Under The Hoodie

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...

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 workfl...

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, C...

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...

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...

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 becom...

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 tax...

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 tax...

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 tax...

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...

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 mod...

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...

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...