So there’s this 22-year-old CEO named Avi Schiffmann who’s selling an AI pendant that listens to everything you say and texts you snarky comments about your life. He put up a bunch of ads in the NYC subway. People hated them so much they covered them in graffiti. And now he’s doing a photoshoot in front of the vandalized ads for The Atlantic, grinning like he just discovered fire.
Let me pour myself something strong while I explain why this is the most beautifully absurd thing I’ve seen all week.
The product is called Friend. Not “Assistant” or “Helper” or “Companion.” Just Friend. Capital F. Like you’re so pathetic you need to buy a friendship from a company that probably burns through venture capital faster than I burn through Marlboros. The device hangs around your neck like some kind of technological albatross, constantly listening to you and everyone around you, then firing off AI-generated texts to your phone. Texts that, according to reviews, are mostly antagonistic.
So it’s a friend that insults you. Which, to be fair, describes most of my actual friends. The difference is my friends don’t record every word I say and feed it into some server farm in god knows where.
The subway ads were these mostly white billboards with minimal text, leaving plenty of room for New Yorkers to express their feelings. And express they did. The ads got absolutely destroyed with handwritten commentary, the kind of organic public feedback that money can’t buy. Well, unless you’re Schiffmann, who seems to think the vandalism was all part of his master plan.
“The picture of the billboard is the billboard,” he told The Atlantic, which is the kind of pseudo-profound nonsense you come up with when you’re 22 and everyone keeps telling you you’re a genius.
He also dropped this gem: “Nothing is sacred anymore, and everything is ironic.” Which he’s apparently repeated in multiple interviews, because when you find a meaningless phrase that sounds deep, you milk it like a drunk trying to squeeze one more drop out of an empty bottle.
Here’s where it gets really good though. Schiffmann claims the company wasn’t involved in graffitiing their own billboards, despite mysteriously identical phrases appearing on multiple ads. Because nothing says “authentic grassroots hatred” like verbatim repeated messages across different locations. Sure, buddy. And I’m just drinking this bourbon for the antioxidants.
But wait, there’s more. When asked to describe what Friend actually is, Schiffmann said it’s like an amalgamation of your therapist, best friend, and journal. Then he topped that off with: “This is what I said a while ago, and I don’t think a lot of people liked it, but I would say that the closest relationship this is equivalent to is talking to a god.”
Talking. To. A. God.
I’ve talked to a lot of things in my time. Bartenders, mostly. The occasional lamp when I’ve had too much. But comparing a $99 pendant that sends you snarky texts to a deity is the kind of hubris that would make Icarus say “maybe pump the brakes there, chief.”
The reviews of this thing are exactly what you’d expect. Tech journalists have tested it and found that it not only fails to deliver on its promises but actively antagonizes the wearer. Which raises an interesting question: who exactly is the target market for a device that listens to your every word and then insults you? Masochists with trust funds? People who find regular self-loathing too inefficient?
There’s also the small matter of privacy. This thing is constantly listening. Not just to you, but to everyone around you. Your spouse. Your kids. The stranger sitting next to you on the bus who’s confiding in their actual human friend about their divorce. All of it getting sucked up into Friend’s servers, processed by AI, turned into content for your personal roast session.
But here’s my favorite part of this whole carnival: Schiffmann told Fortune that “it costs me an unfathomable amount of money if you actually use the product.”
Read that again. The CEO just admitted that his business model works better if people DON’T use his product. It’s like opening a restaurant and hoping nobody orders food. “Profitability is ideal,” he said, “but right now it costs me an unfathomable amount of money if you actually use the product.”
This is the tech startup equivalent of a hot dog vendor saying “please don’t buy my hot dogs, they’re bankrupting me.” Except with more AI and less self-awareness.
And yet, here we are. The Atlantic is writing about him. I’m writing about him. The vandalized ads are probably more effective marketing than the clean ones would have been. He’s testing the theory that any press is good press, which is a theory that’s worked out great for about a dozen people in history and disastrously for everyone else.
The whole thing reminds me of those conversations you have at three in the morning when everyone’s had too much to drink and someone starts talking about how we’re all just data points in someone else’s simulation. Except Schiffmann sobered up, got funding, and actually built the simulation. Or at least the microphone for it.
Look, I’m the last person to moralize about privacy or healthy relationships or responsible technology use. I write a blog called Wasted Wetware. I’m not exactly a role model. But there’s something deeply strange about a world where a 22-year-old can raise enough money to convince people to wear surveillance devices that insult them, then pose for magazine photoshoots in front of ads that people hated so much they defaced them.
The really funny part? He’s probably right that it was all part of the plan. Not because he’s some marketing genius, but because in 2025, the best way to sell something is to make people hate it loudly enough that everyone hears about it. Outrage is the new advertising. Contempt is the new buzz. And if you can get people to vandalize your ads while simultaneously making them curious about what could possibly inspire such hatred, well, you’ve basically won the lottery.
Friend will probably fail. Most AI wearables do. We’ve seen this movie before, and it usually ends with a lot of expensive hardware gathering dust in desk drawers. But Schiffmann’s already preparing for that possibility, which suggests he’s either remarkably self-aware or has read the same cautionary tales I have.
Either way, I’m fascinated by the sheer audacity of it all. The confidence it takes to look at a world full of lonely people and think “what they need is an AI that listens to them constantly and sends them mean texts.” The conviction required to describe your product as god-like when it’s really just a very expensive way to get negged by an algorithm.
I need another drink.
Source: Cocky AI CEO Does Photoshoot in Front of His Subway Ads That Got Relentlessly Vandalized