You are thinking in terms of positive outcomes, although a failure is much more likely. When you join a startup for a typical early stage employee equity (2% o

You are thinking in terms of positive outcomes, although a failure is much more likely. When you join a startup for a typical early stage employee equity (2% or less), never put any monetary value for shares. It's likely worth is 0 and even in the case of a small acquisition, the amount you earn doesn't change your life in a big way (I was an employee in a founding team of a startup that was acqui-hired by Google) - you can earn similar amounts in a more straight-forward way as a hardworking consultant. All the other positive acquisition outcomes are such outliers that it doesn't make sense to estimate their likelihood. That said, you can learn a lot about running a startup by joining one, and it's a good chance to build a good network of people. Raising angel money, getting advisors etc. will be easier if you already are known in your local startup scene. Also, although I encourage people to start their own companies, it's much harder than you think. It's more fulfilling than being an employee, but it's hard. I'm currently running a "failed" bootstrapped startup, that we had to changed in to a consulting house and planning what to do next.