LuckyCal, Winner of Facebook Grant, Makes Your Calendar into a Connector

You get home from a big business trip to San Francisco, you’re talking with a friend from out of town, and you find out that he was just there too. If you’d known, you could have met up! It’s a common scenario—and it shouldn’t happen as often anymore.

After all, you probably keep an electronic calendar that includes details about your upcoming trips. And most calendars these days allow you to share your appointment data with other people’s calendars, over the Web or corporate networks. There ought to be a central exchange where your calendar program can go to find out whether any of your friends (or colleagues, or potential clients or customers) are going to be in the same area as you at the same time.

Well, now there is. It’s called LuckyCal, and it’s being built by a Lexington, MA-based startup that’s one of the first 10 companies to receive a grant from Facebook’ $10 million “fbFund.” Announced last year, the fbFund is run by Facebook with money from Accel Partners and The Founders Fund, and is designed to support independent developers working on applications for the Facebook Platform (the subject of my interview last week with Facebook senior platform manager Dave Morin). LuckyCal got the largest possible grant from the fbFund: $250,000, to be doled out in installments as the startup meets usership milestones.

But, while LuckyCal’s Facebook application is an important part of its offerings, you can use the service even if you don’t have a Facebook account, by giving it access to your desktop- or Web-based calendars and address books and inviting friends to share their own data. LuckyCal’s matching algorithms suck in all this information, along with public event listings from sources such as Ticketmaster, and spit out what the company calls “lucky” events: confluences that you can then decide whether to act upon. Say you’re going to Minneapolis-St. Paul next weekend. LuckyCal might see from your address book that you have a cousin there, and suggest that you give her a call; and it might know from the interests you’ve listed on your LuckyCal profile that you love public radio, and send you a link to purchase tickets to a live broadcast of “A Prairie Home Companion.”

When I first heard about LuckyCal’s service, it reminded me of 1990s-era predictions about “intelligent agents” that would scour the Internet, making your travel arrangements, negotiating appointments, doing your holiday shopping, and the like. A full-blown agent would require a level of artificial intelligence that’s still way beyond what computer science can accomplish. But LuckyCal does something very similar, just by crunching together the standard data that can be extracted today from productivity applications like Outlook and iCal and Web platforms like Facebook and Gmail.

Sanjay Vakil, CEO and co-founder, LuckyCalIt’s a no-brainer, in a way. But nobody had done it. “Calendars have been around for a very long time,” observes LuckyCal’s 37-year-old CEO and co-founder Sanjay Vakil, a Canadian-born entrepreneur and software architect who’s a veteran of local startups like Ambient Devices and PatientKeeper. “Electronic calendars have been around for a reasonably long time. And online calendars have been around for 8 to 10 years now. Yet nobody has tried to do this—to solve the simple problem of ‘Here’s where I’m going, show me what’s available while I’m there.”

Facebook, where members are already eager to make connections, is an obvious place to try out the model—and so far, a couple hundred Facebook users have signed up for LuckyCal. But ultimately, Vakil sees the software as something that could go beyond the social-networking crowd to become a money-saving tool for big organizations whose employees travel regularly. The fbFund grant comes at a key moment, helping the startup get its idea working first in a friendly environment (and perhaps helping it to earn a bit of money on Ticketmaster commissions along the way). But long-term, Vakil says, the business model is more about licensing LuckyCal’s services to big corporate customers.

Vakil says he’s been thinking about better ways to interact with event information for several years—ever since he worked at Ambient, a Cambridge, MA, startup that sells wireless information displays such as the Ambient Orb, which glows red or green according to the direction of the Dow Jones Industrial Average, and the Ambient Scorecast, which shows the progress of baseball games, hit by hit. (Vakil wrote the code for the latter device.)

“LuckyCal came out of a meeting with David Rose,” Ambient’s director and chair, Vakil says. “We had this idea for the Ambient Clock—a device that would take calendar information and show it on an analog wall clock. If you had an appointment between 2:00 and 3:00 it would fill in that pie piece. But we looked at the data real people put into their calendars, and on average it’s only about one event per day. What do you do with the rest of the clock? Why not try to … Next Page »

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

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