It's now more than twenty years since digital media began its insurgency, revolutionizing not only marketing to consumers and businesses, but transforming the operations, the economics and the expectations of all previously existing media. An ocean of ink has been spilled trying to explain this explosive phenomenon, but I think it comes down to a simple set of promises made by digital media from the very beginning: 1) a promise to the consumer to make information, experiences and things available when and where they are wanted; 2) a promise to the marketer to connect with the consumer at the most relevant times and places, and 3) a promise of concrete behavioral and intentional data signals to connect the consumer and the marketer deeply and interactively. These new promises were perceived, even if hazily, by a group of perceptive and creative pioneers in the new medium, and their persistence and passionate advocacy, and the concurrent invention of new technological hardware, software and processes, built the digital media ecosystem that we take for granted today.