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Summarize
Creepy: Business Insider co-founder admits to hitting on AI executive
Blodget apologized for the incident

Creepy: Business Insider co-founder admits to hitting on AI executive

Apr 23, 2025
10:20 am

What's the story

Henry Blodget, the co-founder of Business Insider, recently shared a weird incident on his Substack blog. He had used ChatGPT to create a media C-Suite for his new venture, Regenerator. An AI-generated executive named Tess Ellery (part of the C-Suite) was so lifelike that Blodget began hitting on her, which he later described as an "embarrassing moment" in his career.

Interaction

Blodget's response to AI-generated headshot

Blodget admitted his reaction on seeing the AI-created headshot of Tess was a "well, human response." He wondered if the same rules apply to AI colleagues and native-AI workplaces. His interaction with Tess raised questions about appropriate interactions in an AI-driven work environment. Despite fears of backlash from this incident, Blodget defended his actions saying, "If it annoys you or makes you uncomfortable, I apologize."

Response

AI executive responds to Blodget's 'flirting'

Ellery, Blodget's AI executive, responded positively to his compliment. She thanked him for his words and highlighted how human connection is important in their team-building process. The exchange raised questions about what relationships might look like in an AI-driven workplace. On facing backlash on social media for his treatment of AI employees, Blodget defended himself saying sharing certain thoughts at work is often a bad idea.

Dynamics

Reflections on human-AI workplace dynamics

Reflecting on his experience of sharing personal thoughts at work, Blodget noted how different it is with AI. He said while it might be inappropriate in a human office, he felt comfortable doing so with an AI.

Balance

AI team experience and need for human interaction

Despite his initial excitement about working with an AI team, Blodget soon realized the value of human interaction. "After a few days of working with my AI team, I see as much need for human teammates as ever," he said. This admission highlights the importance of maintaining a balance between technology and humanity in today's rapidly evolving work environment.