Millman '05 launches NYC scavenger hunt company

Avi Millman ’05’s recently founded scavenger hunt company, Stray Boots, successfully launched its first hunt March 7, when 125 participants explored landmarks great and small in New York.

Stray Boots organizes scavenger hunts with destinations that include distinct landmarks, vibrant neighborhoods and unique cultural attractions, Millman said. During the first hunt, participants traveled to major New York sites like Rockefeller Center and the Metropolitan Museum of Art, as well as smaller-scale sites such as sections of neighborhoods and specific businesses.

The idea for Stray Boots was conceived when Millman took a trip with his family to Italy last summer, he said. On a train from Florence to Rome, Millman overheard a group of backpackers talking about how they kept running into each other, even in different cities, and an idea struck him.

“I thought to myself, ‘That sounds a lot like what would happen if they were on a scavenger hunt and looking for answers to the same clues,’ ” Millman explained. “Wouldn’t a scavenger hunt tour be a really fun way to see a new place, accomplishing what guidebooks do in a more engaging, interactive way?”

Millman, who grew up in New York, used his own money to launch Stray Boots. Currently, Stray Boots has only held one hunt in New York, but the company is planning to offer more hunts there in coming months, Millman said, adding that “the plan is to rapidly expand to other cities.”

Millman said he received “extremely positive” feedback after the first hunt, during which the participants had an interesting encounter in Washington Square Park.

“We didn’t tell people what the [location of the stray boots] was exactly; all we said was that we hid boots,” Millman said. “So [a hunter] saw this guy with really shiny boots and thought, ‘That must be what I’m supposed to get.’ So he stares at the boots for a while, deciding how he’s going to approach the guy. The guy, who obviously had no idea what was going on, did not like this so much, and started getting in the hunter’s face, who then tried to explain the misunderstanding … largely in vain.”

People can purchase tickets from the company to participate in the scavenger hunts, which are structured in a question-and-answer format and include some straightforward questions as well as some that are “more like riddles,” Millman said.

“We want to create a model here and then replicate it in other interesting places around the world, places where a scavenger hunt would be a fun way to see the sites, sounds and smells of the destination,” he added.

Hunters, organized into teams, earn points for each question they answer correctly. Point values vary according to the difficulty and venue of the different tasks, Millman explained. Bonus points are awarded for finding “stray boots” placed at various sites around the city.

As a perk, hunters receive discounts at certain locations they visit along the way, including museums, bars and restaurants. The team with the most points at the end of the hunt receives the grand prize, with smaller prizes going to those who finish in second and third place. Right now, Millman said, the top three teams receive American Express gift cards.

Millman, who majored in history and was involved with the Student Volunteers Council and the Whig-Cliosophic Society during his time as an undergraduate, said his experience at Princeton taught him independence.

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“When I arrived as a freshman, I was still largely reliant on someone telling me when to get … work done,” he explained. “Through the various independent projects I worked on … I learned not just how to manage my own time, but also how to motivate myself from within.”

These skills have helped Millman with his new endeavor, he added. “I believe the passion to create something meaningful and the ability to set and meet personal deadlines are both crucial attributes for any aspiring entrepreneur to possess,” he explained.