The discussion over at EnWorld about the OSR dying (yet again) did get me to indulge in a bit of self-reflection as to why I turned from a hobbyist blogger into a professional publisher. I can assure you, it wasn't for the money or the fame!
Indeed, at first, I was offering stuff here for free. I did the Castle of the Mad Archmage as a series of free installments, and everyone really seemed to like it. But after a while, it became more about wanting to make the thing better. Nicer. With art. And then I started on my Adventures Dark and Deep project, and it seemed a damn shame to just use free clipart from the web. I certainly couldn't use the original art from the DMG or the Monster Manual, for legal reasons.
For me, that's why I publish what I write, and charge for it. I want to be able to make what I write look nice, and that means hiring artists, and editors, and (sometimes) consultants. A free pdf loaded with typos and with clipart from Google would work from a utilitarian perspective, but (especially in the case of Adventures Dark and Deep) the presentation was part of the project, and I wanted it to be as good as I could make it.
After I started doing things this way, I started to feel a bit of a responsibility towards the artists, editors, and cartographers, and such that I was using to help me realize those visions. I really do take a point of pride in supporting the artists that I use. Without me, there would literally be hundreds of pieces of fantasy art that would never have existed, and the artists themselves would be out thousands of dollars, collectively. There's something of a responsibility there, and there's definitely a feeling of "I'm helping to support artists" that comes with doing things the way I'm doing them.
Are there profits? Absolutely. Do most go back into new projects? Also yes, as witnessed by the fact that I've been able to self-fund my last three big projects, and several smaller ones, without having to dip back into the Kickstarter well. And I've been able to make a mortgage payment or two because of the games, but hardly enough to turn into a full time job. Do I wish something I write takes off like Cards Against Humanity? You betcha! Do I think it's likely? Not particularly.
But to be honest, I still consider myself to be a hobbyist. The OGL and POD make my life much easier than it would have been back in the late 1980's, but essentially in my mind I'm still just a part of the DIY ethos that is such a huge part of the OSR. (Acronym quadruple score!) And in the process I'm able to support artists, and editors, and other folks who are also part of that relatively tight-knit community. I make a few bucks off my hobby, I get to see my visions brought to fruition, and people seem happy enough with my work to buy it and keep the cycle going.
And truth be told, I'm not sure what more one could ask from a hobby.