In this episode of The Radical Hospitality Podcast, host Zeke Freeman sits down with Tyler Cauble, a Nashville-based commercial real estate investor, advisor, and developer known for turning overlooked properties into community anchors through adaptive reuse and neighborhood-first strategy.

Tyler shares how he dropped out of college, landed an in-house leasing role at a boutique development firm, and quickly built real-world experience across office, retail, industrial, and development. After completing his first major development project, he launched his own firm and began raising capital for deals rooted in a clear philosophy: be product-type agnostic, but hyper-local about where you invest. For Tyler, that means spending nearly all his time understanding the real fabric, demand, and trajectory of specific neighborhoods like East Nashville and Madison.

Takeaways:

• Tyler Cauble emphasizes the importance of understanding neighborhood dynamics for successful investments.
• He prefers commercial real estate over residential due to the complexities of tenant relationships.
• Tyler's approach to underwriting deals focuses on finding the 'X factor' that sets projects apart.
• He believes in the potential of opportunity zones to spur investment in neglected areas.
• Tyler discusses the challenges of navigating city regulations and permitting processes.
• He highlights the significance of choosing the right management team for hospitality projects.
• Tyler's Peerless Mill project aims to create a self-sustaining community within a mixed-use development.
• He stresses the need for conservative underwriting in uncertain market conditions.
• Tyler shares insights on the benefits and challenges of utilizing historic tax credits.
• He advocates for hiring experienced professionals to navigate complex financing options like TIFs.

Connect with Tyler Cauble:

Website: crecentral.com

Instagram: @commercialinnashville

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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In this episode, Zeke Freeman sits down with Steph Weber, a branding and marketing leader in the short-term rental, boutique hotel, and micro resort space. Steph shares the origin story behind her move from fashion and influencer marketing into hospitality, and why story-led branding is no longer optional as platforms shift and competition tightens.

They unpack what “owning your brand” really means for STR and boutique operators, how to build a brand before construction is even finished, and why strong marketing systems (email lists, content, direct bookings) become part of the business asset itself, especially when it’s time to exit.

What you’ll learn

• How Steph went from fashion branding and influencer work to hospitality investing and development
• Why storytelling is the competitive edge in modern STR and boutique hotels
• The difference between “good design” and a stay that creates emotion (and loyalty)
• How to define a target guest profile that guides everything from amenities to messaging
• What it looks like to market a property while it’s still under construction
• Why relying on OTAs alone can cost you loyalty, margin, and long-term business value
• The real-world journey of building Cabins on the Cumberland: partnerships, financing, surprises, and lessons learned
• How to think about event venues, capacity, and the economics of full-property buyouts

Connect with Steph Weber:

Website: theweberco.com

Instagram : @theweberco

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

In this episode of the Radical Hospitality Podcast, Zeke Freeman interviews Brandon Gore, a craftsman known for his work in concrete artistry and sustainable building. Brandon shares his journey from a career in hospitality to becoming a designer and builder, emphasizing the beauty and longevity of rammed earth construction. He discusses his current project, the Outlier Hotel in Eureka Springs, Arkansas, which aims to provide unique accommodations for visitors. The conversation explores the challenges and benefits of rammed earth, the importance of craftsmanship in design, and the search for strategic investment to bring the Outlier Hotel to life.

Takeaways:

• Brandon Gore's journey into concrete artistry began with a passion for mountain biking and architecture.
• His work emphasizes sustainable building materials and timeless design.
• Rammed earth construction offers longevity and minimal maintenance compared to traditional materials.
• The Outlier Hotel aims to cater to a demographic seeking modern, unique accommodations in Eureka Springs.
• Brandon's experience with Dwell Magazine significantly boosted his career and visibility in the industry.
• Rammed earth is gaining traction in building codes across the U.S., but still faces challenges due to historical lobbying.
• The Outlier Hotel project is strategically located near popular attractions, enhancing its market potential.
• Brandon seeks a strategic investor who shares his vision for the Outlier Hotel.
• Market studies indicate strong demand for high-end accommodations in Eureka Springs.
• Brandon's personal connection to the area drives his commitment to creating meaningful spaces.

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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If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

In this episode of the Radical Hospitality podcast, host Zeke Freeman interviews Scott Lamont, CEO of EDSA, a global landscape architecture and design firm. They discuss Scott's journey in the industry, EDSA's unique approach to design that emphasizes the importance of place, and the collaborative nature of their projects. The conversation covers various topics including the design process for resorts, the challenges of working in different countries, and the balance between development and preservation. Scott shares insights on current trends in boutique hospitality and offers advice for aspiring developers looking to create unique experiences.

Takeaways

• Scott Lamont emphasizes the importance of designing within a place, not just in it.
• EDSA's philosophy centers on curiosity, humility, and collaboration.
• The firm has a diverse portfolio, including hospitality, urban design, and community planning.
• Understanding local cultures and communities is crucial in the design process.
• Collaboration is key; great destinations are a collective vision.
• The trend is shifting towards boutique resorts that offer unique experiences.
• Master planning is an evolving process that requires flexibility.
• EDSA leverages technology to analyze site data for better design outcomes.
• Community engagement is essential for successful project implementation.
• Hospitality is about delivering experiences and making guests feel welcome

Connect with Scott LaMont:

Website: EDSA - https://www.edsaplan.com/

LinkedIn: Scott LaMont

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

In this episode, Zeke heads up to Evergreen, Colorado, to explore the story behind Juniper, a boutique lodge on a 10-acre property that is transforming into Colorado’s first treehouse hotel. Owners Alea and Ashley take us through their six-year journey—from buying a former B&B with zero hospitality experience to building luxury treehouses, hosting intimate weddings, and creating deeply personal guest experiences rooted in nature, design, and storytelling.

