Evan Williams has a very thought-provoking essay today called Knowing When To Hold ‘Em. The gist of the story? Many folks seem to have sold their web applications too soon. Certainly, the examples given make it look as though were Flickr, MySpace, and Blogger stocks, they were sold at the wrong time! Indeed, Flickr has ten times the page views as it did when it was sold to Yahoo!.

Now, Mr. Williams is not claiming that selling was necessarily a mistake, and just like with the stock market, hindsight is 20/20. And he brings up another interesting point in his article:

Would they have grown even more had they not been acquired? Who knows. But it’s not beyond the realm of possibility that these sites have been hindered after acquisition by a lack of flexibility or by having fewer resources to do what they needed to do than they would have otherwise, because they had to compete for them internally instead of buying them on the open market.

So hey, maybe it’s not a good idea to sell sometimes.