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Old 01-09-2012, 04:42 PM   #41
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Old 01-09-2012, 05:05 PM   #42
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I gosh I have so many.
My friend's Turkish game company. This one cost me time also, turns out I am better playing games than designing them.
A local Hawaii company that started off making jammers for IED devices and ended up making heatsink for graphic cards,now dead and finally buried.
Recently I had the nerve to short Netflix at 250, because I was sure it was worth only 125. It went up and stuck with it, but the moment I had a modest profit 220 I bought it back. Now I would beat myself up if I sold at 125 even with the current stock price, but it is important when you buy or short a stock to have a target sell price.
Still these are risky investment which I knew in advance could turn out bad.

I think hands down my worse investment is my brilliant idea of taking out a home equity loan (at least it was from Pen Fed) at the end of 2007, and investing the money in those safe bank stock with dividend yield higher than the interest rate I was paying seemed brilliant in Jan 2008. Not nearly so smart a year later.
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Old 01-10-2012, 03:58 PM   #43
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I bought shares of SIII (S3, a video chip maker in the '90s) at about $4/share, only to see them triple in less than a year...so I sold half.

Ok, that was the SMART part.

Then, the shares dropped from about $12 to about $8. I saw this as a "sale", so I bought more. That was the DUMB part.

A year later those shares were worth pennies.

Overall I ended up about even.
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Old 01-10-2012, 04:20 PM   #44
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Recommendation by a trusted friend helped to override my common sense.
Also, they made me sign a form that I verified that I was a sophisticated investor.
I hope never to be sophisticasted again. $10k was taken as a complete tax loss 2 years later.
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Old 01-10-2012, 09:31 PM   #45
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We had a WCOM 401k, so that was our biggest loss, but the worst investment was a a managed futures account with these folks. The guy that runs this outfit is all over Fox-Business News. I got out of this one without a loss..........

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Old 01-10-2012, 10:32 PM   #46
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To get all philosophical, my worst investments (in $) were my best investments (in learning).

You gotta learn from your mistakes, and you gotta to learn to keep your mistakes manageable (diversify!). Better yet, keep your eyes/ears open and learn from other people's mistakes.

-ERD50
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Old 01-10-2012, 10:50 PM   #47
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To get all philosophical, my worst investments (in $) were my best investments (in learning).

You gotta learn from your mistakes, and you gotta to learn to keep your mistakes manageable (diversify!). Better yet, keep your eyes/ears open and learn from other people's mistakes.

-ERD50
Maybe we should start a thread 'how much did my investing education cost me?'

Not sure I want to calculate the NPV for that one.
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Old 01-12-2012, 02:20 PM   #48
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Lost 9k shorting QQQ when the Nasdaq was on tear from 4k to 4500. Of couse when it peaked at 5k a month later and imploded I was OUT of the short position.

"If you can't hang with the big dogs ... stay under the porch."
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Old 01-12-2012, 03:10 PM   #49
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Getting into day trading back in my college days. Using the LightSpeed platform which used 4x leverage when it used to be legal (maybe it still is). Lost about $6K in a matter of a couple trades. Made myself sick.

Never went back, following the long road to FIRE. Used to honestly think I would pull in $20K/month back then with my awesome trading platform. What a stupid mistake.
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Old 01-12-2012, 03:18 PM   #50
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WINR. I let a $600K unrealized gain dwindle to a worthless security.
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Old 01-12-2012, 03:38 PM   #51
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Bought this turd during the dot.com bubble. Went all in. Rode it to pennies. Couldn't sell my shares, price was dropping faster than I could get out. Completely wiped out at the age of 23. About $50k loss and hard lesson learned. Now I'm much more diversified and conservative.

Hopefully nobody else on this board knows or was in this POS stock.
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Old 01-12-2012, 04:12 PM   #52
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WINR. I let a $600K unrealized gain dwindle to a worthless security.
Okay, now I feel as if I can finally come clean. This all happened back in the early 80's. Had a "friend" who was selling all kinds of financial "product" from antiquity stores to firmware development with 3X write-offs to receivables financing and solar water heater leasing.

By the time the IRS got finished with us (and, of course, total losses and some outright fraud with some of the investments). I'm guessing that, in todays dollars, we threw away $250K. In the situation where investors were defrauded, my "friend" had claimed his "due diligence" was so thorough that he "personally guaranteed" that the investment could not lose money. Of course, when it did, he didn't make good on the guarantee - go figure!

Lesson Learned - Do NOT invest in ANYTHING that YOU can't explain to your 8 year old.
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Old 01-12-2012, 04:29 PM   #53
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Okay, now I feel as if I can finally come clean. .
I'm glad I could help...
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Old 01-12-2012, 05:45 PM   #54
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I let a $600K unrealized gain dwindle to a worthless security.
Damn!

(I feel better now.)
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Old 01-12-2012, 06:07 PM   #55
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I let a $600K unrealized gain dwindle to a worthless security.
But you haven't lost anything till you sell!
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Old 01-12-2012, 06:41 PM   #56
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My 2 biggest financial mistakes were:

1- Buying a large chunk of ATT Wireless stock in 1999 on margin. My wife was working for ATT at the time and everyone was saying how this stock was going to be a "sure thing" with the way all those tech IPO's were skyrocketing in the late 90's. The stock never went much above the opening price and when the bubble burst I was forced to liquidate a bunch of my positions at the bottom of the market to make my margin call. The stock ended up in the toilet.

