One component in humor is taking an idea out of context. This is in some ways related to "lateral thinking" where you try and brainstorm by randomly changing marketing bits (price, place, promotion, product) to come up with a new way of seeing things. I think some people with a creative/entrepreneurial mindset automate this process in their heads. So you could see humor as a similar creative process to that of some innovators: being able to see the world in a slightly different/skewed way. In one case, it makes you laugh because of the incongruity, in another, it may help you see ideas for businesses where others do not see them.
More generally, I would tend to say that humor is often about finding odd connections. I can easily imagine that being an important ability for giving good advice to businesses.
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.
