[ The Money Side of Lifeā„¢ ]

An Entrepreneur's Game

By Jeremy Da Rosa on January 21st, 2013 •

Entrepreneurship can seem simple: take an idea from a twinkle in your eye to a product on the street, pass 'GO,' and collect your $200 (though hopefully there's more revenue than that). Unfortunately, the rules are a little more complicated and there is no instruction manual.

Some claim to have one (How to Start a Business in 10 Days, Two Weeks Notice, 50 First Businesses, The Businessperson's Notebook), but chances are not every spur and hang-up will be addressed in a 200-page book emblazoned with the toothy grin of a self-made person-of-the-week. Having one of these "guidebooks" isn't a prerequisite for success.

Enter Avi Millman, co-founder and CEO of Stray Boots, a mobile gaming company based in New York City. Since 2009, Stray Boots has provided phone-based city tours with SMS starting points, instructions, and clues as players work their way through their personal Amazing Race-style tour.


With his entrepreneurial sap still rising, Avi explored the ranks of employment after graduating from Princeton with a degree in History. "I didn't really know what industry I wanted to be in… but I knew I was young and I was aware that I didn't know, so I tried to get different types of experiences. First it was opera¬tions, then it was sales, and what I ended up learning was that what I really loved was growing businesses from a very early phase," he said.

Watching his two successive employers, who themselves had taken an idea they were passionate about and turned it into a marketable product, Avi realized he could only get so excited about someone else's ideas. "I didn't want to work for somebody else doing what they wanted to do. I wanted control of my own destiny."

His destiny, as it happened, came to him in a flash on a family trip to Rome. "It sort of dawned on me how passive the experience of sightseeing is. When you're on a tour or reading through a guidebook, it's so one directional… I had an idea: one of my passions has always been travel, and another passion has always been gaming." If that travel or tour experience was turned into a game, with instructions, a point system, and goals, it would be more dynamic and interactive, he figured.


As is often the case in know-as-you-go scenarios, Avi had plied different avenues until he found one that proved more than just another dead end. "I had a lot of bad ideas for companies," he confessed, "and I had run those ideas past a lot of people whom I respect. They pretty much told me [they were] lousy ideas. I remember the reception was very different when I told people about the idea for Stray Boots. And I decided to take the plunge."

While not a required move, Avi opted to maintain his day job while developing Stray Boots after clocking out of his nine-to-five. Naming and registering the company, for example, were things he could do while avoiding the headache of not having regular personal income. "It's certainly worth starting that way, formulating the business while you're working full-time so you can make a living."


After a few months of balancing a full-time job and putting together the busi¬ness plan for Stray Boots, Avi felt he was doing a disservice to his employer by splitting his time between his business and the company. "It was really challenging," he admitted. "But you don't want to be in a position where you're shortchanging your employer to get your own business off the ground… you're either going to be shortchanging your business or you're going to be shortchanging your employer and neither is particularly fair."

Moving from an after-hours entrepreneur to a fully formed business with a product on the street often poses the biggest risk to the potential proprietor--both financially and personally. "We bootstrapped the company to start… we self-funded the business… and we didn't take a salary. Every hour I worked without pay was essentially an hour invested. And that holds true for my cofounder as well," Avi said of partner Scott Knackmuhs. It meant the business was taking a financial loss as they sought to grow the company while simultaneously refining the product on the fly.


It was a strenuous process, but Avi affirms that the choice to take the product to the streets, literally, was the best way to develop it. By immediately selling the tour, he was able to find out what people liked and what clearly wasn't going to work. "What better way to learn than by refining a product after putting something on the market early," he said. "What do people want to see? What are the game dynamics that they really like? We really did try to understand the consumer almost out of a necessity to sustain our¬selves as business owners." Stray Boots adjusted the product to market demands, but didn't waste time getting something out there despite knowing the product wasn't perfect. They went all in, naysayers be damned, and expected the big payout.

Innovating with an impromptu strategy also proved to be a great boon. Stray Boots now operates across the United States and features four tours in two cities in the United Kingdom (see strayboots.com for a complete list of cities). While not completely by-the-book (seeing as there isn't a definitive one), Avi contends that, regardless of the approach or the idea, the end goal of an entrepreneur is to present consumers with goods or services which will meet their expectations. "You know if you can provide a consistently high-quality experience using your product that you're really onto something, and that if you can maintain that quality as you scale the business, you'll ultimately be successful."

Sources: strayboots.com; ukthegame.com