I think asking for a rough estimate of runway is totally reasonable. Just don't expect them to tell you how much cash they have on hand or to get an exact time

I think asking for a rough estimate of runway is totally reasonable. Just don't expect them to tell you how much cash they have on hand or to get an exact timeline. But expecting something like "one month," "six months but we are talking about ways to increase that," "one year," or ""one year+" seem like reasonable responses to me if they expect you to take a leap of faith joining them. Are you seeking new investment is a reasonable question, but it could reasonably not be answered, I think. Why you think the product will succeed is a question I can't imagine not asking. What's the end game is a great question. If you are joining a startup, you need to know the end game so you can properly value your compensation. If you know about a problem, you absolutely should ask how they plan to address it. Again, this could reasonably not be answered with too much detail on the startups end (you'll likely get the kind of answer a reporter would). The answer or lack thereof are all very valuable pieces of information, and no company I would like to work for would hold me asking them against them (so long as I respect their wishes in terms of what is actually shared).