As we reported last September, Xobni rebranded its email contact manager Smartr and launched Android and Gmail apps out of private beta. Today, Xobni is debuting the iPhone version of Smartr.

The Smartr Cloud automatically extracts all contacts from your iPhone’s email data (currently integrated with Outlook or Gmail), as well as data from social networks, and makes them easily searchable. A complete profile is created for each contact, including a photo, job title, phone numbers, company details, email history, common contacts and info from Facebook, LinkedIn and Twitter.

All contacts are ranked by importance, not alphabetically, so the most important people are at the top. Different tabs show you contact details, that contact’s recent social feeds, your relationship history, and other contacts you share in common. The Gmail add-on shows you contextual information about whoever is sending you an email culled from various social networks (Facebook, Twitter, LinkedIn) and company databases. It also shows you your relationship history with that contact, a list of pervious email conversations and related contacts, as well as contact search.

As Xobni explains, these rich profiles help you better understand your relationship with each contact, how you know them, when you last communicated, and whom you know in common.

Last year, we wrote about email software company Xobni’s survey that showed that going completely offline from email over the holidays is a thing of the past. And this year’s survey from Xobni reports that even more adults will be checking email over the holidays.

According to the survey 79 percent of U.S. working adults have received work-related emails on the holidays; and 68 percent plan to check emails during Thanksgiving, Christmas, etc.

Of these, more than one in four (27%) do so multiple times throughout the day (that will be me). Additionally, a comparison with last year’s survey results shows that men are checking email less than they were last year (58% in 2011 vs 67% in 2010) and that the gender gap is closing with respect to checking email on holidays. Last year, 67 percent of men admitted to checking on holidays and 50 percent of women compared to 58 percent men and 51 percent women in 2011.

And less people (37 percent) feel annoyed, frustrated or resentful after receiving work-related emails on holidays than last year. Many people welcome email during family time with 19 percent of those that ever received work emails from a colleague while off for the holiday cited feeling “thankful for the distraction” or “relieved.”

Forty-one percent of those that check work email while they have time off for the holidays believe that staying up-to-date on email eases their workloads once they return from break.

One in ten (10 percent) of respondents ages 18-44 stated that they did so while spending time with friends or relatives at Holiday parties/gatherings or during meals or another “inappropriate” time. Better yet, some (6 percent) admitted to using work email as a way to avoid awkward family/holiday commitments and ”crazy” friends and/or relatives.

Photo Credit/Flickr/StereroGab

Xobni’s social email plugins essentially makes your e-mail smarter (Xobni is inbox spelled backwards). The plugin integrates LinkedIn, Twitter Yahoo Mail, Facebook, Skype, Hoovers and more into your Outlook inbox. The company, which has raised over $30 million in funding, also recently debuted a plugin for Gmail as well as iPhone and Android apps. To date, Xobni’s Mirosoft Outlook plugin has seen nearly seven million downloads.

The Gadget Store allows users to access free and paid apps for productivity apps and services from within Xobni for Outlook, enabling developers to integrate their services seamlessly into Outlook’s email workflow. Related to this, the company launched a feature last year that allowed users to integrate Gmail Gadgets within Outlook.

Gadgets are included as part of the Xobni sidebar, and users can choose from nearly 20 services and applications for web-based document sharing, lead tracking, issue reporting and monitoring, note-taking, and more. Current Xobni gadgets include Dropbox, Evernote, GoldMail, Google Translate, Atlassian JIRA, WebEx, Huddle, Microsoft SharePoint, Salesforce Chatter, Yammer, Facebook, Flickr, Hoover’s, Klout, LinkedIn, Twitter, Xing, YouTube, Yelp and Salesforce CRM.

For example, you can add the Evernote gadget to Xobni to allow users to access their notes directly from the inbox. Or you could access data from your Salesforce CRM or Chatter account within your Xobni Outlook inbox.

While the Gadget Store is exclusive to the Xobni’s Outlook version, it will eventually extend to the Gmail plugin.

Ever since Xobni launched at the first TechCrunch 40, it’s been about Outlook and then Blackberry. But those of us who use Gmail also want to make our inboxes smarter. Today, Xobni is launching aprivate beta for Gmail, and will soon also launch iPhone and Android apps. The first 100 readers to sign up for the Gmail beta will get in (use the code XOBNI-TC100).

The Gmail app comes in the form of a browser extension for either Chrome or Firefox (Safari and IE will come later). Once you install it, a Xobni sidebar appears in your Gmail Inbox. Once you allow it to index your contacts and hook it up to your Twitter, Facebook, and LinkedIn accounts, it starts to show you all sorts of relationship data. Contact search in the Xobni box is hella fast, much faster than searching in the Gmail search box (but only for contacts, it does not index the entire text of your messages).

When you open up an email, the Xobni sidebar shows you a graph plotting your relationship history (how many messages you’ve exchanged) as well as other contacts frequently CCed on messages to or from that person. You can also tab through to a list of recent emails with that person, summary info from their LinkedIn, Facebook, and Twitter profiles (along with recent status updates and Tweets).

Soon, the Xobni extension will work inline in the regular Gmail search box as well, creating smart autosuggestions every time you search. Other additional features the company is working on include contact suggestions in the To: field based on related contacts in the past, phone number extraction and attachment search . It will also pull Tweets and Facebook updates from your closest email contacts in a dashboard view, whether or not you follow them on those social networks.

Editor’s note: The following guest post was written by Justin Kan, founder of Justin.tv.

Right now I’m neck deep in product launch mode, putting the finishing touches on our new mobile video application—Socialcam. Of course, I’ve been here before . . .

Years ago when we launched the Justin.tv show we had no idea what we were doing. This much was obvious to anyone who watched. Outsiders attribute far more strategic thought to the venture than we gave it. Some think that we planned all along to start a live platform, and that the Justin.tv show itself was a way of promoting that platform. While this ended up happening, none of it had crossed our minds at the time.

