In this episode of the Radical Hospitality Podcast, host Zeke Freeman sits down with Mike Demson—a growth marketer turned real estate developer and boutique hotel operator. Mike’s unique journey began as one of the early employees at Airbnb, where he led global growth initiatives during the company’s breakout years. He shares behind-the-scenes stories from those formative Airbnb days, including the relentless focus on guest experience that shaped his approach to hospitality.
Today, Mike is at the forefront of boutique hotel development with standout projects like The Stone House in Sonoma and 400 Bay Street in San Francisco. He dives into the nuts and bolts of adaptive reuse, value-add renovations, navigating entitlements, and building legacy hospitality assets. From $1 million gut renovations to creative ground-up builds, Mike offers practical lessons on underwriting, construction strategy, management efficiencies, and the art of blending tech, real estate, and hospitality.
Whether you’re a developer, investor, or hospitality enthusiast, this episode is packed with actionable insights on scaling hospitality projects in high-barrier markets like California.
Highlights:
- Early Airbnb growth stories and guest experience lessons
- Deep dive into renovating a 100-year-old Stone House in Sonoma
- Cost breakdowns: budgeting for boutique hotels and short-term rentals
- How to unlock value through entitlements and zoning strategies
- Balancing lifestyle assets with profitability
- Partnership tips for architects, GCs, and management companies
- Market outlook for building hospitality in 2025 and beyond
🎧 Tune in to hear why now might be one of the best times to build hospitality projects despite market headwinds.
Connect with Mike Demson
Instagram: @mike.demson
LinkedIn: Mike Demson
Connect with Zeke Freeman:
Instagram: @zekefreeman_rootarchitecture and @rootarchitecture
YouTube: @rootarchitecture
Facebook: @RootArchitectureandDevelopment
LinkedIn: Zeke Freeman
X/Twitter: @zfreemanroot
Ready to get started with your hospitality project?
https://root-ad.com/
Get in Touch: Stay connected with the Radical Hospitality podcast for more episodes exploring the intersection of architecture, design, and unforgettable guest experiences.
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