Before “programmatic” was a word, Bob Regular was already in the trenches of digital advertising. Today, as CEO of Infolinks Media, he’s seen enough hype cycles to know that progress takes patience and a sense of humor.

We talked about the rise and fall of the dot-com bubble, the long road from cookies to context, and the strange reality that AI may make media buying both smarter and more commoditized. Bob also shared a sharp view on regulation, calling out how well-intentioned privacy laws ended up suffocating smaller publishers while barely protecting users.

If you’ve ever wondered how