Shows
The Hotel Investor PlaybookHow to Replace a Six-Figure Job with Boutique Hotel Investing | Tim Ensmann E55Ever 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 anymoreHow he u...
2025-10-2850 min
The Hotel Investor PlaybookReal Estate Syndications 101: How Investors and Operators Actually Get Paid | Michael Russell E54Ever 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 paidHow preferred returns, profit splits, and waterfalls actually workThe most overlooked risk in s...
2025-10-2124 min
The Hotel Investor PlaybookWhat It Really Takes to Buy Your First Hotel in 90 Days | Jacobo Hernandez E53When 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 visi...
2025-10-1454 min
The Hotel Investor PlaybookBuilding a Lifestyle Hotel Brand in Costa Rica | Bill Graf E52We’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 ignoreWhat U.S. investors should know about buying real estate in Costa RicaHis unique strategy for keeping his prop...
2025-10-0758 min
The Hotel Investor PlaybookThe “Hotel Guru” on Where to Invest Next & How to Fund Deals | Bob Rauch E51The 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 hotelsThe 4 core skills Bob be...
2025-09-3057 min
The Hotel Investor PlaybookWhy 2026 Looks Rocky for U.S. Hotels And Where Smart Investors Can Hit Big | Jan Freitag E50Where 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 overlookWhy conviction and strong operations can outperform market averagesHow investors can protect margins as costs continue to riseWhy the sub-$10M space stay...
2025-09-2346 min
The Hotel Investor PlaybookHow to Craft a Hotel People Will Actually Remember | Bashar Wali E49The 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 playbooksThe power of emotional intelligence in hotel teamsThe biggest mistakes first-time owners makeThe difference between the three types of hotel deals (core, value-add, and opportunistic)Bashar doesn’t hold back. Whethe...
2025-09-161h 03
The Hotel Investor PlaybookWhat Makes a Hotel Succeed or Fail? | Naveed Khan E48How 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&LsThe advantages (and risks) of branded vs. independent hotels for investorsHow management companies can become a true partner in va...
2025-09-0949 min
The Hotel Investor PlaybookFrom CEO of Days Inn to Launching Marriott’s Autograph Collection | Richard Kessler E47Few 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 CEOThen 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, tea...
2025-09-021h 06
The Hotel Investor PlaybookHow To Use Social Media To Raise Capital And Find Deals | Soli Cayetano E46What 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 audienceWhy documenting your journey builds trust with investorsThe key di...
2025-08-2655 min
The Hotel Investor PlaybookBuilding Hotels That Last the Test of Time | Brandon Gore E45Most 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 bu...
2025-08-1951 min
The Hotel Investor PlaybookThe Marketing Playbook Every Small Hotel Owner Needs | Steph Weber E44Think 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 pointsSimple marketing strategies that work for small hotels and innsWhy guest experience is your most powerful marketing toolThe mindset shift from “just filling rooms” to build...
2025-08-1251 min
The Hotel Investor PlaybookThe Beginner's Guide To Building Wealth In Hospitality | Jonathan Mueller E43Think 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” planHow Jonathan raised $300K in 72 hours to close his...
2025-08-0543 min
The Hotel Investor PlaybookHotel Marketing Decoded: What Every Owner Needs to Know | Anthony Chiaravallo E42Is 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 bookingsWhat makes a great marketing agency vs a waste of moneyHow to kn...
2025-07-2944 min
The Hotel Investor PlaybookSyndication Simplified: The Strategy That Builds Generational Wealth | Desiree Doubrox E41Ever 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 estateHow to gain credibility even if you’re brand newWhy experienced operators want to partner with begi...
2025-07-2252 min
The Hotel Investor PlaybookA Masterclass In Experiential Hospitality With The Bolt Farm Treehouse Founders | Tori and Seth Bolt E40Instead 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 OTAsIn 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 guestsWhy 100% of their bookings are direct, and how to do the sameHow they built a performance-based team culture rooted in loveHow they use AI...
2025-07-1554 min
The Hotel Investor Playbook$187M Hotel Portfolio by Age 30: How to Choose the Right Deals, Brands, and Ops Model | Sujay Mehta E39Thinking 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 bestHow the “Mamba Mentality” shaped his risk tolerance and executionWhat he learned by making his first deal a ground-up developmentWhether a boutique hotel can compete with Hilton in your marketHow to add real v...
