In 1994, Wolff founded Maritz, Wolff & Co with Philip Maritz in St. Louis, Missouri. The company owned interest in eighteen hotel and resort properties around the world, including the Fairmont San Jose Hotel, the Fairmont San Francisco, the Carlyle Hotel, the Four Seasons Hotel Nevis, the Four Seasons Hotel Toronto, and the Park Hyatt Sydney. In 2011 Wolff and his partner, Philip Maritz, orchestrated the $800 million sale of five hotels, including The Carlyle and the Rosewood Management Company to New World, a Hong Kong-based real estate and hotel company.