Episodes

The hotel industry is changing: costs are rising, AI is here, and investors are getting more selective. This week on the Hotel Investor Playbook, we sat down with Bob Rauch, better known as The Hotel Guru. From starting out as a dishwasher to building and selling a 20-hotel management company, then launching Brick Hospitality and managing nearly 1,000 rooms, Bob has seen it all. In this episode, you’ll learn: How to spot hot markets (and avoid the ones that eat your profits)The truth about us...

Where is the hotel market headed in 2026, and how can investors succeed in a challenging environment? This week on the Hotel Investor Playbook, we sat down with Jan Freitag, National Director of Hospitality Analytics at CoStar. With over 30 years of experience analyzing hotel performance data, Jan is one of the most respected voices in the industry. Here’s what you’ll learn: How to use data and analytics to spot opportunities others overlookWhy conviction and strong operations can outperform ...

The most powerful part of a hotel stay isn’t the design or the amenities, it’s the feeling guests take home. That’s the philosophy of Bashar Wali, one of the most candid and creative voices in hospitality, who's spent 30+ years building, operating, and reinventing hotels around the world. In this episode of the Hotel Investor Playbook, Bashar shares: Why “give-a-shit-ability” beats corporate playbooks The power of emotional intelligence in hotel teams The biggest mistakes first-time owners ...

How do you turn a struggling hotel into a profitable asset? This week on the Hotel Investor Playbook, we sit down with Naveed Khan, co-founder of London Rock Partners, a hotel management and advisory firm that oversees everything from branded hotels like Holiday Inn to boutique independents and even a 650-bed hostel in London. In this episode, you’ll learn: Why the first step in turning around a hotel always starts with people, not P&LsThe advantages (and risks) of branded vs. independent...

Few people have left a mark on hospitality like Richard Kessler. He started his hospitality career by helping scale Days Inn into a household name as the early CEO Then he founded the Kessler Collection, one of the leading boutique hotel portfolios in the U.S., which ultimately helped launch Marriott’s Autograph Collection. In this episode, Richard shares the biggest lessons from his 50-year career, including: • How to lead through downturns and find opportunity in distress &nbs...

What if your first hotel deal could be funded almost entirely through Instagram? This week’s guest, Soli Cayetano AKA lattes.and.leases on Instagram, went from barista to building a $13M real estate portfolio in just four years. After exiting her residential investing business, she turned to hospitality and now co-owns a 13-key boutique wellness hotel in Palm Springs that’s already been featured in Forbes, Vogue, and Travel & Leisure. In this episode, you’ll learn: How Soli raised $2.5M i...

What happens when you buy a piece of land on a hunch and decide to build something that could last a thousand years? This week’s guest, Brandon Gore, has one of the most unique paths into boutique hospitality we’ve ever heard. After a career in corporate hotels, he built a name as a concrete craftsman, only to return to his roots in Arkansas with a vision: The Outlier Hotel, a 10-cabin luxury retreat designed with world-class architecture and adventure hospitality in mind. In this episode, you...

Think great marketing is only for big hotels with big budgets? Think again. In this episode, we talk with Steph Weber, a marketing and branding expert who helps boutique hotel and STR owners drive direct bookings. She breaks down how she finds her audience, tells a compelling brand story, and uses limited resources to drive big results. You’ll learn: How to identify your property’s unique selling pointsSimple marketing strategies that work for small hotels and innsWhy guest experience is your...

Think you need a perfect plan to start investing in hospitality? Think again. In this episode, we sit down with Jonathan Mueller, an everyday investor who went from zero experience and a failed multifamily deal to buying a $250K roadside motel and building a growing hospitality portfolio. He didn’t have a background in hotels, didn’t have much of a strategy, and still made it work through pure action, problem-solving, and a willingness to pivot. You’ll learn: Why taking action beats waiting f...

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...