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Even the purple and gold bucket hat – more of a beanie, really, the kind customarily donned by ������ý���� freshmen of the day – did little to stifle the confidence of Norm Brodsky ’64. The lanky 18-year-old from East Rockaway, Long Island, climbed to his seat in the bleachers of Alumni Gym and sat with his classmates to hear an address from President Franklin F. Moore ’27. It was a warm, late summer morning in 1960, their first day as ������ý���� students.

“He said, ‘look to the left of you, and look to the right of you. One of you isn’t going to make it here,’ ” recalled Brodsky, an impish grin spreading across his face at the memory. “So I got up and sat next to the dumbest looking guy I could find and said, ‘It’s you.’ ”

History holds no account of how the classmate, his identity long lost to the ages, fared in his studies, but for Brodsky, Moore’s words were a challenge: “If somebody else could do something, I guessed I could do it as well, if not better, than them. It spurred me on to do a number of things I wouldn’t otherwise do.”

That boldness has endured for Brodsky, a self-described “serial entrepreneur” who, on little more than a lark, started a document storage company from a floundering trucking and messenger service. Today, CitiStorage houses more than 4.3 million boxes in its 17-million-square-foot facility in the trendy Williamsburg section of Brooklyn.

There is a popular question often posed to entrepreneurs: How many things can you do well? Ask Brodsky, and he claims just one true skill.

“I can see the future!” he quips, but there is a ring of truth to it. Brodsky, who also graduated from Brooklyn Law School, worked as an attorney before starting his own law firm, but found himself alone among his partners hustling to drum up new business.

“I said, ‘If I’m going to sell, why do it for law?’ So I left and even then, more than 30 years ago, I could tell that the country was becoming a service-oriented country, so I decided to go into a service business.”

The result, three years later, was Perfect Courier. It was 1979, and parcel delivery companies were exploding. “This business was unbelievable. I started from zero and built it up to $120 million in seven years,” explained Brodsky of his rapid ascent. “And then I went from $120 million to zero in seven months.”

While there were several external factors, Brodsky says the wise entrepreneur looks within for accountability. His aggressiveness and zeal for growth had left Perfect Courier vulnerable.

“You have to understand how you contributed to a failure,” he said. He wouldn’t make the same mistake twice.

 “My dad used to tell me, ‘there’s a million dollars underneath your shoe.’ I would look, and say, ‘where?’ ” Brodsky recalled. “But what he meant was there was opportunity everywhere.”

With Perfect Courier in bankruptcy proceedings, one of Brodsky’s employees received a call from a costumer asking if the company stored documents. “We were looking for new opportunities,” he recalled of the request to store 27 transfile boxes. “And we always teach our staff never to say no without talking to a supervisor.” Brodsky called a number of moving and storage companies, asking about rates and scheduling, and soon became giddy with the possibilities. He could do the job quicker and for significantly less money than any of those established outfits.

“I called her back and said, “Hi, this is Norm Brodsky from the box storage division of Perfect Courier,” he recalled. He picked up the boxes the next day and kept them in his office for two months. Like that, CitiStorage was born. “Those 27 transfiles are now more than 4 million boxes,” he said.

Purchasing the property that CitiStorage’s flagship warehouse facility now occupies in Williamsburg would seem to be proof of Brodsky’s prescience. Directly across the East River from midtown Manhattan, at the water’s very edge, the tract represents some of the most desirable real estate in America, the end of a 10-minute walk that begins at the Bedford Avenue subway station and proceeds past hip coffee houses, chic shops and even a swanky boutique hotel in a former dye house. Want in? A two-bedroom apartment in the neighborhood might fetch $4,500 a month.

None of it bears any resemblance to the neighborhood Norm and Elaine Brodsky scoped in 1990.

“It was terrible. There were shootings all the time. Nobody was living here,” he said of the land, which had lain fallow for close to 50 years. “New York City used to park their garbage trucks at the end of the street.”

Even the forward-thinking Brodsky needed a good deal of arm-twisting. “It was great space, but it was ridiculous, so dangerous,” he said. Eventually, at the insistence of his real estate agent-friend, he relented. His business was growing, and he needed to expand. This was not a speculative real estate deal, his insists, but rather, a purchase of necessity.

“I bought the land because I had a use for it,” he said. The Brodskys began constructing their colossal warehouse, notable for its height as well as sizable footprint, and their business grew up with the district. Notable of the building is that it also contains the Brodskys’ home, a stylish, 5,000-square-foot, open-concept apartment with views as grand as any in the borough. Across the river, the Empire State Building looms, a silent witness to the astonishing transformation of Williamsburg. The Brodskys have since donated part of their land to New York City to use as waterfront park space.

The burgeoning CitiStorage earned Brodsky a large share of visibility within the business community, and in 1995, he was asked by Inc. magazine to author an advice column for entrepreneurs. The immediately popular “Street Smarts” led to a recurring space in the magazine, and eventually, a book collaboration between Brodsky and Inc. editor Bo Burlingham, The Knack: How Street-Smart Entrepreneurs Learn to Handle Whatever Comes Up.

Brodsky sold the CitiStorage business in December 2007 for $110 million, though he and Elaine maintain control of the property, where they also continue to live. The two, who ran the company for the next two years on a contracted basis, still maintain an active, visible and friendly presence among the staff inside the warehouse. Always on the lookout for new and profitable ventures, Brodsky remains an active backer of a number of projects from Manhattan to North Dakota. But he also enjoys sharing his well-earned wisdom with up-and-coming businesspeople and even hosts a scotch-tasting event for promising entrepreneurs twice a year in his home.

“God gives you these great lessons,” Brodsky said, a nod to the many experiences – good and bad – that have shaped his own career. “What are you going to do with them all unless you share them?”

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Norm Brodsky ’64 was honored with the Distinguished Alumnus Award on June 8 at Reunions 2013. A version of this profile appeared in the spring 2013 issue of RIDER magazine.