Thoughts on When to Sell
One of the benefits of long term investing is that you have relatively fewer instances when you should be asking “should I sell?”

If you have to be asking yourself that on a weekly or monthly basis, you’re doing something wrong. (Or at least, that is an indicator that your strategy or behavior is not actually ‘long term investing).

When I buy a stock I usually ask myself if I can hold it for five plus years. This allows for the growth story of the company to play out. But there are downsides to this approach, (achieving anything in life is a story of tradeoffs), and one of them is that you can get complacent and hold a stock longer than you should.

Exhibit A: GoPro. I originally bought the stock back in late 2014 with the thesis that they would continue to be leaders in the action camera market and that the possibility of forming a media platform could surprise investors. But by late 2015 it became clear that “action camera” really just meant, “small, durable camera” which anyone could make. And media platform? It was clear that GoPro didn’t have the capitalization like Netflix or Amazon to produce the premium original content consistently to survive as a media company.

So when do you sell? In the case of GoPro, with hindsight being 20/20, mid 2015 would have been the right time. But selling at the exact right time is much like timing a market top or bottom- it’s virtually impossible to do. So what do you do when you dont know the future? As a long term investor I told myself to stay the course. What happened?

I lost 90% of my investment.

You might be surprised to hear I am glad I held onto my shares to this very day.

Does GoPro have some new growth prospects ahead of it? As it turns out, the reason I’m happy I still have GoPro shares has very little to do with GoPro, and much more to do with my own investing behavior. But you’ll have to wait until tomorrow’s memo for a full explanation. For now I’ll leave you with this- when you’re thinking of selling, the first thing you should do is take a break from the computer. Put your phone down, go spend some time with friends and family. Put those thoughts of selling on hold until tomorrow- where we can pick them right back up. See you tomorrow; same time, same place.
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