In an effort to minimize the impact of massive layoffs that Yahoo’s top management has been planning, according to sources close to the situation, one of the latest ideas to save costs and presumably jobs by new CEO Scott Thompson is to sell off much of its advertising technology platform, including Right Media.

And among the possible buyers Thompson has been targeting in recent visits: Google and Microsoft, as well as Silver Lake, the private equity firm that had once been talking to the Silicon Valley Internet giant about making a large investment in the company.

(That particular deal has gone south, but there is always yet another scheme on the horizon at Yahoo!)

The concept behind such a sale, according to several sources inside and outside the company, is to turn a cost center into a revenue source, with Yahoo essentially outsourcing a business that was a cornerstone of its strategy. A negotiable number of employees affiliated with those units would then move over to the new owner.

The most ideal plan, said sources, would be to sell Yahoo’s whole advertising technology “stack,” including the Right Media Exchange, a marketplace for advertisers, publishers and ad networks to trade online ads. Yahoo bought it for $700 million in 2007.

According to info on the company’s site, it has “300,000 active global buyers and sellers and more than 11 billion daily transactions.”

Also part of the possible package is APT, a system Yahoo has built to make buying and selling online advertising easier. In addition, Yahoo’s technologies for display-ad serving have been mentioned as a possibility for sale.

It’s unclear what the potential sale means for the new ad strategy that U.S. boss Ross Levinsohn and his lieutenant Jim Heckman have been pursuing since last summer. That plan included its own acquisition of ad network Interclick and an attempt to sync up with rivals AOL and Microsoft in an effort to fend off Google and some third-party players, like ad networks.

But the reason for contemplating much a major move — which has been considered before, but never has been seriously offered — are obvious: While Yahoo once dominated this arena, it has steadily lost ground, especially to Google. The search giant has made almost all of its money in search-related ads, but has been moving aggressively via its DoubleClick and other ad-serving entities into higher-level ads.

Microsoft has also been trying to compete, as has AOL, but it’s getting to be an expensive race, and one where Yahoo would have to make major investments to once again gain momentum. Building up this business again had been the aim of co-founder Jerry Yang, who wanted to go big in the arena in a number of ways before he left the company earlier this year.

But those days seem to be over at Yahoo.

“A lot of what has happened so far under Scott [Thompson] has been trying to find more revenue anywhere it can be generated, and get out of businesses that are not growing,” said one person. “Right now, it’s a lot about what we shouldn’t do rather than what we should.”

That has meant visits to see both Google and Microsoft about possible deals by Thompson, with the involvement of CFO Tim Morse and Chief Product Officer Blake Irving.

Thompson (pictured here) has also recently been talking to Silver Lake about the ad-platform sale, in a deal that might include the Andreessen Horowitz venture fund. This would be a different kind of transaction, said sources, in which a separate company would be formed, with Yahoo owning a piece and contracting with the new entity to provide ad technology.

All this activity is related to the layoffs in the works of perhaps thousands of employees, which were to have been communicated to the company this week.

Sources said those have been delayed for some weeks for several reasons, including whether to consider more deeply if certain larger business units can be spun off, sold or somehow transformed. (To be clear: Major layoffs are still being planned, but now might take place in two parts, said sources, in what is a quickly changing and volatile atmosphere at Yahoo.)

Another area being looked at, said sources, is Yahoo’s search advertising partnership with Microsoft, which has not been as successful as had been expected. While Yahoo has been working with the software giant about improving the results, Thompson has apparently been contemplating other possibilities, including working with Google (calling all regulators!) and/or laying off up to 900 employees who work on the company’s search offering.

Any of these moves could, of course, cause a firestorm of controversy, which Thompson appears to not worry much about. He was the driving force in Yahoo’s patent lawsuit against Facebook earlier this week, which is largely attracting a negative reaction across the tech landscape.

A number of prominent voices have spoken out against the legal action, including well-known VC Fred Wilson, who yesterday penned a poisonous blog post, titled “Yahoo Crosses the Line.”

It ends thusly: “I am not writing this in defense of Facebook. They can and will defend themselves. I am writing this in outrage at Yahoo! I used to care about that company for some reason. No more. They are dead to me. Dead and gone. I hate them now.”

Ouch!

Also weighing in publicly via Twitter was former Yahoo director Eric Hippeau, who was one of the company’s first investors, which is embedded below:

Pathetic and heartbreaking last stand for Yahoo bit.ly/yirCcj It’s all over. I loved you very much.

— Eric Hippeau (@erichippeau) March 13, 2012

Double ouch!

All I can say is that Thompson certainly has a lot of gumption. That has actually been his M.O. from the start, said several sources, with the former president of eBay’s PayPal payments unit and dark horse cold-emailing his way into the Yahoo CEO job.

True story: He had not been among its list of possible candidates — largely because he had been placed in his job at eBay many moons ago by Heidrick & Struggles, which was conducting the Yahoo CEO search, and that’s a talent acquisition no-no to poach someone you placed.

That did not stop Thompson, who thought he might be good for the job and reached out directly to board members at the end of the selection effort, which then led to the search committee and soon enough to the job in what was a very quick vetting and secretive (although not secretive enough!) hiring process.

Since then, Thompson has been on a tear, from working on a restructuring to trying to assuage activist shareholder Dan Loeb to helping put the kibosh on its Asian stake sale talks to suing Facebook. And now this sale effort, too.

If the peripatetic Thompson — who might need a dose of Ritalin before this thing is over — wanted to get noticed by the tech powers that be: Mission accomplished!

“He’s definitely someone who appears to have decided on shooting the moon with a lot of these actions,” said one person close to the situation, referring to the move in the card game of Hearts, which is a risky gambit to capture every penalty card worth 26 points in order to win. “I just hope no one loses an eye in the process.”

(That would be triple ouch, by the way.)

No comments all around, but everyone was certainly cordial on this rainy morning.

Now, Kik Interactive, the company that introduced super-simple mobile messaging (and became the target of a lawsuit filed by RIM), is joining the multiscreen video party.

Kik’s new app, called Clik, allows you to view video that’s on your smartphone on a bigger connected screen.

Unlike Apple’s AirPlay, which requires users to be on a Wi-Fi network, or Movl’s apps for Samsung TVs, which in some cases require Wi-Fi, Clik uses the 3G capabilities of your phone and doesn’t require access to a special device on the receiving end — just any screen that is connected to the Internet and can run a browser.

For users concerned about the app burning up your phone data, Clik explains this by saying the app doesn’t stream the content to your TV or computer; it just instructs the browser to play video.

Once a user has downloaded the free Clik app to an iOS or Android device, he or she can navigate to ClikThis.com through a Web browser and scan the giant QR code that appears on the home page. The Web page then becomes a video viewing platform for the videos that appear on the smartphone. The interactivity between the two is pretty seamless, with the videos starting, stopping and switching as soon as a command is received from the smartphone.

One of the initially apparent drawbacks is that ClikThis.com is just a bare-bones host page of the video, with no command buttons on it, so you can’t start and stop the video from the browser — it has to be done through the phone.

In terms of video quality, it’s determined by the quality of the Web video and not the video as it appears on the phone.

