Founded in 2009, RelayRides began offering what founder and CEO Shelby Clark calls “neighbor to neighbor” car sharing in the Boston area in September. The concept is like “cloud computing for cars,” as Sunil Paul, CEO of competitor Spride Share, has put it to us. With cloud computing, users can share computing infrastructure over the Internet, accessing software, data and other resources on demand. With transportation and car sharing, the idea is to provide mobility as a service. At a basic level, rather than buying a car, you could buy access to a car whenever you need it.

Piggybacking on the idea of popular car sharing services like Zipcar, RelayRides “makes it easier to live without a car,” said Clark, and can lead to “stronger communities.” Collecting feedback from users in Boston, RelayRides has learned that people on both sides of the car share equation — vehicle lenders and borrowers — “feel like they’re helping each other,” either by providing some extra income through the rental fee or by providing wheels when they’re needed. Car owners set their own hourly rate and get 65 percent of the fee, while RelayRides takes a 15 percent cut. The remaining 20 percent goes toward insurance.

RelayRides is still solidifying its deal with Google Ventures and August Capital, and the startup tells us that the amount of investment should be disclosed in the next few days. RelayRides has previously raised $500,000 in angel investment, and Clark said it has already received some funds from Google Ventures. He declined to comment on questions about profitability.

Starting on Tuesday, “a handful of vehicles” will be available in the San Francisco fleet. Car owners in San Francisco can enroll on the company’s website, prompting a call from RelayRides to answer any questions. From there, the car owner can schedule installation of some hardware, which enables communication with RelayRides’ servers and controls access, so only a user with a current reservation can unlock and start the vehicle.

Vehicles enrolled in the Boston RelayRides fleet have a keypad interface that lets drivers extend a reservation, but Clark said the San Francisco fleet will feature an upgraded, more streamlined system without the in-vehicle interface.

Cutting the installation time to 1 hour, from 3-4 hours with the older system, the hardware changes could be a smart cost-cutting move for the company if it’s looking to expand to more markets. According to Clark, the company aims to serve not only cities but also areas with lower population densities — the suburbs and “urban fringe” — where traditional car sharing providers can’t profitably operate. Without the cost of owning and managing its own vehicle fleet, said Clark, RelayRides can afford to have more down time, or lower utilization rates for each vehicle.

For security, a RelayRides vehicle’s ignition will be immobilized except for access by the car owner or an authorized borrower. General vehicle locations can be viewed without a reservation, but users only find out the exact address via text message once the rental is finalized. RelayRides also emails the user a map at that point marking the vehicle location (each enrolled vehicle is outfitted with a GPS system for finding the vehicle and tracking mileage ). As Clark put it, since the keys are kept in the car and its location is being advertised, it would be “asking to be stolen” without these precautions.

Also on Tuesday, RelayRides will begin screening drivers who sign up on the company’s website (the company checks for a history of violations or tickets). Once approved for membership, drivers can reserve vehicles through RelayRides’ website and unlock a car during their time slot with a smart card. Next month, users will also be able to register San Francisco’s Clipper transit pass for this purpose, with RelayRides reading a digital signature on the card and assigning it to a particular user, said Clark.

For companies like RelayRides and Spride Share, insurance is one of the biggest bugaboos. Until recently, insurance regulations in California and other states allowed insurance companies to void a vehicle owner’s insurance policy if the car was rented out to others.

In September, however, legislation called AB 1871 passed in California that establishes rules for when a vehicle owner’s insurance policy stops applying, and when a commercial policy held by a service provider like RelayRides would kick in. RelayRides holds a $1 million supplemental insurance policy that goes into effect during each reservation period.

Clark believes the legislation “forced a lot of people to take a position on personal car sharing.” By clearing up a “gray area” for this type of business model, he said, the legislation has helped ease RelayRides entry into California. (San Francisco also garnered the most votes in a poll on RelayRides’ website asking where the company should expand next.)

