Everything AI in Travel

• What happens when a hardcore real-estate operator, fund manager, and property manager rebuilds a vacation rental PMS from the ground up with AI at the core?

  In this episode of the Everything AI in Travel podcast, we dive deep into the vacation rental world and the fast-changing landscape of property management systems (PMS) with guest Shaha, founder of Boom, an AI-native operating system for vacation rental managers.From Miami, Shaha shares how he went from doing hundreds of millions in real-estate deals to “accidentally” building a vacation rental management company—then vertically integrating management, construction, cleaning, and a $50M fund—before spinning out the tech and ultimately selling his management business to Casago. Today, that same tech powers Boom, now live in 20 countries across five continents.We talk through: What PMS looked like in 2017 – basic channel managers and unified inboxes – and why that wasn’t enough for serious operators Why traditional PMS + a dozen disconnected tools (pricing, tasks, guest comms, accounting, etc.) breaks down—and how Boom’s “business as software” view ties it all into one data model How AI agents can only work if all the operational data is structured and connected (cleaning, tasks, GPS, inspections, payments, owner P&L, trust accounting, reviews and more) How Boom is already automating 80% of guest communication, and what true agentic AI looks like in property ops Why their ICP starts at 50+ properties, what they’re seeing from leading operators, and how they’re rolling out globally The future of OTAs, trust and discovery – from filter-based search (“Miami, Dec 23–Jan 1, max $600/night…”) to open-text intent (“I want a 2-hour flight, kid-friendly activities within walking distance, ocean view, pet-friendly”) – and how LLMs will sit between guests and inventoryWe also cover Boom’s recent $13M Series A, backed by heavyweights including the former CEO of Hilton, major real-estate families, and top vertical SaaS founders—and why combining deep ops knowledge with frontier AI talent is their core edge.If you:Run a vacation rental management company (50+ doors and up)Work at a PMS, channel manager, or OTA and want to see where the puck is headedAre thinking about how agentic AI will reshape operations, distribution, and guest experience…this episode is a masterclass in where vacation rentals + AI are going next. GuestShaha – Founder, Boom (AI-native PMS / operating system for vacation rentals)Connect with him on LinkedIn  If you got value from this conversation:Subscribe to the channelLeave a comment with your biggest insight or question about AI in vacation rentalsShare it with someone in your network who manages properties or builds tools for themAnd don’t forget to subscribe to the Everything AI in Travel newsletter for weekly deep dives on AI, travel tech, and creator-driven distribution.

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• Education Series: Your guest has arrived. Now what?

  In Episode 6 of the “9 Free AI Tools to Attract High-Value Visitors” series, we review one of the most practical tools in the entire framework: the Self-Guided Tour Creator AI — built to help you create real, walkable, time-logical itineraries your visitors can use on the ground once they’re already in your destination.This tool sits in the “content” phase of the framework, but unlike inspirational blog articles, this is utility content: self-guided walking tours that improve the visitor experience, reduce friction, and help your destination deliver more value while people are there.In this walkthrough you’ll see how the AI:Starts with a destination prompt (example: Cuenca, Ecuador) and a defined target market (example: German visitors aged 25–50, culture + nature + local life)Lets you choose between a pure walking route or a route that includes short transportBuilds a realistic route with space/time logic: stop sequence, walking times, visit durations, and total tour lengthWrites engaging descriptions for each stop (and lets you refine tone, style, and format as you go)Generates a title + short platform-ready tour description you can paste into a brochure, app, website, or tour platformOptionally creates a quiz to add interactivity and engagementFinds Creative Commons licensed images for each stop (with source links)Translates the whole tour into simple, friendly German (or any language), and can even add practical info at the top of each stop: address, time to visit, next stop, and walking timeBy the end you’ll have a complete self-guided tour you can publish as: a web page a PDF handout a tour-platform listing a destination app experience content your staff can reuse in visitor support Access the 9 free AI tools here: santiagoR.com/freeAITools Want help implementing this for your destination, hotel, or tourism business?I also offer 1:1 coaching and staff training so you can apply these tools faster, with better outputs, and with a real content system behind them.If this episode helps you, like, subscribe, and share it with someone who works in tourism and wants better visitors and better visitor experiences.

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• What if AI didn’t keep us on screens… but actually got us together in real life more often?

