After receiving a job offer from a startup, what is a quick way to evaluate whether your options will eventually make you at least a million dollars?

There are lot of factors to consider, like will the company issue more shares in the future (thereby diluting your existing shares).  But assuming they don't, then here's how you can answer your question.  For 5000 shares to be worth a million dollars (before taxes), the shares have to be worth $200 each.  (5000 * $200 = $1 million).  To make any kind of educated guess as the what the shares each might be worth someday, you need to know how many outstanding shares there are.  You'll have to ask the company how many outstanding shares there are.  (If they won't answer, this as a warning sign, but that's another issue). Let's assume for example that you find out the company has 10 million shares.  Then for each share to be worth $200, the company will have to be valued at $200 * 10,000,000, or $2 billion.  So then your question is, can the company become worth $2 billion. On the other hand, if the company only has 1 million shares outstanding (instead of 10 million), then the company "only" has to be worth $200 million to reach the $200 per share price.  ($200 * 1,000,000 = $200,000,000). Also in this example, I've ignored your salary.  If you have an average salary of $80,000 per year over 4 years, there's $320,000 (before taxes) toward your 1 million dollars.

You don't tell us what those shares represent so it's hard to help. The number/value of shares without the global number are useless. The real question is what valuation exit can you expect and that, only you can tell. Is the business promising ? Are the founders reliable ? Is there real value added created week after week ? These are the real questions you should focus on.