Show Me the Money
How WordPress.com made money was a question I was often asked when I spoke at events. The very popularity of WordPress made these explanations complicated. The distinction among the three entities of WordPress (the open source project), WordPress.com (one use of WordPress), and Automattic, Inc. (the company behind WordPress.com) caused constant confusion. Well-known brands are monolithic: Disney is Disney, Coke is Coke. They rarely divide their intellectual property or agenda into externally visible factions (they keep the joys of infighting inside if they can). The price of the WordPress project's independence from any corporation was a public relations challenge WordPress.com would continually face.