(written for this thread∞, not posted)

To actually answer the question: I've only made 5 stock trades in my life. The first 3 were unbelievably lucky. The 4th was horrific; the 5th wasn't bad in & of itself but still lost a lot of money.

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I picked my first stock when I turned 8. In order to interest us kids in finance, my dad told us to pick our favorite company and he'd buy a few shares for our birthday. I was a huge computer nerd so I chose Microsoft.

[On 8/25/1989 it traded for $58.75. Looking at the chart, it had traded in the low 60s earlier that spring and was down from a $70 peak the previous summer.]

I didn't interact with the stock market any more for about a decade. The summer before college, I decided I wanted to build the badass gaming rig my parents had never allowed, so I sold some of my old MSFT position.

[I don't remember the date, but I recall thinking it was cool that the ticker was 3 digits. Looking at the chart, MSFT peaked just over $100 for a few days in July. It was in the 70s much of June and plummetted back to the 80s by August.]

That fall, my freshman year, the dotcom craziness was in full swing. I didn't follow the stock market, but I was a regular on the Anandtech hot deals forum. One typical hot deal was a free $100 for opening an eTrade account. I'd just turned 18 so I had what remained of the MSFT transferred in. By the end of the semester, I was sick of packing my dorm full of absurdly cheap crap from ValueAmerica et al, plus I was going to study abroad in the spring, so as soon as I got home from school I sold off the rest of my MSFT position to buy a Eurail pass and have some leftover travel money.

[I don't remember the date, but classes ended 12/17/99, when MSFT closed at $116.62. Its all-time high would turn out to be $118.75. A little over 5 years later, it's trading around half that figure when adjusted for splits/divs.]

I don't remember what proportion of MSFT was sold at each time, but they amount to about the same return. Cost basis $0.36->$42.94 over 10 years (8/89 thru 7/99) is 119% average per year or 61.3% annualized; cost basis $0.36->$50.31 over 10.5 years (thru 12/99) is 60.1% annualized. I should've stopped there and gone down as the best stockpicker in history to only make a few thousand bucks.

A year or two later, I don't remember when, I decided to invest what remained in that eTrade account into INTC. This time around I actually was looking at price charts and industry reports, which no doubt jinxed my previously uncanny timing. I remember seeing it had dropped from the high 50s to $32 over the last couple months. Meanwhile Athlons & Coppermines were leapfrogging their way to a GHz, and fanboys like me were pumped up on both sides of the debate; surely things were looking up in the CPU industry? Turns out the tech selloff had merely just begun -- after buying, the stock promptly lost another half of its value.

I gave up stockpicking and ignored the market for a few years. Intel eventually creeped back up. I sold it around $27, posting a much more respectable loss than all the folks who bailed on tech stocks (or equities entirely) in 2001-2002. Decent trade, right? Wrong. I only sold to get away from eTrade, which during those years had charged me several hundred bucks in previously undisclosed fees∞, basically wiping out my whole "portfolio" if you could call it that.

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That was a year ago. Since then, I'm way into the black on the "fees paid to vs. rebates earned from financial companies" balance sheet. Kinda silly to relish in this tiny triumph over The Man after the eTrade fiasco, but still noteworthy: when I later studied finance rigorously, one important lesson was that controlling costs is among the most powerful factors in predicting a portfolio's success. I've also only made one stock bet since...appears I'm losing pretty badly ATM∞ but the stakes aren't very high∞ either ;)

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