For what it's worth, I recently talked to a founder who didn't send updates for the first year, then finally started sending them a few months ago. The founder's feedback was that sending updates turned out to be surprisingly useful. 1) Individual investors stopped asking for 1:1 updates, which were previously time consuming. 2) When the founder asked for help in an update, there were now many offers to help. 3) It was good to step back every month and look at the bigger picture.
Great article Sean! Amazing insight and really practical. I love articles like this that actually teach you something you can use instead of just some theories.