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

bought a house in 2007... wasn't thinking of it as an investment but it turned out to be a terrible buy for me...

Not me, but I have parents who are very well off and they invested in cocoa...yes, the chocolate cocoa..like stock in a company...this was in the 90's...they did not get any ROI. I don't know what they were thinking.

Enron

I bought a lot of under armor and a little of netflix, both did quite well. Then I decided to sell all my UA and buy more Netflix. Lost 50%+ of the value.

I was gambling and it was a good lesson.

Before Katrina, I paid 7K down on a lease purchase before I got the signature from a cousin.

It was in Mandeville and the property value was 'reappraised' during my lease.

The lesson,

Don't do business with family.

i have one bad investment: thesportsjury.com

i didn't think it would be amazing or anything. but damn that place blew up (in the bad way, not in terms of popularity)

Worldcom. I really didn't make the investment thinking it was good. They bought a company in which I owned stock.

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.

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.