Explorez tous les épisodes du podcast The Hotel Investor Playbook

Chris Kilcullen has spent three decades in hotels, closing more than $500 million in deals as a senior broker at Avison Young. He's also sold franchises, brokered acquisitions for a REIT, and now built his own hotel concept, so he's seen the flag question from every angle. In this episode, he and Michael dig into the real math: why a commodity economy hotel can lose 30 to 40 percent of its value the moment it drops its brand, and why a well-positioned independent or boutique property can out-earn a branded one because it isn't capped by what guests expect to pay for a templated room. They also cover how Hilton and Marriott are using new soft brands to pull independent hotels back into their loyalty ecosystems, the F&B concept Chris is building to fix the one thing every guest complains about, and why some aging economy hotels are worth more converted into workforce housing than they are as hotels.

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 Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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He's not a hotel investor. He built his career in multifamily and self-storage, growing a portfolio that peaked near $1 billion across more than 4,000 units. But the way he underwrites deals, ranks markets, and raises capital works across every asset class, hotels included. That's exactly why he's on this show.

Data beats gut feel by a million miles. That's his rule, and in this episode, he breaks down the two metrics he checks before touching any deal, the same ones that predict a hotel's performance as reliably as an apartment complex's.

In this episode, you'll discover:

• The two metrics, jobs and supply, that predict a market's future better than population or income growth
• Why one new hotel within a mile of yours can cut your ADR by $10 to $20 a night
• How he renegotiated a construction loan mid-build to save $3.5 million a year when rates nearly doubled
• The two U.S. markets he's bullish on right now, including one riding Big Tech's race for nuclear power
• How he runs a 30-person AI workforce off a $100 mini PC and $250 a month

If you're underwriting your next deal on comps and a hunch, this conversation will show you what data-driven investors track instead.

The ADR stat still lands, it's just doing its job in the bullets instead of the opener, so nothing was lost by cutting that paragraph.

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 Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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What if you bought a rundown bed and breakfast on Zillow, moved in the next day, and turned it into Colorado's first luxury treehouse hotel, all without raising a single dollar from outside investors?

That's exactly what Ashley LaRocque and her wife did. And six years later, their property is booked through 2027, generating six-figure wedding revenue they never saw coming.

A former TV producer who left corporate life to build something from scratch, Ashley shares the unfiltered story of what it actually takes to develop a boutique hospitality asset when banks say no, permits take years, and the build costs keep climbing.

In this episode, you'll discover:

• Why buying an existing B&B beats building from scratch on raw land
• The 3-step permitting process that took 6 years and nearly $4M all-in to complete
• How a wedding venue they never planned for now drives 50% of total revenue
• Why Ashley joined her county's planning commission, and what she sees developers get wrong every time
• The SBA loan structure that lets them avoid a $350K down payment
• What 80-90% occupancy actually looks like at a 5-room boutique lodge in a supply-constrained market

If you're serious about building a hospitality asset that creates real long-term wealth, this episode will show you what bootstrapped development actually looks like, and whether it's the right path for you.

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 Ashley LaRocque

Website: https://stayatjuniper.com

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

LinkedIn: https://www.linkedin.com/in/ashley-larocque-65397114/

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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In this episode, you'll discover how a single ultra-niche lodging unit can outperform a full hotel on cash-on-cash returns and what that signals for boutique investors paying attention.

A treehouse designer whose work has been featured in the New York Times, Architectural Digest, and HGTV joins us to break down the real numbers behind experiential lodging. Dustin Fighter has spent two decades building one-of-a-kind suspended structures, and his original pine cone treehouse, 60 feet in the air and $600K to build, is now generating over $200K per year at $850/night.

In this episode, you'll discover:

• Why a single $600K unit can deliver 30% cash-on-cash returns unleveraged, and whether it actually scales
• The 3 biggest obstacles that kill treehouse hospitality deals before they start: permitting, insurance, and bank financing
• How crowdfunding raised $600K from 700 investors and why equity outperformed revenue share
• The pre-booking capital strategy that lets you fund the build before you break ground
• Why banks won't touch tree-supported structures and what builders are doing instead
• How tariffs are driving up construction costs and forcing a pivot back to high-end custom builds

If you're interested in high ADR niches where limited supply drives outsized returns, don't skip the unit economics breakdown. The math speaks for itself.

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 Dustin Feider

Website: https://www.o2treehouse.com/

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

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 the most overlooked apartment deal in your market is already built, it's just flagged as a hotel?

In this episode, you'll discover how a valuation gap between hotels and multifamily creates forced equity of 40 to 50% before you change a single wall, and why most investors completely miss it.

A CEO who has completed over 30 hotel-to-apartment conversions across six states joins us to break down the exact strategy his firm has used to generate a 20% annualized return since inception. Ryan Sudeck and his team at Sage Investment Group turned an $8.5M distressed hotel into $18.9M in 19 months with a 38% annualized return and have since scaled the model to over 3,000 units and 500 investors.

In this episode, you'll discover:

• Why a hotel trading at a 12 cap automatically becomes more valuable the moment you convert it to residential, and how to calculate the forced equity before you buy
• The exact buy box Sage uses: room count, location signals, and the zoning step that most investors skip, which kills deals
• How to identify hotels in the "death spiral" before they hit the market and why Sage rarely buys on-market
• The invasive due diligence process they use to eliminate budget blowouts behind the walls
• Why the evergreen fund model outperforms syndications for this strategy, and how distributions work from day one
• The community impact case study in Tacoma that took a street responsible for 10% of Washington state murders to zero violent crime

If you're a hotel investor, a multifamily operator, or someone sitting on capital looking for a differentiated real estate strategy, this episode will change how you look at every distressed property you drive past. Don't miss the valuation math breakdown in the first ten minutes; it's genuinely one of the clearest arbitrage setups we've had on this show.

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 Ryan Sudeck

Website: http://sageinvestment.com

Email: ryan@sageinvestment.group

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

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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/

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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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

Visit the Hotel Investor Playbook Instagram

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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.

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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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.

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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Most hotel investors build the product first and spend years chasing an audience to fill it. This guest flipped the order entirely.

In this episode, Michael Russell sits down with a travel content creator who built a following of over a million people, then used years of staying in the world's best hotels to figure out exactly what makes a property worth sharing, and designed his own around it. That audience helped his first Bali hotel hit 80% occupancy in month one and pay back its full construction cost in 18 months, entirely self-funded. He now runs a 250-person company raising capital directly from that same audience to build boutique hotels across Bali and South Africa.

In this episode, you'll discover:

• How building an audience before building the asset flips the usual risk profile on a hotel investment
• What years of documenting five-star hotels taught him about what actually drives bookings
• Why he skipped OTAs almost entirely, and what that did to margins that run 40 to 60%
• How he's using fractional ownership to raise capital from his own community instead of institutional money
• What it took to scale from one Bali boutique hotel to hotels on two continents
• The one red flag he says every investor should check before wiring money into any hospitality fund

If you think an audience is just for influencers chasing likes, this episode will show you how far it can go as a substitute for a marketing budget, and where the real risk still lives.

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 Jake Snow:

Website is ventore.com

Their latest project is polarity.ventore.com 

Instagram: @ventoregroup and @mariefeandjakesnow

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.

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

Invest with Malama Capital

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Most investors think they're building a business, but they're actually building themselves a job. The truth? If you died tomorrow, your "business" would die with you.

A real estate investor who scaled from 80-hour weeks to just 4 hours per month reveals the exact automation framework that freed him—and how to apply it to any real estate asset, including hotels.

Mark Podolsky built a multi-million dollar land flipping operation, lost 50% of it in 2008, then rebuilt it into a passive income machine that runs without him. His approach isn't about working harder—it's about systematizing smarter.

In this episode, you'll discover:

• The 3-step system to automate ANY real estate process: Do it, Document it, Delegate it
• How to systemize direct-to-owner outreach for boutique hotels (instead of competing on broker listings)
• How to lock up deals with minimal capital and flip them to other investors (the arbitrage model)
• How to use inexpensive virtual assistants to handle repetitive acquisition tasks
• Why the biggest mistake new investors make isn't about the property—it's about their calendar
• The "brick your phone" strategy that helped Mark reclaim focus and family time

The real question isn't whether you can find deals. It's whether you can build a business that doesn't require you to do everything yourself. This episode shows you the framework to buy back your time while building real wealth.

