I think selling is the hardest part of investing. Buying is, of course, critical to generating strong investment performance. Figuring out what to buy and when to buy it is what most people think of when they think of investing. But your returns will have as much to do with selling as buying. And buying is a fairly rational decision. Selling tends to be emotional. And that is why selling is the hardest part of investing.
In venture capital, thankfully, VCs don’t drive a lot of the sell decisions. I wrote about that back in 2009. Most sell decisions that really matter in a venture portfolio will be made by the founders and management of the portfolio company, including the timing of the public offering if that is where a company is headed.
But even so, I have struggled with the sell decisions, both personally and professionally, over the course of my career. I have held on way too long and watched a publicly traded stock literally go all the way to zero without selling it (ouch). And I have made the even worse decision of selling too soon and watching a stock go up three, four, five times from where I sold it.
So where I have landed on selling is to make it formulaic.
If we (USV) have to make a sell decision, we like to have a policy and stick to it. We like to distribute our public positions as soon as we can, for example. That’s a policy and we stick to it. If you look at the SEC forms we have filed as a firm over the years, you can see that is what we do. It is a formula. It doesn’t mean that it is the right decision in each instance, but it does mean that, if we stick to it, we will do the same thing every time and the law of averages will work things out. We also let the people we work with know that is our policy so they are not surprised by it. What is worse is to make each decision emotionally and get them all or most of them wrong.
Personally, I like to dollar cost average out of a stock (sell a position over time instead of all at once) and I also like to hold onto some of the position for the very long term (schmuck insurance). I have a formula for the disposition of public stocks I get via distribution from USV and the other VC funds we are invested in. We execute the formula time and time again. It takes the emotion out of the decision and it works better for us.
The thing I have learned about selling is that it is almost impossible to optimize the sell point. You need a crystal ball and you need to know something that others don’t know. That is either impossible or criminal. So I don’t try to optimize it. I try to make it formulaic and systematic. It works better for me and I think it may work better for you too.