Michael Gulmann and Otto - transforming the business travel experience

MVL Managing Director Mike Fridgen sat down with Michael Gulmann, Founder and CEO of Otto, to discuss the future of business travel. Otto, an AI-powered travel assistant, combines personalization, automation, and AI to simplify the experience for business travelers. 

Mike: Otto is an exciting venture, and I'd love to hear more about what made this moment the right time for you to take a big swing at reimagining the travel experience.

Michael: We're at a point where advancements in transformer technology and large language models (LLMs) suddenly make it possible to bring a more human experience back to travel. I often talk about the evolution of travel from the 1970s and 1980s, when you had a trusted travel agent who knew you, understood your preferences, and could guide you effortlessly through the booking process.

When Expedia and Travelocity came along, they did an incredible thing. They essentially turned the screen that only travel agents had access to around, giving consumers the power to be their own travel agents. But that meant travelers had to curate everything themselves. Now, we can bring back that personal touch with AI, but with even more intelligence and automation than ever before.

Mike: Otto is essentially bringing back the personalized experience of the past with modern technology. Can you describe exactly how Otto works and what makes it stand out from what's on the market today?

‍Michael: Otto is an AI-powered assistant but functions more like a highly skilled travel agent or executive assistant. It gets to know your habits, your preferences, and your travel history. Whether you're booking a red-eye to London for a Tuesday meeting or you want to stay within walking distance of your company's office in Chicago, Otto knows exactly where to book you. It's about more than just filling in forms and matching preferences to generic recommendations.

Behind the scenes, Otto uses a multi-agent architecture. We've built specialists—AI agents, if you will—who are experts in booking air travel and hotels and even handling in-trip issues. For instance, Otto knows I prefer red-eye flights into London so I can get to the hotel, shower, and be ready for my meetings that same day. It remembers these preferences and takes care of everything for me—completely seamless, just like working with a top-notch travel agent.

Mike: It sounds like Otto isn't just an incremental improvement but a fundamental reimagining of how travel booking works.

‍Michael: Exactly. Most systems today, even the more advanced ones, still rely on a linear process. You book a flight, a hotel, a car rental, and so on. If something goes wrong, like a flight delay or cancellation, it's on you to fix it. Otto changes that. It proactively monitors and solves these issues without you having to lift a finger.

For example, if your connecting flight is delayed, Otto will know and rebook you, just like the best travel agent or executive assistant would. It's the difference between being transactional—booking flights and hotels—and offering a truly personalized service that follows you throughout your trip.

Mike: If Otto successfully achieves its most audacious goals, how will it change how we experience business travel?

‍Michael: Ideally, Otto will make business travel completely effortless. No one wants to deal with the hassle of calling service agents when something goes wrong, like a delayed flight or a messed-up hotel booking. With Otto, those days are over. It becomes your personal assistant, handling all the in-trip complexities for you.

Imagine never having to explain your travel problem from scratch. Otto will already know what's going on and will fix it without any need for interaction. It's not just about booking; it's about having a seamless experience from start to finish. Whether it's rebooking you on a new flight or ensuring your favorite hotel is always available, Otto will handle it.

Mike: Congratulations on recently closing a $6M seed round! You've assembled a dream team of investors and industry leaders. Can you tell us a bit more about who's involved and how they're helping to shape Otto's future?

‍Michael: Raising $6 million is fantastic, and we're putting that to great use. But what truly sets Otto apart is not just the funding—it's the combination of the investors backing us and the strategic partnerships we've established. On the board and leading the Madrona investment is Steve Singh, the founding CEO of Concur and the driving force behind Madrona's portfolio of business travel investments, including Spotnana, Direct Travel, and TROOP, and the architect of the perfect trip vision.

Being part of an ecosystem with key players means we can handle the entire transaction process—flights, hotels, and even handling changes or cancellations seamlessly. These partnerships allow us to provide the end-to-end service that most travel startups never achieve. Many companies in the last decade have focused on niche aspects, like discovery or price comparisons, but Otto is taking a much more comprehensive approach, evolving into a personal executive assistant for business travelers, not just another booking tool. 

Mike: MVL has been working closely with you since the early stages of Otto. What has your experience been like collaborating with MVL?

‍Michael: It's been a fantastic partnership. One of the things that stood out to me right away was how MVL takes on the operational burden that often bogs down early-stage founders. Whether it's company formation, finding a law firm for the seed round, or hiring our first team members, MVL has been right there with us.

On the execution side, they've provided tremendous support in building the tech. We still need to build out our in-house development team, but thanks to MVL, folks like Jay Bartot and Jason Flateboe are leading the initial design and development. It's been a huge relief knowing we're surrounded by experts who have been through this before.

Mike: You've held some incredible roles in the travel industry, and I imagine you've taken some pretty epic trips yourself. Is there anything you can share on that front?

‍Michael: For me, epic trips aren't about luxury or cost—they're about experiencing something new. My family and I went to Croatia a few years back, long before it became a hotspot. We rented a small house in an agrotourism area on the island of Brac, completely off the beaten path. We hiked through valleys, followed paths used by donkeys, and just enjoyed the serenity of it all. That trip was probably less expensive than a stay at a Holiday Inn, but it was unforgettable.

Another memorable one was Morocco. We drove around the country, stayed in the Sahara desert, and even stopped by a local school, where the kids taught us how to write our names in Arabic. These are the kinds of experiences that stick with you. For me, travel is about culture, new perspectives, and learning—and Otto will help people experience that more easily by taking the stress out of travel planning.

Mike:Before we wrap up, what kind of team are you looking to build at Otto? What type of people will thrive in your company's culture?

‍Michael:I've always valued curiosity above all else. I want people who are intellectually curious and passionate about learning and problem-solving. Obviously, skills matter—if we're hiring a lead engineer, they need to know how to code—but beyond that, it's about people who are driven to ask questions and improve things.

At Otto, we're building a collaborative and challenging culture. I don't want a hierarchy where the most senior person always makes the final call. The best ideas should rise to the top, regardless of where they come from. So, if someone enjoys challenging the status quo, working in a fast-paced environment, and delivering exceptional customer experiences, they'll do well here.

If you're interested in shaping the future of business travel with AI, check out our open positions for a Fullstack Software Engineer and Senior Software Engineer at Otto.

Founder Spotlight is a series dedicated to bringing you insights into the founder journey, lessons learned from startup leaders, and a behind-the-scenes look at some of the most compelling tech companies in our community.