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It’s 11 p.m. at Precinct, in Somerville’s Union Square. In the bar area, college basketball is keeping fans enthralled as Duke and Boston College battle it out, but in the back room the crowd is there to hear the Singhs, the five-member band fronted by Art Technology Group cofounder and former CEO Miki Singh ‘85. It feels as if the gang’s all here. Singh flew into Boston from his 70-acre Caribbean estate one week ago to rehearse and perform with his Boston-based band members, and lots of old friends have come out to hear them.

The estate in question is called Gouverneur Bay, and Singh, who graduated with a degree in political science, purchased it after ATG’s $56 million IPO made him a rich man a decade ago. With money in hand, he rediscovered an early affinity for music that propelled his undergrad group Modern Man to victory at MIT’s Battle of the Bands in the early 1980s.Thus began his second career.

But first, his first career. The son of an Indian diplomat father and an Indonesian mother, herself the daughter of a diplomat, Mahendrajeet Singh was born in Stockholm and lived with his parents in Spain, Russia, Vietnam, Colombia, and Uganda. (He speaks Hindi, English, French, and Spanish.) After attending an Indian boarding school tucked deep in the Himalayas, he wanted to go to college in a city and found the vibe of Cambridge and Boston irresistible; he entered MIT in 1981. (He was Jeet Singh then; he reverted to his childhood nickname, Miki, when he started the Singhs.)

It was during his sophomore year that Singh founded Modern Man with bassist Joseph Chung and other friends from his fraternity, Alpha Delta Phi. Modern Man’s success had him briefly contemplating a music career: he took a year off from school to focus on performing at such local venues as T. T. the Bear’s and the Rathskeller. “Then reality sunk in,” he says. “I didn’t have a full scholarship. I had a lot of loans.”

Back to MIT he went.

As an undergrad, Singh worked for Tim O’Reilly, a publisher of computer books; not long after graduation he became a technical writer with voice-messaging company Boston Technology. “I could write, and I understood technology,” he says. “Those were my skills.” When a big project for Bell Atlantic came along, he found himself transitioning into the roles of project manager and then product manager. “This went on for four years,” says Singh. “That was my real education in marketing technology.” When the company moved from Boston to Wakefield and Singh tired of the suburbs (“I think the commute was the thing that basically killed it,” he says), he and Chung rekindled earlier conversations about starting a company. At first they envisioned a business that would have something to do with electronic music; Chung was then at MIT’s Media Lab, creating electronically enhanced instruments for the likes of Yo-Yo Ma. “We had just enough capital to pay the lawyers to incorporate us–I think it was $5,000 between the two of us,” says Singh.

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Credit: Laura Barisonzi

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