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This is the most appropriate forum I can find for this post. Everything below is related to long term and retirement investing. I am simply going to post some of my thought process with my personal concerns an a comparison to a friends investing strategy that seems to be doing better than mine in the hopes I'll get some interesting feedback.

I've been investing for several years now trying to learn as I go, but following the fool picks for the last 2 years or so. I currently have 19 picks. 18 are fool picks, and I picked up FXI today because I wanted more Asia exposure without risking a pick on an individual stock. I had a bad experience with TOMO, but my CRTP is doing great, so I figured an index to go with them seemed reasonable. It seems to me that when I get to my next pick I'll be at 20 and that may be too many. Without a good reason to sell, is it best to continue to adding more picks or add more money to my existing picks that are doing well? Probably a balance of both. The fool may be doing well overall, but I seem to make the wrong choices and am up only ~5%.

A friend of mine who has mostly fool picks (and 1 share of GOOG) is up 20%. I got my GOOG at $250 and sold at $350, oops. We have many of the same picks. I am in a regular trading account. My friend is in an IRA. His theory is to make a gain, sell, and repick, and continue repeating that process since he does not have to pay taxes on the gains. He is Scottrade and pays $7 for each trade. So following his example he'd be selling CTRP right about now, or at least what he invested in it and "letting the profit ride", and picking a new pick with the original investment money. We both invest the same amount for our purchases relative to our other picks (I do at least $1000 a pick, he prefers $700/pick)

I'm just a little frustrated since he seems to be doing so much better with a slight tweak to the amount of time we hold our picks. I'm of the hold forever until I have a reason to sell, he sells when he's made a decent amount and re-picks. He can sell a little easier since he does not pay taxes, but still even if he was he'd be doing better than me.

A (potentially stupid thing to do) is using my margin ability which I have but have not used in years to buy something I think should do well, like 10K worth, watch it closely, hope to make some $, and sell if it seems like I made a mistake and eat a reasonably small loss ($500 / 5%). For example I was considering doing this with DLB and oops... big gainer today but that may have started me off on a dangerous investment strategy path.

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