Hosted by Bill Fowler, a veteran real estate tech strategist navigating AI adoption like his career depends on it—because it just might. He’s joined by Kurtis Cicalo, CEO of a thriving AI startup and one of the rare founders who can build the future while still asking the big “what does it mean?” questions. Together, they explore how AI is transforming the way we live and work across real estate and beyond. No hype. No fearmongering. Just honest, unscripted conversations about what’s exciting, what’s unsettling, and what’s next. If you feel late to the AI party, they’ve saved you a seat.
Episode 14: AI Is Making Life Easier… But Are We Getting Too Comfortable?
AI can write your emails, analyze data, troubleshoot your pool, identify what’s wrong with your car, and answer questions at 11 PM, but at what point do we start trusting it a little too much?
In this episode of Under the Hoodie, Bill Fowler and Kurtis Cicalo are joined by Josh Grant, President & CEO of the Western Upstate Association of REALTORS®, for a conversation about what AI actually looks like in the real world. Josh shares how his organization is using Ardi to expand member support, how AI has changed his own daily workflow, and why verifying AI-generated information still matters. The conversation also dives into AI guardrails, the risk of losing human creativity, increasingly agentic technology, and the big question: if AI is changing this quickly, what comes next?
2 Sept 2026
Episode 13: AI, MLS Data & the Questions Nobody Can Answer | Melissa King
What does AI actually mean for the MLS industry? In this episode of Under the Hoodie, Bill Fowler and Kurtis Cicalo sit down with Melissa King, COO of OneKey MLS, to talk about how AI is changing the way she works, how OneKey is approaching AI adoption, and what it could mean for the future of MLS organizations.
From AI-powered workflows and member support to data accuracy, privacy, and the future of work, Melissa shares an operator’s perspective on navigating a technology that’s evolving faster than anyone can predict.
27 May 2026
Episode 12: The Craftsmen vs the Machines
This week on Under The Hoodie, Bill and Kurtis accidentally stumble into one of their deepest conversations yet: are today’s AI coding tools creating the modern version of the Industrial Revolution?
Starting with a viral debate about “vibe coding” and AI-generated software, the conversation spirals into the history of the Luddites, the collapse of craftsmanship, and whether software engineers are becoming overseers of machines instead of builders themselves.
22 Apr 2026
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?
1 Apr 2026
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.
18 Mar 2026
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.
18 Feb 2026
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.
4 Feb 2026
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.
12 Nov 2025
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 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.
27 Oct 2025
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 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.
17 Sept 2025
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 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.
27 Aug 2025
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 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?
20 Aug 2025
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 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.
13 Aug 2025
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 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
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