Craig got his start as a web professional shortly before the fabled Netscape IPO in 1995. The company he was working for at the time was, sadly, not Netscape.
In 1996, Craig took a job at Wired Magazine's web-publishing arm, Hotwired. He worked on a variety of projects there, most notably serving as a writer and Multimedia Collection Manager of WebMonkey.com.
Craig left Hotwired in 1999 to briefly serve as Senior Producer for the Animation section of ShockWave.com. He left when he could no longer resist the siren-call of entrepreneurial life. The implosion of the '90's tech scene put a slight crimp in his plans, however.
Craig then ended up working as a Producer for the Sims, and SimCity websites for a few years. It was as awesome as it sounds.
In 2007, Craig founded Toonlet.com with Seth Ladygo, a website dedicated to creating simple tools that let anyone, regardless of their artistic ability, to start their own webcomic-blog.
toonlet is a primarily bootstrapped company, and Craig supplemented his (lack of) income by taking a short stint writing the part-names and space-phase mission text in the Spore videogame. That too, was as awesome as it sounds.