4 Entrepreneurial Takeaways From America’s Playboy

On September 27, as everyone knows by now, Hugh Hefner, founder of Playboy magazine and a handful of related ventures, died at his home, the Playboy Mansion, at the age of 91. Whether you want to call him a misogynist and a maniac or a visionary and tycoon, there’s no denying that the late Hugh Hefner left an indelible mark on American culture.

For better or worse, he played a catalytic role in America’s sexual revolution and built a multi-million dollar business empire along the way. But what lessons can we learn from his business success? Here are a few:

It’s all about how you handle failure.

Failure is imminent. It doesn’t matter how successful you are now, or how invincible you feel; you will eventually encounter failure — and probably more than once. When Hefner first started, he almost immediately experienced success. However, he wasn’t quite so fortunate in other business pursuits. He tried his hand at two more magazines, both of which failed rather quickly. He also started a late-night TV show called Playboy Penthouse, but it too was rather unsuccessful. The same could be said of his Playboy website and casinos and betting parlors around the world.

It would have been easy for Hefner to throw in the towel and quit, but he kept on pushing forward and let the failures feed him. “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,” Evan Carmichael wrote on his website.

Embody your business.

When you think of Playboy (the brand), it’s impossible not to think about Hefner in his silky robe with a gorgeous woman on each arm. In fact, how many times can you remember seeing him not wearing his iconic robe or escorting a younger woman?

Part of the reason you never saw Hefner without these things was that these things defined him. There was little differentiation between Hefner the person and Hefner the founder of the Playboy empire. He embodied his brand in every way.

There’s tremendous risk in closely associating yourself with your brand, but there’s also the opportunity for great reward. Hefner understood this from the beginning to the, end and it’s part of what made him so successful. If you want people to believe in your brand, you have to believe in it yourself.

Know when to evolve.

As mentioned above, Hefner wasn’t afraid to try new things. As a businessman operating in an era when digital media overtook print media, he was someone who was okay with pivoting in order to satisfy new marketplace demands.

When circulation of Playboy magazine dropped from a height of 5.6 million in 1975 to around 800,000 just a few years ago, Hefner decided to move in a more digital direction. The website stopped trying to compete with the porn industry and instead switched over to non-nude, soft-core content that allowed the brand to grow a social media presence and reach a slightly younger audience (18-to-30-year-old millennials).

There have been some speed bumps in the Playboy evolution, but the long-term trajectory has always been to stay relevant and keep up with how people are consuming content.

Surround yourself with the right people.

If you had asked Hefner about his business acumen, he probably would have told you that he wasn’t that good of a businessman. While most people would argue the contrary, he was always pretty adamant about the fact that he simply surrounded himself with good people who covered for his deficiencies.

As Hefner once said, “The business end of business has never interested me.” Hefner was drawn to the marketing and editorial side of Playboy, but knew how to surround himself with people who could help the business thrive. In fact, one of the smartest decisions he ever made was in hiring female advisors who could write on the topic of sex from a totally different perspective than any man would ever have.

What will you be remembered for?

It’s unclear what the conversation will be like when people sit down and discuss Hefner’s life in six months, 10 years, or 50 years — but one thing is clear: We’ll still be talking about him. Some will scold him for his sexist view of women, while others will admire him as a sex icon. But regardless of his personal viewpoint, Hefner will always be seen as one of the great entrepreneurial minds of the 20th and 21st centuries.

The question is: What will you be remembered for? When your career and life are over, what will your peers, business partners, employees and customers remember about you? You might not have the same public recognition as Hefner, but that doesn’t mean people can’t learn a thing or two from you.

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