You Probably Shouldn’t Work at a Startup

2 min read Original article ↗
You Probably Shouldn’t Work at a Startup

It’s overrated—both financially and emotionally

Apr 20, 2023Updated May 21, 2026

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This essay is brought to you by 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.

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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