If the red flag is related to the founder leaving over a disagreement related to strategy, it sounds like it should be a red flag and be considered by an invest

If the red flag is related to the founder leaving over a disagreement related to strategy, it sounds like it should be a red flag and be considered by an investor. Even ignoring the cap table issues making it harder to incentivize future employees. Assuming that they're taking the high road and that the potential investor is well aware that a founder is leaving over a disagreement regarding strategy, which I sure hope they are, the investor is walking in with eyes open and is making a bet that the person leaving is incorrect. That seems to me to be perfectly reasonable. If you want to be generous (as the person leaving) you can certainly offer to let the investor or co-founders buy you out at the same valuation the investor is getting. If you want to be extremely generous and a little creative, you can ask for an amount of money that would make you feel you hadn't been cheated in exchange for all of your equity stake. After all, you disagree with their strategy, so perhaps you are skeptical that the equity is worth anything and would rather just get decent back-wages for the work you've done and wash your hands of it. In that case, perhaps you can just ask for something like $200k for all of it and call it a day. If I disagreed enough with the company direction to leave, I might call that a huge win relative to putting in years more effort and eventually getting nothing at all out of it!