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 Aug 20, 2024
Tuesday Aug 20, 2024
Meet Diana Ossa Sierra, co-founder of D-I-FI, who, along with her husband Josh, is transforming the intersection of architecture, design, and real estate investment in the world of boutique hospitality.
Originally architects and construction managers, Diana and Josh were deeply embedded in their demanding careers until a life-altering event in 2021 made them question everything. The tragic loss of their fathers ignited a fire within them to pursue a different path—one that offered more than just professional success but personal fulfillment and freedom.
In this episode, Diana takes us through their journey, from the initial struggles of trying to fit into the traditional real estate mold to discovering their true passion for creating unique, wellness-focused boutique hotels. We discuss the challenges they faced, including walking away from two major hotel deals that didn’t align with their vision, and how those experiences ultimately led them to their current project in Palm Springs.
Diana shares how they’ve leveraged their architectural expertise to add real value to their projects, the lessons they’ve learned in managing properties across three states, and the importance of finding work that truly excites you. This episode is a must-listen for anyone interested in the future of experiential hospitality and the power of aligning your work with your passion.
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.
Alright friends, without further ado, get ready to meet Diana.
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