Earlier in May, word got out that Apple is planning to invest $1 billion in a server farm. The facility, to be located in the State of North Carolina, will follow a similar (albeit smaller) $600 million undertaking by Google. As could be expected, analysts, bloggers, and the Twitterverse the world over speculated about the possible uses for the investment, but I don’t think anyone hit the nail squarely on the head. I think Apple will use its new server farm to completely cut the cord between its iPhone product line and the desktop. And it will do so in a big way.

Since the iPhone is the premier mobile device made by Apple today, it gives us an idea of what features will migrate down to the iPod line in the future. So let’s take look at the current state of the iPhone and its interaction with the desktop computer. For the most part, an iPhone will synchronize the following items with iTunes: mail accounts, contacts, calendar appointments, bookmarks, stored passwords, user names, and apps. Most of these items can be synchronized today without ever plugging the iPhone directly into a computer: more specifically, contacts, calendar items, and mail can all be synced over-the-air (OTA) with web-based applications from Google (calendar, contacts), Yahoo online services, Microsoft Exchange, as well as Apple’s own MobileMe.

But let’s not forget the original reason for plugging an iPhone directly into a desktop system: music, video, and podcast synchronization. And here’s where the server farm comes into play: I believe that

Apple will use its new $1 billion server farm to back up and sync music, video, and podcasts over the air to and from users’ iPods, iPhones, and iTunes libraries.

Why would Apple want to do this? For starters, it would eliminate the need to plug an iPhone into the computer to perform a sync. Imagine your iTunes library on the desktop being synced to Apple’s servers – much in the same way that contacts and calendars sync to MobileMe today. Since the iPhone will also sync with these servers, all added libraries will stay up to date automatically, whether it’s iTunes running on Windows 7, an iPod Touch connected via WiFi, or an iPhone connected via 3G (AT&T allowing).

Apple is a company that’s well-known for taking an already-existing idea and executing with pure perfection. A few examples: the iPhone was not the first touch-screen smartphone, the iPod was not the world’s first digital music player. But both are nothing short of awesome when it comes to execution: the marketing (market targeting, pricing, sales channel/distribution), ease-of-use, and the sheer “cool” factor that goes along with owning these devices. Apple will make a complicated and confusing technology (synchronization) accessible to the mainstream audience via sexy devices (iPhone, iPod) and simple software (iTunes).

Apple will also achieve a side benefit here for the public good: since a merged copy of the user’s iTunes libraries will live on Apple’s servers, the user will have a back-up in the cloud and not even realize it’s there (until a hard drive goes bad or an iPhone gets dunked in a swimming pool) . In an era where back ups are crucial – yet (unfortunately) implemented by very few – this is a major benefit.

On top of that, it would also makes sense that Apple would enable online access to the stored media from any internet-connected machine. Here’s a use-case scenario: if I’m away from my iMac and the battery in my iPhone’s is drained, I can use my friend’s machine to stream my backed-up media collection straight from Apple’s web-based interface.

It would make sense that Apple bundle this sync functionality with its MobileMe web services package. At the present time, the service provides 20GB standard, with 40GB and 60GB packages available for $49 and $99, respectively. Apple could easily upgrade the default amount of storage to 40GB and provide upgrade plans of 80 and 160GB for a fee. Considering that storage prices are falling, the only thing Apple would have to keep an eye out for is bandwidth – nothing that the company can’t overcome.

So how far off is this dream of the ultimate tech zen? Considering that Apple is still in the early stages of building this data center, I’d put it about a year out. But with calendar, contacts, and whatever other data being synchronized over-the-air, syncing music, movies, and podcasts seems to be the next logical step! Sync FTW!

Join us on today’s TNR Podcast to hear us discuss this story, along with the day’s top tech news, in further detail. We broadcast LIVE at 5:30pm EST Monday – Saturday. Can’t join us live? Grab our RSS feed and subscribe!

