Before he became the founder of Playboy magazine and built a whole $110 million empire, Hefner started as a budding cartoonist making comic strips as a child.
Hugh Hefner quit his job at Esquire magazine in ‘52 to pursue his dreams of starting his own publication. He got $8000 from investors to begin Playboy, purchased a photo of actress Marilyn Monroe for the first cover, sold 50,000 copies, and gained momentum from there to sell 700,000 each month in ‘56.
Hefner wasn’t always strolling around the Playboy Mansion in a silk robe – he grew up on the streets of Chicago and graduated from university with a Bachelor in Psychology and Creative Writing and Art.
Big Aspirations in a Strict Home
Glenn Lucius Hefner and wife Grace Caroline Hefner gave birth to Hugh Marston Hefner on the 9th of April in 1926. He describes home life as “conservative”, as his family were Methodist and wanted Hugh to embark down a rigid career path.
Attending Steinmetz High School, he established a passion for creative writing, making plays for his schoolmates and creating his own comic books.
After his graduation in 1944, he joined the Army. Although, he seemed to be more engrossed with drawing cartoons, and ended up writing for several newspapers within the military.
Following his discharge from the Army in 1946, Hef (a nickname coined to him by his family and close friends) went to the University of Illinois and eventually earned his Bachelor’s Degree, graduating in ‘49.
In 1951, he published a satirical cartoon book called That Toddlin’ Town, before landing himself a job with Esquire. Things took an unexpected turn when the magazine decided to move to New York.
During the move, Hugh asked for a raise of $5 per week, but was denied the promotion. Consequently, he left Esquire and made the decision to do his own thing.
A Small Loan That Led to Millions
Fuelled by determination and his dreams, Hefner approached 45 investors and ended up raising $8000 to start his own men’s magazine. $2000 of that money came from his own mother and brother, Keith Hefner.
He relied on the money from investors as he didn’t have enough funds to begin his venture.
“I of course had no money at all, none,” Hef shared in 2017 in an interview with The New York Times.
“I came alive that summer, I was tremendously confident.”
In order to boost interest for his pending magazine, he purchased some photos of up-and-coming actress at the time Marilyn Monroe in 1953. $500 was reportedly the cost for the rights to the images.
“I learned that a calendar company out on the west side of Chicago, very close to where I grew up, owned the rights to the already famous Marilyn Monroe, nude.”
Monroe and Hefner never actually met in person, but he did later pay $75,000 for his grave to sit next to hers in Los Angeles at the Westwood Village Memorial Park Cemetery.
It didn’t take long for the magazine to garner attention after its publication in ‘53, and it sold 54,175 copies. From there, it continued to grow and by the fifth year since the debut issue, it was selling 1 million copies per month.
He bought the Playboy Mansion in Chicago in 1959, and his variety show, Playboy’s Penthouse, began airing.
Iconic Figure in a World After World War II
It should have come as no surprise that Hefner would become such an icon for celebrating women’s sexuality, especially since he had become rather unhappy with the prudish tendencies of 1950 Americans.
“When I came out of [World War II], I expected something similar to the Roaring ’20s — a celebration,” he told Fortune in 2003. “Of course, what we got was the opposite. It was a very conservative time, a repressive time—politically, socially, and sexually.”