Your next guest is asking ChatGPT where to stay

AI has officially joined the trip-planning group chat, and independent hotels are finding themselves at an inflection point—part headwind, part open road. Jason Cincotta, co-founder of Kismet—the AI-first booking rail for hotels—is helping properties navigate this shift, empowering them to be found, understood and chosen by AI-driven travel platforms.

In this conversation, he shares what every independent hotelier needs to know about optimizing visibility, owning their data and focusing their efforts where it matters most in the age of intelligent discovery. 

—Interview by Jennifer Glatt, edited by Bianca Prieto

How did you get into tech, and what keeps you there?

I played with ChatGPT-3.5 when it launched in research preview in late 2022 and immediately thought: people are going to book travel using this someday. It took me another year to act on it. I'd planned to return to McKinsey & Company after business school and work in their hospitality practice, but I decided the chance to be part of a technology shift like this was a once-every-20-years opportunity. Too big to miss. 

I founded Kismet in late 2023. A background in hotel ownership and asset management, plus a facility with data and websites, meant I could assemble a team and help build the product to solve the problem that had kept me busy for years: how do we reach the guests who will love our hotels most?

As AI tools like ChatGPT and Gemini influence how travelers find hotels, what should independent operators do now to stay discoverable?

Think of AI tools as a new distribution channel. Discovery is different because it’s not just top-of-funnel. Guests can now find your hotel, get detailed information on why it’s perfect for their trip, and (soon) book without opening another tab.

Independent operators have exactly the kinds of properties guests love. The content you already have from social media and press coverage to photos and videos tells a story that inspires a guest to pick you. The challenge is making this story visible to AI. It requires organizing information and choosing formats that AI assistants can find and cite. You might have heard of “structured data.” The technical parts are important, and we’ve spent years getting good at helping AI “read” and “operate” hotel websites, but companies like ours are only as helpful as your content is great.

With AI relying on context and structured data rather than traditional search, how should independent hotels rethink their digital presence to get recommended?

Your website still needs to inspire guests to pick you. That hasn't changed. What's new is that you also need a layer that AI can read. Here's the tension: the more engaging your site is for humans, the harder it often is for AI. Beautiful design, dynamic pricing widgets and interactive booking flows make AI ignore you and read from an OTA.

The trick is having something for both audiences: a beautiful "brochure" for guests, and a structured "catalog" for their AI—room types, rates, seasonal programming, neighborhood context—so an assistant can match the right traveler to you.

As AI plays a bigger role in the booking journey, how might the mix between OTA and direct bookings change for independent hotels?

This is a pivotal moment. The good news: we're seeing that guests who use generative AI to find hotels can be up to twice as likely to book when they touch a direct channel.

OTAs start with an advantage—they provide standardized inventory at scale. Make no mistake: AI defaults to OTAs. But since AI assistants can evaluate far more information than a traveler scrolling through listings, there’s a real opportunity to serve that information yourself and have AI show your direct booking channel to guests. I expect hotels with websites that are hard for AI to read will lose direct share, while hotels that make themselves AI-ready can win more direct business, especially from travelers looking for the right fit, not just the lowest price.

Anything else you'd like to share?

I’m optimistic: there's never been a better opportunity to reach guests directly. The funnel is getting flat. A guest can go from considering a destination to seeing a curated list of five hotels—with pricing, images and personalized descriptions—in minutes. I get it. No one (including me) got into hospitality because they love technology. But if you have a great property, you've done the hard part.

Embracing this channel early is the best opportunity independents have had in decades to lower distribution costs and connect with the guests who will love them most. We named the company Kismet because we think in the AI distribution world, the best guest for your hotel is fated to find you.

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Mint Pillow is curated and written by Jennifer Glatt and edited by Bianca Prieto.