2025-07-081h 10
The Hotel Investor PlaybookTurning Passion into Profit in Rural Hospitality | Dave Cook E38What 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 hostelHis research process on demand, shared economy trends, and local recreation patternsThe hidden cost of rural hospitality: zoning, septic, ADA, fire codes, and moreHow he fills beds year-round in a seasonal marketThe emotional toll and...
2025-07-0144 min
The Hotel Investor PlaybookBootstrapped Hospitality: Scaling Your Hotel Portfolio Without Major Capital | Austin Phippen E37Today’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 businessScaling without overbuilding: Why he ran it “as-is” in year one and focused...
2025-06-2437 min
The Hotel Investor PlaybookBuilding a Scalable Outdoor Hospitality Brand Through Franchising | Brian Linton E36In this episode of the Hotel Investor Playbook, Mike and Nate sit down with Brian Linton, co-founder of Finding Promised Land, Camp Ferncrest, and The Rex Hotel. Brian shares how he transitioned from building a $20M apparel company to launching one of the fastest-growing outdoor hospitality brands in the U.S.Key Topics:How a rundown motel purchase during COVID led to a hospitality empireNavigating zoning issues, STR restrictions, and neighborhood pushbackWhat to look for in land: acreage, utilities, proximity to population, and state parksWhy owning your business outright may beat raising capitalHow Brian is using...
2025-06-171h 00
The Hotel Investor PlaybookHow to Know If Your CPA Is Helping You or Holding You Back | Kelly Tate E35Not sure if your tax advisor is actually optimizing your returns, or just filing forms? In this episode of the Hotel Investor Playbook, we’re joined by Kelly Tate, a CPA with over two decades of experience helping real estate and hospitality investors navigate the tax code with confidence.We dive into key strategies like bonus depreciation, Section 179, and cost segregation, and explore how to structure your entities to maximize tax efficiency, especially when you’re juggling both real estate ownership and active operations.Whether you’re an experienced sponsor or just scaling into your first...
2025-06-1051 min
The Hotel Investor PlaybookWhy Hostels Are an Untapped Investment Opportunity in the U.S. | Mike & Nate E34We're proving why hostels are one of the most powerful investment models in real estate. In this episode, Mike and Nate break down exactly why they’re going all-in on hostels and how they turn underperforming assets into award-winning hospitality destinations.You’ll learn:Why the U.S. hostel market is ripe for disruptionThe revenue model that turns $100 rooms into $300 cash machinesHow their guest-first brand became a marketing engineWhy “flawed” properties are actually a goldmine for this modelWhat Gen Z travelers are demanding and why hostels deliverPlus, some hints on what they're building next in Los Angeles
2025-06-0336 min
The Hotel Investor PlaybookThe Strategic Power of Third-Party Hotel Management | Bryan Fish E33You don’t need to be an expert in everything to scale in hospitality, just need to align with the right consultants, operators, and partners who’ve done it before.In this episode, we sit down with Bryan Fish, CEO of Reliance Hospitality, to unpack how third-party operators help investors go from scrappy operators to institutional-level players. Bryan shares what most owners get wrong during acquisitions, how franchise agreements really work behind the scenes, and why your ability to scale comes down to the team you build around you.If you’re trying to grow beyond...
2025-05-2745 min
The Hotel Investor PlaybookHe Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32After helping scale a family office real estate portfolio from $3 million to over $320 million, Reilly Brennan walked away from the comfort of a W-2 job to carve his own path in boutique hospitality.In this episode, we sit down with Reilly to unpack how he sourced and acquired two independent hotels in Duluth, Minnesota, one through creative seller financing, the other straight off LoopNet. We break down his underwriting process, deal structure, construction strategy, and how he’s building a brand that reflects his values, not someone else’s investment thesis.You’ll also hear:
2025-05-2047 min
The Hotel Investor PlaybookBuilding a $6M Micro Resort with Only 3% Down Using a USDA Loan | Ian Joseph E31In this episode, we dive into an uncommon but powerful financing strategy that could change how boutique hospitality projects get funded. Ian Joseph, founder of Branch, shares how he’s leveraging a USDA Rural Business Development loan to finance a $6M micro resort buildout in West Virginia - with just 3% down.We break down the entire capital stack, how USDA loans work for ground-up hospitality development, and why this financing tool is often overlooked by small to mid-size investors. Ian also shares his approach to designing high-ADR resort cabins, partnering with local economies, and building a scalable br...
