UpTo: The Social Calendar App That Learned From Plancast’s Missteps

Have you ever jumped online to check your Twitter feed only to see that your friend just posted a Foursquare check-in at a restaurant you left twenty minutes ago? And then been frustrated that you hadn’t known ahead of time that your friend was going to be dining in the same spot as you? After all, you’ve had her birthday card laying in the bottom of your purse for a week but you’ve both been too busy to arrange a proper meet-up. Stopping by her table at dinner would have been just the thing, but alas.

Well, Greg Schwartz feels your pain. He’s the co-founder and CEO of the Detroit-based UpTo, a new startup with a free iPhone app that turns the daily calendar into a social network. He put the team behind his app together last year after he noticed a “future void” in social media. “Facebook is about cataloging the recent past and Twitter is about capturing the present tense,” Schwartz explained. “But nobody captures what’s going on hour from now, or a week from now. I saw that as a massive opportunity.”

UpTo allows users to share their calendars by adding friends from Facebook or their phone contact lists and arranging them in groups—such as “work” or “family”—for sharing. In just a few taps, users can share with their Facebook and Twitter networks, add new events to existing calendars directly from the app, and view calendars using a heat map overlay to quickly see which days are the busiest. Users can choose which group views calendar entries using hashtags, and can route calendar entries to Twitter or Facebook by using the tags #t and #fb. UpTo works with any calendar that syncs to the iPhone, be it Outlook, Google Calendars, or iCal.

The point of UpTo, Schwartz says, is to allow users to invite their friends and associates into another layer of their lives without changing existing behavior. Since users have the ability to comment on one another’s calendar items, Schwartz thinks the resulting conversation may end up being most exciting aspect of UpTo. Of course, to optimize UpTo’s features, a user’s contacts must also download the app, but they don’t need to use a certain type of calendar to participate. For now, UpTo is only available for the iPhone, but the company will launch an Android version this summer and a web interface after that.

UpTo isn’t the first mobile app to take the to-do calendar into the social realm, but it may be the first to meaningfully monetize it. Schwartz’s goal is to build an “intent graph”—a broad term for mapping future-looking information, whether it’s your son’s dental appointment, a pitch meeting with investors, or the Super Bowl broadcast. If all goes according to plan, UpTo users will see a stream of events tailored to their interests—say, a football broadcast or a networking happy hour—and will be able to push a button and add it to their calendars before sharing it with their networks. Schwartz envisions sponsored events being a significant source of revenue in the future.

The first big offering in the calendar socialization space, Plancast, was launched three years ago by a former TechCrunch reporter. It faltered shortly after launch because it wasn’t able to scale beyond the early adopter crowd and achieve critical mass. Plancast tried to modify its product to offer better functionality, but it ultimately failed to grow registration sufficiently and engage users on a day-to-day basis. The human tendency to balk at commitment and procrastinate without incentives also came into play.

Schwartz isn’t particularly worried that UpTo will go the way of Plancast because of a few key differences. Plancast suffered from a low frequency of sharing—users were sharing primarily big events with lots of people, he says, whereas Schwartz hopes UpTo users share everyday events with small groups of people. Plancast didn’t offer users the ability to divide calendar recipients into groups, which meant you were sharing Timmy’s dental appointment with work colleagues and staff meetings with spouses. Schwartz also says he’s spoken to Plancast’s former CEO Mark Hendrickson about some of that company’s missteps, and going mobile right out of the gate was one that UpTo has already taken to heart.

“Really, the only similarity between UpTo and Plancast is that both of them look forward into the future,” Schwartz adds.

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