6 management lessons from Hugh Hefner

Hugh Hefner

This week, we lost the founder of Playboy, multi-millionaire Hugh Hefner, at the age of 91. His approach to life was a controversial one, but there’s no question that he was a profound businessman and a shrewd entrepreneur.

Here are a few management lessons from the man behind the bunny ears.

Surround yourself with the best of the best

The list of notable names that used to frequent the Playboy mansion – or the pages of Playboy itself – is a lengthy one. Everyone from Norman Mailer and Margaret Atwood to Mort Sahl and Miles Davis.

It brings to mind the advice we hear from successful CEOs again and again: hire smart people. Surround yourself with brilliant, capable, superstar employees that will help you grow your business.


Hef once said, “It’s good to be selfish. But not so self-centered that you never listen to other people.”

Simple words, but worth repeating. Talking to your employees – and really listening to what they have to say – is crucial to being a good leader.

Be loyal

Here’s an excerpt from Hefner’s obituary in the New York Times:

“Friends described him as both charming and shy, even unassuming, and intensely loyal. ‘Hef was always big for the girls who got depressed or got in a jam of some sort,’ the artist LeRoy Neiman, one of the magazine’s main illustrators for more than 50 years, said in an interview in 1999. ‘He’s a friend. He’s a good person. I couldn’t cite anything he ever did that was malicious to anybody.’”

Loyalty breeds loyalty – if you stand by your employees, they’ll stand by you. Particularly in startups and emerging businesses, fostering loyalty and trust among your team can make or break your success.

Hugh Hefner 1953 Dec Playboy Cover_Marilyn MonroeChoose (and set) your goals wisely

When the first issue of Playboy came out, the publisher’s note read “We don’t expect to solve any world problems or prove any great moral truths.”

Granted, he arguably went on to cause a cultural revolution and start a national discussion about sex, freedom of speech, and more. (“The 1950s were a buttoned-down time,” writes NPR. “but Playboy was unbuttoned.”)

But that first publisher’s note is key. Hefner knew what he wanted to do with the magazine, and he outlined it clearly and succinctly. If you take this approach to every goal you set, your team will thank you.

Take copious records

Interesting fact: Hefner held the Guinness World Record for the largest collection of personal scrapbooks, and even employed a full-time archivist (Steve Martinez) to care for nearly 3,000 volumes.

“Nobody has more completely self-documented his own existence than Hefner,” explained Esquire in a 2013 article.

“The earliest single volumes, which are remarkable – featuring Hefner’s childhood cartoons and report cards; a picture of Hefner as a baby with the caption ‘Our hero at six months in his first formal portrait’; the receipt he gave his mother, Grace Hefner, for her $1,000 investment in Playboy – might document a few months or even a year. Later volumes might capture only a single month. Today’s volumes span only three or four days. So every Saturday, without fail, Hefner comes up here and sits down at the desk next to the little oval window, puts on some Bing Crosby or Frank Sinatra, and fills a few dozen more plastic sleeves while Martinez works away beside him, collecting captions, double-checking the order of things.”

The moral of this anecdote? Keeping good records (or “self-accounting” as it’s sometimes called) can turn you from a good boss to a great boss. Taking copious notes and painstakingly organizing info for the future can help you with everything from performance reviews to brainstorming sessions. Try it.

Lead by example

“Hefner was an ongoing advertisement for his own product,” wrote the Globe and Mail, “the pipe-smoking, silk-pajama-wearing centre of an A-list, X-rated party.”

In other words, he lived and breathed his brand. And while your small businesses likely won’t require you to take on Hef’s approach, you should definitely be leading by example. The goes for your product, but it also for company culture, office etiquette, and more.

Pay attention to detail

Even after a stroke in 1985, Hefner was still a very active editor-in-chief of Playboy (In fact, he held the Guinness World Record for the longest serving editor in chief of a magazine). But it was his hands-on approach that was so noteworthy; his staff reportedly called him “the world’s wealthiest copy editor” for his attention to detail.

Don’t be afraid to get in there with your team, solving problems and making sure that things are running smoothly. However, keep in mind that there’s a difference between attention to detail and micromanaging – be sure to steer clear of the latter.

Don’t waver on your principles

There’s no shortage of stories of Hef putting it all on the line for a principle. When he began his “deadening slog into 1950s adulthood,” he took a job in the personnel department of a cardboard-box manufacturer, but quit when he was asked to discriminate against black applicants.

When he was a copywriter at Esquire, he was refused a $5 raise – so he left the company. When the US Post Office wouldn’t deliver Playboy, he took it to the Supreme Court.

Fighting for what – or who – you think it is right can be challenging, or even scary. But it shows a strength of character that your team will remember.

(Photos courtesy of Playboy)

See also:
Management lessons from NASA’s James Webb


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