Ian Landsman is right on in 4 Rules for the Practical Entrepreneur. This is a must-read for anyone considering making the jump to being a software product freelancer. Falling into Ian’s “visionary” category is fine as long as you know what you’re getting into.
With Zesty News, I broke one of Ian’s rules: it’s a consumer product. Kinda. It appeals to both business and consumer users, so the question then becomes one of marketing and how you draw the business users in. I’ll be writing more about Zesty News soon (believe it or not).
With TurboGears, it’s hard to even draw parallels with the kind of thing you just “go off and start”. I’m forging off into some new territory (for me) and it’ll be interesting to see where I end up.