I'd be very careful with a 20% option pool and a 3 month cliff. My assumption is this means the founder is providing double the equity, meaning that at 3 month

I'd be very careful with a 20% option pool and a 3 month cliff. My assumption is this means the founder is providing double the equity, meaning that at 3 months the potential of not insignificant amounts of equity can be walking out the door. We've had the experience where we had a contractor who we thought was a good fit. We decided to hire them as an employee, and back-date the cliff to when they started. We had a very big somewhat bet the company deadline which their work was key to, and this deadline was about 3 weeks past the cliff date. They walked 2 weeks before, and didn't deliver. Literally waiting until they could claim some equity. Of course, this is what bad leaver clauses are for, but there is a reason why some of the terms exist. I agree with the long exercise options. Vesting timelines have arguments for longer and shorter, which is why I think the standard 4-years is settled on.