Welcome to Behind the Stays — a podcast that shares the stories behind your favorite boutique hotels, short-term rentals, and hospitality brands and the hosts, operators, and entrepreneurs who’ve brought them to life. Every Tuesday and Friday you’ll meet the military veterans, retired flight attendants, tech entrepreneurs, school teachers, single moms, hoteliers, and real estate investors who are all, in their unique ways, shaping the future of travel and hospitality. Discover how these visionaries — from all over the world — have built stunning landscape hotels in the mountains, designed bohemian bungalows on the beach, erected eclectic off-grid and nature-immersed escapes, and so much more. Behind the Stays is brought to you by Journey — a first-of-its-kind loyalty program that brings together an alliance of the world’s top independently owned and operated stays and allows travelers to earn points and perks on boutique hotels, vacation rentals, treehouses, ski chalets, glamping experiences and so much more. Behind the States is hosted by Zach Busekrus, Head of the Journey Alliance.
Episodes
Tuesday Jul 30, 2024
Tuesday Jul 30, 2024
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- The massive opportunity that exists to reimagine outdated motels and transform them into boutique hotels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.
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.
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