The Digester

Cluely and Roy Lee expose Silicon Valley's AI divide

Feb 22nd 2026

A viral AI tool that helps people cheat in interviews and on the job turned its founder into a flashpoint, driving public backlash in San Francisco and spotlighting a tech-era split between an 'agentic' overclass and those likely to be displaced by AI.

  • Cluely is a glitchy AI interface built to answer questions in real time and assist users in interviews, meetings, and everyday office tasks.
  • Founder Chungin "Roy" Lee rose to fame after posting videos of using the tool, dropped out of Columbia, and raised tens of millions in venture capital.
  • The company cultivated a fratty startup culture while its product repeatedly failed in demonstrations and drew widespread public contempt.
  • San Francisco regulators effectively pushed Cluely out of the city after its controversial ads and aggressive marketing provoked local backlash.
  • Cluely is seen as a concrete example of a Silicon Valley doctrine that rewards high agency and risks creating a stark economic bifurcation as AI automates cognitive work.
  • Critics argue the product normalizes outsourcing thinking and raises privacy and ethical concerns even as many tech workers already rely on AI for routine tasks.

Sources

harpers.org