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 Partnership invests in the operating companies that run boutique hotels in Portugal, hotels that are already refurbished, licensed, and cash-flowing but undermanaged. Dan walks through the specific leaks he looks for (unclaimed cleaning fees alone can run $25-35 a night per unit) and the five-year path the fund creates to permanent EU residency for investors and their families.

We also get into managing a portfolio spread across the US, Portugal, Madeira, and Andorra from a laptop in Los Angeles, and where Dan sees his exit.

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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 companies (real estate, brand, and operations) instead of one, and how that decision now gives him multiple ways to grow or eventually sell the brand. We also get into how the Hilton partnership actually works, why the AutoCamp team rejects the word "glamping," and how everyday investors can now buy equity in the brand for as little as $1,000.

If you're building a hospitality brand and thinking about how to structure it for growth or an eventual exit, this is the playbook.

Exclusive Listener Offer: Save 20% at all AutoCamp locations when you book through the link below:

AutoCamp | Nature's Boutique Hotel

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Chris Kilcullen has spent three decades in hotels, closing more than $500 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-earn a branded one because it isn't capped by what guests expect to pay for a templated room. They also cover how Hilton and Marriott are using new soft brands to pull independent hotels back into their loyalty ecosystems, the F&B concept Chris is building to fix the one thing every guest complains about, and why some aging economy hotels are worth more converted into workforce housing than they are as hotels.

If you found value in this episode, take 30 seconds to leave us a review here. It helps more people find the podcast and keeps us bringing on great guests.

Connect with Michael on Instagram or LinkedIn.

Email Us at info@hotelinvestorplaybook.com

Visit the Hotel Investor Playbook Instagram

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