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The financial advisor first caught the attention of Winfrey with her interactive television show, Can I Afford It?, where Orman counseled callers on aspirational purchases. A regular guest on The Oprah Winfrey Show, Orman also has a monthly column in O magazine and she costars with fellow Oprah protégés Dr. Phil and Dr. Oz on the viewer-advice show, Ask Oprah's All Stars, airing on OWN.