Turning Fun Into a Business – Avi Millman and Stray Boots

by / ⠀Entrepreneur Interviews Startup Advice / June 7, 2012

A few years ago, Avi Millman was on a family trip in Rome, his face buried in a guidebook, shuttling from one historical site to another, thinking to himself, “Wow, this could be so much more interactive.” That glimmer of an idea would eventually grow to become Stray Boots, which Avi describes as “your own private ‘Amazing Race’ on your cell phone.” Participants receive clues, learn facts and earn points as they complete the challenge of an urban adventure.

Each “game” is a 2-3 hour experience, but can be spread out over the course of a day in whatever way feels comfortable for the players. Recommended start and end times are provided, based on when certain locations are open, but aside from that, participants are freed from the constraints of a conventional walking tour. If they want to stop along the way for a bite to eat, or to explore a certain site more thoroughly, that flexibility is built into the experience.

Millman credits his undergrad history degree with fueling his passion for travel and urban exploration. After graduating from Princeton in 2005, he worked for the COO of the popular clothing chain, Steve & Barry’s during a period of rapid growth for that company, and then for the Brooklyn-based beverage start-up, Q Tonic (now called Q Mixers). Both positions gave him loads of hands on experience in sales and development, that would later prove extremely valuable when he formed his own company.

In 2009, Avi teamed up with former Steve & Barry’s supply chain analyst Scott Knackmuhs to develop and launch the first Stray Boots tours in New York City. In 2010, after refining their concept, building a number of deals and raising some angel funding, they brought in experienced web developer Noemi Millman (Avi’s sister) as CTO, to fully build out the web based software.

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Stray Boots is currently operating in 15 American cities and a growing number of locations in the UK. The company is preparing to launch in Miami, and is looking forward to a dramatic increase in the number of participating cities this year. Typically, they will work with local partners to build out the games, but once they’re built, the games are fairly stable and can be managed from the main office in NYC.

Most recently, the company has developed some great partnerships with brands such as Time Out, to create a suite of co-branded nightlife games, and Serious Eats, to create a series of foodie tours. According to Millman, “For any consumer facing company, the biggest challenge is figuring out how to get customers in the most fundamental way.” Partnering with these more established brands is proving extraordinarily helpful in getting their product out in front of more people.

Surprisingly, in addition to out-of-town visitors, Stray Boots has found great traction with local residents, offering a great option for exploration that doesn’t have the same connotation as jumping on a tour bus. Although they have a significant number of 25-40-year-old users, the games have also developed quite an appeal for families who are trying to entertain their 8-18 year old kids – very different from the 20-something-year-old backpackers Millman had expected would be their ideal audience.

I asked Avi if he had any advice for would-be entrepreneurs.  When he first started out, he told everyone he knew that he was starting a company. He says making himself accountable to them in this way made the whole thing real. He’s pretty sure that it’s this social pressure to succeed that made him stick with it during the many times he could have given up along the way. “If you’re serious, you should tell people. It will really put your feet to the fire and make sure you jump in with everything.”

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For Avi, the most rewarding thing about Stray Boots has been the positive customer feedback. He explains, “It’s great to know you’re helping people have fun in a new way.” Seeing pictures and reading comments from enthusiastic customers, and receiving requests to bring the games to new cities has really helped him and his team to continue marketing their product with great confidence. “The way you know you’re onto something [is] people are just really happy to use it.”

Deborah Oster Pannell, a Smith College graduate, is a writer who specializes in the arts, media, holistic health, advocacy and events. As Director of Communications for the tech start-up eventwist, she also manages their blog. Some of her favorite work is featured on modernlifeblogs.com, lizkingevents.com, and her own blog, She Says Yes. Currently she is launching Project Mavens, a literary, editorial design collective, with partner & writer Lillian Ann Slugocki. 

About The Author

Matt Wilson

Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on Under30CEO.com, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.


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