Hollinger developed the website Alleyoop in 1996, initially as a hobby and sounding board for his musings on the game.
During Alleyoop's early years, Hollinger experimented with offensive and defensive ratings (points created and allowed per 100 possessions) in much the same way as Oliver, as a means of quantifying a player's overall contribution to his team.
While the methods were hardly groundbreaking, Hollinger's writing style and incisive commentary caught the eye of such industry luminaries as the magazine Web and The Wall Street Journal.
Hollinger spent the next three years as the sports editor at OregonLive.com, developing an intimate understanding of the inner workings of the NBA, both as a game and a business.
After his stint in Portland, Hollinger was hired as the basketball editor at SI.com, Sports Illustrated's online sister site.
He left Sports Illustrated to write for ESPN.com in the summer of 2005, and his weekly columns were available through their "insider" subscription service.