re: What's the worst investment you've ever made.....

autographed Christopher Cross 8x10 print

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i have one bad investment: thesportsjury.com

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Holy shite i forgot about that.

Anacott steel

I worked at United Companies during the late 90's and although the stock was falling I liked the fact that senior management gave regular updates to the rank and file that seemed pretty honest about the likely troubles ahead.

It turned out they had indeed been honest - to this day I have never seen an executive team that leveled with the rank and file as much. The problem was that they were very right that times were tough and so I lost over 95% on my investment when I bought at $5/share.

bought freddie and fannie after the crash pretty low, ran up over 100%, came back after lunch to see I had lost 40%. No longer mess w/ pennies and bankruptcies.

Wife's business. I let her nag me into it. Her first one lost big, her one now is above water, but barely and she will probably just pay the loan off and wash her hands in a few years.

Too much time and money in a multi-level. Sometimes it was fun, and I learned a lot... but not THAT much. Foolishness.

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What's a multi level?

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Multi-Level Marketing. That horse shite where you get people to sign up under you and get a percentage of their sales, etc...

You usually pay to buy into a system where you get discounts on purchases, then sell memberships to people and "build your empire". I think Amway global is the biggest one.

MLM Wiki

Too many to count and painful to revisit. Here's a couple of bone-headed moves:

1. I was watching Enron in 1999 and 2000 and almost shorted it, thinking it was way over-valued. Then it starting falling in 2001. Then 9/11 hit and the market collapsed and closed for a few days. The first day the market opened, I bought a few shares of Enron and, as it fell, I bought some more. Was at my parents house the day after Thanksgiving 2001 and the stock went below $1. Didn't sell any of it.
2. I allocate a small amount of total portfolio into high-risk ventures. I invested in a company that was going to use technology to reduce falls and improve communication for nursing home residents. Sounded like a good idea and the guy running it seemed legit. "Poof" about 2-3 years later.

OK, enough pain for now.... ***







*** I did make out on a few oil refining LEAPS that I recently bought. Calls on two different companies and popped like 2-3 times my investment in a matter of a month or two. There, I feel better.

My first wife.

I decided I was going to trade options. Dumbest decision ever. Completely busted out twice. It wasn't just the options though, I had no clue how to manage risk and recognize good times to make entries and exits. A good learning experience though and a learned many important lessons on not all that much money.