As the editor of a controversial literary website, Gary Baum used to receive many strange emails, often from people who were conceptual email artists, and sometimes he didn’t know quite what to do with them. “I remember the first time Zadie Smith emailed me,” he told me when I visited him in California the month before his high school graduation. “I didn’t believe it was her. I was like, ‘Okay, bye.’ Finally she wrote me an email—she had a Hotmail account!—where she took all the people on the acknowledgments page of her book and explained how she knew every one of them. Then she was like, ‘Now do you believe me?’” Having established her credentials, Smith was able to inform Gary that the rumors he was trying to generate on his website, of her liaison with Dave Eggers, were not based in fact. “The ultimate literary hook-up,” is what Gary had called the alleged affair.

Zadie Smith was not the first person to find herself annoyed with Gary’s antics. In another time, the offended parties would likely have been limited to the principal of Calabasas High School, for whom Gary’s newspaper work was a constant thorn in the side, and possibly the local PTA. But in our technological age, a funny thing happened to Gary Baum: in addition to his duties as a young adult—editing the Calabasas Courier, filling out college applications, scrutinizing Dawson’s Creek—for two years he took the fight to New York literary culture. During that time he produced, on his website, a remarkable document about the rise to prominence of writer and editor Dave Eggers. While doing so he irritated a wide range of people—“I can’t believe,” one writer told me after being quoted on Gary’s site with a superfluous [sic] attached, “that he siced me!”—and made life less comfortable for the ostensible object of his affection. He also learned more than anyone ought to know about the way things work.

What follows touches upon many things—Eggers’s career, literary nepotism, digitized postmodernity, and the media tsunami in which Eggers himself became engulfed and whose abrasive spray Gary felt against his face. But it is above all the story of Gary’s education.