Spride Share waited for AB 1871 to go on the books before launching its pilot program with local car sharing provider City CarShare. Asked whether RelayRides considered pursuing a similar partnership for its West Coast launch, Clark commented that Spride “cemented a relationship with City Car Share early on.” That left only Zipcar as a potential partner, he said, and RelayRides did not consider linking up with the car sharing heavyweight.

For more research on the intersection of green and IT check out GigaOM Pro (subscription required):

Car Data As the Next Platform for Innovation

Mobility on Demand Takes Aim at Transit Networks’ “Last Mile”

Location-Based Services: From Mobile to Mobility

20 Reasons Why Not To Do an Email Startuphttp://static.slidesharecdn.com/swf/ssplayer2.swf?doc=inboxlovebijannov2010b-101119123924-phpapp02&stripped_title=20-reasons-why-not-to-do-an-email-startup&userName=ommalik

In an email to me, Marashi wrote:

The creativity and courage needed to be a successful entrepreneur is special, but also fragile. Of all the creative venture adventures to dive into, challenging the consumer email market straight on (not communications) may be mission impossible.

This coming from a guy who raised $6.5 million in funding and sold his company to Yahoo for $20 million in 2009. Yahoo bought his company because they had pivoted into hosted search service for developers.

Last night, he spoke at the 500 Startups Inbox Love gathering in Mountain View, Calif. and shared some great insights and many reasons entrepreneurs shouldn’t start an email-focused start-up:

Despite our successful exit, we learned a brutally sober lesson — trying to fix consumer email platforms is like trying to fix the phone system — a startup simply can’t afford to do it. This lesson became even more clear to us as I spent the last year on Yahoo’s exec Product Strategy and M&A teams where I saw how the operators work and looked at many of the startup deals amongst the current class of entrepreneurs.

Formspring CEO Ade Olonoh

Earlier this year, Formspring, a San Francisco-based social Q&A startup, got tongues wagging when it raised $2.5 million in its Series A funding mostly from top angel investors. The round, led by Freestyle Capital, turned out to be a coming-out party for angel investors who have become a big factor in Silicon Valley’s ecosystem.

Seven months later, Formspring is making news again. We’ve learned the company has raised $10 million in fresh funding in a round led by Redpoint Ventures. Geoff Yang, a well-known digital media investor, is leading the investment on behalf of Redpoint. The new round values Formspring somewhere around $45 million. The company declined to comment on the funding.

Formspring’s is relatively simple offering; you sign-up and create a page and then anyone can ask you anything, even anonymously. In many ways, it’s like blog comments, minus the blog post. Apparently, this is something folks like to do; the company says it has about 40 million unique visitors who show up every month. That growth is costing the company a pretty penny and has been a focus of its recent hirings.

The new investment is part of a growing trend. Fast-growing startups with momentum are able to raise big rounds of money, as Sand Hill Road investors try to cherry pick from a vast number of consumer web and mobile companies.  Formspring fits the bill; the company claims more than a billion questions have been answered on its platform.

Formspring.me is also part of a group of startups (and large companies) trying to capture a piece of what is a massive and ever-evolving web trend: personal expression. It started with blogs; it spread with micro blogging (Twitter and Facebook) and, more recently, self-expression through remixing (Tumblr.) Answering questions as an expert is only an extension of that trend, which is why you’re seeing services like Formspring get momentum, and hence the money.

From the Video Archives Chat with Formspring.me CEO Ade Olonoh:

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Earlier this week, Gravity, a Los Angeles-based startup, launched a new service called Twinterest and outlined its intent to help personalize the web through what it calls an “interest graph.” This isn’t the first time the start-up — which has garnered $10 million in funding from the likes of Redpoint Capital and August Capital — has sought the limelight by making bold (and woolly) claims.

The company, which was started by Amit Kapur, Steve Pearman and Jim Benedetto — all former Myspace executives — came out of stealth in December 2009. Gravity initially wanted to reinvent the concept of conversations then data-mine these conversations to build interest analytics, and eventually build a business against these analytics. Suffice to say, I wasn’t a fan of the service, and took a dim view of its prospects. When it launched earlier this year in beta, the service was indeed a letdown.

