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After graduating from the University of Pennsylvania Roberts and his friend Joel Rosenman tried to pitch a story for a television series about entrepreneurs who had more money than ideas. Each week their antics would get them into a new series of problems.
Roberts and Rosenman had met at a golf course in 1966 and shared an apartment in 1967.
To do research they placed an advertisement in The Wall Street Journal identifying themselves as "young men with unlimited capital" who were looking for business ideas. Among the 5,000 responding were Michael Lang and Artie Kornfeld who proposed building a recording studio in Woodstock, New York to encourage recordings by local residents Bob Dylan, Jimi Hendrix and The Band. Eventually this idea was dropped in favour of staging an outdoor music festival.
As they developed a plan it was clear there was no area around Woodstock that would meet their requirements, they then moved it to Wallkill, New York. Following protests from local residents they moved to its eventual location in Bethel, New York.
The concert cost between $2.4 million and $3.1 million to produce and brought in $1.8 million from gate receipts. While the producers would make money on the movie and soundtrack of the events, Roberts said he would not get out of debt from the event until 1980.