Still on the topic of portfolio management, I wanted to call out the website Portfolio Monkey which just went from alpha to beta. The alpha, uh, didn't work at all. The beta half works, and it's pretty cool. It is not very transparent, but it uses modern portfolio theory and extensions to calculate your portfolio's expected risk and return. (This part works, 90%). In principle, it also optimizes your holdings to get the best return/risk ratio, and even suggests efficient additions to your portfolio (these parts work 10%). Also, it does backtesting of a sort. If you had held this portfolio for the past x months, how would you have done vs. the S&P500 or whatever.
Their analysis of my portfolio is 4 and a half bananas, comparable to George Soros. They have a higher idea of what the market will return I think. They see me earning 19% +/-23%. (vs. I see it at 11 +/- 17). So, this meets a lot of what I was looking for on question 2 (how am I probably going to do, starting now?).
Another bunch of incredibly neat visualizations for portfolio analytics can be found here. Load the java and do some of the demos. I haven't looked at it enough to know if it answers any useful questions really well. But it does make a lot of really cool graphics.
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