John Whitmore reflects on the evolution of the ad tech industry, drawing parallels between the early 2000s boom-bust era and the shifts leading up to the programmatic age. He traces the journey from pre-programmatic media and DoubleClick Exchange to the present, where the industry is grappling with challenges like signal loss, AI, and privacy concerns. Whitmore emphasizes that while this new phase feels both familiar and different, it brings an exciting and transformative future for digital media and ad tech.