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Do You Love Your Business as Much as Hef Loves Playboy?

Hugh Hefner said his life would be over without his company. Here’s how to avoid a similar fate.


Hugh Hefner says his life would be over without his company.


Last year, a New York Times reporter quoted 84-year-old Hugh Hefner as saying, 'If I sold it (Playboy Enterprises), my life would be over.'

If your workday entailed lounging around in a robe at the Playboy mansion, most guys could see why you might not want to give it up.

But assuming your business is a little less—ahem—sexy, could you imagine life without it? Some psychologists have likened the sale of a business to the loss of a child in terms of its psychological impact and sense of loss for the founder. I think there are some steps you can take now to lessen the letdown.

When I started Warrillow & Co., my name was literally on the door. In the beginning, I was so desperate for it to succeed that I poured all of my waking hours into the business. My hobbies and relationships started to wither from lack of attention. I rationalized my schedule, saying that once I got the business going, I could get back to 'my life.'

After a while, the business did get off the ground, but I never changed my work schedule. The source of my drive evolved from necessity to the adrenalin rush I got from building a successful company.

It all started to come undone in 2004, when the departure of an employee made me feel personally rejected. This employee was an important part of our team and managed one of our key relationships. She was going to a great job with a big multinational firm, but I felt betrayed.

The loss of this popular employee triggered the departure of a number of other workers soon afterward. I was left with a skeleton staff, a troubled business and a bruised ego.

The whole experience made me realize just how much a part of my personality my business had become—and just how personally I was taking things associated with it.

Eventually, I picked up the pieces and rebuilt the company. But, like a person who had been betrayed in a relationship, I became more hardened and started to look at my business as an inanimate economic engine instead of a defining aspect of who I was.

Rather than continuing to give all my time to my business, I vowed to get back in touch with the people and things that were important to me.

I stopped putting 'life' off and started to get one. I taught myself how to windsurf again. I bought a mountain bike and competed (that's a charitable way of describing my performance) in a three-day stage race. I started running; I bought skis and a snowboard and organized an annual trip with old friends. In short, I got back in touch with the things I like to do.

Now that I am no longer working in my company day to day, I do miss the people. However, for the most part, I don't miss the business itself because the void has been filled with other relationships, hobbies, interests and investments that I started nurturing long before selling my company.  

When I look back, I'm glad I had a near-death experience in my business as it forced me to nurture outside interests and investments in my life before I actually attempted to sell.

As for Hef, my guess is that all of his interests can still be found at the office.  

John Warrillow is a writer, speaker and angel investor in a number of start-up companies. He writes a blog about building a sellable company at You can also follow him on Twitter at @JohnWarrillow.

Last updated: Sep 1, 2010

JOHN WARRILLOW | Columnist | Sellability

John Warrillow’s new book, The Automatic Customer: Creating a Subscription Business In Any Industry will be released on February 5, 2015. John is also the author of Built to Sell: Creating a Business That Can Thrive Without You and the founder of The Sellability Score, a company dedicated to helping business owners improve the value of their company.

The opinions expressed here by columnists are their own, not those of

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