Emmett Shear and I had been working on Kiko, the first Javascript web calendaring application in the Microsoft Outlook style. We prototyped the application in our final year at Yale, went on to raise money from Y Combinator, then continued working on it for over a year.

Then Google Calendar was released—boom—absorbing most of our nascent user base and capturing most of the early adopter mindshare. But to be perfectly honest, Kiko would have failed regardless. We were too easily distracted and hadn’t really thought through the strategic implications of owning a standalone calendaring property (hint: no one wants a calendar without email). A short time later we were burned out and spending most of our time playing Xbox with the Reddit guys in Davis Square—hardly a startup success story.

Emmett and I started thinking about possible ways to get out of the calendar business. At the same time, I was startup fatigued. We had spent over a year paying ourselves nothing. The seed and angel investment market conditions were the polar opposite of what they are today. It had been a struggle to even raise a paltry $70,000, and we had failed to build a product with real traction. I was starting to think about moving back to Seattle to try something new, maybe in a different industry.

Still, we learned a ton and it was fun to be part of the early Y Combinator startup community (then largely in Boston). We became friends with Matt Brezina and Adam Smith (of Xobni), Trip Adler, Tikhon Bernstam and Jared Friedman (of Scribd), and many others. It’s amazing to see how many of those friendships persist today, and even more amazing how well many of those companies are doing.

Coming back from one particular YC dinner, Emmett and I were discussing strategic ideas for Kiko, and I remember telling Emmett an idea that popped into my head: what if you could hear an audio feed on the web of our discussion? Wouldn’t that be interesting to other like-minded entrepreneurial types? We kept going, and eventually the idea morphed into a video feed. Then it became a live video feed. Then it became a continuous live video feed that followed someone around 24/7. Then it had chat, and a community built around watching this live show, which was now a new form of entertainment. I was hooked.

I couldn’t stop talking about the idea. I mentioned it at YC dinners and to other friends. I even came up with a perfect name for it: Justin.tv. On one trip to DC, I told my Dad and my college friend Michael Seibel what I was thinking. Eventually, in-between drinking sessions, we thought of a brilliant idea for divesting ourselves of Kiko, which is a story for another day. After that, Emmett and I were coming up with other startup ideas (I guess we got excited about staying in the industry after all). One particular favorite was the idea of a web app that would ingest your blog’s RSS feed and then allow you to layout and print physical magazines from it. Excitedly, we drove one afternoon to Paul Graham’s house to pitch it.

We explained the idea to Paul and Robert Morris, who just happened to be at the house visiting. I vaguely recall there also being a “this will kill academic publishing” angle, although I can’t figure out how that sensibly fits in now. Paul didn’t particularly like the idea: he didn’t think people would use it. “Well,” he said, “what else do you have?”

I said the only thing I could think of: “Justin.tv.”

Because it was something I was clearly passionate about, and because creating a new form of entertainment was clearly a big market (if you could invent one!), Paul was actually into it. Robert’s addition to the conversation was “I’ll fund that just to see you make a fool of yourself.” Emmett and I walked out of there with a check for $50,000.

Six months later, we’d recruited two other cofounders (Kyle Vogt, our hardware hacker, who we convinced to drop out of MIT on a temporary leave of absence, and Michael Seibel, my college friend from DC, who became our “producer”). We built a site with a video player and chat and two prototype cameras that captured, encoded and streamed live video over cell data networks, negotiated with a CDN to carry our live video traffic, and raised an additional couple hundred thousand dollars. Our plan? Launch the show and see what happens.

Now, let me just tell you why this was a bad idea:

• We didn’t have a plan. We loosely figured if the show became popular we could sell sponsorships or advertising, but we didn’t have a plan to scale the number of shows, nor did we understand what our marginal costs on streaming, customer acquisition, or actually selling ads were.
• We didn’t understand the industry. We didn’t know what kinds of content advertisers would pay for. We didn’t have good insight into what kind of content people wanted to watch, either.
• We relied on proprietary hardware that we were going to mass-produce ourselves. Smart angels told us to drop the hardware and figure out how to do it with commodity equipment, but we wouldn’t listen because we thought hardware would be easy (or at least, doable). Ironically, months after we were told this we switched to using a laptop.
• We were trying to build a “hits” based business without any experience making hits. We knew a lot about websites, but little about content creation. Smart VCs (who took our calls because Paul referred us) told us as much: nobody really likes investing in hits based businesses, because it requires the continual generation of new hits to be successful (instead of, say, building a platform like eBay or Google whose success is built on masses of regular users).

How did we get as far as we did?

• We were passionate. We honestly believed we could create a new form of reality entertainment. Put to the side that we had no experience with creating video (or any kind of content), by God, we were going to make this work.
• Early stage investing is often about the people, not the idea. Paul has said as much about what he looks for. As two-time YC founders he knew that we worked well together and even if we were working on something totally inane we were going to stick it out with the company and iterate until we found a business model.
• We sold the shit out of it. Everyone we knew was excited for Justin.tv. Why? Because our excitement was infectious. That’s how we got Kyle to drop out of school. That’s how we got Michael to quit his job and move across the country.

Ultimately, the show failed. But all told, I’m thankful every day that things went the way they did. Why?

• We built a strong team. The four of us started, and the four of us all still have leadership roles in the company. Along the way we recruited the smartest engineers and best product designers we could find.
• We were willing to learn, and to pivot. After quickly realizing the initial show wasn’t a sustainable model, we decided to go the platform route, and built the world’s largest live video platform (both on the web and in our mobile apps, which have millions of downloads).
• It got us started. Some people wait until the stars are aligned before they jump in. Maybe that’s the right move, but plenty of businesses get started with something that seems implausible, stupid, or not-a-real-business but turn into something of value (think Groupon). If we hadn’t started then, would we have later?

