Gary Burton and Scott Benson Bob Kramer Studio

He's an example of that quintessentially turn-of-the-millennium breed of businessmen: an Internet entrepreneur. At age 43—"going on 23," he says—he's led a handful of companies from start-up to take-off, each time intending afterward to rest on his laurels and stock options. Instead, he's been unable to resist the call to steer one enterprise after another to success. But through it all, there's been one other inspiration nagging at Scott Benson: music.

"Music is as much a part of my life as ever," says Benson. "Music affects me every day."

Through Berklee College of Music, in part, Benson is finding new ways to make music a part of his life. Joining the Board of Trustees last spring, Benson has placed his firsthand knowledge of the Internet revolution at the disposal of a technology-hungry college. He has endowed a scholarship to support Berklee students who resemble his young, pre-computers self. Last fall, he sponsored faculty member Al Kooper's benefit concert, taking it in himself from front row center. And his "retirement" project, should he ever get around to retiring, is a record label— Risky Music, echoing his mother's assessment of a music career—dedicated to helping a small number of bands succeed.

"It's my last really big dream," says Benson. "I'm in it for the music this time."

Though not exactly for the first time. Growing up in Chicago, Benson had plenty of music in the house, with his father playing saxophone and accordion, and his mother wearing out Frank Sinatra records. Learning the wrong lessons from Sinatra's delayed entrances and behind-the-beat phrasing, Benson says, "I have a bad sense of rhythm. I can't come in on the beat."

Benson picked up the guitar when he was 16, and soon began performing in the manner of his folk-rock heroes, Simon and Garfunkel. But it was disillusionment with college that drove him to take a stab at the musician's life.

After one semester at school, he dropped out and headed to Los Angeles. But he didn't fit into the musical culture there in 1976. After three months, he decided to try another great music town—Boston. He found it much more to his liking. "In Boston, the more successful [performers] were, the harder they worked," he says. "I liked that work ethic."

He soon found a vehicle other than music for that work ethic. He joined up with a computer engineer and tried to peddle the idea of a computerized recording studio. But in those pre-digital days, he says, "there was no interest." They tried to transform their product into the first general-purpose computer that sold for under $10,000, but that, too, went nowhere. "That company was my one failure," he says.

One and only. Benson founded Microsystems International, a networking company that was acquired by a larger firm, the European operations of which he took over and revitalized. "It was quite a successful gig," he says. Then he spun off Microsystems Software, which developed products to make personal computers accessible for the disabled, as well as e-mail-enabled scheduling software.

Then, in 1994, Benson retired for the first time, selling his interest in the company to his partner. "I wanted to get back into music," he says. To keep his hand in business, he served on boards of directors for software start-ups, but continually got drawn into management. One such firm he managed was Software.com, which has since become what he calls "the dominant player" in Internet messaging. When, in 1997, Software.com "got too big for me," he says, Benson "decided again to retire, again to get back into music." But again, it was not to be. He joined the board of another Internet company, Valent Software, as chair and chief executive. Though he senses another retirement in the offing, for now, he says, "I'm having a ball."

Even as he's proved unable to extricate himself from the business world, Benson has managed to develop a new link to music through Berklee. Through a mutual friend, Benson met Berklee trustee and Newbury Comics founder Michael Dreese, who brought him to the Encore Gala and other events.

To Dreese, who ultimately recruited him to the Berklee Board of Trustees, Benson represents a natural Berklee patron. Like Dreese himself, Benson is a successful businessman whose cultural tastes are rooted in rock.

"There's a new generation coming out of high-tech, in part, who have interests other than the Museum of Fine Arts," says Dreese. In a sense, the timing could hardly be better, he says. "Berklee is coming of age at a time when people who grew up with that music"— the rock, pop, and jazz made by electric guitars and music synthesizers—"are in a [financial] position to give support."

"Scott Benson is the kind of person we love to connect with," says Executive Vice President Gary Burton. "More than an appreciation for music, he has a passion for being involved in it himself. And he finds a part of himself reflected in Berklee."

More and more, in fact. The endowed scholarship he established for songwriters is intended, Benson says, "to help young versions of me."

But Benson has put his Internet connections to work for the college as well. Through a former company, Benson has arranged for 100,000 lifetime e-mail accounts for Berklee graduates to be administered through the college, a service that will enhance Berklee's value to alumni for years to come.

That e-mail gift is just a small example of what Benson has to offer Berklee College of Music as an advisor and benefactor, says Dreese. "One of the biggest things is, he's a cutting-edge futurist. He doesn't just think up things, he can execute in a way the marketplace understands." For Berklee, that's becoming more important as the music-technology revolution evolves from production to distribution, with Internet technologies such as MP3.

"The delivery mechanisms and marketing mechanisms are changing so rapidly," says Dreese. "He's in a position to know what that really means."

For Benson's part, he's just thrilled to be a part of the Berklee scene. "From my first month in Boston I've been looking at Berklee," he says. "Little did I know I'd get involved."