Experienced real estate investors make the jump into hospitality every year. Most of them underestimate what they're getting into.

In this episode, you'll hear what it actually looks like when a seasoned commercial operator buys his first boutique hotel, and what he'd do differently.

A commercial real estate investor who built a $75M portfolio across retail, self-storage, flex space, and adaptive reuse projects shares the unfiltered story of acquiring, renovating, and opening Salt Ranch, a 48-key boutique hotel in Nashville. Tyler Cauble had zero hospitality experience going in, and he's not shy about what that cost him.

In this episode, you'll discover:

• How he got financing after 50 lender rejections by redesigning a $17M project down to $10.5M
• Why old buildings will always surprise you, and how to protect yourself with the right contingency
• How tariffs added $150,000 in unexpected costs and what he'd build into his underwriting today
• The partner debt strategy he used instead of a capital call when costs ran over budget
• What he learned from interviewing 25 hotel management companies before selecting one
• Why does he say investing $50K in education before your first deal will outperform almost any return

If you're considering making the jump from commercial real estate into hospitality, or want to learn from someone who did it with eyes wide open, this one is worth your time.

If you found value in this episode, take 30 seconds to leave us a review here. It helps more people find the podcast and keeps us bringing on great guests.

Connect with Tyler Cauble

Website: https://www.tylercauble.com/ & https://saltranchhotel.com/

LinkedIn: https://www.linkedin.com/in/tylercauble/

YouTube: https://www.youtube.com/tylercauble

Instagram: https://www.instagram.com/commercial_in_nashville/

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What does it actually cost to build a boutique hotel from scratch in a foreign country? More than you think, and not just financially.

A short-term rental operator running 220+ properties across 40 cities is now three years into building a 20-unit boutique resort in Medellin, Colombia. No bank financing. A licensing process that restarted from zero. And a price tag is climbing toward $4.5 million. Tim Hubbard joins the show to walk through every layer of this project with total transparency.

In this episode, you'll discover:

• The real cost breakdown of a ground-up international hotel development and why it ballooned past initial estimates
• Why foreign investors can't get bank financing in Colombia, and how Tim structured the deal without it
• How a licensing change wiped out months of progress and what it taught him about developing abroad
• The partnership structure that made this project possible, and what Tim wouldn't have attempted alone
• How his virtual management company, Corzly, operates 220+ STRs across 40 cities at 5-10% fees
• Where AI is actually delivering results in hospitality operations today, and where it still breaks down

If you've ever visited a city and thought about building something there, this episode is the honest version of what that journey actually looks like.

Connect with Tim Hubbard

Website: https://corzly.com/

LinkedIn: https://www.linkedin.com/in/tim-hubbard-str/

Podcast: https://strriches.com/

If you found value in this episode, take 30 seconds to leave us a review here. It helps more people find the podcast and keeps us bringing on great guests.

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Most people who buy their first hospitality property don't realize they just bought themselves a 90-hour-a-week job. The difference between owning a business and being trapped inside one comes down to a single number most investors never bother to calculate before they sign.

In this episode, you'll learn the exact revenue threshold your property needs to hit before you can hire real staff, implement real systems, and actually step away from day-to-day operations.

A 26-year campground owner and operator who won 8 consecutive industry awards and now consults for investors and operators across North America breaks down what most first-time buyers get dead wrong. Greg Emmert has evaluated hundreds of deals and knows exactly where the line is between a profitable business and an expensive hobby.

In this episode, you'll discover:

• The minimum revenue number that separates real business owners from glorified employees
• Why "armchair quarterback syndrome" costs first-time hospitality investors more than any bad deal
• The infrastructure trap that can turn your dream property into an undevelopable piece of dirt
• How the work exchange model can supplement your labor force without destroying your payroll
• Why banks are now requiring third-party management before they'll write a check on hospitality assets
• The one thing experienced operators do before every acquisition that most beginners skip entirely

If you're serious about buying a hospitality asset and actually owning it instead of working inside it, this episode will save you from the most expensive lessons in the business. Don't learn them on your own dime.

About Greg Emmert

Greg Emmert is the Founder and Principal Consultant at Vireo, bringing over 30 years of award-winning experience to the outdoor hospitality sector. As the former owner and operator of the 240-site Homerville KOA in Northeast Ohio for 26 years, he guided the property to consistent profitability, Net Promoter Scores in the high 80s, and eight consecutive KOA President’s and Founder’s Awards. Today, Greg leverages his extensive hands-on background to help park owners and investors navigate market feasibility, pressure-test acquisitions through rigorous due diligence, and build scalable Standard Operating Procedures. Recognized as the 2019 Outstanding Environmental Educator and a passionate "bird-nerd," he also specializes in helping operators tap into the conservation economy to design premium, nature-based guest experiences that drive intense loyalty.

