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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