He and Chet Faliszek wrote the pioneering video game website Old Man Murray.

As a high-school student, Wolpaw wrote two games for the Atari 8-bit computers published as type-in programs in Antic magazine in 1983 and 1984.

[1] From 1997 to 2002, Wolpaw and Chet Faliszek wrote the video game-oriented website Old Man Murray.

In 2006, he won the Game Developers Choice Award for Best Writing for his story and dialogue contributions to Psychonauts.

Expecting his condition to require a departure from the company, he spoke with managing director Gabe Newell, who surprised him by offering an extended leave with pay.