NuevaSync logo courtesy of NuevaSync

As some of you may know from my previous posts, I have been an outspoken complainer about the lack of wireless over-the-air (OTA) calendar synchronization options for the iPhone.  Simply put, unless you have access to a Microsoft Exchange server (medium to large corporations do) or pay for MobileMe (with which you can’t share calendars with friends and family), there is no easy, intuitive, or otherwise streamlined method to synchronize a web-based calendar such as Google Calendar with the iPhone.  Luckily for us iPhone users, this has finally changed thanks to one company: NuevaSync.  Hit the Read More link to find, well, more!

NuevaSync is a service that synchronizes your iPhone with Google Calendar.  You give it your Google username and password and then configure the iPhone to sync via Exchange to the NuevaSync servers.

Yet here is where NuevaSync really shines: whereas in months past the service lumped all of your calendars into one “main” calendar which was blue in color, the new killer feature released a few days ago

Image courtesy of NuevaSync

color-codes your calendars the way Google Calendar or iCal do!  So you can now view, add, or delete appointments by calendar.  This is a welcome addition to those like myself who have many calendars.  I have three calendars for work, one for family, one as a main schedule, and one for working out.

Currently, NuevaSync is only able to synchronize a maximum of eight calendars this way, but support for more calendars is coming.  Because NuevaSync uses the Exchange system built into the iPhone, changes are pushed to your phone!

I’ve been using it ever since the service was released (around summer of 2008) and was gleefully surprised when my calendars had color all of a sudden!  The service is currently in beta and free for everybody, although a paid version might be on the way in the future.  The NuevaSync FAQ states that there will always be a free version.

How it works

Just in case you were curious, the service works in a creative way: it pulls in your GCal data into its servers and outputs it OTA to the iPhone.  This process is reversed for changes made from the iPhone.  NuevaSync also has the ability to sync Google and Plaxo contacts and works on the iPod Touch as well as some Windows Mobile® based devices.

I will be discussing this post along with the “state of sync” topic on the TechNest Report podcast this Friday.  So please tune in for more in-depth commentary on the subject.  Show is out at 3:00pm EST every Friday!  Live shows coming soon!

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Computer-based calendaring: the background

Today’s calendaring applications help us coordinate our work (and play) time.  For some time, calendaring was something we did on a desktop-computer basis.  These “high-tech” solutions, as some would describe them, offered many benefits over traditional paper-and-pen calendaring and planning solutions.  The most significant of these benefits was (and still is) the act of making changes to a schedule: no longer does the user have to erase/white-out/cross-out a changed event and re-write it somewhere else.  By using computer-based calendars, all the user needs to do is drag the re-scheduled event to its new location in the calendar.  Yet these early solutions offered little (if anything) in terms of sharing your schedule with co-workers, family, or friends.  Read on to find out how digital calendaring can help us and what changes need to happen in order for it to improve.

The good

Then along came the web and helped the matter out (to a certain extent).  Online calendaring applications like Yahoo! Calendar made calendar-sharing easy and thus – popular.  Yahoo! Calendar even has a “sync component” that would synchronize the desktop calendar with the web version of Yahoo! Calendar.  And with the development and proliferation of new web technologies (namely AJAX), Apple, Microsoft, Google, 30Boxes, Plaxo, CalendarHub, HipCal, as well as many others, were able to make some of the easiest and most functional web-based calendars.  And to this date, Google Calendar (GCal) still offers one of the best user experiences a calendaring application can have – an ease-of-use that beats most, if not all, desktop-class calendaring software.  Features such as “click-to-add an event,” context-sensitive event-adding robots, and sharing calendars with others, are extremely intuitive and useful and end up saving users a bunch of time when adding new events.  If that isn’t enough, GCal also looks pretty going it.

