Calendar Frenzy, Google Now, and Apple’s “Anticipatory Computing” Problem

Earlier this week, I saw closed funding, which reminded me of all the calendar frenzy from a few months ago, and I realized I didn’t put my TC post from that week here, so here it is….

Now that the Mailbox sale to Dropbox is complete, let’s move on to the next native iOS app that everyone wants to replace: The Calendar. Yes, the calendar. Nearly every other conversation I had this past week included some chatter about all the new calendar apps (see the screenshot of my iPhone). Peeling back the layers on all these calendar apps and the herd-like interest in the space, however, reveals both challenges and opportunities that go much deeper than comparing mobile apps based on product features.

For those among us who use Android, Google Now is the type of anticipatory computing, powered by data and algorithmic learning, that enables a machine to guide us in life almost like an assistant would. On Apple’s iOS, however, there is no such thing like “Apple Now,” and as a result, savvy entrepreneurs are seeking to build that service as a third-party application. And, curiously, they’re using the mobile calendar on Apple to kickstart this game and using calendar “intent” to infer what to send to the user.

The motivation to write this post came as a surprise. You may have noticed that, over the past month, the amount of “smart calendars” and “intelligent assistants” has seemed to explode, all at the same time. Not too long ago, iPhone users had the chance to buy well-designed calendar apps likeCalvetica and Fantastical to have a better experience that what Apple’s native calendar app provides. I’d guess many Gmail loyalists on iPhone would love to have a native Google Calendar app, just as Google has shown excellence in iOS recently, but that doesn’t seem to be a high priority for now.

Back in the middle of 2012, I started using a service called Sunrise, which started on the web. It is a well-designed product that integrates your social networks and calendar to provide more context around upcoming meetings. More recently, Sunrise has built a clever iOS app that has many neat tricks, such as allowing users to go straight from Sunrise to Google Maps for iPhone, since our friends in Cupertino won’t let us set our own app-defaults for actions like these.

There are many players in this category, broadly speaking. Apps like Twist, which starts out with the goal of automating arrival alerts between meeting participants via SMS, or Cue (formerly Greplin), which presents your day’s information with more context on mobile, or Any.Do, a daily planner tying tasks together with the calendar, could grow into something larger at scale.

The big idea here is that systems like Sunrise and the others could, over time, start with making a better mobile iOS calendar and then grow into more anticipatory services, perhaps becoming a “Google Now for Apple.” And, as competition goes these days, just as Sunrise is drawing attention, we have witnessed a whole new crop of “intelligent assistants” on Apple’s platform, such asTempo (originated at SRI) and Leave Now, as well apps that we can only anticipate (pun intended) like Sherpa and Donna, which haven’t yet been released. (I have not tried Sherpa or Donna.)

These are all great apps, quite sophisticated in their feature offerings, but overall, while I find this particular entrepreneurial pursuit more than noble, I wonder about how much of an effect these apps could have within the iOS ecosystem given all the hurdles presented by Apple. Let us count the ways. App Store discoverability seems to be getting worse, not better. Most of these apps ask for access to your iPhone contact list and your iPhone calendar, and if users don’t allow those permissions during onboarding and registration, users will need to navigate their way into “Settings” to reactivate those permissions piecemeal. Even if an app can extract these permissions, many of them end up grabbing location persistently, even though some of them talk about access the GPS sensor in low-power mode. I’m of the belief that these always-on, location-aware apps are slightly ahead of their time and will require fundamental advancements in moile battery technology before consumers will give up their battery life. (Even apps as elegant and useful as Moves or Highlight, for instance, which passively grabs user location data throughout the day, may have their overall adoption impacted because of this reason.)

The larger question here, ultimately, is the delta between the efficacy and utility of a service like Google Now and what is possible given the current iOS environment. The way things stand today — and I know things could change, with advancements like Google Glass or an iWatch, etc. — recreating a “Google Now-like” experience on iPhone can only happen at the application layer, hence the competition listed above, but in order to really work for consumers, it will have to be an OS-level solution. Perhaps Apple assumed technologies like Siri could start to train iOS users to start giving voice-commands as inputs with a long-term goal of delivering intelligent outputs. I don’t fully understand the depth of the technological problems underneath this, but at least as a consumer, this notion not only seems far off in the future, it may also be a pipe dream.

This poses a curious opportunity and challenge for iOS app builders in this space. Even though they may have deep technologies and elaborate product roadmaps, all of the hurdles of getting to scale on iOS as well as all the permissions they require from the mobile operating system present a series of minefields. In order to compete with a service like Google Now, an iOS app would need continuous access to data in our email, calendars, address book, and location logs. And, with the acquisition of Mailbox fresh in our minds, that transaction may have set a bandwidth that any app in this productivity space could fetch on the market.

While I would never want to constrain a young team’s sights on more short-term goals — and I do sincerely hope one of these players emerge to be on everyone’s iPhones — the combined reality of (1) Apple’s legacy mindset with respect to its own mobile operating systems and (2) today’s acquisitive environment for iOS teams means startups in the calendaring or assistant space on iOS have a small but rare opportunity to sprint to grow (hint: use the web!). And, if successful, they may end up in Cupertino building this, because it’s only at the OS level — not app layer — that Apple could begin to provide more pervasive computing services and allow their machines a chance to to get better with time. In long-run, all of this poses a significant challenge to Apple’s iOS platform. Perhaps this is just one way to read the tea leaves. Unless something drastically changes in the meantime with respect to the App Store, battery technologies, or simply how Apple sets up their OS, I just don’t see any other way.