Cheating, cheating, cheating. That's all I've been hearing for days since Cluely raised $15M from a16z. The news is full of over-baked takes about "academic integrity." People are asking me how we do interviews anymore (they were asking that before too lol).
Look, I get it. The internet is the greatest narrative simplification machine ever built.
Here's the thing: I was playing around with Cluely before it got all hype-y. Not to cheat—I'm way past needing help with homework (though my kids might disagree). I picked it up because I was curious about this whole "proactive AI" thing everyone keeps talking about. What I found wasn't some elaborate cheating scheme—despite the aggressive marketing. It was something way more interesting: a glimpse of what happens when AI stops waiting for permission to help.
And honestly? The whole cheating discourse is missing the point so badly it's almost painful to watch. Everyone is playing into Cluely’s hands and they love to see it guys.
Forgive a little humor, but Cluely is cheating at cheating. They hype the cheating brand to draw in their target IC customers (Gen Z and Gen Alpha). But while everyone's arguing about whether students should use AI for essays (and earning them clicks), Cluely quietly built something that changes how we think about human-AI collaboration entirely. They're not just making another chatbot—they're showing us what Level 2 proactive AI actually looks like in the wild.
I almost didn't write this piece. It felt too... nuanced? Too complex for the current moment where most of the news cycle is dominated by "AI is cheating and we’re all doomed" or (to a lesser extent) “a16z is out to lunch for funding this.” But when I watch a 21-year-old dropout secure venture funding based on a tool that most people completely misunderstand, I realize I at least need to try to articulate what’s going on under the marketing hype and doom-and-gloom.
Here's what I want to dig into:
Why Cluely's $120M valuation makes perfect sense from a startup strategy perspective (even if their AI is pretty mid)
How Cluely helps us think about agentic AI and offers an early picture into where job skills are going next (especially with those juicy B2B contracts they’ve landed)
How their UX innovation reveals where agentic AI is actually heading, and why the cognitive fitness implications are way more profound than anyone's talking about
Plus, if you're building anything in the AI space, understanding what Cluely got right about distribution and timing might be the most important lesson of 2025.
And as a bonus, what we can learn from Cluely’s leaked system prompt. So we’ll get some good prompt analysis in at the end for you prompting geeks!
The real story isn't about cheating. It's about what happens when we stop asking "How can AI help me find the answers?" and start asking and “How can I use proactive AI to extend my thinking?” That shift—from reactive to proactive intelligence—is worth way more than $15 million. And I wrote 31 pages to show you why lol
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