Now the bad

However, as we come to a point of maturity with these web-based calendaring services, their current limitations become very apparent:

1. Outside-of-network sharing
   Some of the aforementioned calendaring applications handle the sharing of calendars very well.  In fact, one of the biggest benefits of having a calendar that lives online is the ability to share it – with friends, family, and with the rest of the world (if you so desire).  The same goes for subscribing to calendars: have access to your wife’s schedule, your kids’ hockey practices and games, and even your favorite hockey team’s game schedule – all with just a few clicks.  And while that’s really awesome, sharing is a feature that still needs to be perfected.  What’s the biggest issue that needs work?  Compatibility and interoperability.
   While all of the aforementioned calendaring solutions all allow me to publish my calendar for others to see and subscribe to – even if they use a different calendaring service, they don’t yet allow “out-of-network editing.”  Sorry to get all cell-phone-lingo on you, but it’s the reality: if I use GCal and my friend uses Microsoft Live Calendar, we can share our schedules but can not make changes to them – I can see my friend’s calendar but can’t edit it by schedule an appointment for him (and vice-versa), for example.  This is a feature that is available only to “in-network” clients – meaning that as long as I stay and share within Google (or within Microsoft Live, for that matter), I can permit others to edit my schedule.  But if I go out of the network, I can’t.
   Verdict: this is a feature request that – while might not be at the top of every calendaring service’s feature request list – should become reality over time.
2. Offline access (and then some…)
   We know that one of the limitations of web applications is the ability (or rather lack there-of) to use it in offline mode.  It’s a major limitation that prevents frequent-flyers and travelers from relying entirely on web-based software.  Today, we have come to a point of partially solving these issues.  Technologies like Google Gears, Adobe AIR, and other synchronization services help to bring data down to the PC for offline use.  This is best evidenced by looking at Google, which today has two major offline-mode initiatives for its suite of web apps.
   • Google Gears – a browser plug-in
   • The second initiative is application-specific sync: the company just announced a way to perform two-way synchronization between GCal and Apple iCal, and has had a tool to do the same with GCal and Microsoft Outlook (although the latter has some limitations in its current incarnation).

   As we move closer and closer to solve the “offline access” limitations of web-applications, another need has suddenly sprung up that revolves around a similar axis: mobile-device access.
   I have been an iPhone user ever since the 4GB first-generation version.  Today I am the proud owner of an iPhone 3G.  And while I love my iPhone and would not even think about using another cell phone (except, perhaps one of the Android phones), one aspect of the device has me down.  What is it?  Calendar integration.  In this next section I describe the many problems an iPhone user such as myself needs to go through in order to have a 21st century experience with the calendaring system on the Apple iPhone.  I will be using the iPhone as the sole example because, in my experience, it is the platform of choice for developers and of companies alike; moreover, it’s calendaring interface is the best in the mobile arena.  Just so you know, I’m not trying to pick on you if you don’t own an iPhone… I’m simply using the platform as an example of what progress needs to be made in the mobile calendaring arena for the most usable mobile device.

Calendaring on iPhone

My biggest point of dissatisfaction with the iPhone is that there is no such thing as a “natural method” of bringing my calendar down to my phone and keeping it in sync wirelessly.  This is the case whether I use Google, Yahoo!, or Microsoft for my calendaring.  There is no way for me to go into the settings portion of the iPhone and configure my Google account to sync my Google Calendar with the iPhone’s Calendar app OTA (over the air).  So what’s the big deal with the whole “sync thing?”  Well, the whole point of web apps is to have access to your “stuff” wherever you are.  And this is even more true and important with a calendar – to be productive and to “work”, it needs to follow me everywhere I go.  Yet as of this writing, the only methods to get a synchronized calendar onto the iPhone are these:

1. Use a tethered sync through iTunes and sync to OS X iCal or to Outlook on Windows
2. Use Exchange through an employer/company
3. Sync over-the-air using an Exchange hack such as NuevaSync
4. Access your calendar in a mobile web interface through Safari

The thing is, all of the above solutions suck.  If that’s an overstatement, then to put it more nicely, all the above solutions compromise on something.  Below, I will go down the above list in the same order the above syncing methods are listed and explain what compromises are made with each new way.

