Kegs, Schmegs. Pick Up the Pace, LinkedIn

Reid Hoffman is known for many things, including founding LinkedIn, popularizing angel investing, becoming a venture capitalist at Greylock Partners, and having a giant brain. But he can also be conservative. For example, despite years of pleas from users and LinkedIn’s board members to add photos to the site, Hoffman refused, arguing that they could lead to discrimination suits against companies that use the service.

Hoffman finally gave in, but a conservative streak has defined LinkedIn throughout its seven years, and the company’s CEO since June 2009, Jeff Weiner, did little to dispel that perception at the Web 2.0 conference in San Francisco on Wednesday. Asked what will safeguard LinkedIn against faster-growing Facebook, Weiner cited “keg stands,” suggesting that job seekers need a clean, well-lighted place for potential employers to visit, far away from Facebook and the alcohol-addled photos that might appear there.

There’s no question that LinkedIn is a powerhouse. The company now has 85 million users, comScore shows that it’s seeing 60 million unique visitors each month, and its value is hovering around $2 billion on the secondary market.

But the company’s lack of chutzpah is frustrating. Instead of playing to win, it always seems that LinkedIn is playing not to lose. Unlike Facebook, which is willing to throw anything against the wall and see what sticks, LinkedIn is more like Craigslist, another remarkable business that seems stifled by a fear of killing the goose that laid the golden egg.

While Facebook and Google are constantly jockeying for talent, for example, LinkedIn rarely makes any high-profile personnel moves. Unlike other upwardly mobile tech powerhouses, LinkedIn has also made just two acquisitions in its entire history, both of them this year. (Unfortunately for LinkedIn, one of those acquisitions centered on a talented founder who left the company earlier this month, less than two months after his startup was purchased.)

Yet the biggest problem for LinkedIn is that unlike a Google or Facebook, it hasn’t given users a reason to come back every day. While it provides enormous value, it does so on an infrequent basis — when they’re looking for a job, or to hire someone, or to network. It was too slow to the market with an application platform and other connection tools, and while what’s now available is interesting, many users simply don’t think to look for it; they’ve already been trained to think first of Facebook.

The longstanding argument for LinkedIn -– which Weiner seemed to make again on Wednesday at Web. 2.0 –- is that people go to the grocery store for groceries and to the shoe store for shoes. He said, for example, that LinkedIn will only add more pictures someday if they can boost users’ productivity.

But how can LinkedIn know what works without experimenting more? Hasn’t the company heard of Wal-Mart, which just posted billions of dollars in profit on its sales of everything from groceries to shoes to, gulp, caskets? As distasteful as it sometimes seems, people do seem to want it all, in one place.

LinkedIn keeps pushing off talk of an IPO, with Weiner saying on Wednesday that the company wants to focus first on gaining critical mass on a global basis. And one former insider with whom I recently spoke said that while the company had been frustratingly slow to innovate until a few years ago, LinkedIn’s newest moves, including adding greater functionality to its user profile pages, enhancing its company profiles, and offering many new social networking integration features, should encourage naysayers.

Still, truly transformative companies like Facebook and Google are like sharks, always in motion. While LinkedIn can do well by nurturing what it’s built, one wonders if it isn’t leaving itself exposed in shark-infested waters. Already, says digital media analyst Jeremiah Owyang, “[W]e’re seeing enterprise software companies like [Facebook investor] Microsoft launch with Facebook features.” LinkedIn needs to “rapidly move forward.”