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We chart how Ben Wolff scaled from short-term rentals to design-led outdoor resorts, sold into a public REIT, built a content-first marketing firm, and now launches a wellness agritourism brand near Miami called Baya. Clear tactics on funding, pricing, direct bookings and the partners that make it work.

• founder-level partners who own execution and upside
• debt and equity strategies across banks, CPACE, USDA and VCs
• influencer barbell strategy and content-first marketing
• 80 to 85% direct bookings as the North Star
• manual revenue management beyond algorithm defaults
• Onera’s sale, expansion and Wimberley performance
• Oasi’s offer, ROAS mindset and client profile
• Baya concept blending farm, wellness and jungle design
• light, health-forward F&B and sleep technology
• daily routines, AI workflows and energy management
• singles and doubles until capital markets open

Subscribe to Ben Wolff's newsletter via LinkedIn or Ben's instagram @IAm BenWolff.

Onera Fredericksburg and Wimberly Property Websites

Oasi Marketing & Advertising Website

Newbook - www.newbook.cloud

Interested in learning more about Newbook? Book a software demonstration with one of their market consultants today and don't forget to mention you came from the Outdoor Hospitality Podcast to receive 15% off your Newbook subscription and your first month free. This offer is for Newbook Signature subscriptions only.

This podcast 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!

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Connor 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.

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!

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We 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 Yellowstone

Links:

Joe Lisa Linkedin

Sol Stay Lodge and Marina in Sandusky, OH

This episode is brought to you by Clockwork Design- outdoor hospitality's top architecture & design firm. To learn more email christian@clockwork-ad.com

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!