Evan Armstrong was a lead writer at Every who explored profit and power in technology in Napkin Math.
You Probably Shouldn’t Work at a Startup
It’s overrated—both financially and emotionally
May 20, 2021 · 15 min readUpdated Oct 2, 2026
TL;DR
- This article is for someone trying to decide whether to work at an early-stage, venture-backed startup.
- There is a romantic vision of startup employment that doesn’t hold up under close scrutiny.
- Business model risk is extreme and the financial opportunity cost is significant.
- Typically we assume that a startup is a better overall employment experience, this probably isn’t true for most people
- There are some circumstances where working at a startup makes sense! But it is important to go in with open eyes.
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