The Ideas
Way back in 1999, high-speed Internet connectivity, while not new, was just becoming affordable to small businesses and even upper middle-class homes. Using HTML to throw up a business card website was all the rage, but using a website for actual commerce was expensive, time-consuming and confusing at best for most business owners. Then there was the development-side of things: Tools like HotDog, Dreamweaver, Ipswitch FTP were just coming off 1st and 2nd revisions. Most coding was manual and Macromedia Flash was in its infancy.
Analog Cellular technology was just decent enough to allow 4.8k or so of data transfer rates; webhosting costs were coming down and consumer digital photography equipment could take decent enough images to post a 640x480 pixel photo in an HTML page without needing massive horsepower and 4 hrs of time to do it.
So, a plan was hatched. Rip apart the VW Beetle, buy some decals, connect the Dell laptop to a Logitech Quickcam, Toshiba digital camera, Nokia 5120 cell phone, have some sweet logo vests and postcards made, sketch a plan on a map and hit the freakin' road!
It just so happens to coincide with Lent of Y2K - how perfect for a recovering Catholic to spend Lent in the supposed new millenium - drive the country and see the sites.