The $2 Billion Question: How ChatGPT Quietly Dismantled an Entire Generation of Startups

Photo by Levart_Photographer on Unsplash

A cautionary tale about building on shifting ground

I still remember the Slack message from my friend Jake. It was 2:47 AM — never a good sign.

“Dude, we’re shutting down. OpenAI just announced Custom GPTs. That’s literally our entire product.”

Jake’s startup had raised $1.2M six months earlier. They’d spent a year building an AI tool that helped marketing teams generate social media content with brand-specific voices. They had 400 paying customers, solid retention, and a growing waitlist. On paper, they were winning.

Then ChatGPT’s November 2023 update hit, and within 72 hours, they knew it was over.

His story isn’t unique. It’s becoming the norm.

The Mass Extinction Event Nobody’s Talking About

Let’s be direct: ChatGPT has killed more startups in two years than the 2008 financial crisis killed in four. We just haven’t tallied the bodies yet because many of these companies are dying slowly, in private, behind carefully worded “strategic pivots” and “founder updates.”

The pattern is everywhere once you start looking:

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