The internet made content abundant. It also made monetization harder than ever.
After selling his digital agency to WPP, Trevor Kaufman became convinced that journalism’s biggest problem wasn’t audience demand, but the mechanics of turning engagement into sustainable revenue. That led him to found Tinypass, which later evolved into Piano—software that helps organizations decide when to ask users to pay, what to offer, and how to tailor those decisions based on real behavior.
At the center of Piano is a behavioral data layer that tracks and responds to how users actually interact with content. Subscriptions, messaging, analytics, and personalization all run through a single platform, replacing the fragmented tools many organizations use to manage customer experiences. What started in media has since extended into banking, retail, and airlines, with customers including the BBC, The Wall Street Journal, CBS, and LinkedIn.
In this episode, Kaufman explains why the web’s anonymity still complicates digital business models, how Piano scaled through a series of disciplined acquisitions, and how the company is using AI to automate analysis and operational decisions across its platform.