2- When the market tanked in 2008 but then quickly recovered, I got spooked by all the bad news and was convinced we were headed for a double dip, so I looked to find a good exit point, deciding to liquidate my portfolio once I got back close to even with what it was prior to the crash. When I hit the mark in late 2009, rumors were also flying around about Steve Jobs health, so not wanting to take any chances I liquidated a HUGE position that I had in AAPL which was trading at around 170. Shortly after I liquidated, Apple announced the release of the first iPad , and the rest is history. Today AAPL is trading at around 420. In the end this move cost me around a million dollars.
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Old 01-12-2012, 07:42 PM   #57
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Sometimes it is easy to put a dollar amount on the loss, sometimes not. Let me explain.

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Well, I have lost plenty in land deals, forfeited income in start-ups, tech stocks, companies that eventually went bankrupt. I have not added them all up (do I want to?), but none of mine were as much as the OP's condo in a single bad deal (assuming it was paid with cash). Man, that hurts.

One expensive lesson, or numerous little less expensive ones? I am happy with the latter, I think. That gives me more stories to tell.
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Like NW-Bound, I've had only small modest losses. ..
My biggest loss, which was the lost time in the failed startups, was substantial. I did not put my own money in the ventures (hey, I was not that big a fool), but as a founding member, contributed about 3 man-years. That number of hours was a conservative estimate and could be a lot higher, because when one was so busy, who was counting?

Compared to the alternative scenario where I did not quit megacorp job, do I count the loss as the gross income or the net after all taxes? Remember that it would be the net that I would have if I did not make that career move, not the gross. But then, there were the forfeited benefits, the 401k matching, etc...

But the above was my biggest loss, a 6-figure sum no matter how one looks at it. There were other losses that were a lot cleaner for accounting, such as $20K on a land deal in the late 80s, $10K on some stupid small-cap stocks in the early 90s.

But when it comes to my other losses when I became an active investor starting in 1999, it became fuzzy. Here are some examples. I had to install the defunct Microsoft Money program in order to look at my old portfolio file to pull out the following numbers, as sorted in order by that program.

AMD -$16,683
LU -$9,565
HLIT -$9,497
TER -$9,441
UYG $-9,057
CNXT $-8,499
MOS $-7,792
SCHW $-7,244
LVLT $-6,983
AAUK $-4,639
IRF $-4,528
VGK $-4,478
etc...

I shall stop now. :-) See what I said in another post about how diversified I have been. Still, these losses add up to a 6-figure sum, you say...

The point I will make now is that these losses were canceled out by my gains. Counting again from large to small, I see

USD $16,211
POT $14,586
WFR $11,381
APA $11,038
OIH $8,025
TRA $6,702
BBY $6,542
HUM $6,458
TXU $6,448
NE $6,118
DRYS $5,807
etc...

The above were all realized gains and losses, incurred from 1998 up to when the Microsoft Money program went defunct a couple of years ago.

Now, I held individual stocks, so I could tell how much I gained or lost for each position. If you own these stocks inside an MF, or inside an index, how would you know?

Quote:
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WINR. I let a $600K unrealized gain dwindle to a worthless security.
That was an unrealized gain, so your actual loss was only the stock basis. Still, that "lost opportunity" really hurt!

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My 2 biggest financial mistakes were:

1- Buying a large chunk of ATT Wireless stock in 1999 on margin. My wife was working for ATT at the time and everyone was saying how this stock was going to be a "sure thing" with the way all those tech IPO's were skyrocketing in the late 90's. The stock never went much above the opening price and when the bubble burst I was forced to liquidate a bunch of my positions at the bottom of the market to make my margin call. The stock ended up in the toilet.

2- When the market tanked in 2008 but then quickly recovered, I got spooked by all the bad news and was convinced we were headed for a double dip, so I looked to find a good exit point, deciding to liquidate my portfolio once I got back close to even with what it was prior to the crash. When I hit the mark in late 2009, rumors were also flying around about Steve Jobs health, so not wanting to take any chances I liquidated a HUGE position that I had in AAPL which was trading at around 170. Shortly after I liquidated, Apple announced the release of the first iPad , and the rest is history. Today AAPL is trading at around 420. In the end this move cost me around a million dollars.
I actually remember your post announcing going to cash, and then recently your decision to buy back AAPL too. I wish you well.
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Old 01-12-2012, 08:04 PM   #58
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My 2 biggest financial mistakes were:

1- Buying a large chunk of ATT Wireless stock in 1999 on margin. My wife was working for ATT at the time and everyone was saying how this stock was going to be a "sure thing" with the way all those tech IPO's were skyrocketing in the late 90's. The stock never went much above the opening price and when the bubble burst I was forced to liquidate a bunch of my positions at the bottom of the market to make my margin call. The stock ended up in the toilet..........
.
Oh, Yeah...I forgot about this one.....nearly identical story, but we did not use margin. Many people did not realize that ATT Wireless was a "tracking stock", not a common stock representing equity in anything. The CEO brought the concept of a tracking stock with him when he came over from Hughes (GM Class H, which I owned) where it was quite successful.
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Old 01-13-2012, 12:35 AM   #59
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My worst investment was buying a global equity fund to balance out an asset allocation this year. All that asset allocation stuff sounded so logical and safe.
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Old 01-13-2012, 01:55 PM   #60
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......In the end this move cost me around a million dollars.
Ouch. Shoulda , coulda , woulda.

Look at they bright side, you avoided $150k in capital gains tax.
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