In 1958, Wolff took a job as a real estate appraiser in St. Louis. In 1961, his company sent him to Los Angeles to open a regional office and in 1963, he co-founded a real estate consulting firm. In the 1960s, he was very successful developing the booming San Diego market and earned a solid reputation in the industry. In the 1970s, he accepted a position with 20th Century Fox tasked with managing its worldwide real estate investments. Wolff's approach - which he would successfully apply throughout his career - was to find partners willing to fund the majority of the investment and take a more passive role, which would allow Wolff to directly manage the investment himself.