VentureBeat

If you get superstar athletes to invest in your youth-sports social network, does that mean you’re onto something big?

WePlay seems to think so. The company, which combines standard social network features with scheduling functionality to manage practices and games, hopes to attract young athletes and their parents and coaches, and has just raised $8.6 million in its second round of funding. While Deep Fork Capital led the round, previous investors Derek Jeter, LeBron James and Peyton Manning and FirstMark Capital came back as well.

If WePlay were any other kind of start-up, we’d wonder why it would raise money from athletes who know nothing about start-ups. While Curt Schilling has a minor reputation for knowing his way around the tech game, Derek and LeBron certainly do not. But in this case, it makes good sense. WePlay is competing in two competitive markets without any major differentiators in either one. On the youth-sports social network side, it is up against the more established Takkle. On the scheduling side, there is RosterBot and TeamSnap.

Having sports superstars behind it could give WePlay an edge. The company is not shy about it: The two most prominent features on the site right now are a big square banner offering a chance to meet Derek Jeter and a 15-day old “featured member” blog post from none other than LeBron James.

That’s the difference, right there.

Ads that appear next to search results are one of the most valuable forms of online advertising, because they are matched with users’ searches for things they want to buy. You see an ad next to a result for what you’re looking for, then you click on the ad instead of the result, and make a purchase. But organizing large search ad campaigns gets complicated, because these ads are matched up with a user’s search results based on keywords submitted by competing advertisers.

That’s where Clickable comes in — and one reason why it has just raised a second round of $14.5 million from some marquee investors. The New York-based company provides web-based project management software that helps small to medium sized businesses organize their search-ad campaigns, replacing Excel spreadsheets that many of these advertisers currently use. It’s dashboard-style interface lets users plan search ads across search engines, including Google, Yahoo and Microsoft.

Clickable launched publicly in February — although we’ve been tracking it for some time — and it isn’t saying much about how it’s doing beyond that it’s gaining up to 200 new clients per month. But the funding is certainly a positive indicator for whatever is happening behind the scenes. It has raised a total of $22.5 million so far. The latest round was led by The Founders Fund, with existing investors Union Square Ventures and FirstMark Capital participating. Earlier individual investors also joined in, including Jon Miller, a former AOL chief executive, current Yahoo board member and Velocity Interactive Group partner, and Peter Thiel, co-founder of PayPal and Managing Partner at The Founders Fund.

Clickable is trying to be a comprehensive site for newbie search advertiser needs. It has built out its home site as a sort of learning community for beginner search-ad buyers — a group that otherwise experiences a lot of “churn,” with many people trying these ads and leaving, chief executive David Kidder tells me. The site includes user guides, case studies and other educational features. This community, in turn, has helped the site on search engine rankings, leading to more first-time customers who find the company through searches.

Among other features, the software includes a recommendation tool that lets advertiser see how well their chosen ad keywords are performing, or if a competitor’s keywords are doing a better job of reaching desired users. This feature recommends potential keywords to help an advertiser better target their ads and beat out competitors — faster and easier than crunching data about keyword performance within spreadsheets.

Larger companies providing search-ad optimizing services include SearchForce, Marin Software, Efficient Frontier and Omniture. These companies charge significantly more for complex optimization software designed for larger advertisers, while Clickable is aiming for advertisers who spend between $1,000 and $50,000 per month, Kidder says.

Closer competitors to Clickable include ReachLocal, Yodle and other companies aiming for small businesses that want to bring in more business through search results. These companies, like Clickable, also use on-the-ground sales teams and search ads to drum up business. Also of note to Silicon Valley advertising technology folks: Clickable made the point to me that its New York location has helped it develop relationships with media-world clients including advertising agencies — early users that have in turn helped the company refine its product. Finally, perhaps Clickable’s most direct competitor is Enquisite, which offers its own search ad keyword recommendation web software.

While Clickable is initially focused on search ads, it also plans to move into offering optimization services for clients running video ads, and other forms of online advertising.

Venture capitalists tend to stay away from funding game developers because games are considered a hit or miss business. But Riot Games has convinced some VCs it has some hits on the way. The company has raised a $7 million round of funding from Benchmark Capital and FirstMark Capital.

The money will go to complete the company’s first game, said Marc Merrill, president and chief marketing officer of the Los Angeles company. He isn’t telling what the game is. But it will exploit an idea dubbed “session-based gaming,” he notes.

Merrill said such games are in the middle of the spectrum between commodity-like Flash games, such as online poker, and high-end fantasy role-playing games such as “World of Warcraft.” They’re quick hits that people can play for a short time, like a pick-up basketball game. When you sign off, the game goes away.

But Merrill said that the company is also developing a platform that enables social networking and community features that last beyond a single session. Veteran game developer and Benchmark partner Mitch Lasky will join Riot Games’ board.

Brandon Beck, 26, is chief executive of the company. He and Merrill, 27, both hail from outside the game industry. Beck is a former consultant at Bain & Co. while Merrill ran marketing at business-to-business media firm Advantastar. It’s all the more impressive then that they have scored money from top VCs and have recruited a team of 30 developers who have worked on popular titles from “Dungeon Seige” to “Sly Cooper.”

Merrill said the company will sell its games direct to consumers via its own online platform. The company was founded in September, 2006. Within a couple of months, the company expects to release details of its first game. One of its competitors will be the industry’s biggest company, Electronic Arts, which is launching a session-based free game dubbed “Battlefield Heroes” for the PC this summer.

“There are some forward-looking companies here,” Merrill said. “The games are replayable and short, simple to play but difficult to master.”

[Photo credit: Flickr timophoto]