We were hard on instant message startup Meebo in March when it was raising a $25 million round at a $200 million valuation. While it has gained tens of millions of users in a couple of years, it has yet to generate significant revenue.

Today, in one of the Mountain View, Calif. company’s most explicit efforts yet to make money, it is introducing interactive ads.

Meebo’s ads will appear at the bottom of its chat windows (screenshot sample of an ad for the movie The Incredible Hulk, above). Click on an ad that you find interesting and it will expand on to the page, and may include content like a video to watch or a simple video game to play (big screenshot, below). Launch partner advertisers include Havaianas, Sony Electronics, Universal Pictures, and the rock band Weezer.

Meebo says more than 75 million web site URLs are shared on it every month — people sending web links to each other on its services. So if the ads appeal to users, the ads will be shared, it hopes. The result is that advertisers will have a clear new channel for spreading information virally. Most social network advertising to date has been untargeted banner ads that aren’t worth much to anybody.

If you want to share an ad, you can add a link to the ad within your chat window (see screenshot). The ads will also run on Meebo Rooms, chat room widgets that you embed on other sites. Note that users in these rooms make up most of Meebo’s 35 million monthy unique visitors.

Meebo has previously been working on partnerships with music labels, with video ad network company Videoegg and others to sell advertising. It has most recently been expanding its sales team. The company hasn’t released financials, but last we heard, it wasn’t seeing significant revenue.

The larger trend, as we’ve covered, is that social networks and other web services are trying to figure out how they can connect brand advertisers with their millions of users. If it turns out that Meebo users — the majority of whom are teenagers or twentysomethings — do like to share these ads, then Meebo may start making some serious money. Advertisers are looking for more precise ways of reaching these younger audiences. Social networks and social services like Meebo replace time spent watching TV or reading the newspaper, but brand advertising on these sites has until recently been limited to poorly-performing banner ads.

And so, if Meebo’s effort works, it will likely be duplicated and iterated upon by other social services that provide IM. For example, Facebook’s own IM service, only recently launched, could likely run similar ads.

VentureBeat's mission is to be a digital town square for technical decision-makers to gain knowledge about transformative enterprise technology and transact. Discover our Briefings.