2025-05-1347 min
The Hotel Investor PlaybookThe Ultimate Guide To Financing Your Next Hotel Deal | Suraj Desai E30In this episode of the Hotel Investor Playbook, we sit down with Suraj Desai, a hospitality finance expert who has helped close hundreds of hotel deals, to unpack everything you need to know about financing your next acquisition, renovation, or ground-up development.Suraj breaks down the full capital stack, from SBA 7a and 504 loans to bridge, CMBS, and mezzanine debt. He explains which types of financing work best for boutique hotels vs. flagged assets, why banks are pulling back, and what it really takes to get a deal funded in 2025.We also cover:The...
2025-05-0653 min
The Hotel Investor PlaybookBuying Hotels Is Just the Start: How to Build a Lasting Hospitality Brand | Keir Weimer E29In this episode of the Hotel Investor Playbook, we sit down with Keir Weimer, founder of Weekender Hotels, to unpack how he’s building a boutique hospitality brand designed for the long haul. Keir shares how he aligned his business with his personal lifestyle, his on-the-road strategy for sourcing deals, and the frameworks he’s using to scale Weekender into a generational hospitality company.We dive into why building a recognizable brand creates enterprise value beyond just owning hotel assets, how he structures his investments for long-term holds, and why focusing on guest experience drives lasting financial resu...
2025-04-2948 min
The Hotel Investor PlaybookHotel Investing Insights from the CEO of One of America’s Top Hotel Brokerage Firms | Suraj Bhakta E28What does it really take to scale from your first hotel acquisition to managing a hospitality portfolio worth tens or even hundreds of millions?In this episode, Michael and Nate sit down with Suraj Bhakta, CEO of NewGen Advisory, a leading hospitality brokerage with offices across 12 states and transactions in 44. Suraj brings over two decades of commercial real estate experience, having closed $850 million in hotel deals and facilitated nearly $500 million in capital raises. He’s also Chief Legal Counsel at NewGen Worldwide and a former managing partner of his own law firm.Together, we dive de...
2025-04-2252 min
The Hotel Investor PlaybookSaturday Special: Behind the Curtain at Malama Capital | Mike & Nate E27In this special Saturday edition, we’re flipping the script. No guest today — just Mike and Nate giving you a behind-the-scenes look at what’s going on inside Malama Capital.After a listener reached out asking to hear more about our journey, we decided to hit record and share where we’re at, what we’re focused on, and how we’re thinking about the road ahead.We cover:Why Q2 is all about acquisitions and our $10M purchase goalHow we’ve restructured our team to create more bandwidthUsing...
2025-04-1925 min
The Hotel Investor PlaybookHow Sky McLean Built a $500M Hotel Brand from Scratch | Sky McLean E26What do you do when you get fired from your job and get escorted out with a cardboard box? If you’re Sky McLean, you build one of the fastest-growing hospitality brands in Canada.In this episode, we sit down with Sky McLean, founder and CEO of Basecamp Resorts, owner of 14+ resorts, and operator of over half a billion in real estate. From bootstrapping her first hotel with a BMW loan to raising $40 million through Instagram, Sky’s story is a masterclass in grit, creativity, and bold vision.We dig into how she scaled her adve...
2025-04-1538 min
The Hotel Investor PlaybookGlamping for Profit: Low Cost, High Cash Flow, Massive Upside | Zac Willms E25What if you could double your money in one season with glamping tents? Zac Willms is pulling it off — and building a profitable outdoor brand in the process.In this episode, Mike and Nate talk with Zac Willms, co-owner of a thriving glamping resort in Tobermory, Ontario. Zac shares how he turned a neglected trailer park into a profitable outdoor hospitality destination, the simple formula behind his success, and why buying an old campground might be the real cheat code.We unpack everything from startup costs, seasonal cash flow, and staffing — to marketing strategy, zoning hack...