Today, I’m more excited about Justin.tv than I’ve been at any time since we launched the initial platform. Why? We’re taking everything we’ve gathered and learned over the past four and half years building the largest live video platform on the Web (17 million monthly unique visitors in Dec according to comScore’s MediaMetrix), and applying it to tackle a new generation of problems in mobile video. Our world class web and mobile engineering team, all of our product development knowledge, our substantial, scaled video infrastructure, and everything we’ve learned about building engineering teams has all been put to work on a new app that we think is going to change everything.

Our new app is called Socialcam, but that’s another story.

Photo by Terry Chay

Of the survey respondents over half (55%) check work email at least once a day and more than one in four (28%) do so multiple times throughout the day. The data also showed that 79 percent of those that check email while on holiday stated that they have received a work-related email from a colleague or client on holidays.

So are U.S. worker happy about the onslaught of email over the holidays? According to the survey, 15 percent are “thankful” or “relieved” to have the distraction of work email over the holidays. On the other hand, 41 percent of those that receive an email from a co-worker/client while they had time off for the holidays saying they are either annoyed, frustrated or resentful after receiving these emails. The survey also found that 12 percent of respondents actually “dread” seeing work emails populate their inbox and 10 percent even feel pity for those who do send work-related emails on holidays.

Regardless of how the actually feel about work email over a holiday, 42 percent of those that check work email while they have time off for the holidays still believe that staying up-to-date on email eases their workloads once they return from break. Some respondents (19 percent percent) that receive work emails from a co-worker/client while they had time off for the holidays say they feel “thankful” or “relieved” at having the distraction.

So what about the breakdown when it comes to males vs. females? Xobni says that
employed males are significantly more likely to check work email on holidays – 67 percent – compared to just 50 percent of women. Employed middle-aged adults feel the greatest urge, with 65 percent of those aged 35-44 stating that they have checked work emails on holidays.

One in ten (10 percent) who admitted to checking email while off for a holiday stated that they did so while spending time with friends or relatives at Holiday parties/gatherings or during meals. A small amount of those (5%) that check work email while they have time off for the holidays even admitted to using work email as excuse to avoid awkward family moments and other holiday commitments.

Photo Credit/Flickr/StereroGab

A new study by email software purveyor Xobni confirms what we bloggers know to be true, there’s actually no such thing as a day off in the Internet age (Want more visceral proof than an email study? Check out the timestamp of this post).

Information anxiety has pretty much put the kibosh on “time off” as two out of three Americans and Brits check their email outside of regular business hours (ha) and half of Americans email while on vacation (double ha).

The Xobni study, an online survey of 2,200 British and American adults conducted in August, holds that the traditional 9-5 work day has gone the way of the Dodo, due to the fact that Americans and Brits can’t stop checking their email. Apparently we sneak a peak at our inboxes while on vacation, weekends, sick days and even when we are (gasp!) in bed.

The press release blames this behavior on the down economy and the iPhone, but I blame it on the fact that we now live most of our lives online, and we feel compelled to check our email/Facebook/Twitter because that’s where most of the exciting stuff is happening anyways.

More highlights from the study/the life we have chosen:

* The 9-5 work day has gone the way of the Dodo. 72% of Americans and 68% of Brits say they regularly check their email on vacations, sick days, and at home in bed.

* Yes, IN BED. Conveniently for Xobni, work email in bed is apparently, you know, like a thing, with 1 in 5 Americans checking email as the first thing they do in the morning or the last thing they do at night before falling asleep (Again I can personally vouch for this).

According to Xobni, email has become an addiction, and like most addictions it is fueled by peer pressure:

* 27% check email outside of regular working hours because they feel it is expected.

* 26% of Americans feel they can’t handle/overwhelmed by the number of emails they receive during vacation.

Everyone in the world agrees that managing email has become a challenge to our sanity. And various companies are scrambling towards solutions including Google with its recent Gmail Priority Inbox launch and Xobni, obviously. My favorite low-fi way to deal with the bottleneck is a service called Sentenc.es which makes it clear to your email reader that you are limited to short responses.

Even though I’m not sure how well that will work, in bed.

Video, vaguely related.

Email overload image above: Ario_

Back in June, Xobni co-founder Adam Smith wrote a blog post announcing he was moving on from the company, and handing over the CTO reins. We’ve just confirmed that fellow co-founder Matt Brezina has also left the company.

The timing of Brezina’s departure isn’t fully clear, but we hear it was also a few weeks ago — he just didn’t have the big blog post about it. Obviously, having both co-founders leave so closely to one another is a bit odd. It was only this past April that they raised a large $16.2 million Series C round led by Khosla Ventures and RRE Ventures. Talk was that this put their post-money valuation at around $65 million. The company also recently moved into a new office in the SoMa area of San Francisco (Twitter’s old offices, actually) and crazy mural spending aside, it would seem that things were fine on the surface.

But before we confirmed the Brezina news, we had been hearing whispers of growing discontent within Xobni. The direction of the company and current management was cited as being two issues of concern in particular.

Initially a Y Combinator company, Xobni launched at the first TC40 conference in 2007. In 2008, the company was about to be acquired by Microsoft for something in the $20 million-range (they had only raised about $5 million at the time) but they walked away at the last second. At the time, they were focused on improving Microsoft Outlook, but they’ve since taken their tools to everything from BlackBerry to Gmail.

Update: I’ve now spoken with Brezina who confirms his exit but says it’s only because they’ve hired good people to run the company — of course, they always tend to say things like that, and in fact, Smith said the same thing. That said, Brezina did confirm that he and Smith are still on the board and involved.

As for what’s next, Brezina is working on it. Stay tuned.

In accordance with the “Go big or go home” model, Xobni’s description of the mural project, which was undertaken in Twitter’s old office, is extremely detailed. If the Dr. Seuss references don’t set off the bubble alert I don’t know what will:

1) We were looking for a Seuss-ian feel to bring the sense of wonderment to our office (growing up in the 60′s/70′s/80′s leaves us all with a soft spot for Dr. Seuss).

2) We wanted to have a little fun with some popular Internet clichés and sensations over the years – i.e. “series of tubes” (Thank you former Senator Ted Stevens, formerly head of committee to regulate the Internet).

