Ivan Boesky, infamous stock market trader during the go-go 1980s, died this week at the age of 87. Boesky’s obit was front-page news. He made a fortune from insider trading before serving prison time for securities manipulation.

Boesky was an inspiration for the Gordon Gekko character in the 1987 movie Wall Street. Boesky’s death also serves as the inspiration for my article today.

Let’s take a break from the market’s daily ups and downs to examine insightful investment lessons from the dark side of The Street.

Oliver Stone’s morality play about greed on Wall Street introduced the world to one of the most unforgettable rogues in cinema history: the corporate raider Gordon Gekko.

Michael Douglas won a Best Actor Oscar for his vivid performance as Gekko, the ruthless financier whose reptilian nature is reflected in his name (a gecko is a type of lizard).

The Reagan Eighties was a time of flamboyant greed. Boesky memorably said in a college commencement address: “Greed is alright, by the way. I want you to know that. I think greed is healthy. You can be greedy and still feel good about yourself.”

Echoing that sentiment in Wall Street, Gekko says: “The point is, ladies and gentleman, that greed, for lack of a better word, is good.”

Stone, who wrote and directed the movie, says he learned about the markets by observing his father Louis, who worked as a stockbroker for more than 50 years. This knowledge shows in the script.

To assist your wealth accumulation efforts (aka, “greed”), I’ve culled the seven best tips from Gekko the Great. They constitute timeless advice, showing that you can learn good things from a bad guy.

Gekko Tip No. 1: Remain dispassionate about your investments.

Goodbye is often the hardest word. You can get emotionally attached to an investment, just as you can with a person. And, as with a personal relationship, it’s hard to bite the bullet with an investment and call it quits. Sometimes your head tells you one thing, but your heart another.

You need to listen to your head, and remain coldly rational about your holdings. When a stock, bond, or mutual fund has soured and it’s time to sell, don’t agonize over it. Dump it.

As Gekko advises: “Don’t get emotional about a stock. It clouds your judgment.”

Gekko Tip No. 2: Do your research.

Gekko tells his protege Bud Fox (Charlie Sheen): “The most valuable commodity I know of is information.”

Successful investors do their homework. Think of financial statements as a company’s medical charts, and you’re the doctor who’s using these charts to come up with a diagnosis as to the company’s health.

And of course, you can always rely on the research and advice of the seasoned experts at Investing Daily.

Gekko Tip No. 3: Understand your investments.

There are too many worthwhile investments out there for you to shoulder undue risk by taking a shot in the dark.

It’s never a smart move to put your money into a company that you simply don’t understand. As Gekko says: “I don’t throw darts at a board. I bet on sure things.”

Gekko Tip No. 4: Be a contrarian.

The herd mentality is hard to resist; most investors behave like lemmings and march right off a cliff. They succumb to the “group think” of the media, friends, the Internet, colleagues, family…everyone telling them what stock or investment to buy, everyone ready with brilliant advice.

But here’s a general rule of thumb: Once your barber, cabbie or shoe shine guy starts giving you hot stock tips, it usually means the market has hit a peak.

Gekko puts it this way: “Ever wonder why fund managers can’t beat the S&P 500? ‘Cause they’re sheep, and sheep get slaughtered.”

Remember: Everybody does well in a bull market. But don’t mistake a bull market for brains. Be a contrarian investor. If the herd points in one direction, move in the other.

Gekko Tip No. 5: Learn to spot the snake oil salesmen.

Don’t be swayed by smooth-talking brokers trying to peddle dubious investments.

It’s hard to say “no,” because we all want to be liked, but protect your money by having the courage to push away high-pressure salesmen who claim to be on your side. Gekko expresses it this way: “If you need a friend, get a dog.”

Gekko Tip No. 6: Read Sun-Tzu’s The Art of War.

The Art of War is an ancient Chinese military treatise written by Sun Tzu, a high-ranking military general and strategist. It was all the rage during the 1980s to find lessons in the book applicable to modern life, especially in business.

The book does indeed contain nuggets of timeless wisdom that you can apply to the art of making money. In particular, Gekko offers this Sun Tzu quote: “Every battle is won before it’s ever fought.”

In other words, through preparation and doing your homework, you can guide the future outcomes of your investment returns.

Gekko: Tip No. 7: Play your cards close to your vest.

Gekko was by nature mistrustful. When it comes to your investments, you should be the same way. The world of investing is a digital one. Problem is, computer hacking incidents are ballooning in frequency and severity, making cybersecurity a top concern around the globe.

According to a recent report from CyberCrime magazine, the global price tag for cybercrime will exceed $10.5 trillion annually by 2025, in the form of fraud, theft, repairs and loss. Scams abound, as the Bernie Madoff affair sadly proved.

Carefully guard your log-ins, passwords and financial data. Your life savings can disappear in a single hacking incident. Resist the urge to blab about your portfolio.

In the midst of a sensitive deal, Gekko yells at his staff: “I want zip-locked mouths!”

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John Persinos is the editorial director of Investing Daily.

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