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The Man Who's Turning Cities Into Trivia Games We interview the CEO of a mobile gaming startup that helps urbanites get to know their cities better.

By Brian Patrick Eha

Opinions expressed by Entrepreneur contributors are their own.

Avi Millman, the co-founder and CEO of mobile gaming startup Stray Boots, has made it his mission to help urbanites get to know their cities better. Stray Boots' text message-based games are part treasure hunt, part guided tour, and designed to appeal to locals as well as tourists.

Prior to founding Stray Boots, the 29-year-old Millman -- who graduated from Princeton in 2005 with a history degree -- handled distribution and logistics for a retail apparel company and managed sales for a startup beverage company. We caught up with him by email to learn how Stray Boots just might be the future of urban adventure. What follows is an edited version of our exchange.

Entrepreneur: How did you come up with the idea for Stray Boots?
Millman: I had the idea for Stray Boots while on vacation with my parents and sister in Rome. I was visiting different sites -- the Pantheon, the Colosseum, the Vatican, the Trevi Fountain -- and it felt like I was on a scavenger hunt. With my history background, I've always loved travel, and more generally exploring cities, but it dawned on me during that trip how passive the experience of following a tour guide or reading a guidebook really is. I realized you could make the entire experience of exploring the world so much more engaging by turning it into a game that you actively participate in.

Entrepreneur: What makes Stray Boots unique and appealing to users?
We take you to amazing spots you'd expect to visit on a phenomenal guided tour. Many people spend years living in a city and learning very little about it. We give you a way to do it that fits to your schedule and interests. We do all of this without charging you a fortune or requiring you to hang out with anyone other than the friends and family you'd be spending time with anyway.

Related: 3 Hot Tech Startups Burning Up L.A.'s 'Silicon Beach'

Entrepreneur: In January 2012 you entered the Entrepreneurs Roundtable Accelerator in New York. How did the program help Stray Boots develop?
We had bootstrapped the company with some success up until [this past winter], but realized that to take things to the next level, we needed an injection of capital and that as first-time entrepreneurs, mentorship would also be extremely valuable. Despite our initial hesitancy in trading equity for those benefits, the accelerator and its mentors followed through completely. ERA has made introductions [for us] to dozens of investors. They also helped us hone our message to customers and potential business development partners.

Entrepreneur: What are some challenges you've dealt with, and how did you overcome them?
At one point we had an SMS (short message service) provider who quickly went from providing extremely reliable service to regular outages during which we found ourselves on Saturday afternoons with dozens of customers having their games all completely crash at once. We provided great, understanding customer service, proactively giving refunds to those affected customers and [sending] personalized emails and calls. We then promptly switched providers to the one we're still using today.

Entrepreneur: How much capital have you raised, and from what sources?
To date, we've raised $400,000. I initially self-funded the company with my parents with $40,000. We are close to closing our Series A round, the details of which I can't yet share. It will be in the $1.5 million range.

Related: The Entrepreneur Who Captured the Record-Breaking Space Jump

Entrepreneur: What is your path to profitability?
In 2011, we generated about $170,000 in revenue, all from game sales. This year we're on pace to finish the year with $300,000 to 400,000 in revenue, also all from game sales. This has been with just an SMS-based product. We're releasing our first iPhone app in just a few weeks, which will take the gameplay experience to a whole new level, as well as making it extremely social. We expect to be profitable by 2014, but may forgo short-term profitability to pursue additional geographic expansion.

Entrepreneur: What places attract you as possible new venues for Stray Boots?
Some that come to mind are Germany and Austria, Australia and New Zealand, China and India and, most memorably, Dominica and Uganda. Ultimately we want Stray Boots to be all over the globe, available in at least six continents and dozens of languages. But we're staying focused for now on expansion within the U.S. Our plan is to expand to 30 cities in the next 18 months from 14 currently. We expect to expand further within Europe within two to three years.

Brian Patrick Eha is a freelance journalist and former assistant editor at He is writing a book about the global phenomenon of Bitcoin for Portfolio, an imprint of Penguin Random House. It will be published in 2015.

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