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He attended North Beach Elementary School, Northwest Junior High and Miami Beach High School. A few years after he graduated from Miami Beach High, he moved to New York. Through a friend who worked in management there, Cayre landed a job at Columbia Records International overseeing sales of Spanish-language music. He was only 20 years old at the time. Cayre took to the business, and soon wound up running his own company, called Caytronics, which went on to become a leading Spanish-language record and music publishing company during the 1970s. Cayre sold that company to RCA Records for $125 million, and he retired when was 39 years old. The retirement did not last long. By the early 1980s, Cayre was getting ready to parlay his success in recorded music into a profitable video business. He started GoodTimes Entertainment in 1984. The start-up of GoodTimes led Cayre to a fateful meeting with Sam Walton, legendary founder of retail colossus Wal-Mart. The meeting resulted in GoodTimes Entertainment becoming the sole distributor of videos to Wal-Mart for 10 years. After running GoodTimes for most of the succeeding 10 years, Cayre finally cashed in his equity and sold it in 2003 for $280 million to Quadrangle Capital Partners.

Venturing into Real Estate: Around the time he founded GoodTimes, Cayre had started diversifying his personal net worth by investing in real estate, initially with a partner in the Washington market. As the commercial real estate market nationwide went south during the late 1980s, a cold call led Cayre and his two brothers to invest in more than 100 properties in Manhattan that a big savings bank foreclosed on. According to Cayre, he paid 1 percent down, no interest for 5 years, no principal for 2 years.

Midtown Equities LLC: From Miami Sun Post: Joseph Cayre is the chairman of Midtown Equities, a family-owned and -operated real estate investment company based in New York City. The company owns properties in Washington, D.C., New Jersey, New York, as well as Florida. Other principals of Midtown Equities include his son Jack Cayre, Michael Samuels, and Daniel Pfeffer.

World Trade Center: Joseph Cayre's most well-known asset is an interest in the 99-year-lease to the former World Trade Center property. Six weeks before the 9/11 attack in 2001, NY developer Larry Silverstein and investors Lloyd Goldman and Joseph Cayre bought the 99-year leasehold of the World Trade Center. From The New York Times, Mr. Silverstein put up about $14 million of the $800 million in fees and down payments. He raised about $110 million from the Goldman real estate family and Joseph Cayre. The group borrowed $563 million from GMAC. The deal gave the Silverstein group control of 10.6 million square feet of WTC office space. The Port Authority, which built and owned the trade center, valued the original deal at $3.2 billion. Two years after the attack, the group got back $98 million of the $125 million initial equity they invested. (also see "911 review")

Sears Tower: In March 2004, Joseph Cayre, along with NY investors Lloyd Goldman and Jeffrey Feil bought the Chicago Landmark Sears Tower from MetLife for $835 million. MetLife said it realized an after-tax gain of $90 million on the deal. ("WSJ")

Other Real Estate Deals: Joseph Cayre signed on as a development partner for the 56-acre Buena Vista Yards in Miami Florida. The $1.2 billion project includes 600,000 square feet of retail space, 3,000 condo lofts and 350 apartment units.(Read more here, here and here.) Cayre's Midtown Equities is also developing the Steel Point Development in Bridgeport, CT, a $1.5 billion, 52-acre mixed use project consisting of 3,500 residential units, 1.1 million sf of retail space, 160,000 sf of office space, 400-slip marina and 12 acres of streets and roads. (Read more here.)

Joseph Cayre and Douglas Jemal: In September 2006, Joseph Cayre testified in the bribery and conspiracy trial of one of the most prominent DC developers Douglas Jemal. From Washington Business Journal: Joseph Cayre says he's made more than $100 million with Jemal, more money than he'd made on any other individual deal. He says he and Jemal still own more than half a dozen properties together, with his share totaling another $100 million. Cayre told the jury that he would do more deals with Jemal if the developer put up collateral. When pressed by prosecutors whether Cayre would put money into a deal based on Jemal's word, Cayre said: "If he gave me his word he would give me some collateral." Jemal was eventually acquitted of the bribery charge and convicted of one lesser count of wire fraud.