About Mark Podolsky

Mark Podolsky, widely known as "The Land Geek," is a former investment banker turned land investor who has completed over 6,000 unique raw land transactions since 2001. As the author of Dirt Rich and host of The Art of Passive Income podcast, he teaches investors how to acquire distressed land for pennies on the dollar to generate passive income without the headaches of "tenants, toilets, and termites". Through his coaching platforms and automation software like GeekPay.io, Mark empowers entrepreneurs to build scalable, recession-resilient businesses that break the cycle of solo economic dependency.

Connect with Mark Podolsky

Connect with Mark on LinkedIn.

Follow Mark on Instagram or visit his Website.

Get Your FREE Copy of Dirt Rich (FOR A LIMITED TIME ONLY)

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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Most hotel owners think the only way to reduce OTA dependency is to throw more money at Facebook ads or hire expensive marketing agencies. But the real solution isn't more budget, it's leveraging what you already have: authentic stories and staff who actually care about the guest experience.

A hospitality marketing veteran who's advised VCs and built a 1.6 million social following reveals the direct booking playbook that independent hotels are using to reclaim revenue from OTAs. Scott Eddy has spoken at hundreds of conferences worldwide, doing the unexpected: giving away strategies that agencies charge thousands for.

In this episode, you'll discover:

• Why rolling out the red carpet for OTA guests (instead of alienating them) converts 30%+ into direct bookers
• The exact content categories that drive bookings and why shaky iPhone footage outperforms polished videos
• How to make your front desk staff into content superstars without hiring an expensive agency
• The one Instagram metric (hint: it's not followers) that actually predicts revenue
• Why "saves" and "comments" matter 10x more than likes for direct bookings
• The AI-discoverable scripting framework that's replacing traditional SEO for hotel discovery
• How long-form storytelling videos outperform short-form for brand discoverability (despite what Instagram tells you)
• The fatal mistake 80% of hotels make: posting beautiful property photos with promo text overlays that actively repel guests

If you're serious about reducing OTA dependency and building a direct booking engine without a massive marketing budget, this episode will provide the roadmap. Don't make the expensive mistake of outsourcing what your in-house team can do better.

About Scott Eddy

Scott Eddy is a globally recognized hospitality brand strategist and digital pioneer who transitioned from a decade in investment banking to founding the first and largest digital agency in Southeast Asia. With a combined following of over 1.2 million, Scott has hosted the travel series Video Globetrotter on Lifetime Television and is consistently ranked among the top 15 hospitality influencers in the world. He now travels full-time as a consultant and keynote speaker, helping hotel brands convert authentic storytelling into measurable ROI while championing the "independent advantage" through raw, human-centered digital engagement. A genuine citizen of the world, Scott lives entirely out of hotels and cruise ships, leveraging his experiences in 85+ countries and 120+ cruises to provide a unique "perpetual guest" perspective on the evolving travel landscape.

Connect with Scott Eddy

Connect with Scott on LinkedIn.

Follow Scott on Instagram or visit his 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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Most first-time motel buyers don't lose money on the purchase price. They lose it by underestimating CapEx, guessing on underwriting, and assuming they can "market" their way to higher occupancy. That's how people get smoked.

In this episode, you'll learn a simple, real-world way to sanity-check a value-add motel deal, including what "light reno" actually costs per key and which levers really move ADR.

My guest is Jordan Malara, an ex-Space Force engineer who went from managing short-term rentals to building a 60+ key hotel portfolio in just a few years. He's breaking down his first deal: a 27-key motel he bought for $2.45M with $500K in renovations, using SBA 7(a) and seller financing.

What you'll learn:

• Why "$20K per key" is a better starting point than your optimistic spreadsheet number
• The hidden CapEx that blows budgets: sprinklers, fire systems, laundry equipment, and code compliance work
• Jordan's 60% expense ratio sanity check, and why occupancy lifts are way harder than you think
• How he structured SBA 7(a) + seller financing in second position (and what made the seller say yes)
• The upgrades that paid back fastest: amenities, lobby experience, and staff, not bathrooms
• How he outsources revenue management and bookkeeping globally without bloating payroll

If you got value from this episode, share it with one friend who wants to buy a hotel. And if you want to talk through a deal, email me at info@hotelinvestorplaybook.com.

About Jordan

Jordan Malara is a former U.S. Space Force engineer turned hospitality entrepreneur who transitioned from managing satellite operations to building a high-performing portfolio of boutique hotels. Previously the Director of Operations for Renjoy, where he oversaw 180+ short-term rentals, Jordan co-founded Springs Hospitality to apply engineering-level systems to the revitalization of undervalued assets like the Adventure Inn Durango. He specializes in leveraging creative financing and narrative-driven branding to transform distressed properties into thriving community hubs, teaching investors how to scale from residential units to commercial hospitality with operational discipline.

Connect with Jordan

Connect with Jordan on LinkedIn.

Follow Jordan on Instagram or 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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Think you need hotel operations experience to invest in boutique hotels? That belief may be the only thing standing between you and building serious commercial real estate wealth.

In this episode, you'll discover how a Gulfstream pilot raised $1.5 million and became co-GP on a 130-room boutique hotel in Tennessee's Smoky Mountains - without managing a single employee or making a single bed.

A private jet captain who flies billionaires by day reveals his exact framework for partnering on commercial deals, vetting operators, and bringing value to the table through capital raising and deal analysis - not daily operations. When a USDA loan delay tested the partnership and threatened investor confidence, his communication strategy and the GP team's quick action turned a challenge into a case study on how strong partnerships weather any storm.

In this episode, you'll discover:

• How to add massive value as a hotel investor without operations experience (the skills that actually matter)
• Why 80% of Curt's $1.5M came from his existing network (not Instagram followers) and how to leverage yours 
• The critical questions to ask operating partners before co-signing on a major hotel acquisition 
• Why booking 3,000 additional room nights and raising ADR from $85 to $129 proves the value-add model works 
• The monthly communication framework that kept 100% of investors confident during an 8-month loan delay
• How GPs can inject capital at 10% interest to avoid diluting investor shares during unexpected shortfalls

If you're ready to stop letting "lack of operations experience" keep you out of hotel investing, this episode shows you exactly how to raise capital, structure partnerships, and protect investor relationships, even when deals don't go according to plan. This is proof that you can build commercial real estate wealth without being the operator

About Captain Curt

Curt Marker is a 15-year veteran pilot and the CEO of Captain Capital, a commercial real estate firm specializing in developing high-demand assets such as small-bay industrial flex space and boutique hotels. As a third-generation aviator and active private jet captain for billionaires, Curt translates elite "cockpit discipline," safety checklists, and high-level service into rigorous risk management for his real estate projects. He is widely recognized for his radical transparency and "skin in the game" philosophy, focusing on building long-term trust and resilient wealth for his investor partners. Curt also hosts The Captain Curt Show, where he educates professionals on transitioning tax-inefficient income into high-performing, cash-flowing commercial portfolios.

Connect with Captain Curt

Connect with Curt on LinkedIn.

Follow Curt on Instagram or 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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Most first-time hotel syndicators are already breaking the rules; they just don't know it yet. If you've ever taken money from friends and family without the right structure, you may have accidentally sold securities. And if you're paying someone just to raise capital? That's another violation waiting to happen.

In this episode, you'll learn exactly how to raise money for hotel deals without putting yourself or your investors at risk.

A securities attorney who's structured hundreds of capital raises and lost $1 million on her own failed fund shares the hard lessons that transformed how she builds partnerships today. Bethany LaFlam now co-owns a boutique resort in Belize and is building a luxury hospitality portfolio, all while helping Main Street operators avoid the costly legal mistakes she's seen kill deals.

