[brandur]

The company isn't compelled in any way to allow this though, and is actually disincentivized from doing so because it increases the probability of key departures as those people are able to extract some value.

If you're in such a position, you better hope that your founders _really_ like you.

[bogomipz]

I believe most do though, but with a right of first refusal. In which case they will buy them of direct you to their preferred buyer. Source: I have done this and my conversation with the broker for the secondary market who handles a lot of this said it is quite common and that in fact other at the same company I was at had done so. It might be frowned upon internally but you have to look out for yourself. Staying at a startup for 8+ plus years isn't very realistic for me personally.

[amenghra]

Many companies have periods of time where you get an opportunity to cash out a percentage of your equity. It gives confidence to early employees that the company has their back and they aren't really disincentivized to leave because they still have a majority of their equity "locked".