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.

The music part never happened for ATG (the “art” in the name emerged from the early association with music), but a lot of other things did. Drawing on contacts from the Media Lab, Singh and Chung got a job designing an interactive exhibit for a museum in New Jersey. Then came a request from Apple to build a Japanese promotion for QuickTime (then a brand-new multimedia add-on for the Mac). Next up: an 18-month job creating an imaging exhibit for Chicago’s Museum of Science and Industry. They hired a team. And before they knew it, Singh and Chung had built an interactive-media consultancy. “We thought we would be a product company, but we didn’t have a product,” says Singh. By 1995, though, they had a roster of heavyweight clients including MCI, Harvard Business School, and Sony. Then the Web hit, and those clients started asking for various Web services. To meet their needs, the company created the Web server Dynamo. From there, it began building electronic storefronts and moved into the then-nascent field of personalization, delivering Web pages tailored to individuals’ characteristics or preferences. “Then things really started taking off,” says Singh. By the time he and Chung took the company public in 1999, it employed more than two hundred people.

Most of this time, music remained secondary for Singh–a whisper in his ear rather than a roar. These were heady, busy days, and ATG was all-consuming. But in 1996, a friend took him to the House of Blues to see guitarist Peter Parcek play. Singh was blown away. “I realized I hadn’t picked up an instrument in years,” he recalls. “When I saw him I said, ‘I’ve been missing something.’” Self-taught until then, he began taking lessons from Parcek, and slowly music reëntered his life. In 2000, he purchased property in St. Barts, which he envisioned as a once-a-month getaway from Boston’s long winters. “I was planning on buying a little place–a shack,” says Singh. “But St. Barts is not much of a little-shack place.” When he discovered that the island held an annual music festival, he and Parcek decided to put together a band. And while they were down there, why not make a record? The group they assembled–which also included bassist Marc Hickox and drummer Steve Scully–was the heart of the band that’s still playing today. Soon they added a fifth member, Boston DJ and keyboardist Brother Cleve.

By that time the business world was beginning to wear on Singh. “It had been a long haul,” he says. Including the Boston Technology time, he had been in startup mode for about 16 years, through both boom and bust. ATG’s value had plummeted and the battered company, like so many others, was forced to rethink its business. “I was tired and stressed out,” Singh says. “I probably looked 10 years older eight years ago than I do right now.” With a new CEO at the helm of ATG and Gouverneur Bay waiting, he left the company in 2002 and began spending nearly all his time in the Caribbean. In 2003, the band–called Dragonfly until he learned how many others shared that name–released its first album. The Boston Globe called it “pretty darn special. … Rootsy, sad, elegiac, bitter, and rockin’.”

In 2008 the Singhs put out their third album, Supersaturated, the first to be released in the United States. Like the first two, it was recorded in the home studio onSingh’s property and combines pop, rock, and funk sounds. “We set up our own label pretty early,” says Singh. “We never were trying to get a record contract.” That decision proved prescient, as many record companies now struggle to support their artists. Singh plays guitar, performs lead vocals, and serves as the band’s primary songwriter.

Singh’s path from the boardroom to the stage has had its share of challenges, not least among them the perception that he’s just a high-tech guy who bought himself a band. “In the music business, there is a very strong feeling of ‘If you haven’t suffered in the music business, you can’t possibly be any good,’” he says. But time has chipped away at that reputation. The band has toured extensively in Europe and India; its members have an obvious and authentic camaraderie and are well-respected musicians in their own right. (Brother Cleve was in the Del Fuegos, and Parcek, a longtime fixture in the Boston music scene, has a new solo album coming out this year.) Supersaturated received play on 300 stations throughout the country. “And we’ve gotten better as a band,” says Singh. “We’re writing better, we’re producing better.”

But for Singh, the rewards of being a musician are found in the moment, foreign though that attitude is to the business world. “Americans in general, and especially business Americans, are not used to thinking about just being. It’s always, ‘What’s your plan?’” he says. “It’s not like I said, I’ll do this for five years and if we don’t sell x number of records I’m going to quit.”

At Precinct that night, things came down to the wire on the basketball court. The bar crowd watched with bated breath as Duke edged out BC. But in the darkened back room–far away from boards of directors and stock prices, product launches and office politics–the band played on.