1. Using a tethered sync with a cable is like using Windows 3.1 in 2008: while it might “work,” it’s very inelegant.  The user needs to constantly plug the phone into the computer to keep the two in sync.  If the user is a busy professional who makes frequent calendaring appointments and makes changes to them on the iPhone and on the desktop software, then to keep the schedule up to date requires constant plugging the two together (with a cord, I must add).  This is what over-the-air (OTA) syncing was made for.
2. Unfortunately, the only OTA sync the iPhone supports is Microsoft Exchange, a corporate-class suite for calendars, address book, and email.  The problem is, unless the user works for a company that uses Exchange, he’s out of luck.  And even if the user does have access to Exchange, then it becomes an issue of ethics and privacy in having the personal schedule on the corporate network.  So for personal use, Exchange for personal use would  be overkill: kind of like playing GTA 1 with today’s latest video card.
3. Fortunately, a few companies have popped up to take advantage of the Exchange capabilities in the iPhone.  I use NuevaSync, which takes my Google Calendar, pulls it down to its servers, and then converts it to Exchange.  This final Exchange format is what my iPhone reads.  I can make changes on the iPhone’s native calendaring app and changes will be reflected on my Google Calendar online.  While this solution works, it has limitations such as treating multiple Google Calendars as a single calendar: if I have different calendars, one for the ‘Nest Report and another for working out, my iPhone shows them as being one – the default calendar.  Also, it is a very ineligant solution that duplicates my calendar to NuevaSync servers.  All privacy concerns aside, this is simply an unnecessary step.
4. Online access to a calendar has the same limits as it does on the desktop: lose the internet connection, lose your calendar. wait until the internet is back.  Lose your service?  Same thing.  And most importantly, the Google Calendar “iPhone-special edition” interface is horrible.  Besides needing to log in every other time the calendar is accessed, the calendar (for some reason) doesn’t show “Today.”  Rather, it’s always a few days (or sometimes even weeks) behind schedule, requiring the user to navigate to the correct date.  Then there is the missing ability to make any changes to existing appointments: actions such as changing appointment time, date, or even deleting an appointment are missing from Google’s mobile version of the GCal interface.  And GCal mobile is by far the best on the market when compared with Microsoft and Yahoo!.

In other words – let me confirm that the above solutions suck.  They work.  But they suck.  So does using Windows 3.1 on a monochrome display… in 2008.

Fixing mobile calendaring

So what needs to be done to fix mobile calendaring?  What’s the solution?  Simply, make synchronization on the iPhone work.  This functionality can be added to the iPhone in a top-down method or through a “pull approach” by calendar providers:

• Using the top-down approach, Apple could work closely with calendar providers to integrate the calendaring systems and sync capabilities of these companies’ products into the device.  This would require Apple to come to calendaring companies and/or research their APIs, which is unlikely at the current time, as Apple is preocupied figuring out a uniform strategy for accepting and blocking entrants into the App Store.  So a better, more effective method for calendars to get to the phone by pulling demand through the channel.
• The “pull approach” is for Yahoo!, Google, Microsoft Hotmail/Live, Zimbra, and all the other calendar providers to come to Apple and show interest in getting their calendars OTA sync to the iPhone – all in a very easy manner.  Collaborating with Apple, these companies will make their calendaring apps to sync to the iPhone seamlessly.

The goal is to be able to hit the Settings icon on the iPhone, select Calendars, and proceed to pick which calendaring provider the phone should synchronize with.  Period.  This method has the ability to bring new calendar users to the calendaring companies – as iPhone users will see the option and want to check it out further.

The good – again

The good news, so far, is that the industry has standards in place to take care of all the problems I have so far written about.  The iCalendar format (iCal, for short – RFC 2445) is a standard for calendaring data exchange.  A word of caution – don’t confuse this with Apple’s iCal calendaring software; Apple’s iCal is an implementation of the iCal standard, not the actual standard itself.  The cool thing about iCal is that it is made to work without being dependent on a certain communications protocol/medium.  This means that to use it, one can use email, WebDav server, and SyncML, to name just a few.

Plan of action

With that said, let’s all stand up and request demand that web-based calendaring providers (such as Google and Microsoft) work with mobile device makers (such as Apple, Nokia, RIM, Microsoft, Google) to make built-in calendar set-ups, access and OTA synchronization a must on devices like the iPhone, like the BlackBerry, and like the Android-based phones.

