Will Yahoo Try to Get Its “Cool Again” by Doing a Deal for Tumblr?

Earlier this week, Yahoo CFO Ken Goldman spoke at JP Morgan’s Global Technology conference and underscored the need for the aging Silicon Valley Internet giant to attract more users from the coveted 18-to-24-years-old age bracket. Along with more marketing, he explicitly said Yahoo needed to be “cool again.”

“One of our challenges is we have had an aging demographic,” said Goldman at the Boston event. “Part of it is going to be just visibility again in making ourselves cool, which we got away from for a couple of years.”

According to sources close to the situation, that could mean a strategic alliance and investment in or outright buy of perhaps the coolest Internet company of late: Tumblr.

Sources said the talks were serious, but any kind of deal — of course — could come to naught.

But it’s not the first time Yahoo CEO Marissa Mayer has been interested in the New York-based hipster blogging service. As an executive at Google, she had closely watched its fast growth, along with that of Foursquare. Since she took over at Yahoo, several sources said that she has met with its top execs, including founder and CEO David Karp.

But sources said that interest has gotten stronger more recently, coming at the same time as Tumblr has been stepping up its efforts to raise a large funding round that could value the New York company at $1 billion. In a series of fundings since 2007, Tumblr has raised $125 million so far, at a reported valuation of $800 million.

In the latest round, one source close to the situation said Tumblr was considering “strategic” investments, which would presumably be of the kind that Yahoo had tried and failed to do recently with France’s Dailymotion video service. Since then, Mayer and her team have looked at the ongoing deal to purchase Hulu that has many possible other bidders.

Tumblr is different from Dailymotion or Hulu, of course, in that it focuses heavily on user-generated content, largely text and photos, although there is an increasing use of video on the site.

But this puts it directly in Yahoo’s main wheelhouse, especially recent efforts to undergird its strong set of existing media offerings to appeal to a different audience and also get into the social space via consumer-based software solutions that are both elegant and easy to use.

“If you could pick a company that fits in with what Marissa Mayer has demonstrated in her career — aesthetics software technology and fast-growing — you could not land on a better choice,” said another source.

That said, Yahoo has been sticking to smaller acquisitions under Mayer’s regime, spending very little on a clutch of small mobile startups to up its game in the important sector. And at the same investment conference, Goldman also said additional M&A would continue to be smaller for Yahoo.

Still, any kind of deal with Tumblr could certainly bring Yahoo a big, young audience. Its worldwide traffic was at 117 million visitors in April, according to comScore. On its home page, Tumblr claims it has 107.8 million blogs and 50.6 billion posts. U.S. desktop traffic to Tumblr was 37 million in April, close to LinkedIn and Twitter, although Twitter obviously has much more via mobile.

But figuring out how to make money from that audience is a task that the company has only recently started to tackle.

Like other recent Web startups that have seen rocket ship growth — see: Twitter, Facebook — Tumblr resisted advertising for its formative years, and its user base seems particularly unwilling to accept standard banner ads. In addition, many industry observers think that Tumblr’s pages are packed with porn and/or other questionable content that would scare off advertisers.

But within the last year or so, Tumblr has started selling modestly sized “native ads” promoting brands’ Tumblr pages, on users’ “dashboards.” That’s the equivalent of running ads in a Facebook user’s News Feed or a Twitter user’s main feed.

Initial signs are promising. Tumblr told Forbes that it generated $13 million in revenue last year, and suggested it could do as much as $100 million this year; people close to the company say its momentum has continued this year.

In addition to figuring out its top-line business, Tumblr and its backers have also been spending a long time trying to figure out a managment structure. Even Karp’s strongest backers say that the 26-year-old needs help running the company, and for months they have been looking for a “Sheryl Sandberg”-style COO candidate.

“David is very charming, and clearly very very bright, and understands the product,” said an executive who talked to Tumblr about the role. But, “he’s incredibly confrontation averse, and there’s almost a ‘Game of Thrones’ palace feeling to the management team.”

Possibility of death by wildfire aside, sources said that the search has yielded two or three candidates that Tumblr is considering. It is a key hire since the company needs to build out an extensive infrastructure quickly, given its sharp consumer growth, including fielding a more robust advertising team. Tumblr hired an experienced exec, Lee Brown, from Groupon last fall, who has been busy hiring more sales execs. Interesting aside: Brown was a longtime Yahoo ad exec.

But building out the needed structure at the company is a long slog, and Tumblr might be seeking more help one way or another.

Yahoo declined comment and Tumblr has not gotten back to us as yet.