One of my favorite techniques to buying and selling transactional assets (stocks being the prime example) is to dollar cost average on the way in and the way out.
I am doing this right now with Bitcoin. I want to buy enough bitcoin so I can make charitable gifts and political donations with it and generally transact in it as much as possible. I’m buying 1.5 bitcoin every week in my Coinbase account. I have a reminder in my calendar and I buy some every week at the same time (I bought some this morning). I’ll keep doing this until I feel like stopping. A lot depends on how much I spend I guess. But the point is I would not be comfortable going out and buying a bunch of bitcoin in one transaction. There’s too much market risk in doing that. By purchasing an asset in small amounts over a long period of time you average into your price and I like doing that.
When a stock is distributed to me from USV, I generally sell a little bit and then put some away permanently. And then I slowly sell the remaining amount over a long period of time, generally three to five years. I generally like to sell once a quarter at the same time. I like the week after the earnings reports, when all the information is in the market and the market has digested it. But that’s not the important thing. The important thing is to sell roughly the same amount in a regular rhythm.
The point of averaging in and averaging out is you never get the top or the bottom, but you get the average. And the average is just fine with me.
In some ways, building a position in an early stage venture fund is the same thing. We buy a bit at the seed stage, a bit more at the Srs A stage, a bit more at the Srs B stage, and so on and so forth. In some of our best companies, we have bought stock in five to ten rounds. Some of those rounds will turn out to have been bargains. Some will turn out to have been overpriced. But on average, if you get to invest in ten rounds, you will build a very good position at a very good price.
It goes back to optimizing versus satisficing. If you want to find the optimal entry price or the optimal exit price, you will drive yourself crazy. I prefer to find an acceptable price. And I think that averaging in and averaging out does that for you.