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Seeing the immense value of Napster's brand, several employees had suggested selling logo shirts and other goods as an uncontroversial way to raise money and promote the service. They also had wanted to give away the gear to recognize hardworking volunteers, including the moderators of the Napster chat rooms. Richardson had been reluctant to approve the clothing plans because they got into the sticky area of profiting from the service prior to a settlement deal. She felt that any revenue taken in before the suit ended would be used against Napster in court, and she was right.

One Napster moderator, Tarek Loubani, a Chess.net veteran and a friend of Shawn's, asked Shawn if he could go ahead and make shirts on his own. Shawn told him to go for it. Loubani, then a college student in Canada, didn't want to make shirts with just the logo: He wanted something that would capture what he saw as the politics of the movement. He made a series with revolutionary themes, including one alluding to William Wallace, the Scottish rebel who inspired the movie Braveheart. Another adapted the slogan of the French Revolution: "Liberte, Fraternite, Napsterte." Barber warned him not to sell the shirts at a profit, which was no problem for Loubani. But when the company found about the slogans, it decided it had another issue. "It was deemed by the higher-ups to be too risqué," Loubani said. "It really upset me." Eventually, the company sent him a cease-and-desist letter. Loubani correctly figured that the company had bigger worries than he, and he continued to distribute several hundred shirts. "Maybe just because of Shawn's past, he and some of the other people didn't find these copyright issues compelling. I was one of them. I worked for the masses." As the rest of Napster "became this inflated, corporate thing," Loubani dropped out of the company's community, one of many radicalized youths who grew disillusioned as they realized that Napster was more and more about the money.

Shawn didn't give up on the shirt idea. As fans began clamoring for merchandise on Napster's message board, he tried to press the point. In April, Shawn e-mailed marketing VP Liz Brooks, copying Parker and Barber on the message. "We NEED to get some Napster merchandise on the site," he wrote, pointing them to the posted chatter. "This is crazy." Brooks responded that she couldn't do anything yet, because she had been