Under The Hoodie

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?

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.

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.

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.

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.

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 systems start taking initiative on their own. They dig into training data ethics, UMG–Udio style revenue sharing, infrastructure costs (GPUs don’t last forever), and why human-made art—and MLS data—may become more valuable as AI floods the zone.

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 EpisodeFutureproof by Kevin RooseArtificial Intelligence (HBR Insights Series)The Sequence newsletterTowards Data Science blog