The Hotel Investor Playbook
Welcome to The Hotel Investor Playbook, hosted by real estate investors and hospitality experts Michael Russell and Nathan St Cyr. As the founders of Malama Capital and Howzit Hostels, Michael and Nathan have a wealth of experience in owning and operating boutique hotels, hostels, and other experiential lodging properties. With over $30 million in real estate investments, including short-term rentals, long-term rentals, commercial retail, and hospitality properties, they bring a unique perspective on how to turn passion-driven investments into financial freedom.
In this podcast, they share their roadmap for transitioning from traditional real estate investments to boutique hotels, offering listeners the insights and strategies needed to succeed in this niche market. Whether you're looking to learn about identifying the right property, managing operations, or understanding the financial complexities of boutique hotel ownership, The Hotel Investor Playbook has you covered.
Join Michael and Nathan each week as they document their journey towards building a $400 million real estate-based business and bring you along for the ride. Subscribe now and start turning your real estate investment dreams into reality.
Episodes
56 episodes
How to Replace a Six-Figure Job with Boutique Hotel Investing | Tim Ensmann E55
Ever 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-mi...
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50:15
Real Estate Syndications 101: How Investors and Operators Actually Get Paid | Michael Russell E54
Ever 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 ...
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24:26
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What It Really Takes to Buy Your First Hotel in 90 Days | Jacobo Hernandez E53
When 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,...
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54:41
Building a Lifestyle Hotel Brand in Costa Rica | Bill Graf E52
We’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 hospitali...
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58:57
The “Hotel Guru” on Where to Invest Next & How to Fund Deals | Bob Rauch E51
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 dishwashe...
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57:26
Why 2026 Looks Rocky for U.S. Hotels And Where Smart Investors Can Hit Big | Jan Freitag E50
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 ...
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46:51
How to Craft a Hotel People Will Actually Remember | Bashar Wali E49
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, ...
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1:03:06
What Makes a Hotel Succeed or Fail? | Naveed Khan E48
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...
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49:09
From CEO of Days Inn to Launching Marriott’s Autograph Collection | Richard Kessler E47
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 CEOThen he founded the Kessler Collection, one of the leading boutique...
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1:06:00
How To Use Social Media To Raise Capital And Find Deals | Soli Cayetano E46
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 exi...
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55:55
Building Hotels That Last the Test of Time | Brandon Gore E45
Most 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 Ho...
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51:35
The Marketing Playbook Every Small Hotel Owner Needs | Steph Weber E44
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 ...
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51:16
The Beginner's Guide To Building Wealth In Hospitality | Jonathan Mueller E43
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 ...
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43:43
Hotel Marketing Decoded: What Every Owner Needs to Know | Anthony Chiaravallo E42
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 hot...
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44:59
Syndication Simplified: The Strategy That Builds Generational Wealth | Desiree Doubrox E41
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 ...
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52:10
A Masterclass In Experiential Hospitality With The Bolt Farm Treehouse Founders | Tori and Seth Bolt E40
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, an...
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54:26
$187M Hotel Portfolio by Age 30: How to Choose the Right Deals, Brands, and Ops Model | Sujay Mehta E39
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 peopl...
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1:10:59
Turning Passion into Profit in Rural Hospitality | Dave Cook E38
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.<...
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44:03
Bootstrapped Hospitality: Scaling Your Hotel Portfolio Without Major Capital | Austin Phippen E37
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 Cha...
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37:22
Building a Scalable Outdoor Hospitality Brand Through Franchising | Brian Linton E36
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...
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1:00:46
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How to Know If Your CPA Is Helping You or Holding You Back | Kelly Tate E35
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 hospi...
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51:11
Why Hostels Are an Untapped Investment Opportunity in the U.S. | Mike & Nate E34
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 hospitali...
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36:54
The Strategic Power of Third-Party Hotel Management | Bryan Fish E33
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,...
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45:22
He Managed $320M for a Family Office - Then Walked Away to Build His Own Empire | Reilly Brennan E32
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 Rei...
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47:12
Building a $6M Micro Resort with Only 3% Down Using a USDA Loan | Ian Joseph E31
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 financ...
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47:42
