From Air Force Officer to Hospitality Entrepreneur: Why Blake Dailey Thinks More Airbnb Hosts Should Become Boutique Hoteliers

Meet Blake Dailey — a former Air Force officer turned boutique hotel entrepreneur.

Growing up, Blake dreamed of being in the NFL. And while that never came to fruition, his love for sports instilled in him a sense of discipline and determination that would later fuel his entrepreneurial spirit.

After a stint playing college football, Blake's interests shifted toward business, eventually leading him to discover his passion for real estate and hospitality.

In this episode, Blake and I delve into his incredible journey from serving in the Air Force to becoming a successful hospitality entrepreneur. We explore how his initial investments in real estate and short-term rentals laid the foundation for his entry into the boutique hotel space.

In this conversation you’ll learn:

• How Blake's early investments and entrepreneurial mindset led him to the boutique hotel industry.
• The biggest differences between owning and operating short-term rentals and owning and operating boutique hotels
• The massive opportunity that exists to reimagine outdated motels and transform them into boutique hotels
• Why entrepreneurs who’ve figured out how to host well shouldn’t be scared of graduating from STRs to boutique hotels
• Blake's views on the emerging trends in hospitality and the advantages of a regional focus for portfolio development
• And so much more.

Follow Blake on Instagram

Learn more about Boutique Hotel Con

This episode is brought to you by Hudson Creative Studio — the leading web design agency for vacation rental managers.  Hudson Creative  is offering a special deal for Behind the Stays listeners. When you mention Behind the Stays during your discovery call, you’ll get 10% off any service level option.

If you’re serious about taking your hospitality brand to the next level, head over to HudsonCreativeStudio.com/behindthestays. Trust me, Eli and his team will make your website something truly special. 

And don’t forget to listen to our series, "Unlocking the Secrets of Successful Hospitality Websites," which we’ll link in the show notes below, for a deep dive into what makes these guys the best in the biz.

Want to book a consulting brainstorm with Zach?

Send him an email directly at zach@staywatch.ai or complete this payment link and get immediate access to his schedule where you can book some time with him!

About the Show

Behind the Stays is brought to you by StayWatch — the internet's best resource for deals on Airbnb, Vrbo, and Booking.com. You can subscribe, for free, at www.staywatch.ai

Behind the Stays is hosted by Zach Busekrus, Co-founder of StayWatch, you can connect with him on Twitter at @zboozee or on LinkedIn.