In this episode, you'll discover:

• The #1 way sponsors accidentally break SEC rules (and how to stay compliant)
• Why 506B vs. 506C matters and how to choose the right structure for your raise
• The capital raiser compensation mistake that can get you investigated
• How to vet partners before you commit (including the exact questions to ask)
• Why "investor perks" like free hotel nights require careful legal structuring
• The mindset trap that kept her broke for years after a failed $50M fund

If you're planning to raise capital for a hotel deal, this episode could save you from a costly legal mistake or worse, an SEC investigation. Don't skip the compliance conversation.

About Bethany

Bethany LaFlam is a seasoned securities attorney, real estate investor, and Managing Partner at Premier Law Group, where she helps syndicators navigate complex SEC regulations to raise capital safely and effectively. With over two decades of legal experience, she champions the "Power of OPE" (Other People’s Everything), a strategic framework designed to help entrepreneurs scale their wealth and businesses without burnout. Bethany is also the author of the bestselling book The Power of OPE and the founder of the Conscious Capital Collective, a community dedicated to intentional wealth creation and luxury hospitality investing.

Connect with Bethany

Connect with Bethany on LinkedIn.

Follow Bethany on Instagram or visit their Website.

Join The Conscious Capital Collective

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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Stop treating your front desk like an expense; it's costing you hundreds of thousands in property value. The biggest mistake boutique hotel owners make isn't about the property itself. It's ignoring the untapped revenue sitting right at your check-in counter.

In this episode, you'll discover how to turn your front desk into a profit center that can add 5% to your bottom line and potentially $500,000 to your hotel's valuation.

A hospitality revenue expert who helped pioneer the car rental upsell model and has spent 25+ years turning frontline employees into sales engines joins us to break down the exact system. Joffrey Toffetti's company, Frontline Performance Group, works with properties from 20-room boutiques to major brands, and his approach has transformed front desk agents from minimum-wage employees into top earners making $50K+ through incentives alone.

In this episode, you'll discover:

• Why the "value mode vs. experience mode" mindset shift changes everything about guest interactions
• The 3-tier incentive structure that motivates front desk staff without blowing your budget
• How late checkout offers alone can generate $40,000+ annually (with almost zero cost)
• The conversion metrics and "URI" formula to track whether your upselling is actually working
• Why keyless entry and kiosks might be sabotaging your guest relationships and revenue
• How to spot upsell opportunities during due diligence before you even buy a property

If you're serious about maximizing hotel profitability, this episode will change how you think about staffing and guest experience. Don't leave five figures on the table every year because your front desk doesn't know how to sell.

About Geoffrey

Geoffrey Toffetti is the CEO of Frontline Performance Group (FPG), where he leverages over three decades of experience to transform hospitality frontline teams into powerful revenue generators. Rising from a resort valet to the C-suite, Geoffrey has guided FPG’s expansion to over 2,500 properties across 100+ countries, helping global brands like Hilton, Marriott, and Hyatt unlock over $2.3 billion in incremental revenue. Through FPG’s innovative IN-Gauge SaaS platform and a "service-based sales" philosophy, he empowers hourly staff to elevate the guest experience while driving significant bottom-line profitability without additional capital expenditure.

Connect with Geoffrey

Connect with Geoffrey on LinkedIn or 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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Why do so many people dream about buying a hotel but never actually close one?

In this episode, Michael sits down with Brian Resendez, CEO of SVN Northwest Hotel Advisors. 

Brian has been involved in hundreds of hotel transactions across the Pacific Northwest and brings rare insight into what separates buyers who close deals from buyers who stall out.

You will learn:
 • The real reasons most buyers never get their first deal
 • How successful investors overcome fear, uncertainty, and inexperience
 • Why third-party management opens the door to bigger and better hotels
 • What it takes to build the right team before you buy
 • Why larger assets often perform better and are easier to operate

If you want a real look into how hotel investing actually works, this episode will give you the perspective and confidence to keep going.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Brian

Brian Resendez is the Senior Vice President of Hotels at SVN | Bluestone & Hockley, specializing in hospitality brokerage and land acquisition across Oregon, Washington, and Idaho. With a diverse background spanning hotel operations for brands like Westin and Doubletree, commercial finance, and real estate, he offers a holistic perspective on complex transactions that goes far beyond typical brokerage. Brian recently closed a record-breaking 26 hotels in a single year, pioneering innovative hotel-to-housing conversions through Project TurnKey and actively advocating for diverse ownership as a Board Member of the Latino Hotel Association. He is dedicated to serving owner-operators in the $2 million to $20 million asset class, focusing on long-term relationships and operational fundamentals over simple transaction volume.

Connect with Brian

Connect with Brian on LinkedIn or by email at brian.resedez@svn.com.

Visit their website: https://www.nwhotelinvestor.com/

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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Boutique hotel investors often lose money in the same place: they renovate what’s visible, and ignore what actually drives guest behavior.

In this episode, we talk about design as a business tool, not a decoration budget. The goal is simple: create a guest experience that feels intentional, sells itself, and supports your NOI, even when you’re operating without brand-level resources.
My guest is Scott LaMont, CEO of EDSA, a globally recognized design and planning firm. Scott and his team work on hospitality projects worldwide, from master planning new destinations to repositioning existing resorts.

You’ll hear:

• How to “program” spaces so they earn money at different times of day
• What to look for during acquisition that signals hidden upside
• Why the lobby is not a pass-through, it’s a profit center
• How local partnerships create authenticity without big construction costs
• The infrastructure investments (water, resiliency) owners regret skipping
• A practical way to use guest reviews as free due diligence

If you’re graduating from Airbnb to your first hotel deal, this episode will help you avoid rookie capex mistakes and make design decisions that actually translate to revenue. Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Scott

Scott LaMont is the CEO and Principal of EDSA, a globally recognized planning and landscape architecture firm where he has spent nearly three decades shaping award-winning destinations for brands like Four Seasons and The Ritz-Carlton. An expert in “deconstructed hospitality” and nature-focused design, Scott combines environmental stewardship with pragmatic business planning to drive long-term value and ROI for developers. He leads with a collaborative, human-centered philosophy that integrates emerging technologies like AI to create authentic, immersive guest experiences that connect people with place.

Connect with Scott on Instagram or LinkedIn.

Visit their website: https://www.edsaplan.com 

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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Is now a terrible time to buy a hotel, or the best buying window you will get this decade?

In this episode, Michael sits down with Suraj Bhakta, CEO of NewGen Advisory, a national hotel brokerage that has closed deals in 44 states. Suraj explains what he is actually seeing in today’s market, from the SBA shutdown fallout to the quiet distress building under the surface.

In this conversation, you will learn:

• Why are the 2021–2022 performance numbers misleading so many sellers and buyers
• Where distress is most likely to show up first, and how to spot it before the crowd
• How to think about value-add when required upgrades do not pencil on the back end
• Concrete steps buyers should take this week if they want to be ready when deals crack

If you are serious about buying hotels in this environment, this episode will help you see what is really happening behind the scenes and how to move with more confidence.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Suraj

Suraj Bhakta is the CEO of NewGen Advisory and Chief Legal Counsel for NewGen Worldwide, where he leads a national brokerage team that has executed hospitality transactions across 44 states. Drawing on over two decades of experience as both a commercial real estate attorney and a lifelong hotelier, Suraj has advised on more than $850 million in acquisitions and facilitated nearly $500 million in capital raises. He specializes in guiding investors through the full property lifecycle, offering expert counsel on complex market challenges ranging from financing and Property Improvement Plans (PIPs) to creative adaptive reuse projects.

Connect with Suraj

Email: suraj.bhakta@newgenadv.com

Phone: +1.602.648.2702

Website: https://newgenadv.com/

LinkedIn: Suraj Bhakta

Instagram: @newgenadvisory

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Most people walk past the ugly deal. That's exactly why the ugly deal is where the money is.

In this episode, Michael Russell sits in the hot seat as a guest on the Lights On Podcast, sharing the unfiltered story behind how he acquired a rundown one-star motel in Maui during COVID and repositioned it into the number one small hostel in North America, growing annual revenue from $500K to $2.4 million in just a few years.

Co-founder of Howzit Hostels and Malama Capital, Michael has built a hospitality portfolio by finding value where others aren't looking, starting with single-family homes in the post-recession market, scaling through short-term rentals, and eventually buying a motel no one else wanted.