Kik is launching Clik today, along with a software kit for developers to get cracking on different applications for the Clik platform. For now, it’s rolling out with a YouTube app. Creator Ted Livingston sees the potential for multi-user, multiscreen sharing: You’re at a party, say, and everyone’s using Clik on their phones, so they can all share and control the game, video or music playlists.

Kik’s battle with RIM over the messaging app is still continuing, though last fall Kik said it was working on a new version of its messenger that would work on RIM BlackBerry devices. Despite the legal fracas, Kik managed to nab $8 million in Series A funding last year from RRE Ventures, Spark Capital and Fred Wilson’s Union Square Ventures. Wilson and Adam Ludwin from RRE also joined Kik’s board.

I am totally convinced that the world of social media is not consolidating around one “winner takes all” social platform.

– Fred Wilson

But here’s a picture of the Union Square Ventures partner watching the New York-Toronto game on his big screen, after all. He was able to get a feed of the game from a pirate aggregator called atdhe, he explained on Twitter. “Worked great for me. #screwcable”

The fact that it’s easy to get pirated TV, delivered over the Internet, isn’t new. It’s certainly not a revelation for Wilson, one of tech’s most prominent and successful venture capitalists, or his 199,000 Twitter followers.

Still, it’s always worth pointing out just how easy it has become. It’s particularly important when it comes to live sports, because that’s supposed to be the one thing that keeps everyone — or many people, at least — paying (a lot) for cable.

I’d be surprised if the Knicks game looked very good on Wilson’s Panasonic — when I tried it on my MacBook, it was pretty blurry.

But it’s better than nothing, which is your only alternative if you’re a Time Warner Cable subscriber in New York City right now (the NBA’s League Pass subscription service, which is supposed to give you access to every game in the league, has a regional blackout).

It’s also worth noting that while Wilson is directing his anger at the cable guys, who are easy and deserving targets, the NBA itself is a supporter of ProtectIP and SOPA, which are designed to make sites like atdhe harder to search for on Google, Twitter, etc.

I’m quite sure that Wilson would say he’s not advocating piracy, but simply trying to access something he’s already paying for (or in other cases, grabbing something he isn’t allowed to buy for unfathomable reasons).

Still, I can imagine a Big Media lobbyist using Wilson’s tweets (or, I suppose, this post) to help explain why the legislation should pass. And I’m certain that’s not what Wilson was aiming for.

Here’s a panel I did last week at the Privacy Identity Innovation conference on Sand Hill Road in Silicon Valley.

The panel was called “Social Sharing and the Data-Driven Economy.” And while that sounds a little dry, it was a lively session that included: Jim Adler, Chief Privacy Officer and GM, Data Systems at Intelius; David Glazer, director of engineering for Google+; Roger McNamee of Elevation Partners; and Fred Wilson of Union Square Ventures.

All have deep experience in the social networking space and insights into its implications, so it’s a good video to watch if you’re interested in where it’s all going.

Enjoy:

Social Sharing and the Data-Driven Economy from Marc Licciardi on Vimeo.

[UPDATE: Twitter confirmed our post in a statement:

"Bijan Sabet and Fred Wilson both played important and greatly appreciated roles in our success. Both saw what Twitter could become before most anyone else. We look forward to their continued input as both investors in the company and passionate users of the product."]

Wilson, a high-profile principal at Union Square Ventures, was one of Twitter’s earliest backers, and for a long period helped to steer the company’s direction. Sabet’s Spark Capital was also an early investor.

Both funds have sold some of their Twitter holdings via secondary market sales. But people familiar with the companies say both continue to hold a majority of their stake in Twitter, now valued at $8.4 billion.

If there’s a backstory here, it will be hard to tease out. People familiar with all three companies tell me there’s no bad blood behind the move. The one thing that’s easy to understand — for now, at least — is that Twitter’s board is a little less unwieldy.

It has been swelling over time, and last year got even bigger when Flipboard’s Mike McCue, former DoubleClick CEO David Rosenblatt and Silicon Valley advisor-to-many Peter Currie all joined. Other board members include Benchmark’s Peter Fenton and CEO Dick Costolo.

And, for a relatively young company, Twitter’s corporate history is full of twists and turns. The most recent and prominent ones were Costolo’s ascension from COO to CEO a year ago, when he replaced co-founder Evan Williams; and co-founder Jack Dorsey’s return to the company last spring to head its product efforts, after being pushed out in 2008.

I’ve asked Wilson, Sabet and Twitter for comment.

[Image credit: Lachlan Hardy]

Betabeat first reported Union Square’s involvement today; sources I’ve talked to tell me this has been more or less a done deal for about month.

Turntable is still lining up angel investor/advisers that it wants to recruit from the ranks of high-profile music industry executives, and once that’s done they’ll make the whole thing official. I’ve asked Turntable and Union Square for comment, but don’t expect to hear back.

Closing the funding round — which I believe will be somewhere in the $6 to $7 million range — will give Turntable’s Billy Chasen and Seth Goldstein time to tackle their real challenge: Figuring out how exactly they’re going to work with the music industry.

The service, which lets users “DJ” streaming music for crowds who gather in online listening rooms, doesn’t have any deals with major record labels and publishers. Earlier this summer, the company told me that it planned to move forward as a “non-interactive” Web radio service, a la Pandora, which doesn’t have licenses, either: Instead it operates under the umbrella of the Digital Millenium Copyright Act, and pays copyright holders a rate established by an arbitration board.

But people familiar with the company say it is considering trying to strike deals with the labels after all. The upside is that negotiated pacts could give the service much more flexibility. The downside is that getting those deals done could take a long, long time — just ask Spotify, which took more than two years to break into the U.S.

At least one music industry source I trust, though, believes the fact that Spotify has gotten to the U.S. means there’s now some sort of music industry/business development glasnost. According to this line of thinking, the big labels are now more willing than ever to consider new arrangements, and perhaps Turntable can squeeze in through this window of opportunity.

My bet is that you can’t ever go wrong wagering on big music label intransigence, but we’ll see.

In the meantime, it’s interesting to note that this is the second big bet Union Square has made on music — at the beginning of the year, it announced an investment in music distributor SoundCloud.

Union Square partner Fred Wilson has always had a big personal interest in music, but until this year he hasn’t put his company into any music bets, precisely because of the licensing headaches that come from most ventures. Maybe the business really is changing.

Etsy, the handmade goods online marketplace, has appointed its CTO Chad Dickerson (pictured here) as CEO. He replaces founder Rob Kalin, who stepped back into the top leadership role in late 2009.

Kalin is again transitioning out of the day-to-day management at the New York-based start-up.

In a blog post about it, Dickerson wrote, in part:

With engineering well in hand and a strong partner in Adam Freed (our COO), it’s time for me to focus my attention on other aspects of the business. I’m stepping into the role of CEO at Etsy, and I’m looking forward to working with all of the teams at Etsy to move faster as we scale while staying true to our values.

Before we talk about the future, I wanted to say a heartfelt thanks to Rob Kalin. Rob started Etsy. It was his idea. Hiring me was his idea. We all owe him a huge debt for starting the company that we all love, and I owe him a huge personal debt for bringing me to Etsy. Thanks, Rob.

