He played football, won a scholarship to the University of Iowa at Iowa City, and became the first member of his family to earn a college degree. Almost immediately he secured a job (with business cards) at the Chicago-based Continental Can Company. A "progressive" company that promoted on merit regardless of race, Continental put Clayborne on a fast track to management. He rose through human resources positions at plants in Milwaukee and northern New Jersey, where he switched companies and signed up with Bristol-Myers.
He also took his résumé to a headhunter in New York, a city he had come to love. The move led him into the publishing business. At 26 years of age, Clayborne joined the human resources department of the New York Times Company, which owned several smaller newspapers, radio stations, and TV companies, in addition to the famous daily newspaper.
Clayborne characterizes his job as that of a corporate hit man, who flew into town like the grim reaper, often to fire a manager or publisher after negotiating a severance package.
He recalls sitting in a fine restaurant and ending the career of a man who had founded his own magazine. "This guy had about a gazillion dollars. And I looked at him and told him his services would no longer be needed, and he was devastated. I thought he was going to cry. He didn't care about the money, it hurt his pride."
But it didn't hurt Clayborne, who had begun to understand a life of privilege few black Americans of the 1970s enjoyed. "I couldn't feel sorry for them," he said of those he let go. "In the case of this particular guy, all he had to do all day was play golf. I told him, "Man, if somebody offered me a million bucks, I'd be out of here now.'"
One day, Clayborne recalls, his boss told him to rush out to La Guardia Airport and catch the company's corporate jet for a quick ride south. When Clayborne boarded the plane, the two pilots, both white, asked him if they could get him anything.
""Like what?' I said.
And they said, "Anything.'
I told them, "All right, let's stop in Philly and get a cheesesteak on the way, I'm hungry.'
And they said, "OK.'
I said, "No, no, guys, I'm kidding.' But it was the first time I realized how these people really lived."
Clayborne was not all business. In the fall of 1977 he traveled to the Bahamas to vacation. When he walked into a small, family-owned perfume shop, he met Bernadette Bostwick, an 18-year-old Bahamian. The next day he returned, took her to lunch, and asked her to marry him. She said yes. Clayborne returned to the island three weeks later to meet her family but found himself unable to rent a car to make the 20-mile drive from his hotel in the tourist area to her home.
"So he rented a golf cart," she says. "I was pleased and embarrassed. He drove miles in this golf cart; he was determined. When Keith is determined, there's no stopping him."
For about three years the couple lived in lavish style on the lower east side of Manhattan before buying a house on Long Island. By the time he was 31 years old, he earned more than $100,000 a year. "But I was bored," he recalls. "So one day I did something really stupid: I quit."
Clayborne decided he could manage a small business, work for himself, and make a lot of money. "I'd read some books about it, you know, and I thought that's all it took. So I told my boss, and he said, "No you don't, Keith, you don't want to do this.' And I said, "Yes, I do.' And I did."
Then the roller coaster started, recalls a now amused Bernadette. "I said, "Whatever, honey, I'll be right there,' but I didn't know I'd have to give up my Mercedes-Benz and teatime with the girls."
The couple took their savings and plowed it into small businesses on Long Island: a Laundromat, a dry-cleaning operation, some rental properties. They spent about three hard years there, then sold the businesses and moved to the Bahamas. They bought a house on the beach and ran a series of ventures, including a windsurfing operation near a hotel -- Clayborne loves to windsurf -- and later a "shopper," a little island publication for tourists and locals. Each week he had to fly to Miami to have the publication printed, because the cost on the island was prohibitive. Eventually he grew bored again.