Of all the pleasures Winfrey can afford, she says her greatest indulgence is a private jet.
"I would say having your own airplane is the greatest luxury," Winfrey tells Edward Enninful, the editor-in-chief of British Vogue. "Because it means one minute you're in New York, and then the next minute you say, 'You know Edward, I think I'll fly to London.'" (Of course, such a spontaneous jaunt racks up a lot of carbon emissions.)
Winfrey first decided to purchase her own jet in part because of an experience in an airport in 1991, when a woman accosted her while she sat waiting for her flight.
"I was in the airport and I was just minding my own business, and a woman came up and she said, 'You're not acting like you do on TV,'" Winfrey remembers. At that time, Winfrey was starring in "The Oprah Winfrey Show, " the program that catapulted her to success. "On TV, you're hugging everybody, and you're just sitting here not hugging," the woman said.
For some more privacy and a lot more convenience, Winfrey bought a jet. At one time, she reportedly owned a Bombardier Global Express XRS worth an estimated $42 million.
"That was my all-time goal because the asset I value the most is time, and that bought me time," Cuban tells Money.
Cuban bought a $40 million Gulfstream V in 1999, according to The Wall Street Journal, and owned three planes by 2010.
“Since I’ve owned the [jet] there are too many examples to count of how the airplane has helped me, " Cuban said. "Flying out after a late-night game to be at a meeting the next morning. Leaving a meeting to get home in time for my daughter’s first daddy-daughter dance. It’s part of my life that I can’t be without.
“It means I have more hours in my day to spend with friends and family. It means I can get more work done. It means I can travel comfortably with my family. It’s a life- and game-changer.”
Winfrey agrees: “It’s great to have a private jet. Anyone that tells you that having your own private jet isn’t great is lying to you,” Winfrey told The Wall Street Journal in 2009. But she issues a reminder that success isn't all about accumulating expensive toys. “You haven’t completed the circle of success until you help someone else move to a higher ground and get to a better place.”
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