By Carlye Adler; Hugh Hefner

(FORTUNE Small Business) – Hugh Hefner is the first to admit that he's the "luckiest guy on the planet." At 77 years of age, he lives on a $50 million Los Angeles estate and has seven live-in girlfriends. Not that we're going to get into the details here--sorry.

Fifty years ago Hefner started Playboy from his Chicago apartment. By the time the company went public in 1971, Playboy had grown into an empire, including nightclubs, hotels, casinos, a modeling agency, a record label, and a limousine service. Hefner's bunny logo has become so famous that there is a rabbit species--the now-endangered Sylvilagus palustris hefneri--named after him. And Playboy still outsells all other men's magazines. From the mansion he calls Shangri-la--which he shares with a few squirrel monkeys, 65 caretakers, seven scantily clad women, and one albino peacock--Hefner talks about the worldwide brand he has built and how he did most of it while wearing his pajamas. --CARLYE ADLER

"A moment came in early 1953 when I felt as if my life was over. It was the result of having gone back to high school for an alumni show my best buddy and I hosted. In the last year of high school I deliberately invented a persona: I started referring to myself as "Hef" after Betty Conklin, a girl I had a crush on, rejected me. I changed my entire wardrobe. I started wearing yellow cords and saddle shoes--cooler clothes. I began using cooler expressions and actually started writing a cartoon autobiography of my life. I was living in a microcosm of what came later with Playboy. When I started doing that comic strip, I was creating a world of my own in which I was center stage. I was very popular.

I had not had that kind of life since high school. It was being at that reunion and thinking about "Hef"--and all that I had been in school--that motivated me to create Playboy. So the spring of '53, I started making plans for the magazine.

I had always been interested in publishing. I created my first penny newspaper when I was 10 years old. (I don't remember how much I made--if anything.) I did another one in seventh grade called the Pepper, which lasted for a quarter of a century. Later I created a little magazine called Shudder, about horror and mystery movies and radio shows and books. While I was in college, I edited a college humor magazine called Shaft, where I introduced a feature called Co-Ed of the Month.

That idea came out of the movies and the pin-up pictures. Early on I escaped into the dreams and fantasies that I found in the music and the movies of my childhood. I was born to a very typically Midwestern, Methodist, Puritan home. It was a very loving home, but not a home in which there was expression of love--no hugs, no kisses. It was quite lonely. Growing up during the Depression--and looking back at the images and music of the Roaring '20s and the Jazz Age depicted in silent films and by F. Scott Fitzgerald in The Great Gatsby--I felt that I had missed the party. It was kind of like arriving at a party on a Sunday morning; the dirty dishes are there, but the party's over.

I went into the Army in the spring of 1944, right after graduation from high school. When I came out of the war, I expected something similar to the Roaring '20s--a celebration. Of course, what we got was the opposite. It was a very conservative time, a repressive time--politically, socially, and sexually. The skirt lengths in the 1950s went down, rather than up as they had in the '20s. I thought that was a very unfortunate sign.

During the war the girl I carried on a correspondence with was Millie, who would become my first wife. We had started going steady after high school. After I came out of the war, I went to the University of Illinois--largely because Millie was there. While I was in college, the first Kinsey report came out on the sexual behavior of the human male. I wrote an editorial about it and commented that I thought it was the most important booklet of the year. I did postgraduate courses at Northwestern University in sociology and psychology, and I did a research paper comparing the statistics in the Kinsey report and U.S. laws. I got an A for the research, marked down to a B+ for my conclusions. When I did the paper, any form of sexual behavior that was not for procreation was considered immoral or illegal. I said that the laws were inappropriate and should be changed. I had these dreams.

At the time I had the idea for Playboy, I was working as the circulation director of Children's Activities--a children's magazine. Prior to that I had worked for Publisher's Development Corp. as circulation manager. It produced a variety of magazines, including a couple of men's magazines: Art Photography and Modern Man. Before that, I worked at Esquire in its promotional department. They were moving the rest of the company to New York. I asked for a $5 raise; they declined, and I decided to stay behind and start a magazine.

The problem was that I had no money. I got a $600 loan against my furniture from the local bank. I went to my family and asked if I could borrow some money from them, or whether they would invest in the magazine. My father declined. He was an accountant, and he didn't feel that a magazine was a good business investment. My mother took me aside and said that she had some money of her own, and she would give me $1,000. She didn't believe in the magazine, but she believed in her son. My brother Keith, who was working in Baltimore and New York City as a children's TV show host named Johnny Jellybean, sent a couple of hundred dollars every week, investing a total of $1,000. That money and the $1,000 I got from my mother were my two largest investments. The total investment that launched Playboy was $8,000. You don't start a national magazine with that kind of money. Of course, I didn't know that I couldn't do that, so I went ahead and did it.

