Rapping About Roku: Kirby Grimes on Broken Ad Tech, YouTube TV, and the Death of Display Ads

Kirby Grimes helped build the first streaming TV apps on the planet. He co-founded Float Left, one of Roku's first development partners back in 2009, got acquired, launched 4320 (a B2B marketing agency for media tech companies), and now publishes The Streaming Wars. He also raps about the media industry on LinkedIn and made it to 42 without seeing Star Wars. In this episode of The ADOTAT Show, Pesach Lattin and Kirby get into: 00:00 Intro 01:30 Why ad-supported digital publishing is broken in 2026 06:00 The real reason recipe sites are unusable 10:00 Interruption vs ambient vs task-based attention in advertising 13:00 Contextual ads, dynamic creative, and why none of it works 16:30 Is YouTube TV? The fight nobody is winning 20:00 The Anti-Thought Leader Thought Leader 24:00 Building the Kirby Grimes brand from karaoke to rap singles 31:00 Wall Street is killing the streaming industry 36:00 What media looks like in 2036 40:00 Desert Island Five (no family, includes a therapist) 46:00 Mental health, freezing time, and life as a founder 51:00 Why Kirby went 42 years without watching Star Wars 55:00 Mark Echo, graffiti, and merging the creative and business self 59:00 The cardboard box moment that changed his life 01:03:00 Most overrated and underrated things in streaming 01:07:00 What Kirby wants on the scoreboard in 10 years Sponsored by Troutman Amin LLP, the law firm that speaks fluent ad tech. And by Incremental.com, because attribution shouldn't be a vibe, it should be a number. Subscribe for more conversations with the people actually building, breaking, and rebuilding media, ad tech, and streaming. #Streaming #AdTech #Roku #YouTubeTV #MediaIndustry #DigitalPublishing #ADOTAT #KirbyGrimes #StreamingWars #ContentMarketing