Let's first of all recognize that if you could pick likely winners (especially with limited financial and business info) you would be an all-star VC and not an

Let's first of all recognize that if you could pick likely winners (especially with limited financial and business info) you would be an all-star VC and not an employee. It isn't something you should even think about because you will never have enough info to judge accurately. What you CAN do is figure out what stage the business is in. Are they pursuing series A funding? Series B? Looking to be acquired? Minting money? Are they growing staff and offices as fast as possible? That could be good or bad. Companies that grow suddenly end suddenly, too. How much runway does the company have? You can probably get away with asking this. What you probably want to hear is "we are self-sufficient and growing", what you will probably hear is "we have a vaguely long runway". What you don't want to hear is "don't worry about it" or "I have no idea". Healthy businesses have an idea. Startups should want people who are invested in growing the whole business, not just employees and they should like that you ask (otherwise, you are accepting risk for no day-to-day benefit. Stock options aren't the real benefit. Working a job where you can more fully contribute is the real perk). Last, do you like and understand the product? If not, is the team awesome and has much to teach you? If not, don't join, no matter how shiny they make the future sound.