How can it be “obstruction of justice” if you do it before you are served with a subpoena?
Catch 22.
The statute involved (18 USC 1519) does not require that you have been served with a subpoena. It does require that you destroy information "with the intent to impede, obstruct or influence" a federal investigation. According to the article, he has already pleaded guilty, so there is probably more to this case than the headline implies.
If I have incriminating paper documents and destroy them before I’m am served, I’ll go to jail. Why should digital documents be any different?