Behind the Stays

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: zach@joinascend.com

Connect with Cameron Resnick: cam@joinascend.com

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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.

Scott is in Sicily, so Zach, Ben Wolff and Edwin Kramer take the docket. Edwin checks in from a new boutique hotel on Spain's Costa Blanca, and Ben is fresh from the glamping show.

The first story: Hilton's CIO says AI assistants have put online travel agencies under real threat, yet he expects personal AI agents to become commissionable channels too. The crew asks what "direct" even means when an agent that never sleeps keeps rate-shopping after the booking is made. Edwin says post-booking shopping could be a bigger disruption than the booking itself. Then Booking.com tightens how much guest data, including phone numbers, it passes to hotels.

Next, Lola, the new AI travel assistant from Kayak's co-founders, wholly owned by Booking Holdings. It has a free tier, a $5 a month membership and a $25 a month VIP plan, and both paid plans need a 12-month commitment. Edwin thinks it could make the OTA stronger. Ben is highly skeptical that anyone will pay up front for perks.

Then Choice Hotels buys RV club Harvest Hosts for a reported $130 million. The crew talks about farm hospitality, RVers who eventually want a real bed, and what IHG and Wyndham do next.

The closer: Europe's new anti-greenwashing rules took effect September 27. Edwin explains why they are hard to police and why hotels may go quiet about sustainability instead.

Plus spice of the week: a hot September in southern Europe, and why this is the moment to experiment.

 

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/

https://roompricegenie.com/
Checkout code for 25% off:
WISH26

 

This Week’s Guest:

Jennifer Barnwell - President, Curator Hotel & Resort Collection
LinkedIn: https://www.linkedin.com/in/jennifer-barnwell-a8689ba/
Explore Curator Hotel & Resort Collection: https://www.curatorhotelsandresorts.com/team/jennifer-barnwell/

Your Host:

Zach Busekrus - Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/

 

Recorded live at the Independent Hotel Show in Miami, Zach sits down with Jennifer Barnwell, President of Curator Hotel & Resort Collection, for a macro read on the independent upscale and luxury segment. Jennifer says performance is finally on an upswing after several muted years, but owners are squeezed by costs on every front: consumer goods, labor, property insurance and especially health insurance, alongside persistent staffing gaps in a 24/7 business. She walks through the three technologies Curator has piloted and now runs across member hotels: overnight cleaning robots for corridors and public spaces, guest texting platforms, and AI voice agents that take basic calls off the front desk. The heart of the conversation is Curator's positioning as a "third way" between the big brands and rep/affiliation companies: an owner-centric, light-touch membership built on vetted vendor deals and cost savings, plus consumer marketing that drives direct bookings. Zach pushes on the distribution question, what it would take for a collection to deliver 10% or more of a property's bookings, and argues that AI search makes this the moment for collections as trusted sources for independents.

https://roompricegenie.com/
Checkout code for 25% off:
WISH26

 

This Week's Guest:

Heidi Zimmer — Founder, Wild Rice Retreat
Connect with Heidi: https://heidi-zimmer.com/
Explore Wild Rice Retreats: https://wildriceretreat.com/

 

Your Host:

Zach Busekrus — Journey
LinkedIn: https://www.linkedin.com/in/zachbusekrus/
Instagram: https://www.instagram.com/behindthestays/

Ben Wolff — Founder of Onera & Oasi
LinkedIn: https://www.linkedin.com/in/ben-wolff/
Instagram: https://www.instagram.com/iambenwolff/

 

Heidi Zimmer closed on her construction financing the day before the country shut down in March of 2020.

Then lumber tripled. She had to cut an entire building from the plan. And the business she'd underwritten, roughly seventy-five percent group retreats and twenty-five percent leisure, opened in 2021 and flipped almost exactly upside down.

Heidi has spent more than thirty years in real estate development, much of it building artist housing and creative spaces around the country. Wild Rice Retreat sits on a hundred and fourteen acres of dense forest on a seventy-foot sandstone cliff above Lake Superior in Bayfield, Wisconsin, about as far north as you can go in this country. The land was once home to a James Beard-nominated restaurant designed by the architect David Salmela. Heidi took one look at it and knew it needed to become a place for healing. She brought Salmela back and built a thirty-one-room retreat that blends Scandinavian and Native American traditions.

