Failure isn’t a possibility, its a certainty. But that’s a good thing, because the sooner you fail, the quicker you can succeed. So while the goal is never to ship crappy software, its better to have had the experience of shipping a less than ideal product than not.
I learned a ton about my users needs after launching the first iteration of Dovetail. The more users I talked to, the more I realized that the product wasn’t solving the problem we’d set out to solve. If I could give one piece of advice, its be transparent with your users, especially your early adopters. If you ship a buggy update, own it. If your app isn’t solving the right problem, discuss it.
Be real with your users, and they’ll be real with you.