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Hey readers,

A 21-year-old gets kicked out of Columbia University.

Six months later, Andreessen Horowitz wrote him a $15M check.

Sound familiar?

Think Zuckerberg, but with a twist that'll make you question everything about "playing fair."

Curious? So was I.

If you’re wondering, we’re talking about Cluely.

Before we talk about this gentleman, have a look at what’s cooking in the AI World.

Curated Chaos

1. Need the latest AI productivity tools? Grab this list

2. Gemini 2.5 Pro is back in the free tier of the API. Verify here

3. Veo 3 launched in India. Read more here

4. Microsoft is laying off 9,000 folks because of AI this year. Is this the beginning of the end? Read more here

5. Want to learn how to make money using AI? Check my podcast here

6. Also… Grammarly acquired Superhuman. I really never bothered with grammar in most of my emails, but I guess now all emails will be perfect?

It’s 2024

Roy Lee (founder of Cluely) was dying inside.

600 hours of LeetCode grinding.

Another 3 AM all-nighter memorizing algorithms he'd never use.

The kid who once loved building things was now a zombie in the tech interview machine. Until he snapped.

Four days later: Interview Coder was born.

This was a real-time, screenshot-taking, solution-feeding interview destroyer powered by AI.

But instead of being subtle and hiding it.

He used Interview Coder during an actual Amazon interview. Recorded the entire session. Posted it on YouTube for the world to see.

The video was digital vandalism disguised as a product demo. Roy was publicly executing the entire technical interview process.

Amazon offered him the job anyway.

Plot twist?

Someone at Amazon snitched to Columbia. Roy got suspended.

Most students would've deleted their social media and transferred schools.

Roy chose to leak the disciplinary documents and turned his academic death sentence into creating distribution through virality.

The result? 10 million views and a complete narrative flip.

Overnight, Roy went from being the villain who "cheated" to the hero who exposed a broken system.

The conversation shifted from "Roy is a cheater" to "Why are technical interviews so broken that AI can game them?"

Roy had accidentally discovered Silicon Valley's most powerful growth engine: Controlled controversy.

Fast forward March 2025.

Roy's phone won't stop buzzing.

VCs sliding into his DMs.

Interview Coder hit $170K monthly revenue with 50% week-over-week growth.

But Roy didn’t want to be known as the company that ‘helps kids cheat’ forever.

So instead of just selling to students, he asked what could be sold to everyone else?

April 2025. Interview Coder dies.
Cluely is born.

Same technology. Completely different story.

Instead of "cheat on coding interviews," it's now "real-time AI assistance for professionals."

Roy's not targeting broke college kids anymore.
He's going after enterprises with million-dollar budgets.

The rebrand video drops.
Roy uses Cluely to fake art knowledge on a fancy restaurant date.
The internet explodes. "Dystopian!" "Black Mirror!" Critics lose their minds.

Roy's realization: Controversy creates cash.

He was right:

June 2025: Roy raises $15M Series A at a $120M valuation.

The expelled student was now worth more than most of his Columbia professors' lifetime earnings.

Andreessen Horowitz led the round. The same VC firm that backed Facebook, Airbnb, and Stripe was betting big on the kid who got kicked out of school for "cheating."

But here's what the TechCrunch headlines missed: This wasn't just about one controversial founder. This was about a fundamental shift in how enterprises think about AI assistance.

My thoughts:

Roy proved that AI adoption is more about competitive advantage over ethics.

While we debate whether AI assistance is "fair," enterprises are quietly implementing it everywhere. Sales teams, customer support, technical interviews, legal research.

The companies that figure out AI enhancement first will dominate their categories. The ones that don't will become irrelevant.

Sometimes the best way to win the game is to break it first.

Hit reply and tell me: What's the most controversial business decision you've made that ended up being brilliant (or disastrous)?

The best response gets a shoutout in next week's edition.

Until next time,
Vaibhav

PS: If you read till here, you might find this interesting

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