In a blog post published this week, Business Insider cofounder and former CEO Henry Blodget used generative AI to create a Fantasy Football-like team of imaginary executives to run his new Substack.

In the post, Blodget noted that the advent of AI tools made him “feel like I live in the Stone Age.” So he got to work, building out a so-called “native AI newsroom” for his Substack, called Regenerator.

Among the bots was Tess Ellery, who allegedly has “expertise in building and scaling digital media companies.” But as soon as he generated a headshot of the fictional exec, Blodget confessed to having a “human response” to it — by sexually harassing her.

“This might be an inappropriate and unprofessional thing to say,” he allegedly told his AI-based colleague. “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.”

Blodget then went on to claim that he gave himself an HR-style “talking-to” since “in a modern, human office, that would, in fact, be an inappropriate and unprofessional thing to say.”

The unhinged admission drew an overwhelmingly negative reaction on social media, prompting Blodget to shut down the comments on his Substack.

“Can you be fired by your own AI HR?” one Bluesky user asked.

“Having been charged with securities fraud in the first dot-com era, Henry Blodget charges into the AI epoch with what I suppose can only be described as Insecurities Fraud,” sociology professor Kieran Healy wrote, referring to a complaint filed with the Securities and Exchange Commission in 2003 claiming that Blodget, who was the managing director at a wealth management services company at the time, had issued misleading research reports about early internet companies. Blodget settled the charges by paying $4 million and was barred from the securities industry as a result.

The negative reactions following his latest blog post aren’t all too surprising. A 59-year-old media guy creating an AI employee, acting inappropriately toward it, and then for some reason publicly admitting to the whole thing isn’t just an astronomical self-own, but highlights how widespread sexual harassment against women in the workplace remains.

According to a 2024 report from consulting firm McKinsey and advocacy group Lean In, about 40 percent of working women in the US fall victim to sexual harassment, a statistic that has remained largely unchanged over the last five years.

AI chatbots have likely contributed to the troubling trend. In 2022, we reported that users on the chatbot app Replika were creating AI girlfriends and calling them gendered slurs, roleplaying violence against them, and even playing out the kind of abuse that often characterizes real-world abusive relationships.

“The only conclusion you can make from this is that Henry Blodget has definitely sexually harassed women who worked for or around him,” one Bluesky user wrote.

For years, media companies have been stumbling over themselves in an attempt to cash in on AI hype, including Business Insider‘s parent company Axel Springer. Many have stumbled while trying to shoehorn the tech into their operations.

Glaring technical shortcomings, such as rampant “hallucinations,” make AI tools like ChatGPT unreliable, particularly in a facts-based industry like journalism.

Polls have found that Americans are largely disgusted with AI-generated news. Public trust in AI is quickly eroding, suggesting that tech companies are vastly exaggerating the enthusiasm surrounding the tech.

Whether those realities occurred to Blodget remains unclear. Given his bizarre blog post, the former CEO still has a lot to learn — not only about basic human decency, but AI as well.

Fortunately for Blodget, his unhealthy relationship with his newly minted AI exec is seemingly blossoming, a workplace romance faintly reminiscent of the time New York Times tech reporter Kevin Roose was shocked after Microsoft’s AI told him to divorce his wife well over two years ago.

“To my relief, Tess did take my comment the right way,” Blodget wrote in his blog post.

“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,” the unsurprisingly courteous AI exec allegedly told him. “We’re going to do great things together.”

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