As CEO, I’m going to focus the entire company on moving faster and and more purposefully, learning by doing, iterating, and taking risks. That’s a long way of saying we’re going to get things done. I’m going to prioritize the needs of the Etsy community in the broadest sense — Etsy’s sellers, how we work with each other within the company, our local communities, and everyone whose lives we touch. It’s a big responsibility that I take very seriously.

Etsy added former Google exec Freed in mid-2010.

Union Square Ventures’ Fred Wilson also addressed the management change on his blog, A VC:

“Transitions are never easy on the people involved and the company that goes through them. But they are inevitable in any company’s evolution. Some of them work out well and others not as much.”

Google+ fills a void between public and private, it serves what is likely to be an older demo less interested in hooking up or hipstering out and more interested in the social utility it provides.

A VC Fred Wilson, in a later part of the same post on social networking companies.

In any case, I hope Google+ succeeds. Given the blog posts saying this will kill Tumblr, Twitter, Foursquare, etc, you might wonder why I feel that way. Well first, I don’t think competitors kill companies and services. I think the vast majority of “deaths” are self inflicted.

– A VC Fred Wilson, on the newest entrant into social networking game.

Parents are always looking for ways to position their children for success, from piano lessons to Mandarin immersion. In the Wilson household, that means encouraging the kids to express themselves on the Internet. Unlike parents who struggle to limit kids’ computer use, Fred and Joanne Wilson want their kids to be comfortable with the latest in technology.

The parents and kids publish a combined nine blogs. They bring a duffle bag on family trips just to carry all the cords, adapters and batteries for their electronic devices. Mr. and Ms. Wilson, both 49, write almost every day on their blogs, which cover everything from financing start-ups and music (his) to entrepreneurs, family and the key to cooking a prime rib (hers).

Jessica, 20, and Emily, 18, have two blogs each; Joshua, 15, has one, plus two Xboxes. When Josh expressed an interest in building websites, his mom hired a graduate student to tutor him in coding.

Read the rest of this post on the original site »

Yes, it is perverse, but I really want to come in dead last in Time magazine’s “140 Best Twitter Feeds.”

Why? Well, there’s no way I am getting near the top with the likes of Sarah Palin and Lady Gaga in the same list, so I felt the 140th–get it?–slot on a Twitter poll is the next best thing to aim for.

Here’s the deal, according to the magazine’s Web site:

“TIME picks the 140 Twitter feeds that are shaping the conversation. Take a look and vote on whether you think these top tweeters should be on our list.”

The list is split up into categories, such as authors (Neil Gaiman, who is #1, and Margaret Atwood), celebrities (Gaga and the inevitable Justin Bieber) and companies (Zappos and Whole Foods).

There is also a technology group, with luminaries such as New York VC Fred Wilson, man-about-Web Kevin Rose and, of course, the King of Tweets Robert Scoble.

I am in that group too, with the description: “When this woman reports a rumor, you can pretty much count on it to be true.”

Thanks…I think–although I prefer to call it reporting a fact.

In any case, early on, I was doing badly in the voting–as I had hoped and is entirely correct considering I am unknown to anyone but certain geeks–and was right near the bottom with some suspect deal sites.

But by last night, GigaOm’s Om Malik had dropped below me, along with Wilson. I was at the unacceptable 131 spot.

This will not stand! Thus, so I can shoot the moon, I urge everyone to vote for:

132 Mike Allen
133 Om Malik
134 Amazon Deals
135 Fred Wilson
136 DealDivine
137 Nieman Lab
138 Best Buy Deals
139 Coupons.com
140 Steven Johnson

A well-known writer and entrepreneur, Johnson has 1.4 million followers on Twitter and does not deserve this ignominious loss as much as me.

Tweet that.

So why is the leading Twitter application–the one that many of Twitter’s most ardent users rely on–selling itself for $30 million?

That’s the question lots of people are mulling over since Friday’s news about the UberMedia/TweetDeck deal.

The tech investors and observers I’ve chatted with in the last couple of days generally land in one of two camps. Either:

• TweetDeck is the biggest Twitter client not owned by Twitter, and they sold too early.
• TweetDeck is the biggest Twitter client not owned by Twitter and, given the circumstances, they did okay.

This is basically a more muted replay of last year’s Twittersphere freakout, when it became clear that Twitter wanted to own much more of the Twitter ecosystem itself, and would place more limits on everyone else.

One important variable here is the way you view Bill Gross and UberMedia. A big chunk of the TweetDeck payout–the majority, according to multiple sources–will be in UberMedia stock. So if you think that company–which just raised another $17.5 million itself–has an upside, then the deal looks that much better.

That’s hard to figure, though, because Gross seems to be doing two things: Buying Twitter apps that compete with Twitter’s own products, and building a Twitter advertising system that will compete with the one Twitter is trying to build itself.

And Twitter doesn’t seem any more receptive to any of that now than it did 10 months ago. But Gross and his backers argue that they’re going to pull it off in a way that makes Uber become the Zynga to Twitter’s Facebook–a smaller company built on another bigger company’s platform, that makes both of them more valuable. So if they’re right…

Meantime, this seems like a good time to revisit Twitter investor Fred Wilson’s “inflection point” essay from last April.

That’s the one that precipitated much quaking among third-party Twitter developers and investors, with good reason: In part, it explained that Twitter would be buying or building “hole-filling” services, which meant there wouldn’t be much reason for many of the Twittersphere’s existing apps to exist.

A year later, though, it’s the second part of Wilson’s essay, where he calls on developers to build new apps and services that “create something entirely new on top of Twitter,” that seems more striking.

Because if Twitter really does end up being worth $10 billion or more, it seems like someone ought to be trying to do that. I’m not sure I’ve seen any, though.

Am I missing something? Feel free to weigh in below.

While lots of music services are still trying to figure out how to make money by distributing copyrighted music you’ve heard of, SoundCloud is taking a different tack. As I wrote last fall:

It’s designed to let professional and amateur musicians share their own music with each other and the public, via cloud-based files that the company hosts.

Once the tunes are on SoundCloud’s servers, the service makes it easy to move the stuff around the Web, via its own widget and an API that’s showing up on lots of interesting sites, apps, services and devices, including Facebook and Apple’s iPad. You can load SoundCloud files into Spotify, the streaming music company that Index has also invested in.

The service uses the freemium model, offering most of its capabilities for free, and charging up to $700 a year for more storage and extra features.

You can also use SoundCloud for less enlightened purposes, like sharing music you don’t own. But the company has recently implemented an audible “fingerprinting” service, like the ones Google’s YouTube uses, which allows copyright owners to take down files they don’t want on the Web. And that should give the company legal cover, unless the YouTube/Viacom case takes a very different turn.

In a blog post announcing the funding, SoundCloud says it will use the money to scale faster and “be more present in the US.” It also posts short clips, using its service, from its new investors–Index’s Mike Volpi and Union Square’s Fred Wilson.

Here’s Wilson:
Thoughts on SoundCloud by fredwilson. Uploaded with SoundCloud Android

And Volpi:
Mike Volpi Audio Blog on Friday morning by mvolpi. Uploaded with SoundCloud iPhone

And if you’d like something more entertaining, here’s a very long mix of classic hip-hop, via Cut Chemist:

Cut Chemist – Hip Hop Lives (1985-1996) by Cut Chemist

In one memorable episode of the famous old short films “The Little Rascals,” after not getting invited to a party, the Our Gang little dudes decided to form their own group, comically called “The He-Man Woman-Haters Club.”