2025-04-0851 min
The Hotel Investor PlaybookOlympic Discipline, Million-Dollar Loss, and Building a Hospitality Portfolio | Adam G Dailey E24From Olympic Trials to Losing Millions—And Bouncing Back With a Boutique Hotel EmpireIn this episode of Hotel Investor Playbook, Mike and Nate are joined by Adam Dailey, a former 5x All-American athlete turned hospitality investor. Adam shares his wild journey—from building a multimillion-dollar business, losing it all in a matter of weeks, to bouncing back stronger with a growing portfolio of boutique hotels, hostels, and STRs.We unpack:•How championship-level discipline translates to high-performing hotel operations•The mindset shift from solo business owner to team-driven investor•Tactical w...
2025-04-011h 07
The Hotel Investor PlaybookFrom Motel Renovation to 300K Followers: The Innvestors Story | Brett McManus E23What happens when two young investors decide to buy a rundown motel, renovate it themselves, and document the entire journey online? For Brett and Casey McManus—creators of the viral Instagram account Innvestors—it led to a booming boutique hotel business and a wildly loyal following.In this episode, Brett joins us to share how they went from industrial real estate to short-term rentals, and ultimately into purchasing a hotel—with a storytelling approach that’s as entertaining as it is effective. We dive into how they’ve built real brand equity through content, why they’ve avoided the...
2025-03-251h 00
History ImpossibleDiplomacy on the Eastern Border (w/ Kristaps Andrejsons, Jack Johannson, & Zack Twamley)I was recently invited to join in a panel discussion with three podcasting greats and people I consider friends—that is, The Eastern Border’s Kristaps Andrejsons, the Secret Police podcast’s Jack Johannson, and When Diplomacy Fails podcast’s Zack Twamley. It originally went up on the Eastern Border feed, split into two parts, but Kristaps was kind enough to let all of us get our grubby paws on the masters to put on our own feeds, something that I felt would allow me to give all of you fine people another nice bonus while you wait for the next ins...
2025-03-252h 53
The Hotel Investor PlaybookGround-Up Boutique Hotel Development in San Francisco - High Risk, Higher Reward? | Mike Demson E22Could you really buy a hotel development site in Fisherman’s Wharf, San Francisco—at a fire-sale price—and turn it into a boutique hotel with a projected value over $11 million?That’s the plan today’s guest, Mike Demson, is working on. In this episode, Mike breaks down how he’s finding undervalued hotel opportunities, increasing density, reducing construction costs, and creating Instagram-worthy experiences with lean operations and smart design.We challenge the assumptions, dig into the numbers, and talk about what it actually takes to pull off a project like this.You’ll also...
2025-03-1853 min
History ImpossibleThe Slave Who Would Be a Spy (w/ Isaac Willour)Slavery is often known as the United States’ original sin, and for good reason. Much of our perceptions of it are informed both by the Civil War’s cause and outcome, and the contradictions—and even moral hypocrisy—that it created with our Founding Fathers’ professed beliefs. Contradiction is the theme not just of the United States’ values and history, but it also a major theme of this episode of the podcast.In this newest installment of History Impossible, we’re looking at the extraordinary life of James Armistead Lafayette, the slave who would become the Colonies’ most vital spy during...
2025-03-141h 00
The Hotel Investor PlaybookWhat It Takes to Build a Revolutionary Hospitality Business | Brian Meyer E21What if your next hospitality investment didn’t sit on land?In this episode, Mike and Nate sit down with Brian Meyer, founder and CEO of Flow Home—a luxury floating home rental business redefining waterfront living. We explore how Brian turned a niche concept into a scalable brand, how he raised capital, overcame regulatory barriers, built vertically integrated operations, and is now expanding into floating communities and resorts.If you’re a hotel or STR investor looking for what’s next, you’ll love this conversation on innovation, scaling, and why the future of real estat...
2025-03-1148 min
The Hotel Investor PlaybookCost Segregation Made Simple: Unlock Massive Tax Savings in Real Estate | Brian Bigham E20“Do you enjoy paying taxes? Would you like to learn how to keep more of your hard earned money?In this episode of The Hotel Investor Playbook, Mike and Nate sit down with Brian Bigham, Vice President at Madison Specs and also known as the Cost Seg Cowboy. Brian breaks down the powerful strategy of cost segregation, showing you how to legally keep more of your hard-earned money by accelerating depreciation on your real estate investments.Listen in as Brian simplifies complex tax strategies using analogies like the “Pizza Method,” making it easy to understand how yo...
