The company and idea were created by David Friedberg — also the founder and CEO of The Climate Corporation — and Steve Pretre, who will lead the startup as its CEO. Friedberg brought in Climate Corp’s investors (as well as Climate Corp itself) to back MetroMile, and the company has already raised $4 million from NEA, Index Ventures, First Round Capital, and SV Angel, in addition to Climate Corp.

Customers using MetroMile’s new service — which is only available in Oregon because it needs state approval — place a device called the Metronome into their car’s onboard diagnostic car port, called the OBD-II. You might have never noticed it, but the OBD-II is standard port on all cars built after 1996, and has to be accessible in the front dashboard within three feet of the driver. The port is one of the ways that car data is being unlocked for third party developers (see my GigaOM Pro report, subscription required).

After the Metronome is plugged in, it accesses all the car computer’s data, and specifically collects (for this initial product) information about how much the customer is driving. The cellular connection in the Metronome enables MetroMile to process the data in the cloud, and the Metronome also has GPS to track distance. I was wondering if a cell phone app would have the brains to do this just as easily (and clearly more cheaply), and Friedberg told me in an interview that they need the data to be collected by a device to avoid fraud and ensure accountability.

Once MetroMile has the driving data, it can charge its customer only for how much — or how little — they’ve driven per month. Drivers who only occasionally use their car — say for weekend trips — would pay much lower rates than a person who commutes in their car an hour every day, each way.

While the idea sounds boringly simple, it’s meant to target a specific set of drivers that doesn’t drive all that much and who for years have been subsidizing those drivers that do drive a lot through traditional car insurance programs. Most of the accidents are done by drivers that drive a lot, says Friedberg. This new type of low mileage demographic tends to be young, urban, environmentally conscious, and maybe even a member of car sharing groups like Zipcar.

That target demographic is alive and well in MetroMile’s initial city, Portland, where the dream of the 90′s are also alive, and everything has a bird on it. MetroMile said it can offer this type of driver insurance for 20 to 50 percent less cost than traditional insurance, with equal or even superior coverage. Friedberg told me that MetroMile has discussed its insurance products with car sharing companies, but that the company is really targeting car owners, as car sharing drivers are still a small slice of the population.

MetroMile also shows the customer their driving data through an online dashboard. Down the road, MetroMile could offer other types of services using car data. I could envision a service that gives recommendations for how to cut down on driving (to save fuel costs), in the same way that Opower provides recommendations for lowering energy consumption.

In that way, MetroMile, like the Climate Corporation, could have a planet-friendly slant. Once car drivers know more data about their own driving habits, their likely inclined to drive their car more efficiently.

The traditional insurance companies are also looking at using devices and data to create new products, and the New York Times had an interesting article on this trend this weekend. Friedberg says that standard insurance companies won’t readily accept pay-per-mile insurance rates because then they would be forced to raise rates on the drivers that drive a lot more, to cover the lower mileage drivers; drivers that face higher rates then would just defect to competitors, said Friedberg. Car drivers are also wary of what types of data the car insurance companies are collecting with these new devices, and also how the insurance companies would use such data.

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Fresh on the heels of its big $55 million round of fundraising, Calxeda has announced that it’s 64-bit chip will be in the market by 2014. It’s current chip is called EnergyCore is only 32-bit. — GigaOM Pro blog.

Amazon’s data center efficiency VP James Hamilton gave a talk recently at the First Round Capital CTO Summit in which he explained to budding entrepreneurs how he would approach providing value to the modern data center. — GigaOM Pro blog.

The third quarter in cleantech brought into focus the successes and challenges of more-mature companies like Tesla, Airbnb, and Zipcar. It also highlighted energy challenges in India and China. — GigaOM Pro report (subscription required).

Owning physical items — cars, apartments, office space — has both lost some of its luster and will be increasingly inefficient for a global market. It is shifts like these, combined with catalysts like mobile technology, that are driving a greater interest in the share economy, which can broadly be defined as a marketplace where business models are built around consumers choosing access rather than ownership. — Opportunities and Risks in the Share Economy: GigaOM Pro Report (subscription required).

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That’s why it’s fun to come across a startup like Firefly, the creation of four University of Pennsylvania undergraduates who want to make it drop-dead easy for companies to guide customers through their websites by co-browsing or sharing screens without plugins or downloads.

