Uber-Soft Launches and Stealth Mode are two common practices that are usually big red flags of impending trouble.
To be clear, an Uber-Soft Launch is not a classic, small-scale launch where you release a decent version (maybe beta) of your product, but don't blast every PR trumpet you can find until you get a first round of feedback and some perf stats. There's nothing wrong with that; it borders on a best practice.
On the contrary, an Uber-Soft Launch is when the CEO or entrepreneur starts hedging about whether this launch is really the product or really the big launch he's been working toward and talking up. "We're going to just try this out and see what happens ... "
That statement is legit if it's intended as faux-modest understatement from a guy (or gal) who's clearly going for broke to make the product succeed. But if the firm or leader is really this wishy-washy and diffident about the launch, forget it. It's game over.
But then, in that case it doesn't matter because what the entrepreneur is really saying is that he doesn't expect to succeed so he's simply covering himself so he doesn't look silly after the failure. And that CYA attitude is one of the key things that indicates impending failure. It's a symptom of lack of conviction, a fear of failure that drives systematic bad decision-making.
Stealth Mode is a little less black-and-white, as there are a few cases where it may pay off. A few. Meaning not many. Luckily, Web 2.0 seems to involve far less "stealth mode" than Web 1.0 so it's less of a problem.
When might stealth mode be useful?
(1) A company has a specific physical or algorithmic invention (no, not Amazon one-click), and intends to patent it and to defend the patent vigorously (= has the massive cash to do so). Company wants to make sure it's documented and filed before anyone else files. If this is you, then you'd better be working toward the patent filing as fast as you can, no excuses. And get a good lawyer. If you're not ready and planning to defend, then stealth mode doesn't matter. Someone else can implement your technique if they want, and even patent it. You'll win or lose on execution and customer acquisition.
(2) A company's value is going to be based on a "network effect" play rather than a "hard-to-duplicate" play, and already has big the PR for the launch you lined up. In this case, since you know you're not "hard to duplicate," you don't want to spill the beans until you can fire off the giant PR cannons, at which point, you'll either grab a big enough chunk of network effect to sustain you, or else you'll drift. An example of this is Ning, which was in stealth mode for a long time. Marc Andreessen's celebrity and connections were the big PR blast, timed to match Ning's actual launch. But what if you're not Marc Andreessen or Kevin Rose and you're not going to make any headlines with your launch? Then you're not going to get a big "pop" when you come out of stealth mode, so really you're just:
Afraid of someone stealing your idea
But that's not a good reason for stealth. There are very few new ideas. If an entrepreneur thinks he or she has one, it almost certainly indicates insufficient research to find the people with the same or very similar idea before (and now), and consequently ignorance of why they failed (or might fail).
If this is you, get over yourself. Make it part of your "leadership agenda" to systematically find the previous incarnations of your idea -- or related ones. Analyze the heck out of them. Do better. Or be more popular. (Pick one or both).
But here's the twist, and if you're introspective then you saw this coming: you're not really afraid of someone stealing your idea, you're really
Afraid of someone not liking your idea
and you don't want to deal with that. You think that by waiting until you have perfect execution you will stun disbelievers with the beautiful product. That's just a delay/procrastination tactic. The underlying fear (of the product falling flat) will just make you want to delay and delay, making the product more and more "mature," so as to defeat nay-sayers.
Doesn't work. There will be nay-sayers. Embrace them. Love them. If you have money, make them into a focus group and pay them! Separate the whining pessimists from the ones with specific advice. Don't waste your time on the former, but realize that the latter are creating value in your company for free.
They are doing what your best product managers and designers should be doing -- finding and clearing roadblocks to adoption. Listen to them and verify what you think they're saying, by checking with other real people. Then you have a real bug list to work on, not getting the that drop-shadow AJAX doodad the right shade of pink.
As an entrepreneur, you're already drinking enough Kool-Aid by necessity; if you hide from naysayers, it just leads to a Kool-Aid overdose death-spiral.
I've been involved with companies that have committed both of these sins (and many more) so of course my perspective is warped by that. But don't take my word for it. Find the companies and entrepreneurs that you look up and want to learn from. Read their stories or go talk to them (being careful to filter out the Spiel and the 20/20 hindsight). Whatever you do, don't hide out convincing yourself you've invented cold fusion.