PS and Notes of interest

After reading this article, you might be wondering about a few things.  If questions such as why I didn’t write specifically about the BlackBerry or the Android platform the way I did about the iPhone, why I so heavily concentrated on Google, and other calendaring “wonderings,” here are your answers:

1. Yes, I know that BlackBerry users have enjoyed for some time the ability to sync with Google Calendar.  I used the iPhone in this article for the simple reason that it’s the best – so far – mobile calendaring experience.  By far.  It’s all in the user interface.  Also, I use the iPhone myself and am therefore most familiar with it.
2. The same goes for the Android G1: the calendar on the G1 that integrates – seamlessly, I might add – with Google Calendar seems to be meant as a read-only calendar with a quick capability to “jot this down.”  I hope this gets better on this excellent platform.
3. As an aside, none of the mobile calendar clients – for any calendaring solution and/or device out there – have the ability to add guests to meetings.  This is most likely not going to affect the majority of users, however.
4. What calendar do I use?  Google Calendar.  I love the interface, love the ability to synchronize it to all my “desktop-class” machines – whether they run OS X or Windows, and rely heavility on sharing my calendar with the family (and giving them the permission to make changes to my schedule).  I am planning on using the GCal feature to integrate my calendar into my website.  It’s really cool!  I know that other (smaller) calendaring services out there might have better interfaces and more features, but somehow I love the interface that Google made.  On the other hand, Yahoo! Calendar is just plain old at this point and requires too many clicks to get things done.  Windows Live Calendar is a very early beta at this point in time and isn’t integrated with Hotmail.  Moreover, its synchrnization and sharing capabilities are very limited right now.
5. I didn’t mention MobileMe in this article for a very specific reason: it does not have the feature to share calendars with others and to allow them to make changes to my calendar.  Otherwise, it’s a perfect solution and will get my subscription dollars every year if the good people at Apple were to add this functionality.  Why is it perfect besides for missing that feature?  It’s a great interface online, it synchronizes with my Mac and with my Windows machines, as well as with my iPhone.  What else can a man ask for?
6. How about tasks?  Don’t you think tasks are part of a calendar?  Sure I do, but I use Jott.  It has an excellent online interface, an awesome voice-enabled iPhone app, as well as Adobe AIR-based desktop clients.  So tasks and lists are Jotted for me.
7. Lastly, I would like to address the practice of calendar sharing and the real-world need thereof.  Some would ask why calendar sharing exists in the first place.  Others would ask why  some would use calendar sharing to grant others privileges of making changes to their calendar(s).  If you fall into the camp of asking either one of these questions, then you haven’t realized the true power of web-based calendaring.  Sharing my calendar with friends and family is a must for me.  I need to let them know when to schedule certain things for everybody – and by giving them access to my calendar, I grant them piece of mind to sit down behind my schedule on their terms and plan.  So I grant my fiance full read and write priviliges to my calendar.  This is so useful when she needs me to do something and schedules it for me into a blank slot.  It’s also handy when planning vacations, trips, and night-outs: if she blocks off my time now, I won’t be able to defer or skimp out on it later, thus committing me to attend the event in question.  In this use-case, it’s more of a productivity tool that others help you use (in my case it’s my friends and family).  If you’re still doubting online calendar sharing, go and subscribe to a calendar feed of your favorite sports team or band.  Then tell me that it’s useless and not needed.  – exhales deeply -
8. In the end, we need computer-based calendaring to progress and evolve by:

• Opening up sharing of calendars across web-based calendaring providers
• Providing an easy way to synchronize the calendar to mobile device (such as mobile phones, PDAs)
• Making the calendars available offline – for viewing and editing

These days, it seems like Microsoft’s business is getting attacked from every angle.  What’s most interesting, however, is that the software giant is being challenged the most in those areas that it holds a significant share of the market.  From the Mac going after Windows on the desktop, iPhone gunning for (and surpassing by years end?) Windows Mobile devices, Linux infiltrating the server market, and OpenOffice along with Google docs chipping away at the all-mighty Microsoft Office – the big M has many companies to pay attention to these days.  As of late, Microsoft has been so busy saying goodbye to Bill Gates chasing its competition, it forgot to show up to a scheduled fight with one of its most feared closest rivals.

