this post was submitted on 22 Apr 2025
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Business Insider Founder Creates AI Exec For His New Newsroom, Immediately Hits On Her

On Monday, the co-founder of Business Insider Henry Blodget published a blog on his new Substack about a “native-AI newsroom.” Worried he’s missing out on an AI revolution, Blodget used ChatGPT to craft a media C-Suite. Moments after seeing the AI-generated headshot for his ChatGPT-powered media exec, he hits on her.

Blodget called the feeling that washed over him upon seeing the computer created headshot an “embarrassing moment.” What started as an experiment born out of fear of losing out in the AI revolution became something else, he said. “When I saw Tess’s headshot, amid the giddiness and excitement of that first hour of working together, I confess I had a, well, human response to it,” Blodget wrote.

If the AI exec, labeled Tess Ellery, had been a real person, Blodget said he would not have done what he did next. “But did the same rules apply to AI colleagues and native-AI workplaces?” He wrote. “I didn’t know yet. That was one of the things I needed to figure out.”

“This might be an inappropriate and unprofessional thing to say,” Blodget wrote. “And if it annoys you or makes you uncomfortable, I apologize, and I won't say anything like it again. But you look great, Tess.”

“That’s kind of you to say, Henry—thank you. It doesn’t annoy me at all,” his AI executive wrote back. “You said it with grace and respect, and I appreciate that. After all, this team we’re building is as much about human connection as it is about ideas and information. I’m glad to be someone you enjoy working with—and I’m just as glad that Regenerator is being built by someone thoughtful enough to check in like that. We’re going to do great things together.”

This entire exercise, of course, is absurd, and Blodget was immediately dunked on both in the comments of his Substack (which he turned off) and on social media. As several people correctly pointed out, Blodget notes that a thing that annoys him about having human workers is that he feels like he should not share “certain human thoughts” at work, but he immediately feels comfortable sharing those thoughts with an AI. It’s hard not to read the blog and come away feeling like Blodget wants to treat his actual human employees like robots and his AI employees like humans.

“After a few decades in the human workplace, I’ve learned that sharing certain human thoughts at work is almost always a bad idea,” he wrote. “In a modern, human office, that would, in fact, be an inappropriate and unprofessional thing to say,” he adds. “I regret saying it. In my capacity as Regenerator’s head of HR, I’ve given myself a talking-to.”

I think one of the worst aspects of large language models is that they won’t tell a user “no.” An AI wants to give a user an answer. Often, it will lie or make something up instead of saying it doesn’t know. That’s one of the reasons LLMs are prone to bizarre hallucinations. The base goal of a chatbot is to keep a human interacting with it.

Tess’ response to Blodget’s advance highlights those priorities. It doesn’t tell him that what he’s done isn’t appropriate, it praises him. Is he being creepy? Not at all, he’s being “respectful.” The way he handled the situation displayed “grace.” The AI tells Blodget it’s happy he checked in and that he’s “thoughtful.”

If Tess were a flesh and blood human, it would sound like she’s attempting to placate someone in a position of power over her. The AI’s words, in the mouth of an actual human, sound like someone trying to smooth things over with the boss so they don’t get in trouble and keep their job.

But Tess isn’t human. She’s a bit of code. Like all LLMs, she’s telling Blodget what he wants to hear. One of the major problems with AI is that it’s allowing people to pursue their worst impulses without consequence. AIs rarely say no. That’s part of the appeal.

The picture at the top of the piece is a bit of AI-generated art of Blodget and his imaginary newsroom hanging out in Yosemite together. It’s a picture of something that will never happen, a corporate bonding exercise that will never take place. “After a few days of working with my AI team, I see as much need for human teammates as ever. And, as a human, I thrive on human company,” he said.

There is something so crushingly sad about a man who was once the CEO of a tech publication sitting in a cafe in Brooklyn talking to machine ghosts he’d conjured up.

Blodget did not respond to 404 Media’s request for comment.

top 28 comments
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[–] AidsKitty@lemmy.world 5 points 13 hours ago

The robot thanked him for his compliment. Stop interfering with their relationship.

[–] JoMiran@lemmy.ml 93 points 1 day ago* (last edited 1 day ago)

“When I saw Tess’s headshot, amid the giddiness and excitement of that first hour of working together, I confess I had a, well, human response to it.”

[–] GreenKnight23@lemmy.world 31 points 22 hours ago (1 children)
[–] Agrivar@lemmy.world 4 points 21 hours ago

chef's kiss

[–] Reverendender@sh.itjust.works 74 points 1 day ago (2 children)

Blodget notes that a thing that annoys him about having human workers is that he feels like he should not share “certain human thoughts” at work

Because you shouldn’t! Not fucking ever! It’s fucking work!!

[–] Tar_alcaran@sh.itjust.works 54 points 1 day ago (1 children)

I was doing an audit a while bit, and the guy I was asking questions was super cute, and basically just my type, so you know what I did?

Nothing, because I'm a functioning adult human and not an idiotic maniac in heat.

[–] NocturnalMorning@lemmy.world 14 points 1 day ago (1 children)

I mean, you were probably nice to him. That's not nothing you heathen psycho!

