Radical Hospitality Show – Details, episodes & analysis

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In this episode of the Radical Hospitality Show, Zeke Freeman sits down with outdoor hospitality expert Connor Schwab to explore what actually makes a glamping, micro resort, or outdoor lodging project work. 

Connor shares insights from hundreds of feasibility studies, explains the real economics of canvas tents versus hard-wall units, breaks down where operators lose money, and reveals how scale, utilities, unit mix, and direct booking strategy can make or break a project. 

They discuss the shift toward professionalization in the industry, why unique architecture creates a long-term moat, and how operators can build profitable, durable outdoor properties in 2026 and beyond.

Things You’ll Learn in This Episode

• How outdoor hospitality has evolved and where it's heading
• Why canvas tents often fail to pencil and the hidden costs behind them
• The operational challenges of glamping and seasonal setups
• Why utilities usually make or break your budget
• How unit mix determines ADR, occupancy, and long-term brand value
• Why scale matters and why most properties struggle below $1M in revenue
• How OTAs can fast-track occupancy but hurt profitability
• Why unique, hand-built units outperform off-the-shelf structures
• What makes a micro resort work in cold or seasonal markets
• Connor’s strategy for building a $100M hospitality portfolio today

Contact Connor Schwab
• Website: https://www.clearsummitinvestments.com/
• Email: connor@clearsummittinvestments.com
• LinkedIn: Connor Schwab
• Podcast: Outdoor Hospitality Podcast

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

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In this episode of the Radical Hospitality Show, Zeke Freeman sits down with Doug Dameron, founding and lead pastor of Orchard Church in Brighton, Colorado. Doug shares the journey of growing Orchard from a small apartment gathering into a thriving multi-site church reaching thousands each week. The conversation explores leadership, vision, accountability, and the often overlooked business side of running a healthy organization. Doug and Zeke unpack how churches and businesses alike can avoid becoming inward-focused, why hospitality is a powerful growth strategy, and how mission-driven leaders can embrace change, technology, and systems without losing their soul. From radical hospitality to kingdom-minded business principles, this episode is packed with practical insights for entrepreneurs, builders, and leaders who want to create lasting impact.

Things You’ll Learn in This Episode

• How Orchard Church grew from an apartment living room to a thriving multi-site organization
• Why vision should focus on people, not just buildings or scale
• The dangers of becoming inward-focused in business and leadership
• How accountability and clarity strengthen culture, not weaken it
• Why hospitality is one of the most powerful and overlooked growth strategies
• What churches and businesses can learn from each other about leadership and systems
• How to balance mission with changing methods in a fast-moving world
• Practical ways AI can support creativity and efficiency without replacing humanity
• The trellis and the vine framework for sustainable growth
• What it means to run a kingdom-minded business in everyday work

Orcharch Church: https://www.orchard.church/
Instagram: https://www.instagram.com/orchardchurchco/
Facebook: https://www.facebook.com/OrchardChurchCo

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

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

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

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.

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

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.

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

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

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

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

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

Zeke tours a new “landscape hotel” of Ben Wolf of Onera that flexes between full-property buyouts and eight private suites—each with its own hot tub—anchored by a communal living/dining hub, a high-end residential kitchen (bar-ready), commissary, and a convertible conference/dining room. The conversation widens into pricing strategy (why weddings aren’t their focus), midweek corporate/wellness retreat demand, smart upsells (private sauna/pool), and the real-world developer playbook: picking the right GC, collaborating with architects, building cash-flow support businesses, and structuring partnerships that actually work. 

We also get the founder’s origin story from NYC nightclub promoter to sober operator to one-of-one hotel developer—plus a sneak peek at a 20-key tropical, agritourism resort coming to South Florida (Bali vibes, stateside).