So if you’re perusing your a healthcare provider’s web site and get stuck on a form, the customer service agent can with a button click,  get in and share that screen — without seeing any of the user’s other tabs or screens — to walk the user through the process. To facilitate this, the company just adds a few lines of JavaScript code to the URL header.

The product has gotten some ink  and it is cool. But what impressed me was the co-founders. I met two of the three – Wharton undergrads Patrick Leahy and Justin Meltzer  – at Boston AngelHack last spring, when Leahy was in in the midst of a hackathon road trip.

Just coming off the 48-hour Penn Apps hackathon, Leahy Bolt-bused up to Cambridge for the 30-hour Boston AngelHack, before jumping aboard StartupBus, a 70-hour hackathon-on-wheels to South By Southwest, where he was going to participate in — wait for it — another hackathon. Code means a lot to this guy…

Firefly co-founder Patrick Leahy

Foresaking Wall Street for code

So much, in fact, that Leahy turned down an investment banking internship with a New York financial services giant to focus on programming. “I did one internship on derivatives trading last year and liked it and was going to go back for investment banking, but I want to build the company,” Leahy told me by phone last week.

Leahy and another Firefly co-founder Dan Shipper are startup veterans, having already launched Airtime for Email, which gives companies a way to brand their marketing messages in email and track how those emails are treated. Were they read? Nuked? Forwarded? Never opened?

Leahy speaks about code as someone who is knowledgeable but still eager to learn. “We wrote the first version of Firefly at Penn Apps using Ruby on Rails but we couldn’t get to the level of complexity we needed so we rewrote it at AngelHack in Node.js. We learned that language at AngelHack and it’s perfect for what we needed,” Leahy said.

Picking the right tools

“Programming languages are like different sized kitchen knives — they suit different jobs,” he said. Ruby on Rails is a great framework for building “CRUD”  or Create, Read, Update, Delete — applications, he said. ”If you have a big table you want to edit — a customer information page, your sales rep page, Ruby on Rails if fine,” he said.

But for Firefly, which needs to handle fast browser-to-browser communication, Node.js was better. “We have to pass messages back and forth so our server sits in the middle and we wrote code to connect all those browsers. This is an evented pattern where you’re having a conversation, listening for things to be said and holding till you hear them. Ruby on Rails is not good for that but a functional programming language like JavaScript makes it easy to call a function to handle an event,” he added.

The Firefly foursome used to work out of dorms and apartments but is moving into the offices of First Round Capital, although there are no plans to take venture funding yet.

To be sure, Firefly isn’t entering an empty stage. LogMeIn offers a popular screen charing application and Salesforce.com bought GoInstant a screen-sharing company in July for $70 million. But Salesforce is attacking big companies with a full array of analytics and other perks while Firefly focuses on customer service and might be more attractive to smaller companies. Whatever the competitive landscape,  I wouldn’t sell this team short. They show a remarkable maturity that complements their youthful exuberance. Asked if Firefly was seeking venture capital, Leahy was cautious.

“We want to get to free cash flow and get stable before thinking about raising money from outside. We want to make sure we can manage our own money first,” Leahy said.

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The new fund, appropriately called Brooklyn Bridge Ventures, will look to provide early- and seed-stage funding to start-ups in the “great Brooklyn area,” which may still include startups from Manhattan and other boroughs. But the priority will be to invest in the Brooklyn scene, which is home to many emerging companies and is where a lot of  startup workers call home, said O’Donnell, who’s leaving his position at First Round.

“I’m a Brooklyn native and resident and I thought it would be cool to put a fund there. Brooklyn is a freight train of startup development. I would guess 60 percent of people at venture-backed startups live in Brooklyn, particularly in the technical and design community. A number of startups have turned up there, and it’s a more economical place.”

O’Donnell told me the fund will be about $7 million to $10 million and is being funded by unnamed investors, who first approached him about his own fund. He said even with the rise of seed-stage and angel investors, there’s room for an investor who can build deep relationships with startups and provide critical help along the way, including addressing the ever-present need for procuring good talent. O’Donnell is known for hustling and working closely with entrepreneurs and should be a major catalyst for the Brooklyn tech scene, said Fred Wilson of Union Square Ventures, in a statement.

