While he doesn’t regret the experience, by the early 1980s he had had enough. He entered drug counseling and then became a counselor himself, finding he had a knack for talking others through their addictions.

Reverse Social Climbing
Around this time, he visited Nantucket for the first time with friends and instantly fell in love with the island’s unpretentious vibe. “A few blocks from here, you have some of the richest people in the world, and they compete to show who has the most bashed-up Jeep,” he laughs. “It’s reverse social climbing.” For years he and his wife, Alison, rented homes, putting their linens and plates into storage on the island every season. More than a decade ago, they bought some undeveloped land outside of ’Sconset and sold it within a year for twice what they paid, allowing them to buy their current cottage. Over the past few years, they have moved the whole house back from the street and expanded it to open up a smaller guest cottage in the back.

  William and Babe Paley

The home’s simple style matches Bill’s own attitudes better than the high fashion he grew up with. “There are elements of happiness that have nothing to do with money, but that have to do with being part of a community, of family or of friends,” he says. With his children, he vowed to be a very different kind of father than his own; he sits down to dinner with them and makes career choices based on spending time together. If anything, he says, he’s made the mistake of being their friend too much. But he is clearly proud of the results—his older son is a partner at Bostonbased video game company Lantana Games, and his younger son is currently studying at American University.

Now that the children have moved out of the house, La Palina has allowed Bill to sail the world, traveling from city to city as an evangelist for his new brand. “It’s sort of a step of faith at a time when I should maybe be retiring and getting a sailboat,” he says. At the same time, he sees the company as a natural extension of his outlook on life—cigars are something to be savored. “I believe in living in the present, and I think cigars lend themselves to that. It’s a time when you can let go and relax—you turn to the person next to you and talk about what you’re smoking, and slip into personal anecdotes and connections.”

Ironically, as he talks about his own forays into spreading the word about La Palina through social media, it’s as if he has connected full circle to the days when his father was introducing the brand through the new medium of radio. “I’m kind of in the media business right now,” he laughs. “I’m doing a song and dance about cigars.” If he has finally joined the family business, he’s done so on his own terms. Shortly before Bill’s father died in 1990, Bill had lunch with him at a time when he was losing both his eyesight and his mental faculties. “He said, ‘You should meet my son Bill, you’d be a really good influence on him.’ I was about to say, ‘You know, I am your son Bill.’ But then I said, ‘You know what, I’ll take it.’”