Here's a list of real winners..
Several fund companies offer short-selling index portfolios with fairly low minimum investments. Rydex offers two such funds—the Ursa, which shorts the S&P 500, and the Arktos, which bets against the NASDAQ 100. ProFunds offers Bear, UltraBear and UltraShort OTC portfolios, which seek to provide returns that are, respectively, the opposite of the S&P 500, twice the opposite of the S&P 500 and
twice the opposite of the NASDAQ 100. Finally, from Potomac Funds, comes the U.S./Short Fund, which attempts to earn the opposite of the S&P 500, and the Potomac OTC/Short Fund, which tries to perform inversely to the Nasdaq 100. If you want to stick to funds, though, then whatever you do, do not use the "Ultra" funds; if the market goes against you, they will lose $2 for every $1 you put in.
In my opinion, if you must short, use only a small portion of your portfolio, say a maximum of 10%. Set an absolute dollar limit on how much you are willing to lose, and get out if you lose one penny more. Better still, start by washing your face in ice-cold water or slapping yourself vigorously on both cheeks, anything that might get you to reconsider.
Another link in SI that I thought was funny. I'd love to see him in person so I could ask him how his short position was going.
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