Hands-On vs Hands-Off Hospitality - Ben Wolff and Irene Wood Debate

Send us a textConnor welcomes new co‑host Shari Heilala to dig into the data, the grit, and the joy that power outdoor hospitality—from feasibility studies and appraisals to design choices that actually raise rates and length of stay. Shari brings a rare mix: she’s valued massive retail portfolios, led international corporate services, developed her own apartments, and for years has guided campgrounds, RV resorts, and glamping projects with lender‑ready analysis.We get practical on what separates a viable concept from a pretty pitch. Shari breaks down the difference between appraisals and feasibility studies, why most outdoor resort valuations are income‑driven, and how lenders read assumptions on occupancy, ADR, expenses, and debt coverage. We explore the shifts inside RV demand—why travel trailers outpace big rigs today, how tow vehicles and fuel costs shape modern rigs, and what is changing in RV resort site design. On the glamping side, we look at competitive edges that last: water access, dark skies, privacy, unique, or uniquely inspired architecture and design. Permitting and entitlements get real talk as well. We share how specialist architects streamline hearings, craft persuasive site plans, and help avoid costly missteps. Shari also opens up about the personal why: growing up on lakes, chasing dawn wakeboard sessions, and believing that well‑designed nature stays are durable because they restore people. If you’re planning a glamping site, expanding an RV resort, or just curious how the best outdoor properties are built, this conversation gives you a roadmap. Subscribe, share, and consider leaving us a review with the one question you want us to tackle next.Clockwork Design Outdoor hospitality's top architecture & design firm. To learn more email [email protected] Outdoor AdvisorySage is the leading outdoor consultancy in feasibility studies and appraisals in the USA.Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textWe trace Joe Lisa's path from college painting gigs to a $13m experiential hospitality portfolio, exploring how purpose, scrappy execution, and smarter permitting turned failures into fuel. From desert yurts to a reborn Ohio marina, we share what scales, what breaks, and why charm wins.• Aligning purpose with business and life• Invest in your own self development• Soul Stay’s waterfront build and unit mix• Permits, zoning, septic, and conditional use• Bootstrapping Arizona and 29 Palms off‑grid• When to sell, when to scale, when to pause• Boutique charm versus economies of scale• AI for guest messaging, ops, and deal sourcing• Midwest advantages and buy‑box discipline• Working with local government and media• Green flags and red flags in distressed deals• Upcoming sites in Florida and West YellowstoneLinks:Joe Lisa LinkedinSol Stay Lodge and Marina in Sandusky, OHThis episode is brought to you by Clockwork Design- outdoor hospitality's top architecture & design firm. To learn more email [email protected] episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textWhat if a small, story-rich resort could command a seven-figure brand premium—and what would it take to build one? We sit down with creator-operator Isaac French to trace the arc of Live Oak Lake.  From building Waco's first micro resort, an early Airbnb suspension that forced an unexpected direct booking strategy, and a sale shaped by the power of narrative. Isaac opens up about the choices behind fewer, better units, and why biophilic design moves both hearts and numbers.Live Oak Lake origin, design-led build, and early tractionThe Airbnb suspension forcing a direct booking strategyUnreasonable hospitality as a design and operations ethosBrand value, opco-propco structures, and earnest moneyWhere social media is headed for hospitality Biophilic design, indoor–outdoor living, and wellnessA 200-tree orchard as living artwork and venueFarm hospitality as the next major opportunityValues-based community, family, and craft-forward livingSubscribe to Isaac’s newsletter at IsaacJFrench.com for short lessons and stories on design, hospitality, and building a better life and businessFind Isaac on socials at @IsaacFrench_This episode is brought to you by Clockwork Design- outdoor hospitality's top architecture & design firm. To learn more email [email protected] episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textA 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 DesignOutdoor hospitality's top architecture & design firm. To learn more email [email protected] Outdoor AdvisoryThe leading outdoor consultancy in feasibility studies and appraisals. To learn more email [email protected] This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textSoon, 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.This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textNick 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. This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textMatt 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 [email protected] to see if their services are right for your project. For inquiries or feedback email Connor at [email protected] you appreciate this free content, please consider leaving our podcast review!This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textAre 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 [email protected] to see if their services are right for your project. For inquiries or feedback email Connor at [email protected] you appreciate this free content, please consider leaving our podcast review!This episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textHear 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:  [email protected]'s email:  [email protected]'s email:  [email protected] episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!

Send us a textThe 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 AmericaThe Glamping Insider (Nick's newsletter)Posh OutdoorsSage Outdoor AdvisoryNick's email: [email protected]'s email: [email protected] episode is powered by Sage Outdoor Advisory the industry leaders in feasibility studies and appraisals. We work hard to bring you the best insights from top experts in this space- FREE OF CHARGE, all we ask is that you consider leaving us a positive review so we can keep the momentum growing. To leave a review go to the podcast home page and scroll down past some of the first episodes - we appreciate you!