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The Essential Wingman

Jim Houtz, Founder and Chairman, Southwest Jet Aviation

I've been an entrepreneur for most of my life, ever since founding CyCare Systems in the 1960s, and I've also always had an interest in aviation. In fact, Southwest Jet Aviation, the company I most recently launched, is a provider of services such as charter, hanger, and aircraft maintenance management.

Thus, I can't be helped for turning to aviation lore to explain to today's entrepreneurs that what they must do to build great companies is adopt the attitude of the fighter pilot. That is, they must always be in control of the plane; they must be the person calling the shots.

However, something else separates the great fighter pilot from the true ace, and it isn't exceptional skill, daring, education or weapons accuracy - those characteristics are given. Instead, aviation lore has it that what makes the difference is the pilot's wingman - the individual flying in the cockpit beside the fighter. A great wingman gives the pilot the chance to be great.

Similarly, the essential number two gives the entrepreneur a chance to be successful. Think of Steve Ballmar to Bill Gates at Microsoft, "Charlie" Munson by the side of legendary investor Warren Buffet, or Mort Myerson who ran Ross Perot's operations for years.

In Praise of the Wingman

In the same tradition is Dick Burgmeier, who played that role for me at CyCare Systems, which I founded in 1967, ran for 29 years, and sold in 1996 for $270 million to Atlanta-based HBOC Inc.

CyCare Systems was a pioneer in the group medical practice billing and insurance software systems business, for years maintaining a 35 percent share of the market. That, in no small part, was due to the people I was able to recruit. This group included executives such as Ron Grey, the chief financial officer who got us ready for our initial public offering (IPO) in 1981; David Mitchell, who built our professional sales force; Harry Moore, who weaned us from batch processing to modern technology; and Jim Dyer, who eventually took over from me as CEO.

They were great, but it was Burgmeier who was the wingman. He joined shortly after I founded the company, when our staff numbered a scant 15 and stayed on for 19 years before leaving in 1986 - only to return five years later for another four-year stint. In his 23-year tenure, CyCare Systems metamorphosed from fledgling to fast growth and again, with its listing on the New York Stock Exchange in 1988, into maturity.

Throughout it all, Burgmeier wasn't necessarily in training for the fighter pilot's job. Indeed, that may or may not be the outcome for the wingman. At Microsoft, Ballmar did succeed Gates as CEO. At CyCare Systems, on the other hand, when it came time for me to step down, I turned to Jim Dyer instead, for his marketing prowess.

What It Takes

In short, the wingman's role is different from that of executives in functional specialties, as are the qualities one must possess to fulfill the role.

At its most basic, the job isn't one for the person selected by flipping through resumes and hoping for the best when the hire comes on board. It is a role best filled with someone the entrepreneur knows personally - and respects greatly. I met Burgmeier in the early 1960s at IBM, where he was working in systems and I in sales. From my observations, I could see that he possessed tremendous knowledge of data processing management, the equivalent of today's chief information officer's role. In fact, given his likely future at IBM, it took some convincing to lure him to my start up.

As skilled as he was, he possessed talents that were different from mine, which is also essential for a company's second-in-command. In the early days, ours was the classic Mr. Outside, Mr. Inside split. While I was busy pursuing customers - it was I who elected to go after group medical practices rather than municipalities, the alternative opportunity in those days - Burgmeier was forging the operation that would serve those customers.

As Mr. Inside, he created the company's guts - its data-processing operation in Dubuque, Iowa - eventually building a staff of 250. In the process, he solved problems as they arose, such as having suddenly to service 35 rather than 10 accounts during a period of especially fast growth. With Burgmeier, it was never a matter of my telling him what he had to do, but rather his telling me what he had done. In short, he took responsibility and ran with it.

A good wingman must have an outstanding degree of integrity, and that characterized Burgmeier as well. I don't think he could tell a lie if his life depended on it, which was more than just a matter of moral exactitude. It was critical for a small company in the throes of building lasting relationships with customers.


When I named Dyer rather than Burgmeier to the top job in 1984, I took comfort in knowing how Burgmeier would react: I knew that he would want what was best for the company. This is what lies at the heart of the job that is essential for the making of an entrepreneur. As I said, a good wingman makes it possible for the pilot - or the entrepreneur - to be successful.

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