Skip to content
You Probably Shouldn’t Work at a Startup

You Probably Shouldn’t Work at a Startup

It’s overrated—both financially and emotionally

Apr 20, 2023 · 17 min readUpdated Sep 10, 2026

Comments1

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.

Create a free account to continue reading

The Only Subscription
You Need to Stay at the
Edge of AI

The essential toolkit for those shaping the future

"This might be the best value you
can get from an AI subscription."

- Jay S.

Every ContentEvery Content
AI&I PodcastAI&I Podcast
MonologueMonologue
Every AgentEvery Agent

Join 100,000+ leaders, builders, and innovators

Community members

Already have an account? Sign in.

What is included in a subscription?

Daily insights from AI pioneers + early access to powerful AI tools

PencilFront-row access to the future of AI
CheckIn-depth reviews of new models on release day
CheckPlaybooks and guides for putting AI to work
CheckPrompts and use cases for builders

Related Essays

Comments

You need to login before you can comment. Don't have an account? Sign up!

We use analytics and advertising tools by default. You can update this anytime.