4 Gems Hugh Hefner Taught Us About Entrepreneurship

Anthony Holloway
TechDirtyWithMe
Published in
4 min readJul 17, 2018

Last week I started watching a documentary series about Hugh Hefner and how he built the Playboy Magazine empire.

Some might have questioned his Playboy lifestyle, but there’s no denying his business savvy and impact on the magazine industry.

Here are 4 nuggets of entrepreneurial wisdom from The Playboy himself, Hugh Hefner.

Seek Work That Puts You Into Flow State

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Hefner once said, “The business end of business has never interested me.” Hefner was drawn to the marketing and editorial side of Playboy, but knew how to surround himself with people who could help the business thrive.

We’ve all been in a state of flow before. Those days where hours seemed to fly by in a matter of seconds. We literally lose track of time.

It’s that “optimal state of consciousness where we feel our best and perform our best.”

Hugh knew what his strengths were and focused intensely on them.

As a kid he doodled, made his own comics, and even created alter egos for himself. Writing was his passion, and without it, Playboy couldn’t have existed or thrived.

Point is, we should all pursue activities that put us in flow state. Whether it’s dancing, writing, or even playing video games…

There’s actually a guy makes up to half a million dollars a month playing video games… 👇

Pursue what puts you into flow. Especially if that activity doesn’t pay the bills (initially)!

Because if we dig deep, beneath our flow state exists the work that we’re meant to do. The person we really are.

Writing and editing put Hugh into flow state.

Seek to discover your Flow.

See The Bigger Picture

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Hefner was adamant about surrounding himself with people who could shed light on his blind spots and help transform Playboy into more than just a magazine.

“One of the smartest decisions he ever made was in hiring female advisors who could write on the topic of sex from a totally different perspective than any man would ever have” — Entrepreneur Magazine

Hef was great at writing, but his strongest talent was being able to see the big picture. He strategically put others in positions to succeed.

More importantly, the culture at Playboy was that everyone’s ideas were included. Without this environment, great ideas couldn’t truly flourish.

Hef was able to see the big picture because of his curiosity.

He was a voracious listener and knew EXACTLY what his audience wanted. And how they wanted it.

So always be actively listening. Adding value never gets old 😎!

The Obstacle Is The Way

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In 1952 Hefner was a 26 year-old copyrighter at Esquire magazine.

It was literally his dream job!

However, the Esquire that inspired him as a kid had changed it’s style. Which discouraged Hefner. So when he was denied a $5 raise, he split.

A year later, with a small loan of $600, and $8,000 raised from 45 investors, including his own mother, Playboy Magazine was born! — Business Insider

Sometimes even your dream job can let you down.

And often times the “HARD WAY” is the route of most growth.

The route where we stretch and become better than imaginable.

Don’t sacrifice your Dreams for your “dream job”!

This isn’t a declaration to quit your job to follow your dreams.

However, consider this a call to action.

To not hide from opportunities to flourish.

We’ve got to run towards them.

Don’t be denied.

Put in the work.

Be Bold

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Obstacles are inevitable. But what’s most important is that we remain true to our values while on our journey.

Why?

Because knowing our values makes decision making nearly EFFORTLESS.

Case in point…

In 1959 Playboy debuted Playboy’s Penthouse.

The show gave Playboy Magazine readers a glimpse into Hugh Hefner’s lavish Playboy lifestyle, every bachelor’s dream at that time!

But what was most impressive was Hefner’s unwavering belief that only the best Jazz musicians would be on the show. And in his opinion, many of those musicians were Black.

Artists like Ella Fitzgerald and Nat King Cole.

For context, this was during the height of the Civil Rights Movement!

Many southern TV stations refused to air it because Blacks and Whites were not segregated in the show.

Despite these threats, Playboy’s Penthouse aired and was a smashing success.

We must be bold and live through our values.

“It’s not hard to make decisions when you know what your values are. “ — Roy Disney

Above all, have fun.

Seriously.

- What are your values?
- What dreams are you trying to manifest?
- Is there a “dream job” holding you back from your true dreams?

Want help figuring out what to puruse?

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Anthony Holloway
TechDirtyWithMe

Recruiter. Coach. Chief Editor of @TechDirtyWithMe. altMBA Alumni. StartingBloc Fellow. Math Geek. Foodie.