Xobni, which just raised $16.2 million in series C funding (32.1 million total), has been looking for ways to make money over the past year, most notably going retro and serving up their email management software Xobni Plus in boxed form a la Microsoft Office. Perhaps they’ve never heard of the well worn aphorism “spend less than you earn”?

I’ve contacted Xobni for details on how much exactly the mural (by San Francisco-based artist Jim Winters) cost, and will post updates when I hear back.

Update: Xobni’s Terra Carmichael responds, “Can’t say how much it cost, but will say it’s nice to have creative friends.”

“The Making Of” video, below:

Photo: Xobni

Xobni is hoping to capitalize on some of the foot traffic that Microsoft will be bringing to stores for the new version of Office. Office is carried in 35,000 brick and mortar stores, and Xobni says that its software is currently in 10% of those stores, and will be adding its offering to more stores soon. The price for the boxed set will be the same as it is online: a one time fee of $29.95.

So why is Xobni going old school with software in brick and mortar stores? The company claims that retail boxes improve conversion online (60% of customers that Xobni surveyed say they are more likely to buy software online if they saw the software in a retail store) And 80% of people surveyed (over 2000 respondents) said they were likely or very likely to buy software in a retail store in the next year. Xobni also says that retail boxed software has a higher perceived value/price point.

Xobni’s social email plugin essentially makes your e-mail smarter (Xobni is inbox spelled backwards) and integrates LinkedIn, Twitter Yahoo Mail, Facebook, Skype, Hoovers and more into your Outlook inbox. The Plus product improves search in this plugin, and includes an autosuggest feature, which can use linked Facebook and LinkedIn accounts to pair Email address with full names, as well as the ability to search within your Xobni ‘feeds’ in the sidebar.

Xobni, which just raised $16.2 million in new funding, has been looking for ways to make money over the past year. Plus is one of these revenue streams, and Xobni also offers a paid syncing service between devices and desktop clients called Xobni One.

Of course, the offering of Plus in retail stores is more than just a revenue opportunity for Xobni. It’s also a branding opportunity to associate its product with Microsoft to consumers. While this move doesn’t represent an established partnership with Microsoft, Xobni is clearly hoping to ride on Office 2010′s coattails.

I promised myself to check out their product extensively over the weekend, and now that I did I’m seriously glad to have discovered them as their free software has already made my Gmail experience much better.

Rapportive is like Xobni for Gmail. It is a browser plugin for Chrome and Firefox that automatically adds a dynamic widget in the form a sidebar to incoming Gmail messages. Thanks to the extension, you’ll get a much better overview of who’s sending you emails, as the name and email address of the people who do will be automatically cross-checked for publicly available social network presences, pictures and more on the Web, all of which get displayed alongside messages.

The sidebar replaces Google’s contextual ads, so that’s a double win, unless you can’t live without advertisements in your Gmail – or if you’re Google.

As you can see in the screenshot below, Vohra recently got an email from Spark Capital’s Bijan Sabet and can immediately see what the man looks like in real life, in combination with links to his Twitter, Flickr, Facebook, MySpace, LinkedIn and other social network profiles. At the bottom, he can add a note about Sabet, turning the extension into a basic CRM tool as he’ll see those private notes every time he gets an email from him in the future.

Last week, the startup opened up to developers who would like to enhance the sidebar even more. Dubbed Raplets, these extra extensions effectively turn Gmail into a platform, enabling third parties to plug in free or paid CRM tools, social media monitoring applications, accounting software programs and more. One integration that is already in place is with our own CrunchBase, making it easier and faster to look up information about people and companies who can be found in the online database, which is growing quickly.

The startup promises to expand its service to other email platforms in the near future. Even if it’s only half as good as the plugin for Gmail, you’ll want to install it straight away.

Definitely a keeper.

For alternatives, check out Etacts and the more business-focused Appirio.

Xobni’s social email plugins essentially makes your e-mail smarter (Xobni is inbox spelled backwards). The plugin integrates LinkedIn, Twitter Yahoo Mail, Facebook, Skype, Hoovers and more into your Outlook inbox. CEO Jeff Bonforte tells us the plugin has seen 5 million downloads to date.

The round was an insider round and Bonforte seemed pleased that inside investors were fighting over who would lead the round. He says he’s happy with the valuation but declined to give us a number. The funding will be used for further product development, more mobile apps, and expansion of the plugin into other email platforms besides Outlook.

Xobni, which took an investment from the Blackberry Partners Fund last year, recently launched a Blackberry app that ranks your contacts by importance and pulls in social data from Facebook, LinkedIn and other places.

Along with the Blackberry app, Xobni also launched another product, Xobni One, that syncs your Xobni contacts in Outlook with your contacts on your Blackberry, all in the cloud. Xobni One is a way to sync your desktop and mobile contacts. If you use Outlook on your desktop at work, but Gmail on your Blackberry, Xobni One reconciles the two. Xobni is charging users for this service, which is just one of many revenue streams for the company.

It took almost a year, but Xobni finally released its email app for the Blackberry. It works as a standalone app integrated with the email on your Blackberry, but similar to Xobni’s Outlook plugin, it ranks your contacts by importance and pulls in social data from Facebook, LinkedIn and other places.

Along with the Blackberry app, Xobni is introducing another product which may turn out to be more important in the long run. It is called Xobni One, and it syncs your Xobni contacts in Outlook with your contacts on your Blackberry, all in the cloud. As Xobni rolls out more apps in the future, Xobni One should be able to sync contacts across those as well (very Mesh-like).

Xobni One is a way to sync your desktop and mobile contacts. If you use Outlook on your desktop at work, but Gmail on your Blackberry, Xobni One reconciles the two. And when you leave your job, your contacts stay with you. Xobni One isn’t free. It costs $4 a month or $40 a year, bundled with the Blackberry app. Keeping your contacts in sync is expensive. Doesn’t it seem that Google or Microsoft will eventually just do this for free?

