Ex-Googlers Use Their Fortunes to Hunt for the Next Google

Chris Sacca, the former WiFi guru at Google, made a fortune as the company's stock soared. Now he is using his money to hunt for the next Google.

Sacca, 32, left the Internet search company this month for a new career as a venture capitalist. He joins a growing number of Google millionaires hoping to parlay their newfound wealth into even greater riches by bankrolling technology start-ups.

Three years after Google went public, a fast-growing network of hyper-connected company veterans is fanning out across Silicon Valley. Some are joining the venture capital firms that financed the tech boom of the 1990s. Others are raising investment funds or backing embryonic companies with their own money as so-called angel investors.

Sacca had a plum job at Google. Among other things, he spearheaded the creation of a free WiFi network in the company's hometown of Mountain View, California.

"I had one of the best jobs in the world," Sacca said। "But there is a world of opportunity."

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Comscore November 2007

Continuing on from my message about Nielsen Online's latest search popularity stats, I'm now moving to those from comScore। For November 2007 -- as with Nielsen -- it's the same-old, same-old. Google's on top, followed by Yahoo and Microsoft. But in terms of raw searches, while Google still shows gains, at least Yahoo can point to six months worth of holding steady.

The comScore stats are here, showing the share of all searches handled by the five "core" search engines, as comScore calls them:

• Google: 58.6%
• Yahoo: 22.4%
• Microsoft: 9.8%
• Ask: 4.6%
• AOL: 4.5%

Here are the numbers in pie chart format:

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Digg is close to announcing its sale to a major media player

Digg is close to announcing its sale to a major media player for $300 million to $400 million, according to sources close to the company, I hear. When I floated this Digg rumor past some knowledgeable friends, several scoffed: "When isn't Digg up for sale?" It's true: The news-discussion site is perpetually in talks -- but we hear the price tag always sinks potential deals before they're consummated. CBS, for example, backed off, with effervescent dealmaker Quincy Smith citing the media company's bubbly $280 million purchase of Last.fm as the reason it couldn't bid a high price for Digg. Things are different now, though.

Digg recently inked a $100 million, multiyear ad deal with Microsoft. On those revenues alone, Digg's acquirers could easily justify a $300 million to $400 million purchase price; if Microsoft is paying about $30 million a year for Digg's banner-ad inventory, paying that price would mean a modest 10x to 13x multiple on revenues.

So who is it? A source rules out all the big Internet players -- not Microsoft, not Google, not Yahoo. CBS, a big Web acquirer of late, has taken itself out of the running. So who could it be?

Two possibilities: The New York Times Co. and the Washington Post Co. Both the Times' Arthur Sulzberger and the Post's Donald Graham are big believers in a digital future. And both can see firsthand how much traffic Digg contributes to their websites. If I were to place a bet on those two? I'd say the Post, which already owns Slate and has close dealings with Microsoft; Digg's Microsoft ad deal would not discomfit Graham the way it might other businessmen. The Post also has a stronger balance sheet, with a market cap four times the Times'.

That's pure speculation, of course. Acquisition talks fall apart all the time -- and for Digg, especially, with its history of almost-but-not-quite deals, I wouldn't be surprised if nothing came of this latest rumor. Still, it's telling that the Valley's talk about Digg has changed from scoffing at its overinflated valuation to talking about who's willing to meet Digg's terms.

Digg CEO Jay Adelson gave me the standard noncomment about "rumors and speculation." But given his transcontinental commute from New York to San Francisco, I wouldn't be surprised if he'd be glad to put his company up for sale. For founder Kevin Rose, a sale would be more emotional. He'd have to be comfortable with whoever buys the company, since he'd likely stay involved. His Diggnation podcast, which draws on headlines from Digg, is one of the centerpieces of his other startup, Revision3. Digg's contentious audience, too, might not take to the site's new owners. That's the biggest obstacle, I suspect, to any deal happening. Those who would profit from the wisdom of crowds must contend with their madness, too.