Ask HN: I Need Career Advice from an Experienced VC or Entrepreneur
[I would, ahem, really prefer to post this under an alternate name, but HN has a bad habit of banning new users who submit. Either that, or "You're submitting too fast" after one post is a forum bug.]

Obviously, I would prefer that people not try to guess at my real identity, which I'm not going to disclose in a public space such as this.

I'm at a startup in New York that has, in my opinion, an excellent product that is near launch, but I think we might be in trouble. One of our co-founders had what appears to be a nervous breakdown last fall and he is now unreliable and essentially non-productive. He was responsible for about 40000 lines of code and a major component of our product. The architecture of his work is poor and documentation is nonexistent. (We had known about these problems for over a year; but a year ago, we had him in the game enough to maintain his crappy code, and his productivity made him enough of a net win that we put up with him.) The code is probably "totaled" in the sense that it'd ideally be best to part ways with him, throw out his code, and rewrite these pieces again. However, I don't think we have enough runway to do so, yet I'm equally nervous about launching on buggy, bad code that none of us understand.

At this point, most of my time and a substantial fraction of another key developer's time is dedicated to cleaning up the messes left by this other person, whose code is a recurrent source of negative surprises (he didn't follow his stated API, which was itself a complicated POS, very well). It's stressful and a bit scary, because it leads to what at least feels like very slow progress.

I obviously really, really want this product and this company to succeed. Even though it might make sense, from a purely selfish perspective, to just move on to Google or Wall Street, I have no desire to do so. I've spent almost 2 years on this startup and want desperately to see it succeed, and I believe we can. I owe my best effort to my co-founders, and really believe our product has the capability to be a technological home run.

I'm not necessarily looking for funding-- I want the right thing to happen, and if the right thing is for us to fail and for me to move on, so be it, but I don't think this is the case. What I'm looking for advice and mentoring, preferably from someone more experienced with startups than I am, on how to turn this situation into as much of a success as is possible.

I'll get into more detail on this situation in private. My email is someonebornin83 at gmail dot com.

A few questions:

1. How do I determine whether we will get to launch? I absolutely cannot consider any career moves until this point, because until we've launched I have nothing to show for my time. Sadly, launching seems to recede further into the distance with each new surprise that pops up.

2. Apparently, it doesn't look good to VCs to have been in existence for a long time without having launched, although the nature of our product is such that we can't launch it until we get it right. (This isn't some throwaway CRUD app; customers will actually rely on us having our house in order from Day 1.) How do we recover from the "damage" of having operated in "stealth mode" for so long, and of once having hired (and owing back pay to) someone who actually did a lot of damage?

3. In the unfortunate case where we do fail, what can I do to make sure that my time in the startup isn't counted at zero at my next job? I'm 27, and I'm sick of being a nobody. My motivation for being at the startup isn't getting rich; it's that I believe in the technology/vision and also want to be a contributing player in something, rather than some entry-level cog.

4. I would like to be a VC entrepreneur-in-residence by 33, unless sufficiently successful outside of the VC world. (There is no doubt that I have sufficient talent. I'm +2.5-3 sigma technical and +3-3.5 sigma "big picture".) Am I on the right path? It seems like startup experience is the best kind of experience one can get for such a role, but I don't really know because I'm completely ignorant about the industry.