Jason Kottke started Kottke.org in 1998, making it one of the oldest, still maintained blogs on the web with over 26,000 posts spanning topics from art and technology to design, culture, and general knowledge. This is a peek behind the scenes of Jason's process, his philosophies, and general thoughts on the internet––where it’s been, and maybe where it’s going. We talked about what running the blog looks like now, how it’s changed over the years. The evolution of patronage models, and his current thoughts on them. We talked a bit about burn out and managing that tension between what you really want to do versus what may appear to be the path of success online. And about the increasingly challenging task of maintaining ownership over what you create online. We also compared and contrasted our experiences as an OG blogger versus an OG vlogger, and how terrible both of those words are.