How to Finance and Underwrite Unique Stays: Navigating Investment Opportunities in a New Hospitality Landscape

In this episode, you’ll meet Shari Heilala — the founder of Sage Outdoor Advisory, an appraisal services consultancy for campgrounds, glamping resorts, and experiential hospitality companies. 

With over 30 years in commercial real estate, Shari shares her journey from valuing hotels at Cushman & Wakefield — one of the world’s largest commercial real estate services firms — to becoming a leader in the unique stays space, helping hospitality entrepreneurs navigate the complexities of financing and underwriting innovative properties.

Shari dives into the growing demand for nature-immersive stays, the challenges of securing investment for unconventional assets, and why institutional capital is starting to take notice of this emerging market. She also explores the resurgence of independent hoteliers, driven by a new wave of creative entrepreneurs who are blending luxury, design, and outdoor experiences to redefine hospitality.

Whether you're a budding hospitality entrepreneur or a seasoned investor, Shari offers invaluable insights into how to build a successful, data-driven strategy in this evolving, exciting, and at sometimes murky space.

Connect with Shari

Learn more about Sage Outdoor Advisory

This episode is brought to you by Enso Connect

My new friends at Enso Connect have created a tool that’s putting AI to work in a way that’s saving hospitality pros countless hours every week.

Here’s how it works: Enso Connect’s Guest Messaging Insights tool dives into your guest messages across all booking platforms. Using AI, it analyzes these interactions and pulls out hidden opportunities that you might be missing.

And the best part? It’s FREE, and you’ll get your personalized report in just 72 hours.

Here’s what this AI-powered report will do for you:

• Analyze your message volume so you can see exactly where your time is going.
• Break down common guest questions, giving you the info you need to improve your property listings and FAQs.
• Provide sentiment analysis to understand how guests feel and spot potential issues before they escalate.
• Offer personalized recommendations that highlight upselling opportunities you might have overlooked, allowing you to tailor your services more effectively.

Get the report 

About the Show

Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai

Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn.