With $2M in new funding in the bank, Stray Boots is changing the ways tourists and residents alike discover cities

By Editor December 24, 2012

Stray Boots logoA Q&A with Stray Boots co-founder Avi Millman. The New York City-based company was founded in 2008 and closed a $2 million Series A funding round in late November. Investors include Milestone Venture Partners, Correlation Ventures and Great Oaks.

SUB: Please describe Stray Boots and your value proposition.             

Millman: We offer mobile-guided adventures that take you through the most interesting parts of the city, much like a cross between a tour and a scavenger hunt. Game mechanics make the experience of exploring the world and learning about it much more fun and engaging than alternatives, allowing you to play an active role in discovering things about your environment. Our hand-picked points of interest and contextual information about the area make the experiences extremely high-quality, so you know you’re always getting an amazing experience to share with friends and family.

SUB: Who are your target markets and users?

Millman: Our customers are both locals and tourists. In fact, we consider locals to be our target market, but our games are also great for tourists. We’re trying to give people a new, non-cheesy way to see and learn about the city, even if they’ve lived there their whole life. Locals aren’t going to use a guidebook in their hometown or jump onto a group tour all that often. We provide a fun, convenient, private way for them to explore the city on their own schedule and at their own pace, and in a way that doesn’t make them feel like a tourist. We find that the bulk of our customers are a pretty mainstream crowd: adults in their twenties, thirties, and forties. They’re doing Stray Boots with friends, significant others and folks from out of town. We also find a chunk of our customers are families with kids or teens whose parents love Stray Boots as a way to get their children off the couch and out and about.

SUB: Who do you consider to be your competition? What differentiates Stray Boots from the competition?

Millman: The most common comparison we get is generally to SCVNGR—their legacy check-in platform, not LevelUp, their payments platform. They’ve built an excellent software platform, but have gone with a user-generated content strategy.

We’ve decided to manage the customer experience from top to bottom thus far, which includes picking the places they visit and things they do, in addition to how the software works. To get folks taking a risk on spending their time, money, and social capital on trying real-world games, we decided we needed to guarantee a phenomenal experience from start to finish.

Recently, Google launched its FieldTrip concept on Android—an app called Wanderous is similar for iOS, which is also designed to give you an urban adventure that teaches you about the city. But the use case behind it is completely different. Rather than give you a pre-planned itinerary, it runs in the background on your phone to serendipitously give you info about the city as you explore. Thus it’s less a guide than a resource. We’re selling an activity, and our use-cases support that, whereas Field Trip is more of a tool.

SUB: When was the company founded and what were the first steps you took in establishing it?

Millman: We actually started the company in 2008 officially, but really got it off the ground in 2009 with our first beta on SMS. Earlier that year, we started putting out completely analog versions of scavenger hunts, by which I mean paper, and hosting events where we could get people doing them and giving us feedback on what about it they enjoyed. Then we shifted gears and started exploring what the best delivery mechanism would be. We liked SMS because it was simple and universal. Finding the exact right way to deliver an experience, though, wasn’t just about picking the technology, it was about how long an experience should be, where it should take people, what they should learn along the way, and tons of other things that related as much to the content as to the delivery mechanism or game mechanics. A lot of consumer testing and feedback helped us hone in on exactly what those things should be.

SUB: What was the inspiration behind the idea for Stray Boots? Was there an ‘aha’ moment, or was the idea more gradual in developing?

Millman: I was on a trip to Rome with my parents and my sister Noemi—our technical co-founder. I was using a guidebook and visiting all the major sites—the Pantheon, the Coliseum, the Trevi Fountain—checking all these great things off of my list. It made me feel like I was on a scavenger hunt. But at the same time, I started thinking about how passive the experience of using a guidebook or going on a tour is. All of the information, the entire process of exploring is one-directional. Having played games my whole life, I realized that it could be made so much more interactive and engaging by turning it into a game, one based around the idea of discovery and learning.

SUB: How did you come up with the name? What is the story behind it?

Millman: I’m a big Sherlock Holmes fan, and at the time I started the company I was re-reading one of his more famous books, The Hound of the Baskervilles. In it there’s a scene where a character’s boots go missing, or astray, mysteriously. I think Stray Boots, though, evokes a really strong sense of wandering, that liberating part of travel with just letting yourself drift around a new place, so it really works for our brand.

SUB: What have the most significant obstacles been so far to building the company?

Millman: Our biggest challenge is getting the word out. We feel very strongly about the quality of our product based on customer feedback and other data, but for a small company with limited resources it can be difficult to market a consumer brand like ours. Add to it that people aren’t actively searching for the sort of thing we offer—people generally don’t Google ‘urban adventure’ or ‘interactive tour’— we have to be creative about how we get ourselves in front of people. We still rely heavily on word of mouth, with a third of our monthly website sales coming from repeat and referral sources.

SUB: You recently raised $2 million in Series A funding. What are your plans for the funds?   

Millman: We’ll be using the funds to build out our technology platform and to grow geographically. Our tech roadmap includes a number of great features that will make the customer experience much richer and more social. Our plan is to launch Android early next year and to roughly double our North American footprint in the next 18 months.

SUB: Why was this a particularly good time to raise funding?

Millman: Our progress on SMS to date has allowed us to demonstrate real traction and a large market for our product. The funding will allow us to more rapidly make the transition from SMS to mobile apps and seize the market opportunity ahead of us. By moving more quickly on product and growth, we can become the leader in the space. When investors looked at the company, the reaction was generally “Wow. You guys have been able to accomplish this much with this little?” It seemed to naturally beg the question what we could do with real resources behind us.

SUB: How does the company generate revenue or plan to generate revenue?

Millman: We’ve been generating revenue from nearly day one. We ask customers to pay to play, and they do, knowing that they’re getting a high quality experience. That’s because they’re getting hours of entertainment from Stray Boots and the other things they could be doing with their time—going to a movie, doing a guided walking tour—are even more expensive, even at our $12 per tour price point. They’re not just paying for the technological service, but the work that goes into building great content and delivering a real-world experience that’s fun, interesting, and up to date. There are additional revenue streams we plan to tap into, such as local advertising from businesses along the tours and licensing our software platform, but right now we’re just focused on providing great experiences to our customers and building our base.

SUB: What are your goals for Stray Boots over the next year or so?

Millman: We’ve got a lot on our plate in the next twelve months. Included in it are launching our Android app, reaching a total of 20 U.S cities, expanding our library of tours in cities we’re already in, and executing great partnerships—we’ve already launched deals with Time Out Magazine and SeriousEats.com to do co-branded food and booze tours.

Stray Boots – www.strayboots.com