This thread is great reading!
Here's my rather lengthy story:
I started investing way back in '88 or '89. Even before this I had worked at an investment management firm (minimum account size was $1 million) as a file clerk/coffee maker/gofer. I would file all manners of research reports, annual reports, advisories, etc. Of course, I'd be reading these as I filed them. They seemed very interesting, and sometimes I would check the newspaper a few months after I had read a stock recommendation, find out that that stock had went up and wished I had bought. But investing was very foreign to me and I knew nothing about how to buy a stock or even how to open an account at a broker, so I didn't do anything. Finally I saw an IPO announcement in the paper for Broderbund, a PC games maker. I thought, "Hey, I know Broderbund. I should buy some of their shares!" By that time I had heard about Charles Schwab and called them up to open an account. They sent me their new account form and I filled it out and mailed it off with a check for $5K. At the time, Broderbund had just opened and its price was around $15. By the time my account was opened it had shot up to $24. I was very innocent back then and called them up to ask, "Hey! I saw it at $15 when I first called to open an account. Can I still get it at that price?!" Thankfully, they didn't laugh at me and just gently told me no, the current price is $24. I was slightly peeved and asked them what was the fastest way I could've opened an account, and they said I could've went to their offices with a check and bought the stock right there. Well, shucks!
So I bit the bullet and bought $4K of Broderbund at $24 (I'd never heard of risk management then and for the next 10 years). Commissions back then were based on dollar amount, not shares, so I probably paid over a hundred bucks for that trade. After a couple of weeks or so, I sold all (never heard of scaling out either) at $28 and thought that was fun. Of course, it kept going up and I regretted selling, but I had my first profits.
For the next 5 years, I probably broke even on all of my trades. I invested/traded on tips from my coworkers and boss and followed the Motley Fool for a lot of my trades, although with the latter I seemed to always pass up the winners and pick the losers. But it was with the Fool's help that I played out a rags to riches to rags story...
One of the Fool's picks was good ol' Iomega, the Zip drive maker. I'm sure some of you remember the Iomega rollercoaster of '95-'96. The Fool picked it for their portfolio when it was at about $17 prepresplit (they've had maybe 3 splits). I mulled it over for a few days and finally jumped in at $22 with 1000 shares. As IOMG kept going up, I bought more using margin. I even bought some for my IRA. The Fool's IOMG message boards filled up with 200-300 messages per day, and of course I read them all. Sure, there were negative messages about bad Zip drives, CD-Rs being cheaper and faster, manias, etc., but I conveniently tuned them out because I absolutely -loved- Iomega! They were going to take over the world and nothing was going to stop them! I eventually ended up with 10K shares after a split or 2. The crowning glory was the day IOMG shot up 10 points on news. I had made $100K in a single day! It was absolutely mind-blowing! But alas, as I know now, that was very near the blowoff top.
A few days later, IOMG hit its all-time high of about $56. I was sitting on about $560K! That would've set me up good for a long time. Of course, greed got the best of me: I wanted to go for the million. As IOMG started coming down, I held on. One of the Fool's mantras was buy and hold for the long term. Sell only when the fundamentals change. I was completely brainwashed by this. I also reasoned that if the Fool didn't sell IOMG, I wasn't going to either. They said IOMG was good and I totally believed them. They weren't going to let me down.
As IOMG approached $40, a friend suggested that maybe I should sell some. I was totally pissed and strongly refused; couldn't he see that I was looking to the future, when IOMG would dominate portable storage? No way was I going to sell. I was going to fully participate in IOMG's future glory.
Soon the margin calls started coming. On the first few calls, I shoved in more money, but I finally realized that I couldn't keep doing that, so I had to sell some. It was very painful, but I still believed in the future and knew that IOMG would come back. I was on pins and needles every day, constantly checking stock prices. I calculated the exact price where a margin call would come and prayed that IOMG's price wouldn't fall below it.
