Winning Ways

David Gartland

ROGER PENSKE STARTED as a race car driver, but soon found he’d be better off as a team owner. Penske’s holding company also has stakes in Penske Truck Leasing, among other businesses, as well as the Indianapolis Motor Speedway, home of the Indy 500.

One of Penske’s criteria when hiring race car drivers: select folks with a burning desire to win. Penske has said he can guide a driver’s thinking about the best way to pursue wins, but he can’t teach someone the will or desire to win.

At the track, he’s called “the captain.” He has a team of managers who oversee the pit crew, mechanics, statisticians and driver coaches. But when he gets on a driver’s radio, everyone else shuts up and lets Penske coach the driver.

In most cases, he’s calming the drivers down because they’re like pit bulls in a dog fight. They want to kill. This is the energy that Penske wants. He just needs to harness a driver’s fight so the team benefits—meaning the driver wins.

Notice what Penske said about the desire to win. He can’t teach that. It either exists inside the driver or it doesn’t. We all want to win or, at least, not lose. The difference lies in our willingness to focus all our energies on winning.

How important is winning to you? To me, it’s not that important. I don’t focus on winning. Instead, I concentrate on not losing. That’s a big difference.

A stock purchase that increases by 10% is a winner, but not a great winner. By contrast, a 10-bagger is a winning stock that soars to 10 times your original purchase price. To pick a 10-bagger, you either need to really know what you’re doing or you need to get very lucky. But to pick a stock that increases by 10% usually just involves waiting a little while.

Hitting home runs is hard. Hitting singles is easier, and they get you on base. Both are winning activities. The difference is how you define winning.

According to psychologist Daniel Kahneman, most of us would rather not lose than win. The joy of winning is dwarfed by the pain of losing. The important thing is to understand who you are. Must you have major wins to feel good, or would you be satisfied with minor victories? Minor wins occur more frequently, so they offer the chance to feel good more often. Who doesn’t want to frequently feel good?

Many amateur gamblers want to be big winners. They say, “Put it all on red.” When they hit red, bells go off. At that moment, if they took their money and walked away, they’d probably be ahead. But in many cases, they say, “Let it ride.” The result usually isn’t what they wanted.

By contrast, professional gamblers go for minor wins. They play the sure things, even if the winnings aren’t great per hand. The more winning hands they have, the more their gambling earnings grow. They take the money and walk away from the table, knowing there will always be another game tomorrow.

If Penske was your coach, would he need to control your pit bull fight, or could he simply let you drive your race and get the points for finishing? Unrestrained pit bulls don’t win every race—and, in fact, they often crash out. Less aggressive drivers are easier on the equipment and bring home an un-wrecked car, so the vehicle is ready for the next race.

The same notion applies to investing. Do you tend to go for the big win, often leaving you broke? Or are you happy to get through the year unscathed, ready to collect further gains next year?

David Gartland was born and raised on Long Island, New York, and has lived in central New Jersey since 1987. He earned a bachelor’s degree in math from the State University of New York at Cortland and holds various professional insurance designations. Dave’s property and casualty insurance career with different companies lasted 42 years. He’s been married 36 years, and has a son with special needs. Dave has identified three areas of interest that he focuses on to enjoy retirement: exploring, learning and accomplishing. Pursuing any one of these leads to contentment. Check out Dave’s earlier articles.

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