Under The Hoodie
Bill Fowler, Kurtis CicaloHosted 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 a... more
| Publishes | Twice monthly | Episodes | 13 | Founded | 9 months ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Technology | |||
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Latest Episodes
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 bigge... more
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 “interre... more
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 r... more
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 ... more
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 ... more
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 in... more
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, corp... more
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 s... more
Key Facts
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Apple Podcasts | #135 |  Israel/Technology |
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Audience Metrics
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| Listeners per Episode | Gender Skew | Location | |||
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| Interests | Professions | Age Range | |||
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Under The Hoodie launched 9 months ago and published 13 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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