As we first reported on Friday, Microsoft is adding some social hooks into Outlook 2010. Outlook will gain the ability to pull in profile information, photos, and update streams from LinkedIn, Facebook, and MySpace. You can try the LinkedIn plugin now in beta. The other social networks will be added later when Outlook 2010 goes on sale, probably in July.

The new social features make it look a lot more like Xobni, the social email startup backed by Vinod Khosla that Microsoft looked at buying nearly two years ago. Well, a poor man’s Xobni. With Xobni, which itself is a plugin for Outlook, you can pull in relevant contact information, photos, and social stream data from both LinkedIn and Facebook today. It also supports Twitter, and Hoover’s information on companies. Salesforce integration is currently in beta, and SharePoint is coming soon.

The idea behind bringing social streams into Outlook is that as you are reading or composing an email, you can see recent status updates or pictures of the person you are corresponding with to give you some instant context. The Outlook plugins are built on top its “Social Connector,” and was previewed last year. The Social Connector was really created for Microsoft SharePoint, which supports corporate profiles and file sharing. Getting the major social networks to write their own plugins directly for the Social Connector means that Outlook can support additional social streams down the road.

The bigger issue is that the Social Connector will only work on Outlook 2010, whereas Xobni works on every version going back to Outlook 2003. Correction: Social Connector works with past versions of Outlook as well. Companies tend to replace Outlook at a glacial pace, but it is clear that Microsoft is trying to make Xobni a feature of Outlook. And it only took two years to announce. And even now, many of the comments on Microsot’s blog post are complaining that the beta is crashing their computers. Some examples:

SocialConnector.dll crashes my 32-bit Outlook 2010 beta on Win 7 64 bit.

After installing this, Outlook will no longer start up. I’ve have removed the connector, but it still crashes outlook, not the computer. I’m using 64bit Win 7 Ultimate, with 32bit Office 2010.

Xobni could still be doomed, but it does have a few things going for it. The plugin has been downloaded more than 4 million times, its users are rabidly loyal, and the company will eventually expand to other email systems beyond Outlook. It also does email search a lot better (at least right now) than Outlook and can resolve different identities to the same person in your contacts list.

Most people don’t sign up for Facebook or even LinkedIn with their corporate Outlook email accounts. If the email addresses of your contacts in Outlook don’t match their email on LinkedIn, Facebook, or MySpace, you won’t be able to see their profile information or stream data using the Outlook Social Connector. Xobni does a better job resolving the multiple identities people choose to have on the Internet. That doesn’t mean the folks at Xobni should be breathing easy. Microsoft has endless patience and eventually it gets things right.

Update: Brad Feld finds another flaw with the LinkedIn Outlook plugin—it duplicates his contacts

Here are a few of the bigger UI changes: As you can see in the screenshot, there’s a new set of horizontal tabs to better filter content. Xobni is also now surfacing links exchanged between contacts for the first time — previously, there was just a way to do this for files exchanged. Also new, the Twitter extension element now includes a direct message (DM) option. LinkedIn support has been improved, as has some of the analytics.

There are a half dozen or so other enhancements to the client such as extensions now being resizable, and better drag and drop support. There’s also finally a way for users to easily open a folder that emails reside in. Basically, if you’re addicted to Xobni, there’s a lot of little tweaks (and some bigger ones) to try out.

But again, the big news is that Xobni is opening premium extensions to users — and not just business users, all Xobni users. If Xobni is able to effectively convince users to buy these (as well as get more beyond just Salesforce), it could be a decent new revenue stream for the company. Back in July, the company introduced ‘Xobni Plus’, the premium version of their product. Revenue streams can be addicting when turned on, it seems.

Earlier tonight, Xobni quietly released, at least to some users, a new version of its Outlook plug-in that brings Twitter streams into your email in an intelligent way. Instead of acting like any other Twitter client and showing you the full stream of everyone you follow, it shows you only the recent Tweets of the person whose email you are reading, whether or not you follow them on Twitter. (A Xobni blog post went up briefly about it and then was taken down, but not before I was able to grab the screenshot at right).

Instead of replicating Twitter outright, it shows you the Tweets in the context of an email to help you learn more about the person with whom you are communicating. This is consistent with the way Xobni brings up similar information about a contact from Facebook or LinkedIn or Skype. If you don’t know the person, it gives you some more context. If you do, it gives you something personal to talk about. (Threadsy, which launched at this year’s TC50, also shows Tweets in context alongside emails).

With both the full Facebook stream and now Twitter built into the product, chances are you’ll see what each contact has been doing recently. Xobni also lets you reply via Twitter, and follow a contact from within its application.

One of Xobni’s investors is Vinod Khosla, who told me a few weeks ago that Xobni is getting “great traction.” I’ve since heard that the product is approaching 3 million downloads.

In venture capital, Vinod Khosla likes to go his own way, which is why he’s been so successful. He was the founding CEO of Sun Microsystems, and then moved to venture capital and became a star partner at Kleiner Perkins, where he backed Juniper Networks, Cerent (sold to Cisco for $7 billion) and NexGen (sold to AMD and formed the basis for its challenge to Intel). About five years ago, after becoming a billionaire, he left Kleiner and started Khosla Ventures to invest his own money. He was mostly drawn to clean tech at a time before it was popular, but still kept his hand in Web and other tech startups (Aliph|Jawbone, iSkoot, RingCentral, Tapulous, iLike, Slide, Xobni). Khosla Ventures already has more than 50 companies in its portfolio (see slides below).

Earlier this month, Khosla raised $1.1 billion for two new funds, taking money from outside investors for the first time. I spoke with Khosla on the phone about his new fund, his approach to investing, clean tech and more.  He compares Web startups to water startups, dismisses entrepreneurs who think about exits before building value, and contends that cleantech companies can command as high margins as hardware or software companies.  “It’s a business strategy decision,” he explains.”

