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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…
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…
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…
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…
Episode 6: Risk, Reality, and the AI Hype Cycle with Jay Pepper-Martens
Bill, Kurtis, and SFAR CTO Jay Pepper-Martens cut through the AI fog: practical gains vs. hype, how MLSs should vet vendors, why top performers will benefit most, and what happens when agentic…
Episode 5: 100 Million Jobs and Counting: The AI Report That Shook Us
Bill and Kurtis dive into a recent U.S. Senate study predicting that AI could reshape or eliminate 100 million American jobs. What’s hype, what’s real, and who actually bears responsibility for…
Episode 5: 100 Million Jobs and Counting: The AI Report That Shook Us
Bill and Kurtis dive into a recent U.S. Senate study predicting that AI could reshape or eliminate 100 million American jobs. What’s hype, what’s real, and who actually bears responsibility for…
Episode 5: 100 Million Jobs and Counting: The AI Report That Shook Us
Bill and Kurtis dive into a recent U.S. Senate study predicting that AI could reshape or eliminate 100 million American jobs. What’s hype, what’s real, and who actually bears responsibility for…
Episode 4: Angie Baker on Leading Change and Bringing AI to MIBOR
In our first-ever guest episode, Bill and Kurtis sit down with Angie Baker, VP of the Broker Listing Cooperative at MIBOR, to talk about what it really takes to bring AI into the MLS world. From…
Episode 3: When Your AI Best Friend Walks Out On You
In Episode 3 of Under the Hoodie, Bill and Kurtis dive into the chaos of GPT-5’s rollout and the user backlash that followed. Bill laments losing his laid-back “Chatthew” for a stiff, accountant-like…
Episode 2: From Chatbots to Vibe Coding: Where AI Gets Exciting (and Scary)
Bill and Kurtis dig into the real differences between chatbots and large language models, why prompts matter, and how memory changes the AI experience. They unpack the risks of “vibe coding” after a…
Episode 1: What Are We Doing Here, and Why This Matters
The AI revolution is here, and Bill Fowler and Kurtis Cicalo are your guides. Bill, a seasoned real estate tech strategist, betting his career on the AI revolution. Kurtis, CEO of a fast-growing AI…
Frequently Asked Questions
Under The Hoodie has published 12 episodes since August 2025, covering topics in Technology.
Under The Hoodie is currently highly active with new episodes every 2 weeks. Average episode length is 39m.
