Under The Hoodie

Episode 11: The AI Sandbox Problem

Bill and Kurtis dig into the growing illusion of “easy AI.” After experimenting with building an app using Claude, Bill runs headfirst into the limits of what these tools can actually do. Paired with the shutdown of Sora, the episode explores a bigger question: are we building the future, or just playing in a very convincing sandbox?

Episode 10: We’re Not Even Past the National Anthem: AI’s Real Starting Line

In this episode of Under The Hoodie, Kurtis is joined by Joseph Wibe for a wide-ranging and unexpectedly deep conversation on where AI is actually taking us, and whether we’re ready for it. They explore the idea that we’re living through an “interregnum,” a transitional moment between economic systems, ways of working, and even definitions of human purpose. From agentic AI and commoditized workflows to universal basic income, robotics in the home, and the future of work, the conversation moves quickly between optimism and unease.

Episode 9: Surprise Guest Matt Fowler on Agentic AI and MLS Innovation

In Episode 9 of Under the Hoodie, Bill and Kurtis reconnect after Kurtis’s trip to Spain and jump into a big conversation about agentic AI, what it promises, what it actually delivers today, and why that gap matters. Along the way, they explore the real difference between AI that advises and AI that truly executes. Then the episode takes a turn with a surprise guest appearance from Matt Fowler, CEO of Doorify, who joins the conversation to share how his team is using AI, MCP tools, and deep data access to build practical innovation inside the MLS. The episode covers everything from vacation planning and whiskey tours to listing performance, broker value, and the bigger future of AI in real estate.

Episode 8: Boots, Bots, and $600 Billion

A Texas rodeo opens the episode. A failed coding experiment sets the tone. And then the big question lands: If AI is attracting historic levels of investment, why does it still feel incremental? Bill and Kurtis unpack the J-curve of innovation, the Magnificent Seven’s infrastructure race, AI agents that work while you sleep, the security risks nobody’s talking about, and why healthcare may quietly be the biggest near-term winner. It’s a ramble… but the good kind.

Episode 7: Zillow enters the chat, and the moment AI stopped being a choice

In Episode 7 of Under The Hoodie, Bill Fowler and Kurtis Cicalo kick off the show’s second calendar year with a grounded recap of what actually mattered in AI during 2025—and why the pace of change makes “annual recaps” feel almost absurd. They dig into the Zillow–OpenAI partnership and why it sent shockwaves through real estate, unpack the real (and often invisible) cost of large language models as infrastructure, and react to California’s new requirement to disclose AI-altered listing photos—an early signal that trust and regulation are catching up to generative tech. The conversation closes on the next inflection point: agentic AI. Not demos, not hype—but systems that act on our behalf. Powerful, inevitable, and still deserving of human supervision.