This is only acceptable if your company is very successful and it is clear you have made a lot of value for your team and your investors. If the success isn’t t

This is only acceptable if your company is very successful and it is clear you have made a lot of value for your team and your investors. If the success isn’t there, it will cause lots of problems. If you take money off the table when everyone else’s success is still in question, you’ll lose the trust of your team. A founder selling 5% of their stock could be a lot of $, but 5% of employee #2s is likely much less so the impact of their participation is much less.