Everyone seems to write one of these, but I'd like to offer a unique thought I haven't seen elsewhere. For all three of you who read my blog regularly, you might've realized that I left my two cofounders at Hoodle, Dan and Jack, to restart my own company, Muxable.
I'll spare you the details in common with every other retrospective but a question that's stuck in my mind is when did I know?
I think this happens in all relationships. There's a tipping point after which I've given up. After which I don't believe the relationship will work. After which any effort to rebuild the relationship will be half-hearted because deep down I know it won't pan out. In many cases, a new, different relationship will come in, but the old one has passed the tipping point and generally can't be saved.
Good cofounders never pass that point, otherwise inevitably the working relationship, well, doesn't work.
So when did I know? The strongest signal was when we discussed features and an argument against my proposal was that people aren't like me and therefore don't value the same featureset.
Funnily, it's not the correctness of the argument that mattered. People are unique and maybe I am more unique than others. But I fundamentally believe that I should solve my own problem and like-minded people will follow. If I'm not solving my own problem, I'm competing against people who are solving the problem with more information, more experience, and ultimately more relevance. It's a losing battle and I can't do as good of a job as when I solve my own problem.
So a statement like "people aren't like you" to me suggests that it's not the target customer that I'm different from, it's my cofounders.
And that's when I knew it wouldn't work out.