Tips and strategies from the Hugh Hefner school of business

The man who created Playboy is as savvy a businessman as they come. Here's what you can learn from him.

January 29, 2017

A multi-millionaire with a bevy of beautiful women constantly at his beck and call, Hugh Hefner must have performed an incredibly noble deed in a past life.

He is of course the man behind Playboy, the publication that changed the face of men's publishing forever, and even though he's now just a tenant in the famous mansion to its new 33-year old owner, he is still worth about $50 million. 

Whatever reservations you may have of a business that was based on scantily-clad, sometimes nude, women and the notorious grotto parties, its undeniable that one could learn an awful lot of business acumen from the 90-year old. Turning a niche magazine into a global brand and business worth an estimated $500 million does not happen by chance. 

Here are six business pointers we've taken from Hefner's career. 

Don't be a pushover

If Hugh Hefner was a pushover, there would be no Playboy. Why? Because in January 1952, a young Hef was working as a copywriter for Esquire and believed he deserved a raise. He wasn't asking for much - just $5 - but his boss disagreed and denied him the salary increase. 

Hefner's next step was a simple one. He handed his notice in, left the company and began working on an idea to launch his own publication, that would of course become Playboy. Whoever his boss was, we thank you. 

Take risks

Hefner's first big risk (after leaving his job, of course) was to borrow $8,000 from 45 separate investors in order to finance the opening of Playboy in 1953. As well as the financial risk, Hefner also took a huge chance on the very first issue, when he decided that he would run the famous nude calendar photo of Marilyn Monroe.

The iconic actress had posed for the photo before she became a star, and while the photo's existence was common knowledge, no magazine had dared to publish it for fear of being sued. However, Hefner knew that if Playboy was going to be a success it needed to push the boundaries, so he went for broke and ran the picture.marilyn monroe playboy cover.

Sure enough, the first issue was an instant success, selling out its entire print run of almost 54,000 copies. Nowadays a mint-condition copy of that first edition would set you back at least $5,000. 


Having conquered the publishing world, Hefner could easily have rested on his laurels, content with a successful magazine, but a true entrepreneur always strikes when the iron is hot and Hefner did exactly that, sensing there was an appetite for the Playboy brand as more than just a magazine.

Hefner launched several new ventures. Some of the projects - a TV programme and two other magazines - failed, but many others succeeded, including a chain of members-only nightclubs and several casinos.hugh hefner Stick to your morals

With the huge success of Playboy a raft of imitators emerged, all trying to get a slice of the new magazine segment that the brand had created. The likes of Hustler and Penthouse had some success, releasing more and more revealing images and pushing the boundaries even further.

In this situation the most obvious thing to do would have been to go head to head with the new competitors and try to beat them at their own game, but Hefner had other ideas. Instead of compromising his morals and publishing what he considered to be "lowbrow" content, he focused on improving the literary content of the magazine, including articles from esteemed writers such as Tennessee Williams, P.G. Wodehouse and Ken W. Purdy.

Again, this set Playboy apart from the other titles which mainly focused on nude photos, and the result was that Playboy was considered a far more sophisticated option for the young gentleman, rather than a smutty dose of profligate. hugh hefner Create a strong brand

In 1953, Playboy's first art director, Art Paul, reportedly designed the famous Playboy bunny logo in just 10 minutes. Although Paul was the skilled pen master, the creative force was all Hefner. Hef decided he wanted to use a bunny for the logo but he still wanted to keep an element of sophistication, so he figured that the bunny should be dressed in a tuxedo.

Two years after the logo was made the company began marketing Playboy cufflinks - the first of many licensed products to come out of the brand. Today the world-famous Playboy bunny is one of the most recognisable logos in the world, on a par with the likes of Coca-Cola, Nike and McDonalds, adorning everything from clothing to glassware. playboy bunny cufflinks Know when to ask for help

The 1980s was a tough year for Playboy Enterprises as it suffered some serious setbacks, including the closure of a number of casinos, a drop in magazine circulation figures and, in 1985, a stroke for Hefner himself. 

While the boss made a full recovery, it became clear that the company needed a new lease of life. So in 1988, Hefner stepped down from his role of running the day-to-day operations and handed it over to his daughter, Christie.

Under Christie's leadership, the magazine picked up thanks to the inclusion of a more diverse range of topics, and the company grew as a whole with the launch of a premium TV channel and a paid-for website. 

Today, the business is still strong even though its encountered some challenges in recent years, and there were rumours it was to be sold. Just this month it was announced that a new Playboy Lounge and Supper Club would return to New York City for the first time in 30 years, and another is due to open in Shanghai in March. 

While Hef may not be the main man with the reigns anymore, it's undeniable that he was the driving force for one of the biggest privately owned media and lifestyle companies in the world, and the face of a global brand – minus the ears.