Since then, the company has come up with a new strategy, and is now using Twitter feeds to build the Interest Graph, which it says it will then use to help personalize the web. Sometime in the future, Gravity CEO and co-founder Amit Kapur says, he wants to give publishers the ability to personalize content for each one of their readers.

One of the key building blocks for this “interest graph” is a new offering from Gravity called Twinterest. It’s a service that taps into the Twitter fire hose and hopes to map my interests and essentially connect them to some of the folks I might know. I tried it out and got some surprising results. For instance, the service says I have 476 interests including Country Music, Bernie Madoff, Appalachian State University, Debarge, Soviet Union and Anakin Skywalker.

Those “interests” are just straight up wrong. The rest of my “interests” remind me of a phrase we used to use often when growing up: Looking London, Going Tokyo.  What’s even funnier is that the service suggests that I should friend Rapleaf on Twitter (ironic, considering some of my writings about that San Francisco-based company). Gravity wants us to help fine-tune this “interest” data, so it can personalize the web in the future, but the Twinterest results so far make quite an un-interesting graph.

The inaccuracies in the interests displayed by Twinterest are symptomatic of some of the problems associated with natural-language processing services, which try to extrapolate my interest level in topics from proper nouns mentioned in tweets. I remember tweeting that I was listening to Debarge on the radio and feeling nostalgic. That doesn’t mean I’m interested in them.

Many services that propose to make sense of the Twitter feed and draw inferences have to deal with a whole can of worms. For starters, any service that proposes to build an interest graph or some sort of ranking, needs to do the following:

• Analyze the content shared by a user.
• Analyze the content of a user’s tweets.
• Analyze what others a user follows as a potential signal of interest.
• Analyze who follows a user to get a sense of authority of the user on that interest.

Gravity (and other services similar to them) have to figure our ways to do the aforementioned four things at scale, then build a taste graph for every single Twitter user. That’s not easy, nor cheap. One assumes Gravity has been able to do that — and have put some of their venture dollars to good use. But then as more data points are added to the mix, say Facebook, the complexity (and costs) of Gravity’s Interest Graph is only going to go up.

I think the challenge with services that use Twitter to draw inferences about me is that they only have an incomplete picture of me. My Twitter identity is very tech-centric. It ignores some of my real-world interests, and frankly, I don’t care to share a few things with the rest of the planet. In other words, Twitter can’t really help mirror the real me.

That said, it’s simple enough to build a content-discovery system based on the interest graph, and predictably, that’s why the company is building a news discovery service, The Orbit. I don’t think it’s really a very valuable service – i.e., it’s a terrible business idea. The idea of an interest graph is something that was initially championed by Hunch, which instead of doing natural-language processing, decided to start with a combination of machine learning and statistical learning.

Eventually someone will figure out a way to mine the web and build a personalized web experience. Gravity seems pretty far from it. This is something the guys who own the data – Facebook, Twitter, Google – will likely do.

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Post and thumbnail images courtesy of Flickr user Luis Markovic

Path is the personal network.  The personal network doesn’t replace your existing social networks – it augments them. Capturing a moment on Path is simple and contextual. Simply take a photo with your camera on iPhone and add context around that moment in the form of tags for people, places and thing.  These tags provide 3 types of context which we think help capture a moment. Think of it as a place for the memories along your path through life. (Path Blog)

The problem this app is trying to solve: we have too many friends (on Facebook) and as a result we miss key moments we should share with some of the people who are closest to us. We miss their photos and their status updates, on Facebook or Twitter. It is supposed to be private and keeps those beautiful drunken moments of personal shame, well personal. Ironically, for first few minutes of its life, the company was exposing all these private pictures on S3.

Path, in theory, seems to be a great idea. In reality, when you step back and think about it, the idea of a restricted, personal network has the utility of a toy poodle. The problem of too many friends is one that afflicts those who are hyper-connected and who often confuse their Rolodex for friends. Most people can do many of these things with Facebook, and more.

I downloaded the iPhone app, tried it for about half an hour and found invitations from some of the same people who are in my other social networks and well they aren’t quite 50-of-my-closest friends. Nevertheless, I did accept their invitations, just so I can try out the Path.

