Is it time to quit your job at a unicorn?

by Dalton Caldwell10/19/2023

Dalton Caldwell and Michael Seibel talking; behind them, a unicorn sits at an office desk

If you’re an employee of a late-stage company right now, how would you know when it’s time to move on vs. time to double down?

It’s an especially pertinent question today; the late stage funding market is… slow and the IPO window is still effectively closed. Is this a good time for employees to consider working for a smaller/earlier stage company?

The fact is that there isn't an easy answer — it can really vary from person to person, and situation to situation. In this episode of Dalton + Michael, Michael and I share some suggestions on what sort of things an employee of a late-stage startup should be looking for — the good signs and the bad — to best make this decision.


  • Dalton Caldwell

    Dalton is Managing Director, Architect and Group Partner at YC. He was the cofounder and CEO of imeem (acquired by MySpace in 2009), and the cofounder and CEO of