Wait, what?
Wait, what?
I'm not sure if it's common, but it's definitely not unheard of.
Anecdotally from conversations I've had with founders some are very, very keen on cycling options back into the pool as much as possible. More importantly I've heard some ideas on how to do this that made my skin crawl.
I would be interested in hearing these, as I'm sure many others would be as well.
One big takeaway I've had from these conversations is how many founders do not see equity as compensation earned, but as some sort of gift to be granted to the virtuous and loyal.
It's a little depressing that the frank answer to "why not vest quarterly" has been "because if they leave we don't get as many options back". It's interesting that we never think about cash compensation that way but do for equity compensation.