This $20M AI Founder Is Challenging Elon and Sam Altman | Roy Lee, Cluely

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Jul 6, 2025

Roy Lee, founder of Cluely, a trailblazing AI startup, shares his audacious journey from getting expelled from Ivy League schools to building a $6M ARR business. He reveals how controversy can drive growth, discussing his viral marketing tactics and unconventional fundraising strategies. Roy highlights the importance of user behavior over traditional rules in product design and engages in a lively comparison with industry giants like Elon Musk and Sam Altman. His insights on the impact of AI in today’s marketplace are both thought-provoking and entertaining.

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ANECDOTE

Roy's Provocative School Exit

Roy Lee was kicked out of Harvard and Columbia due to his provocative behavior and being polarizing.
These setbacks motivated him to channel his energy into building a bold company instead of traditional schooling.

INSIGHT

Mastering Short-Form Virality

Short-form content algorithms reward digestible, controversial material that forces opinions.
Many tech founders fail to grasp this viral formula and produce overly complex, less engaging content.

ADVICE

Create Digestible, Reactionable Content

Create content that is both understandable by everyone and provokes reactions.
If no one would quote-post your content virally, revise it for better engagement potential.

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Amazon banned him. Ivy Leagues kicked him out.

And still, he went mega viral, built a $6M ARR AI startup, and raised $15M from a16z… all in a matter of weeks.

This might be the craziest founder story you’ll hear all year.

If you’re building in a competitive market, struggling to stand out, or just want to learn how to blend controversy with growth, this one’s for you.

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Timestamps:

21yo Worth $100M+ - 0:00

Harvard Kicked Me Out - 3:02

Tech Twitter Main Character - 4:33

Ads - 6:44

Controversial = Views Formula - 8:26

Stripper Commercial Brainstorms - 12:47

Liquid Glass Before Apple - 16:55

User Feedback Drives Product - 19:48

Sales Tech & Enterprise - 23:16

Cheating in Meetings - 27:19

Ad - 28:22

How to Fundraise Like Roy - 29:28

Brain Chips End Game - 31:05

Roy vs Elon vs Sam - 33:12

Frat House Culture - 34:44

The Cluely Internship - 37:37

Are We Getting Dumber? - 38:51

Roy Going to Jail? - 40:44

Thanks for Watching - 42:18

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Key Takeaways:

1. Don’t wait for permission. He got kicked out of two top schools and used that energy to build something the world couldn’t ignore. If the system doesn’t reward you, build outside it.

2. Design for real behavior, not rules. Interview Coder wasn’t legal or polite, it was effective. It gave users AI help without getting caught. Start with what people actually want.

3. Rethink how AI should show up. Stop building chatbots. Build experiences where AI quietly blends into the workflow. Think overlays, not windows. Think invisible, not interruptive.

4. Your product doesn’t need to sound safe. “Cheat on everything” wasn’t just a headline, it was a magnet for attention. Don’t fear being bold if it reflects what your product actually does.

5. You don’t need a pitch deck if the story tells itself. Cluely raised $15M without running a process. When the traction is undeniable and your product is everywhere, investors come to you.

6. Build virality into your operating system. Don’t “hope” something goes viral. Study what’s working. Run daily idea sessions. Create with the expectation that every post could hit 100M views.

7. Make your content pass two filters or kill it. Can anyone understand it instantly? Will people feel something strong enough to react? If not, it won’t break through. Keep it simple and emotional.

8. Ignore vanity metrics, chase visibility. Don’t waste time measuring click-through rates on content that won’t work next week. Stay focused on showing up everywhere your user lives.

9. You don’t need a big team to move fast. Cluely runs on 4 engineers. No designers. No PMs. Still they've $6M ARR. If you can ship fast and learn faster, you’re already ahead.

10. Build a product that feels inevitable. This isn’t just for sales teams. Cluely is betting on a world where AI support shows up before you even ask for it. Design for that future now.

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Related Podcasts:

Bolt CEO and Founder on How he Hit $30M ARR in a Year

LogRocket CEO and Founder on How to Build a $100M+ AI Startup

Amplitude CEO and Founder on Building the Product Analytics Leader

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