The Layover

Inside GuestOS with Jessie Fischer: AI Hospitality, Yosemite & the Future of Guest Experience

In this episode of The Layover, we sit down with Jessie Fischer, founder and CEO of GuestOS, to explore how artificial intelligence is transforming hospitality—not by replacing people, but by giving hotel teams more time to create meaningful guest experiences. Raised in a family that has operated hotels near Yosemite National Park for more than 50 years, Jessie grew up answering phones, calming guests during wildfires and power outages, and learning firsthand what hospitality looks like when nature keeps you on your toes. Today, she’s channeling those experiences into GuestOS, an AI-powered hospitality platform helping hotels automate repetitive tasks while elevating service and personalization. Jessie breaks down how GuestOS is: * Automating repetitive guest inquiries so hotel staff can focus on hospitality, not busywork * Creating customizable AI “teammates” trained on each property’s unique brand and personality * Helping hotels unlock underutilized spaces and create new guest experiences * Using AI to improve communication during emergencies like wildfires and road closures * Supporting outdoor destinations like Yosemite through better visitor information and coordination * Reimagining hotels as hubs for experiences, community, and connection—not just places to sleep The conversation also dives into the future of hospitality tech, overtourism in national parks, outdoor travel, female founders in hospitality, and why the best travel memories almost always come from human connection—not amenities. Whether you’re a hotelier, travel tech founder, outdoor enthusiast, or simply curious about how AI can make hospitality feel more human, this episode offers a thoughtful look at where the industry is headed next.

Building Pink Notebook: Goedele Mangelaars on the Future of Travel Tech

In this episode of The Layover, we sit down with Goedele Mangelaars, founder and CEO of Pink Notebook, an AI-powered travel platform reimagining how trips are discovered, planned, and booked. From growing up across continents to working at companies like Skyscanner and Terra API, Goedele brings a global, data-driven perspective to one of travel’s biggest pain points: too much inspiration, not enough context. Pink Notebook is built to bridge that gap—combining visual discovery, smart curation, and seamless booking into one cohesive experience. Goedele breaks down how Pink Notebook is: * Reducing decision fatigue by narrowing thousands of options into a curated shortlist * Combining inspiration, context, and booking into a single end-to-end platform * Challenging traditional OTAs by focusing on boutique hotels and high-intent travelers * Using AI more like Spotify or Pinterest—surfacing what you’ll love, not overwhelming you with choices * Designing for a world where 80% of travel decisions are driven by women * Pushing back against trend-driven travel in favor of authentic, meaningful discovery The conversation also explores the future of agentic travel planning, the limits of AI trust, and why human curation still matters in a world flooded with content. Whether you’re a frequent traveler, startup founder, or simply tired of clicking through 277 tabs to plan a trip, this episode offers a fresh take on where travel tech is headed—and how to make it work better for real people. Follow Pink Notebook at @pinknotebooktravel for more!

Inside LOST iN with Jon Skogmo: Print Revival, IRL Experiences & The Future of Travel Media

In this episode of The Layover, we sit down with Jon Skogmo, CEO of LOST iN, for an inside look at how the brand is redefining travel media; blending physical guidebooks, digital storytelling, and real-world experiences into one cohesive ecosystem. From betting on print in a digital-first world to building a community that spans social, newsletters, and IRL events, Jon shares why the future of travel isn’t just about where you go—but how you connect along the way. Jon unpacks how LOST iN is: * Leading a resurgence of physical media, with guidebooks designed as collectible, story-driven travel companions * Targeting millennials and Gen Z travelers who prioritize experiences over ownership * Bridging the gap between URL and IRL, using events, pop-ups, and community moments to deepen engagement * Treating travel as the antidote to AI, prioritizing real experiences over digital noise * Building a curated creator network focused on authenticity, not follower count * Expanding globally with 400+ retail locations and growing first-party audience data From vacations to transformational travel trends, this conversation dives into how cultural shifts, remote work, and creator ecosystems are reshaping the way (and the reasons) people explore the world. Whether you’re a traveler, brand marketer, or media operator, this episode offers a candid look at how LOST iN is building a next-generation travel brand rooted in curation, community, and real-world connection. 🌍 Explore LOST iN guidebooks, destinations, and experiences at lostin.com [http://lostin.com].

