The moment came for Avi Millman in Rome, on a vacation with his parents and sister. A guidebook had led them to the Trevi Fountain and the Pantheon and all the other major Roman hot spots. Then the young Princeton University student suddenly noticed two things: He was on a scavenger hunt, and the roadmap to it was exceedingly passive.

Millman is a man of many ideas for businesses; one of those serial entrepreneur types, but with the advantage of knowing that if he doesn’t truly love his idea, he’s not going to do well in business. “I’m not going to have a bagel shop if I don’t have any passion for bagels,” he says.

So rather than just start new businesses every time he comes up with something, Millman bounces ideas off his family and friends. Most are met with “meh.” But this one, this thing about making tourism within a city more interactive, more engaging, more of an actual scavenger hunt for information and historical facts about landmarks, raised eyebrows. This was something people told him sounded like a lot of fun. The only question was, how does a history major with no technology knowledge turn a love for games and tourism into a 21st century business?

Millman will discuss the founding of Stray Boots (, his New York-based tourism company, as a panelist at the New Jersey Technology Council Venture Conference on Friday, March 22, from 9 a.m. to 4 p.m. at the Hyatt Regency in New Brunswick. The conference features more than 300 exhibitors and the lunchtime panel, which also includes moderator David Sorin, managing partner at SorinRand LLP; David Drahms, principal at Osage Partners; John Frankel, a partner at FF Venture Capital; Paul Gollash, CEO of Voxy; and Stray Boots’ co-founder and head of operations, Scott Knackmuhs. Cost: $400. Visit

Millman is the product of risk-averse parents, a father who is an attorney and a mother who is a librarian. But on his mother’s side, his grandfather and great-uncles owned a clothing brand and a store, which makes Millman (who graduated from Princeton in 2005) wonder whether the entrepreneurial spirit is in the blood. His sister, Noemi, is a mix of the pragmatic and the entrepreneurial, enough at least to become the technical thrust of Stray Boots.

But before Millman recruited his sister to build the technology platform that delivers interactive tourism games through cell phones, he and Knackmuhs (a 2007 history and economics graduate at Penn) took the low-tech approach — paper.

It was 2009 and Millman had built his professional experience in distribution as the supply chain director at clothing maker Steve and Barry’s and in sales at beverage supplier Q Tonic. His idea for his company was fresh, but he knew nothing about technology, nor how to actually make a business out of a leisure activity.

“We put paper scavenger hunts in people’s hands,” he says. “We promoted the hunts on EventBrite and other websites. We would all meet at a bar at the end, and people told us what they liked and what they didn’t.”

Make no mistake, Stray Boots wasn’t supposed to be a paper-based company for long. In all that paper, Millman and Knackmuhs were cobbling information that would be used to build a technology platform. And just because neither was technologically adept, Millman says, there was no reason to wait. “You can think of starting a business,” he says. “But you have to get going.”

The technology evolved through two main avenues. One was the information Stray Boots was gathering about who takes localized tours like the company offers and the other was Noemi. On the information-gathering front, feedback was coming from the bar talks and from reviews on websites such as Trip­ And what Stray Boots was learning was that Millman’s original expectations for who would buy tours were not correct.

Millman went into Stray Boots thinking that people would buy tours for places they’d never been, or were at least far away. In reality, most customers are from the city for which they buy tours. Also, those first tours were led at scheduled times, and people wanted to be able to take them whenever it best fit their individual schedules.

This is where the need to build the cell phone delivery platform came in, and where Millman recruited his sister to take care of it. Noemi, who graduated from Princeton in 2002 with a bachelor’s in political science and computer science, had been freelancing as a website developer and doing other computer jobs through her company, Triopter.

Millman had no money to hire her to develop a tech platform that would deliver numerous individualized touring games for numerous American cities. His main capital was his belief in what he was doing, and with it he convinced Noemi to build a text message-based program.

Things will get a little fancier than text messaging, but probably not much, Millman says. The games are for people, not just geeks. “There’s always this tension when you’re building a tech company to build the biggest, coolest thing that only one percent of people know how to use,” he says. “Tech grows fast, and you run the risk of alienating people if you move too fast. Augmented reality would be cool, but our customers are not just people in their 20s who are male and read ‘Tech Crunch.’ A lot of our customers are in their 30s and 40s who are tired of going to bars and want to explore their towns.”

Each Stray Boots tour is for an area within a city. Instead of buying a New York City tour, for example, you might buy a Wall Street tour. You receive challenges for different landmarks, like a trivia game except more interactive. The clues might say “Walk up Broadway. The man on your $10 bill is buried in a graveyard there. What year was he killed in a duel, and by whom?” And you would proceed to the grave and text back the answers to the questions. Then you would get a new set of clues.

This is about as complicated as it gets, and that’s the way Millman and crew want it. Fun. Simple. Engaging. It’s only complicated because of the technology involved, but he has Noemi to worry about that now — she is the technology director for Stray Boots.

Millman considers himself fortunate, not just because he grew up in the same house as a tech person, but because the time and place were right for him to build a company out of an idea based on fun. Though Millman has been a fan of puzzles and games since he can remember, his father’s pragmatic advice about business had Millman thinking about business schools as he rounded out his time at Princeton.

But the fact that he had an idea and the ability to survive while building it over two years — he was in his early 20s, single, and able to live at home without health insurance and no real income — is why he counts himself among the lucky ones.

“Lots of businesses fail because a lot of it depends on your ability to weather the storm,” he says. “You need to be in a good personal position to take the risk.” His parents are a lot less concerned now.

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