What you are missing: build the product first I wasn't missing that, though I definitely gave the impression that I had. My intention had always been to just

What you are missing: build the product first I wasn't missing that, though I definitely gave the impression that I had. My intention had always been to just sort of throw them both online, the ad-supported idea going first to prove to myself that I could make a website that a) didn't look absolutely god-awful, and b) wouldn't get hacked to pieces by every idiot script kiddie that came across it. I only have very limited experience with web anything, and really with programming in general (after college - community college - I ended up stuck in a COBOL job for three years, and it burned me out so badly that most days I just didn't want to code anything on my own time, so I've definitely rusted over in a lot of places), so I'm validating my skills first on a trial site before moving to the more "business-y" site. The second site was always intended to start free first, with money being a secondary concern to gaining an audience. If you're selling someone on advertising with you, they're going to want an audience before they really pay anything. Likewise, nobody wants to come to such a site if nobody is advertising anything. The solution, fairly clearly, was to give it away free to the advertisers at first saying all it would cost them was a bit of time to get things loaded into the system, then if the site became popular it would become a pay site as it came out of Beta. My purpose for this question wasn't so much to get everything in order right now, but rather to try to collect information so that if the time ever came I would be prepared to quickly transition to a proper business. I was rather hoping for external sources (books, Canadian-oriented guides/blogs/whatever), but anecdotes are definitely beneficial and appreciated as well. Another, though by no means less important, reason was to determine my liability. E.g. if someone writes a terrible set of directions on the first site, and some moron follows these instructions and dies, how liable would I be if I wasn't a proper business, let alone an incorporated one.