I Was going to call the magazine Stag Party and use a stag in a tuxedo or a smoking jacket as the symbol. Then, about five weeks before the magazine went to press, I got a cease-and-desist letter from the lawyer for Stag Magazine, saying Stag felt that the title would be an infringement.

I was starting to have some second thoughts about the name anyway. It didn't have as much of a romantic connection as it might have. We put together a list of names--"we" being a couple of buddies of mine and myself. A good friend's mother had worked for a small, unsuccessful car company called Playboy. My wife thought the name might not work very well because it seemed to be related more to the Roaring '20s. I thought we could take that generic name and actually make it our own.

The centerfold in the magazine was going to be called Sweetheart of the Month, and once I had Playboy as the name, we changed it to Playmate of the Month. The joke page was originally called Stag Party Jokes. We simply changed the name to Party Jokes. There was going to be a stag illustration on the first double-page spread in the first issue, so we had the cartoonist draw a rabbit head and paste it on top of the stag. That first drawing of the rabbit actually has a rabbit's head, but it has hooves.

Most of the men's magazines after World War II were outdoor adventure books. True, Argosy, Stag--they were all about hunting and fishing and things I didn't care a great deal about. It was The New Yorker and Esquire that influenced me most. Both magazines had male figures as logos. The notion of using a rabbit in a tuxedo seemed frisky, fun, sexy, and sophisticated.

We introduced the rabbit symbol on our second cover, and it continued throughout the years. The rabbit is always, in one form or another, on the cover of the magazine. It's sometimes hidden, sometimes simply a little beauty mark, or a reflection in a girl's eye, or a knot in a bikini. The symbol became world famous very quickly. In the 1950s we received a letter from the East Coast with no address but the rabbit. Then we knew we'd arrived!

I was looking for some kind of a special gimmick for the first issue of Playboy because I had no money to promote it. Movies in 3-D and comic books were very popular at the time. So I thought about doing a nude pictorial in 3-D and putting those little glasses in every issue. I actually shot the pictorial--and then discovered that it would be too expensive to buy all those glasses. But at that same time I discovered that the Marilyn Monroe calendar--which everyone had heard about but nobody had seen--was owned by the John Baumgarth Calendar Co. out on the West Side of Chicago, very close to where I had grown up. So I drove out to Chicago and talked to John Baumgarth, and I walked out of there with the rights to the Marilyn Monroe calendar and the color separations--all for $500.

I wrote letters to the various wholesalers and distributors around the country, many of whom I'd gotten to know from having worked with the earlier magazines. I told them that some of the guys from Esquire had stayed behind and were creating this great new magazine. I assured them it would have the famous Marilyn Monroe nude calendar pictures in the first issue.

In truth the magazine was my card table and a typewriter and some letterhead and me. When I wrote to the distributors, I was the general manager of American News Co., and when I wrote to agents and writers, I was the editor of Playboy, and when I wrote to potential advertisers, I was advertising director. I wore many hats.

I got orders for 70,000 copies. But I didn't put a date on the first issue because I didn't know if I'd have enough money for the second issue. Then Empire News Co., a small, independent national wholesaler that had turned me down initially, took us on. That gave me a little solvency.

The political climate at the time was very conservative, but the response to the first issue of Playboy was phenomenal. We sold about 52,000 copies. The second issue--without Marilyn Monroe--sold even more. We got letters from young people all over the country. At the time I didn't really fully appreciate what I had created: It was the first successful magazine for young, single men.

The idea to use naked girls in Playboy came from serving in the war--that was the time when pin-ups enjoyed major celebrity because soldiers pinned up the pictures on the barracks. The pictures were drawings done by George Petty or Alberto Vargas, and they were inside men's magazines. There were also pictures of movie stars like Betty Grable. The concept behind the Playboy playmate was the pin-up. I invented the centerfold, though--both the term and the idea. I put a three-page foldout in the center of the book so people would open to it--and it was something sexy. What we created with Playmates was artistic. We put the girl into a natural setting and introduced the suggestion of a male presence in the picture ... there would be a second glass, or a pipe, or a necktie. It was intentionally a situation that suggested the possibility of seduction. Although I think it was kind of at an unconscious level at the time, the message was that nice girls like sex too.

For models we chose the girl next door, not just professional models. When I had enough money to shoot our own centerfold, the first one was our subscription manager, and a girl that I was dating at the time. (By 1955, Millie and I were pretty much separated.) I invented a name for her--Janet Pilgrim. I told a little story about the fact that she worked at the magazine. That caused an absolute sensation. The message: Beautiful women like Janet Pilgrim were everywhere. It's not only in Hollywood or the glamour girls in New York. Beautiful girls are on your college campus, they are in your office, they live next door to you. That was, in 1955, a revolutionary idea.