“Exchange for the rest of us”:

Let’s see what Microsoft’s identifiable markets are: home users, business users, corporate customers.  In an interview on Windows Weekly a few months ago, a Microsoft executive in the online Live division explained how the company sees corporate users also as home users who want to enjoy their computers and have fun with them when not at work (my paraphrase).  He noted that it was Microsoft’s goal with Live to unify the experiences of such users.  That’s great and all, but just tell me one thing: how does a tech company that has been (incorrectly) relegated by the media to be the best choice for “home users” beat you in making “Exchange for the rest of us”, when Exchange is your own (Microsoft’s) product?  It’s so embarrassing that it overshadows Windows Me (the biggest flop to leave Microsoft labs).

Just in case you have been living under a rock for the last few months, that company with the “home user” target market goes by the name of Apple, Inc.  You know, the company who is known for turning certain industries upside down and re-inventing the business processes within them.  Apple announced MobileMe on June 9, 2008 and dubbed it “Exchange for the rest of us”.  That “exchange” reference, as mentioned earlier, is alluding to Microsoft Exchange – a corporate/large-business email and PIM tool/service.  MobileMe basically does Exchange but for the consumer – on a personal subscription level.  Herein lies the question: how does Apple, a company so focused on the “home user”, roll out something Microsoft should have been selling for the last five years?

You see, somewhere along the lines of Xbox breakdowns, Vista problems/negative PR, and chasing after copying Apple with Zune, Microsoft completely missed the boat.  For a nominal fee to the user, Microsoft should have created “Exchange Hotmail”: a paid-for part of Hotmail that “brings your data with you at the speed of *push*” (my marketing tagline).  It should have been the scaled down, personal version of Exchange that integrated with Hotmail/Live mail in the cloud, integrated with an Exchange-compatible mobile client, and pushed out to Outlook/Windows Live Mail on the desktop.  It would do push email, calendar, and contacts the way Exchange does it, only Joe User would be able to sign up for it himself.  But it wasn’t to be.  Apple brought it first because Microsoft was too busy defending its “server plays”.  Most likely, the big M felt that introducing a personal version of Exchange tied to Hotmail would in some way enroach on its own user base of corporate Exchange users.  But that’s just a load of bollocks, since the two markets using Exchange enterprise and my proposed Exchange Hotmail would be different (a corporation would still run an Exchange server for company-wide email and Joe the employee would simply subscribe to Exchange Hotmail for personal use).

On second thought, the company did roll out a scaled down version of its server product for home users dubbed Windows Home server.  Why could it not have applied the same type of thinking to an email and PIM system?  After all, the new Microsoft is all about software plus services (as described in the linked memo by new Microsoft chief Ray Ozzie).  Exchange Hotmail would have been a perfect play for Microsoft.  So in the end, Microsoft is left with a very popular online mail solution (Hotmail) yet has not made a significant effort to monetize it.  Apple, on the other hand, has beaten Microsoft at their own game and has brought out a kick-butt web service and, along the process, used Microsoft’s “Exchange” moniker in its description – almost as a mokery.

On triple thought, what has Microsoft really done to Hotmail and its consumer online services lately?  Sure, they have copied Yahoo! and made Hotmail “drag-and-drop”.  But what Apple is really great at doing is making an end-to-end solution, as the comapny has done with iPhone and MobileMe.  The latter is the perfect complement for the iPhone user.  Microsoft hasn’t seen the light at the end of this tunnel, and the jury is still out to see if it ever will.

P.S. Throughout the article, I put “home user” in quotation marks because for years it has been thought that “home use” was the best use of Apple Macs.  Though this opinion is beginning to change rather quickly – and as it should – many uninformed tech journalists, “experts”, and those in tech media still wrongly believe this to be the case.