Podcast

Zen and the Art of Real Estate Investing with Jonathan Greene

179: Turning Short-Term Rental Success into Boutique Hotels with Blake Dailey

Boutique hotels have similarities to short-term rentals, but there are some distinct differences, and today’s guest is an expert in this asset class.

On this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Blake Dailey, a real estate investor who began investing while active duty military and carved out a successful career as an investor post-military service. Blake started his investing career with a single Airbnb more than five years ago. Today, his business has 30 employees and 150 short-term rental units. He is focused on boutique hotels these days and just finished hosting Boutique Hotel Con, a conference for boutique hotel owners.

Jonathan and Blake start their conversation by exploring how he began investing while still on active duty in the military, what Blake learned about systems and processes in the Air Force, and the lessons he learned early on in his investing career. You’ll hear the importance of relationships in finding deals, taking advantage of your VA loan benefits as military or former military, and taking action even if you fear failure. They cover how to create a good deal, what makes investing in boutique hotels different from short- or long-term rentals, and where Blake finds hotels to invest in and finance. Finally, Blake shares the demographics he uses to pinpoint a good buy, the amenities he adds to properties, and what his Boutique Hotel Mastermind can teach you.

If you’ve ever looked at a rundown hotel and wondered if you could turn it into a thriving asset, you won’t want to miss Jonathan’s conversation with Blake Dailey.

In this episode, you will hear:

How Blake Dailey began investing in real estate while still on active duty in the military
What the Air Force taught Blake about systems and processes to scale his business
The lessons he received from wholesaling at the beginning of his real estate investing
The importance of relationships and networking in creating good deals
Taking advantage of VA loans to start investing
Being humble enough to acknowledge that you don’t have all the answers, taking action, and being willing to fail
Finding ways to make good deals through your lens and experience
The different strategies Blake incorporates with his boutique hotel operations
Blake’s definition of a boutique hotel: small, unique, and independent
Where he finds hotels to invest in, how he finances them, and transforms them into income producers
The demographics and geography Blake uses to pinpoint a good buy
Amenities and the ability to add those to a property
Blake’s Boutique Hotel Mastermind course and his advice for new investors

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