From the earliest movement of computers into classrooms and school administrative offices, there have been companies and individuals at the heads of those companies, who have been looking for ways to use software applications to make teaching and learning easier. There is no doubt that many of these companies were driven by the entrepreneurial spirit. There was huge money to be made in the educational marketplace. But there were also insightful individuals who knew enough to find areas of education where technology could find a niche and be useful not just for the business but also for teaching and learning. I explore several of these companies and their products in light of what we now know about the pandemic and how online learning has driven the marketplace for technological solutions to the administrative problems of teachers and schools and school jurisdictions.