This was the question raised in the StartupNation.com community forum recently. It turns out to be a really good question because that forum topic has risen to be one of the most popular in the entire community.
It seems that the answer to the question is that bragging is always a good thing when done in the proper context and with the proper audience. Bragging can make you feel better & inspire you. Everybody loves to share good news, and most people love to hear it. So if you craft your brag in a way that encourages the listener, you can feel good about it and so can everyone else.
When starting & growing your own business, you often need a nice shot in the arm and sharing good stuff, even if it’s small stuff, can be just what the doctor ordered. So find yourself a receptive audience and start bragging.