What makes Wild Rice so interesting is what Heidi refuses to do. Everyone tells her she needs a pickleball court, Pilates reformers and the latest gadget. She tunes all of it out. There's no menu: food is simply out from ten to noon and five to seven, because guests, especially moms, arrive with so much decision fatigue that not having to choose is the wellness. And every day includes a creativity class, because, as Heidi puts it, in the Native American tradition there's no word for artist. To be human is to be an artist.

In this episode, recorded live at the Independent Hotel Show in Miami with my co-host Ben, we get into her three pillars of nourishment, expression and movement. We get into the twenty-five million dollar expansion that adds seventeen owned homes to the rental pool, and the Nordic spa she's building with a glass-front sauna facing Lake Superior. We talk about why same-week bookings are way up, and why she thinks trees are the most underrated wellness modality there is.

Her father used to say there's no problem a good long walk in the woods can't solve. Heidi built a business on it.

The full squad is back. Royal Caribbean is taking a 50% stake in Sandals Resorts for roughly $3 billion, and the crew breaks down why a cruise line wants an all-inclusive hotel brand. Edwin runs the numbers on who is really serving whose guests, and Scott, who has known the Stewart family most of his life, explains why cruise companies can't build ships fast enough and are coming ashore instead.

Then it's Airbnb's hotel push: just shy of 4,000 hotels on the new listing format, hand-curated and aimed at independent and soft-brand three- and four-star properties. Ben weighs in as an operator who knows the platform well, and Edwin asks what happens to hotels when short-term rental markets get squeezed. From there, Uber's hotel business: Dara Khosrowshahi says the traveler comes to Uber, Uber One has more than 50 million paying members, and the Blacklane deal hints at where a trip super app could go.

The closer: at Skift's first creator summit, IHG and Hyatt said they're giving up control of scripted creator campaigns. Scott says it's six years too late. Ben says social is now the best customer acquisition channel on the planet, and any brand that won't invest in it is choosing to hand its bookings to the OTAs. Plus spice of the week, from an Ibiza rave revival to the difference between building a brand and putting heads in beds.

 

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/

Check out Lodgify claim your exclusive discount: https://www.lodgify.com/behind-the-stays/

Femme House website: https://stayfemmehouse.com/

Femme House on Instagram: https://www.instagram.com/femmehouseaz/

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Vanessa Aguirre was in her bridal era when the idea for Femme House found her. A disappointing experience with her own wedding venue, a travel blogger's eye for what makes a stay shareable, and a hunch that bachelorettes deserved better than what Nashville was offering. So in 2020, with travel stopped, weddings cancelled, and everyone telling her she was crazy, she and her husband Jake bought a house in Nashville and painted it pink.

It worked immediately. Bookings poured in from day one (her first mistake: pricing too low), and within a month the goal became property number two in Scottsdale, the country's second-largest bachelorette market. 

 

Today Femme House runs three properties across the two cities, each designed around one guest: the bride. Heart-shaped mini golf, beauty bars built for getting ready together, a shimmer wall that saves every group the $800 they would spend renting one. Every detail has to be both functional and scroll-stopping.

In this episode, Vanessa gets into the strategy behind the aesthetic: why picking one avatar beats appealing to everyone, why "copy the top-performing house" is the worst advice in short-term rental investing, how Nashville and Scottsdale bachelorettes behave completely differently, and how the communal "take a penny, leave a penny" decor culture became part of the brand. She also shares the Airbnb suspension scare, triggered by a neighbor's New Year's Eve fireworks, that pushed her into direct booking, first reluctantly and then happily with Lodgify.

Her advice for anyone building a themed stay: go all the way in.

—

 

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.

Fresh off Independent Hotel Show Miami, Zach and Ben break down two days of conversations with eight owners, operators, and investors from across independent hospitality.
Before the full interviews roll out on This Week in Hospitality, this is the recap — the ideas that kept surfacing across every mic session, the moments that caught us off guard, and what these conversations say about where independent hospitality is actually headed.

Whether you own a property, back one, or build for the people who do, consider this your shortcut to what the industry's sharpest independents are thinking right now.

 

 

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/