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When Main Street Messes Up Your Wall Street Plans

Posted on September 5, 2015May 26, 2025 by Paul

I once made a guy tens of thousands of dollars on the stock market. I had a system. It worked. Twice. I never got a dime from him in commission or anything. Don't even recall the guy buying me lunch. That's just how it goes sometimes. They walk away with thousands, you walk away with nothing.

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I studied for my Series 7. That's the test you have to take if you're going to sell stocks and bonds. I always liked the stock and bond business and thought I could do well at it.

I used to get up at 4 am and watch CNBC. Anything I could learn I figured I could learn there.

After studying for the test, I went to take the test, of a version of, at a lot of local financial firms. Legg Mason Wood Walker, Prudential, Goldman, Amex -- passed them all. In fact, they all wanted me to come and work for them.

The first thing every one of them asked was this: How many high net worth people do you know?

Um. None.

I soon found out that instead of  actually helping people make a lot of money, I was going to spend all my time on a phone bank.

"Hello Mr. Jones. I understand you have an IRA. Would you like to transfer your IRA to a ROTH IRA. If so, we would be happy to help you. Indeed I see here you have a Whole Life Policy. We can also transfer that into a Term Like policy and you can then use that monthly payment savings to either bulk up your IRA or invest in our excellent annuity."

Cold calls. 8 am to 6 pm. Months on end. Years maybe.

They said they'd help me get a Series 7, but I also needed a Series 63 - I was going to be a glorified insurance salesman. I'm out.

Main Street messed up my Wall Street plans.

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Months later I was talking with a friend. By then I had come up with my own system for making others money and helping them. Here's that system:

I read Barron's weekend Edition cover to cover. Every word. Every line. Every single thing it said. Everything. Even if it were one sentence.

I turned on CBNC on Monday Morning. If from 4 am to 7:30 am they mentioned the same thing - ever how briefly - that was where the money was going to be.

My friend owned a lot of AOL stock. The news report that weekend was "FedEx reports that this holiday season they expect to ship 80% of all packages".

That was in Barron's -- Monday morning one of the first things I heard after 7am was that. I called my friend and said, "get out of AOL and into FedEx, now". He made tens of thousands of dollars.

A few weeks later it was earnings season. I read a report about the possibility of an AOL stock split. It was reported on CNBC as well. I called my friend, "get out of FedEx and back into AOL". He did. It split. He now had twice the stock as he had before. Then the stock continued to climb.

$74,000 by my calculation. That's what he made. I made $0.

Man, to have money at times like that. To even be compensated for your advice and ideas. No harm no foul. It is what it is and had he actually compensated me, we may have even broke NASD laws and rules, who knows.

That works though. I ran a "test" using that method for a while and it did then (to be clear - this was some time ago and this is not investment advice, it's just me telling stories). It's not a bad one. I never once heard or read of anyone else using it or doing it.

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You have to do what makes you happy. Mostly. There's a fine line between doing what makes you happy and surviving sometimes, but I knew this was something that wasn't going to provide either for a number of years. And life is short. I didn't have a number of years. Not then. Not now (even though I'm going to live another 70 or so years).

I couldn't sit in an office all day, in sunny SWFL, and make blind calls to people I didn't know and harass them about their finances. That wasn't the business for me.

Had I been able to do research on businesses or hedge one against the other - do puts and calls and really contribute, I might have been all in. Calling and selling insurance and the new IRA, I'm out.

Just another idea. Another Pivot. Moving on.

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    Open Doors and Opportunity – it’s what we wake up each day hoping to find.

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    It’s been a crazy life – with highs and lows not experienced by anyone who ever “played it safe” — but I was born to live, and so, that’s what’s I’ve done. These are just some of those (all true 100%) stories.

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