What you’ll learn:

• How to design a hybrid “house buyout + independent suites” hotel that feels both private and communal
• The revenue logic: midweek retreats > discounted weddings (and where high-ticket weddings still fit)
• Operational upsells that guests love: private pool/sauna access layered onto shared amenities
• Why GC selection trumps low bids—and how to align GC + architect from day one
• Partnership rules that prevent burnout: complementary roles, urgency culture, “project > ego”
• Cash-flow scaffolding for developers: management and marketing arms that keep the lights on
• Agritourism development 101: 99-year land leases, low-density zoning, and farmer revenue share
• Personal arc: sobriety, AirBnB arbitrage, Austin move, RV honeymoon inspiration, and learning the hard way

00:00 Intro & the landscape-hotel concept
03:20 Suite layout, hot tubs, communal core, and event flow
08:05 Pricing strategy: retreats vs weddings; upsell logic
12:10 Kitchen/bar configuration, commissary, and F&B support
17:40 From nightclub promoter to sober operator to developer
23:15 Cash-flow businesses that fund long-cycle development
28:30 GC vs architect: integrated delivery and cost control
34:10 Partnership filters: urgency, role clarity, reputation
39:45 South Florida project: 20 keys, agritourism lease, Bali vibes
46:30 Community/course preview and closing

Listen to another episode of the Radical Hospitality Podcast featuring Ben Wolff:

• Inside a $29 Million Treehouse Resort Business: Funding, Management, a

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

In this episode of The Radical Hospitality Show, Zeke Freeman sits down with Kassidy and Erin Warren to unpack the realities of entrepreneurship, marriage, and building a hospitality business together. From sleeping on air mattresses in dusty renovation sites to scaling into boutique hotels, Kassidy and Erin share the raw grind behind their journey to financial independence. They talk candidly about the toll on their health and relationship, the lessons they’ve learned about individuality and partnership, and how focusing on fitness, mindset, and mentorship has reshaped their lives.

The conversation explores balancing personal identity with a shared vision, why doing hard things together matters in a marriage, and how real estate investment—short-term rentals to boutique hotels—can provide both freedom and challenge. Whether you’re a couple in business, a real estate investor, or simply navigating the tension between personal growth and shared goals, this episode offers grounded wisdom and real stories from the trenches.

Connect with Kassidy Warren:
Instagram: @kassidy.warren
LinkedIn: Kassidy Warren

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.

Send us Fan Mail

In this inspiring episode, Zeke sits down in Waco, Texas with Dale Pahmiyer, VP of Magnolia Realty and a pivotal figure behind the scenes of Fixer Upper. From his early friendship with Joanna Gaines to overseeing Magnolia’s design and construction teams, Dale shares his personal journey into real estate and hospitality—and how the team’s vision has always centered on making space for meaningful moments.

The conversation dives into Magnolia’s real estate culture, the transformation of downtown Waco, the heart behind projects like Hotel 1928, and Magnolia’s commitment to client care, hospitality, and intentional growth. Dale also opens up about a powerful project that provided an accessible home for a family with two disabled children—highlighting how thoughtful design can be life-changing.

Whether you're passionate about real estate, hospitality, or human-centered design, this episode offers insight into what makes Magnolia’s brand so trusted and beloved.

What You’ll Learn in This Episode:

• How Dale became involved with Magnolia and Fixer Upper
• The strategy behind transforming downtown Waco
• Magnolia’s vision: making space for meaningful moments
• Creating boutique hospitality experiences with heart
• How Magnolia Realty cultivates values-based real estate agents
• What makes a “Fixer Upper” property work—and how Magnolia evaluates them
• Designing for accessibility and why it matters
• The story behind the Hotel 1928 restoration
• Magnolia’s slow-growth philosophy and what's next

Resources & Links:
Explore Magnolia Realty: magnoliarealty.com
Learn about Hotel 1928: hotel1928.com
Visit Magnolia Market in Waco: magnolia.com/visit

Grab the free Radical Hospitality Starter Kit → root-ad.com/starter

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.