2025-03-0438 min
History ImpossibleA Bug in the SoftwareHey everyone, happy to present to all of you fine people with a brief bonus, this time adapting my recent historiographical essay that I had written my first semester in graduate school on the study of infectious disease’s effects throughout history and how it was written about from around the 1970s until the 2010s. This should serve as a nice pairing with the recent “Mother’s Wrath, Mankind’s Cope” and demonstrate the sort of academic origins of my thinking on this particular subject. Please enjoy and stay tuned!…History Impossible has been made possible by the follo...
2025-02-2856 min
The Hotel Investor PlaybookFrom First Responder to Ground-Up Developer: An Inspiring Journey | Andrew Owlett E19Ever dreamt of creating your luxury resort from scratch? In this episode, we’re diving deep into the world of ground-up hospitality development with Andrew Owlett, a visionary building a boutique wellness resort in Virginia— with plans to expand into three other states!Here’s what you’ll learn:🔥 The freedom and challenges of developing from scratch — Why Andrew chose to build rather than buy.🔑 Critical first steps — From forming the right team to finding the perfect piece of land.📍 Navigating zoning and special permitting — The do’s and don’ts of turning raw land into a...
2025-02-2550 min
The Hotel Investor PlaybookHow AI is Disrupting Hotels—And Why Small Operators Have the Advantage | Ari Smith E18💡 AI is revolutionizing hospitality, but not how you think.The big hotel chains? They’re struggling to adapt. The real advantage? It belongs to small, independent operators who know how to leverage AI the right way.On this episode of The Hotel Investor Playbook, we sit down with Ari Smith, an AI scientist and futurist, to unpack:✔️ How AI is making boutique hotels more profitable than ever✔️ Where to automate—and where human service is irreplaceable✔️ Why ultra-luxury stays will always demand a human touch✔️ The AI-driven hospitality tech that’s...
2025-02-2056 min
History ImpossibleMother's Wrath, Mankind's Bargain (The Los Angeles Fires of 2025)In this episode of History Impossible inaugurating 2025 and the sixth anniversary of the show, we will be looking at the Los Angeles Fires of 2025 but from an extended, historical, and probably overly philosophical lens. Because as it turns out, natural disasters are a constant of the human experience and create some of the greatest extremes, and reflecting on what afflicts us now alongside what has afflicted us in the past can provide at least some clarity (or, in my case, closure).The destruction faced by Los Angelenos in 2025 is not too dissimilar from many examples of destruction in...
2025-02-131h 50
The Hotel Investor PlaybookBuying, Financing & Operating a Seasonal Boutique Hotel | Ryan Edwards E17🏨 How do you turn a seasonal boutique hotel into a $2M value-add opportunity?In this episode of The Hotel Investor Playbook, we sit down with Ryan Edwards, owner of a 17-unit boutique hotel in Maine, to break down the real strategies that make a seasonal hotel thrive.We cover:✅ How he financed his $3.6M hotel deal with 75% bank financing✅ The $100K revenue increase that added $1.4M in value✅ How he built a 100% direct booking strategy (no OTAs!)✅ Staffing challenges & using visa programs for seasonal workers✅ Marketing strategies that fill rooms months...
2025-02-1153 minThe Hotel Investor PlaybookThe Glamping Boom: Hype, Profits, & Pitfalls | Edward Haynes E16Luxury glamping—game-changing investment or overhyped trend?In this episode of The Hotel Investor Playbook, we sit down with Edward Haynes, a specialist in unique stays and experiential lodging, to unpack the massive growth in luxury outdoor hospitality.We cover:✅ Why glamping demand is skyrocketing (and if it’s sustainable)✅ How unique stays can outperform traditional hotels in revenue✅ What it really takes to develop a profitable glamping site✅ The biggest mistakes investors make in this space✅ How major hospitality br...
2025-02-0545 minThe Hotel Investor PlaybookFrom Vision to Execution: Our Framework for Hospitality Success | Mike & Nate E15Do you feel like you’re always busy but never really making progress? In this episode of The Hotel Investor Playbook, we explore how to transform your vision into reality by cutting through the noise and focusing on what truly matters.Join Mike and Nate as they share their proven four-step process for executing your 2025 goals: from crafting a clear and compelling vision to creating accountability structures, setting measurable objectives, and tracking progress with a weekly scorecard.Whether you’re just starting out or scaling your hospitality business, these practical strategies will help you eliminate bott...