The Path app, for what it is worth is cleanly designed, and is fairly easy to use and is intuitive. It makes it relatively easy to sign-up for the service and even taking and sharing pictures is relatively easy.

So far I have about 25 people who are sharing their Path’s with me. By tomorrow morning I will have another 50 and then I will have to make a judgment call about whose lives are interesting and with whom I want to share my personal joys and achievements.

Of course, the real story is that half-of-the-50-who-matter-to-me don’t have iPhones or even own smartphones. Yes… there are people like that, and some of them actually live in United States. (For them, Path suggests, using the website.)

Path is part of a growing number of applications that want us to use our smartphones and share photos and life moments. On the web, DailyBooth is a stupendous hit. And there is Instagr.am, which is gaining popularity with hipsters. There is Picplz, which recently raised gobs of money, and there are many waiting in the wings.

If history has taught anything, photo services are great ideas but terrible businesses. Many become popular, but in the end struggle to find a business model. Such fate awaits many of these companies, including Path, which is also bearing the additional weight of history. Back in 2004, Josh Felser started a private media-sharing network, Grouper. He had to pivot from the original before selling the company to Sony.

Nevertheless, I am amazed by the frenzy of press around this application. It is perhaps because the company has been co-founded by three well-known Silicon Valley insiders – Dave Morin (who headed up early Facebook Platform efforts), Shawn Fanning and Dustin Mierau. Fanning, in the past was associated with Napster, Snocap and Rupture. Along with these three celebrity founders, the company has a laundry list of well-known investors — so many that it is hard to list them.

The personalities, of course are meant to paper over the intellectual marginality. It takes a lot more than just a collection of investors for a web app to become a social platform with large audience with high engagement, and then for that social network to become an actual business.

Yup, it is a Path to nowhere!

All it took was Google to supposedly offer $3.5 million to an engineer to not go to Facebook. Now, that is what rational people would call cutting off the nose to spite the face. But these are not rational times. I have been writing about the escalating irrationality in Silicon Valley, which for some odd reason exists detached from the global economic reality.

In past few months, I wrote about three major and potentially troubling signs.

• Silicon Valley & the Scent of Money talked about the increased number of startups getting funded and the amount of money being pumped into the startups going up, thanks to hyperactive, always tweeting, angel investors.
• Silicon Valley’s Talent Crunch talked about how there was a decline in certain kind of engineering talent and other professionals in the valley, thanks to the breathless hiring from giants like Zynga, Google, Apple, Facebook and Twitter.
• The media’s focus on investors and not the founders.

There are some excerpts from Fred Wilson’s post I think are worth highlighting.

I think the competition for “hot” deals is making people crazy and I am seeing many more unnatural acts from investors happening. If it were just valuations rising quickly, I’d be a bit less concerned. But 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.

Irrationality often doesn’t seem irrational because it is often labeled as conventional or fashionable thinking. Let’s step back for a minute: if you take what Michael Arrington wrote or what Fred Wilson has to say or my own reporting, we are beginning to see signs of hyper-inflation in the web and startup landscape.

Fred doesn’t want to call it a bubble and he is right, mostly because it is not a classic case of mass hysteria, and instead it is a madness that impacts only a certain genus, the professional investor. The implications of this early stage investment hysteria are going to be felt across the ecosystem.

Let me explain.

Google, worried and perhaps tired of losing its great engineers and talented people to other companies including Facebook, decided to fight back with a weapon it knows can be effective in the short term: money. A ten percent across the board pay hike and generous offers to exceptional and standout employees are a good way to stem the flow of talent. Facebook and others, if they do indeed want these people, now have to spend cold-hard cash to lure people out of their cushy Google gig.

Of course, one could argue that what is good for the goose is good for the gander. The more cash big web companies offer as salaries, the more startups and others are pressed to offer higher salaries to their recruits, which in turn means that startups are going to need more money. More money means that tide might turn against the angels in favor of larger Sand Hill Road firms. A million-dollar angel round isn’t enough when you have to pay $100,000 or more in engineer salaries! In other words, the startup economics are going to change.

