As a one-person ISV, what are the major challenges you faced? How did you overcome these challenges?
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closed as primarily opinion-based by MichaelT, Dan Pichelman, GlenH7, Bart van Ingen Schenau, gnat Sep 23 '14 at 9:23
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Lots of good points, but one more: many clients will regard the fact that there's only you as a risk.
With larger teams or organisations if anything happens to one person (they fall ill or whatever) then others on the team will tend to have the knowledge to cover them. Where it's just one person that sort of thing isn't possible.
This will particularly be true where there may be some on-going component to the work such as third line support. If you're away, or on another project, will they be confident that they're going to get the service they need.
Pierre already named some issues, here is another list:
You must assume all roles, including sales, marketing, finance, development, administrative, legal, and more importantly product development. To name a few.
This means that most of your time, you will eventually do something you dislike or you are not good at.
That's the major challenge.
If you can cope with that, I'm sure you will be successful.
One of the things that gets me is time it takes to type everything.
Honestly; it's not so much that these roles 'take time'; obviously they do. It's not even, as Pierre said, that I don't like them; I like doing these things. It's the fact that I'm sitting at my machine, with my IDE open, but I'm typing in Word, or the bug tracker, or something of that ilk when I have solutions to problems in my head trying to claw their way out.1
How do I get around it? I try to use tools and processes that can cut down on it as much as possible. Right now I'm giving FogBugz + Kiln another shot so that checkins can be tied to cases more easily. I try to keep things like use cases in FogBugz labelled as features, and I modify them there. I only copy them out into a word document when someone needs to see the document. Likewise for specific requirements. FogBugz also has some automated scheduling built in, which is nice (though I haven't really used that part of it).
There's other tools that can do these things as well, but I'm just telling you whave I've chosen.
1: I have an irrational fear that if I don't get my 'solutions' out of my head and into a compiler as soon as they come to me, then I'll forget them and they'll end up lost in my head forever.