Well fall below it did, and when the Schwab guy called and said I had to sell such and such number of shares before the end of the day, I did some quick calculations and only sold half because I believed that's all I needed to sell to maintain margin. The guy called back 2 minutes before the close and asked me why I didn't sell the correct amount. I tried to reason with him but he wouldn't have any of it and quickly sold the other half using his terminal. I felt helpless as the order went through.
As IOMG fell lower and lower, I still felt it had a chance as long as I could hold some shares. But eventually I had to dump it all. Immediately after that, the full weight of what I had done and what a fool I had been came crashing down on me like a ton of stock certificates. I was totally devastated. I was all set for life (at the age of 30) and I threw it all away because of greed and hope. As I write this, I can still clearly remember what happened next. My heart seemed to seize up as if I was in shock or in a permanently frightened state. My heart rate and breathing seemed to permanently speed up. I had a very hard time falling asleep, and when I woke up my heart would instantly seize up again. This lasted for 3 solid days! It really felt like the end of the world.
After that most awful of experiences, I took a 2-year hiatus from investing and trading. I couldn't look at stocks anymore; they scared the hell out of me.
In '98 I converted my small IRA into a Roth and started looking around. This Internet thing was getting very interesting, but I was scared to buy Internet stocks because they always seemed to be so high. The Motley Fool had bought AMZN in '97, but I had read reports that they wouldn't be profitable until 2000 (hmmm...and they were still wrong!), so I thought I'd be crazy to buy that. But I finally broke down and on the backs of AOL, ELNK, INKT and others I boosted my IRA by 500%.
By April '99 I had discovered daytrading. I don't remember how I learned about it, but I started with a $10K account at Datek and one of the free daytrading chat rooms. I had watched the room for awhile and noticed that the room leader called some really nice trades, so after awhile I plunged in; it looked so easy. After a week of trying to follow the leader, I was down $2K. I was always trying to chase his calls and usually ended up buying the tops and selling the bottoms. I figured out that daytrading wasn't as easy as it looked and proceeded to trade more carefully with smaller shares. Through the summer my account hovered around $15K or so. I wasn't losing, but I wasn't getting anywhere either.
Gee, this post is long...
In Fall '99 I discovered Pristine.com and read about the 30 minute Gap Play Long - if a stock gaps up more than 50 cents, buy over the 30 minute high with a stop under the low of the day. There was a Gap Play Short also, but I was scared of shorting and ignored that. I thought the play sounded reasonable and adopted it. I finally had a method, however simple it was. Previously, I was just following chatrooms without knowing the reasoning behind calls. I used my IRA to trade this method because I thought of the money in it as not real, since I can't touch it until I'm 59 1/2. It was easier to use this "unreal" money instead of the "real" money in my regular account.
With this new method and careful selection of chatroom calls (I remember LNCR being called at about $1 right at the end of the day and took a flyer on it - if you can call 1000 shares a flyer. I sold it at $6 the next morning! That was so sweet!), almost doubled my IRA by the end of '99. The gap breakouts worked really well most of the time. I wasn't setting stop points back then, but I would just jump out if I sensed a stock was going the wrong way. I was using TD Waterhouse as my broker. I had heard about direct access, but I had also read on Silicon Investor that market makers usually leave their Auto-Ex switched on in most stocks. I tested this out with Waterhouse and found lightning fills most of the time. I couldn't understand why anyone would use direct access when I could get fills like I was getting at Waterhouse. Why sell into the buying and guess the top? I would observe when the top was forming and send in a market order (horrors!) and would get out in a flash right at the top, even when everyone else was panicking and hitting the bids! That was just heaven!
Of course, good things don't last forever, and one day I bought a stock and wanted to sell it when I saw it was moving down. But I couldn't find it in my Positions list. I kept refreshing the page but the stock didn't show up. It finally showed up after a few minutes and I sold it for a bigger loss than I had intended. I called Waterhouse and asked them what had happened. They said they had just put in a policy that restricted people from selling their stocks until after they've held it for 2 minutes. They didn't want daytraders flooding their systems with orders. Outrageous! I knew I had to find a new broker.
