For a privately held company the number of shares outstanding, on its own, isn’t enough and really doesn’t tell you much. Your shares are almost certainly not the same as other people’s shares and you need to know what those differences are. Other people likely hold shares that have terms like “I get paid 3X my investment before anyone else gets paid.” Or other terms that make the total number of shares not that informative in knowing where you really stand. If someone’s not sitting down with you and laying everything out on the table then it’s almost certain there are things they don’t want you to know that make your offer significantly less attractive than what it might appear in face value.

You can ask about liquidation preferences as well. Anything above 1X is above market and, again, a red flag.

Is there a list of these red flags to watch out for or ask about for startups?