[jacquesm]

Another major reason that you won't be able to pick the winner is because you only get to pick once, and then you are booked for a long time. If you think a better one comes along you now have a sunk cost, and you'll be starting all over again, with a very good chance that your 'better' one will end up being worse. So the odds are very much against you if you are evaluating start-ups serially.

The better way to do it is to evaluate a whole pile of them at once, and then to pick the best one that you can find. And you're going to have to do a lot of work to evaluate those options, about as much as though your future depends on it, because it does. If you're not prepared to put in that kind of work then it really is just a lottery, and you're most likely better off to just take a job that pays you roughly what you are worth on the market, in the longer term that + a good savings regime will be a much surer path to some serious cash than buying lottery tickets at an opportunity cost of 300-500K each.