In this episode, you'll discover:

• Why Michael paid $800K for a property most investors would have ignored, and how seller financing made it possible
• The budgeting mistake that nearly destroyed their returns (and why going 40-50% over budget is more common than anyone admits)
• How the Lahaina fires wiped out short-term rental income overnight and what it taught him about cash reserves the hard way
• The real math on OTAs vs. direct bookings that most independent operators get wrong
• Why Michael started The Hotel Investor Playbook with zero interest in monetizing it, and what that means for the conversations he's willing to have

If you're serious about finding your first hotel deal or scaling what you've already built, this episode will save you from some expensive assumptions. The unglamorous path is usually the most profitable one.

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 Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Click here to start your free 7-day trial of the AI for CRE Collective.

Most boutique hotel investors are running lean. No analyst team. No data department. No six-figure tech budget. Yet the demands of buying and operating hotels keep getting heavier.

In this episode, I sit down with Jake Heller, founder of the AI for CRE Collective, to break down the most effective AI tools that give small operators the firepower of a full investment team without hiring more staff or burning more hours.

We workshop real tools you can start using today to:

• Research any hotel market in minutes
• Underwrite deals 5 to 10 times faster
• Build pro-grade investor decks and OMs
• Create renovation concepts and renderings
• Cut legal costs with AI-assisted contract review
• Streamline asset management and portfolio reporting
• Automate day-to-day admin and communication

1. Claude (Deep Research) – Market feasibility, multi-source synthesis
2. Perplexity (Market Intel) – Accurate analytical research with citations
3. Shortcut AI (Underwriting) – Flexible financial modeling inside Excel
4. Google Gemini (Nano Banana Image & Video Generation) – Property renderings, façade upgrades, interior redesigns, branding, teaser videos
5. Wilson AI (Legal & Due Diligence) – Contract review, redlines, title exceptions
6. Gamma (Decks & OMs) – Investor decks, offering memorandums, pitch materials
7. Wspr Flow (Voice-to-Text & Admin) – Ultra-fast transcription, notes, emails, and communication

Whether you’re trying to scale your hospitality business, underwrite more deals, or operate your hotel with fewer people, these tools will change the way you work.

If you want to buy and operate hotels without a big team or a ton of time, this episode is your new playbook.

Get One Week Free Membership to Jake’s AI for CRE Collective

If you want help implementing everything we discuss in this episode - the prompts, the workflows, the tools, the systems - Jake’s community is the best place to start. 

Listeners of The Hotel Investor Playbook can get full access for FREE.

Click here to start your free 7-day trial of the AI for CRE Collective.

About Jake

Jake Heller is a third-generation homebuilder and entrepreneur who co-founded the AI for CRE Collective, a central hub where AI and technology meet real estate. As an expert focused on practical, implementation-oriented solutions in AI in Commercial Real Estate, he built this 400+ member community to provide battle-tested workflows, automation templates, and a database of 300+ vetted AI tools for professionals. Drawing on his experience in development and consulting, including cofounding JDJ Consulting Group, Jake specializes in helping CRE firms and individuals scale and streamline processes to accelerate deal speed across critical tasks such as underwriting and deal analysis.

Connect with Jake

Website: https://aiforcrecollective.com/

LinkedIn: https://www.linkedin.com/in/jakeheller1/

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

YouTube: https://www.youtube.com/@aiforcrecollective

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Turning an international hospitality dream into reality sounds exciting, until you’re standing on a swampy patch of land in Belize, wondering how many years it will take to shape it into something guests will love.

That’s where today’s guest, Odis Martin, began. He and his wife spent nearly a decade transforming a remote island into Sindiri on the Reef, a private eco lodge built without outside investors and rebuilt multiple times after hurricanes. 

Odis and his wife went from small US multifamily to hand digging a swampy island, navigating Belize regulations, rebuilding after hurricanes, and creating a one of a kind off grid destination.

In this episode, you’ll learn:

• How a school project turned into a 10-year international hospitality roadmap
• The real cost and complexity of off-grid development on an island
• What actually makes buying in Belize approachable for US investors

This episode gives you a realistic look at what it really takes to turn an overseas hospitality dream into a real, functioning business.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way. 

About Odis

Odis Martin is the owner and captain of Cindiri On The Reef, a Garifuna family-owned private island resort located off the coast of Dangriga, Belize. Alongside his wife, Odis transformed their graduate school thesis into a real-world venture, hand-building the resort from raw land with local Maya and Garifuna craftsmanship and a deep commitment to sustainability. Before launching Cindiri, the couple built a 20-door real estate portfolio in California, which helped self-fund the project without outside investors. Today, Cindiri On The Reef stands as a model for off-grid, eco-luxury hospitality offering reef-to-table dining, immersive ocean experiences, and a masterclass in independent, purpose-driven resort development.

Connect with Odis

Website: https://cindiri.com/

LinkedIn: https://www.linkedin.com/company/54356667

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

Facebook: https://www.facebook.com/cindirionthereef

YouTube: https://www.youtube.com/@cindirionthereef

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Most hotel investors struggle to get brokers to take them seriously. The result is the same handful of buyers getting the first look at every good deal while everyone else fights over leftovers.

In this episode, Michael sits down with Hunter Johnson, President of Investment Sales at US Hotel Advisors, to break down how brokers actually decide who gets deal flow. 

Hunter shares what he looks for in a real buyer, what turns him off immediately, and the simple behaviors that make brokers want to send you deals before they ever hit the market.

You’ll learn:

• What separates a “real buyer” from a time-waster
• The signals that instantly increase your credibility
• How to build relationships that get you called first
• Creative ways to structure deals when traditional debt won’t work
• What lenders want to see from first-time hotel buyers
• When SBA loans make sense and when they don’t

If you want more brokers sending you legitimate opportunities, this episode shows you exactly how to get on their radar and stay there.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Hunter

Hunter Johnson is the President of Investment Sales at US Hotel Advisors, a hospitality investment-banking firm specializing in the sourcing and structuring of debt, equity, and investment-sales transactions for hotel properties across the U.S.. Drawing on a background that includes commercial real estate, lending, finance, and property insurance, Hunter is uniquely positioned to advise clients on complex capital structures and transaction execution. His firm excels at securing non-recourse financing and raising sophisticated mezzanine or preferred equity, often for assets facing challenging circumstances such as low debt yields or rebrandings. Hunter strives to create trusted and lasting industry relationships while utilizing a competitive bid process to advise on the sale of various assets, including boutique properties, to yield above-market sales prices.

Connect with Hunter

https://ushoteladvisors.com/

https://www.linkedin.com/company/us-hotel-advisors/

https://www.linkedin.com/in/hunter-johnson-2778b120/

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Want to know what it’s like to go from short-term rentals to owning boutique hotels while still maintaining a healthy relationship?

This week on the Hotel Investor Playbook, Michael Russell sits down with Mitch Ehly and Katie Wanzer, the husband-and-wife duo behind Fresh Coast Motel and Spruce & Shore Motel in Door County, Wisconsin.

They share how they scaled from Airbnbs to a full-fledged hospitality brand, revived two historic motels, and used automation to stay profitable without losing the guest touch.

You’ll learn how they:

• Transitioned from STRs to hotels (and what changed operationally)
• Revived historic properties into modern boutique experiences
• Turned self-check-in into a high-touch guest experience using video personalization
• Balanced business, marriage, and mindset while scaling fast

If you’ve ever dreamed of turning your short-term rental business into something bigger, this is the episode to study.

About Mitch & Katie

Mitch and Katie are the husband-and-wife team behind Fresh Coast Motel and Spruce & Shore Motel, two boutique properties redefining the modern Door County getaway. Drawing on Mitch’s background in hospitality technology and leadership, and Katie’s creative eye for design and guest experience, the pair have transformed classic roadside motels into stylish, high-end retreats that blend historic charm with modern comfort. Their approach embraces self-check-in technology, thoughtful renovations, and authentic local storytelling to create spaces that feel both elevated and effortless. Together, they’re shaping a new wave of boutique hospitality in Wisconsin’s most beloved coastal towns.

