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In 1987 or thereabouts, I had $1,000 and a dream of investing. I asked a friend, "Hey, why don't we put our money together and buy some Apple." I had been watching and reading, it was at a 52 week low, but everything seemed to point to it getting its act together, and my gut said invest in it. I let him talk me into some silver mine somewhere and of course we lost it all. Not a penny returned.

And that was only the first mistake.

The second big mistake was when I didn't trust my gut (see a trend?) and did it using borrowed money. I started writing options (iron condors) on S&P 500 futures with $150,000 HELOC. Was making about 30% annualized, but was becoming concerned with the signs in the market. My wife and I said there is no way our house could be worth X amount of money. I read an article from someone I respected that talked about how GoldmanSachs' stock had been a pretty good bellwether of negative things to come and it was pointing towards a correction. Articles abounded about China putting false bottoms under new stock offerings, etc. So being the wise person I was, in the Spring of 2008 I set a target and I said, "I will not set any trades that expire after the Beijing Olympics." Of course I got complacent, blew past my goal (which I didn't write down), and the rest is history. I lost all my profits and $100,000 of the HELOC.

I took the remaining $50,000, bought into MFPro, and got real about my investing talents.

Do I get a prize for being the most foolish (and not in the good sense)?
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