Current job: about four months between starting the funding round and checks clearing. That was quick, as far as I understand. Last job: it never happened and

Current job: about four months between starting the funding round and checks clearing. That was quick, as far as I understand. Last job: it never happened and we ran out of runway. Similar story to yours - cagey founders who didn't want to promise anything but always remained optimistic. A deal kept getting pushed and pushed, and eventually everyone lost their jobs. Tbqh the biggest lesson was that lack of transparency means that things are bad. Just ask specifics, like what the current runway is, have the founders forgone salary to extend it, did they receive a term sheet, who are the partners that they're speaking with at which VCs, etc. They should have exact answers to those questions. My advice from being a serial early employee is to start looking for a job the second you don't have faith in the founders to execute. It will usually take you longer to find the next gig than you will get in severance if everything goes to hell. It doesn't hurt to be on the job hunt.