Connect with Mitch & Katie

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

Websites

https://freshcoastmotel.com

https://therefreshcollection.com/

https://spruceandshoremotel.com/

Instagram

https://instagram.com/mitchehly

https://www.instagram.com/spruceandshoremotel

https://www.instagram.com/freshcoastmotel                   

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Looking for hotel technology that can actually increase profit and reduce expenses without hiring an IT department?

This week on the Hotel Investor Playbook, Michael Russell sits down with Sue Graves, founder of Experience Alive, who has spent over 30 years in hospitality and now helps hotel owners implement practical, affordable tech solutions that make a real financial impact.

In this episode, you’ll discover several technology use cases you can implement today, including:

• Offload up to 50% of front desk calls through conversational AI
• Use delivery robots to run leaner night shifts and boost service speed
• Track linen and towels with RFID to cut losses and eliminate manual counts
• Build a sustainability story that supports better refinancing terms
• Plus more!

Whether you own a 50-room boutique hotel or manage a national brand, Sue shows how to make technology your competitive edge.

About Sue

Sue Graves is the Founder and CEO of Experience Alive, a hospitality technology consultancy helping hotels, restaurants, and convention centers modernize operations through AI-driven solutions, robotics, and guest personalization tools. With over 30 years of leadership experience at Marriott International and the Greater Columbus Convention Center, Sue brings a deep operational understanding to innovation in hospitality. As the founding chair of the Ohio Hotel & Lodging Association’s Innovation & Technology Committee, she has championed initiatives that boost efficiency, guest satisfaction, and staff retention across the industry. A recognized voice on the future of tech in hospitality, Sue continues to bridge the gap between emerging technologies and real-world hospitality challenges, empowering teams to deliver more human-centered, high-performing experiences.

Connect with Sue

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

Website: http://Experiencealive.com

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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Ever dreamed of quitting your six-figure job to build real wealth through hotels? This episode shows you what it actually takes.

Tim Ensmann, founder of the T.C. Hotel Fund, shares how he went from tech sales to owning a multi-million-dollar boutique hotel portfolio in under five years. He reveals the sacrifices, systems, and strategies behind turning a $1.5M property into a $4.5M success story. He then shares how you can follow the same path without losing your sanity.

You’ll learn:

• The real moment he knew he couldn’t stay in corporate anymore
• How he used short-term rentals to bridge the gap from W2 to full-time investor
• What it costs (financially and emotionally) to leave a secure job for entrepreneurship
• How to identify the right first project for your goals

This is a step-by-step blueprint from someone who’s actually done what so many people dream of.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Tim

Tim Ensmann is the founder and managing partner of Boutique Hotel Fund, an investment platform that acquires and repositions boutique hotels across the United States. With a background in corporate sales and strategy, Tim transitioned from tech leadership roles into hospitality investing, where he now helps accredited investors build wealth through experiential real estate. His firm focuses on transforming underperforming properties into design-driven, story-led destinations that deliver both emotional impact and strong financial returns. Through his content and education platforms, Tim is redefining what modern hotel ownership looks like for a new generation of investors.

Connect with Tim

Email: tim@boutiquehotelfund.com

LinkedIn: www.linkedin.com/in/tim-ensmann/

Website: boutiquehotelfund.com/

Instagram: @tim_ensmann and @boutiquehotelguy

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

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Ever wonder where the money actually goes in a hotel deal?
In this episode, Michael Russell breaks down real estate syndications in plain English. How investors and operators really get paid, what fees are fair, and how to structure deals that build long-term trust.
Whether you’re looking to raise capital for your first project or invest passively, this is the playbook for understanding the math behind every syndication.
You’ll learn:

• The simple breakdown between LPs and GPs and how each gets paid
• How preferred returns, profit splits, and waterfalls actually work
• The most overlooked risk in syndications (and how to avoid it)
• How to structure deals that attract repeat investors
• Why clarity always beats complexity when raising capital

If you’ve ever wanted to peek behind the curtain of a hotel syndication, this episode will make everything finally click. Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

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Email Us at info@hotelinvestorplaybook.com

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When most people say they want to buy a hotel, it’s just talk.

Jacobo Hernandez sold his entire $10M short-term rental portfolio, packed his car, and hit the road for 90 days to find one.

He toured 35 hotels, underwrote 2,000 deals, and slept in random motels across the U.S. before discovering a hidden gem, a 59-room hotel on 10 acres in Eureka Springs, Arkansas, for just $1.2 million.

Now he’s turning it into Forest Springs Hotel & Spa, a wellness-focused retreat with saunas, cold plunges, and outdoor cinemas funded by investors who believed in his vision.

In this episode, you’ll learn:

• The exact framework he used to identify hot markets and good deals
• How storytelling and video marketing helped him raise $2.5M+ in capital in weeks
• Why focusing on unique, experiential assets can help investors stand out and command higher ADRs

This episode is super interesting and shows what can happen when you go all in!

About Jacobo

Jacobo Hernandez is the founder and CEO of FreedomVest Capital and managing partner at The Vesta Group, where he specializes in transforming undervalued real estate into high-performing boutique hotels and short-term rentals. With expertise in acquisitions, revenue management, and digital marketing, Jacobo has built multimillion-dollar portfolios that merge design-driven hospitality with investor-focused returns. He’s also the author of Short-Term Rental Secrets, a guide to scaling and exiting rental portfolios through data, SEO, and systems. Passionate about education and impact, Jacobo now teaches entrepreneurs how to build scalable hospitality businesses that generate both financial freedom and exceptional guest experiences.

Connect with Jacobo

Website: https://thespringsretreat.space/

LinkedIn: https://www.linkedin.com/in/jacobo-hernandez-747299128/

Instagram: @_jacobohernandez_

Tiktok: @jacobohernandez_official

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Email Us at info@hotelinvestorplaybook.com

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We’ve all dreamt of quitting our bland corporate jobs to buy a hotel in Costa Rica… well, today’s guest did that.

After leaving a private equity career in San Francisco, Bill Graf traded suits for surf towns and founded Onda, a hospitality brand in Costa Rica that blends the style of a boutique hotel with the social energy of a hostel.

You’ll learn:

• How to uncover hidden opportunities in small hotels that big players ignore
• What U.S. investors should know about buying real estate in Costa Rica
• His unique strategy for keeping his properties full year-round

This episode is a blueprint for spotting opportunities where others see risk… and will certainly have you daydreaming by the end of it!

Follow along with The Hotel Investor Playbook to discover how to invest in hospitality assets the right way.

About Bill

William “Bill” Graf is the founder and CEO of ONDA, a hospitality collective in Costa Rica that blends boutique hotel comforts with the social energy of a hostel. A former investment banker and private equity professional, Bill left Wall Street in 2016 to travel the world, visiting over 50 countries and experiencing firsthand the challenges of inconsistent accommodations. Inspired to create a better model, he launched ONDA to deliver reliable, community-driven stays in lifestyle destinations where major hotel brands won’t go. Today, Bill is building ONDA into a global hospitality brand focused on culture, connection, and transformational guest experiences.

Connect with Bill

Website: www.stayonda.com

LinkedIn: linkedin.com/in/williamgraf

Instagram: @billygoat_graf and  @findyouronda

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Email Us at info@hotelinvestorplaybook.com

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The hotel industry is changing: costs are rising, AI is here, and investors are getting more selective.

This week on the Hotel Investor Playbook, we sat down with Bob Rauch, better known as The Hotel Guru. From starting out as a dishwasher to building and selling a 20-hotel management company, then launching Brick Hospitality and managing nearly 1,000 rooms, Bob has seen it all.