This conversation pulls back the curtain on what it really takes to create an experiential micro-resort:

• Turning an old bed-and-breakfast into a modern boutique stay
• Balancing operations while still living on property
• The realities of building treehouses (why so few exist in the U.S.)
• How design, soundproofing, durability, and cleanability truly make or break a hotel
• Why “first five feet, first five words, first five seconds” defines their entire guest philosophy
• Cultivating community trust through transparency, neighbor engagement, and listening
• The long road of permitting, planning commissions, and navigating short-term rental regulation
• The irreplaceable role of story, small moments, and human connection in hospitality

From the magic of themed treehouses to the weight of running a property without investors, Alea and Ashley share lessons in perseverance, design thinking, leadership, regulation, and the heart-led grit required to build something extraordinary.

This episode is a masterclass for hospitality entrepreneurs, boutique hotel developers, short-term rental operators, and anyone dreaming of building a place that inspires awe.

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

We’re on site with Tony to tour his newly built accessory dwelling unit (ADU) in Wheat Ridge, Colorado—a project that began as a simple garage and evolved when the city legalized ADUs. We unpack the real-world timeline (design do-overs included), what changed structurally from “just a garage” to a conditioned dwelling, and the big calls that move the budget—radiant heat, insulated doors, and a sewer ejector pit—so you can scope your own ADU with eyes wide open. Tony also shares how he’s weighing rental strategies (medium-term vs. short-term vs. long-term), why finish quality matters when it’s in your backyard, and the features that make the space livable for residents and useful for his home-based business.

Highlights:

• Why the shift from garage to ADU: Once Wheat Ridge approved ADUs, adding water/sewer/power anyway made a full unit make sense for rental income and property value.
• Permitting & design timeline: ~4–5 months with a couple of stop-starts after redesign; smoother than horror stories but still iterative.
• Structure & envelope upgrades: Deeper foundations, full insulation, and R-17 foam-packed garage doors with side-mount motors (about $12K total) to keep conditioned space tight and clearance high.
• Budget reality: Low $300Ks possible on a lean spec; this build landed ~$450K with high-end choices (radiant, solid-core doors, finishes, ejector pit).
• Rent strategy thinking: Leaning medium-term (traveling professionals, 30–90 days) for lower turnover than STRs and more flexibility than year-long leases.

Homeowners, small developers, and designers weighing a garage-to-ADU conversion; anyone curious about Wheat Ridge/Front Range ADU realities—costs, code, utilities, and rental strategy.

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

In this episode of The Radical Hospitality Podcast, host Zeke Freeman sits down with Preston Snyder, Principal of Thomas Preston Real Estate and founder of Mad Hospitality in Madison, Georgia.

Preston shares how his early exposure to both real estate restoration and world-class hospitality at the Ritz-Carlton shaped a career that fuses adaptive reuse development with culinary innovation. Since 2020, he’s revitalized Madison’s town square by converting vacant historic buildings into thriving concepts like The Dining Room, The Sinclair, Heart & Crown Tavern, Betty Gene's Pop-Up at Buggy Works, and the retro South Motor Inn.

The conversation dives into:

• Lessons from decades in both real estate development and hospitality
• How adaptive reuse projects fuel local economies and community culture
• Building multiple restaurant concepts from a centralized kitchen model
• Investing in people: why Preston provides benefits, stability, and growth opportunities uncommon in the restaurant world
• Pivoting, experimenting, and staying resilient—even after setbacks like a fire at Betty Jean’s

Preston’s story is both entrepreneurial and deeply personal—showing how vision, grit, and hospitality can transform not just properties, but entire communities.

👉 Learn more about Preston’s work:

• Thomas Preston Real Estate: thomasprestonrealestate.com
• Mad Hospitality: mad-hospitality.com

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.

In this episode of the Radical Hospitality Podcast, Zeke sits down with Mike Messeroff—a 30-year veteran of the hospitality industry, coach, and founder of the Carpe Diem Collective. Mike’s journey has taken him from JetBlue’s corporate offices to bartending across the globe, through deep personal lows, and into a life of coaching leaders toward purpose and wellbeing.

They discuss Mike's journey from corporate success to personal fulfillment, emphasizing the importance of self-hospitality, mindfulness, and community support in the hospitality industry. Mike shares insights on the challenges faced by service workers, the significance of meditation, and the power of positive thinking. The conversation culminates in a guided meditation session, encouraging listeners to prioritize their mental well-being and personal growth.

Mike opens up about:

• His decision to leave a secure corporate career for a more adventurous path in the Caribbean, Australia, New Zealand, and beyond
• The wake-up call of hitting rock bottom while living what seemed like a “dream life” in Breckenridge
• How mindfulness and meditation transformed his mental health and career trajectory
• Why burnout is rampant in hospitality—and how “self-hospitality” can change the culture
• The practices he teaches leaders: meditation, gratitude, and filling your own cup first
• Building the Carpe Diem Collective, a purpose-driven community where hospitality leaders can exhale, connect, and realign with joy

Mike also guides listeners through a short meditation during the episode, offering a practical tool you can use anytime you need to reset.

If you’re in hospitality or simply in need of a reminder to slow down, breathe, and reclaim your purpose—this conversation is for you.

🔗 Explore Mike’s free masterclass at self-hospitality.com

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.

Follow, Rate & Review:
If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.