The Hotel Investor Playbook

The Hotel Investor Playbook

Welcome to The Hotel Investor Playbook, hosted by real estate investor and hospitality operator Michael Russell. Michael is the co-founder of Malama Capital and Howzit Hostels, where he has built and scaled a portfolio of boutique hotels, hostels, and experiential lodging properties.

With over $30 million in real estate investments across hospitality, short-term rentals, long-term rentals, and commercial assets, Michael brings a practical, operator-first perspective to hotel investing. On this podcast, he breaks down what it actually takes to move beyond traditional real estate and into boutique hotels, from sourcing the right deals to navigating operations, capital, and risk.

Each week, Michael shares real lessons from the field as he builds toward a $400 million real estate-based business, giving listeners a clear, honest look at the decisions, challenges, and strategies behind the growth. Subscribe and follow along as he documents the journey in real time.

Recent Episodes

View all
The PhD Economist Who Buys Hotels and Turns Them Into Apartments | Alexander Cartwright E93
Aug. 18, 2026

The PhD Economist Who Buys Hotels and Turns Them Into Apartments | Alexander Cartwright E93

Alexander Cartwright is a PhD economist who left a tenured professorship to buy distressed hotels and convert them into workforce housing through his company, HotelSHIFT. His business rests on a simple valuation gap: hotels trade at higher cap rates than apartments because their income is considered less durable, so the same building can be worth dramatically more once it's rezoned and leased as multifamily instead of run as a hotel. If you're looking for a corner of hospitality investing with
Listen to the Episode
Why This Fund Ditched US Real Estate For 18% Appreciation In Portugal | Dan Daly E92
Aug. 12, 2026

Why This Fund Ditched US Real Estate For 18% Appreciation In Portugal | Dan Daly E92

Dan Daly runs a fund that invests in boutique hotels across Europe, and on this episode he makes the case for why, in his view, Portugal beats the US on nearly every number that matters. According to Dan, property there has appreciated roughly 18% year over year versus 1.8% in the US, and a 30-year mortgage runs about 3.5% against 6.5-7% here. That gap, plus a much lower cost per square foot, is why his fund stopped looking at US deals altogether. Instead of buying property, Global Investment P
Listen to the Episode
The AutoCamp CEO: From Five Broken Airstreams to a Hilton Partnership | Neil Dipaola E91
Aug. 5, 2026

The AutoCamp CEO: From Five Broken Airstreams to a Hilton Partnership | Neil Dipaola E91

Neil Dipaola bought five wrecked Airstreams off Craigslist in 2012 to use as affordable housing in a Santa Barbara mobile home park. Today those trailers have grown into AutoCamp, a nine-property outdoor hospitality brand backed by Airstream, partnered with Hilton, and targeting 100 properties and 10,000 rooms within a decade. In this episode, Neil explains how AutoCamp raised close to $300 million to build out its real estate portfolio, why he structured the business as three separate companie
Listen to the Episode
$200 Million Hotel Broker: Why Your Franchise Flag Might Be Capping Your Hotel's Revenue | Chris Kilcullen E90
July 28, 2026

$200 Million Hotel Broker: Why Your Franchise Flag Might Be Capping Your Hotel's Revenue | Chris Kilcullen E90

Chris Kilcullen has spent three decades in hotels, closing more than $200 million in deals as a senior broker at Avison Young. He's also sold franchises, brokered acquisitions for a REIT, and now built his own hotel concept, so he's seen the flag question from every angle. In this episode, he and Michael dig into the real math: why a commodity economy hotel can lose 30 to 40 percent of its value the moment it drops its brand, and why a well-positioned independent or boutique property can out-ear
Listen to the Episode
The $1 Billion Investor: Data Beats Gut Feel By a Million Miles | Neal Bawa E89
July 14, 2026

The $1 Billion Investor: Data Beats Gut Feel By a Million Miles | Neal Bawa E89

He's not a hotel investor. He built his career in multifamily and self-storage, growing a portfolio that peaked near $1 billion across more than 4,000 units. But the way he underwrites deals, ranks markets, and raises capital works across every asset class, hotels included. That's exactly why he's on this show. Data beats gut feel by a million miles. That's his rule, and in this episode, he breaks down the two metrics he checks before touching any deal, the same ones that predict a hotel's pe...
Listen to the Episode
The Travel Influencer With 1.6 Million Instagram Followers Who Became a Hotel Developer | Jake Snow E88
July 7, 2026

The Travel Influencer With 1.6 Million Instagram Followers Who Became a Hotel Developer | Jake Snow E88

Most hotel investors build the product first and spend years chasing an audience to fill it. This guest did the opposite, and it paid off big-time! In this episode, Michael Russell sits down with a former travel content creator who built a following of over a million people, then used years of staying in the world's best hotels to figure out exactly what makes a property worth sharing, and designed his own around it. That audience helped his first Bali hotel hit 80% occupancy in month one and p
Listen to the Episode
View all Episodes