In this episode of The Bear Roars, Dan Caruso sits down with Tony Fagan—CEO of VideoAMP and one of the sharpest technical operators rebuilding a software company through the AI platform shift—for a wide-ranging conversation about building YouTube's ad business at Google, leading an established company through full-stack AI transformation, and the personal moment Claude started to out-reason him on a topic he thought he knew well.
Tony breaks down the 15-year chapter at Google that taught him how to build software at scale. He led the data science and machine learning teams behind YouTube's advertising business, where the central sales problem was getting brand advertisers used to TV ads—predictable pricing, bulk discounts, unskippable spots—to buy auction-based, skippable digital ads. The breakthrough came from measurement: across 100,000+ campaigns, moving even 1% of a TV budget to YouTube could lift overall reach by 5–15% at the same spend. "Better together" became the pitch that finally unlocked brand budgets and helped quietly build YouTube into one of the largest ad businesses on the internet.
Dan and Tony dig into the full scope of what VideoAMP has become: a streaming-data and measurement platform that unifies what households watch, what ads they're exposed to, and what actions they take—across YouTube, Amazon, Netflix, Disney, Paramount+, Meta, and on—around a single mission: helping advertisers actually measure and guarantee outcomes at scale. In four years the company has flipped from 95% services to 95% software, and is now one of the most technical operators in ad-tech, with roughly 360 employees and a tech stack being rebuilt in real time.
The conversation takes a sharp turn into AI—and this is where it gets fascinating. Tony shares how he's rebuilding the hardest parts of the tech stack from scratch with six people and AI agents writing all the code, cutting compute costs to roughly 20%, and standing up custom LoRA-adapted models on their own hardware for specialized tasks like writing Rust and SQL. He talks about the "cowboy-coders" moment that taught him changing engineering culture isn't easy, how multi-agent workflows are quietly absorbing the institutional-knowledge work of middle management, and the personal turning point when Claude actually out-reasoned him on something he thought he knew. As Tony puts it: that's the moment you stop iterating and say, "wait, I'm not thinking big enough. I'm going to change everything."
Learn more about VideoAMP: https://videoamp.com/
Order Dan's Book – Bandwidth: The Untold Story of Ambition, Deception, and Innovation that Shaped the Internet Age and Dot-Com Boom: dan-caruso.com/book
Listen to Dan's Song Stretch: https://distrokid.com/hyperfollow/dancaruso/stretch
Check out music by Jason Mendelson (Jace Allen): /@jaceallen
To nominate a founder or yourself as a future guest speaker, email: contact@loudbearproductions.com