Another lesson from the great Kevin Pollak. One of the points he makes about acting is that many novices make the mistake of playing to the crew. When you're on the set of a movie, there is no studio audience. The closest thing are the members of the crew--all the gaffers, grips, and best boys whose names you see at the end of the movie credits, but whom you have no idea what they actually do.
In a similar way, when you're working on your startup, most of the people you interact with are "crew"--your colleagues, investors, advisors, and so on.
What both crews have in common is that they aren't even remotely like the intended audience. A film crew consists of seasoned pros who have seen it all; the things they find funny tend to be highly original and edgy--broader, less transgressive comedy falls flat because it is too familiar.
You startup crew installs new apps on a daily basis, and is used to firing up tools to check source code and event logs. The things that impress them are meaningless to the real audience, and vice versa.
As you build your products, you need to play to the audience, not the crew. To do this, the members of your product and engineering team need regular exposure to real users and customers. In the film world, this means test screenings; in the startup world, this means bringing in outsiders to use your product and interact with your people.