Rutter was neither drifter nor artist--just a guy enjoying his own transitory immaturity. While still at college he had started driving a cab, and for much of the 1970s he trolled the streets of Boston picking up businesspeople, drunks, academics, psychotics, and various combinations thereof. In 1981 he followed a cabbie friend to a limousine company--"for the air conditioning and the cleaner clientele," he says. A month later he was managing the 15-car operation, and nine months after that he was back on the street after clashing repeatedly with the company's owner. "She was very heavy-handed and difficult to deal with," says Rutter. "When I looked around I saw that style of management was typical of limousine companies. That's when I decided to start my own."
With $35,000 from his mother and some pamphlets from the Small Business Administration, Rutter launched Commonwealth in 1982 as a high-end limousine company. Despite the premium-service mantra, a slacker spirit prevailed. "All I ever wanted was maybe five cars and a nice place for my friends and me to work," says Rutter. Even that was unattainable at first; he found himself back in a cab part-time just to keep himself and the business alive. He owned one car and was still driving the cab in June 1982 when the "big break" happened.
The story of the big break has a Pavlovian effect on Rutter. Each time he mentions it, off come the glasses and up well the tears. What at first seems like excessive sentiment is in fact abject gratitude. A lot of entrepreneurs will tell you about the account that changed everything, but most are manifest-destiny types, confident that if Client A hadn't made their fortunes Client B would have come along shortly. Rutter, by contrast, seems convinced he'd still be in the bush leagues if John Brady hadn't come into his life.
In 1982, Brady was the new editor of Boston magazine and a recent transplant to the city. His wife, an editor for Cincinnati magazine, had refused to pull up stakes, and so Brady spent the spring and summer of that year trying to persuade her to move. One day when she was visiting, Brady hired Rutter, whose brochure had turned up at his office, to take the couple on a city tour. Rutter ferried them all over, from Faneuil Hall in Boston to the Old North Bridge in Concord. "He made a very strong impression on me," recalls Brady, who is now president of his own publishing consultancy in Newburyport, Massachusetts. "He had a charm to him, and a personal touch."
Seven months later, Rutter was in cab-driving mode when dispatch ordered him to 34 Warren Avenue. (He is a street address savant; he also recalls 20-year-old dates with freakish specificity.) Serendipitously, the fare was Brady; the two reconnected and Brady was once more charmed. They met again by chance when Rutter was picking up attendees from a party at a nightclub. In August 1983, Boston magazine released its annual Best of Boston issue with a brand-new category: Best Limo Driver. "There was no runner-up," says Brady. "And so a legend was born."
The Best of Boston imprimatur was wind beneath Rutter's wings. Business tripled instantly; he bought a third car, a fourth, a fifth. He vowed, Scarlett O'Hara-like, never to drive a taxi again. "He had seen me...working hard...struggling...and he just did a really nice thing for me," says Rutter, momentarily overcome. "That wasn't luck. That was fate. That was meant to happen like that. That was absolutely meant to happen like that."
Reinventing the Wheel
By industry standards, Commonwealth in the late 1980s through mid-'90s was a ringing success. Eighty percent of U.S. limousine companies have fewer than three cars and chiefly ply the wedding and prom trade. By 1990 Commonwealth had 20 cars, $1.5 million in revenue, and a client base that included some top Boston hotels. With a couple hundred thousand in take-home pay, Rutter had exceeded his modest dreams--modestly.
So he played golf. Five or six times a week. "I had a 3 handicap--at one point a 2.5 handicap," says Rutter. "I didn't have to work very hard, and I didn't."
Then in 1998 Carey International made its uninspiring offer: $1.4 million. And from the crucible of that failed acquisition, growth guy was born. Anger was the catalyst, but Rutter also responded to a more pragmatic concern. Simply put, he realized that his nice little company wasn't worth very much. "It was a wake-up call," he says. "Unless I did more to build value in this business, I was going to be 80 before I could afford to retire. I rededicated myself to the business. I was going to see what I could do."
Unable to interest banks or investors in his plans for expansion, Rutter was forced to work off retained earnings and a $100,000 line of credit. He determined to reinvest every nickel he made. Anxious to multiply those nickels as quickly as possible, he naturally targeted sales, which had previously been limited to his own desultory efforts. His first recruit was an expensive but very effective rep from--where else?--Carey. Over the next five years Commonwealth hired eight salespeople, including three in 2002 when the travel business was at its nadir.
Rutter steered his new, high-powered sales team toward financial companies whose road shows put suits in seats for days or weeks of driving. Steadily Commonwealth assembled a top-tier client base. After breaching New York in 2004, Rutter snagged some of the town's choicest hotels, whose exalted guests have gone on to retain his services for themselves. Most recently, Rod Stewart hired Commonwealth for his 2007 tour after sampling the company's service at the St. Regis. "Entertainment is becoming another great vertical for us," Rutter says.
