Rapportive’s “Social CRM” Gmail Plugin Makes E-mail Social Again

This is the fifth in a series of profiles of companies emerging this summer from Mountain View, CA-based startup incubator Y Combinator.

When Google launched Gmail five years ago, a lot of people were freaked out by the keyword-based text ads that appeared alongside e-mail messages. The idea that Google’s algorithms were “reading” your e-mail and serving up related ads seemed a little creepy and invasive. But now most people have gotten used to that, and have moved on to being freaked out about Facebook’s privacy settings. These days, most Gmail users never even glance at the ads filling the right-hand column.

Now there’s a way to put that space to more practical use. Rapportive, a San Francisco company that’s part of this summer’s crop of Y Combinator startups, makes a free browser plugin that replaces Gmail ads with digital dossiers on your contacts. If I sent you an e-mail message and you opened it in Gmail in a Rapportive-equipped browser, you’d see my whole social-media life spread before you: my photo, my title, my e-mail address, a list of my current and previous employers, my last three tweets from Twitter, and links to my Facebook, LinkedIn, and Flickr, FriendFeed, Google Profile, and YouTube accounts (see the screen shot below).

Rapportive - Sample SidebarThe idea is to give you real-time intelligence about the person you’re corresponding with—whether they be a friend, a source, a business associate, or a sales prospect—in order to bolster your rapport with that person (hence the company’s name, which is among the cleverer ones I’ve seen this year). “People love it because of the photos—there’s something very visceral about seeing a photo—and because of the tweets,” says Rahul Vohra, a University of Cambridge computer science graduate who is Rapportive’s co-founder and CEO. “They can talk immediately about something someone has just said. It shows you really care because you are following them on multiple channels.”

Putting a contact’s photo and personal and professional details right alongside his or her e-mail messages isn’t a brand new idea. San Francisco’s Xobni makes a popular add-in for Microsoft Outlook that does many of the same things, and Seattle-based Gist makes a Google Apps gadget that lets Gmail users click on contacts’ names to see profiles. But Rapportive is more automatic, filling the right sidebar with contact details without requiring any action on the user’s part. And when you think about it, the idea makes perfect sense: e-mail is the original, and still dominant, “social media” technology, so when you’re reading or writing messages, it’s useful to have all of the Web’s miscellany about your correspondents gathered up on the same screen. (There’s also a box that allows you to save personal notes about each contact.)

I’ve been using Rapportive’s tool since April, well before the company announced that it was part of Y Combinator, a startup school in Mountain View, CA, that provides several months of mentorship and networking assistance in exchange for a small amount of founding stock.

Along with Y Combinator’s investment, the startup has raised $1 million in seed funding from an impressive, bicoastal list of venture firms and angel investors. The venture investors include BoldStart Ventures, Charles River Ventures, 500Startups, Kima Ventures, and Zelkova Ventures, and the angels include Paul Buchheit, Scott Banister, Jason Calacanis, David Cancel, Shervin Pishevar, Naval Ravikant, Roy Rodenstein, Dharmesh Shah, and Gary Vaynerchuk.

Because Gmail runs inside a Web browser, meaning it’s really nothing more than a bunch of HTML, style sheets, and JavaScript, it’s a straightforward matter for Rapportive and other startups to write plugins that manipulate the appearance of the Gmail page—and there’s not a thing Google can do about it. So far, there are Rapportive plugins for Chrome, Firefox, and Safari, and Vohra says the three-man startup is working on a plugin for Apple Mail.

Vohra himself has the sort of hybrid background—heavy on both computer science and entrepreneurship—that makes him a natural as a social media startup founder. He says he’s been coding since age 9, starting with BBC Basic, the language developed for the British Broadcasting Corporation’s Acorn home computer in the early 1980s. He finished his computer science degree at Cambridge in 2005, then went on to do PhD work, focusing on a computer vision program that transformed printed Sudoku puzzles into digital versions that users could solve on mobile devices. While in graduate school, he became deeply involved in Cambridge University Entrepreneurs (CUE), which runs the largest student business plan competition outside of MIT. After becoming president of the organization, he took an intermission from his PhD work to spend all his time fundraising for the group, eventually collecting more than £100,000.