Connect with Greg Emmert

Connect with Greg on LinkedIn.

Visit their Website.

Learn how to use AI to underwrite faster, streamline operations, automate the busy work, and make better decisions. Start your 7-day free trial of the AI for CRE Collective here.

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Email Us at info@hotelinvestorplaybook.com

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Jasper Ribbers went from trading equities on Wall Street to traveling to 100 countries as a digital nomad, funding it all from a single Airbnb apartment in Amsterdam. Today, he manages pricing strategy for over $125 million in annual short-term rental bookings and co-founded Freewyld, a micro-resort brand in Idyllwild, California that's pulling $190 RevPAR against a $97 market average. In this episode, Jasper reveals which STR markets worldwide are generating the best returns right now, why 99% of operators are leaving up to 40% of their revenue on the table with "set it and forget it" pricing, and breaks down the exact financials behind his micro-resort. Whether you're scaling a short-term rental portfolio or looking to break into hospitality investing, this episode is loaded with real data, real numbers, and real strategies you can use this week.

About Jasper Ribbers

Jasper Ribbers is a former corporate equity trader turned hospitality entrepreneur, currently serving as the Co-Founder of Freewyld and the Head of Revenue Management at Freewyld Foundry. As a pioneer in short-term rental revenue optimization, he leverages his background in econometrics to actively oversee pricing strategies for over $125 million in annual bookings globally. He is widely recognized as the author of the foundational industry book Get Paid for Your Pad and host of its accompanying podcast, which has amassed nearly 2 million downloads across more than 700 episodes. Today, Jasper is dedicated to helping property operators maximize their profits through dynamic pricing routines and scale their portfolios from single-family units to commercial boutique micro-resorts.

Connect with Jasper Ribbers

Connect with Jasper on LinkedIn.

Follow Jasper on Instagram.

Visit their website, Freewyld and Freewyld Foundry.

Learn how to use AI to underwrite faster, streamline operations, automate the busy work, and make better decisions. Start your 7-day free trial of the AI for CRE Collective here.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

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What does a land investor who's done 400+ deals have to teach hotel investors? More than you'd expect.

In this episode, you'll discover how the same principles behind finding off-market sellers, creating value through entitlements, and building passive income apply directly to hospitality investing, even if you've never bought a single acre of dirt.

A former Army officer turned land-investing expert joins us to break down how he built a machine that generates $44,000 a month in passive income, then intentionally tore it down to focus on fewer, higher-margin deals while working just five hours a day.

In this episode, you'll discover:

• Why the sellers who accept below-market offers aren't desperate, they're motivated, and the distinction matters for hotel acquisitions too
• The 3-step market selection framework that identifies where deals are actually moving before you spend a dollar
• How shifting from high-volume, low-margin transactions to low-volume, high-profit deals changed everything
• The infrastructure plays a role in turning raw land into turnkey assets, and why hotel developers should be paying attention
• Why scaling your team is often the problem, not the solution
• The 10 am-3 pm boundary that forced a complete redesign of a 7-figure business

If you're serious about building a real estate portfolio that funds your lifestyle instead of consuming it, this episode will challenge how you think about time, scale, and where the real leverage is hiding.

About Brent Bowers

Brent Bowers is a former US Army Officer, CEO of ZechBuysHouses LLC, and the founder of The Land Sharks, a premier coaching program dedicated to helping investors build legacy wealth through vacant land. Seeking a way to spend more time with his family after multiple military deployments, Brent pivoted from traditional real estate to raw land, utilizing creative seller financing and mobile home packages to build a massive passive income machine. Having completed nearly 400 successful land deals, he now mentors aspiring entrepreneurs on how to achieve financial and lifestyle freedom without the typical headaches of tenants, toilets, or termites. Brent passionately leads his business and life based on Bob Burg’s philosophy: "Your influence is determined by how abundantly you place other people's interests first".

Connect with Brent Bowers

Connect with Brent on LinkedIn.

Subscribe to his YouTube channel or follow him on Instagram.

Visit their Website.

Learn how to use AI to underwrite faster, streamline operations, automate the busy work, and make better decisions. Start your 7-day free trial of the AI for CRE Collective here.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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.

Connect with Ben Wolff

Connect with Ben on LinkedIn.

Follow him on Instagram.

Visit their Website.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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.

Connect with Ziggy Hallgarten

Connect with Ziggy on LinkedIn.

Visit their Website.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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.

Connect with Sam Degenhard

Connect with Sam on LinkedIn.

Follow them on Instagram or visit their Website.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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