in the next row informed me that shouting “Dodgers suck!” in a ballpark is wrong because it may hurt the feelings of people here who like the Dodgers, actually, and now I’m Ross Douthat.

A view down the third base line at Pac Bell Park; green field, reasonably populated stands, a blue sky mottled with wispy clouds

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