Behind the Stays

If you’ve ever dreamed of running marketing for one of the most iconic resorts in the Caribbean—or just wanted a peek behind the scenes of what it actually takes to make a destination “hot”—today’s episode is for you. My guest is Jason Kycek, the Senior Vice President of Sales and Marketing at the legendary Casa de Campo in the Dominican Republic. And while Jason’s resume includes time with some of the most respected names in hospitality, what makes this conversation so refreshing is that Jason is a marketer through and through. A builder. A thinker. A tinkerer. We talk about what it means to market an independent luxury resort in today’s hyper-digital world. Why social media has become the new front door. How culinary strategy, entertainment programming, and influencer partnerships are being reimagined. And how the smartest marketers are building brands and balancing performance expectations—sometimes on a shoestring budget. Jason also shares his journey—from Wisconsin to the DR—and what he’s learned leading marketing across both institutional hospitality groups and independently owned gems. 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 the Journey Alliance. 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.

What started as a furlough-era side project on Instagram is now a full-fledged media brand reaching over 400,000 boutique hotel obsessives — and Brandon Berkson, founder of Hotels Above Par, is just getting started. In this episode, we dive into: Brandon’s unshakable obsession with boutique hotels (he used to play hotel as a kid — not kidding) How a background in PR shaped his approach to storytelling, strategy, and aesthetic curation The origin story behind Hotels Above Par — and how a single Instagram caption became the launchpad for a globally respected travel media platform Why partnering with tourism boards (not just hotels) is a win-win-win How paid partnerships, affiliate bookings, and Substack newsletters drive real revenue (this isn’t just a vibes operation) Why he’s bullish on newsletters, hospitality humans, and high-touch check-ins — even as AI eats media We also unpack Brandon’s POV on: What most independent hotels are still getting wrong on Instagram Why newsletters are having a renaissance moment (and how hoteliers should use them) How journalists are evolving into modern creators (and what makes them more trustworthy than traditional influencers) What makes a travel giveaway actually work — and why you’re probably doing it wrong This one is for the independent hoteliers fighting the good fight, the brand builders playing the long game, and the travelers who crave places with soul. Follow Hotels Above Par on Instagram Follow Brandon on LinkedIn Explore the Hotels Above Par Website 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 the Journey Alliance. 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. 

Mike Weiss and Ben Weinberg, co-founders of Trailborn, discuss their ambitious journey shifting from finance to creating an experience-driven hospitality brand. They explore the untapped potential in lesser-known markets and the benefits of vertical integration. The duo shares how their partnership with Marriott enhances their reach while maintaining their core values. They delve into the intersection of AI and personalized service, arguing that technology will elevate, not replace, the human touch in hospitality.

Cory Schisler isn’t just building beautiful hotels and restaurants — he’s rethinking what hospitality actually feels like. He’s worked with brands like Proper and Viceroy, co-founded The Madrona in Healdsburg, and has a sharp eye for the subtle — and not-so-subtle — ways hospitality has evolved (and where it still needs to catch up). In this episode, we unpack: – The early experiences that shaped Cory’s hospitality worldview – How to balance timeless service with modern guest expectations – The tech that actually enhances hospitality (and the kind that kills it) – Why QR code menus might signal the beginning of the end – What’s next: the rise of micro-resorts and the white space between STRs and hotels Cory also shares how he approaches concept development, the difference between good and great creative partners, and what it really takes to build a team culture where guests feel seen — and staff feel proud. This one’s packed with insight for anyone thinking about the next generation of hospitality brands. Learn more about Cory here. Explore The Madrona 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 the Journey Alliance. 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. 

Before founding creative studio Corner Booth, Carolyn co-founded Casetta Group, the acclaimed boutique hospitality brand known for transforming forgotten roadside motels into soulful, design-forward stays that actually reflect the communities they’re in. But her journey started far from the boardroom — as a cocktail server at the Ace Hotel in New York, where she first experienced the magic of what a hotel could be when it’s built with intention and feeling. In this conversation, Carolyn unpacks how her background in the art world shaped her creative vision, how she approaches brand-building from the inside out, and why some boutique hotels manage to feel deeply personal — while others fall flat. You’ll hear her thoughts on balancing timelessness with trendiness, her approach to embedding local artists and narratives into each property, and what she’s learning as she advises clients across the U.S. and Europe through her studio. Plus: The real reason the front desk might be the most important brand ambassador of all Why copy-paste design is the death of boutique hospitality How to create a “microcosm of the community” — even in a space you didn’t build from scratch Her thoughts on parent brands vs. standalone hotel brands — and where Cassetta fits in The importance of building with soul — and what gets lost when you cut the “extras” If you’re building a hospitality brand or dreaming up your next project, this episode is a masterclass in curating space, story, and soul. Connect with Carolyn on LinkedIn Learn more about Corner Booth  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 the Journey Alliance. 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. 

