The Hotel Investor Playbook

Michael Russell
  • 5.0 (66)
  • INVESTING
  • UPDATED WEEKLY

Welcome to The Hotel Investor Playbook, hosted by real estate investor and hospitality operator Michael Russell. Michael is the co-founder of Malama Capital and Howzit Hostels, and has built a personal real estate portfolio exceeding $20 million.With an operator-first mindset, Michael brings a practical perspective to hotel investing. On the show, he breaks down what it actually takes to scale from short-term rentals into boutique hotels, covering deal sourcing, operations, capital strategy, and risk.Each week, Michael shares real lessons from the field as he builds toward a $400 million real estate business, giving listeners an honest look at the decisions, challenges, and strategies behind the growth. Subscribe and follow along as he documents the journey in real time.

  1. The Revenue Expert Managing $125M Says You're Leaving 40% on the Table | Jasper Ribbers E74

    MAR 17

    The Revenue Expert Managing $125M Says You're Leaving 40% on the Table | Jasper Ribbers E74

    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 Invest with Malama Capital Submit a deal

    40 min
  2. What Hotel Investors Can Steal From a Land Investor Who's Done 400 Deals | Brent Bowers E73

    MAR 10

    What Hotel Investors Can Steal From a Land Investor Who's Done 400 Deals | Brent Bowers E73

    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 tooThe 3-step market selection framework that identifies where deals are actually moving before you spend a dollarHow shifting from high-volume, low-margin transactions to low-volume, high-profit deals changed everythingThe infrastructure plays a role in turning raw land into turnkey assets, and why hotel developers should be paying attentionWhy scaling your team is often the problem, not the solutionThe 10 am-3 pm boundary that forced a complete redesign of a 7-figure businessIf 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 Invest with Malama Capital Submit a deal

    40 min
  3. An Overlooked Strategy That Makes $7M Hotel Deals Actually Pencil | Ben Wolff E72

    FEB 24

    An Overlooked Strategy That Makes $7M Hotel Deals Actually Pencil | Ben Wolff E72

    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 manufacturersThe land lease structure that makes a $7M property deal actually pencil when outright ownership never wouldHow 50% NOI margins are achievable when most traditional hotels average half thatWhy direct bookings command higher ADRs than OTA guests, and the exact content strategy behind itThe lean staffing modelis  running 63 keys across two properties without bloated overheadThe one mindset shift that separates developers who survive ground-up builds from those who quitIf 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 Invest with Malama Capital Submit a deal

    51 min
  4. Former Hotel Analyst Built AI to Fix the Problem He Lived Every Day | Ziggy Hallgarten E71

    FEB 17

    Former Hotel Analyst Built AI to Fix the Problem He Lived Every Day | Ziggy Hallgarten E71

    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 upHow Broome.ai cuts deal screening from 2 hours down to 30 minutes or less by automating data extractionWhy Ziggy left his family's hotel business to build his own company from scratchFree tools you can use to build software prototypes without any coding knowledgeWhere AI will have the biggest impact on hotels: revenue management and operationsThe biggest mistake founders make: trying to solve every problem instead of focusing on onePractical ways hotel investors can start leveraging AI in their workflow todayWhether 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 Invest with Malama Capital Submit a deal

    43 min
  5. How to Scale to 4 Hospitality Properties Without Raising Millions in Capital | Sam Degenhard E70

    FEB 10

    How to Scale to 4 Hospitality Properties Without Raising Millions in Capital | Sam Degenhard E70

    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 acquisitionsHow to partner with real estate investors who buy the land while you control 100% of operations and guest experienceWhy focusing on the business side lets you open properties faster with significantly less capitalThe owner-operator staffing model that runs an 8-bedroom lodge profitably with one employeeHow to command 4-5X market rates by building brand loyalty instead of competing on OTA platformsThe due diligence process that identifies underperforming assets is perfect for operational turnaroundsWhy subscale properties under 30 keys deliver better margins than traditional hotel modelsWhether 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. 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

    56 min
  6. This 3-Step System Automated His Real Estate Business to 4 Hours a Month | Mark Podolsky E69

    FEB 3

    This 3-Step System Automated His Real Estate Business to 4 Hours a Month | Mark Podolsky E69

    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 itHow 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 tasksWhy the biggest mistake new investors make isn't about the property—it's about their calendarThe "brick your phone" strategy that helped Mark reclaim focus and family timeThe 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 Invest with Malama Capital Submit a deal

    34 min
  7. How Small Hotels Use Staff Content to Drive Direct Bookings | Scott Eddy E68

    JAN 27

    How Small Hotels Use Staff Content to Drive Direct Bookings | Scott Eddy E68

    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 bookersThe exact content categories that drive bookings and why shaky iPhone footage outperforms polished videosHow to make your front desk staff into content superstars without hiring an expensive agencyThe one Instagram metric (hint: it's not followers) that actually predicts revenueWhy "saves" and "comments" matter 10x more than likes for direct bookingsThe AI-discoverable scripting framework that's replacing traditional SEO for hotel discoveryHow 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 guestsIf 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 Invest with Malama Capital Submit a deal

    52 min
  8. How an Ex-Space Force Engineer Bought a $2.45M Motel With 10% Down | Jordan Malara E67

    JAN 20

    How an Ex-Space Force Engineer Bought a $2.45M Motel With 10% Down | Jordan Malara E67

    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 numberThe hidden CapEx that blows budgets: sprinklers, fire systems, laundry equipment, and code compliance workJordan's 60% expense ratio sanity check, and why occupancy lifts are way harder than you thinkHow 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 bathroomsHow he outsources revenue management and bookkeeping globally without bloating payrollIf 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 Invest with Malama Capital Submit a deal

    1h 7m
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5
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66 Ratings

About

Welcome to The Hotel Investor Playbook, hosted by real estate investor and hospitality operator Michael Russell. Michael is the co-founder of Malama Capital and Howzit Hostels, and has built a personal real estate portfolio exceeding $20 million.With an operator-first mindset, Michael brings a practical perspective to hotel investing. On the show, he breaks down what it actually takes to scale from short-term rentals into boutique hotels, covering deal sourcing, operations, capital strategy, and risk.Each week, Michael shares real lessons from the field as he builds toward a $400 million real estate business, giving listeners an honest look at the decisions, challenges, and strategies behind the growth. Subscribe and follow along as he documents the journey in real time.

Information

  • Creator
    Michael Russell
  • Years Active
    2024 - 2026
  • Episodes
    75
  • Rating
    Explicit
  • Copyright
    © 2026 The Hotel Investor Playbook
  • Show Website
    The Hotel Investor Playbook

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