O’Donnell said he’s not interested in hardware-intensive or pure content startups but otherwise, he’s open to all ideas. At First Round, where he helped the firm get settled in New York, he invested in GroupMe, Backupify and Single Platform. He previously helped source deals at Union Square Ventures including Etsy, del.icio.us, Bug Labs and Oddcast. O’Donnell has been a big force in the New York tech scene, founding nextNY, an organization that connects people in the local tech scene and writing a must-read email newsletter, highlighting local events. He also founded Path 101, a career guidance start-up.

O’Donnell plans on staying close to First Round Capital and sees opportunities to collaborate on deals. And he has the blessing of Josh Kopelman of First Round Capital, who wished him luck. After all the hard work in helping build the New York tech landscape, O’Donnell said there’s still a lot of work to be done to keep the momentum going.

“This is the second inning of New York. The fact that companies like Facebook and eBay and hopefully Twitter and Amazon are coming to New York means we’ll see more companies build engineering groups here. Google has been a big boon for the engineering culture here, and it’ll only continue,” O’Donnell said.

Image courtesy of Flickr user Garbowski

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Along with the climate focus, Friedberg says the company, which uses big data tools to offer analytics and reports to customers, could eventually launch analytics for other verticals beyond the agriculture industry. Right now, five-year-old The Climate Corporation sells its “Total Weather Insurance” product, which gives farmers info about weather and helps them buy insurance to protect them from losses from extreme weather events.

In addition to the branding refresh, The Climate Corporation is bringing former Senator Byron Dorgan onto its Board of Directors. Friedberg says Dorgan has been “a big proponent of the American farmer,” and can aid The Climate Corporation in working with farm-related policy, like the $12 billion per year that goes into federal crop insurance.

The Climate Corporation has other important connections and deep pockets, too. It has been backed by over $50 million from investors including Google Ventures, Khosla Ventures, NEA, Index Ventures, Allen & Company, Atomico, First Round Capital and Code Advisors. When the company raised $42 million of those funds earlier this year, Khosla Ventures partner Vinod Khosla said “Now WeatherBill can help farmers globally deal with the increasingly extreme weather brought on by climate change.”

The traditional insurance industry is still figuring out how to address this world of increasingly unpredictable weather, and The Climate Corporation’s technology is bringing that to smaller businesses and also via the web. The Climate Corporation is essentially giving businesses tools to adapt to climate change. While climate change adaptation has kind of been a dirty word, because it was positioned in contrast to preventing climate change, it has become increasingly clear that climate change is coming, and more and more investors will likely look to back adaptation technologies (see adaptation is the hot new sector in greentech.)

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Sincerely’s business is simple but ambitious: make it easy for users to make physical copies of photos taken on their mobile phones.

Postagram, Sincerely’s first product, enables users to send postcards made from the photos they’ve taken with Instagram, the popular photo-sharing app for the iPhone. Postagram, which can be downloaded on the iPhone or on the web, integrates with the Instagram API and allows users to turn their Instagram photos into pop-out postcards with short, 140-character messages. For 99 cents including postage, Postagram will print and mail the postcards anywhere in the world.

As clever as Postagram is (and I think it’s really clever), basing one’s business on a third-party’s software API is never a smart bet for the long term. Twitter developers have learned that the hard way. Brezina is quick to emphasize that Postagram is just the first of many photo printing products Sincerely has in the works for various photo-sharing programs and mobile platforms.

What I love about Postagram is that it makes it so easy to bring your photos back into the physical realm. Since I started using a digital camera in 2005, I can count on one hand the number of times I’ve actually had any photos printed out. Sincerely aims to bring back tactile photo sharing, the kind we used to have with picture frames and scrapbooks. For all the perks of digital photography, there’s still something special about having hard copies of certain pictures.

Brezina, who left day-to-day operations at Xobni in 2010, co-founded Sincerely with Bryan Kennedy, another Y-Combinator alum. The company isn’t saying who their investors are or how much money they’ve raised, but Sincerely’s five-person team is working out of the San Francisco office of First Round Capital.

In this short video clip, Brezina gives us his Sincerely elevator pitch and explains why he cut his post-Xobni travels short to come back to the startup “gold rush.”

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The San Francisco-based company raised $800,000 in June in a (previously reported) round led by First Round Capital and Google Ventures and including Reid Hoffman, Deep Nishar, Niel Robertson, Hadi Partovi, Ali Partovi, Carlos Cashman and Micah Adler.

