Sidney D. Wolk

Class of 1999

  • Founder, Chairman & CEO The Cross Country Group

One of the greatest things about this country is the fact that people who become successful remember where they came from and tend to give back many times over.

The son of Russian immigrants, Sidney Wolk was raised in Boston. His father, a plumber, had little education and could not read. At the age of 10, Wolk sold newspapers on the corner each day before school. On his first day of work, a customer gave him a dime for the five-cent paper and then drove off down the street. Wolk ran for more than a block to catch up to his customer so that he could give the man his change. "He told me it was a tip," says Wolk, "but I wouldn't accept it. I couldn't see taking extra money for just doing my job."

Honesty and integrity were early lessons learned from his parents. "We never owned a home or a car," he explains. "My brother and I never went to summer camp. Our lives were tough, but my parents never allowed us to lose faith in God or this country. We were told over and over that the opportunities in America were there for everyone, if you were willing to work for it."

Wolk was accepted into the selective Boston Latin School. While there, he served as a class officer and, in his sophomore year, played on the varsity baseball team. He worked throughout high school at a number of jobs including stock boy, busboy, waiter, and ice cream truck driver. At Boston Latin School, Wolk was exposed to talented teachers and intelligent, determined classmates. He began to see what the world could offer someone who was willing to work hard. Upon graduation, he enrolled at Boston University. With the help of a partial scholarship, loans, and work, Wolk was able to pay the $550 annual tuition. He continued to live at home, taking public transportation to school and to his jobs each day; during college, he always had at least two jobs at a time.

Armed with a degree in business administration, Wolk worked as a traveling salesman for a New England furniture company. He discovered that his ease with people made him a good salesman. Before long, he felt ready to start his own business. His parents co-signed a $1,500 loan and put up their furniture as collateral to start a mattress furniture retail store. "My mother told the banker, '˜Our furniture is like firewood, but you can have it if you want it.' We all laughed, and they gave me the loan." In the beginning, Wolk often didn't know how he would meet payroll, but eventually he made the store a success. Eventually he sold it and moved on to his next enterprise.

Joining Nationwide Insurance as an agent, Wolk became its top salesperson nationally within a few years. Building on that experience, he founded his own insurance premium finance company. The sale of that business ultimately led to the creation of The Cross Country Group LLC, which became a leading provider of private-label direct marketing and customer service programs in North America.

When he first started in business, Wolk says he couldn't define success. He realizes that success means enjoying what you do and sharing that success with those less fortunate. "One of the great things about this country is the fact that people who become successful remember where they came from, and tend to give back many times over."

After his mother and an aunt lost their sight later in life, Wolk became active with the Greater Boston Aid to the Blind, where he has served on the board of governors. He has also made an effort to hire and train disabled people in his company. Wolk feels strongly about helping troubled youth find a way to be successful. The Youth Automotive Training Center does that, and Wolk is an avid supporter. "Be the best at whatever it is you want to do, and be ready and willing to change as necessary," Wolk often tells young people. "Have faith that the best is yet to come."

Wolk recalls his mother when discussing his Horatio Alger Award. "She was right," he says. "America is the land of golden opportunity. To me, this award is the ultimate recognition of a success story in America and shows what people can do in this country if they put their mind to it. On a personal level, it is the culmination of all the work and good fortune that went into the success of our organization. I am especially proud of all the good the award does in giving back to worthwhile students to further their education, which is one of the keys to success. That's what makes this award one that will always mean the most to me."