It took two seconds for Mindy Grossman to fall in love with the rambling old house and another nine years of gleeful collecting and fearless renovating to make it completely her own. What she's discovered along the way—about honoring the past, embracing the new, and staying true to your vision—could serve as a blueprint for living. Cathleen Medwick pays a visit. 
Take a tour of Mindy's exquisitely decorated home

I wonder what a high-flying corporate executive does here for fun. As I drive along the quaint dirt road, past gullies and bucolic hillsides, and up the long, winding drive that will eventually lead to Mindy Grossman's house in sleepy Millbrook, New York, I'm picturing a lofty residence presided over by a steely dynamo with zero tolerance for downtime. This woman was president and CEO at Polo Jeans Company and headed Nike's global apparel business before becoming CEO of IAC Retailing, a multibillion-dollar international corporation comprising brands as diverse as the Home Shopping Network (HSN), Shoebuy.com, and Garnet Hill. Not the sort you'd find at the garden club or a quilting bee.

But the woman who comes to the door at the end of that scenic driveway defies my expectations: warm smile, lively brown eyes, and an air of friendly curiosity; her Maltese, Tara, who guards these premises from an eight-inch-high vantage point, has more hauteur. Mindy Grossman is the sort of person who laughs easily, touches you casually in conversation, and says the word love so often you could take a bath in it. Which makes sense, because she actually is a woman in love. She first fell for her house nine years ago, after she'd touched down from one of her frequent business trips and was scouting for a country retreat with her husband, Neil. One look at the 200-year-old former parsonage—actually a constellation of three rickety buildings transported from upstate many years before, now surrounded by woods and meadows—and she was smitten. "That's my house," she announced to Neil. "We're buying it." They hadn't even walked inside.

That kind of swift decision-making is her trademark. "I've always been a risk taker; I've never believed in following the expected path," she says now. "When I left Ralph [Lauren] to go to Nike, people thought I was crazy. This fashion-obsessed woman from New York is going to show up in Oregon and be rejected by the sporty-guy culture! Well, that didn't happen. I loved the brand and understood that our mission was to inspire and innovate. And being a woman was empowering, not intimidating."

She stayed at Nike for a "breathtaking six years." What finally lured her away was a conversation with IAC chairman Barry Diller. "I got incredibly excited about the chance to marry content, community, and commerce," she says. By running IAC Retailing's shopping network (which includes online, television, and catalog brands), she would be able to make a personal connection, reaching into millions of homes, "anywhere and everywhere people wanted to shop, when they wanted to shop, and how they wanted to shop."

Her enthusiasm is contagious. It's all I can do not to put down my tape recorder and start shopping. Mindy nods her approval. "I spend all day thinking of shopping," she says, making no distinction whatsoever between the personal and the professional. "I love the thrill of finding that wonderful, perfect thing, the feeling of your heart racing because it's so right."

From the June 2008 issue of O, The Oprah Magazine

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