This quote comes from a conversation I had with a friend. He grew up using it with friends and family to refer to any time one gets too confident or too big for their britches.
Basically he’s saying that while its obviously good to gain knowledge and knowhow on any given subject, it just seems to be human nature that the more we think we know, the more we tend to relax and start to coast on that overconfidence. If you, “stay stupid,” at least in your own mind, then you never think you know enough. You never give yourself the chance to rest and become fat, dumb and lazy, or too comfortable in your position. Smart people think they’ve got it made, but whether it’s in music or in business those who stay stupid have a keen sense that there is always more to learn, always more to accomplish.
Another brilliant quote from that same conversation is “confidence is the silent killer.” Confidence is something we all should seek to gain in whatever we do. It can actually land the deal or allow us to do things others would have thought impossible. Yet in the same context as, “stay stupid,” just as calories which give us the energy to accomplish all that we do in a day, can turn into fat if it stays still for too long, so confidence that isn’t stretched and exercised becomes comfort, silently clogging the arteries of our success.