
You Probably Shouldn’t Work at a Startup
It’s overrated—both financially and emotionally
Apr 20, 2023 · 17 min readUpdated Jul 16, 2026
Sponsored By: Divvy
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This week I am a slug whose body is a fusion of cough drops, tissues, and NyQuil. (i.e. I am very sick). As such, please enjoy a republish of one my spiciest takes.
After this came out, I had a couple of founders message me that startups are different now and are just as safe as big tech companies. This morning I checked in on those people to see how things were going. Their startups no longer exist...you probably shouldn't work at a startup.
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.
Thanks to our Sponsor: Divvy
Thanks again to our sponsor Divvy. Experience the future of expense management, and save up to 300 hours annually. Join us for a demo this month and receive a $100 Amazon gift card as a bonus.
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