Under The Hoodie

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 managing this technological shift — the government, corporations, or creators themselves?

From comparing the rise of AI to the dawn of the personal computer, to debating the ethics of automation, “robot taxes,” and even the weirdly promising future of AI actors and custom-made TV endings, this episode captures the humor, unease, and wonder of living through the next big leap.

Stay to the end for their “Excited vs. Terrified” segment — featuring inbox confessionals, music licensing breakthroughs, and one truly unnerving prediction about personalized digital realities.

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 managing this technological shift — the government, corporations, or creators themselves?

From comparing the rise of AI to the dawn of the personal computer, to debating the ethics of automation, “robot taxes,” and even the weirdly promising future of AI actors and custom-made TV endings, this episode captures the humor, unease, and wonder of living through the next big leap.

Stay to the end for their “Excited vs. Terrified” segment — featuring inbox confessionals, music licensing breakthroughs, and one truly unnerving prediction about personalized digital realities.

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 staff fears about job replacement to the challenge of serving multilingual members, Angie shares how MIBOR rolled out Ardi to boost efficiency without losing the human touch. The crew also dives into the bigger picture: why people fear change, how AI is reshaping language, and what excites (and freaks out) us most about where this tech is headed.

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 replacement, while Kurtis unpacks why the shift may have been more about cost savings than progress. The two compare notes on Claude’s charm vs. lack of memory, debate whether fragmentation of AI models is inevitable, and explore what it means to rely on AI for everything from coding to fantasy football drafts. Equal parts critique, comedy, and caution, this episode asks: when your AI starts acting differently, is it evolution—or a breakup?

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 dating app leak exposed thousands of IDs, explore hidden biases baked into models, and debate how much personal data is safe to share with AI. Along the way, they balance the excitement of new agentic tools with the uncomfortable realities of bias, security, and jobs in a world where 40% of Microsoft’s code is already AI-generated.

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 startup, blends a founder’s instinct with a philosopher’s curiosity, always asking the big questions. Together, they’re exploring the seismic shifts reshaping real estate and beyond, cutting through the hype to focus on the breakthroughs, disruptions, and opportunities that matter. Whether you’re skeptical, cautious, or just catching up, this is your backstage pass to understanding AI’s true impact and what’s coming next. The AI party is just beginning. Your seat is waiting.

📚 Mentioned in This Episode

• Futureproof by Kevin Roose
• Artificial Intelligence (HBR Insights Series)
• The Sequence newsletter
• Towards Data Science blog