APT Exit Strategy, page-36

The answer is it depends on how long I hold the stock for. In the case of APT, it got very big very quickly, but I'm not comfortable having half my wealth in one stock simply to pay less tax. As is always the case, you tend to have losers that can offset some of the gains.

The example of APT is also somewhat of an anomaly given most investments don't 10x before 12 months. So it's usually a buy and hold for 12 months or more. Sometimes You get an opportunity to rebuy a stock where it's clear you could make a quick 20% or more, and in that case I have to wear the tax consequences.

This year I made the mistake of buy APX a bit too high, so I have significant loss I realized on that stock. I then rebought APX again some weeks later at a lower price.