Episodes

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 bookingsWhat makes a...

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 estateHow to gain credib...

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 b...

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 bestHow the “Mamba Mentality” shaped his risk tolerance and executionWhat he learned by making his first deal a ground-up development...

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,...

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 with...

In 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 empire Navigating zoning issues, STR restrictions, and neighborhood pushback What to look for in land: acreage...

Not 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 ...

We'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 disruption The revenue model that turns $100 rooms into $300 cash machines How their guest-first brand became a marketing engine Why “flawed” properties are actually a goldmine for...

You 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 Brian Fish, CEO of Reliance Hospitality, to unpack how third-party operators help investors go from scrappy operators to institutional-level players. Brian shares what most owners get wrong during acquisitions, how franchise agreements really work behind the scenes, and why your ability to scale come...

After 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 b...

In this episode, we sit down with Ian Joseph, founder of Branch, a luxury micro resort in the hills of West Virginia, to talk about building boutique hospitality with a soul. Ian’s not only creating a set of luxury cabins, he’s crafting a guest experience rooted in community, design, and nature. And he's doing it all with a lean team, a USDA loan, and a strategic eye for scale. What You'll Learn: Why Ian pivoted from short-term rentals to commercial micro resorts How he found and secured the...

In 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 ...

In 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...

What 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 L...

In 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 goal How we’ve restructured our team to create more bandwidth Using C...

What 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. W...

What 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 f...

From Olympic Trials to Losing Millions—And Bouncing Back With a Boutique Hotel Empire In 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 hig...

What 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 effecti...

Could 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 numb...

What 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, yo...

“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 us...

Ever 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. 📍 Navig...