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The $20M Controversy: How Getting Kicked Out of Columbia Led to AI Startup Success

6 min readJul 7, 2025

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Why the most banned founder in tech might be the most important entrepreneur to study

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Most entrepreneurs talk about their Harvard MBA or their prestigious internships. Roy Lee talks about getting kicked out of Columbia University, having his Harvard admission rescinded, and being banned from Amazon for cheating on coding interviews with AI.

At 21, he’s one of the most controversial figures in tech. He’s also one of the most successful.

While other founders struggle to raise seed funding, Roy closed a $15 million Series A in two days. While startups fight for user attention, his company Cluely hit $6 million ARR in just two months. His social media posts generate hundreds of millions of impressions, and his product has become the talk of Silicon Valley.

The story of how he transformed from academia’s biggest failure to venture capital’s newest obsession reveals uncomfortable truths about innovation, authenticity, and what it actually takes to build breakthrough products in the AI era.

The Fall That Became a Foundation

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Aakash Gupta
Aakash Gupta

Written by Aakash Gupta

Helping PMs, product leaders, and product aspirants succeed