I wouldn't worry too much about trying to estimate a startups chances unless your a domain expert. The more literature you read the more likely it is you'll beg

I wouldn't worry too much about trying to estimate a startups chances unless your a domain expert. The more literature you read the more likely it is you'll begin to be over/under-estimate their chances of success. In my experience the challenge of working in any stage of organisation is fighting its disfunction. If you love your field of work, then this will be likely your only nemesis. A prime benefit of working in a startup is your relative power to do this. So embrace it and use it as a place to learn how to get stuff done. This will serve you well wherever you eventually end up and expose you to people and functions well outside your domain. Given that: 1) Is what they are proposing reasonably sensible? Ask someone normal if unsure :P 2) Is it interesting to you? 3) Do they seem like intelligent, friendly people? 4) Challenge them on a product/architecture decision they have made and see how they respond. 5) Ask how much runway they have and be comfortable with it Finally, you only live once, take a chance, really try to do something new. When your there, speak up. If your lucky you'll have a good experience with good people and learn a hell of a lot.