In this episode, you’ll learn:

• How to spot hot markets (and avoid the ones that eat your profits)
• The truth about using robots and AI inside hotels
• The 4 core skills Bob believes every investor must master

Bob has 45+ years in the trenches, and he’s sharing real stories, wins, and lessons that can change how you invest.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Bob

Robert A. Rauch, CHA, widely known as “The Hotel Guru,” is a nationally recognized hotelier, consultant, and strategist with over four decades of experience in the hospitality industry. He is the Chairman of Brick Hospitality, Managing Partner of the Hilton Garden Inn and Homewood Suites San Diego/Del Mar, and founder of Hotel Guru. This consulting firm advises hotel owners and investors on acquisitions, operations, finance, and marketing. A Certified Hotel Administrator, Rauch has also served as a faculty associate at Arizona State University, authored the industry newsletter Hospitality Innsights, and contributed regularly to leading hospitality publications. Through his leadership, market forecasts, and hands-on advisory, he has helped shape the future of hotel investment and management while mentoring the next generation of hospitality professionals.

Bob's Book

The Hotel Guru’s Journey: A Guide to Excellence in the Hotel Industry, launching October 2025, available on Amazon.

Connect with Bob

Website: hotelguru.com

LinkedIn: www.linkedin.com/in/robertrauch

X: x.com/truehotelguru

Facebook: facebook.com/hotelguru

Email: rauch.ra@gmail.com

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Email Us at info@hotelinvestorplaybook.com

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In this episode, you'll learn how to diagnose whether your property is actually a candidate for wellness positioning, and if it is, how to implement it in a way that lifts ADR without blowing out your expense line.

A hospitality strategist who spent 20 years in hotel sales and development before building a consulting practice around wellness revenue joins us to share the playbook she's used across independent properties worldwide. Emily Johnson's approach has helped properties drive occupancy lifts and ADR increases with near-zero incremental cost by tapping into what they already have.

In this episode, you'll discover:

• The 3 questions every owner should ask before spending a dollar on wellness
• Why a Thailand beachfront property was getting crushed on rate until one strategy drove a 15% occupancy lift and $40 ADR increase in a single quarter
• The low-cost local partnership model that turns empty meeting rooms into revenue
• Why most "wellness hotels" are faking it and how guests always find out
• The pre-arrival touchpoint that nearly every hotel is missing is costing real revenue
• How a mountain property with no unique story repositioned around one experiential amenity and sold out glass-ceiling cabins at $1,000 a night

If you're an independent operator trying to compete without throwing capital at the problem, this episode will show you where to start.

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 Emily Johnson

Website: https://www.elevatehospitalitycollective.com 

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

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Email Us at info@hotelinvestorplaybook.com

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Where is the hotel market headed in 2026, and how can investors succeed in a challenging environment?

This week on the Hotel Investor Playbook, we sat down with Jan Freitag, National Director of Hospitality Analytics at CoStar. With over 30 years of experience analyzing hotel performance data, Jan is one of the most respected voices in the industry.

Here’s what you’ll learn:

• How to use data and analytics to spot opportunities others overlook
• Why conviction and strong operations can outperform market averages
• How investors can protect margins as costs continue to rise
• Why the sub-$10M space stays active and how to play in it wisely

If you want to understand how smart investors can win even in a challenging market, this is the episode you need.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Jan

Jan Freitag is the National Director of Hospitality Analytics at CoStar Group, where he provides industry-leading insights on hotel performance, market trends, and investment opportunities. With nearly two decades at STR as Senior Vice President of Lodging Insights, Jan has become one of the most trusted voices in hospitality analytics, frequently cited by outlets like The Wall Street Journal, New York Times, Bloomberg, and CNBC. His expertise helps investors, owners, and operators make data-driven decisions across acquisitions, funding, marketing, and operations. Jan is also a sought-after speaker and thought leader, known for translating complex data into actionable strategies for hospitality success.

Connect with Jan

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

Podcast: Tell Me More: A Hospitality Data Podcast

Jan's non-CoStar data set: I-92/APIS data https://lnkd.in/g-faxadX

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Email Us at info@hotelinvestorplaybook.com

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The most powerful part of a hotel stay isn’t the design or the amenities, it’s the feeling guests take home.

That’s the philosophy of Bashar Wali, one of the most candid and creative voices in hospitality, who's spent 30+ years building, operating, and reinventing hotels around the world.

In this episode of the Hotel Investor Playbook, Bashar shares:

• Why “give-a-shit-ability” beats corporate playbooks
• The power of emotional intelligence in hotel teams
• The biggest mistakes first-time owners make
• The difference between the three types of hotel deals (core, value-add, and opportunistic)

Bashar doesn’t hold back. Whether you’re an operator, investor, or aspiring hotelier, this conversation will reshape how you think about hospitality.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Bashar

Bashar Wali is a seasoned hotelier, entrepreneur, and the founder of This Assembly and Practice Hospitality, with over 30 years of experience leading and scaling some of the industry’s most innovative hotel brands. In this episode, Bashar shares his playbook across acquisitions, funding, marketing, and operations, revealing how emotional intelligence, design, and culture are just as critical as deal structures and NOI. From building authentic guest loyalty without points, to structuring creative capital stacks, to “making the magic” in operations, his insights are both tactical and timeless. Whether you’re a first-time hotel investor or looking to scale your portfolio, this conversation will give you actionable lessons to apply in your own ventures.

Connect with Bashar

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

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

Website: https://www.thisassembly.com

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Email Us at info@hotelinvestorplaybook.com

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How do you turn a struggling hotel into a profitable asset?

This week on the Hotel Investor Playbook, we sit down with Naveed Khan, co-founder of London Rock Partners, a hotel management and advisory firm that oversees everything from branded hotels like Holiday Inn to boutique independents and even a 650-bed hostel in London.

In this episode, you’ll learn:

• Why the first step in turning around a hotel always starts with people, not P&Ls
• The advantages (and risks) of branded vs. independent hotels for investors
• How management companies can become a true partner in value creation
• Why tech and automation are reshaping hospitality operations
• Tactical advice for first-time hotel investors on keeping it simple

If you want to understand how the right management partnership can transform your hotel investment, this episode is a must-listen.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Naveed

Naveed Khan is the Chief Operating Officer of London Rock Partners, a leading hospitality asset and hotel management firm based in the UK. With a career spanning revenue management, commercial strategy, and full-scale hotel operations, he has led both branded and boutique properties through transformation and growth. Naveed is known for his people-first leadership, tech-driven operational strategies, and ability to maximize asset performance for owners and investors. His journey from revenue manager to COO reflects both resilience and a deep commitment to reshaping the future of hospitality.

Connect with Naveed

Website: https://www.londonrockpartners.com/

LinkedIn: https://www.linkedin.com/in/naveed-khan-580ba179/

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

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

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Few people have left a mark on hospitality like Richard Kessler.

He started his hospitality career by helping scale Days Inn into a household name as the early CEO

Then he founded the Kessler Collection, one of the leading boutique hotel portfolios in the U.S., which ultimately helped launch Marriott’s Autograph Collection.

In this episode, Richard shares the biggest lessons from his 50-year career, including:

 • How to lead through downturns and find opportunity in distress
 • Why reputation as an operator attracts financing and partners
 • The role of vision, teamwork, and conviction in building lasting brands
 • Why his mother’s advice, “Don’t take the elevator, take the stairs”, shaped his approach to success

This is a rare chance to learn directly from one of hospitality’s true icons.

About Richard

Richard C. Kessler is a visionary hotelier and entrepreneur with more than 50 years of experience in hospitality, best known as Chairman and CEO of The Kessler Collection. He previously served as President and Chairman of Days Inns of America and later pioneered the boutique luxury movement, restoring historic properties like Casa Monica Resort, The Mansion on Forsyth Park, and Savannah’s Plant Riverside District. Kessler co-launched Marriott’s Autograph Collection, becoming its largest U.S. franchise operator, and remains deeply involved in the design and development of each property. Beyond hospitality, he is a committed philanthropist, supporting faith-based initiatives, education, and the arts through scholarships, cultural collections, and community projects.

Connect with Richard

LinkedIn: Richard Kessler - Chairman and CEO at The Kessler Collection | LinkedIn

Website: The Kessler Collection

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Email Us at info@hotelinvestorplaybook.com

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What if your first hotel deal could be funded almost entirely through Instagram?

This week’s guest, Soli Cayetano AKA lattes.and.leases on Instagram, went from barista to building a $13M real estate portfolio in just four years. After exiting her residential investing business, she turned to hospitality and now co-owns a 13-key boutique wellness hotel in Palm Springs that’s already been featured in Forbes, Vogue, and Travel & Leisure.