In the interview, Khosla talks about his investments in Aliph, RingCentral, eASIC, iSkoot, and Xobni. In terms of what he’s looking for, he declares “we love material science.” And in his seed fund, in particular, he says, “We’re not looking for completeness in things. We’re not looking for business plans. We are not looking for meeting every fiduciary requirement of an investor. We are looking for great technical ideas and great technologists.”

The 25-minute interview and full transcript are below. I’ve bolded parts for emphasis.

//

Interview Transcript

Mr. SCHONFELD: Well thanks for taking the time to speak to me. You just recently raised a pretty large fund or actually a couple of funds, right, $1.1 billion for two new funds. And I believe this is the first time you really took outside money. Can you talk a little bit about that whole fund-raising process and why you decided to reach to outside investors?

Mr. KHOSLA: I think my general feeling is the scale of the opportunity we see is pretty large. You know, when I started doing things on my own, I was figuring – remember it was a very nascent market. And there was a lot that was unknown about the renewable marketplace in 2004, early 2003 when I was planning on it. The world does change for the better. Much larger opportunity set and it probably requires, you know – there’s more opportunity than I would have thought five years ago.

Mr. SCHONFELD: Right. Now, you have been really focusing on this area specifically for five years. While still, you’re still making an investment in more traditional web companies and the type of technology companies you’ve been investing in for years. But can you just tell me a little about the difference in the dynamics between the companies that are renewable energy companies versus the companies that our readers probably are more familiar with, web companies and hardware and even chip companies.

Mr. KHOSLA: Yeah, still…

Mr. SCHONFELD: There seems to be a disconnect, even in the Valley, between the cultures of these two types of tech companies.

Mr. KHOSLA: You know, I find that a pretty narrow view on behalf of people who sort of repeat that, I’ll call it a platitude for now. In the following sense, if you look at a venture firm like Kleiner Perkins and look at their portfolio, I would guess that 20 percent of the portfolio —and this is before renewables—ends up in things that are purely capital-intensive like biotech. 20 percent ends up in really capital-intensive stuff like biotech. 20 percent ends up in capital-light things like a Web start-up, let’s say, taking less than $30 million. So, 20 percent will take less than 30, 20 percent will take more than 300. And then the remaining 60 percent ends up in the middle taking, oh, you know, the bulk of the portfolio in venture takes between $30 million and $75 million or a hundred million. I think the profile in renewables will look exactly the same. And so, if you’re a broad-based venture firm and you do biotech and you do some of the capital-intensive projects, your renewable portfolio will not look that different.

Not everything in the world is building power plants or build biofuel facilities. There are plenty of things that are in the middle.

So if you’re doing LED lighting, it is just like a chip start-up. If you’re doing a new air-conditioner, it’s like a small equipment start-up, or telecom gear start-up. If you’re doing water, it’s like a Web start-up, at least the ones we’ve done.

Mr. SCHONFELD: How is a water startup like a Web company?

Mr. KHOSLA: Well, for 15, 20 million dollars, they’ll have products in the marketplace and be able to be cash flow positive. Less than $25 million, I would guess, because they’re making membranes. Then you make a membrane, they put it into existing systems. Now, they could have a capital-intensive model and build a desalination plant but they’re not going to. They’re going to build a membrane that goes into existing desalination plants. And so, it’s a very simple model and in all those – in almost all these cases that opportunity exists. Even in the extensive biofuels area, where you’d think it’d be very capital-intensive, you know, it’s easy to cut deals like LS9 announced one with Proctor & Gamble. That’s publicly announced. You can look that up, and make sure it is capital-light. There are companies that are pursuing licensing strategies that are also relatively capital-light.

MR. SCHONFELD: Already you have what, about 50 companies in your Khosla Ventures portfolio, somewhere around there? MR. KHOSLA: More than that. I don’t know the exact count but yes, more. Well above 50.

MR. SCHONFELD: So the new fund will be used for follow-on investments to the existing portfolio as well as new ventures or is it – or the existing portfolio is already taken care of with the capital allocated to the previous funds? MR. KHOSLA: Well, both of the funds will be new investments. But there are provisions for existing portfolio companies to get in, you know, we’re not going into the details but the bulk of the funds will be new investments.

MR. SCHONFELD: And do you see going forward the mix being pretty much the same? It seems like it’s two thirds clean tech and one third more traditional tech. MR. KHOSLA: Yeah. We do expect the mix in the future to look similar to the mix we’ve had in the past.

MR. SCHONFELD: Let’s take both of these techs one at a time. So, the Clean Tech companies are – are these located all over the place? Are these Silicon Valley companies and what’s your criteria for investing in these companies? I mean, at first glance a lot of these companies seem like material science companies or companies that other investors maybe wouldn’t even look at or would pass on because it’s not – it’s not a familiar model to them, right? So, you’ve invested in a lot of technology companies. Obviously, the problems they’re trying to address are large, but in terms of the actual business model and economic models of these companies, where’s the leverage?

MR. KHOSLA: Well, you know, first because it’s a diverse area and there’s no one business model. There will be a range of business models that will be used and will make sense and just like any other tech start-up, these companies are run by entrepreneurs who are pretty damned adaptive. You know, they’ll move pretty quick and adapt to whatever the environment says.

MR. KHOSLA: If the market changes, the money is available or the money is tight, they adapt to that. These things entrepreneurs do all the time. You saw that in the dot-com thing. There were people who could use a hundred million in the dot-com, and people who could adapt and go back to running on a million dollars a year. We saw that in dot-com companies and I think the same is going to be true in this space. And because the space is so large you’ll see a lot of diversity in the range of business models. I forgot the first part of your question.

MR. SCHONFELD: I can rephrase it. What are you looking for when you’re going to make investments in this area, what are the key…

Mr. KHOSLA: To your question, we love material science. We love serious technology innovations and there is a strong bias towards large technology innovations that are sort of disruptive to the current market. And that is very much a charter of what we are doing and we don’t mind larger technology risks especially in the smaller seed fund, which is really geared towards science experiments, which other people generally, as you say, won’t do.