In other words: No girls allowed!

While it was wink-wink cute when Spanky, Alfalfa and Buckwheat huffed and puffed about keeping out Darla–which they never ever could do–back in the last century, it’s not quite as adorkable when it comes to the boards of all the major Web 2.0 hotshots these days.

That would be Twitter, Facebook, Zynga, Groupon and Foursquare, none of which have any women as directors.

As in zero.

What’s most remarkable is that most of these start-ups are run by what I consider enlightened and open-minded entrepreneurs, mostly young enough to be part of a generation more inclined to value equality and diversity in the workplace.

In addition, each of these companies has a massive base of women consumers, in some cases well over 50 percent of its audience.

Thus, it would seem logical that in casting about for those to help guide these companies, one or two women leaders might slip in.

To be fair, it’s not for lack of trying, but of completion, as was the case with Twitter’s recent addition of three new board members.

They were longtime Silicon Valley exec Peter Currie, Flipboard CEO and co-founder Mike McCue and former DoubleClick leader David Rosenblatt.

All are deeply qualified for the Twitter board, which is obviously prepping for its next stage of growth and maturity.

But in its search, the San Francisco microblogging site did not manage to cast the net quite wide enough.

While sources said at least one prominent online woman exec was considered, there were some legitimate issues with her appointment, and it was not completed.

Still, one might imagine Twitter could have tried harder to find other workable choices.

Currently, the Twitter board is made up of the new trio, as well as Benchmark Capital’s Peter Fenton, Union Square Ventures’ Fred Wilson, Bijan Sabet of Spark Capital, CEO Dick Costolo and co-founders Evan Williams and Jack Dorsey.

Things are not any better over at Facebook, which has several prominent women execs running the show, most especially its high-profile COO Sheryl Sandberg.

But, inexplicably, though she does attend board meetings, she is not yet a director of Facebook, nor is any other woman.

In fact, here is Sandberg on topic at a recent TED event for women, in an eloquent speech titled “Why We Have So Few Women Leaders”:

Instead, the Facebook board is all men, all the time, composed of CEO and co-founder Mark Zuckerberg, prominent techie and venture capitalist Marc Andreessen, investor Peter Thiel, Accel Partners’ Jim Breyer and Washington Post head Don Graham.

It is no better at three of the most prominent recent Web 2.0 start-ups, which one source attributes to the lack of woman VCs, who are often the first board members after major investment rounds.

At Zynga, the hot social gaming company in San Francisco, it continues, with an all-male board, despite a very heavily female audience for its casual social games.

That would be co-founder and CEO Mark Pincus, COO Owen Van Natta, investor Bing Gordon of Kleiner Perkins, investor Reid Hoffman and Brad Feld of the Foundry Group.

The same is true at woman-targeted–spas, spas and more spas–social buying site Groupon, which has an unusually large board for a start-up and made up of–as per usual–all men.

The list: Co-founder and CEO Andrew Mason, Accel Partners’ Kevin Efrusy, former AT&T President and COO John Walter, New Enterprise Associates’ Harry Weller and Peter Barris, former AOL exec Ted Leonsis, 37Signals co-founder Jason Fried and early investors Eric Lefkofsky and Brad Keywell.

And, much smaller, is Foursquare’s board, which is the trio of co-founder and CEO Dennis Crowley, co-founder Naveen Selvadurai and Union Square Ventures’ Albert Wenger.

New investors–Ben Horowitz of Andreessen Horowitz and O’Reilly AlphaTech Ventures’ Bryce Roberts–have observer status and both are, needless to say, dudes.

There is no question it is tough to make sure there is a good balance of qualified women leaders to men in tech–it is an issue we wrestle with every single year for the program of speakers at our own All Things Digital conference, although we are most excellent on this issue on our Web site and conference staff.

But it can be done, especially at public tech companies. Google has two women on its board of nine directors; Yahoo has three of 10; even Oracle has two of a dozen.

But a grand total of zero at the leading companies of Web 2.0 is not just a coincidence.

It’s a shame.

Tomorrow, BoomTown will post a list of great women who would be superb directors for any of these companies, but until then, let’s not follow in Spanky’s steps:

Yesterday, star venture capitalist John Doerr of Kleiner Perkins forked over $150 million in funding to Twitter.

At at $3.7 billion valuation, that got him a big chunk of the San Francisco microblogging site.

But what it didn’t get him was a seat on the board of Twitter, which many figured he would be given for after handing over so much moolah.

According to sources familiar with the situation, that’s due to Doerr’s being a director on another board: Google.

Several sources who BoomTown spoke to, after breaking news of the massive funding, said that his being on the board of the search giant was seen as too much of a conflict of interest.

A conflict because Google has plans to wade deeply into the social space. And also, of course, because it is the No. 1 potential acquirer of Twitter, as the Silicon Valley company seeks to gather more tools to fight its latest rival, Facebook.

Doerr has very deep ties at Google, having been on its board since mid-1999.

He got that seat, along with Sequoia Capital’s Mike Moritz, after he ponied up a critical $25 million equity round for Google in June of that year.

Interestingly, no other Kleiner partner was named to a Twitter board seat either.

But, some speculate, it might make sense for Mary Meeker–who just joined Kleiner to head up digital investing efforts, after a long-time stint as a Wall Street analyst for Morgan Stanley–to eventually become a Twitter director.

Meeker has, of course, deep IPO and M&A experience.

And, frankly, after adding Flipboard’s Mike McCue and former DoubleClick exec David Rosenblatt yesterday and former Netscape exec Peter Currie recently to its all-boy board band, a woman director might be a good idea to consider.

Other directors at Twitter include Benchmark Capital’s Peter Fenton, Union Square Venture’s Fred Wilson, Bijan Sabet of Spark Capital, Co-founders Evan Williams and Jack Dorsey and CEO Dick Costolo.

I reached out to Doerr for a comment, but he has not yet replied; Twitter declined to comment.

Even more interesting to consider is what Kleiner will invest in next after this mega-funding, given how aggressively many sources said Doerr had pushed to lead the Twitter round.

And, in fact, sources said that Kleiner is looking closely at new funding rounds for both the Spotify music streaming service and Groupon, the social buying start-up that recently decided to turn down a $6 billion acquisition offer from Google and an earlier $3 billion one from Yahoo.

Groupon is now seeking more funds to remain independent and hold onto its lead in the fast-growing local discounting market, sources said.

(Bloomberg also reported on Groupon’s new fundraising efforts, although it was written about after it turned down the Google offer.)

And Spotify, which is hugely popular outside the U.S., is trying to enter this market, but needs more funding to expand and perhaps strike better deals with music labels.

Both are the just the kind of companies Doerr has targeted in what looks like a serious effort to compete with other firms–especially Andreessen Horowitz and Russia’s DST Global.

They have garnered the heat Kleiner used to have, largely by backing more of the top entrepreneurs recently.

Doerr has already put money into social gaming phenom Zynga and also started an sFund for social-focused investments.

Add Twitter to the pile and you can see where this is headed: Except for the board seat, John Doerr will no longer be denied.

According to sources close to the situation, well-known Silicon Valley power player Peter Currie is joining the board of directors of Twitter.

