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Behind the Stays
Behind the Stays
Author: Zach Busekrus
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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.
And I’m your host, Zach Busekrus, Head of the Journey Alliance. Alright friends, enjoy the show!
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.
And I’m your host, Zach Busekrus, Head of the Journey Alliance. Alright friends, enjoy the show!
395 Episodes
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This Week's Guest:
Alex Cabañas
Executive Chairman, Pyramid Global Hospitality
Founder and CEO of Astound Ventures
https://astound-ventures.com/
What happens when the hotel front desk disappears, but hospitality gets more personal?
This week, Zach Busekrus, Ben Wolff and Edwin Kramer are joined by Alex Cabañas, executive chairman of Pyramid Global Hospitality and founder and CEO of Astound Ventures, for a conversation about the changes that could actually improve hotel margins.
Alex explains why he's investing in hospitality's own problems, from energy management and distributed power to the workflows that keep hotel teams buried in admin. His test for innovation isn't whether it sounds impressive. It's whether it helps owners make money and frontline staff do their jobs better.
They explore a future with lobby hosts instead of agents stuck behind screens, AI tools that put repair answers in an engineer's hand, and automation that connects sales contracts with banquet operations. They also ask what hotels should build themselves, what they should buy, and who has time to sort through the endless startup pitches.
Then the conversation turns to Expedia's rate-parity lawsuit. Ben explains why his direct guests generate higher average daily rates without a lower direct price, while Alex challenges the parity model and considers what AI-driven recommendations could mean for intermediaries.
Finally, Minor Hotels' Life Longevity concept sparks a debate about wellness beyond the stay. Should hotels collect guests' health data, connect with their wearables, or leave diagnostics alone? Alex closes with a different vision of personalization: guests control their data and share it when they want a better experience.
Your Hosts:
Zach Busekrus — Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/
Scott Eddy — Global Travel & Hospitality Expert @MrScottEddy
LinkedIn: https://www.linkedin.com/in/mrscotteddy/
Instagram: https://www.instagram.com/mrscotteddy/
Ben Wolff — Founder of Onera & Oasi
LinkedIn: https://www.linkedin.com/in/ben-wolff/
Instagram: https://www.instagram.com/iambenwolff/
Edwin Kramer — Luxury Hotelier Consultant & Former GM
LinkedIn: https://www.linkedin.com/in/edwinckramer/
Instagram: https://www.instagram.com/edwinkramer/
This Week’s Guest:
Shawn Cioto - Vice President of Operations, Dovetail + Co
LinkedIn: https://www.linkedin.com/in/shawn-cioto-914264b/
Your Host:
Zach Busekrus - Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/
Shawn Cioto, VP of Operations at Dovetail + Co, explains why the owner of seven hotels is taking management in-house: large management companies often miss the small, on-brand details that make independent lifestyle hotels special, from coffee sleeves and key cards to scent, lighting and music. He describes how Dovetail decides between growing its Wayfinder brand (Waikiki, Newport and Bishop) and launching new concepts like its high-design pod hotel, and the whirlwind three-to-four-week takeover of Collective Retreats in New York. With guest acquisition costs climbing through OTA commissions, accelerators and paid media, Shawn's focus is monetizing guests once they're on property. One example is adding a casual second restaurant concept at a remote hotel so guests stay the second night instead of leaving for dinner. He talks about leaning on specialist marketing partners, a creative director and a brand lead, a viral video with their Catskills pizza chef, and surprise-and-delight touches for kids like Tiny the Turtle. With co-host Ben, he digs into balancing brand standards with fun content: standardize back-of-house processes, never the soul of the hotel.
Explore Ascend: www.joinascend.com
Connect with Zach Resnick: [email protected]
Connect with Cameron Resnick: [email protected]
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Follow Behind the Stays on Instagram: https://www.instagram.com/behindthestays/
Connect with Zach Busekrus: https://www.linkedin.com/in/zacharybusekrus/
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Zach Resnick could show business owners how to get far more value from their miles and points. The problem? Even people who paid for the advice often didn't have time to follow it.
