Jesters were important in monarchies because they could speak truth to power. I think there's a similar idea here: you have to be very headstrong to do a start

Jesters were important in monarchies because they could speak truth to power. I think there's a similar idea here: you have to be very headstrong to do a startup, but at times you also need to pull yourself out of that and really consider other angles/viewpoints. If you can couch advice sometimes in humor, maybe it can be an effective way of getting through to a founder who would otherwise have a hard time hearing it.