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How a Third-Generation Military Guy Gets to Wall Street

Bill Clinton was a master politician. Our politics do not jive, but you have to give the guy credit—he knows how to work a room.

I had an opportunity to meet Clinton when I graduated from the Coast Guard Academy in 1996. He spoke at the ceremony, and my father and grandfather, who had also graduated from the Academy, were there as well. We were one of the few three-generation families.

When I went up to receive my diploma, Clinton said to all three of us, “Thank you for your service.” Now, my father and grandfather hated this guy. But at that moment, they were beaming from ear to ear.

The Turning Point

After graduation, I was assigned to a ship in Port Angeles, Washington—a small, rainy town on the Olympic Peninsula. During my time there, a couple of women from outside the military came to talk to us about a financial product they were selling. They called it “assurance” and posted slides showing that $50 from every paycheck could grow into thousands of dollars. The growth rates they advertised were incredible.

There was no discussion about whether your money was invested in stocks or bonds or anything else. It was pure magic.

Remember, I was 22-years old at this point. It was before I worked on Wall Street, and before I knew anything about finance. I had no clue what these women were talking about. And I wasn’t going to put my money in something I didn’t understand.

However, some of the people on my ship invested in this “assurance” thing, authorizing automatic withdrawals from their paychecks. A couple of months later, we found out the whole thing was a Ponzi scheme. They lured in early investors, didn’t invest the money in anything, and paid fake “returns” with the money they got from later investors.

Everybody lost money. All together, they swindled about $3 million from military folks. That’s as sleazy as you can get.

As I was watching this unfold, I felt completely helpless. I couldn’t tell if it was legitimate or not. Of course, if I had known what I know now, I would have torn them apart. It would have been easy to tell this thing was a fraud.

That’s when I decided to take responsibility for my own financial education. I started buying financial books and learning about the markets. Eventually, that led to graduate school, a job on the P. Coast exchange, a job at Lehman Brothers, and then my own financial newsletter business. Even today, I make it a point to never stop learning.

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Every War Is Different

If I had stayed in the military, I would look at the war in Ukraine through a military lens. But I didn’t stay. So, while I am as disturbed as anyone about the humanitarian element, and I still know a lot about the military, I approach the situation like a trader because that is what I am.

Every war is different. In the month since Russia invaded Ukraine, we’ve talked about concrete steps you can take to insulate yourself from the potential financial fallout of the war. Specifically, keeping $10K in cash in a home safe and owning some gold—two good ideas in any environment, war or no war.

Many of my readers have asked for more actionable investment ideas… stocks that should outperform as the war plays out and the West boosts defense spending. That is why I wrote The Wartime Portfolio, an easy-to-follow blueprint for trading through the war, with seven tickers to buy now. Click here for more details.

Jared Dillian
Jared Dillian

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