That lesson helped turn Easy Point into FlyFlat, and eventually Ascend, a membership travel concierge that handles flights, hotels, and trip changes through WhatsApp. In this episode, Zach and Cameron Resnick explain why better deals got customers in the door, but having someone available when travel goes wrong became the deeper value.
The two share a last name, but aren't related. They met in the Points Guy's Facebook group and built a business out of their shared obsession with understanding travel's rules, rewards, and workarounds.
We get into the shifting relationship between airlines, hotels, credit card companies, and travelers. Cameron explains how transferable points created a kind of free agency. Zach argues that personal agents and concierges could become the relationship travelers trust most. Cameron offers a different view: geography and access to real-world experiences still give travel brands something hard to replace.
For hotel owners, Cameron's wedding story brings the discussion home. He helped guests book around thirty rooms at the Grand Hyatt Kauai using points, but says the hotel missed the opportunity to build a relationship with the group and earn more of their spending.
We also talk about the growing competition for award seats, using points to keep travel options open, and why a great booking experience means little if nobody can help when the trip breaks.
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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.
Your host is Zach Busekrus, Head of Growth at Journey. If you are a hospitality entrepreneur who has a stay, or a collection of stays with soul, we’d love for you to apply to join our Alliance at journey.com/alliance.
Sponsored by:
Modbeans Coffee
Code for 15% off: BTS15
https://modbeans.co/bts
Sponsored by:
https://www.lake.com/partners/behind-the-stays
Michael Wolf thought his career would be in government. He spent every summer in Washington, DC, and wanted the FBI. Then Bain came to campus, and he took a detour that turned into 15 years of startups.
Today he is the CEO of ResortPass, the world's largest marketplace focused on getting hotels more revenue from day guests. The idea starts with perishable inventory: hotels have mastered revenue management for the room, but an empty pool, fitness center or spa today is revenue that never comes back. ResortPass now works with nearly 3,000 hotels, sent a million people to hotels this past summer, and about 40 percent of its hotel partners are independents. More than 95 percent had never offered day access before.
In this episode, Michael explains why the day guest is the same guest who books an overnight room, just for a different part of the stay. We talk about why ResortPass often performs best when a hotel is at high occupancy, how the company built its own system of record because a PMS has no place for a day guest, and why ancillary revenue feels like a win here and a penalty in the airline world.
He also shares how premium hotels use ResortPass to test new products, why the biggest results come from hotels with an internal champion, and his contrarian view on how little innovation there is in an industry this size.
If you run a property with a pool, a spa or a gym that sits quiet some days, this one is for you.
This Week’s Guest:
Michael Wolf - CEO of ResortPass
LinkedIn: https://www.linkedin.com/in/wolfm/
Your Host:
Zach Busekrus - Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/
This Week’s Guest:
Dina Belon-Sayre - President, Staypineapple Hotels
LinkedIn: https://www.linkedin.com/in/dinabelon/
Explore Staypineapple Hotels: https://www.staypineapple.com/
Your Host:
Zach Busekrus - Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/
Dina Belon-Sayre, President of Staypineapple Hotels, opens with a story from a Portland snowstorm when she waited tables herself, fed a stranded hotel and received a thank-you check from a guest. Her point: any Staypineapple employee is empowered to make the same call. She traces her unusual path from theater, psychology and criminal justice studies through hotel design, construction and a decade in sustainability consulting, to spotting a five-story painted pineapple from her Seattle office window and joining the company ten years ago. She rose from director of real estate to president. Dina explains the upside of a playful, edgy brand (the "Naked Experience," no navy blazers or scripts) and the occasional offended guest, and why it's fine not to be for everyone. She describes hiring for emotional intelligence, critical thinking and a willingness to be authentic. On growth, she notes owners are risk-averse, Staypineapple hasn't franchised without management because service is the brand's through-line, and the company may package tools for other independents. Her soapbox: AI and LLM booking could run over independents within 18 months, and collections may need to become their AI intermediary at a fair cost.