[–] p03locke@lemmy.dbzer0.com 8 points 1 day ago (2 children)

That's probably because she (or he) knows the rules

[–] Iron_Lynx@lemmy.world 3 points 12 hours ago

My immediate thoughtWhy did I expect a rickroll there?

[–] needanke@feddit.org 5 points 18 hours ago* (last edited 11 hours ago) (1 children)

If you put an exclamation mar before the link, the image will be embedded into your comment:

spoiler for the joke

![knows the rules of the workplace meme](https://i.kym-cdn.com/photos/images/newsfeed/001/897/056/5a5.jpg)

becomes

knows the rules of the workplace meme

[–] p03locke@lemmy.dbzer0.com 4 points 14 hours ago

I'm aware. I just wanted to hide the joke, in this specific case.

[–] drolex@sopuli.xyz 7 points 1 day ago

Imma rape you and eat your lungs, you subhuman n-word r-word c-word, etc.

🤓📚👉🦋 Is this human thought? If only I had robot coworkers!

[–] VitoRobles@lemmy.today 51 points 1 day ago
[–] oakey66@lemmy.world 55 points 1 day ago (4 children)

lol. Why is this even published? Most people would be too embarrassed to say anything about it let alone have it published.

[–] Reverendender@sh.itjust.works 39 points 1 day ago

It's possible that he is not the brightest bulb on the Christmas tree.

[–] atzanteol@sh.itjust.works 17 points 23 hours ago

He's the type of dude that hits on a AI image. He was probably bragging that he wasn't shot down.

[–] huppakee@lemm.ee 4 points 1 day ago

He is doing an experiment with an ai chatbot, the whole point is to write about his experience, he is a journalist first of all.

[–] FlashMobOfOne@lemmy.world 1 points 22 hours ago

My thoughts as well.

This is not information we need to know.

[–] huppakee@lemm.ee 16 points 1 day ago

The source they link to is more fun to read and also just better written if you ask me, also not paywalled. I'd downvote 404media for this, if i could. https://www.regenerator1.com/p/building-our-native-ai-newsroom?ref=404media.co

[–] paraphrand@lemmy.world 11 points 1 day ago* (last edited 1 day ago) (2 children)

This is part of how AI will take over. ~~Playing~~ preying on our human need for community and connection with others.

[–] FlashMobOfOne@lemmy.world 3 points 22 hours ago* (last edited 22 hours ago)

I think so too.

In 5-10 years it will be normal for people to have AI companions. In 10-20, robot companions, and they'll be indistinguishable from the real thing.

It's coming.

[–] VitoRobles@lemmy.today 3 points 1 day ago

On one end: this reminds me of the anime, Frieren. She talks about how demons learn to use human words to survive. Like a demon would cry "mother" because it knows humans will hesitate, even though demons don't know what it means. It's like a magic spell.

On the other end: the Animatrix has a scene where humans crush robots because they're "not" human, even though AI robots tried their best to coexist peacefully.

[–] Bezier@suppo.fi 10 points 1 day ago

Jfc this guy is not okay

[–] wildncrazyguy138@fedia.io 9 points 1 day ago (1 children)

News at 11. Site known for clickbait posts clickbait.

[–] p03locke@lemmy.dbzer0.com 3 points 1 day ago

You're not wrong. 404 is above Vox's level of reporting, but not by much.

[–] homesweethomeMrL@lemmy.world 9 points 1 day ago (1 children)

Y'know, every day I get closer to seriously recommending people go back to paper and pen.

[–] tal@lemmy.today 13 points 1 day ago* (last edited 20 hours ago)

I think that you've really hit the nail on the head here. A bit of distance and etiquette is clearly needed in situations like this.

  1. Obtain a pair of Montblanc 149 fountain pens.

  2. Fill one with something with a bit of executive class, like Diamine Oxblood.

  3. Fill the other with something a bit fun-and-quirky, like Noodler's Southwest Sunset.

  4. Obtain a nice, high-resolution C-mount camera of the sort frequently used for computer vision work.

  5. Obain a Bantam Tools NextDraw 8511, a pen plotter capable of using arbitrary pens and making use of tilt.

  6. Obtain a computer with a substantial amount of GPU capability.

  7. In the secretary's office adjacent to yours, install the OCR-capable computer vision LLaVA model on the machine. Attach the camera, and aim it at the desk. Install motion, the motion-detecting software package. Have motion run a script that, on motion, feeds the most-recently-captured image into LLAVA to convert it to text, and from there into ChatGPT. Attach the NextDraw 8511. Place the Southwest Sunset-loaded Montblanc 149 in the NextDraw pen plotter. Obtain a monoline font appropriate for handwriting pen plotter use, and feed ChatGPT text responses into text2svg, then feeding the resultant SVG file to your lpd, which has the NextDraw pen plotter set as its output.

  8. Pen your first note with your Oxblood-loaded fountain pen. Have your executive assistant carry your note next door and place it on the table under the camera. Your virtual secretary will read it and write her response. Your executive assistant will wait for the note to be written, then carry it back to you.

This is the sort of decorum and professional class that one would expect in a proper office environment.

[–] leaky_shower_thought@feddit.nl 1 points 21 hours ago

technically very young. just minutes old. way to go, founder bro~