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My 8-Year-Old's Portfolio Will Kick Your Portfolio's ...

NEW YORK ( TheStreet) -- When I graduated high school, I was one month away from turning 18 years old. At that point, I already had my future mapped out for more than a decade. I was going to be the next Howard Stern.

Less than two years out of high school (1995), I moved to Miami and took my first full-time radio gig doing nights on a sports talk station. The next several years of my life looked a lot like the movie Private Parts, minus the lesbians and ultimate smashing success in the radio capital of the world, New York City.

I even dealt with program directors like "Pig Virus." (He's a real person, by the way).

At day's end, I had a moderately successful career, but after about a dozen years on the radio I decided it was not for me. Or maybe radio decided "I wasn't for it."

In any event, before I left home my radio jobs paid by the hour. I think the most I made was $15 per. My summer job at the local housing authority delivered a better wage. In Miami, where they pay you with sunshine, I made a wimpy $26,500 a year. Welcome to the big leagues, kid!

Through it all, I invested in DRIPs (Dividend Reinvestment Plans) and a smattering of mutual funds. As I made more money, I started buying stocks. As I made more money, I bought more stocks.

I became obsessed with the stock market at a relatively young age. I enjoyed more than moderate success investing. I only got my rear end handed to me once -- actually several times. Each time came during the 1999-2000 dot-com boom.

Other than do not chase IPOs, the biggest lessons I learned were:
  • Do not sell right when the power of compounding is about to go to work for you; and
  • Do not sell prematurely because you're getting impatient with a stock.
  • I unloaded 100 shares of McDonald's (MCD) from a DRIP in 1997 to buy a couch or something stupid. In 2000, I took profits on 500 shares of Petsmart (PETM) at four-something a share. Don't look up the price. It even hurts me when you do it.

    Fast forward to 2012 and I am an 36-year old man with a kid about to morph into a 9-year-old. Insane.
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