  In this episode of the Everything AI in Travel podcast (now sitting in the top 3 travel-technology podcasts on Apple Podcasts), Tony sits down with Healy Cypher, co-founder & CEO of BoomPop, a company that just raised $25M to make planning in-person events, offsites and group travel radically easier with AI.We dig into Healy’s wild founder journey — from growing up in Saudi Arabia, to selling his first startup to eBay just seven months after joining, to rolling out those touchscreen kiosks in McDonald’s, Wendy’s and more (including the legendary “temptation cookie” upsell)… and why all of that led him to build BoomPop.Then we zoom out to the big shift: post-pandemic hybrid work, half-empty offices, and $1.7T in “freed” office spend that companies are quietly redirecting into in-person experiences, offsites, sales kickoffs and client events. Healy explains why group travel & meetings are the last undigitised corner of travel, and why AI is finally the unlock.You’ll hear how BoomPop uses AI to:Turn a simple prompt (“Offsite within 2 hours of SF in Q1, X budget, Y vibe”) into venue options, dates, full itineraries and a live event websiteMatch corporate events with hotel “need dates” so everyone wins on price and occupancyLearn a “taste graph” for organisers and companies to recommend better venues and experiences over timeHandle all the messy coordination: negotiations, blocks, RSVPs, guest messaging, packing lists, dinner changes and more— plus how a 35-person human planning team plugs in when you need a real expert, not just an agent.We also talk about the future of event agencies and travel advisors in an AI world, the incumbents like Cvent and the old-school RFP process, and what a new competitive landscape looks like when AI-native platforms start hitting escape velocity.If you’ve ever:Burned months of an EA’s time on a single annual offsiteRun a remote or distributed team that lives for its one big IRL gatheringWorked in hotels, DMOs, or meetings & incentives and wondered “why is this still done by fax and spreadsheets?”…this conversation will be painfully familiar and seriously hopeful. Listen now to learn how AI, group travel and in-person experiences collide — and why this is one of the ripest opportunities in travel tech. GuestHealy Cypher – Co-founder & CEO, BoomPopBoomPop: AI-powered platform for offsites, retreats & corporate eventsPodcast: Don’t Be a Jerk – conversations with high-performers who prove you can win in business without being an asshole. If your team has an offsite, retreat or client event coming upBefore you sacrifice six months of someone’s job to planning it… check out BoomPop and see what AI can take off your plate. If you enjoy this episode:Subscribe to the channelDrop a comment with your biggest takeawayShare it with someone who organises events and desperately needs their life backAnd don’t forget to subscribe to the Everything AI in Travel newsletter for weekly deep dives on AI, travel & creator commerce.

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• Education Series: The Blogger AI

  In this episode of the “9 Free AI Tools to Attract High-Value Visitors” series, we move from strategy into content creation and I walk you through the Travel Blogger AI—a free tool that turns your destination expertise into long-form, inspirational blog articles designed to attract your ideal travelers.You’ll see step-by-step how the tool:Fits into the 4-phase framework: Strategize → Intelligence → Content → OutreachTakes your target market (in the example: German travelers 25–50), your core destination (Cuenca, Ecuador) and your positioning… and turns it into a 7-day storytelling itinerary from Cuenca to QuitoBuilds an article outline, day-by-day descriptions, responsible & sustainable travel tips, and a “travel kindly” sectionHelps you refine the draft like a human colleague would—correcting details, adding your tone of voice, and matching your on-the-ground expertiseEven supports you with cover image concepts and Creative Commons photo suggestions to illustrate each day of the itineraryBy the end, you’ll know exactly how to use Travel Blogger AI to create deep, evergreen blog posts that:Position you as an expert in your destinationGive you long-form content you can later repurpose into social posts, newsletters and campaignsAlign perfectly with the high-value visitors you defined in your earlier strategy and market intelligence work. Access the 9 free AI tools here (including Travel Blogger AI): santiagoR.com/freeAITools Want help applying this in your DMO, hotel, tour company or local business?I also offer 1:1 coaching and staff training on how to use these tools in your specific context. Learn more via the link in the description.If this episode helps you, hit like, subscribe, and share it with someone in tourism who wants to attract better visitors, not just more visitors.

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• Agentic Commerce - AI reshaping the marketplace

  AI generated summary of McKinsey's latest report into agentic commerce for those who don't want to read the full 27 pages

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