Direct booking starts before the trip, and Hyatt's missed targets show how hard that is to execute.
Behind the Stays makes direct booking feel less like a channel strategy and more like a race to reach travelers before intent has fully formed.

Operator-minded stories from modern hospitality.
Behind the Stays mixes founder stories with fast-moving hospitality news analysis. It suits listeners who care how boutique stays get built, marketed, funded, staffed, and discovered.
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Behind the Stays is a hospitality business show built around the people and pressure points behind memorable places to stay. It moves between two modes. In one, the show profiles founders and operators building distinctive hospitality brands, from The Retreat Costa Rica to Death & Co's expansion logic to Nocturne Luxury Villas. In the other, its This Week in Hospitality episodes work like a loose industry roundtable, testing the week's hotel news against real operator consequences. The show is interested in beauty, but it is more interested in what makes beauty survive as a business. That means direct booking, loyalty, social media, brand architecture, franchise limits, OTA dependence, and the cost of scaling without losing soul. Its best moments happen when a big claim gets pulled apart. If social platforms are the new OTAs, then the show asks who owns the moment of intent. If loyalty is not really about points, then it asks what guest recognition should look like. If hotel groups keep adding brands, it asks whether that creates demand or just gives owners more distribution options. The interview episodes bring a more biographical rhythm. Diana Stobo's story turns a health crisis, a mountain property, and wellness positioning into a case study in conviction. David Kaplan's bar story becomes a way to talk about experience design and creative hospitality. Scott Wiseman's move from Accor to Nocturne Luxury Villas opens questions about service infrastructure in private rentals. The show is casual and sometimes chaotic, with interruptions, jokes, sponsor reads, and practical reframing. It does not sound detached from the industry. It sounds embedded in it. That makes the copybook version of hospitality less interesting than the operational one: how guests discover a stay, why they book, what they remember, and what owners can actually control.
Made for: For boutique hotel owners, vacation rental operators, hospitality marketers, travel founders, and listeners who want the business logic behind memorable stays. It also fits anyone tracking how independent properties compete with major hotel brands and OTAs.
What sets it apart: Behind the Stays pairs founder narratives with current hospitality market analysis, so the same feed can move from a personal origin story to a debate about demand creation. Its point of view is unusually operator-focused, especially around direct booking, loyalty, social media, and brand scale.
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…
Based on 6 episodes we listened to · September 2026
It turns boutique hospitality into a clear study of capital, customer acquisition, brand control and the difficult mechanics of growth.
Behind the Stays treats hospitality as an operating business, moving between founder interviews and a conversational industry-news roundtable.
A $12 million hotel becomes $30 million, and suddenly your mood board needs a lender.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Direct booking starts before the trip, and Hyatt's missed targets show how hard that is to execute.
Behind the Stays makes direct booking feel less like a channel strategy and more like a race to reach travelers before intent has fully formed.
A health crisis becomes a founder story about turning wellness expertise into a mountain-sized hospitality bet.
Diana Stobo's route to the Retreat Costa Rica gives the episode a sturdy founder story: a health crisis pushes her toward wellness, and a property decision becomes a serious bet on destination hospitality.
A sharp hotel strategy discussion on loyalty, recognition, and the platforms shaping discovery.
The episode frames hotel discovery as a contest for the traveler's moment of intent. Its core argument is clear: loyalty is shifting away from points and toward recognition, while social platforms are moving closer to the role once held by online travel agencies because they…
A hospitality growth episode on whether social storytelling can scale brand value as much as adding rooms.
The episode frames hospitality growth as a control problem: when a four-property hotel group looks across at a fourteen-property competitor, the real question is what should scale.
A practical look at growing luxury-villa service while preserving the identity of established regional operators.
Scott Wiseman's move from marketing leadership at Accor to CEO of Nocturne Luxury Villas frames a practical question: how can a hospitality brand grow without flattening the businesses beneath it?
A $12 million project becomes a $30 million look at optimism, confidence, and founder endurance.
A $12 million project swelling into a $30 million project gives the episode its business backbone, but the real pull is the temperament behind it.
A grounded look at growing a vacation-rental brand while preserving its identity and leaving room for a future sale.
Gather proposes a middle path for vacation-rental managers who want support without giving up the brands they built. It would maintain the operator's website, booking engine and direct-booking capability, then receive first right of refusal if the manager later chooses to sell…

Odd questions, followed patiently down to the incentives.





Family grief, public questions, and the responsibilities of care.
Will Hardy, a former athlete and actor turned entrepreneur, shares his journey of building the $30 million Trail Hotel on Kentucky's Bourbon Trail.
Andrea Grigore, CEO of Gather Vacations, shares her journey from a finance graduate during the 2008 recession to a key player in luxury hospitality.
Hilton CIO Michael Leitinger told the Destination AI conference in Washington, DC that AI assistants put online travel agencies under "real threat," and the hosts debate whether AI agents will become commissionable like OTAs.
Direct booking gets dragged out of theory and into the lobby.
What is wellness?
A roundtable discussion on the transformation of hotel discovery, the rise of food-led hotels, and the shift from loyalty points to recognition in the hospitality industry.
A roundtable discussion on Hilton and Marriott's latest moves in hospitality, focusing on brand proliferation, distribution strategies, and the battle for booking demand.
Death & Co founder David Kaplan discusses the enduring appeal of craft cocktails and his expansion into boutique hotels.
Hotel F&B shifts from a "necessary evil" to a demand driver as lenders start underwriting restaurants and bars for TREVPAR and local relevance.
"Loyalty is going to go to the company that takes the best care of the guest."
A panel of hospitality podcasters discuss the biggest stories and trends from 2025 and predictions for 2026.
Richard Valtr, founder of Mews, discusses how he built an open API PMS to enable personalized, five-star hotel experiences at scale.
Andreea Grigore shares her journey from a chance meeting at a party to founding Gather, a vacation rental management platform designed to make property management sustainable and efficient.
An interview with the godmother of glamping discussing the state of the glamping industry in 2025, including trends, premiums, and predictions.
Brandon Gore shares the story of building a boutique hotel by hand, including his stressful journey and discovery of rammed earth architecture.