The thought behind VigLink is that in the course of regular writing, web publishers link to sites that they don’t know have affiliate programs. Rather than requiring bloggers to sign up for each program individually, VigLink serves as the middleman. The content creators receive payments after they reach a $25 minimum for all the affiliate programs combined (a much lower barrier to entry than if they had joined all of them individually). VigLink also maintains publishers’ links to make sure they hook up to current offerings.

Meanwhile, merchants are given the ability to track participating publishers and reject those whose content or audience they don’t feel is appropriate. Visitors probably won’t notice anything out of the ordinary as they read and click on links, unless they look very closely at the URL, said Viglink CEO Oliver Roup. His company, of course, takes a cut of any CPA revenue (and later may expand to CPC).

VigLink (which has a UK equivalent startup, Skimlinks) sent me a sample report showing that Gizmodo leaves approximately $4,400 per month on the table in unrealized income. That’s not based on a relationship with the site, but an estimate from crawling its outbound links, using public traffic estimates and applying a model of how many click-throughs the site is likely to get (see screenshot). VigLink says it already has relationships with sites that have a combined 100 million page views per month, but it’s not specifying which ones. It does not require a minimum amount of traffic to join the program.

My concern with VigLink would be that a taste of the revenue from linking to The Gap, for instance, might lead a normally interesting blogger to write about nothing but sweaters and khakis. We don’t really need any more link farms in the world. Roup said that VigLink will encourage participants to follow the FTC guidelines about paid blogging. He also noted that as compared to something like the double-underlined links from Kontera (which I personally find way too obtrusive), VigLink’s monetized links blend in with the rest of the text and the normal course of reading.

The next step for VigLink is to expand beyond people who publish their own sites and blogs to places like Twitter and Facebook where bevies of users trade links. Roup hinted that this was in the plans, and said that it’s actually already possible for sites like those to integrate with VigLink’s open API.

As a side note, I followed up with Rich Miner at Google Ventures because I was interested in the nature of the VigLink funding given the startup’s product is somewhat close to Google’s AdSense and it was one of Google Ventures’ first investments.

While both Miner and Roup said the overlap had been positive so far, Miner meanwhile relayed a cute story about how he met Roup — while judging a business plan competition at Harvard last year. “Something about him struck me,” Miner said, noting Roup majored in computer science at MIT and “perhaps looked a little scruffy compared to the other polished MBAs.” Roup didn’t win the competition but he did get the mentorship and eventually, funding.

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In a series of charts, Mark Heesen, president of the NVCA, showed how now is a terrible time for early-stage companies looking for venture capital. The presentation also made me wonder if greed and complacency have broken the industry by allowing too much capital to flow into it. Generally, the larger and more established the firm, the less interest it had in early stage investing, partially because larger firms have a large portfolio of existing companies to deal with, but also because it’s easier in tough times to make safer investments in more established companies. However, early stage investments are where the big returns are, so it’s hard to believe that firms that abandon that for any length of time will be able to weather the bigger changes buffeting the industry.

Plus, since it’s the larger firms that are proving to be less agile, it seems obvious that venture investing doesn’t scale well (a point made by Heesen in the call). So why did some VCs turn into such lumbering giants ill-suited to adapting to risk and economic change? Greed played a role as new money poured into funds run by these firms during, and even after, the dot-com boom. The more money under management, the more a venture capital firm earns in fees. The world of startup investing has also changed in the last few years, and several firms either missed it or just decided not to adapt to it.

Companies could be started for less and sold more quickly — but also for less money. As it became tougher to take companies public and deliver outsized returns, some VCs started thinking about how to deliver decent returns even if the IPO market never returned to previous highs. Some, such as First Round Capital and Union Square Ventures, raised smaller funds. Others couldn’t figure it out. When I talked to partners at Sevin Rosen back in 2006 about its future, they couldn’t see where to put large amounts of money and make great returns. So they decided to quit raising another fund — effectively shutting down a venerable player in the industry.

But many in the industry kept going along with huge funds and expectations that the venture investing would return to a level of normal that preceded the bubble. And they’re willing to ask the government to help make it happen. They latched onto clean technology as an industry that would require access to their large capital base and would deliver huge returns. It might, but the fact that 63 percent of VCs are planning to increase their investment in cleantech, while substantially decreasing investments in other sectors, makes me think of several thousand people on a sinking ship rushing to grab a place on 10 lifeboats. That kind of group-think isn’t going to get LPs excited about investing, and it certainly isn’t going to boost returns.

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