Most people tend to avoid things that make them uncomfortable. They won't let their finger get near the browser, open the book, or click on the show. I am no different. I typically stick to stories that align with my views and try and learn from people I want to emulate.

When it comes to leadership I am often reminded of the quote by Brian Tracy, "Move out of your comfort zone, if you want to grow." So I took a leap of faith and dug into one of the most polarizing and controversial entrepreneurs of the 21st century: Hugh Hefner. After watching 'American Playboy: The Hugh Hefner Story' on Amazon Prime and spending hours researching the story, I was surprised by what I learned from Hugh Hefner's experiences.

Know Who You Are and Who You Want to Put First

When Hefner broke away from Esquire to start Playboy from his kitchen table in 1952 after being denied a $5 raise, he didn't know who he wanted to be or who was important. As the magazine rose in popularity, he said, "I literally became a different person."

Hefner essentially abandoned his first marriage and his first born daughter just to build his business. He worked so much he slept at the office most nights. Hefner admitted he was only a father and husband on holidays, birthdays, and other special occasions.

If you don't start with a clear idea of who you want to be and the people who should come first in your life, when success and fortune comes your way, you risk losing the people you should have valued most.

The Path You Walk Matters

Sex sells, it always has. There are a lot of ways to build a business, but don't underestimate the way in which you build it. In Hefner's case, he built his business by commercializing women and nudity in a format unheard of prior to the 60s and 70s. It was and still is, a controversial and often frowned upon way to make a living.

There are arguments about the moral nature of the Playboy business, but at the end of the day you should be able to answer some simple questions about your profession:

  • Does it make me a better person?
  • Do the lives of the people who work with me improve by what we are doing (not just financially)?
  • Does my work make the lives of my customers better?

Surround Yourself with the Right People

Hugh did a phenomenal job of finding people to help take the business to the next level in the early days of the magazine. He didn't care where they came from, what their background was, or how well he knew them. If their strengths filled gaps in the business and they added to the organizational culture, he found a way to bring them aboard.

Own Your Core Business

Over the decades, Hefner and his team went well beyond producing a magazine. They were in the club, casino, and TV business among others. Hefner got great at his core business prior to finding additional ways to drive revenue.

Too often leaders try to be everything to everyone and end of being nothing to anyone. In order to compete in today's business environment and continue to grow, you will have to gain business outside of your core business. But before you do, learn a lesson from Hefner and own your core business first.

Ego is the Enemy

One of my favorite books of all time is called Ego is the Enemy by Ryan Holiday. Before I read the book, I didn't know how or why I needed to overcome my ego. Ego is simply our own self-centered, self-serving ambition. The desire to be more than, to be recognized for, or to be elevated above others.

Hefner's ego and the desire to live the playboy lifestyle was and continues to be bigger than the room. The question becomes, if all the money dried up, the company went away and all the bright lights were no longer shining, would people still want to be around him? Then simply ask yourself the same question: if it all went away, would people want you in their life?