In the very first issue we had fashion features, and we had a piece on cooking, which was very unusual for a men's magazine. We discovered very early on that the identification with that magazine was so dramatic for many readers--it was an extension of their lives.

As successful as we were, I had absolutely no idea--how could anyone have imagined?--what was ahead in the next decade. In 1959 we held a jazz festival in Chicago for our fifth anniversary. In the next few months I started hosting a nationally syndicated television show called Playboy's Penthouse. I bought the first Playboy mansion on Chicago's Gold Coast, and I opened the first Playboy Club. At the end of 1959, I came out from behind the desk and started living a life. It was something that I thought would be fun that would also work as a marketing ploy. That's when I started smoking the pipe and driving a 300SL Mercedes-Benz. Before long, I'd become world famous. All that was quite a conscious decision. And one can see now--I didn't think of it in those terms then--I was doing the exact same thing I did in my 16th year, when I reinvented myself in high school.

I now had a broader platform for the ideas I'd been trying to spread since college. In December 1962, I started writing Playboy Philosophy, an editorial series about what I hoped would be the coming sexual revolution and about our hypocrisy related to sexuality. Having a philosophy became an obsession for me, and I used Dexedrine (to help me stay awake) and worked around the clock. In the spring of '63, I wrote a couple of installments about the arrest of comedian Lenny Bruce and about the inappropriate association between church and state in Chicago. In June the police came and arrested me. There were four of them--they all wanted to come to see the inside of the mansion. They said they were arresting me because of a pictorial that we ran on Jayne Mansfield, but since the pictures were really no different from any of the others that we'd run, it's clear the reason was that we were criticizing the government and attacking the connection to the church. Anyway, the city eventually dropped the case.

Sales of Playboy went through the roof. The magazine's circulation climbed to a little more than a million in the 1950s--we passed Esquire. Throughout the '60s and the very beginning of the '70s, circulation climbed from one million to seven million. It was a period of tremendous growth and change for us. We expanded into book publishing with Playboy Press and into movies. Our first film was actually Roman Polanski's version of Macbeth.

Things were pretty great until the '80s, when the Moral Majority, the Christian right, got Reagan into the White House. He paid them back by establishing the Meese Commission, which did a witch hunt across the country and declared anything sexual pornography.

My daughter, Christie, came to work at Playboy in the late '70s, about a year after she graduated from Brandeis. In the early '80s, Christie came to me and said that she wanted to take a shot at running Playboy. In a certain sense I always turned running the business over to other people. The first business manager was my college roommate at Illinois. And my father worked as the treasurer of the company. It was nice to know he was there watching the money.

And I was tired. At the time, Playboy was being attacked from many quarters, not only from the religious right but even from the liberal left, because the feminist movement had embraced a kind of antisexual, anti-Playboy attitude. It was the beginning of political correctness. It was a dumb and crazy time. I suffered a stroke--as a result, I think.

We're now fighting a different battle against a whole new batch of competitors. In its 50-year history Playboy has become the most imitated magazine in the world. Earlier, Penthouse and Hustler cropped up--Penthouse was even named after my TV show, Playboy Penthouse. But those magazines were much less classy versions of what we were doing. The circulations of both of those magazines are essentially nonexistent today.

The new concept magazines, including Maxim, Stuff, and FHM, are also variations on the Playboy theme, and they are doing well on the newsstands and with advertisers. I take that competition very seriously. I'm not taking them on alone. I've hired good young people to help me. We brought in the top guy from Maxim and the managing editor from Rolling Stone, and the Playboy now on the newsstand is a revised variation--it reflects the arrival of the so-called laddy books.

Despite the new rivals, Playboy is still the single largest-selling and most influential men's magazine. Maxim has over two million circulation. We have over three million--and our largest growth in circulation is in Maxim's demographic. Most telling: There are more references to Playboy in rock music than ever before--we call it Hip Hopping Hef.

Some say we might be antiquated, but that's the price you pay for being around for a long time. It's natural to think that we are more old-fashioned. I think of our history as a giant edge, though, because entire generations have grown up with us. Men remember finding a copy under their parents' bed or in their father's shirt drawer--and they remember the Playmates in a romantic way, the way one remembers a first girlfriend. Playboy, for many, many people, was an unforgettable rite of passage.

Of course, the miracle is that we lived through half a century of history, survived it, and we've won. The past four or five years, for the company and for me personally, have been the best of my life. Looking back, I'm definitely proudest of the fact that I made some difference in changing social and sexual values of my time in a positive way. When you're living all this day by day, you have no idea what you're going to accomplish, and certainly no idea what lies ahead."