For small companies, it's very reasonable to ask, at minimum, their runway. There's a big difference between 3 months and 18 months, and this is very relevant

For small companies, it's very reasonable to ask, at minimum, their runway. There's a big difference between 3 months and 18 months, and this is very relevant to your decision, particularly if you're currently employed. If the runway is less than 6 months, it's reasonable to tell them to complete the raise and email you when they're done. A friend of mine was laid off less than 4 months after a startup talked him into leaving apple because they didn't get their raise done. I'd also ask when they're going to raise their next round on -- what features / milestones / usage / whatever get the raise done in the ceo's mind. And where they are on getting the aforementioned accomplished. I would prefer the ceo to know this off the top of his or her head.