It’s an interesting choice to bring the well-regarded moneyman to the microblogging start-up, and could indicate an intent to push to an IPO eventually.

As first reported by NetworkEffect’s Liz Gannes earlier this week, Twitter is now considering funding offers from big venture funds, specifically Russia’s DST Global and Silicon Valley’s Kleiner Perkins, as well as fielding incoming acquisition interest from Google and Facebook.

Currie should know about this kind of noisy swirl around a hot start-up.

Back in the heyday of Web 1.0, as the CFO of Netscape Communications, he led the iconic browser software company into history, as the first great Internet rocket ship, when it went public on August 9, 1995.

While the Netscape experience ended in tears, Currie’s career has not, and he has become a kind of go-to elder statesman in the Web 2.0 era.

A year ago, for example, he joined Facebook as its temporary CFO.

That move came after the social networking site, in a bit of turmoil, parted ways with its then CFO, Gideon Yu, following mutual disagreements.

Indeed, Currie plays the calm, collected wise man well.

Unusually tall, aggressively avuncular and laid-back, he loves Elvis and enjoys pranking reporters like BoomTown.

(Case in point: Back in the day, he spread the rumor around Silicon Valley that I was short due to a medical condition.)

Now the president of Currie Capital, a private investment firm, he had previously worked at General Atlantic in private equity.

After Netscape, he was a partner and co-founder of the Barksdale Group, an early-stage (and ill-fated) venture capital firm.

Before Netscape, he was CFO of McCaw Cellular Communications and also worked at Morgan Stanley.

Currie is also board-happy, serving as a director of a variety of tech firms, private and public, which have had varying degrees of success.

They have included CNET, Critical Path, Clearwire, Safeco, Ofoto, Tellme Networks and Zantaz, as well as Sun Microsystems.

He has an MBA from Stanford University and went to Williams College.

In other words, just the kind of pedigree needed to give some additional burnish to the Twitter board, which now includes Fred Wilson of Union Square Ventures, Spark Capital’s Bijan Sabet, Benchmark Capital’s Peter Fenton, co-founder and former CEO Evan Williams, co-founder Jack Dorsey and CEO Dick Costolo.

Apparently, it’s time to toss another dude in there!

BoomTown has always enjoyed–although I have not always agreed with–the ruminations of Fred Wilson in his must-read blog, A VC.

Today, the New York venture investor–heard of Foursquare, Twitter?–penned one that was flatly on point, simply titled “Chasing Returns” about a potential crisis in start-up funding.

It was all due to a new class of investors too focused on chasing returns, noted Wilson, “and some of them do not understand what they are investing in.”

Rut-roh.

Perhaps dumb moneybags are not the greatest worry of our time–but dumber justifications of questionable success certainly should be, which Wilson also called out recently in an article in the New York Observer about the bubbly start-up scene there.

Said Wilson:

“It’s not all going great. You know, companies are failing. A couple of high-flying entrepreneurs came crashing to the ground recently. Justin Shaffer of Hot Potato and Sam Lessin of Drop.io–both of those companies essentially failed. Both of them ended up ‘selling’ their businesses to Facebook, but those were really just–Facebook wanted to hire those people, and they wrapped it up in a ‘sale.’ But those companies were unsuccessful. They failed. So there is failure out there–like, right in front of us. We can see it.”

Many quickly cried foul after Wilson’s remarks, but many more secretly shook their heads in agreement at the reality distortion field around entrepreneurs.

This has happened a lot lately in Silicon Valley, of course–as evidenced by a series of just-in-time saves of once high-flying start-ups (Slide being bought by Google comes to mind) sold as wins.

Indeed, painting failure as another form of success is one of the favorite and endearing canards of tech, showing an ability to bounce back from any negative and pivot into a new direction.

But most pivoting, as Loren Feldman of 1938 Media recently pointed out, is just another word for covering up misdirection.

Perhaps misdirection–as it should be in any world that thrives on innovation and entrepreneurial instincts–is all well and good, but it is only that way as long as it is identified as such when it occurs.

So, good for Wilson for truth-in-labeling when it comes to start-ups, investing and chasing returns these days.

Fortune.com’s Dan Primack reports that Sequoia is leading a round that will add “between $25 million and $30 million” in funding at a valuation “in the ballpark of $135 million.”

Someone familiar with the transaction tells me that Primack’s numbers are “not a bad guess.” And it’s possible the numbers will end up somewhere higher than his report. Another source tells me that the round will end up bringing in between $20 million and $30 million, at a pre-money valuation of $120 million. That would put Tumblr’s value at $140 million or more.

In any case, it’s a lot of money. And as wise Om Malik says, “Investors are never the story.” (Except when they are. And what’s really relevant here is that at these prices, the list of potential Tumblr acquirers gets much smaller: Google, sure. Facebook, perhaps. Yahoo, theoretically, etc.)

The real story for Tumblr remains the one we’ve asked every other time the company has raised money ($4.5 million in 2008; $5 million earlier this year): How’s it going to make money? Founder David Karp has offered several different ideas in the past, but as far as I can tell, none of them have really taken off (the fact that big publishers like Newsweek now maintain Tumblr sites, which are free to set up, does not constitute a business).

Best I can tell, the real appeal for Tumblr is its go-go growth, and the fact that it’s doing it on a very light footprint. But don’t take my word for it: Ask Spark Capital’s Bijan Sabet and Union Square Ventures’ Fred Wilson, who have been the primary investors in the company to date and who both wrote glowingly about the company in recent days.

Presumably, the company’s pitch to investors went something like this: “Look at our hockey stick! Hockey sticks like this only come around a few times a lifetime–perhaps you’ve heard of Twitter?” That is: Buy now, and we’ll figure out money later.

And it looks like it worked.

Big Web CEO/very recently CEO Interviews:

The headliners for the Web crowd were Eric Schmidt of Google on day one, Mark Zuckerberg of Facebook on day two and Evan Williams of Twitter on day three. None of the conversations were super revelatory, but they did highlight the heightening competitive tensions between Facebook and the rest of the Web.

Here’s the Zuckerberg video, which was notable for being one of his better public interviews in terms of ease and clarity (nothing like the near-fainting incident while being pummeled with privacy questions by Walt Mossberg and Kara Swisher at D8).

Two good comments from Web 2.0: About giving Google access to Facebook user email addresses, Zuckerberg said, “I’m not sure we’re 100 percent right on this.” (For someone with his hubris, that’s practically an admission of guilt.) Zuckerberg also criticized the visualization of the Web as a map of territories that illustrated the Web 2.0 stage.

“Your map is wrong,” he said. “The biggest part of the map has to be uncharted territory–this map makes it seem like it’s zero-sum, but it’s not. We’re building value, not just taking it away from someone else.”

Here are Schmidt (already at 170,000 views!) and Williams.

Best panel:

The most captivating panel was the one with venture capitalists John Doerr and Fred Wilson, ably moderated by John Heilemann. Wilson argued that Google has bought all of its recent interesting products, saying its last in-house success was Gmail. “They haven’t home-built from the ground up anything interesting in a half decade,” he said. Doerr replied passionately, “Ideas are easy. What’s really dear is execution. Google executes. Facebook executes.”

