Asking for a friend…
An angel investor in a successful startup wants to cash out a bit in a secondary but the founders are telling him he can only cash out fully or stay in full. No partial sale allowed. But his shareholder docs show he has tag along rights to the tune of 20%. Would it rub off a founder the wrong way if the angel were to invoke that right? Presumably because the founder may then have to offer a partial sale to all exiting shareholders, some of whom may not have been aware of their tag along rights.
It’s interesting the founder drew such a firm line there. Presumably the founder should know what they agreed to, and that the tag along request is legitimate.
It’s important to have respect on both sides of a business relationship. Sure, the angel investor could back down to keep the founder happy, but is that a good long-term dynamic? At best, the investor might remind the founder about their agreement and ask why the founder is hoping to avoid any investor sales. Maybe some middle ground can be reached, eg stealth tag along if that’s a thing.