The main fund will look like any venture fund and we’ll invest like any other. We’ll do seed, A and B and C investments. And there the risks probably will be a little less of the speculative stuff the seed fund might do. And I agree with you, there will be fewer people in the domain of the seed fund but the seed fund will do things that take a million dollars here, our $2 million there to roll out a really radical technology idea. And then it becomes a regular business plan.

In that stage, in the seed fund, we’re not looking for completeness in things. We’re not looking for business plans. We are not looking for meeting every fiduciary requirement of an investor. We are looking for great technical ideas and great technologists and yes, lots of PhDs in hard-core science disciplines.

Or just wild ideas that sort of have huge upside potential and sometimes may not need a radical technology breakthrough. So Xobni, which we did in e-mail , is an example of something that would be—in IT that fits into the seed fund because it’s a wild idea to do e-mail in this day and age. It has gotten great traction. So, that’s what we are looking for in the seed fund. In the main fund, we look for more complete management teams and more complete technology.

Mr. SCHONFELD: But for Xobni, that seems at first like the opposite of what you’d be looking for because a lot of people might think that e-mail is done although obviously, it has a lot of problems.

Mr. KHOSLA: Well, in fact I would say most people wouldn’t invest in e-mail because they think e-mail is done. In that case, it was an idea that we thought compelling and without going into the details, users have adopted it and used it enough to prove to us that it is compelling. And so all I’m saying is, we will do non-technology IT stuff in the seed area. We’ve just done another seed that I won’t mention but it’s not renewable but green, it’s just a great idea in a completely wild space that most VCs wouldn’t even think of touching. But it’s a regular technology start-up. And hey, great, so we are open minded on what we are looking for. On the green side, generally it should focus on the technology, technologist, a breakthrough innovation, not just a minor iteration.

Mr. SCHONFELD: Looking at your portfolio, overall which of the companies are the most mature? Have you had any, have there been any exits from the portfolios so far or -

Mr. KHOSLA: You know, we’ve had some – we’ve had a couple of sales and I don’t know which ones we’ve talked about publicly. They’ve been OK, good returns. So, you know, on average sort of a few times our money. Nothing I’d call a home run today but in terms of maturity, obviously, Aliph or Jawbone is a pretty exciting start-up for us. You know, a couple of, sort of nine digit revenues and cash flow positive and all the things you’d look for in a mature company. And you know, and so, eASIC is doing pretty well in semiconductors, we’re happy with that. Let’s see, iSkoot is doing really well in the mobile space. I’m trying to pick different areas.

You’ take something like RingCentral. It doesn’t need any more money or financing, it is relatively mature recurring revenue business – not really worried but you know, we could sell it tomorrow. We have not been in a rush to sell it. We don’t care about exits as much. We care about building fundamental value. So, in that sense we are a little bit different than other investors. Our focus is not on exit. In fact if you talk to any of my entrepreneurs, I’m generally saying don’t sell the company when other investors want to sell. I’d much rather focus on building long-term value in building companies rather than worrying about exists.

In fact, here is the thing, if a business plan talks about exits in the first two or three pages, I throw it out of the basket because I think, culturally it’s the wrong kind of entrepreneur for us. I literally if they talk, or mention exits in the first, say, in the executive summary or the first three pages of a business plan, it’s two strikes against them right there because I’m not interested in people where exit is top of mind. We care about building companies and building values. And that’s sort of the kind of culture we’re trying to do at Khosla Ventures.

Mr. SCHONFELD: Right, so, what advice would you have for entrepreneurs who you know are looking at different options? I mean, when is the right time to sell and when is the right time to keep going?

Mr. KHOSLA: You know, we could sell Aliph today. We could keep the cash flow positive company going. I’d rather take it towards an IPO. RingCentral is cash flow positive, going, you know, over a 100,000 small businesses as customers. We could sell it today but I still think, there’s time to generate value. It depends on what’s going on internally. If there’s good growth prospects and more value to be built then you go build that value instead of trying to get an exit. Wide Orbit is cash flow breakeven and sort of mature. You’d call it a mature company by venture standards, we’re not interested in, you know, getting out. Now having said that, if somebody comes with a great offer, we’ll always look at it. You know, we’re not opposed to exits. All I’m saying is it’s not the first thing we worry about. We worry about building value and building companies.

Mr. SCHONFELD: Right. And so what should entrepreneurs take from the fact that you were able to raise this $1.1 billion fund which I think is – it’s two funds but it was a sort of a single raise, right? Which I think is the biggest in several years. Is that just because you’re Vinod Khosla or do you see something – you see some -

Mr. KHOSLA: You know, I think the message is there are plenty of me-too two investors and there’s good investors around and money from – new money for that kind of thing is tight. But if you’re trying to do something different like we are, then investors, limited partners are willing to put up the money for it. I mean, and there’s definitely, we’re very active with new investors. We’re looking for ventures and our LPs just want us to take the risk for a file I just talked to you about. And there is appetite for risk.

Mr. SCHONFELD: Do you think that we’re going to be seeing more money flowing into venture capital? There’s been a big debate as whether there’s been a reset or not, you know, for investments going to venture capital and you know, just the whole financial crisis and how that impacted limited partners and how big institutions, you know, are rethinking their allocation to venture as an asset class. Is this an anomaly or -

Mr. KHOSLA: You know, my bet is big institutions will continue investing in venture capital but they’ll be more selective. But I don’t think, you know, frankly, we could have raised a lot more money if we wanted to if we had the people to put it to work. So I do think big institutional investors will continue to fund venture capital, but they will be much more selective and not every venture capital group will get follow-on funding. You know, it’s not too loose in my view and I think that’s going to change, and that’s a good thing.

Mr. SCHONFELD: And what’s your view of the IPO window? Will that ever really open up again or are there fundamental structural phenomena that is keeping it down not just the economy, but you know, everything from Sarbanes-Oxley to -

Mr. KHOSLA: I am pretty sure it will open up again. When is a little hard to predict and that’s why larger funds and deeper pockets are better for both venture funds and for entrepreneurs. I mean, today if I were an entrepreneur, I’d be very careful about only going with people with deep pockets. Because it matters. Now much more than it did before.