Best start-up presentation:

Brian Pokorny, CEO of DailyBooth, explained how the young people who use his site to share pictures are having conversations with each other. Pokorny made an interesting distinction about how–unlike with other photo-sharing apps–his users choose to use the front-facing camera on the iPhone and iPod Touch so they can take pictures of themselves.

An evening talk by agent Ari Emanuel was also quite well-received, with many people mentioning it to me the next day. You can watch it here.

Please see the disclosure about Facebook in my ethics
statement.

But Wilson doesn’t use the word “bubble” anywhere in the post he wrote this morning. Instead he refers to “storm clouds” in two markets: One for tech start-up financing, and one for tech workers themselves (courtesy Google, Facebook, et al).

These are ominous clouds! A few excerpts from his post:

• “The competition for “hot” deals is making people crazy and I am seeing many more unnatural acts from investors happening.”
• “We are also seeing large deals ($5mm to $15mm) getting done in a few days with little or no due diligence. Investors are showing up at the first meeting with term sheets. I have never seen phases like this end nicely.”
• “I think both of these situations are unsustainable. And anything that is unsustainable will eventually stop happening.”

On Twitter, I summarized Wilson’s post this way: “@fredwilson says yes, it’s bubbletime.” And then I heard immediately from Betaworks’ Andrew Weissman and O’Reilly AlphaTech Ventures’ Bryce Roberts, both of whom have invested with Wilson in the past: They don’t think Wilson means there’s a bubble.

And neither does Wilson himself:

Why does it matter if we describe something as a “bubble” instead of “troubling”? I’m not sure that it does for the layperson. But I think it’s very meaningful for professional investors like Wilson. For one thing, if they think it’s a bubble, then their own investors might wonder why they’re continuing to make bets.

It’s also worth noting that even if we are in a bubble, it’s nothing like the housing bubble, or the 2000-era Web bubble (when Wilson was making VC investments via Flatiron Partners): The scale isn’t remotely similar, and the general public has very little stake in the outcome.

But it’s Wilson’s post, so he gets the last word here. Here’s his response to an email I sent asking him for additional input (I’ve added a punctuation mark or two):

I don’t think it’s helpful to use the bubble framework. There is a supply demand imbalance in hot deals and sw engineers, particularly in Silicon Valley. That is driving up prices but also leading to some odd behavior. I just think it’s healthy to talk about it calmly and rationally.

[Image credit: Joi Ito]

With All Things Digital Global HQ located in the heart of the Castro in San Francisco, BoomTown tries hard not to judge–even that dude who likes to come into the Starbucks (SBUX) naked.

But I made an exception to be a judge for an innovative civic geek contest that New York City is doing for the second year called BigApps 2.0.

Get it? Big Apple…BigApps!

In any case, Mayor Michael Bloomberg is opening up a whole mess of government information–350 data sets from more than 40 agencies–and letting software developers have at it.

According to NYC:

“The City continues to open more data on the www.NYC.gov Data Mine as part of transparency initiative. The Data Mine was established for last year’s competition and, as part of the City’s efforts to promote transparency across agencies, all data will remain available for public use after the conclusion of the competition. Additional datasets will be made available throughout the year.”

Some of the new juicy data includes: CompStat data, buildings complaints and real-time traffic numbers.

The winners for the best apps created to help New York City citizens will get cash prizes totaling $20,000.

Last year, there were 84 apps, including a winner from Big Apple Ed, a guide to schools there.

The new winners will be announced in March of 2011, after fellow judges of mine–including Union Square Ventures’ Fred Wilson, Hunch CEO Chris Dixon and Betaworks CEO John Borthwick–decide who is the best.

And how much do you want to bet there will be a bed-bug app submitted this year?

Here’s the official press release from NYC:

MAYOR BLOOMBERG Launches NYC BIGAPPS 2.0 COMPETITION

More than 350 Datasets Provided by More than 40 City Agencies and Commissions, Doubling Last Year’s Availability

Competition Builds on Citywide Efforts to Increase Government Transparency and Provide Greater Public Access to City Data

Mayor Michael R. Bloomberg, Deputy Mayor for Economic Development Robert K. Steel and Deputy Mayor for Operations Stephen Goldsmith today launched NYC BigApps 2.0, the second annual contest for software developers and members of the public to create web or mobile applications using City data. Building upon the success of the inaugural NYC BigApps Competition launched in October 2009, the City has roughly doubled the number of datasets available, bringing the total to more than 350. These datasets provide developers and programmers with additional material, including public safety data, buildings complaints, and real-time traffic numbers from which to create new digital applications. Last year’s winning applications are today helping New Yorkers find mass transit routes, review public school information and gather an array of information based on their current location. This year’s winning applications will receive cash prizes totaling $20,000. Deputy Mayor Steel will detail the program this evening at NY Tech Meetup, a monthly meeting of tech entrepreneurs where companies and developers demonstrate new technologies. Deputy Mayor Steel will be joined at the announcement by New York City Economic Development Corporation President Seth W. Pinsky, Department of Information Technology and Telecommunications Commissioner Carole Post and Mayor’s Office of Media and Entertainment Commissioner Katherine Oliver.

“NYC BigApps combines two of our Administration’s important priorities: making civic information more readily available to New Yorkers and promoting innovation and entrepreneurship in New York City,” said Mayor Bloomberg. “The inaugural NYC BigApps competition yielded an array of creative uses for City data, and–with nearly twice as much data formatted for application use this year–there are even more possibilities with version 2.0.”

“The most important thing that the public sector can do to help create jobs through technology innovation is to provide our talented entrepreneurs with the tools to create new products,” said Deputy Mayor Steel. “The BigApps competition does this by providing open access to City Data. Through the competition, we encourage the development of applications that can then be commercialized, spurring job growth and economic development in New York City.”

“NYC BigApps is redefining the relationship between City agencies and enterprising citizens, all while delivering value to the public,” said Deputy Mayor Goldsmith. “Last year, NYC BigApps contestants came up with innovative applications that would have never been created in the normal course of business. There is more data available for use in this year’s competition, so the potential for new and innovative tools that can benefit New Yorkers is even greater.”

“Last year’s Big Apps competition was an enormously successful way to achieve multiple goals: supporting the City’s important technology sector, giving entrepreneurs opportunities to create new products, and increasing the accessibility and transparency of City government,” said New York City Economic Development Corporation President Pinsky. “This year’s expanded contest promises to promote even more innovation and creative thinking among the vibrant and growing tech community in New York. We look forward to seeing the results of their efforts.”

“NYC BigApps, and the DataMine site that supports it, sits at the heart of the City’s open data efforts,” said Department of Information Technology and Telecommunications Commissioner Post. “This effort complements the many other ways we’ve worked to bring technology to life for New Yorkers, including 311 Online and the 311 iPhone app. Beyond today’s competition, we’ll continue enhancing the functionality of DataMine and expanding the amount of data available there for use across the City and around the globe.”

“At the Mayor’s Office of Media and Entertainment, we’re exploring new ways to share information about City resources and services across multiple platforms,” said Commissioner Oliver. “Already we’ve reached new audiences through QR codes on the Staten Island Ferry and on the sides of sanitation trucks, and we’re making the content of our online Video On Demand player available on various mobile devices. The NYC BigApps Competition is the perfect opportunity to further communication between the government and the public.”

