The posters above who stated that pyramiding into strength is the real way to do it are right. A loss is a loss. Unrealized gains/losses are gains and losses. Every dime. Individual gains or losses on one trade are moot for many or most strategies. Getting it all back is the same as getting out and finding a better trade (less transaction costs, which with a good setup should not be much). That being said, do you go long into a new trade off of a chart that is falling like a knife? All else equal, no, so why would someone double into a trade that is not working? If he is sure that it is a good trade and can give himself a good reason why it is, then stay in, but take the capital that would have been a double down and go into another security that has a correlation that is close to 0 with the one you are in, for a good reason of course. Thats not going to guarantee anything, but will give him better results over time than his strategy, even if he has been doing OK lately. And even then, getting out of a loser is never a bad idea. The days when we have fat-tail events like a market up or down hundreds and hundreds of points, it is those people getting shaken out after they got used to what they thought was a viable strategy-many going bankrupt or lossing big. That is part of what I call the rubber-band effect-one of the reasons for support and resistance areas. Read stories about George Soros, how he never cared whether he was up or down on a trade, and you will see how someone like this acquired billions and bankrupted the Bank of England. The first thing I think of when I'm down is getting out, sometimes to a fault, because taking stops early is another way many traders fail too, but not as quick as what you were referring to! So to combat that I consider stops the same as targets (trailing stops-no target, per se). Small loss, small gain, big gain-not important-a viable strategy will allow enough big gains to combat financial and opportunity costs of options 1 and 2.
If I were you I would take my capital out and tell your friend you want to measure his success vs. yours. You seem pretty knowledgable about the key to successful trading, so after reasonable time, like a quarter, compare your % gain to his. Don't worry about day to day gains or losses-looks can be deceiving. Its just like fishing, if you can catch just one big fish now and then while not using too much bait then that is all you need to do. But if you keep throwing bait into a losing hole because a lot of small fish like to bite there or just nibble your bait away, then you might have a lot of fun but you're likely not to even pay for the bait.