In 1999, Alternative Media Inc.'s principals were tired. Alternative weeklies had proven to be a lucrative business model, and Williams says he was ready to move on.
"Every so often you want to change up and refresh, reset," he says. "That's what we did. We did realize in 1999 that it was a really good time to sell. ... We were ready to step aside. We had worked hard."
AMI had multiple offers for the publications, and they ultimately chose to sell to Times Shamrock Communications because the family-owned media business didn't express interest in breaking up the format or reimagining the publications – they wanted to build on the success that AMI had with the alternative-weekly format.
"I don't think we saw the dot bomb coming," he says.
The "dot bomb" did eventually come, and although alternative weeklies had historically weathered recessions, downturns and changing media trends fairly well, the Internet wasn't just a trend. It caught up with every print publication in the nation. Orlando Weekly responded by launching orlandoweekly.com in the late 1990s and creating Bloggytown, its inaugural news blog, which adopted the same snarky, offbeat tone as its print counterpart, Happytown™.