The Hotel Investor Playbook

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 eco...

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...

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 Navigat...

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 s...

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 th...

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 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 acqui...

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 br...

In 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 de...

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...

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 d...

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 $...

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 acquisit...

What do you do when you get fired from your job and get escorted out with a cardboard box? If you’re Sky Mitchell, you build one of the fastest-growing hospitality brands in Canada. In this episode, we sit down with Sky Mitchell, 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 raisi...

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...

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 b...

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 ult...

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...

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 in...

“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 de...

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....

💡 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 ✔️...

🏨 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...

Luxury 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 ✅ W...

Do 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 accountabilit...

What 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&ap...