The NYC BigApps Competition is open to individuals, and companies and non-profit organizations with fewer than 50 employees. More than 160 datasets have been added to the 190 compiled for the inaugural competition. New York City Economic Development Corporation and the Department of Information Technology and Telecommunications coordinated with over 40 City agencies and commissions to provide the datasets, with 15 new City agencies, including the Department of Environmental Protection, the School Construction Authority and the Campaign Finance Board, participating in Data Mine for the first time. New data on public safety, the City budget, complaints to the Department of Buildings, and real-time traffic information will all be available for download today at www.nyc.gov/data .

The Data Mine was established for last year’s competition and, as part of the City’s efforts to promote transparency across agencies, all data will remain available for public use after the conclusion of the competition. Additional datasets will be made available throughout the year. Information and updates on the NYC BigApps competition, as well as official rules, can be accessed at the competition website: www.NYCBigApps.com .

Fourteen winners will be chosen in total, including two new prizes–best application created by a high school, college or full-time graduate school student; and a Large Organization Recognition Award for organizations with 50 or more employees, which will not eligible for a cash prize. A panel of judges from the technology and venture capital community will select winners for Best Overall Application (Grand Prize, Second Prize, Third Prize and five honorable mentions), Investor’s Choice Application, City Talent Award, Student Award, and the Large Organization Recognition Award. Two Popular Choice Application awards will be determined by public voting. Judging criteria will include the benefit to residents, visitors and City government; the quality and implementation of the idea; and potential commercial value.

All submissions are due on January 12, 2011. The Popular Choice Application winners will be selected by public vote through www.NYCBigApps.com between January 26 and February 26. Winners will be selected and announced at an awards ceremony to be held in March.

Last year’s winners included: WayFinder NYC–an application that allows users to find the nearest and best directions to New York City subway and New Jersey PATH stations; Taxihack–an application that allows users to post live comments on New York City taxis and their drivers via email (alert@taxihack.com) or Twitter (@taxihack); Big Apple Ed–an education application that provide residents with an easy-to-use guide to schools in the City, including school searches, top ten lists , analyses , comparison charts , and detailed school profiles ; and NYC Way–an iPhone application that bundles more than 30 New York City resources and provides information sorted by the user’s current location. The developer of NYC Way, MyCityWay, received the first investment by the NYC Entrepreneurial Fund, a $22 million seed and early-stage investment fund established by the City and managed by FirstMark Capital.

The judging panel is comprised of: Dawn Barber, Founder, Tech Meetup; John Borthwick, CEO, Betaworks; Chris Dixon, CEO & Co-founder, Hunch; Esther Dyson, Chairman, Edventure; Stuart Ellman, Co-Founder & General Partner, RRE Ventures; Lawrence Lenihan, Founder, CEO and Managing Director, FirstMark Capital; Danny Schultz, Co-founder & Managing Director, Draper Fisher Jurvetson Gotham Ventures; Naveen Selvadurai, Co-founder, Foursquare; Kara Swisher, Co-Executive Editor, AllThingsD.com; and Union Square Ventures Partner Fred Wilson.

“We are thrilled to be powering the second NYC BigApps competition, with significantly more data made available for software developers and the general public,” said ChallengePost Founder and CEO Brandon Kessler. “We were wowed by the creativity of the apps in the first competition, and we look forward to giving new entrants the great exposure they deserve.”

“New York is home to some of the world’s best developers,” said Foursquare Co-founder Naveen Selvadurai. “It is great to see the City rewarding this talent and taking advantage of it to increase transparency and make the wealth of information on NYC.gov more easily accessible.”

After the much anticipated news yesterday that Foursquare would finally grab a big piece of change from the powerful Silicon Valley venture firm Andreessen Horowitz–$20 million simoleons, in fact–BoomTown was much entertained by two very different blog post that went up about the deal.

The first was by one of the hot social location start-up’s early VCs, well-known New York investor Fred Wilson of Union Square Partners.

In a post on his blog A VC, titled “Some Thoughts on Foursquare,” Wilson disagreed with my assessment that the deal to fund the company–which included acquisition interest from Yahoo (YHOO) and Facebook–was “a very long and decidedly strange funding journey” and that it came “after a series of missteps and switchbacks over what’s next for Foursquare.”

His essential argument about what he thinks of as criticism on my part: Wrong!

Wrote Wilson:

“The conversations with potential acquirers were very beneficial to the founders and the company in many ways. It helped them to understand what the risks of going it alone were versus the risks of selling….And it allowed the founders to develop close working relationships with some of the most important Internet companies who can not only be acquirers but also distribution partners and monetization partners.”

Okay, I’ll bite. It’s all been a terrific learning experience for Foursquare’s young management team, especially its CEO, Dennis Crowley. Like college but without the tests and, instead of forking it out, you get handed a big pile of money at the end!

Plus you meet all these nice people along the way, who–even if they don’t scoop you up in a big acquisition hug today–are now super good pals who might also hand you a pile of money tomorrow.

Maybe so, but that does not mean they didn’t wince at the process they got drawn into.

Actually, from numerous interviews with all the players involved, even those who like Crowley and think there is something innovative at Foursquare, pretty much everyone thought the whole process a tad sloppy, a bit arrogant, a lot noisy and, perhaps most of all, gave everyone a little too much time to consider the many competitive challenges the company faced.

Does that matter? Probably not, as everyone in the Internet business is very much used to VCs and others treating entrepreneurs as delicate hothouse flowers who must be revered, coddled and indulged in their noble quest to bring us all kinds of cool stuff, such as the ability to check in from my garage.

And, of course, some of them deserve that attention and petting up and down, transforming into digital geese laying golden eggs for all.

But some definitely do not. Because for every Facebook, there is a plethora of not so successful companies that get quickly and copiously feted and then hit the inevitable wall.

Slide, run by an extraordinarily gifted entrepreneur, Max Levchin, is a good case in point. After its $50 million funding in early 2008, the company was valued at $550 million and seemed ready to take over the widget universe.

It was, if you recall, very hot.

But things cooled and Slide has since regrouped. It is now plugging away at the tough part of building its social entertainment business into a real business.

Perhaps not as hot, where the real heat is.

And, that’s the underlying point Microsoft (MSFT) Director of Social Engagements Mark Drapeau seemed to be making in his post, “It’s About Trust: Thoughts on Location-Based Services, Especially FourSquare.”

His premise: Who knows yet who is going to succeed in the geo-location space.

Wrote Drapeau:

“I don’t necessarily see why FourSquare or Gowalla or even Facebook will necessarily be the market leader. People generally speak of these three as if they’re predetermined….Deploying the app and making it cool isn’t the real challenge. Building trust among the user base is.”

While you can easily dismiss any complaint from a Microsoft dude–who even admitted to a frustrating experience of trying to reach Crowley to do a small deal–you still cannot ignore the simple idea that these fundings are all crapshoots a lot of the time.

Which is why I do agree with Wilson in a way about his bromide about taking time to deliberate big decisions:

“So the moral of this story, if you will, is don’t let conventional wisdom force you into making decisions you don’t need to make and you aren’t ready to make, particularly about very big decisions that you will be living with the rest of your life.”

