According to the Jason Wikipedia article, Jason Kottke of kottke.org was the first to try to make a living from blogging through a PBS-like micropatrons approach where he had a 3 week “fund drive” which raised enough for him to blog for a year.
After a year he reflected on the experience in Oh, what a year. felixsalmon was not impressed.
This story, which was big news at the time, is old now, I know. Thanks to Matt for alerting me to it (back when it was news.)