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

Zen and the Art of Real Estate Investing

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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If you enjoyed this episode, we've created a PDF that has all of the key information for you from the episode. Just go to the episode page at https://zenandtheartofrealestateinvesting.com/podcast/179/ to download it.

Supporting Resources:

Blake Dailey’s website - blakedailey.com

Find Blake on YouTube - www.youtube.com/@BlakeDailey

Connect with Blake on Instagram - www.instagram.com/blakejdailey

Attend Boutique Hotel Con - boutiquehotelcon.com

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

TikTok - www.tiktok.com/@trustgreene

Zillow - www.zillow.com/profile/StreamlinedReal

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/streamlinedproperties

Email - [e-mail]

Episode Credits

If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.