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Scott's Newsletter

You Don't Belong Here (Yet)

The problem isn’t imposter syndrome. The problem is you’re running outdated software.

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Scott D. Clary
Oct 02, 2025
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A friend of mine just closed a $10M Series A.

He’s standing at the investor dinner. Everyone’s celebrating. Someone asks him how it feels to be a “real founder” now.

He laughs. Says something polite. But later, in the car, he tells me: “I still feel like I’m playing dress-up.”

This guy has 40 employees. Millions in revenue. Top-tier VCs fighting to get into his round.

And he still feels like the kid from a small town who barely graduated college.

Here’s what nobody tells you about success: your circumstances change fast. Your identity changes slow.

And that gap between who you are and who you still think you are? It’s either the thing that keeps you hungry, or the thing that keeps you stuck.

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