My Best and Worst Trades - TheStreet

NEW YORK (TheStreet) -- I have been trading stocks since I was 13 years old, in 1968.

The first trade was memorable. I bought $200, 10 shares, in a computer timesharing company called Datamation Services. For me, it was a very big deal.

I did it through a broker, using a custodial account, and when it got to $80/share, I said sell. Unfortunately it was a custodial account -- the broker told my parents not to sell. They didn't, and the company soon disappeared, taking my $200 with it.

I kept the certificate as a souvenir, alongside a 1921 Irish bond from my great-aunt, hand-signed by Eamonn DeValera himself. As she was fond of saying, after a few drinks, "up the rebels."

Since then I have had a great fondness for discount brokers, the kind that let me do my own thinking and initiate my own trades.

I haven't always been right, of course.

For one thing, I've managed to lose a lot of money on what's now

Apple Inc.

(AAPL) - Get Report

. I bought into it in the 1990s, while it was wobbling from one CEO to another. Soon after Steve Jobs returned, I got tired of waiting for gains and cashed in my chips, which is one reason I still work for a living.

Also see: The Dumbest Fee in the Airline Business>>

I took another flyer on Apple last year, and naturally my timing was impeccable. I'm out about $5,000 so far. I'm certain that all Tim Cook's problems would be quickly solved if I just sold my stake. When I do, I'll let you know.

I can laugh about Apple because, by and large, my investing is profitable. I call broker

Charles Schwab & Co.

(SCHW) - Get Report

my "bookie," and when I decide to buy something, tell friends I'm placing a "bet" with "Charlie." He takes a very modest "vig," under $10, even when I'm betting thousands, and I never have to wait for my winnings -- the teller window is always open.

My best trade ever is probably


(INTC) - Get Report

, which I picked up around the time I bought my first Apple shares. Intel doubled, split, and so I sold 100, my original stake. It doubled again, split again, and I sold 100. By the end of the decade, I had thousands of dollars in profits and 600 shares.

I've made money on


(IBM) - Get Report



(COST) - Get Report

. I've broken even on

General Electric

(GE) - Get Report

, and lost a little on

Red Hat

(RHT) - Get Report


All this is done through a retirement account, called a SEP IRA, and so I don't think about tax implications and just go for the capital gains.

Whenever I have any stake in any investment I write about for

, in that SEP IRA, it's disclosed at the bottom of the piece. You may see that I am long on


(GOOG) - Get Report

. If by long, you mean I own 10 shares, then I'm pretty long. I doubt Larry Page stays awake nights worrying about me.

I am not an expert. I'm an ordinary investor, like you. When the market goes up, I make money. When the market goes down, I lose money. At one point, in 2009, my IRA was worth just $140,000, instead of the $220,000 I'd pushed into it over the years. Now I'm more than whole. Charlie says I'm ahead by $33,000, but the memory of 2009 lingers - had I panicked I might be retiring with a tin cup in my hand.

Also see: Bond Risks Rising>>

The point is, I have no special insight. I write for

as a reporter. I'm not a big investor, not a banker, and certainly not a big swinging, uh, moneybags. I'm not a "player," just one of the guys in the stands, in a corner of the press box, looking for the free coffee and doughnuts.

And I have one more investment "tip," my very best trade.

Back when I was writing for ZDNet, after it became part of


(CBS) - Get Report

, I pushed all my money into mutual funds, because my employer said it was the ethical thing to do, and I feared losing my job if I didn't do the ethical thing.

One of those mutual funds tracked the

S&P 500

, and is run by my bookie. The

Schwab S&P 500 Index

(SWPPX) - Get Report

is up by 16%, but compounded that's $15,000. I don't think about it, I let others think about it, and I think it's my best bet of all. Except, perhaps, for Aunt Till's bond.

Up the rebels.

At the time of publication, the author was long AAPL, SCHW, IBM, COST, GOOG, and SWPPX.

This article is commentary by an independent contributor, separate from TheStreet's regular news coverage.