In this episode, you’ll learn:

• How Soli raised $2.5M in 60 days through her Instagram audience
• Why documenting your journey builds trust with investors
• The key differences between residential and hospitality investing
• Why losing money can be the most valuable education

If you want proof that bold moves, social media, and persistence can change your life, this episode will give it to you.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Soli:

Soli Cayetano is a real estate investor, educator, and boutique hotel owner who has scaled from buying her first out-of-state rental at 23 to building a multimillion-dollar portfolio and co-owning Terra Palm Springs, a 13-room wellness boutique hotel featured in Travel + Leisure, Forbes, and Vogue. Through her platform Lattes & Leases, she empowers new and aspiring investors with the tools, courses, and community to confidently analyze deals, raise capital, and manage properties. Soli is passionate about creating design-forward, thoughtful hospitality brands while making real estate investing approachable, fun, and impactful.

Contact Soli:

Instagram: @lattes.and.leases  & @terrapalmsprings

Website: https://www.terrapalmsprings.com/

LinkedIn: Soli Cayetano - Wellness Hotel Owner & Marketing Strategist 

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Email Us at info@hotelinvestorplaybook.com

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Most hotel investors default to syndication — raising capital from dozens of limited partners and layering in complex waterfalls. But what if there’s a smarter, simpler path?

This week’s guest, Brandon Gore, is building The Outlier Hotel, a 10-cabin luxury retreat in Arkansas designed to last 100 years. Instead of chasing the traditional syndication model, he’s structuring the project as a joint venture — lowering pressure, creating strong cash flow, and unlocking tax advantages that limited partners usually can’t access.

In this episode, we dig into:

• How intuition plus data shaped Brandon’s decision to buy land on a hunch
  
  
• The financial model behind The Outlier (ADR, occupancy, and NOI)
  
  
• Why joint ventures can sometimes outperform syndications
  
  
• How accelerated depreciation makes this deal especially compelling
  
  
• What it takes to build hotels that align with your values and your legacy

This is part business case study, part lesson in trusting your instincts — and a rare look at how different deal structures can change the game for hospitality investors.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Brandon:

Brandon Gore is a designer, builder, and entrepreneur known for blending craftsmanship with innovation. He is the founder of Gore Design Co., Hard Goods, the Concrete Design School, and EarthForm Rammed Earth, where he has pioneered sustainable building with concrete and rammed-earth construction. Today, he is developing The Outlier Hotel in Eureka Springs, Arkansas—a boutique property that reflects his vision for timeless design and lasting architecture. Brandon has also shared his expertise as a TEDx speaker, podcast host, and judge on the design competition show Framework.

Connect with Brandon:

Instagram:@outlierhotel & @hardgoodsco

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

Website: Gore Design Co. & Brandon Gore

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Email Us at info@hotelinvestorplaybook.com

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Think great marketing is only for big hotels with big budgets? Think again.

In this episode, we talk with Steph Weber, a marketing and branding expert who helps boutique hotel and STR owners drive direct bookings. She breaks down how she finds her audience, tells a compelling brand story, and uses limited resources to drive big results.

You’ll learn:

• How to identify your property’s unique selling points
• Simple marketing strategies that work for small hotels and inns
• Why guest experience is your most powerful marketing tool

The mindset shift from “just filling rooms” to building a brand
If you want your property to stand out in a crowded market, this conversation will show you how to do it without wasting money.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Steph

Steph Weber is a branding strategist, marketing expert, and founder of The Weber Co., where she helps short-term rental owners, boutique hotels, and micro-resorts build memorable brands that drive direct bookings. With over a decade of experience and a track record of helping 100+ businesses scale to six and seven figures, Steph blends creative storytelling with data-driven strategies to increase guest loyalty and revenue. She also owns Cabins on the Cumberland, a 12-cabin, 9-acre riverfront micro-resort in Kentucky, giving her a unique, real-world perspective on what it takes to stand out in a competitive hospitality market. Through her agency, podcast, and own hosting experience, Steph empowers property owners to position their brands for higher rates, repeat guests, and long-term success.

Connect with Steph

Instagram: @stephnweber, @cabinsonthecumberland & @theweberco

Websites: www.theweberco.com and www.cabinsonthecumberland.com

LinkedIn: www.linkedin.com/in/stephweberbrandcoach

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

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Think you need a perfect plan to start investing in hospitality? Think again.

In this episode, we sit down with Jonathan Mueller, an everyday investor who went from zero experience and a failed multifamily deal to buying a $250K roadside motel and building a growing hospitality portfolio. He didn’t have a background in hotels, didn’t have much of a strategy, and still made it work through pure action, problem-solving, and a willingness to pivot.

You’ll learn:

• Why taking action beats waiting for the “perfect” plan
• How Jonathan raised $300K in 72 hours to close his RV park deal
• The pros and cons of buying motels vs RV parks as a beginner
• What to look for in seller financing and SBA loan terms
• Why chasing “shiny objects” can actually help you find your path

Whether you’re just getting started or stuck overthinking your first deal, this episode shows how to take imperfect action and learn as you go.

Follow and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Jonathan:

Jonathan Mueller is a real estate investor and hospitality entrepreneur transforming neglected motels and campgrounds into vibrant community destinations. Alongside his family, he owns and operates two renovated motels and a 70-acre RV park, Camp Forest Haven, blending hands-on renovation with a guest-first approach. His journey from spotting opportunities on a casual drive to scaling multiple hospitality assets offers actionable lessons in sweat equity, creative repositioning, and building community-focused spaces that truly stand out.

Connect with Jonathan:

Website: https://campforesthaven.com/

Instagram: @mister_mox  and @camp.forest.haven

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Email Us at info@hotelinvestorplaybook.com

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Is your marketing helping your hotel or just draining your budget?

In this episode, we sit down with Anthony Chiaravallo, founder of Vallo Media, who has managed over $100M in ad spend for brands like Nike, Resorts World, and boutique hotels across the country. Whether you're trying to fill beds or scale a brand, Anthony breaks down how to think about hotel marketing in a way that actually drives bookings.

You’ll learn:

• How to build a full-funnel strategy that drives real bookings
• What makes a great marketing agency vs a waste of money
• How to know if your hotel is ready for paid ads
• The minimum spend and timeline you need to see real results
• The path to 3x Return On Ad Spend 

If you’ve ever felt overwhelmed by digital marketing, this episode simplifies what matters.

Review and share the Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Anthony:

Anthony Chiaravallo is the founder and CEO of Vallo Media, a performance marketing agency that has overseen more than $100 million in paid media spend for clients ranging from Fortune 500 brands to hospitality startups. With over 16 years of experience in integrated media, Anthony specializes in data-driven strategies across paid social, search, programmatic, and influencer marketing. He’s a member of the Forbes Agency Council and a recognized thought leader featured in outlets like Forbes, USA Today, and The Wall Street Journal. His work focuses on helping brands scale revenue through measurable, omnichannel marketing.

Connect with Anthony:

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

Website: https://www.vallomedia.com/

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Email Us at info@hotelinvestorplaybook.com

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Ever wondered how people raise millions to buy real estate without using their own money?

In this episode, Desiree Doubrox breaks down the world of syndication and how she built an eight-figure fund while empowering hundreds of others to do the same. Whether you're new to investing or ready to raise capital for your first deal, this conversation simplifies the path to building generational wealth.

You’ll learn:

• What syndication really is and how it applies beyond real estate
• How to gain credibility even if you’re brand new
• Why experienced operators want to partner with beginners
• The right mindset for raising capital
• How to structure your first deal (and avoid legal pitfalls)

If you want to master the skill of using other people’s money to build lasting wealth, this is the episode to start with.

Follow and share The Hotel Investor Playbook so more people can learn how to invest in hospitality assets the right way.

