[cs-szazz]

It's talked about a little, but there's two classes of shares (common and preferred). Usually startups will value your options in an offer using preferred, so they might say you have 100k options at a $1 value each, with a 5 cent strike. But the reality is even if you manage to get liquidity, perhaps through a secondary, you probably won't be able to sell at the preferred price! If you wait until IPO then common equals preferred and it doesn't matter, but it always felt wrong that the value of your options was only true if the company IPOs, versus taking in to account an appropriate discount.

[antognini]

What is a typical discount for common vs. preferred shares? I'm sure it's pretty dependent on the specifics of the company, but I've found it hard to even get a range of values.

[cs-szazz]

It depends on how far along the company is, as IPO approaches it'll be a 0% discount. For a Series C-D, 60-70% discount isn't uncommon.