The Layover

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 busyworkCreating customizable AI “teammates” trained on each property’s unique brand and personalityHelping hotels unlock underutilized spaces and create new guest experiencesUsing AI to improve communication during emergencies like wildfires and road closuresSupporting outdoor destinations like Yosemite through better visitor information and coordinationReimagining hotels as hubs for experiences, community, and connection—not just places to sleepThe 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.

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 shortlistCombining inspiration, context, and booking into a single end-to-end platformChallenging traditional OTAs by focusing on boutique hotels and high-intent travelersUsing AI more like Spotify or Pinterest—surfacing what you’ll love, not overwhelming you with choicesDesigning for a world where 80% of travel decisions are driven by womenPushing back against trend-driven travel in favor of authentic, meaningful discoveryThe 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!