Fear of making the wrong move is why most aspiring hotel investors never get started. And ironically, that hesitation is costing them more than any mistake ever would.

In this episode, you'll learn how one developer went from zero hotel experience to 50% NOI margins, a REIT acquisition, and a second brand now scaling to 10+ locations across the US.

A former McKinsey consultant turned landscape resort developer who built two properties from scratch, sold 90% to a REIT, and is now pioneering a land lease model that cuts carrying costs by two-thirds, joins us to break down exactly how he did it. Ben Wolff's direct booking strategy drives 80-85% of revenue without relying on OTAs, and his marketing firm OASI exists because traditional hotel agencies simply couldn't keep up.

In this episode, you'll discover:

• Why a $300K procurement mistake early in development didn't sink the project and what it taught him about vetting manufacturers
• The land lease structure that makes a $7M property deal actually pencil when outright ownership never would
• How 50% NOI margins are achievable when most traditional hotels average half that
• Why direct bookings command higher ADRs than OTA guests, and the exact content strategy behind it
• The lean staffing modelis running 63 keys across two properties without bloated overhead
• The one mindset shift that separates developers who survive ground-up builds from those who quit

If you've been waiting until you know enough, have enough, or feel ready enough to get into boutique hospitality, this episode is your sign to stop waiting. The most expensive mistake in this business isn't the one you make. It's the deal you never took a shot at.

About Ben Wolff

Ben Wolff is the Co-Founder of Onera, a luxury landscape hotel brand that achieved a historic milestone with the sector’s first public REIT acquisition by Summit Hotel Properties. As the Founder and CEO of Oasi, he leverages data-driven social storytelling to help experiential properties drive over 80% of bookings directly and achieve 50%+ NOI margins. A former McKinsey consultant turned hospitality innovator, Ben is currently developing Baya, a tropical agritourism resort in South Florida, while redefining the economics of unique stays for the modern traveler.

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If you're still tracking your hotel pipeline in Excel and spending two hours screening each deal, you're working harder than you need to. Ziggy Hallgarten lived with that frustration as an analyst, so he built the solution.

In this episode, you'll get fresh market insights from the ALIS Conference, learn how AI can cut your deal analysis time dramatically, and hear what the entrepreneurial journey looks like when you're solving a problem you experienced yourself.

A Cornell Hotel School graduate who worked in acquisitions at institutional firms before founding Broome.ai shares what he's seeing in the hotel market, why he left to build his own company, and how AI is transforming the way investors analyze deals. Ziggy Hallgarten bootstrapped his startup after watching teams waste hours on manual workflows, teaching himself to build software using AI tools to automate the deal screening process he knew was broken.

In this episode, you'll discover:

• What the mood was really like at this year's ALIS Conference, and which markets are heating up
• How Broome.ai cuts deal screening from 2 hours down to 30 minutes or less by automating data extraction
• Why Ziggy left his family's hotel business to build his own company from scratch
• Free tools you can use to build software prototypes without any coding knowledge
• Where AI will have the biggest impact on hotels: revenue management and operations
• The biggest mistake founders make: trying to solve every problem instead of focusing on one
• Practical ways hotel investors can start leveraging AI in their workflow today

Whether you're an independent operator trying to compete with bigger shops, curious about where hotel investing is headed, or thinking about starting something of your own, this conversation delivers real insights from someone living on both sides of it.

About Ziggy Hallgarten

Ziggy Hallgarten is the Co-Founder and CEO of Broome, a software company building AI agents that automate the complex administrative workflows of Commercial Real Estate transactions. A graduate of Cornell’s Hotel School, he traces his hospitality roots from folding towels as a 10-year-old pool boy to managing acquisitions for institutions like PGIM Real Estate and family offices like Oliver Companies. Frustrated by the inefficiencies of the deal process, Ziggy transitioned from investor to founder in 2025 to build the solutions he needed as an analyst.

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What if there's a way to scale a hospitality portfolio without having to own the real estate? For operators looking to grow quickly without raising millions in equity or navigating complex bank financing, the OpCo-PropCo model offers a compelling alternative path.

In this episode, you'll discover how to build a hospitality brand by leasing properties instead of buying them, command premium ADRs without real estate risk, and scale across multiple markets using the OpCo-PropCo model.

An outdoor hospitality founder who operates campgrounds, backcountry lodges, and micro-hotels across Colorado, Arkansas, and California shares how he scaled to four properties in three years without traditional financing. Sam Degenhard's Campfire Ranch model separates operations from ownership, partnering with land investors who buy the real estate while he focuses on building a brand that commands $90 to $1,400 ADRs and spends just 2-3% of revenue on marketing.

In this episode, you'll discover:

• The exact lease structure that lets you scale hospitality properties without raising millions for acquisitions
• How to partner with real estate investors who buy the land while you control 100% of operations and guest experience
• Why focusing on the business side lets you open properties faster with significantly less capital
• The owner-operator staffing model that runs an 8-bedroom lodge profitably with one employee
• How to command 4-5X market rates by building brand loyalty instead of competing on OTA platforms
• The due diligence process that identifies underperforming assets is perfect for operational turnarounds
• Why subscale properties under 30 keys deliver better margins than traditional hotel models

Whether you're an operator exploring faster paths to scale or an investor looking to understand how hospitality brands grow without traditional real estate ownership, this episode reveals a proven model that separates the business of hospitality from owning the dirt and the strategic advantages that come with focusing purely on operations.

About Sam Degenhard

Sam Degenhard is the Founder and CEO of Campfire Ranch, a vertically integrated outdoor hospitality brand building a diverse "collection" of adventure basecamps, ranging from developed campgrounds to backcountry huts and renovated lodges. A veteran of Red Bull’s sports marketing team, Sam famously traded his corporate career for life in a teardrop trailer on public land, launching a business dedicated to removing the "friction" of camping for the experience generation. He now specializes in the acquisition and operation of sub-30-key assets in high-recreation markets like the Rockies, the Ozarks, and the Sierra, utilizing an OpCo model to partner with real estate investors while delivering high-touch, community-driven guest experiences.

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Email Us at info@hotelinvestorplaybook.com

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