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The Self-Made Man: Hugh Hefner

Since we’re pretty much all guys here at TSB, I don’t think I have to explain who Hugh Hefner is. After all, Playboy introduced a lot of guys to the glories of women, specifically what they look like naked. In fact, many of our most personal intimate moments were probably curated, to one extent or another, by Hugh Hefner. I’d say we all owe him our thanks, but I don’t think he’d appreciate getting those kinds of letters in the mail. Not from dudes, anyway.


But before Hef was a weird old man in silk pajamas with a private porno collection that would make Caligula blush (or so Linda Lovelace told it), he was a daring entrepreneur who, as the New York Times put it, ?did for sex what Ray Kroc did for roadside food: clean[ed] it up for a rising middle class.?

Hefner started Playboy after quitting a copywriting job at Esquire and deciding that he didn’t want to bust his ass just to make someone else rich. Like many entrepreneurs before him, he thought that busting his ass to make himself rich was a better use of his time.

More specifically, Hef saw room in the publishing world for a gentleman’s magazine with a touch of class. Men’s magazines back then had pin-ups, of course, but they were either too campy to be taken seriously or too dirty to buy from a newsstand. Hefner’s idea for a men’s magazine was essentially a guide to urban bachelorhood, with regular lifestyle columns, short fiction from well-respected authors, and celebrity interviews. In short, what Playboy offered was naked pictures of hot girls and more than a little advice about how to impress those hot girls. He was selling a culture as much as, and maybe more than, the magazine itself.

With this concept in mind, Hefner raised $8,000 of start-up cash (which was a lot of money in the early 50s) from a variety of investors, including his mother, to start up the magazine. The first issue sold 50,000 copies, mostly due to Hefner being brassy enough to publish a 1949 nude calendar photo of Marilyn Monroe that no other magazine would touch due to that era’s strict obscenity laws.

Hefner officially ran afoul of those laws in 1963, when he was arrested for selling obscene literature because an issue of Playboy had nude photos of Jane Mansfield in it. The jury couldn’t reach a verdict though, possibly because they kept taking the primary evidence into the bathroom with them, so Hef was free to continue publishing highbrow smut and get rich doing it.

What’s important to keep in mind about Hefner’s success is that it wasn’t a soulless cash grab based on a cursory examination of the market ? his business plan was informed by a philosophy that he believed in and lived by. Once he had the ?what? and the ?why? figured out, the ?how? wasn’t as daunting as it might have been otherwise.

For more on that, here’s a clip of Hugh Hefner from the good old days, discussing his Playboy philosophy with William F. Buckley, Jr.

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About Dave Kiefaber Dave Kiefaber is a Baltimore-based writer who regularly contributes to Adfreak and the Gettysburg Times. His personal website is at

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