I think a 5% chance of winning is unrealistic for your math, at least without considering payout. Tie the results to the payout and the expected value should show that working at a start up with the idea of making money via equity is foolish compared to Big Co. Let's take that 1% one and say you get $500k if it works out in an IPO. And let's say you take a salary below market of $30k. It will take the start up 7 to 10 years to IPO. You gave up maybe $300k for the chance at $500k. Or the 5% case where the company exits early and everyone gets $100k. Maybe that takes 3 years. You gave up perhaps $90k for a chance at $100k. You can play start up lottery several times in your career, but equity, unless you are getting a very significant portion, should not be a large factor in choosing the start up you work for. Base salary, the environment, culture, learning opportunities, and the ability to make a difference in an organization are reasons to choose a start up. Just not equity. And that's ok :)