Early in his career John Castle was employed by the well-known investment firm Donaldson Lufkin & Jenrette. During the years of the 1960s-1970s Castle was put in charge of the Sprout Group, the venture capital division of DLJ. Castle was so successful in this capacity that he became the CEO of DLJ.
In 1986 Castle left his position at DLJ after the firm was bought out by Equitable. Embarking on a new path, he decided to join forces with two other former employees of DLJ, one of them being Leonard Harlan. After creating Castle Harlan in June 1987, by November of that same year the partners had amassed $125 million in seed money for their newly formed venture capital firm. In December, a mere one month later the team joined up with William Reagan of Outdoor Advertising and purchased a billboard company for $85 million.
This seemingly ordinary investment was a turning point for John Castle. Forming Castle Harlan was the beginning of a new career, and was meaningful to him. Castle describes the genesis of the deal in almost religious language.
Castle was at a meeting in Venice, where he met Reagan. This is how he explains the birth of the deal:
‘We were sitting in a plaza under a church spire one night,” recalls Castle. ”As church choirs sang, he persuaded me he was the guy to support to put this deal together.”
Castle’s contribution to the deal was $11 million, launching a new company which Castle says will be run in a similar fashion to Sprout, which earned an average yearly income of 25 percent. Castle says he is aiming for closer to 35 percent.