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Lesson #5: Be Ready to Fail

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Staff post about: Hugh Hefner
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When Hefner was asked to describe his ultimate fantasy, he said simply, “I’m living it.” But, Hefner’s path to success has not been as smooth as it might appear. Experiencing numerous failures along the way, Hefner came to understand that failure was a natural part of achieving success. Had he given up upon encountering obstacles, he would have sacrificed his multi-million dollar empire and the world would not have known Playboy Enterprises or its now-infamous rabbit logo.

While his first venture with the Playboy magazine received unparalleled success, Hefner was not so lucky with his next pursuits. He expanded within the publishing world with two magazines called Show Business International and Trump, neither of which had a very long shelf life. He also initially ventured into the world of television with the late-night show Playboy Penthouse, but it too found little success. Despite these failures that occurred early on in his career, Hefner did not give up on the idea of branching out and expanding the Playboy brand. “There are many roads to Mecca,” says Hefner. Indeed, when one road collapsed, Hefner was not hesitant to try another.

When Hefner first ventured into the world of casinos and betting parlors, he was operating with profits. But, as competition increased and Hefner’s licenses began to be revoked both at home and in the United Kingdom, the Playboy empire started to suffer. The Playboy website was also initially a money loser for the Playboy empire. With its soft-core focus and fee-based membership, it simply could not compete with other websites. By 2003, losses from their company’s Internet operations had grown to over $70 million.

It was through sheer determination and willpower that Hefner continued towards his dreams of creating an empire. “A lot of us walk through life in lock step, just following whatever’s been done before and not really thinking about it,” he says. But, by surrounding himself with quality people and continuing to think creatively, Hefner was able to make it past the failures he experienced. By continuing to focus on putting out a high quality magazine and personally espousing the type of lifestyle it praised, he was ensuring that the Playboy brand could still be marketable in other areas, despite his previous failures.

“Not to suggest that my life hasn’t been full of trials and tribulations,” says Hefner. “Of course, it has. It wouldn’t be a life without it. But I know how lucky I am.” The company still pales in comparison to other public media companies. It employs only 660 people, compared to 85,000 by Time Warner. In Playboy’s best performing year, it was still dwarfed by companies like the Walt Disney Corporation, which earned more in two days than Playboy had all year. Hefner has often expressed disappointment that his company has not become a billion dollar operation. But, Playboy remains one of the world’s most recognized brands and has revenues in excess of $330 million. Not bad for a little bunny in a tuxedo.


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