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

9/30/08Follow @wroush

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 fill it in with what you could be doing tomorrow, what your friends are doing tonight?”

Vakil went off and built a prototype that would do just this. But Ambient ended up with a new CEO, Carl Yankowski, who wanted to place safer bets. “The clock was more of an experimental project—a Media Lab type of thing,” Vakil acknowledges. He also realized that while an analog clock might be good at showing a user what’s happening in the next 8 to 12 hours, “It’s never going to tell you that Coldplay is playing in two weeks when you’re going to be in San Francisco and you might be able to get tickets.”

A calendar seemed like a more natural setting for such information. Vakil wrote a patent application around the idea, and rounded up a few programmer friends to implement it. The new startup decided to enter the fbFund competition shortly after the fund was announced in September 2007.

How LuckyCal WorksPart of the attraction of working with Facebook was that the Facebook Platform, the set of programming interfaces open to outside developers, already made it easy to grab critical data from users’ profiles, such as the dates, durations, and locations of events on their calendars. Another encouraging sign, says Vakil, was that the fbFund screeners “were interested not just in how we were going to make things better for Facebook users but ultimately how we were going to make money. Most [developers] say they’re just going to put ads up, which is unimaginative—it’s really just saying that you don’t know how you’re going to make money. But they liked our business plan, and thought it was very complementary to Facebook’s.”

After a rigorous interview process, LuckyCal won the full $250,000 it had requested—a real achievement, considering that more than 1,000 teams of developers applied for the grants. The money has remarkably few strings attached—it’s a grant, not an equity investment or a convertible note. “It’s acted like a angel round for us,” says Vakil. “Otherwise I would have been out there raising angel funding from others, which is much more time consuming. Hopefully, we will coast on this through getting some customers and, if necessary, raising some venture capital at a later point in our product development.”

Right now, LuckyCal makes money on affiliate commissions—when people buy tickets to nearby concerts through Ticketmaster, or when they act on relevant hotel or airline offers culled from sites like Expedia and Kayak. Later, says Vakil, the company hopes to sell its software as a plug-in for personal-information-management and enterprise scheduling systems. The idea is to help big companies be more efficient about travel planning—by showing them in advance, for example, that two sales representatives are planning trips to the same area, allowing them to either team up or consolidate.

“IBM has 380,000 employees and 200,000 of them travel every year,” says Vakil. “Say that the average trip costs $2,000. If you could, conservatively, save every employee who travels one trip every two years, you’re talking a savings of almost $200 million a year. Even for IBM, that’s real money.”

LuckyCal has a fancy buzzword for its calendar-matching technology: “predictive presence.” But in the end, says Vakil, all the software really does is “look at where you are and where other people are, then look at how those two overlap in time and in space.” There’s no luck involved: just lots of data, all of which is already sitting there, waiting for someone to connect it.

Wade Roush is a contributing editor at Xconomy. Follow @wroush

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