This is especially true in the ed-tech startup world. Many entrepreneurs are creating applications for teachers without ever speaking to a teacher or school administrator. They have experience with receiving education and self-education, but they don't know how teachers use technology.

Teachers and administrators have to manage multiple learning styles in a classroom of ~20 kids, and what works for the kid who will grow up to be an entrepreneur doesn't always work for the kid who will grow up to be a historian or accountant. As such, the initial abstraction of projecting our own educational experiences onto entire classrooms generally ends up flopping.