patrick.net

Probably not buying Google pre-IPO when they offered up to 5k worth for 50 cents a share. Stayed away from it because it seemed like an echo the dot-com bust. Coulda retired on that one!

msilenus says

I was working at Infospace back when the dot com bubble was bursting,

I bought Infospace at something like $4 and change, and sold for $8 and change. This was what, late 90's? Definitely before the bust by a long shot. Doubled my money but I think I only had 1000 shares.

I don't have one trade that tanked, but what I *did* really screw up was the the whole dot-com thing. I was in the software business in the late 90's and was very contrarian about the dot-coms. I kept telling EVERYONE to sell their silly 'internet' stocks. I used to talk about the companies with a business plan "written on a cocktail napkin".

I was finally right but the problem was I didn't take my own advice. I had a lot of 'growth' mutual funds - I was young and pretty lazy/naive about what was actually *in* my mutual funds. Had I taken the time to look closely, I would have cashed them all out. Naturally they were full of these stocks I told people to sell.

I'm still recovering from that one.

Sybrib says

I think mine is when I shorted F in early 2008, held the short down to around 6 or something like that but then chickened out when it went back to around 8 early in the summer.

Then later in the year it bottomed around 2.

I bought F at $5, $3, and $1.74. I wish I had put every penny I owned in it. I sold at what, $9 and change. I wish I had held it longer but did ok.

Now ask me about my mutual funds (oh wait, I already posted that debacle).

American in Japan says

I was in a short ETF (SH for the past 6 months), but I sold 2 days ago (I should have waited just 2 days)!

You do realize that SH is not intended for long-term investments and that you weren't really shorting anything, right?

Yes I do. It simulates a short.

American in Japan says

Yes I do. It simulates a short.

Not if you hold it for 6 months.

It only simulates a short if you hold it short-term with relatively low volatility -- its returns are based on the *daily* change. Because of tracking error and volatility drag, it definitely does not simulate a short over the long term.

SH is one of the better ones in terms of these factors, but its tracking error and drag is greatly increased in times of high volatility, such as now. The tracking error and drag are still not as bad as the leveraged versions, however.

Inverse funds are definitely not the same as shorting and do not simulate shorting.

billy269 says

FAIRX (Fairholme Fund) with the way it is going right now. I have hopes it will rebound though.

Isn't Fairholme one of the biggest shareholders of BofA? If I remember correctly, FAIRX bought large amounts of all the banksters -- Shitty, Goldman, and Morgan Stanley, also Notorious AIG, and even things like CIT and certain property managers like Brookfield. Basically, everything that they thought was distressed and possibly oversold. I'm assuming their theory was "at least one of these companies has to do well, right?"

What made you buy them?

SIRI.

Not very glamorous I know, but back when Howard was in contract renegotiation and they were at 8-12 cents a share. I seriously thought about it...

$1000/0.12c = 83333 shares

Todays price of $1.72
83333 * 1.72 = $143,332.76

I am out of SH now.

Vicente,
don't worry about it. Not doing something is not really a bad investment move. Because it's not a move at all. Missed opportunity, of course. But that is a different question.
If we had to list our worst missed opportunities, the list would be so much longer.

For me, it'd start with my college days when I declined an offer from a Swedish coed on her way back home to Europe, to share a hotel room "to share expenses" near NYC airport during a flights layover. Wanted to perserve my small amount of cash for something else so I spent the night at a relative's house in the area.

I told my professor about it after I had returned home to California. He laughed out loud at me and told me something like, "you dummy, that's what your credit cards are for!"