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A sign-off, a handover, and a candid origin story. We open with why the mic is changing hands and then dive straight into Connor’s path—from a childhood of four brothers and a legendary treehouse to a career shaped by a passion for the outdoors and a data-led obsession with outdoor hospitality investment data. You’ll hear how a sold-out weekend in Joshua Tree reframed “dirt” as valuable inventory, why the numbers pushed him from traditional camping toward glamping, and how a mother–son Kilimanjaro summit trip transformed into a year long 'R&D' trip.

Connor unpacks the deals that almost happened, including a pre-COVID lease-to-own near Smith Rock. We explore his years at Sage building investment-grade feasibility studies, harvesting comp data from hundreds of booking calendars, and partnering to elevate industry insights beyond surveys and into measurable demand. We also confront the hard parts—burnout, trade-offs, and choosing a mission..

Looking forward, Connor maps a clear product vision: hard‑walled, glass‑forward cabins within two hours of major cities, 20–50 keys, indoor–outdoor living without the canvas headaches, and operations designed for an unplugged guest experience. He’s stepping into US‑wide brokerage with his brother while continuing selective consulting and feasibility work, aiming to help founders buy smarter, fund faster, and build places that connect with the natural world. If you care about glamping strategy, outdoor resort feasibility, and the “why” that keeps teams going when permits stall and spreadsheets glare, this one’s for you.

Enjoyed the conversation and want more like this? Follow the show, share it with a friend who loves the outdoors, and leave a quick review so others can find us.

Sponsors:

Clockwork Design
Outdoor hospitality's top architecture & design firm. To learn more email christian@clockwork-ad.com

Sage Outdoor Advisory
The leading outdoor consultancy in feasibility studies and appraisals. To learn more email contact@sageoutdooradvisory.com

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Soon, we’ll be renaming the show to “The Outdoor Hospitality Podcast” to better reflect our mission and expand our content horizons. Make sure to follow and subscribe so you don’t lose us due to the change.

This transformation stems from our core purpose: empowering entrepreneurs and business owners who are creating unique properties that that get people outside. Ultimately, we want our work to help people disconnect from the stressors of daily life and reconnect with nature, loved ones, and themselves.

The new name aligns perfectly with our partnership with Sage Outdoor Advisory, whose expertise spans the entire outdoor accommodation spectrum. Moving forward, we’ll broaden our coverage beyond glamping to include landscape resorts, RV parks, campgrounds, and other innovative outdoor lodging concepts.

We’re also investing heavily in the podcast’s future—with improved production quality and an exciting lineup of industry leaders. To ensure you don’t miss any episodes, follow us on your preferred podcast platform today.

If you’re attending the upcoming Glamping Show, stop by the Sage Outdoor Advisory or Posh Outdoors booth to say hello. We’re excited to continue this journey with you as we explore the ever-evolving world of outdoor hospitality.

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Nick makes a big announcement about stepping back from the podcast to focus 100% on Posh Outdoors and scaling that business. Shari Heilala the CEO of Sage Outdoor Advisory has stepped up as the new Co-Host joining Connor.

Nick shares the latest updates and insights on Posh's successful launch out of the gates.

You can continue to follow Nick on his linkedin and subscribe to his newsletter the glamping insider.

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Matt Bare returns for part two, sharing the real-world challenges of hot tubs, designing a landscape pool, and surviving a hurricane. From health department battles to designing for both luxury and efficiency, this episode reveals what it takes to deliver five-star experiences where adventure and luxury collide.

Learn more on the Glamping Collective website or instagram.

Sponsor: Clockwork Architecture and Design Website the outdoor hospitality industry leader in site design, entitlements, permitting, and architecture.

Email Christian Arnold at christian@clockwork-ad.com to see if their services are right for your project.

For inquiries or feedback email Connor at schwab@sageoutdooradvisory.com

If you appreciate this free content, please consider leaving our podcast review!

Key Words: glamping, landscape hotel, landscape resort, real estate, investing, entrepreneurship, outdoor hospitality

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Are private hot tubs a profitable investment? Is it foolish to build in a booming glamping market with high competition? What is better a glass cabin or luxury dome? What does it take for your glamping property to survive a hurricane? Find out in Part 1 with Matt Bare, the founder of the Glamping Collective near Asheville, NC. He shares how he transformed 130 acres of private mountaintop land into a five-star glamping destination. From uncompromising design to unforgettable guest experiences, Matt reveals what sets the property apart and why passion and excellence drive its success.

Stay tuned for Part 2, where the conversation continues with deeper insights into his journey and the future of glamping.

Learn more on the Glamping Collective website or instagram.

Sponsor: Clockwork Architecture and Design Website the outdoor hospitality industry leader in site design, entitlements, permitting, and architecture.

Email Christian Arnold at christian@clockwork-ad.com to see if their services are right for your project.

For inquiries or feedback email Connor at schwab@sageoutdooradvisory.com

If you appreciate this free content, please consider leaving our podcast review!

Key Words: glamping, landscape hotel, landscape resort, real estate, investing, entrepreneurship, outdoor hospitality

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Hear the secrets behind Sandy Van's meteoric rise in the luxury adventure van market. We are joined by Alan Mondus CEO and Evan Purcell COO as they share their journey from building vans in their driveway to building a $350K luxury adventure vehicles.

Learn more on the Sandy Vans website or instagram.

Sponsor: Sage Outdoor Advisory is the outdoor hospitality industry leader in feasibility studies and appraisals. Schedule a complimentary consultation with the Sage team at sageoutdooradvisory.com.

The Glamping Insider (Nick's newsletter)

• Shari's email: heilala@sageoutdooradvisory.com
• Connor's email: schwab@sageoutdooradvisory.com
• Nick's email: nick@posh-outdoors.com

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The two most experienced managers in outdoor hospitality go head-to-head. Hear insights from Scott Randall and Jacob Halverson. These two managers have worked at the industry leading properties like Paws Up, Auberge, AutoCamp, Mendocino Grove, Wildhaven, and more.

What does it take to become an elite glamping operator? Find out here.

• Wildhaven
• Glampitect North America
• The Glamping Insider (Nick's newsletter)
• Posh Outdoors
• Sage Outdoor Advisory
• Nick's email: nick@posh-outdoors.com
• Connor's email: cjschwab10@gmail.com

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In huge news for the glamping industry, The Fields of Michigan has been acquired by glamping giants, Under Canvas.

Irene Wood returns to the pod to give us the lowdown: How it all went down; the advice she'd give to operators looking for a similar exit; and what's next for her.

Irene is always a blast. Give it a listen!

• Open Sky
• Glampitect North America
• The Glamping Insider (Nick's newsletter)
• Posh Outdoors
• Sage Outdoor Advisory
• Nick's email: nick@posh-outdoors.com
• Connor's email: cjschwab10@gmail.com