#96 From Startups to Streaming: Kevin Weatherman’s Playbook for AI-Driven Growth

In this episode of Always Be Testing, host Tye DeGrange sits down with Kevin Weatherman, co-founder of Upscale AI, a performance streaming platform using AI to power connected TV ads for DTC brands. With a rich background that includes being the first business hire at multiple startups, angel investing, and co-founding a global run club, Kevin shares his journey from selling limo rides to Google employees to scaling AI-driven advertising solutions. Their conversation covers Kevin’s approach to identifying market trends, the evolution of A/B testing, connected TV measurement strategies, AI in creative production, the intersection of brand and performance marketing, influencer and affiliate strategies, hiring in the AI era, and personal insights from his journey to sobriety.