If these are privately held companies, there really is no way for you to evaluate them, all the info is private. Really your best bet to gather info comes in the interview process and spending time with a finance type person. However, understand, they may not be telling the truth. Your hire might be a last ditch effort, of the board/investors, to salvage the company. An example of this is a software company, that suffers with code quality, hiring a bunch of testers to improve the quality of their products. If the culture does not support code quality, then the company may just crash and burn. So even your hire may not be an indication of company stability/strength. A red flag for me, given the numbers you cite, is the generosity of the grants. 40k shares at such a low strike is crazily generous. It is almost if they do not expect either company to amount to much. It even shows a bit of poor management decisions. One can be issued the grant, wait until some or all of the grant vests, then just purchase the options and move onto another business. Options grant such as these are typically used to encourage employees to work long and hard to make the company profitable and to stay with the company. This is typically done with higher strike prices and subsequent grants. These grant offering are encouraging employees to take the job, and move on in a relatively short time. Without a lot of other information, I would say that either of these grants will probably be worth nothing. Take one of the jobs if you need it, but you may want to keep looking.