@harj - How do you feel about granting cash bonuses to employees at pre-determined intervals to cover the tax cost of exercising their options? It seems like t

@harj - How do you feel about granting cash bonuses to employees at pre-determined intervals to cover the tax cost of exercising their options? It seems like that would solve a lot of these issues, but also give the employee the flexibility to keep a small amount of cash if they'd prefer that over the risk of owning stock. An example: I join a $5,000,000 Series A startup with a 1% equity grant that vests evenly over four years. At the end of each year, I get a $5000 bonus for the purpose of paying taxes on exercised options. It's a bit more than the tax cost for the first year, and likely a bit less in the later years, but after 4 years I've been given $20,000 which should be enough to cover most of the tax burden. If I leave at the end, I still have a 90 day window to exercise them and the money in the bank to do so. I could just keep the cash, exercise them at the end, or exercise them for a cheaper cost each year. That doesn't seem too unreasonable for post Series-A startups cost wise. An extra 5k a year is nothing compared to the cost of a developer overall.