He then held a series of venture capital-type jobs, including a disastrous venture of his own called the Legacy Fund, which he started with Timothy R. Furey ’80 and on which he lost $250,000. He says Legacy has since become a well-known case study about how venture capitalists can be misled by company executives.

After a little over a decade of assorted business jobs and other ventures, Ledecky was laid off in 1994 from his business development job at Steelcase, an office furniture dealership, and decided to start a business of his own.

Ledecky says, after Steelcase, he wanted to combine the economies of scale represented by companies like Steelcase and Staples with Legacy’s philosophy of supporting small businesses. From this concept, U.S. Office Products was born.

With U.S. Office Products, Ledecky proposed to buy up a number of smaller office supply firms to leverage bulk purchasing for profit. He contacted 100 firms. Ninety-five said no, he recalls.

With five companies and $100 million in sales, Ledecky tried to secure financial backers to take the company public with a so-called “poof” Initial Public Offering, or IPO. But again, he faced rejection: the first 40 firms said no. When the 41st firm, Mabon Securities, finally agreed to back the company, Ledecky went to Fidelity Investments for financing.

There, like so many other times in his career, a Harvard connection advanced him the next step. At Fidelity, Ledecky says he met with William A. Danoff ’82, whose sister he had dated and whose father he had worked with. And because of this personal connection, Danoff advanced him $3 million.

Across the street from Fidelity, at Putnam Investments, he found another Harvard connection—and investor. There he met with star fullback James L. Callinan ’82, whose exploits he had written about in his Athletics Department job at Harvard. Recalling statistics from the football player’s undergraduate career, Ledecky convinced Callinan to match Danoff’s investment.

When Mabon went under within a month, Ledecky convinced Robert E. Grady ’79, also a Crimson editor and whom he knew from The Crimson sports cube, to convince his firm, Robertson Stevens, to back U.S. Office Products.

The rest is history—and history well-chronicled in the pages of business journals. His success led the Washington Post to nickname him “merger master,” and even Ledecky confirms he had the Midas’ touch.

“I am between 1995 and 1998 literally the golden boy of creative finance on Wall Street,” he says. “Everything’s turning to gold—it’s an amazing run.”

As U.S. Office Products began to decline by 1998, Ledecky split up the company and removed himself from an active role, moving onto other business pursuits with handsome profits.

He started a number of rollup companies, including U.S.A. Floral Products and Consolidated Capital. In the process, he drew some criticism—Forbes Magazine said “Ledecky spun an attractive yarn,” building companies on “glib gab”—from those who perceived Ledecky as making a quick fortune and then cutting and running.

Ledecky’s business practices have certainly been influential: he says they’ve inspired about five case studies—some successes, some failures—and he now regularly travels around the country to talk to business school students.

“I’ve had a track record not unlike that of a venture capitalist,” he says. “I’ve been a big risk taker, and I continue to take major risks.”

Mark D. Director ’80, a friend who helped Ledecky run U.S. Office Products, says the rollup was one of Ledecky’s most creative innovations.