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The Business of Being Oprah

She talked her way to the top of her own media empire and amassed a $1 billion fortune. Now she's asking, 'What's next?'

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Trust also goes a long way toward explaining her investment in Oxygen Media. When Oprah first met Geraldine Laybourne, the Oxygen co-founder explained that she wanted to create a women's cable network based on intent and service. "Intent and service--that is my motto," Oprah says. "I thought, my God, this is my idea exactly." In fact, Oprah had kicked around the idea of starting the Oprah Winfrey Network (OWN) on cable but had never found the time or the courage to develop it. Enamored of Laybourne's plan, Oprah contributed $20 million plus certain rights to The Oprah Winfrey Show library and received a 25% founder's stake. It seemed like a sweet deal at the time, but the two-year-old network has had trouble getting the right programming and buzz. Asked if she is happy with her Oxygen investment, Oprah pauses--one of the rare moments in six hours of interviews when she's at a loss for words. "Am I happy with it?" she says, bouncing the question back. "It is an investment."

The following morning Oprah calls to say that she woke up at 11:19 p.m., worrying about her answer. "I really don't define my happiness by my business decisions," she says. "Now if you ask me, 'Are you uneasy?' I'll tell you that I'm not uneasy about Oxygen itself." She is confident that the cable startup will survive. That's not the issue. The issue is that she deeply regrets handing over the rights to reruns of The Oprah Winfrey Show. "It's not just a commodity," she says. "It's my soul. It's who I am." She's not being rational here: Any knowledgeable banker would say that old Oprah programs have little monetary value. But Oprah says she feels ethically obliged to have a team review every program--more than 2,000--and inform the guests who appeared on the old shows before reruns begin to pop up on the Oxygen channel beginning in September. "I would rather have put $100 million into Oxygen and kept my shows than put in $20 million and given them away," she says. "I feel I gave myself away too readily." After a pause, she adds, "Every time I talk to you, I feel like I'm in therapy."

Oprah never has been in therapy, and for the most part she seems like someone who would hardly need the help. When I first started researching this story last June, I went to see her inspirational "Live Your Best Life" road show. Oprah stood on stage and declared to 1,700 fans: "I believe I'm just getting started. The TV show is just the foundation.... If you're open to the possibilities, your life gets grander, bigger, bolder!"

But when I visited her in Chicago five days before Sept. 11, she seemed utterly different. She talked about being confused about her business. "Maybe I should be in therapy," she teased. She felt more restless than ever, particularly about her talk show. That very week she had done an hour on girls who don't eat and wished they were Britney Spears, and she thought to herself, "I don't know how I'm going to get through the year." She even said to FORTUNE, "I'm sick of people sittin' in chairs stating their problems. Then we roll the videotape ... then we have our experts on the topic. I truly don't know what to replace it with. As soon as I do, I'm pullin' those people from their chairs." She added, "I'm in the 'what's next?' phase of my career."

Then came Sept. 11, and Oprah got her groove back. Laura Bush's office called, asking if the First Lady could come on the show to talk about children and terrorism. Oprah followed the Laura Bush program with themes such as "Islam 101," "Is War the Only Answer?" and "What Really Matters Now?" During a conversation in January, she was singing a different tune: "What I'm saying to people--Are you living your best life? Are you living your life with passion?--no longer seems so airy-fairy, so cosmic, so out there." (Of course this does not mean Oprah abandoned her commercial side. Far from it. A few days after we talked, Oprah's TV show guest was Britney Spears. According to the description of the program on Oprah.com, "Britney Spears Performs Live ... See her sexier, edgier, new look!")

Asked in January if she intended to renew her contract, which expires in August 2004, Oprah said, "I haven't figured that out yet, but I feel more bodacious in stepping out and telling people what my message is."

As we know, she did renew her contract--until 2006. If she truly quits her show in four years, the question, indeed, is, What's next? In her interviews with FORTUNE, Oprah talked at length about her desire to do something more with her time and money, something significant. She's still mulling her options, and as uncertain as she is, she vows to continue to have a presence on TV. "She's not going to crawl into a corner," says King World boss Roger King, who guesses she will do network specials a la Barbara Walters. But the bodacious vigor she talked about is already taking her--and Harpo--in new, far-flung directions. In early April she plans to go to South Africa to launch the first international edition of O. Cathie Black and her colleagues at Hearst pitched the idea to Oprah last summer, but she wasn't ready. She changed her mind one night last fall while watching a documentary called Africa on PBS. One scene in a Nairobi beauty parlor showed customers reading Hello! and True Love magazines. Kenya and South Africa are 1,800 miles apart, but Oprah's instincts kicked in. "I thought, 'African women have no business sittin' in a beauty shop reading Hello! and True Love.' "

For the first time ever, she's considering licensing her name. Not Martha Stewart-style to build her company's profits, but Paul Newman-style to raise money for charity. She has talked with Newman about his Newman's Own salad dressings, popcorn, and other high-priced foods; the line has generated $125 million for the actor's causes. "It's a beautiful model," says Oprah, who has donated at least 10% of her annual income to charity, most of it anonymously, throughout her adult life. She's interested in working with a cosmetics company because, as she puts it, "cosmetics is something I know." Still, she's not quite there yet. In late February she met with executives from Estee Lauder, but decided she doesn't want to leap into such a big venture ... at least for now.

And then there are other projects, none of which has been disclosed publicly until now. She is building a school for girls in South Africa. During her April trip for O, she plans to meet with government officials and educators to discuss building a dozen or so more schools, and perhaps some medical clinics too. Oprah focuses on three causes: women, children, and education. "When you educate a woman, you set her free," says Oprah, who spent her early years in a house without electricity or running water. "Had I not had books and education in Mississippi, I would have believed that's all there was."

Sometimes the opportunities seem virtually unlimited, and that just stresses her out. "I don't care about being bigger, because I'm already bigger than I ever expected to be," she says. "My constant focus is on being better. Should I be doing multimedia video production? Or seminars on the Internet? How can I do what I'm already doing in a more forceful way?" Her companion and unofficial career coach, Stedman Graham, the owner of a leadership training and development firm in Chicago, constantly nags, "You're not doing everything you can do. You need vision!" Lately he has been prodding her to partner with the United Nations "to distribute her message all over the world." Oprah does not exactly embrace the concept. "Oh, my God," she says, "he told you about that?" She hasn't spoken to anyone at the U.N., she adds, "but now they're going to be calling me."

It's not easy being Oprah. People call. They make demands. They ask hard questions. After our last interview, she calls to tell me that she is never going to do another business story. "But this is just your first," I say. "And it's my last," she replies. "I'm not sure why I did it. I'm uncomfortable talking about money and money issues." She may be uncomfortable talking about it, but when it comes to making it, she sure knows what she's doing. And that's only part of the reason why the "what's next?" phase of her career should be one hell of a show.

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