This is not good for startup founders either. Inflation means they need to raise more money, which will come at a cost: They will be giving up a bigger portion of their business to investors. Of course, higher valuations would make exits –- still few and far between –- tougher.

I think Wilson’s comment about “investors are showing up at the first meeting with term sheets” is particularly telling and indicative of the irrationality in the market. And the sad part –- it is only going to get worse.

Image courtesy of Flickr user joelogon

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I was as fascinated by the story of RockMelt cofounders Eric Vishria and Tim Howes as I was by their belief that they had a product (and technology) that would be able to find a solid footing in the crowded and hyper-competitive browser marketplace. To me, the story was the audaciousness of their ambition and why they started — of all things — a browser company.

Frankly, my last question to them was “who invested in the company.” It happened to be Marc Andreessen who is credited for creating the first viable and web-scale browser, which is a nice story hook, but it’s not the story. Unfortunately, many in the media reported the hook and stopped there. The focus of the news went from the browser, technology and the founders immediately to the investors.

Lately, it has become commonplace in the Valley to shift focus away from founders and put it on the investors. Some might argue that in case of RockMelt, it was the investor connection that made the story worthy of attention. (I would disagree with them.) To me those are the wrong reasons to pay attention to a company and its technology.

I have been writing about startups for a very long time — so long, that I can remember when Marc Andreessen was still in Illinois and long way from becoming the newest King of the Valley. And in the years that have passed I have written about some of the most memorable startups –- Ciena, Juniper, Cerent, Infinera, Google, Twitter, and Facebook –- and I have written about the forgettable ones.

Like most reporters during the bubble, in my early startup-focused writing, I lavished too much attention on the investors. My then-editor David Churbuck would call me into his office, sit me down and tell me that investors are a good way to judge if a company is worthy of a story. He would tell me that investment dollars and investors help you define a story, but they are never the story.

The more I paid attention to that advice, the better I became at choosing startups to write about. The technology was always the primary criteria, but in the late 1990s, David’s approach prevented me from getting too hopped up about here-today-gone-tomorrow Internet names such as Kozmo.com and Pets.com. At that time, investors had became the focus of attention (media and otherwise), and we all know how that ended.

While David’s lessons brought discipline when it came to evaluating startups, my deep appreciation for founders, I admit, came only after I started GigaOM. It is a tough life, where sacrifices and relentlessness are par for the course, no matter how big or how successful a startup becomes.

While investors are great counselors, one must never forget that it is founders and their team who build businesses. Jim Barksdale, CEO of Netscape and the founder of The Barksdale Group venture fund, once said, “The Main thing is to keep the main thing, the main thing.” When it comes to technology startups, it is the founders and the technology — that’s the main thing.

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PiCloud, a Sunnyvale, Calif.-based company that’s developing a python-based platform as a service (PaaS) has raised $1.4 million in its first round of funding. Investors in the company, co-founded by UC Berkeley graduates Ken Elkabany (CEO) and Aaron Staley, include Greylock Ventures, Kleiner Perkins Caufield Byers and Andreessen Horowitz.

PiCloud is joining the ranks of fast-growing start-ups, such as San Francisco-based Heroku, in providing a platform for app developers. Much like Heroku, PiCloud runs on Amazon Web Services platforms and is optimized for Python programming language. The company is going to extend its offering to Rackspace and currently offers installation for private datacenters.

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Does the world need yet another browser? Tim Howes and Eric Vishria think that it does, and that is one of the reasons why two years ago they started Mountain View, Calif.-based RockMelt, raised an undisclosed amount of funding from Andreessen Horowitz (and scores of technology luminaries such VMware co-founder Dianne Greene, Intuit’s Bill Campbell and Josh Kopelman) and hired away some of the best design and browser talent from other companies. Their socially aware browser will finally see the light of day today and will be made available as a beta version.

