Connie Loizos

As VCs around the country schlep their way from pension fund to pension fund, family office to family office in search of commitments, another firm that had already closed on a whopping billion dollars has yet another $300 million to invest, according to SEC filings uncovered by the Earth2Tech blog. (Filings are here and here.) As Katie Fehrenbacher reports, Khosla Ventures now has one billion dollars for Khosla Ventures III, a traditional, stage-agnostic venture fund. His firm has an additional $300 million for Khosla Ventures Seed Fund for the highest-risk, presumably highest-reward investments.

Beginning a couple of weeks ago, we began shining a light on some of the unknown stars who are adding much of the value to some of Silicon Valley’s hottest companies. Raanan Bar-Cohen easily meets that bar. "Media engineer" of Automattic, the Web development company best-known for its open-source blogging software WordPress, Bar-Cohen joined the company in May 2007. Since then, he has helped to negotiate its transformation from a small, venture-backed startup into a powerhouse in the online publishing world.

MIT Professor Sandy Pentland says it’s possible to predict who will win business competitions based on the social signals they send, and he discusses how he is measuring the power of charisma in the newest edition of Harvard Business Review. In one experiment, says Pentland, executives at a party were outfitted with elaborate sensors that gathered data on their tone of voice, how they used their hands, and how closely they stood to other people, among other things. Pentland -- who directs the MIT Human Dynamics Lab -- was looking for cues predictive of which executives at the party would win a business plan competition later that same week. As it happens, they were the most energetic executives of the group.

Greg Gretsch of Sigma Partners has reason to feel confident about his future as a venture capitalist. He backed the storage company EqualLogic, which sold to Dell in 2008 for a tidy $1.4 billion in cash. He led an investment in the Web services management company TalkingBlocks, which raised $9.5 million from VCs and sold to HP. (Details weren’t disclosed but Gretsch says it was a 2x for Sigma). Gretsch has also seen some nice exits from angel investments made long ago. The audio player company Slim Devices, founded in 2000, was one of those deals. It raised $5 million and sold to Logitech for $23 million in 2006. Gretsch was also an early backer of Postini, which raised $26.45 beginning in 1999. It sold to Google for $625 million in 2007. Even still, Gretsch says that as he enters his 10th year in the business, he’s worried about a tipping point. To wit, Gretsch doesn’t think that the longer you’re a VC, the more skilled you become in picking winners. Instead, he theorizes that if you’re a VC for more than 10 years, you’re likely to grow worse at your job over time.

Malcolm Gladwell’s latest piece in the New Yorker is about how “entrepreneurs really succeed.” It reminded me of two things. Gladwell is a brilliant storyteller. He's also a purveyor of garbage. Gladwell devotes several thousand words to the premise that successful entrepreneurs aren’t swashbuckling risk-takers, but rather are calculating predators who exploit opportunities before anyone else recognizes them. Smart businesspeople are conservative; they aren't gamblers, says Gladwell, who goes on to ask: “Would we so revere risk-taking if we realized that people who are supposedly taking bold risks in the cause of entrepreneurship are really doing no such thing?” Except they are. Because an entrepreneur minimizes his or her downside doesn’t render the risk meaningless. And is it really so hard to believe that successful entrepreneurs are both bold and cautious? (It would be far harder to believe that success is one dimensional, but Gladwell has already turned several grossly oversimplified theses into best-selling books, so why stop now?)

Brightroll calls itself the world’s largest branded video advertising network, saying that it has served billions of advertisements since it was founded in 2006. Whether that's the truth or hyperbole, one senses that its 32-year-old cofounder, Tod Sacerdoti, knows his stuff when it comes to the world of Internet marketing. Sacerdoti first "caught the bug" covering Internet marketing for Robertson Stephens, straight out of Yale. As he moved through several business development positions, including at venture-backed startups Spoke Software and Plaxo, Sacerdoti maintained Internet marketing side projects, including assembling a portfolio of 1,000 domain names. “I was small time, but I was always involved in lead gen stuff." Then, inspiration struck. Plaxo was helping YouTube create a distribution widget, so people could share videos with their friends (and YouTube could suck up their address books). Sacerdoti, who was involved in the process, says the deal gave him access to data that wasn’t public for a year -- data that pointed to a massive consumption of video online. Six months later, Brightroll was born. Sacerdoti and I talked yesterday about Brightroll’s fast-growing business, along with some of the shadier tricks of the video advertising trade. It's an interview that anyone wanting to better understand the world of online video advertising should read.

Sigma Partners' Greg Gretsch, on the not-so-transferable skills of venture capitalists -- many of whom are being forced to exit the industry as it contracts: "Where does everyone go? I don't know, but don't send them my way. After roughly 10 years in the industry, my own ability to 'do' today is a little rusty."

Maybe it’s his new grandson, or perhaps it was the warm fish tacos we dipped into Tuesday at Fog City Diner in San Francisco. But Stewart Alsop seems more at ease these days, including with his role in the VC universe. “People don’t take things personally enough in venture capital,” the the ex-journalist-turned-investor, told me. “They act like it’s this analytical process when in reality, it’s completely subjective. There shouldn’t be this distance that exists between investment professionals and their investment decisions.” There’s no question that Alsop -- who spent nearly eight years at New Enteprise Associates -- is happier since striking out on his own five years ago with former In-Q-Tel chief Gilman Louie. It’s plain, just by looking at him. Also clearing up is the immediate future of Alsop Louie Partners, which, despite the overall contraction in VC, recently held a first, $20.25 million close, on its second fund. (Alsop refused to discuss fundraising, but you can find the Form D they filed with the SEC here.) I assume the target is around $75 million -- which is what Alsop Louie's first fund closed in in 2005 -- though the filing doesn't specify.

Last month, as Christmas day neared, National Venture Capital Association president Mark Heesen was pacing around his Washington office, worried and wondering what might happen once the Senate voted on a landmark bill to reform the nation’s health care system. “Our major concern was that [the senators] were all exhausted, and they had this trainload […]

As 2010 gets underway, tech watchers are waiting with baited breath for Facebook to file its S-1, a move that would invariably swing open the IPO gates to a number of other social networking startups that have millions of users and envy-inducing revenue numbers. But what if a Facebook IPO isn't as imminent as everyone anticipates? Yes, it introduced a dual-class structure in November -- just as Google did before going public -- but Mark Zuckerberg doesn't make decisions on anyone's timeline but his own, seemingly. If the company decides to wait, will LinkedIn and Zynga executives be left looking at their timepieces and tapping their shoes? Earlier today I explored the question with Terry Schallich, managing director and head of equity capital markets at the tech-focused investment bank Pacific Crest Securities. Get our Q&A after the jump...