Inside the Las Vegas Aces with D’Andra Duggans: Sports Travel, Brand Experience & Building a Championship City

In this episode of The Layover, we sit down with D’Andra Duggans, Chief Brand Officer of the Las Vegas Aces, to explore how women’s sports, destination marketing, and live entertainment are reshaping Las Vegas into a global sports travel powerhouse. From championship culture to marquee partnerships, D’Andra shares how the Aces are designing experiences that draw fans far beyond the arena. As sports tourism surges toward a projected $2 trillion global market, the Aces are emerging as a must-see stop on the Las Vegas itinerary—proving that women’s basketball can drive travel, culture, and economic impact at scale. D’Andra breaks down how the Aces are: * Turning championship success into a destination-worthy game-day experience * Partnering with MGM and the LVCVA to integrate Aces games into broader Vegas travel itineraries * Taking a quality-over-quantity approach to brand partnerships and sponsorships * Building player-led storytelling that empowers athletes as creators and media brands * Positioning the Aces as a cornerstone franchise in both the WNBA and Las Vegas’ sports ecosystem * Using CES as a platform for inspiration, innovation, and future-facing fan engagement Whether you’re a sports marketer, brand strategist, or traveler planning your next Vegas trip, this episode offers a compelling look at how the Las Vegas Aces are redefining sports entertainment—and why women’s sports are becoming a powerful engine for tourism and culture. 🏀 Learn More Follow the Las Vegas Aces and their upcoming season to see how championship basketball meets destination-driven storytelling in Las Vegas: https://aces.wnba.com/ [https://aces.wnba.com/]

Inside Black Tomato with Tom Marchant: Transformational Travel, Human Connection & the Future of Luxury

In this episode of The Layover, we sit down with Tom Marchant, co-founder of Black Tomato, the award-winning luxury travel company known for designing deeply immersive, emotionally driven journeys around the world. From backpacking through the Philippines and Brazil to building one of the most influential brands in experiential travel, Tom shares how curiosity, not comfort, has always been the compass. Tom unpacks how Black Tomato has helped pioneer the rise of transformational travel, creating trips that prioritize how travelers want to feel, not just where they want to go. In this conversation, Tom explores: * Why luxury today is defined by thoughtfulness, access, and emotion, not just five-star amenities * How Black Tomato finds meaningful experiences beyond overtouristed destinations * The role of local fixers and human relationships in creating truly personal journeys * Designing family and multi-generational travel that brings people together—without friction * Why AI can support travel planning but will never replace human intuition and trust Whether you’re fascinated by the psychology of travel, seeking deeper experiences beyond the bucket list, or curious how luxury brands stay human in an AI-driven world, this episode offers a thoughtful look at why the most powerful journeys don’t just change where you go—they change how you see the world. 🌍 Discover more about Black Tomato and their approach to transformational travel at blacktomato.com [http://blacktomato.com]. * Website: https://www.blacktomato.com/ [https://www.blacktomato.com/] * Instagram: @blacktomatotravel [https://www.instagram.com/blacktomatotravel] * Tom Marchant on Instagram: @tommymarchant10 [https://www.instagram.com/tommymarchant10/?hl=en] * Gift of Boredom [https://www.blacktomato.com/boredom/] (mentioned in conversation) Destinations and itineraries mentioned: * Iceland: Snorkel and dive between tectonic plates [https://www.blacktomato.com/us/destinations/iceland/our-hip-icelandic-snorkelling-weekend/] * A Journey into Mongolia [https://www.blacktomato.com/destinations/mongolia/a-journey-into-mongolia/] (for campfire cookouts, eagle hunting, and mountain monasteries) * Ultimate Bhutan: A Luxurious & Cultural Retreat [https://www.blacktomato.com/destinations/bhutan/luxury-holiday-in-bhutan/] (spiritually enlightening and as remote as they come) * An Adventure Across Iceland [https://www.blacktomato.com/destinations/iceland/an-adventure-across-iceland/] (for magma chambers, trolls, and geothermal tomato farms) * Switzerland & Italy [https://www.blacktomato.com/us/destinations/italy/luxury-alps-lakes-coast/] (a luxury vacation in the Alps, lakes, and coast) * An insiders guide to the Amalfi Coast [https://www.blacktomato.com/us/inspirations/insiders-guide-to-amalfi-coast/]: Limoncello, sweeping vistas and storied villas