It’s a bold move by the two co-founders. They are entering a hotly contested market that is dominated by Microsoft (Internet Explorer), Google (Chrome), Mozilla (Firefox) and Apple (Safari). In addition, they’re launching a desktop browser — it works on Windows and Mac OS — at a time when the axis of computing is shifting to touch-driven mobile devices.

Vishria and Howes say the reason they started the company was that, while people’s usage of web and the services they use have changed, the browser itself hasn’t changed very much. “The modern web has evolved to a point where it needs a new kind of browsing experience,” said Vishria, CEO of RockMelt. “I can’t understand why the web browsing experience is so serial, especially when we have so much available processing speeds, memory and available bandwidth.”

He argues that today, everyone in the browser market is about minimal user experience, ease of navigation and speed. What RockMelt is focused on is around people’s web usage – which centers on consuming content, social sharing and social networking.

RockMelt’s quest reminds me of another grand attempt to take on the browser establishment, called Flock, which, despite great social aspirations, has had a tough go of it thus far. Vishria and Howes say that it is all about timing. Thanks to increased broadband penetration, the rise of cloud-based services and mainstream adoption of social services such as Facebook and Twitter, the browser itself needs to be social, said Howes, who worked at LoudCloud/Opsware along with Vishria.

“Most people communicate with a few friends and check only a few sites and we’ve made it easy for them to stay connected and get their information,” said Vishria. The browser integrates Facebook, Twitter and other social services right into the browser itself. At the same time, it makes it easy to add news feeds and other information sources. The browser, which is based on Chromium (the open-source project behind Google’s Chrome browser), requires you to sign-in with your Facebook credentials. Once logged in, you can add your favorite friends and news feeds on the left and right side of the browser. The browser makes it easy to update, tweet and share content via Facebook and Twitter. (See screenshots to get more details on the browser and its features.)

From the demos I saw, the 30-person company has done a fantastic job of integrating social features into the browsing experience. It has developed proprietary technologies (mostly HTML5-based) that make search a massively fast and more meaningful experience. The browser uses its built-in cache to pre-fetch, then pre-render a lot of content and make it available instantaneously.

However, it still has its work cut out for it; it’s entering a saturated market and will need to fight for attention. RockMelt wants to focus on mainstream consumers, but it has to contend with the harsh reality that people are slow to change and switch. Look at how long it took for Internet Explorer numbers to start sinking. Perhaps that’s why the company is focusing on getting the browser in the hands of many users before trying to build a business model. “Search is a good way for browsers to get paid, and we are thinking about other services beyond search, but that comes later,” said Howes. For now, the founders will be happy if a million people are using their browser in six months.

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There are few people in this world whom I admire as much as I admire Tim Westergren, founder of Pandora. It is not because he has the most successful company, or the largest or he is the richest. But mostly for his never say die attitude.

I have known Westergren for nearly ten years and for most of those years he has been fighting the odds. The past 12 months have been a dream for his company but the decade has been a walking nightmare for him. He has faced adversity and adulation with charm, poise and same easy smile.

“Every day I pinch myself; there is this nagging thought that this is not real,” Westergren said during our conversation. Of course, in past year or so he has been invited to top conferences, investment banks are wooing him, and Facebook and Apple both put him and his CTO Tom Conrad onstage at their big events. “I have a sense of unreality about it.”

I don’t blame him. Westergren has had a struggle to get to the top. If not battling the RIAA or pitching venture capitalists that would eventually turn him down, what kept him going was his belief in his idea of personalizing music. He shares his thoughts about building great teams, and inspiring faith and courage amongst his team members.

In this 30-minute, two-part interview, Tim shares the ups-and-downs of his journey. He shares lessons learned and where he found inspiration. And if you are a start-up founder, they don’t teach you what Tim has been through in some startup school. After you are done watching these videos, you would also want his company to succeed.

Lessons Learned:

1. Set-up your life professionally, personally and physically for a long time. You have to make it sustainable and not drive into a wall.
2. Don’t be self conscious about being an entrepreneur.
3. Entrepreneurs in their core team need a sales person. Someone who can tell the story and inspire people and get pulses racing because of your idea.

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