But Rowayton gave Freston a distinct taste for the good life. When he got a job as an umbrella boy at the Wee Burn Country Club at age 16, "I'd meet all these kids my age who didn't have to work and dressed better and drove cars their parents had bought them. It seemed outstanding to me."
His worldview was recalibrated in the summer of 1965 when, while working as a bartender at a leafy upstate resort at Lake George, in New York, he met a group of bohemian dropouts who read Jack Kerouac, smoked pot, and grooved to the going hit "Like a Rolling Stone."
"They had a free life; they'd make money and meet all the girls," he recalls. "It was a whole subculture for me, very alluring."
Back at his sleepy college of St. Michael's, in Vermont, Freston became the countercultural Johnny Appleseed to his more provincial friends, growing his hair long, subscribing to 'Rolling Stone,' and rolling the joints.
He was a natural entrepreneur, organizing for-profit keg parties featuring live bands. As manager of the school cafeteria, he assigned the dozen available jobs to himself and a couple of other friends, did all the work, and split the pay for 10 ghost employees. "He had operations and schemes going all the time," says his brother, Bill Freston. "That was always the deal. Undermining the system. 'Oh, they're such good boys' – meanwhile, a lot of drinking and smoking dope and partying. I don't think that's changed much."
After graduation, Freston applied to business school at New York University, primarily to avoid Vietnam. But he was turned on again - this time to Peter Drucker, the business management consultant, who taught a course in innovation and change, two concepts that seemed radical in the buttoned-down world of business. "I knew I wasn't a painter or a musician or anything, so if I wanted to be creative, I could gravitate toward that," Freston explains. "Innovation is taking two things that already exist and putting them together in a new way. I started getting excited. Maybe there's a place for a creative businessman."
In 1969, diploma in hand, Freston rewarded himself with a cross-country ramble, including a layover in the Virgin Islands, where he tended bar and tried LSD for the first time. ("Let's do that again," he told his female companion the next day.) But he returned to New York and went straight, getting a job at an advertising firm, Benton & Bowles. He chafed at the square life. "I got increasingly disillusioned with it and talked to friends on the outside who were living a free life, and I'd say, 'Man, I'm kind of trapped here.'"
So Freston left for Europe on a yearlong plane ticket, with no plans other than to see exotic sights and chase girls. "My parents were fucking appalled," he says.
Invariably, Freston found opportunity. In Greece he met "this gorgeous hippie chick" on the beach who was selling Indian fabrics to German tourists and making a killing. "I kept thinking, 'Maybe I could do this on a larger scale,'" says Freston.
He spent the next eight years building a clothing business from scratch, traveling around India and Afghanistan looking for fabrics and developing women's fashion designs for Western department stores. The company was called Hindu Kush, named for the Afghan mountain range - but also a strain of Oriental cannabis with which Freston was not unfamiliar. He opened a factory in Delhi with a local merchant he befriended (and still knows) and established a headquarters in Afghanistan, where he could live like a hippie king in Kabul, complete with his own butler and servant. He threw lavish parties for NGO workers, beatnik drifters, and soldiers of fortune he met during his travels. By the late Seventies, Freston says, Hindu Kush was a "multimillion-dollar operation. We were selling in Australia and Holland and the U.K. and all through the United States. We were making a lot of money. I couldn't believe it. It was a countercultural capitalist thing. Working like crazy. More than I would have in a regular job."
Then came a violent coup in Kabul in April 1978, which forced Freston to flee to Peshawar until the fighting blew over. It didn't, however. The new Communist regime, he says, began killing off local businessmen, so he shut down his Afghan operation, which was 30 percent of his business, and fled to India. "I hated to be shut out of a place I truly loved," he says.
Within a few months, the Carter administration enacted a new trade policy that put a cap on Indian clothing imports, which froze Freston's business midstream, leaving him with a big inventory and nobody to sell it to. As quickly as it had begun, Hindu Kush was kaput, leaving Freston $500,000 in debt.
"All of a sudden, I'm wiped out and it's 1979," he says. "I came back and said, 'I've got to find another way of life.'"