2025-01-2859 minThe Hotel Investor PlaybookLessons Learned from a Failed Motel Deal | Tanya Rooney E14What happens when a hotel investment doesn't go as planned?In this candid episode of the Hotel Investor Playbook, we chat with Tanya Rooney about the ups and downs of buying and operating a roadside motel. From discovering hidden challenges in partnerships and revenue projections to navigating the nuances of small-town hospitality, Tanya's story is packed with invaluable lessons.You'll learn:How to spot red flags during underwriting and due diligence.The differences between short-term rental investing and hotel operations.Why partnerships are like marriages - and how to choose the right one.Actionable...
2025-01-2147 minThe Hotel Investor PlaybookTurning $400K into $10M: Lessons in Fear, Failure, and Direct Bookings | E13What does it take to transform $400,000 into $10 million in hospitality assets while building a brand that wins awards in just a few years? In this special crossover episode, we’re featuring a conversation we had as guests on Direct Bookings Simplified, hosted by Gil Chan.In this episode, we reveal:•How we tackled fear and failure to seize opportunities others missed.•The strategies behind our 12% increase in direct bookings—adding $600K+ to our property valuation.•Why obsessing over guest experience, systems, and culture is the ultimate hospitality growth formula.
2025-01-161h 03
Booked Solid Show - Short Term Rental PodcastEP44 - From Pandemic Gamble to Hospitality Triumph: The Howzit Hostels Road to $10M in Assets with Michael Russell and Nathan St.CyrWhen you think of hostels, the image of a small, budget-friendly, often outdated lodging comes to mind. Nathan and Michael, the co-founders of Howzit Hostels, are flipping that narrative.
In our latest podcast episode of Direct Booking Simplified, these two entrepreneurs shared how they leveraged their backgrounds in real estate and luxury short-term rentals to redefine what a hostel can be—and how their direct booking strategy is a game-changer.
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2025-01-101h 02The Hotel Investor PlaybookHow a Property Manager Can Help You Maximize Your Hotel Profits | Bryan Tubaugh E12Join us as we sit down with Bryan Tubaugh, a seasoned hotel management expert, to explore the common pitfalls of self-management, the benefits of bringing in a pro, and how to evaluate whether outsourcing management is right for you. Whether you’re buying or managing your first—or fiftieth—hotel, this conversation is packed with insights to help you maximize your investment.”Episode Summary:Hotel ownership comes with tough decisions, and none bigger than whether to manage your property yourself or bring in the pros. In this episode of The Hotel Investor...
2025-01-0752 min
Short Term Rental Secrets PodcastEp 223 - The $400 Million Hostel Brand with Michael Russell and Nathan St CyrReady to scale your short-term rental or hostel business to new heights? In this episode, we’re uncovering proven strategies for building a $400 million hospitality brand, creating exceptional guest experiences, hiring and leading top-tier teams, and navigating zoning regulations for growth. Listen now and learn how to turn bold visions into reality!02:25 - Scaling to $400 Million with Focused Hospitality04:29 - Leveraging Partnerships for Rapid Expansion06:09 - Spotting Hidden Opportunities in Hospitality Markets08:14 - Creating Systems and Processes for Seamless Scaling09:03 - Prioritizing Guest Experience for Maximum Impact10:40...
2025-01-0645 minThe Hotel Investor PlaybookLeveling Up: How To Turn STR Success into Boutique Hotel Ownership | Kim Herrlein E11Are you ready to take your short-term rental success to the next level? In this episode of The Hotel Investor Playbook, we sit down with Kim Herrlein, an accomplished STR investor who transformed her success into hotel ownership.Kim’s story isn’t about leaving short-term rentals behind—it’s about using her knowledge to scale into an exciting new chapter. She reveals how she sold a high-performing vacation rental to buy a boutique hotel for under $1 million, the challenges of renovations, and how she built a remote team to manage it all.Here’s what you’l...
2024-12-3148 min
History ImpossibleA Revulsion of Feeling: The Arab Revolt and Collective IdentityThis is the first installment of something that doesn’t really have a name; the Grad School Files? That sounds a little like a bad Netflix show. I’ll take suggestions, but in the meantime, we can simply define this as it is: the first adaptation of one of my academic papers from graduate school into an honest-to-goodness episode of History Impossible. The first thing I want to say is that it was more difficult than I expected to adapt an academic paper into a podcast than I expected. The material is all there, but speaking in formal academic language mana...