Mr. SCHONFELD: So if you’re giving advice to – if I’m an entrepreneur looking for different areas to go into and assuming that I can pull together a team with the required expertise, you know, what’s the counter-intuitive sort of space to go into right now? I would even say Cleantech, there’s a lot of startups out there . . . Mr. KHOSLA: You know, my advice to entrepreneurs is to go into the area of their expertise.

Mr. SCHONFELD: What’s the company that you would invest in in a second, but you haven’t really found it yet? What’s the problem that isn’t being solved by the companies that you’ve looked at that needs solving?

Mr. KHOSLA: Well, for example, storage for electricity is not a problem that has been solved. So, it is not a problem that has been solved.

Mr. SCHONFELD: For portable storage, for large…

Mr. KHOSLA: Well, both portable and stationary storage is not a problem that’s been solved. There’s lots of opportunities in bio materials so you know, in information technology there is, like low power is still a big deal. And so it’s hard to sort of single out areas and I see opportunities and interest, in business trends in almost every area.

Mr. SCHONFELD: Right. So what are your feelings about your first company, Sun Microsystems, being acquired? Mr. KHOSLA: You know, I don’t want to - I think it’s better Oracle acquired it and stayed in the Silicon Valley culture than, say, IBM acquiring it. But frankly, you know, that was a long time ago for me.

Mr. SCHONFELD: Where do these new cleantech companies fall? Are they closer to – do they look more like an industrial company when they mature or do they look closer to, you know, a hardware company or do any of these have software-type margins and how is that possible?

Mr. KHOSLA: Yes, it’s possible. You know, in each case, it’s a business strategy decision. I generally disagree with most of the very high margin opportunities. Why? Because it’s a business strategy tradeoff: the lower the margin you take, the faster you grow.

Yes, a Juniper can do 65% margin, but I tried really hard to convince them to go with 50 percent. Actually, it just increases market penetration faster. And so what are you trying to achieve?

And there are times where . . . take somebody like Infinera. I haven’t been on the board for a couple of years so my data is old. But we had a tradeoff between getting 10% margin on the chassis and 80% margin on the cards, or getting 30, 40, 50 percent margin on the total thing. And one was immediate revenue and margin, and the other was locking in lots of chassis with customers at low margin and then they kept buying line cards from you for ten years. It’s a business strategy question and it worked very well for Infinera. So I think this is a red herring.

Every one of our companies has the opportunity to go after niche markets or a large market. And the larger the market, the more aggressive you have to be.

Mr. SCHONFELD: OK, great.

Mr. KHOSLA: OK.

Mr. SCHONFELD: Thank you for taking the time. I appreciate you taking time on your schedule to talk to us.

Mr. KHOSLA: Great. Thanks a lot.

Xobni Plus has a heavy emphasis on improving search, which is one of the key components the service has always been based around. Users will now be able to craft more advanced search queries, using either a GUI-based ‘query builder’ or Xobni’s own markup language, which lets you manually specify attributes like “attachment=yes” or “from=Jason” (Gmail offers similar search features, and they are very handy once you’ve gotten a hang of them). Other improvements include Xobni’s autosuggest feature, which can use linked Facebook and LinkedIn accounts to pair Email address with full names, as well as the ability to search within your Xobni ‘feeds’ in the sidebar.

Xobni may be calling this a ‘Plus’ version, but pretty much anyone who uses the service with any frequency is probably going to want to upgrade (I’d be surprised if the company puts much effort into adding new features to the free version after this). Xobni is expecting fairly broad uptake by its users, so it’s pricing the upgrade at a modest one-time fee of $29.95. However, the company also has more task-specific “Pro” features in the works that will likely appeal to different segments of their userbase, and it sounds like these will be more expensive (a mobile-only premium product is also in the works, with plans to release it later this summer).

It’s been just one month since email startup Xobni got an investment from the Blackberry Partners Fund, which brought its total B round up to $10 million, and already it has a working prototype for an upcoming Blackberry app. Xobni executives were showing off the app at a Mobile Meetup in San Francisco last night, and the screenshot above found its way into my inbox (which is “xobni” spelled backwards, you know).

The app was working, and could be released sometime this summer, according to my source. The photo above shows the app on a Blackberry Bold, and appears to be showing off its contact search functionality. You type in a few letters, and it returns the contact information for every match in your inbox (even people who you haven’t necessarily added to your address book yet). I wonder what else it can do.

Xobni, which is a plug-in for Outlook that incorporates data from various social networks, currently does not have a mobile client. But the company has hired a small team of engineers to work on mobile apps, with Blackberry being the first device to get one.

Not only is there the connection with the Blackberry Partners Fund, but I’ve been told in the past that there is about 50 percent overlap between Xobni users and Blackberry owners. (There must be an Outlook-Blackberry mental axis out there). So it makes sense to go after the Blackberry first. But the startup cannot afford to ignore the iPhone. Can it?

With the news that Facebook is going to begin allowing developers to incorporate full streams into their applications, developers are scrambling to get their apps up to speed. This morning we got our first look at the upcoming new version of Seesmic Desktop, and now we’ve learned that Xobni, the popular Outlook plugin that helps make Email easier to manage, will be going live with a new upgrade beginning at 6 PM tonight. Because of the way Xobni is built users won’t have to download an upgrade either – all changes will be server side.

Up until now Xobni has included some basic Facebook contact information, including profile photos and status updates, but it wasn’t as comprehensive as your full Facebook news feed (you couldn’t see how your contacts were interacting with each other, for example). Now you’ll be able to see this information at a glance directly from your Outlook mail client, which is obviously far more efficient than having to manually check your Facebook page.

Unfortunately, Xobni is still available only on Windows machines, so Mac users are left in the dust.