Indeed, but let’s perhaps take it one step further:

Don’t let Silicon Valley conventional wisdom force you into making mountains out of molehills too early, particularly very big mountains that you will be waiting to form for the rest of your life.

The piece seems to have been primarily reported this winter, just as Chatroulette was becoming a phenomenon and shortly before Ternovsky lit out for the United States. If you’re interested in digital media investing, there are a few tasty tidbits, like Union Square Ventures partner Fred Wilson’s assistance in arranging a visa for Ternovskiy, and the programmer’s disdain for Digital Sky Technologies’ Yuri Milner.

And there’s a tiny bit about Chatroulette’s finances, at least as of a couple months ago: Since Google (GOOG) wouldn’t get cut him an AdWords check, Ternovsky’s sole source of revenue was Mamba, a Russian dating service. But that was enough: He was generating $1,500 in advertising a day, which he said covered his costs. Still, there’s not much in the way of “news” here.

But make a point of reading Julia Ioffe’s story, which paints a compelling portrait of Ternovsky’s Moscow childhood. It’s going to seem both familiar and alien to a lot of you.

He was born on April 22, 1992, less than four months after the collapse of the Soviet Union, and grew up in a tidy apartment in a typically dingy Moscow high-rise. His mother, Elena, is a talented mathematician who works on differential equations at the élite Moscow State University. His father, Vladimir, is an associate professor of mathematics at the same university, and dabbles in cybernetics. Their household was loving but turbulent. The couple fought and frequently separated, and Vladimir started a parallel family, an issue that was never openly discussed. (“It’s a little game we play,” Elena said of the arrangement.) Andrey retreated to his room, where, thanks to Vladimir’s belief that “the future would have something to do with computers,” there was always a machine, as up to date as the family could afford. Vladimir invested great effort in Andrey’s upbringing, engaging a Chinese tutor, a weight-lifting coach, and a chess teacher. But most of Andrey’s learning occurred alone, with his computer. He started with games, usually of the reality-simulating variety. By fourth grade, he was writing code.

Like many young Russians with programming skills, Ternovskiy turned to hacking. When he was eleven, he came upon zloy.org (which translates as angry.org), a hacker forum led by a young man named Sergey (a.k.a. Terminator), who trained his followers in cyber warfare. Using the handle Flashboy, Ternovskiy soon mastered the art of the denial-of-service attack, wherein a target system is paralyzed by a mass of incoming communication requests. Next came Web-site and e-mail hacking, a service he gladly performed for girls who asked nicely. By 2007, at the age of fifteen, Ternovskiy had learned about what hackers call “social engineering”–getting what one wants through deceit or manipulation. Posing as a teacher, Ternovskiy got access to some practice tests before they were delivered to his school.

You can, and should, read the rest here.

But don’t tell that to the TweetPhoto team. The San Diego-based photo service, which is indeed built around Twitter, has just raised $2.6 million, led by Canaan Partners, supported by Anthem Venture Partners and Qualcomm (QCOM).

The series A funding certainly seems a bit more fraught than it did about a week ago. Since then, Twitter appears to have decided on a build/buy strategy for some functions it previously allowed third-party developers to handle.

And if you believe that Twitter investor Fred Wilson’s “hole-filling” blog post is a road map, then Twitter is set to run its own photo service sooner than later.

If so, the money TweetPhoto just raised makes it unlikely that Twitter will buy the start-up because it’s now a much more expensive acquisition. And you can say the same thing about YFrog, the Sequoia-backed photo service whose parent company, ImageShack, has raised $11 million.

So if you follow that logic, Twitter will either buy TwitPic, which is the most popular Twitter-centric photo service (and one that hasn’t raised venture funding)–or build its own.

TweetPhoto CEO Sean Callahan says his service will survive whatever Twitter does because it can work well with other social networks, like Foursquare and Facebook. And Deepak Kamra, the Canaan partner leading the investment, says that his team knew Twitter would want to do more of this stuff on its own, and planned accordingly.

“I think there’s a lot of fear uncertainty and doubt for the next 6 months or so. Which also creates opportunity,” Kamra said.

But even if Twitter hadn’t roiled the waters last week, TweetPhoto–and all the other photo uploading services–wouldn’t have smooth sailing. All of the services boast big traffic, but it’s expensive to host all those photos, and it’s hard to sell ads against those pages.

Meanwhile, do you know which photo service you use to push pictures to Twitter? It turns I out I use TweetPhoto, because that’s the default photo service on both TweetDeck and SocialScope, my two primary Twitter platforms. But I had to look it up to find out.

Callahan says he can lure more developers and distribution because his API is more robust than his competitors. And he says his new funding will allow him to experiment with revenue models. One idea: Charge other publishers for the right to use his users’ images as stock photos.

I think that one poses a bunch of problems. For instance, what do you do with the weird images I’ve uploaded?

But Callahan says he now has time to figure it out. “We’re going to throw a bunch of stuff against the wall and see what sticks,” he says. “That was the purpose of doing the series A.”

4.13.2010 — San Diego, CA – TweetPhoto (http://tweetphoto.com), the real-time media sharing platform for the social web, today announced it has secured $2.6 million in a Series A financing led by Canaan Partners, with additional investment from Anthem Venture Partners and angel investors. The company plans to use the capital to accelerate the development of its core offering, a platform of open APIs and mobile SDKs for real-time media sharing across the social web. The round will also allow the company to expand its developer relations program and to introduce new products that further strengthen its position as the preferred way for leading application developers to incorporate real-time media sharing into their applications.

“We are extremely pleased that we have been able to assemble a great syndicate of investors to help us in the next phase of our growth,” said Sean Callahan, CEO of TweetPhoto. “This round of funding will allow us to further attract top engineering and sales talent while we continue to focus on delivering the best platform available to instantly share media anywhere from any device. In the next few months, we will significantly expand our offerings and make it easier for developers to create compelling applications that leverage the social web.”

TweetPhoto allows users to share, discover, and interact with media seamlessly across multiple social networks through its developer platform. TweetPhoto users can link their accounts and publish media instantly to Twitter, Facebook, Foursquare, LinkedIn, and other popular social networks, and the TweetPhoto APIs support features such as photo commenting, favoriting and voting, meta-data filters, geo-tagging, location-based search, friend feeds and customizable widgets. These features are exposed through a rich suite of easy-to-implement APIs and software libraries that let application developers easily incorporate these best-in-class media sharing capabilities into their mobile or web applications.

“Consumer demand for intuitive, effective and easy to use media sharing technology continues to increase,” said Deepak Kamra, General Partner at Canaan Partners. “The number of people connecting through social networking sites and the social web is still growing, and sharing rich, personalized content is a key part of the experience. We’re excited to leverage our investment history and experience in the social media industry to help TweetPhoto expand its offerings and achieve a new level of growth.”

“Sean and his team have built a solution that provides a simple and elegant way for developers to create more engaging, connected applications,” said Brian Mesic, General Partner at Anthem Venture Partners. “The company has great traction, and the platform has proven to be scalable and robust through a period of truly impressive growth.”

One year after launching the service, TweetPhoto has attracted a dedicated team of developer-friendly engineers and key sales executives serving nearly 15 million monthly unique visitors from various social networks, 40 million API requests a day and 250 million images each month.