You worked hard for years on startup #1. If you were lucky it didn’t burn to the ground. If you were really lucky, you made money while doing it. And if you were really really lucky you got to keep doing it for a long time before handing it off to someone else.
A smart friend (who happens to be a VC and see a lot of deals) gave me some great advice before I started Spool. He said knowing if you’re ready for another startup is very simple: As soon as you’ve forgotten how painful it is to do a startup, you’re ready to do a startup.
Funny how that works.