Meet the guys behind the iPhone’s best calendar app

It’s not a surprise when a company with copious resources like Google(s GOOG) builds a better iPhone search or mail app. But it’s far more interesting when small development teams are beginning to build better core iPhone software than Apple.(s AAPL) On of those is Flexibits, a two-man team that has built the best basic calendaring app for the iPhone.
The app, called Fantastical, is available for both the Mac ($14.99) and the iPhone ($3.99). The iOS version of the app arrived about a month ago, and received glowing reviews. Downloads spiked soon after: the iOS app managed to beat Angry Birds Star Wars for a time as Apple’s No. 1 paid iPhone app.
screenshot-3-neweventWhat makes Fantastical so instantly usable and popular is its simplicity. It makes it easier to add events to your calendar — on the Mac it’s a quick dropdown from the menu bar, and on iPhone you click a “+” button — and features a natural language parser. Put together, those features allow users to quickly type in a single box, for example, “Skype with Ian 1/17 at noon” and have the item added to your calendar for 12 p.m. on Jan. 17. That’s it. No flipping dials, hunting for the correct calendar page or setting the time as on Apple’s calendar. It’s also refreshing for a third-party app because it doesn’t try to do too much. The app only does one thing: calendaring; and it does it really well, without trying to be also a contacts repository or a task manager.
The duo behind Fantastical is Michael Simmons and Kent Sutherland. They do great work together, Sutherland told me, because in many ways they are polar opposites. Simmons is 41, lives in San Francisco’s East Bay, and has been coding, designing and marketing products at respected Mac software companies Ambrosia and Cultured Code. Sutherland is a 25-year-old Boston resident just a few years removed from getting his Bachelor’s and Master’s degrees in quick succession. Simmons talks a lot, and fast; Sutherland is a bit shy, and more of a listener. Simmons does the business development, marketing and design and user experience, while Sutherland does the bulk of the coding. They contract the services of Wolfgang Bartelme to build Fantastical’s graphics. Together, Simmons and Sutherland both conceptualize and very carefully choose what app project they want to tackle.

Michael Simmons

Michael Simmons

Flexibits is self-funded — and profitable — according to Simmons. They have received offers of outside investment, but he says right now “it’s not something we need.”
Fantastical is the first collaboration that made it to the App Store since Simmons pinged Sutherland and asked him if he wanted to be his partner in the company he was starting. The Mac version was well received, but the iPhone app, launched just after Thanksgiving, has drawn superlative praise. The Verge called it “the iPhone calendar app we’ve been waiting for.” Flexibits doesn’t give out download numbers or active user numbers.
Kent Sutherland Flexibits

Kent Sutherland

Their arrangement is a bit unusual among the hotshot iOS development teams out there, mostly for its bicoastal, multigeneration arrangement. But the pair is doing great work, mostly because of the balance they provide each other, they said.

The origin story

Simmons had been a big fan of Sutherland’s for years, he told me during a Skype session from somewhere in Italy last week. They’d become online buddies after Simmons started submitting bug reports for a piece of Mac software he found online created by Sutherland. When Simmons was ready to start his own company after leaving Cultured Code (where he worked on another beloved Mac app, Things) he asked Sutherland, who’d just recently gotten his Master’s from Cornell, to join him.
The two started tinkering with a contacts app idea, but it wasn’t until Sutherland mentioned he had a natural language parsing engine he’d worked on in school that they had a lightbulb moment for a different app.
Sutherland wasn’t decided on what to actually do with the language parsing engine. But he knew what he didn’t want: “In school there’s these cool things people work on then they get sucked into some huge enterprise [company],” he told me last week. He wanted to build his idea for consumers. A small, indie dev shop, however, represented promise.
Simmons knew exactly what to do with it, he said. “I was certain calendaring was the way to go. I just knew that was the problem to solve” especially if you could make events quickly.
The Mac app came first in May 2011. The iPhone app didn’t appear until the end of 2012. The delay happened because they didn’t know how to redesign the Mac app for the iPhone in a way that was compelling enough for a smaller screen on a mobile device.
Sutherland hit on it first: the Dayticker, which is a sliding calendar bar across the top of an iPhone screen that lets users scroll quickly between days. After deciding on that angle, it took them just “a few months” to get it ready for submission to the iOS App Store.

What Flexibits can do that Apple can’t

The Dayticker, and the event entry are so simple; you wonder why Apple can’t do something like that. Sutherland believes it has to do with a different set of constraints over the Flexibits team and Apple’s developers.
“We’re not Apple. They have to make sure it’s exceedingly obvious for everyone [to use an app] and there’s a button in a visible place for everyone,” he said. “As a third-party app developer you can afford to take a few more chances and try something a bit different.”
Apple also has to make something that ships on time and that works. These guys don’t feel compelled to churn out apps or meet anyone’s deadlines. They’re far more focused on making apps that solve specific problems in daily life.

Fantastical for Mac

Fantastical for Mac

For them, that doesn’t necessarily mean mobile either. Mobile is the future, of course. But Sutherland likes the experience of developing for the desktop because “there’s more to think about” and complex problems to solve.
So for those waiting for Flexibits’ next release, don’t be surprised if iOS isn’t the platform they target. It could be for the Mac, or iOS or something not related to Apple too. “We are considering other platforms,” Simmons told me. “We are Apple guys for sure, but we want to make software that betters other people’s lives.”

Simmons was apologetically vague about details of the team’s next collaboration, other than a date: sometime in 2013. But their team of two (or three) could be growing soon too. While updating Fantastical Flexibits plans to to get back to the standalone contacts manager application it put on hold to build Fantastical.
“This year we’re thinking about hiring some people or working with more contractors to open up cycles to do more products,” Simmons said. “We’ll have more than the contacts and address book app this year.”

And if things keep going the way they are, there’s a good chance what they build will need strong consideration as a replacement for your default Contacts app.