"In your belly you hold the treasures few have ever seen
most of 'em dreams, most of 'em dreams."

-Jimmy Buffet

When a friend turns a significant age, I give them a copy of Jimmy Buffett’s book, A Pirate Looks At Fifty.

You would not think that a guy who wrote, “Why Don’t Get We Drunk and ****”, would be reflective, but Buffett is.

Buffett sums up his life in a 400-word autobiography. It sets the tone for the reflection and dreaming that one does at a milestone age.

Bill Gates is 50.  Many were surprised when he stepped into a lesser role at Microsoft.  As a fellow entrepreneur, I was not surprised at all. 

Gates has done everything he wanted to do.  There is nothing else that another dollar or billion dollars can buy him.   He has reached the point where professional managers can take over the company without his guidance. 

Now Gates wants to make a lasting mark on society.

If he can live to an old age, we might find that Gates’ activism and charitable accomplishments will overwhelm his incredible achievements in business.

Even if Bill were retiring to hang out on the beach, it would be a good idea for him to transfer away from Microsoft.   Gates understood the lesson that many business founders don’t learn. The time to get out.

You see over and over again instances where entrepreneurs hang on too long.  They have spent their lives building a business. Once it is built, they either have nowhere else to go or nothing else to do.

Inevitably, the business starts to suffer and often fails.  The same skills that make you a great entrepreneur do not make you a great business manager. 

Entrepreneurs often become rich, but few have riches as their primary goal.  The best entrepreneurs are people with an idea who feel a need to tell the world about it.

It is more like evangelism than profit making.  There is great excitement as the larger world catches on to the ideas and concepts that the entrepreneur develops.   Once the business has grown to a certain level, management teams are brought in to develop systems and keep the gains that the business has made.

Gates has always had good managers.  Now it is time for him to get out of their way.

Gates and his wife Melinda started their foundation in 2000. Up to that point, Gates had never been a great philanthropist or active in charitable causes.  He was totally focused on building Microsoft.

Starting the foundation opened Bill’s eyes to the needs of the world.

The move away from Microsoft had to be easier when Gates realized that the next phase of his life had purpose and opportunity.  He is not a guy who wanted to hang around and talk about the good old days.  He needed a challenge, and global health is a daunting challenge indeed.

Focusing on his foundation will be good for the world.  It also will be good for Bill Gates.

As a pirate looking at fifty, Gates has gone through a period of reflection and decided to do something beyond creating wealth.

I am sure Bill Gates would shudder if he heard himself described as a pirate.  For him, piracy is associated with people who illegally  copy Microsoft products and do not pay the company royalties.

I associate Gates with the more romantic version of pirating that Jimmy Buffett conjures up.   I watched Gates as a contemporary who took on establishment corporations like IBM and won.   I admired his swaggering business success.  He was David taking on Goliath.

As Wilt Chamberlain aptly noted, no one ever rooted for Goliath.

Somewhere along the way, Microsoft became Goliath.  They are an establishment company like IBM, but that is not bad. Many companies like General Electric and IBM were founded by visionary leaders and produced fine products for generations to come.  

Now we will be rooting for the swashbuckling Gates as David, while he takes on the Goliath of fighting the world’s problems.

It’s a pretty good place for a pirate to be at 50.

Don McNay is Chairman of the Board at McNay Settlement Group and plans to live his life like Bill Gates has. You can write to him at This e-mail address is being protected from spam bots, you need JavaScript enabled to view it or read his columns at www.donmcnay.com.  His award-winning column is syndicated on the CNHI News Service.