There is no issue with this, taking some life pressure off founders is not bad, it lets you focus where you should. Could it upset some early employees, yes it

There is no issue with this, taking some life pressure off founders is not bad, it lets you focus where you should. Could it upset some early employees, yes it could, but I'd argue done properly it won't and done properly anyone who gets upset should raise your eyebrows about why they are there. Two ways to go about this though, one is 100% transparent to the (at least early) employees and tell them exactly what is happening. Second is not to tell them anything about your personal situation as frankly as long as the business is moving forward appropriately and has enough money to reach the next milestones there is no issue. Under the second scenario you only mention the raise going directly to the business as that is all that is relevant to the team. The personal share sale is just that, private and personal. In no way will you be getting wealthy off doing this, you will simply get some living money which you have probably foregone over the past few years, more so than early employees likely. If you do it transparent, I'd present it exactly in the manner above. e.g. "Look, we are taking another X round and as part of the round we are selling a small amount of founders equity to relieve some of our personal life pressures so we can stay 100% focused here". Be honest, you gave up making money to do a startup willingly but that doesn't mean life stopped moving forward and you have bills to pay just like everyone else. Honestly if they can't understand it they may not be there for the right reasons anyway and it will be some insight to the early team members. Early employees might be below market, but likely aren't so far below that they are getting hurt, and if so they'll leave soon enough, rightfully and understandably.