What if the biggest problem in hotel booking isn’t finding a hotel — but finding one that actually works for you?

<p>In this episode of the Everything AI in Travel podcast, I speak with Vadym Klymov, founder and CEO of WinWin Travel, about using AI to solve one of travel’s surprisingly stubborn problems: personalization.<br>Vadym comes at the problem from firsthand experience. He spent 12 years in hospitality in Ukraine, growing from renting out his grandparents’ four-room summer house to operating his own 48-room guesthouse and working with a 98-room hotel. He was preparing to develop a 300-room property when the war changed everything and he relocated to the Netherlands.<br>That eventually led to WinWin Travel.<br>The premise is simple: Booking.com, Expedia and most hotel websites don&#39;t contain enough information to answer the questions that really matter to travellers with specific needs.<br>We dig into:<br>🐕 Why travellers with pets can end up calling dozens of hotels just to find somewhere that accepts two large dogs — and determine what it will actually cost<br>♿ Why accessible travel requires far more detail than an &quot;accessible&quot; checkbox — including bathroom door widths, bed heights, flooring and other specifics<br>👨‍👩‍👧 Why families, pet owners and travellers with disabilities are WinWin&#39;s first three niches — from 38 traveller niches the company has identified<br>🤖 How WinWin uses AI agents to contact hotels, ask questions, understand free-text responses and turn them into structured, searchable data<br>📊 Why the company has developed more than 15,000 potential questions for accommodation providers and thousands of corresponding filters<br>🔄 The surprisingly difficult problem of keeping all that information current — and why simply giving hotels another dashboard to update doesn&#39;t work<br>📧 Why AI-powered email conversations are currently outperforming both forms and AI voice calls for collecting information from busy hotel teams<br>🔌 How WinWin&#39;s MCP strategy could allow other entrepreneurs to build highly specialized travel products on top of its data<br>🏨 Why WinWin ultimately sees the bigger opportunity as B2B2C infrastructure, rather than simply becoming another niche OTA<br>🌍 How one LinkedIn post generated hundreds of partnership enquiries from people interested in building niche products using WinWin&#39;s MCP<br>🇦🇪 Why Dubai and the GCC have become a major focus for the company, particularly around accessible tourism<br>💰 And why Vadym is now actively looking for both niche distribution partners and investors as WinWin expands into the GCC.<br>One of the most interesting parts of the conversation is how AI changes the interface entirely.<br>Without AI, extreme personalization could mean confronting travellers with thousands of filters and checkboxes.<br>With AI, the traveller can simply say:<br>&quot;I&#39;m travelling to Dubai, I&#39;m a wheelchair user and these are the things I need...&quot;<br>The AI can translate that natural-language request into the hundreds or thousands of underlying data points required to find accommodation that genuinely fits.<br>That&#39;s a very different version of hotel search — and potentially a much more useful one.<br>#AI #TravelAI #TravelTech #Hospitality #AccessibleTravel #PetTravel #AIAgents #MCP #HotelTech #TravelStartups #Personalization</p>