[5] He attended New York University but dropped out to work at the real estate company of his uncle, Sam Borchard.

[5] He soon left his uncle's firm to work for Webb & Knapp, a small New York building manager and brokerage.

The real estate tycoon and his company, Webb & Knapp, also were involved in theme park investment following the successful debut of Disneyland.

In December 1958, Zeckendorf entered into a deal with Spyros Skouras, head of 20th Century-Fox, to purchase Fox's project to develop 176 acres (0.71 km2) of its historic backlot in Los Angeles, California, into a proposed US$400,000,000 (equivalent to $4,224,221,453 in 2023) Century City.

The studio had suffered a string of expensive flops, culminating in the box-office disaster Cleopatra (1963) and was in dire need of money.

The project, conceived under the direction of Edmund Herrscher, the studio's director of property development, had been announced the first week of 1958, with construction said to begin in July 1958.

Zeckendorf hired New York public relations executive Tex McCrary to lend new life and visibility to the project.

McCrary, in turn contracted with Los Angeles publicist Charles A. Pomerantz, well known in the entertainment industry, to come up with a campaign and execute it.

Thorne said that it should be a large affair with the mayors of Los Angeles, Beverly Hills, and Santa Monica, plus politicians and other dignitaries, invited, as well as all the Southern California press.

In 1960, Zeckendorf solved his problem by partnering with Alcoa in a joint-venture relationship to finally build Century City, which by now had escalated to a US$500,000,000 (equivalent to $5,149,606,299 in 2023) project.

From the start of his career Zeckendorf had been able to use his dealmaking skills to acquire or build projects for which he lacked the funds, but in time the under-funding caught up with him, and "his overextended company crashed in a spectacular bankruptcy.