Bill Gross, the serial entrepreneur who pioneered search advertising, is unveiling a venture on Monday that aims to make money by allowing people using Twitter to bid on key words to give their posts top ranking.
Called TweetUp, the service will also organise posts according to their popularity as measured by how often readers repost them and click on links they contain.
Gross said he had signed deals with other outside Twitter services like Seesmic, TwitterFeed and Twidroid to display TweetUp’s rankings, and TweetUp will split revenue evenly with each partner.
The gamble is whether Twitter-users will pay to get their messages noticed — and whether other Twitter users will view such paid placement as legitimate.
TweetUp has raised $3.5 million from a group of investors that include Index Ventures and Revolution, the investment firm of Steve Case, the former chairman of AOL Time Warner.
Case said he was persuaded to invest in TweetUp by Gross’s history. “TweetUp is to Twitter what Google is to the Web,” Case said.