Who would ever think that half a turkey and Swiss cheese sandwich would lead to a promising career? Probably not Gary C. Hill, who, as a high school student in 1981, unknowingly shared half of his sandwich with his future boss and business partner, Tom Gardner. “Little did I know that it would be the best career decision I ever made,” says Hill. More than 20 years later, Gardner-co-founder of the Motley Fool, a financial information service-repaid Hill by offering him the position of chief financial officer of the company.
The son of a statistician for the Census Bureau, it seemed that Hill, 35, was naturally suited to mathematics. After graduating from Brown University in Providence, Rhode Island, in 1987 with a degree in mathematical economics, Hill landed a position as an analyst at Citicorp in New York. Shortly thereafter, he relocated to the company’s Los Angeles headquarters to become a relationship manager in its airlines and aerospace group. While there, the Washington, D.C., native used his move west as an opportunity to earn an MBA at Stanford.
After B-school, Hill’s plans were veering toward a career in the airline industry. But he decided to go into investment banking in 1993, and headed back east to New York City. He accepted an associate position at Morgan Stanley in its merger, acquisition and restructuring group, advising companies in a variety of industries.
During his last months at Morgan Stanley, Hill received numerous calls from Gardner, who was eager to incorporate his old friend’s expertise into the up-and-coming Web company that he and his brother, David, were expanding. “I hired Gary because we had a lack of knowledge on the financial side of the business,” says Gardner. “His expertise helped us establish a vision and maintain order as a company.”
Based in Alexandria, Virginia, the Motley Fool started out as a newsletter that was later placed online at America Online. Motley Fool used the revenue from subscriptions to expand the business. Hill’s patient and methodical execution “brings oversight to every dollar we make,” says Gardner.
For Hill, a job at the Fool presented an opportunity to return to his hometown area. But leaving a position at a financial giant for an upstart company required him to take a sizable pay cut. Hill, who gained an undisclosed amount of the company’s equity, was more concerned about the long-term opportunities of joining Fool, however, than the temporary reduction in take-home pay. “I knew I would be satisfied with the trade-off because I’d be gaining happiness,” he says.
In early 1996, Hill resigned from Morgan Stanley and joined Fool, which is privately owned. The company is dedicated to delivering simplified financial information with a sense of humor via the Internet, a syndicated radio program, books and newspapers. Hill’s moniker was “Slash” during his first year at Fool. “I was involved in human resources, finance, legal, business development and anything else that wasn’t editorial content.” In 1996, when Hill started, the Fool had only 15 employees and an estimated $2 million