The experience convinced him that he wanted to help run a company—so he left the university and joined an angel-funded startup called mo.jo, which built a software platform to help large organizations run business plan competitions (just as Vohra had at CUE). One of Vohra’s colleagues at mo.jo was Sam Stokes, and at Red Gate Software—the Cambridge database company and incubator where mo.jo was based—Vohra also met Martin Kleppmann, who’d built a Web app testing startup called Go Test It. After winning the non-profit Cancer Research UK  and the UK Ordnance Survey as flagship mo.jo customers, Vohra spent about six months working to launch an online game based on the works of Steven Erikson, the Canadian author of a popular fantasy series called The Malazan Book of the Fallen. But after Erikson backed out of the deal around January of this year, Vohra was back to square one. That’s when he settled on the idea for Rapportive.

“This time I said, ‘Let’s build something that I really want,'” Vohra says. “My e-mail client is Gmail, and what I really wanted was to see what people look like and see what they do and see what they’re saying on Twitter and what they’re doing online, and be able to store notes about them.” He signed up Stokes and Kleppmann to help build a company around the idea, which, he says, had sprung in part from a concept Kleppmann had shared about wanting to make customer relationship management tools like Salesforce.com more social: “I had never heard the phrase ‘social CRM’ before, but as soon as Martin said it, something clicked inside my brain, and I could instantly see a product.”

Rapportive’s public launch in March was actually inadvertent. Vohra had applied to Y Combinator, which “wants to see a prototype before you apply,” he recounts. “We put up a working prototype on the first of March. And on the second of March, somehow the press found it. TheNextWeb found the first version and reported on it, and then it got picked up by ReadWriteWeb, and then Lifehacker, and then Twitter went insane. We had 10,000 signups in the first 24 hours, and in the coming weeks, top-tier VCs started calling us.”

Vohra says the premature launch, which is also described on the Rapportive blog, was “completely accidental,” but it had the happy side effect of winning Rapportive early admission to the Mountain View incubator. “We called up Y Combinator on Skype and basically said, ‘We could raise a seed round at a much higher valuation, but we want your money because we want to be part of the process—we need your help with incorporation, lawyers, the press, recruitment, the brand in general. Y Combinator is by far the best way to do all that.’ They invested over Skype, which was kind of cool, and we all got drunk that evening.”

Rapportive benefits hugely from the Web’s new openness. Companies like Google and communities like Stack Overflow offer programming interfaces that make it easy to grab members’ profile information for the Rapportive sidebar, and the startup gets additional information from data providers like RapLeaf, a San Francisco startup that scours the Web for personal and demographic information about consumers. The startup gives users the ability to tailor the information that other Rapportive users will see about them, which means that the more people sign up for the free sidebar, the better its data will get.

Rapportive’s Gmail sidebar represents only the first step in a much larger strategy, according to Vohra, but the company isn’t quite ready to talk about the bigger vision, he says. Meanwhile, he says customer feedback shows that people are using the sidebar data in a variety of ways. These include:

Hiring. “I had a person say ‘I’m hiring a new associate, and what people say on Twitter is far more telling than what they say on their CV.'”

Finding roommates. “Three or four people have said, ‘I’m renting a room in my house, and being able to filter people on the basis of their Facebook link is far more efficient than doing the 10-minute phone intro.'”

Sales. “When I was doing a lot of business development and sales for CUE, I was dealing with a lot of people, and it’s the kind of thing I would have found useful. You have to remember who people are.”

Networking. “We’ve had people come back and say, ‘I go to these networking events and collect hundreds of business cards, but I don’t remember who anyone is. Seeing their photo and location and LinkedIn profile reminds me who this person is, and puts the context back into my head.'”

Pruning your own social-media profiles. Because Rapportive searches the Web for details about you and your correspondents, it can turn up information you may have forgotten about: “One user came and thanked us for alerting us to his forgotten Bebo account.”

And Vohra’s “intermission” from graduate school? It’s now permanent, and Vohra says he has no regrets. After leaving mo.jo, Vohra says he had an important conversation with his mother. “She says all kinds of things like ‘Failure is the difference between expectation and achievement’—I think she spends hours coming up with these things. This time, she challenged me to think about the things I’m passionate about. Games, biology, programming. She said, ‘Do something you find easy and that other people aren’t good at.'” For Vohra and his colleagues at Rapportive, that’s helping people build social connections through software.

Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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