Recently Eric Burns had more then a little real life problems which caused to reconsider his whole position on merchandising and Websnark. The question is if you start worrying about making money from t-shirts and other stuff will your product be as good? Will trying to sell a product influence the direction and quality of the original product? For many web comic artists the answer is obvious as every artist is dying to make a living from doing something they love.
This is quite a long article but after having attended Connecticon I have to say it is a must read. It expresses many facts and insights completely foreign to your average person such as the transition from being a comic to being a business. You can get a tax right off for anything related to the product you produce, such as art supplies and traveling expenses to cons. We heard even better stories of artists expensing games because they had a gaming comic or their car because they slapped a logo on the side making the car an advertisement.
Most important tid bit though is what was the turning point that caused the transition: T-Shirts. 100% of the web comics artists said the turning point of making real money was selling t-shirts. It was not advertisements or books or toys, although those were nice. The minute you can afford to buy those pieces of cloth in bulk orders and then turn around and sell all of them you’re on your way. Just ask Eric about selling his minimum order in 12 hours instead of a week.