My gut feeling here is that the founder has an outsized perception of the value of the potentially-vested shares.
95% of startup shares are pointless funny money. The remaining 5% that turn into something only really make wealth for the founders and the VCs. Having been through acquisition a couple times and seen how it shakes out for individual contributors -- most employees could make more money in a year or two of regular FAANG compensation.
I know those shares look super important to the founders, and founders need to believe in their business to stay motivated. But the share agreements for startups these days rarely provide more than a small fraction of a percent to an employee, and even fairly generous exits lead to "helps with downpayment for house" level money, not "retire in the south of France" or "go start my own startup now" level money. https://www.tldroptions.io/ is informative here.
Those of us who are working in startups as employees don't do so on the hope of getting rich -- we do so because the work is sometimes interesting. In competitive job markets, founders need to keep this in mind. For non-junior employees -- or anybody who has been around the block -- the equity is rarely the thing keeping them there. The work environment and project is.
All this to say, focusing on the vesting seems silly. Those shares are likely useless and not worth getting stressed about. Unless this person was offered a substantial equity stake, it's the wrong thing to focus on.
Fix your performance management process and move on. Playing games with the equity now is only going to make you look petty.
That is what it strikes me as. But even large companies can play this game. One I worked at had a fairly sweet pension plan. The catch was you had to work there 30 years. It was pointed out to me when I had been there about 2 years that at about 29.5 they would let someone go then re-hire as contractor. It was usually 2-3 people in the building I worked in, per year, and was for them considered a small facility of 'only' 200 people. In the time I was there only one guy made it to 30 and he was an upper manager. My takeaway on that was take care of yourself and your money. Do not depend on 'bonus' items like that.
95% of startup shares are pointless funny money. The remaining 5% that turn into something only really make wealth for the founders and the VCs. Having been through acquisition a couple times and seen how it shakes out for individual contributors -- most employees could make more money in a year or two of regular FAANG compensation.
I know those shares look super important to the founders, and founders need to believe in their business to stay motivated. But the share agreements for startups these days rarely provide more than a small fraction of a percent to an employee, and even fairly generous exits lead to "helps with downpayment for house" level money, not "retire in the south of France" or "go start my own startup now" level money. https://www.tldroptions.io/ is informative here.
Those of us who are working in startups as employees don't do so on the hope of getting rich -- we do so because the work is sometimes interesting. In competitive job markets, founders need to keep this in mind. For non-junior employees -- or anybody who has been around the block -- the equity is rarely the thing keeping them there. The work environment and project is.
All this to say, focusing on the vesting seems silly. Those shares are likely useless and not worth getting stressed about. Unless this person was offered a substantial equity stake, it's the wrong thing to focus on.
Fix your performance management process and move on. Playing games with the equity now is only going to make you look petty.