2024-12-301h 31The Hotel Investor PlaybookHow to Drive 70% Direct Bookings: Strategies for Hotel Investors | Kerri Gibson E10Are you tired of paying high fees to online travel agencies (OTAs)? Imagine driving 70% of your bookings directly—and keeping more of your revenue. In this episode of The Hotel Investor Playbook, we sit down with Kerri Gibson, founder of Chalets Hygge, who has built an incredible hospitality brand with six short-term rentals and a boutique motel.Here’s what you’ll learn in this episode:•The importance of starting with a Google Business Profile to build credibility.•How to select the right property management system (PMS) and tech stack to scale your business.
2024-12-1757 minThe Hotel Investor PlaybookBuilding a Winning Investment Thesis for Hotel Success | Mike & Nate E9Join Mike and Nate, founders of Malama Capital, as they explore the critical role of a well-defined investment thesis in the hospitality industry. With $30 million in current real estate assets and a goal to build a $400 million business, they share detailed insights on creating and refining an investment strategy. From understanding guest avatars to leveraging capital expenditures and occupancy rates, this episode is packed with practical advice for both novice deal finders and seasoned investors. They highlight the importance of clarity, market research, and realistic benchmarks to ensure profitable hospitality acquisitions. Tune in to learn how...
2024-12-1043 min
History ImpossibleThe Question of GenocideThis episode of History Impossible is an adaptation of the historical polemic I wrote on the one-year anniversary of October 7th, 2023, examining the interpretation of genocide, as applied to the current war between Hamas and Israel, and to the devastation wrought against the Bosnian Muslims by their Serb counterparts in the early 1990s. This episode touches on some extremely upsetting and dark material, including descriptions of child death, mass killing, and rape, so please consider yourself warned if that sort of thing is something you might want to avoid.This episode will serve as a polemical counterpart to...
2024-12-061h 04The Hotel Investor PlaybookHow to Build a Hotel: Expert Insights into Real Estate Development | Zeke Freeman E8Ever wondered what it takes to transform an empty building or raw land into a thriving hotel? In this episode of The Hotel Investor Playbook, we’re diving deep into the real estate development process with architect and developer Zeke Freeman.With over 20 years of experience and a current ground-up hotel project near the iconic Red Rocks Amphitheater, Zeke walks us through the entire journey—from identifying the right property to navigating zoning, entitlements, and building permits. We tackle the nitty-gritty of feasibility studies, managing risk, raising capital, and assembling a winning team of architects, contractors, and cons...
2024-12-031h 01
Radical Hospitality ShowBuilding a $400M Hostel Empire: From Airbnb to Hawaiian HostelsAfter a chance encounter with a real estate agent, Michael Russell and Nathan St Cyr run two of the highest ranked hostels on the Hawaiian islands. After owning multiple Air BNB short-term rentals, they decided to transition into the big leagues - building out a team and infrastructure to scale their currently $30M portfolio in Hawaii a $400M hostel empire across the US.To learn more about their real estate playbook, see their accountability tool here: https://www.hotelinvestorplaybook.com/p/accountability-tool/00:00:00:00 - Welcome and IntroductionNathan and Michael's journey from real...
2024-12-0251 minThe Hotel Investor PlaybookHow to purchase your first hotel while working a full-time job | Alex Kang E7In this episode, we dive deep into the inspiring journey of Alex Kang, who purchased his first boutique hotel with no prior experience while maintaining a full-time W2 job.Alex shares his step-by-step process, from leveraging his skills from his MBA and software tech job, to joining a mastermind group that accelerated his learning.He emphasizes the importance of mentorship, partnership, and leveraging his W2 network to raise funds for his $9 million hotel project.Kang provides practical advice on time management, setting clear goals, disciplined prospecting, and staying motivated through challenges.Whether you're juggling a...
2024-11-271h 03The Hotel Investor PlaybookShould You Operate a Branded Hotel or Go Independent? | Neil Shah E6With over 100,000 hotels in the United States, approximately 70% operate as branded or flagged hotels. But why is that? If you’re considering purchasing a hotel and debating between going independent or affiliating with a recognized brand, this episode is a must-listen.We’re joined by hospitality industry expert Neil Shah, who brings over 25 years of experience in hotel investing, with 13 hotels and 471 units purchased under his belt. Neil has worked with six different hotel franchises, including well-known names like Best Western, Hampton Inn, and Howard Johnson. Together, we explore the advantages and trade-offs of operating as a bran...
