@John I'm very interested in WP use cases that are like personal applications. WP is so suitable because you get this self hosted backend that you have full control over. And that's how I use WP everyday already. I hope a real market can develop out of it (because it's what I want to be involved with myself).

I'd be really surprised however if something like a desktop editor actually makes a lot of money, even a modest amount would surprise me quite frankly. Is that the intent with Desk? Are their certain criteria you are aiming to hit to determine whether its something to continue after year 1 and 2? I imagine such a thing taking a long time to really grow to a level where it starts to give a return on investment.

I know pivoting is an important decision for startups, not all ideas are going to be winners, some solutions become apparent dead ends or a project simply runs its course, or an obstacle surfaces that isn't worth overcoming (maybe that played a role here?). Having said that, you only hear about the successful pivots, you never hear about the projects that could have grown if only a team had persevered, i.e. the could-have-beens. I think in WordPress especially quite a lot of projects owe their success to sticking around long enough for growth to happen. I'm not sure the same expectation of growth that you find with, say, a venture backed tech startup can be realistically placed on a WP centric product (except for perhaps the hosting company model).

Anyhow, I hope you blog your experiences for all to benefit from!