With my experience with the Gap Play, I decided to open a regular account at Preferred Trade at the beginning of 2000 with $14K. Preferred had a $15 Auto-Trade (that only used SNET and INCA) and a $7.95 payment-for-order-flow trade. I expected the $7.95 trade to be lightning fast, just like at Waterhouse. This didn't happen in the first couple of days, but I lucked out after that because Preferred had just signed an Auto-Ex deal with NITE. I took advantage and turned my $14K into about $52K in about 3 months. I was averaging about $1200 per day by the second month, with my best day over $4K. I had a winning streak of 38 days in a row at one point. I also had a stretch of 30 winning trades in a row. The Gap Play was working beautifully during the go-go Internet days. I was a nervous trader (still so now) and would sell at the first signs of weakness, but I'd still sometimes get 4-point breakouts with hardly any selling in sight. I would also look for rapidly falling stocks on heavy volume and would buy them at the first signs of strength. Those picks worked very well back then, too.
Soon, NITE found out that Preferred had some good traders and was losing good money to them, so they pulled the plug on the Auto-Ex. I found that out when one day I was sitting on a $3800 day and a stock that I had already pulled good money from started falling. My mouth salivated at the thought of a $5K day. I bought a false bottom and tried to sell it when the bottom didn't hold. But I wouldn't get filled until it fell 6 points, with me screaming at the screen all the way down. After a week or two of subterfuge from Preferred about why the Auto-Ex didn't work anymore, I saw them at a daytrading conference and they admitted that NITE had cancelled the deal. I tried out their Auto-Trade for awhile after that, but it was very slow. Time for another broker!
In May 2000 I went half-time on my programming job so that I could trade the markets full-time (I'm on the West Coast). This was ill-advised because I was just learning direct access using RealTick at MB Trading, but it seemed like I was missing a lot of good trades by only trading the first 1 1/2 hours, so I went for it. With the Gap Play not working well anymore, my frustrations with direct access and RealTick (no more instant fills at the inside) and pressure from having to at least replace half of my income, I got my head handed to me after 2 months. The loss wasn't that bad ($5K), but it was humbling after my previous success. I traded small (100 to 200 shares) while learning RealTick, so the huge commissions ($50 round trips) assured that I wouldn't get anywhere. I begged (well, not really) for my full-time position back and got it in July. Next broker?
I went with Tradescape next mostly because of the low commissions and ok software. I started making money again with a pay chatroom (I'm still with them now), but Tradescape would always be only semi-reliable. It was frustrating, but I could always call them to get out of a trade fast if the software failed, so that was good.
Today I'm with Hold Brothers, and they seem to be the best broker to date, notwithstanding the instant executions from Preferred and Waterhouse. The pay chatroom calls stocks in up- or downtrends that have pulled back for 3 to 5 days, intraday flags, breakouts, stocks that have downside expansion bars to support, etc. They call the same types of plays over and over, with reasonable stops, so I understand the setups well. They espouse risk management, position sizing and small numbers of trades. They do fairly well every day; I just have to work on my emotions and psychology. I tend to jump out of plays before the stop hits because I don't really want to lose the entire stop (and watch them reverse without ever stopping out) and jump out of winners too early because I get very nervous if I sit on profits. I pick my own plays sometimes but I seem to trust them less than chatroom calls, so I mess them up. For example, today I bought RSAS (which gapped down on bad news) over it's 5 minute high, but I didn't really have a defined stop (I thought the low of the day was too far away), so when it reversed immediately I panicked out for a 0.18 loss. Of course, it went back up immediately and eventually busted loose for almost 2.50 as I stared at another failure. I've read "Trading in the Zone" by Mark Douglas and am trying to put his teachings to practice, but I still find it very hard to control my emotions.
If anyone's read this far, thanks and congratulations!

It was fun writing it and made me reflect on my entire trading career. I feel like I'm on the cusp of breaking out to new highs as a trader, as long as I can control those emotions. Good trading to you all!