2024-11-191h 06The Hotel Investor PlaybookHow to Source, Underwrite, and Purchase Your First Boutique Hotel | Gideon Spencer E5In this episode of the Hotel Investor Playbook, hosts Mike and Nate sit down with Gideon Spencer, the principal of Stonemont Capital, who purchased a $6 million hotel at the age of 32. Gideon shares his journey from starting in real estate with a fourplex to acquiring a boutique hotel, providing invaluable insights into market research, capital raising, and deal validation. The episode delves into practical steps for finding and analyzing hospitality deals, the importance of building broker relationships, and effective capital-raising strategies. Gideon emphasizes the significance of aligning with experts to scale investments and offers motivational advice on overcoming self-limiting...
2024-11-1258 minThe Hotel Investor PlaybookThe Hotel Investing Guide to Operational Excellence | Mike & Nate E4In this episode of the Hotel Investor Playbook, Michael and Nathan dive into the essential topic of hospitality operations, exploring the less-discussed but crucial aspects that drive a thriving hotel business. The conversation reveals how to navigate common operational pitfalls, emphasizing the importance of delivering exceptional guest experiences and building efficient systems. The episode covers a range of topics including the integral role of reviews, leveraging technology, implementing the EOS system, and setting up detailed processes to ensure smooth and scalable operations. Listeners are provided actionable insights and a step-by-step guide on auditing reviews, managing guest experiences, and creating...
2024-11-0558 minThe Hotel Investor PlaybookTransitioning From Investing in STRs Into Boutique Hotels | Kassidy Warren E3In this episode of the Hotel Investor Playbook, Mike and Nate introduce Kassidy Warren, a former corporate executive who transformed his life by diving into the world of short-term rentals and is now purchasing boutique hotels. Kassidy began his journey in 2015, renting out a spare bedroom for $35 per night, and now oversees a $12 million property portfolio across five states. This episode covers Kassidy's evolution from house hacking to becoming a savvy investor, focusing on high-design concepts and memorable guest experiences. Discussions explore the strategic shift from investing in residential STR's to boutique hotels, leveraging properties, financial freedom, and tax-saving...
2024-10-2954 minThe Hotel Investor PlaybookAre Hospitality Investing Mastermind Conferences Worth It? | Mike & Nate E2In this episode, hosts Michael Russell and Nathan St. Cyr delve into the value of attending mastermind conferences and networking events. They reflect on their recent 10-day tour of educational meetups, discussing key takeaways on boutique hotel investing, particularly focusing on operations, deal finding, capital raising, and marketing. The episode highlights the benefits of unique hospitality experiences and effective team building, emphasizing the importance of seeing the highest and best use of spaces. Notable insights include the long-term value of networking with industry experts like Ben Wolff and Devon Towle, the innovative business ventures such as floating homes and...
2024-10-2356 minThe Hotel Investor PlaybookHotel Investing: The Best of Both Worlds | Mike & Nate E1In this episode of the Hotel Investor Playbook, Michael Russell and Nathan St. Cyr share insights into the lucrative world of boutique hotel investments. They recount their journey from real estate investments in single-family homes and vacation rentals to leveraging boutique hotels for high cashflow and significant equity gains. The hosts elaborate on the unique opportunity this asset class presents, including less competition, fewer regulations, and potential seller financing options. They emphasize the artistic and financial fulfillment derived from creating unique guest experiences in boutique hospitality, making it an attractive option for real estate investors seeking both immediate cashflow...
2024-10-1536 minThe Hotel Investor PlaybookTrailer: Welcome to the Hotel Investor Playbook!In this premiere trailer of The Hotel Investor Playbook, hosts Michael Russell and Nathan St Cyr dive into what their new podcast is all about. Get to know the duo behind Malama Capital and Howzit Hostels as they pull back the curtain on their experiences in the world of boutique hotels and experiential lodging properties. Discover why they've chosen this path, the passion that fuels their investment decisions, and what listeners can expect in upcoming episodes. From success stories to actionable strategies, this episode sets the stage for a podcast designed to help you turn your own hotel investment...
2024-09-3002 min