Noteleaf Seeks to Sync Up Online Calendars, Contacts, For Meeting Prep On-The-Go

This is the second in a series of profiles of Y Combinator Winters 2011 (YC W11) startups.

Whatever your thoughts about modern technology and whether it’s making life better or just busier, you can’t say that no one feels your pain.

In fact, hundreds of new startups pop up every year to fix perceived pain points in the way we organize our digital lives—and no small fraction of them seem to come from Y Combinator, the Mountain View, CA-based venture incubator. Yesterday, I wrote about Taskforce, a YC Winter 2011 company that has created a Gmail widget that helps you regain control of your inbox by converting e-mails into to-do items. Today, I’m putting the spotlight on Noteleaf, another two-man Y Combinator startup with a service that sends you key details about your business contacts when you need them most: right before you meet with them.

Noteleaf is a simple, set-it-and-forget-it tool that leverages your existing online calendar and social networking accounts. When you sign up, you give the service your cell phone number, as well as permission to connect to your Google Calendar and your LinkedIn account. Then the company’s software scours your upcoming appointments for the names of the people you’ll be meeting with, and looks up those people on LinkedIn.

Exactly 10 minutes before a meeting, Noteleaf sends you a text message with a link to a mobile Web page with your contact’s profile. The page includes their photo, work history, recent tweets, a link to your e-mail correspondence with that person and a Google Map showing the location of the meeting. It’s like that no-nonsense secretary Mrs. Landingham on The West Wing, handing you a briefing book just as you go into your next big negotiation.

“It’s especially useful for people who book a lot of meetings,” says Noteleaf co-founder Jake Klamka. “Maybe you booked this meeting two weeks ago. You didn’t need the info an hour ago, but now it’s 10 minutes before the meeting, and you are rushing, and you really need it. We are going to present it to you in one compact, quick-to-review package.”

I’ve tried Noteleaf and it works well—although, as with all software, things can occasionally go haywire (more on that in a moment). Perhaps the coolest feature is that once you’ve created your Noteleaf account, you never have to touch it again. The system checks your calendar on its own, and you don’t have to do anything special to prompt a meeting reminder. The company’s driving philosophy, Klamka says, is “don’t make people do any extra work, and send them the right information at the right time.”

The service has some limitations, which mostly reflect how new it is—Klamka says Noteleaf, like most YC companies, adheres to the lean-startup mantra of “launch early and get feedback.” So far, the service can only connect with your Google Calendar, so if you use Apple’s iCal or Microsoft’s Outlook as your datebook, you’re out of luck (unless you do a bit of extra work to sync Google Calendar with your existing calendar application). And the 10-minute warning time is fixed—you can’t change it to, say, 30 minutes or 5 minutes.

But what’s remarkable about Noteleaf is how much goes on behind the scenes to make sure you’re armed with the key information you need before each meeting. In particular, in a reflection of no-extra-work philosophy, the software uses some pretty sophisticated tricks to read your standard calendar entries and figure out who you’re meeting with. It makes life easier for Noteleaf if you include a contact’s full name in a calendar entry, but it’s not necessary.

Klamka was trained in math and high-energy physics, and he says that work involved learning how to write machine-learning algorithms that extract the signal from the noise in physics experiments. Co-founder Wil Chung has a computer science background and has worked on similar signal problems, Klamka says. “Whereas somebody else would have seen this [calendar] problem and said, ‘I am going to have the user enter an e-mail address [for every meeting participant], we thought we could do something interesting by using algorithms and natural-language processing and heuristics to extract the signal in this. We want to add value without you having to change your behavior in any way.”

That means, first, identifying the names in calendar entries, and then retrieving the right profile information for that name. If you type “Lunch at Four Seasons with Simon” into your Google Calendar, in other words, Noteleaf has to figure out not only that Simon is the person you’re meeting with, but which Simon it might be, based on the people in your Gmail and LinkedIn contact lists.

Most of the time it works great, but like any machine learning system, Noteleaf deals in probabilities, which means sometimes it makes mistakes. In fact, while testing the service before writing this article, I provoked Noteleaf into an unintentionally hilarious one. I created a meeting in Google Calendar called “Fake meeting with Jake Klamka.” When the text message for the fake meeting arrived, it contained a link to a profile for Caterina Fake, the co-founder of Flickr and Hunch.

What might have thrown Noteleaf off—to the point that it didn’t recognize the name of its own co-creator—was the fact I’ve exchanged many e-mails with Caterina and am connected with her on LinkedIn, whereas I had just met Klamka. And it didn’t help that one of the people in my contact list has a last name that’s also a common word. “One of our biggest challenges in name recognition are cases exactly like this,” Klamka said after I reported the error to him. “There are a number of things we can do to make it even better. We hope to take into account name clusters in the future, which would have helped detect the right name in this case, because ‘Fake’ was by itself, whereas ‘Jake Klamka’ had two name-like words in close proximity, so we could have adjusted for that.”

In another slight wrinkle, the text message with the Fake link arrived at 2:57 pm, just three minutes before the scheduled 3:00 pm meeting instead of the usual 10. Klamka says the delay was a sign that I’d just signed up, so the system was busy ingesting all of my future meetings and didn’t get around to processing the 3:00 pm meeting until it was almost too late. It may also have been a sign of Noteleaf’s burgeoning popularity—the startup’s system has been under strain since March 17, when a number of stories about the company appeared in VentureBeat, ReadWriteWeb, GigaOm, Fast Company, and the New York Times.

Noteleaf started off with Google Calendar because Google offers outside programmers the best set of tools for connecting with its systems, Klamka says. In the future, the company may develop ways for people to connect to iCal, Outlook, and other calendar systems. And Klamka says he and Chung have much broader ambitions. “For us, where this gets really exciting is around that philosophy of having the right information presented to you at the right time even though you haven’t asked for it,” he says. “Right now, we’re focused on meetings, but there is a lot of room to leverage whatever information is out there.”

While Noteleaf currently delivers information at a fixed time, for example, it could also use other criteria such as your location as the prompt—sending a text message when you get within half a mile of your meeting location, say. “Our phones are becoming like little mini-sensors, and there’s no reason why an app like this couldn’t use information from the phone itself to figure out what is the right time and the right information from the context,” Klamka says.

Noteleaf is free for now, but the startup might eventually impose a premium fee on “power users” who make frequent use of it, Klamka says.

Whether the services Noteleaf and its Y Combinator brethren are building make sense as businesses is, to me, an open question. In their current form, Taskforce and Noteleaf might make more sense as features of larger systems than as standalone products. Taskforce would probably work even better if Google bought it and baked it into Gmail, for example. And it’s easy to imagine a company like Google, Apple, Microsoft, or Research In Motion snapping up Noteleaf and adding the meeting-notification feature to their mobile operating systems.

But whenever I put this question to Y Combinator entrepreneurs, the answer is the same—they aren’t building to flip. Klamka says he and Chung want to build a big company of their own, the way a select few Y Combinator alumni like Dropbox have. “We don’t know yet what form it will take, but within this vision of the right information at the right time pushed to the user, we think there is a ton of room to grow,” Klamka says. “Dropbox, for us, is an incredible inspiration. It’s something that started off as a very useful tool that just made [the founder’s] lives a whole lot easier, and now it’s growing like crazy—and not only growing but broadening.”

Wade Roush is the producer and host of the podcast Soonish and a contributing editor at Xconomy. Follow @soonishpodcast

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