About Desiree

Desiree Doubrox is a seasoned real estate investor, broker, and syndicator with over 30 years of experience in the industry. She is the founder and CEO of HomWork, a co-living and co-working platform designed for professional women and remote workers. Through her $10 million fund partnership with Outsite, she’s scaling lifestyle-driven properties that combine community, productivity, and passive income. Desiree is also an educator, hosting workshops like “Syndications Simplified” to empower others, especially women, to build wealth through collaborative real estate investing.

Connect with Desiree

Email: desiree@homwork.com

Linkedin: https://www.linkedin.com/in/desireedoubrox/

Website: https://www.homwork.com/

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

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It took zero dollars of his own money to buy a $4.5 million waterfront resort. It took three years and over a million and a half dollars out of pocket just to keep it.

In this episode, you'll discover the deal, debt, equity sequence he says has never failed to raise capital on a good deal, and exactly when a joint venture beats a syndication.

A multifamily investor who scaled to over 600 rental units, and once raised $10 million without a following or a dollar from family, walks through the one hospitality deal that broke all his usual rules. Christian Osgood unpacks exactly where his due diligence missed the mark, and the strategy he used to turn a struggling resort into a self-sustaining cash machine.

In this episode, you'll discover:

• Spot the hidden payroll problem that makes a mom-and-pop hotel's books lie to you
• Avoid the seller-financing structure that can wipe out a full year of cash flow in one payment
• Turn dead event space into guaranteed income through master leasing, fixed checks every month, with zero staffing or cleanup
• Combine a $1,000 a month ad budget with free community events to drive a 43% profit jump in twelve months
• Apply the deal, debt, equity framework before you ever start looking for investors
• Decide when a joint venture beats a syndication so you can skip the legal headaches

If you're underwriting a boutique hotel or resort deal, this conversation could save you from learning these lessons the expensive way.

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 Christian Osgood

Website: https://multifamilystrategy.com/

YouTube: https://www.youtube.com/@Multifamilystrategy

LinkedIn: https://www.linkedin.com/in/christian-osgood-10a95b71

Connect with Michael on Instagram or LinkedIn.

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Instead of chasing bookings, the founders behind Bolt Farm Treehouse create an obsession amongst their guests, and they do it with love at the center of everything. Their hospitality business heals relationships, attracts top-tier employees, and doesn't require the use of OTAs

In this episode, Seth and Tori Bolt break their iconic hospitality business where luxury stays meet emotional transformation.

You’ll hear:

• How to design experiences that emotionally move your guests
• Why 100% of their bookings are direct, and how to do the same
• How they built a performance-based team culture rooted in love
• How they use AI to automate grunt work and scale high-touch moments
• Why their recruiting funnel brings in 12,000+ applicants a year

This episode is your blueprint for turning a stay into a movement. 

About Seth & Tori

Bolt Farm Treehouse is a luxury adults-only mountaintop retreat founded by Seth and Tori Bolt, born from their honeymoon treehouse and built into an eight-figure hospitality brand. Nestled in Tennessee, the retreat offers high-end domes, mirror cabins, and treehouses designed for romance, reconnection, and escape into nature. Known for their viral marketing, soulful storytelling, and sustainable mission, Seth and Tori have created more than just a destination—they’ve crafted an experience that’s redefining luxury in the wild. Each stay supports tree-planting efforts and is packed with intentional design, curated moments, and heartfelt hospitality.

Connect with Seth & Tori

LinkedIn: https://www.linkedin.com/in/seth-bolt-73061790/

Website: https://www.boltfarmtreehouse.com/

IG:  @toribolt & @boltfarmtreehouse

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Email Us at info@hotelinvestorplaybook.com

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Thinking about buying or operating a hotel, but not sure where to start?

Sujay Mehta built a $187M hospitality portfolio by betting on himself, starting lean, and learning through execution. In this episode, he breaks down what most people get wrong about hotel investing and how you can start smarter.

You’ll learn:

• How to determine which hotel brand fits a deal best
• How the “Mamba Mentality” shaped his risk tolerance and execution
• What he learned by making his first deal a ground-up development
• Whether a boutique hotel can compete with Hilton in your market
• How to add real value to a flagged hotel without a massive reno
• Why throwing away bacon could cost you $1M+ at exit
• The case for self-management vs hiring a third-party operator

Whether you're analyzing your first hotel deal or looking to scale your portfolio, this one’s packed with tactical insights and real-world lessons.

About Sujay

Sujay Mehta is a hotel entrepreneur and real estate investor who built a $187M+ hospitality portfolio before turning 30. A former cancer researcher turned founder, Sujay leads Bloom Ventures—a Columbus-based investment firm focused on boutique and branded hotel development, ground-up builds, and value-add repositioning. He’s known for his creative capital strategies, operational insight, and commitment to hospitality with purpose. Through content, syndications, and strategic partnerships, Sujay helps others scale in the hotel space while staying grounded in family and mission.

Connect with Sujay

LinkedIn: https://www.linkedin.com/in/sujay-mehta-b80411142/

Website: https://bloom.ventures/ & https://www.kafafinancial.com/

Instagram: @sujmehta , @kafafinancial & @hotelinvestoracademy

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What does it take to build a successful hospitality business in a small rural town, with no outside investors? Dave Cook, founder of Barn Door Hostel in Rumney, New Hampshire, walks us through his journey from hostel volunteer to hostel owner.

We dive into:

• How he used sweat equity and personal savings to convert an old chicken coop into a thriving hostel
• His research process on demand, shared economy trends, and local recreation patterns
• The hidden cost of rural hospitality: zoning, septic, ADA, fire codes, and more
• How he fills beds year-round in a seasonal market
• The emotional toll and personal sacrifices that come with being a first-time hospitality operator
• His long-term outlook on scaling, balance, and defining success on your terms

Whether you're dreaming of opening a hostel or just curious about rural hospitality investing, this one’s packed with hard-earned lessons.

About Dave

Dave is the founder of Barn Door Hostel in Rumney, New Hampshire—a community-driven basecamp for climbers and adventurers, built from the ground up (literally, from a chicken coop). With over a decade of experience in hospitality, climbing gyms, and youth programming, he brings heart and intention to every guest experience. He's also a passionate advocate for access and stewardship, serving as a board member for the Rumney Climbers Association and a Ski Kind ambassador. Follow along as we dig into the journey behind Barn Door and the spirit of adventure it inspires.

Connect with Dave

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

Website: https://www.barndoorhostel.com/

Instagram: @barndoorhostel

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Today’s guest bought a roadside motel in a town of 900 people and turned it into a thriving hospitality brand.

In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Austin Phippen, a 26‑year‑old owner of Chama Trails Motel, a portfolio of 12 short-term rentals and a scenic wedding venue in Chama, New Mexico.

What you’ll learn from this episode:

• The “Motel Hack” mindset: How Austin got in with seller financing and turned the motel into both home and business
• Scaling without overbuilding: Why he ran it “as-is” in year one and focused on reviews before renovations
• Bundling to build a team: How combining the motel, STRs, and a venue created enough revenue for full staffing
• Remote operations, done right: What you must know before investing in a rural town you don’t live in
• Marketing that works: Why Google reviews and great operations now drive over 85% of bookings directly

If you’re serious about hospitality investing, especially in rural or seasonal markets, this episode is a must-listen masterclass in bootstrapping, brand-building, and sustainable growth.

About Austin

Austin and Karlee Phippen are the powerhouse couple behind Turquoise Antler Hospitality, a growing portfolio of boutique rentals, a 16-room motel, and a stunning wedding venue in Chama, New Mexico. Since launching in 2019, they've transformed a small-town motel into a thriving hospitality brand with a team of 20 and over a dozen co-hosted properties. With Austin’s background in construction and Karlee’s roots in hospitality, they’ve created unique stays that blend rustic charm with modern comfort. In this episode, they share how they scaled their business, built community partnerships, and navigated the wild world of rural hospitality.

Connect with Austin

Email: austin@turquoiseantler.com

LinkedIn: https://www.linkedin.com/in/austin-phippen-730569124/

Instagram: @chamavacationrentals and @phippenout

Website: https://chamavacationrentals.com/

Have a deal? Send it to us here: https://api.leadconnectorhq.com/widget/form/28iLM67xiWWNkekg8ONt

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

Invest with Malama Capital

Submit a deal