Khalid Meniri didn’t come from hospitality — but maybe that’s exactly why he was able to see its most obvious blind spot so clearly. A designer and technologist by trade, Khalid is the founder of Selfbook, the beautifully elegant booking platform that’s quietly powering the next generation of high-end hotels. In this episode, you’ll hear the remarkable story of how a glass cube on Fifth Avenue (yes, the Apple Store) first inspired Khalid’s obsession with design — and how years later, that obsession led him to reimagine the broken booking experience plaguing even the most beautiful hotels. We unpack: Why the legacy booking flow is fundamentally broken — and why most hoteliers don’t even realize it How Selfbook is thinking about dynamic pricing, personalized rates, and the future of “invisible tech” Why the most exciting guest journeys of the next decade won’t start on a hotel website — they’ll start in a chat window And how Selfbook’s new partnership with Perplexity could reshape hotel discovery at the point of inspiration If you care about hospitality tech, design-led products, or the future of direct booking, this is a must-listen. Learn more about Selfbook 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 the Journey Alliance. 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. 

Steve Carran never set out to become one of the most recognized voices in hospitality media. But what started as a scrappy experiment to engage hoteliers during his time in sales has now blossomed into The Modern Hotelier — one of the industry’s most beloved podcasts and a new video media brand that’s putting a fresh lens on hospitality storytelling. In this episode, you’ll hear the fascinating backstory behind how Steve and his co-host David Millili launched the podcast, how they bought it back from a startup, and how it has completely reshaped Steve’s career. We also dive into the biggest trends he’s seeing across the hotel industry — from how AI and design are converging to address labor shortages, to the rise of "bleisure" lobbies, to why apartment-style hotels like Mint House are quietly winning the loyalty of the next generation of travelers. Plus: - Why hotel lobbies are becoming the new coworking spaces - How podcasts have become the secret weapon for hospitality networking - Why giving guests a choice in how they interact with your brand is the future of service - Steve’s vision for the Modern Hotelier Media group — including their "MTV Cribs"-style hotel video tours If you’re building a hospitality brand or just love geeking out on where the industry is headed, this episode is for you. Connect with Steve on LinkedIn Listen to The Modern Hotelier   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 the Journey Alliance. 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.

Ari Heckman, the Founder & CEO of Ash, shares his journey of redefining hospitality. Growing up in Providence sparked his love for transformative spaces. He discusses how modern travelers crave more than design—they seek stories and experiences that resonate. Ari emphasizes the importance of blending aesthetics with financial sustainability and innovative storytelling in boutique hotels. His insights on developing unique hotel narratives and engaging customer loyalty redefine what it means to create memorable guest experiences.

What if the future of storytelling isn't about bigger platforms — but sharper taste? What if the real shift happening in media isn't just economic... but moral? Today, you’re about to meet Rafat Ali — founder and CEO of Skift, one of the most respected travel media brands in the world. But his story didn’t start there. Rafat grew up in India, a shy kid who stuttered — and somehow rewrote his future with nothing but words and a relentless eye for what others missed. He went from studying engineering to working for tech media icon Jason Calacanis during the first dot-com boom...to later building Skift into a brand so trusted that today, CEOs and world leaders cross conference halls just to get a bro hug from him. In this conversation, Rafat shares why legacy media is collapsing, what too many creators get wrong about influence, and how AI and independent media are re-drawing the map faster than most realize. We talk about why design — not data — will be the real differentiator in the next chapter of content. We dive into the hidden risks of "audience capture" — and why building something truly enduring requires the courage to be misunderstood for a while. And we explore why Rafat believes the next great media empires won't be built by corporations — but by people, building with instinct, action, and radical authenticity. If you care about the future of media, if you're trying to build anything magnetic, or if you just want a rare look inside the mind of one of the industry's true visionaries...you're in the right place. 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 the Journey Alliance. 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. 

When the COVID-era short-term rental boom hit, a new class of creators quietly redefined hospitality marketing — and today, three of the best in the business join me for a conversation you won't want to miss. In this episode, I sit down with Hayden Hughes, Nicky Hughes, and Mike Iannetta — three pioneers who helped transform treehouses, A-frames, and glamp-sites from hidden gems into viral, booked-out brands. We unpack how they redefined marketing in the short-term rental world, where the future of creator-driven hospitality is headed next, and why they’ve partnered to launch a new guided course to help hospitality brands partner with the right creators. We get into it: Why short-form video changed everything for independent operators What still actually works on social today — and why trends alone won’t save you Why UGC (user-generated content) isn’t enough anymore — and what’s replacing it The hidden burnout creators are facing, and how the next generation of hospitality marketing will be built differently The big opportunity no one's talking about (yet) for boutique hotels and micro-resorts How the best operators are thinking differently about working with influencers And why creators who want to build real businesses are starting to think beyond content You'll also hear the story behind the Journey More Collective, a potential new playbook for scaling authentic creator-driven marketing and get all the details on the value of The STR Influencer Guide Hayden, Nikki, and Mike just released.  If you're an operator wondering how to actually work with creators (the right way) — or a creator dreaming about building a business with staying power — this one’s for you.  Oh, and if you’re interested in accessing The STR Influencer Guide for Operators, you can do so in the show notes below! Alright friends, without further ado, get ready to meet Mike, Nikki, and Hayden.  Purchase The Influencer Guide Connect with JourneyMore Connect with Mike from Strive Hospitality (MikeWillTravel) Watch a Roundtable Discussion with Zach, JourneyMore, Mike, and other Unique Stay Builders 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 the Journey Alliance. 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 joinjourney.com/alliance.