I love these stories. I got my start around 1998 when the web was coming into full force which was only a decade after this and very different. Things were changing quickly in that era.
The closest I've had to this was working at a company that had been around for close to thirty years and had kept many of the original developers (they'd taken the product from a terminal interface to the web, from cobol to c#) and had many stories like the one in the original post.