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Q&A with Shie Gabbai, Co-Founder & CEO of Roam Around

Can you tell us about your career journey? What inspired you to start Roam Around?
Before Roam Around, I worked at Google for 6 years helping manage the Hotwire account and then working as a Product Specialist at Waze. I really enjoyed my time at Google but towards the end I was yearning for the startup hustle so I decided to join Strike, a Bitcoin payments startup. There I founded the Support org and helped scale our team to 50 agents within my first three months. Two years later, the crypto industry imploded. I was laid off and was looking for my next project. I didn’t start Roam Around initially; it was a project I discovered on Twitter, created by someone from the crypto space. As a frequent traveler, I was drawn to the idea of leveraging AI to streamline trip planning. I made some major changes to the usability and secured some partnerships, and shortly thereafter we went viral. We spent the last 9 months working incredibly hard to turn a viral toy into a thriving business solving real-world problems. I share more about our journey in this interview.

What sets Roam Around apart from other AI-based travel planning companies?
In short, focus and scale.

I think many startups fall into the trap of trying to do everything at once, and as a result, they don’t do any one thing particularly well. We’ve chosen to go deep on a single problem rather than going wide on many. We’re laser focused on making the process of planning a trip as easy as sending a text message. This intentionality can be felt throughout each feature of the site. As an example, instead of navigating through complex menus and filters, our users can simply describe their travel preferences in their natural language. This user-friendly approach wasn’t the simplest or most cost-effective path for us, but it’s one that deeply resonates with our users, enhancing their experience.

We also benefit from our first movers’ advantage. As a result of being the first GenAI travel planner, we’ve generated tens of millions itineraries, interactions and data points and used this data to fine-tune an AI model. Whereas most startups may be using GPT4, we are using a model tailored specifically for travel planning – think of it as GPT4-RoamAround. This model isn’t just about technology; it’s built on insights into what makes a travel itinerary compelling and effective.

Being first to market also allowed us to form partnerships with some of the biggest players in the game such as FLYR, Kayak, Viator and others.

The combination of our proprietary tech and these strong partnerships shapes the foundation of our success. However, it’s our focus and dedication that allows us to compete with both new startups and the incumbents.

What do you think makes the travel industry well-suited for AI?
Travel is a trillion-dollar industry stuck in the past. Most other industries – be it finance, healthcare, telecoms – have been utilizing AI for years, however COVID delayed travel’s AI moment. We believe that time has finally come.

What makes travel uniquely suited for AI is its inherent complexity and fragmentation. It spans a vast range of services – from planning and booking to customer service and logistics. This complexity is amplified by the dynamic factors influencing travel, such as real-time changes in weather, economics, politics, and cultural events. And finally, the global nature of travel requires sophisticated algorithms for language translation and cultural nuances, an impossible task for most humans.

Despite its nascency, AI is already incredibly adept at synthesizing large, complex data sets in easily consumable ways.

AI’s impact in travel isn’t just theoretical; hotels and airlines are already leveraging AI to refine pricing strategies. Looking ahead to 2024, we anticipate a significant shift toward consumer-focused AI applications that provide personalization at scale.

Gone are the days of static vacation packages and mass produced email content. We welcome the future of bespoke recommendations that make the world feel a little bit more small, a little bit more you.

Roam Around began working directly with travelers. What made you move into the B2B space with FLYR?
The move into B2B was demand driven. Specifically, we saw that travel brands, and airlines in particular, were struggling with a sense of being commoditized by OTAs. There was a time when flying was a significant part of the travel experience. Airlines had a close bond with their customers, and this connection fostered strong brand loyalty. However, with the proliferation of aggregators and their focus on price comparison, this relationship weakened. Airlines’ unique identities became diluted, and their roles in the travel experience were reduced to being just another option among many.

Our goal is to rekindle that lost sense of connection and place airlines back in the center of the user’s end-to-end journey. Airlines have an abundance of information about their passengers – destinations, travel companions, the purpose of their trips. We see this as an untapped resource. By leveraging AI, airlines can offer personalized, tailored experiences, making each journey distinctive and memorable.

Our approach involves leveraging AI-driven tools to empower airlines to deliver comprehensive travel experiences that extend beyond the flight itself. We’re transforming the role of airlines from mere transporters to architects of unforgettable travel experiences.

This strategy isn’t just about the destination; it’s about enriching the entire journey, every step of the way.

What’s next for Roam Around? What are some key goals and priorities for 2024?
It sounds a bit sci fi-esque but our goal in 2024 is to complete a one-click vacation. At that point we’ll have a good understanding of how you travel (your preferences, budget, interests) and the itinerary we present you should be about 80% perfect. From there, you’ll make some slight changes, and then with the swipe of a finger, everything from flights, hotels, restaurants and activities will be booked for you.

We think this is going to be a massive, pie-expanding moment for the Travel industry. Just as people now take Ubers far more than they ever took taxis, we expect people will travel far more often when booking the perfect vacation is as simple as a click of a button.

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