Craigslist: The Anti-AI Internet Haven Where Anonymity and Community Still Work

In an era of AI-driven algorithmic gentrification, Craigslist remains a digital relic where anonymity and chaos thrive—without a single neural network to track you.

Megan Koester describes the platform’s raw energy:

"The real freaks come out on Craigslist. There's a purity to it."

For three decades, co-founders Craig Newmark and Jim Buckmaster have resisted AI-driven platforms, maintaining a system without algorithms, ratings, or user tracking. The site generates revenue through modest $50 listing fees, yet it remains the 40th most popular website in the U.S. with 105 million monthly users.

The site "random factor" has led to unique outcomes. Koester built a Mojave Desert home from free listings, while Toledo, Ohio, employers have hired "people who almost have nothing to lose." Unlike Depop or TikTok, which use algorithmic curation to shape user experiences, Craigslist’s manual ad posting system rejects what it calls algorithmic "gentrification."

Jessa Lingel questions the industry’s data-driven obsession:

"Why do all these web 2.0 companies insist the only way to succeed is off the back of user data?"

The platform’s "missed connections" section exemplifies its user autonomy model—unlike AI-filtered dating apps, it relies on raw, uncurated social dynamics.