Short answer: it depends.

Perhaps this verdict not surprising, since each device has its pros and cons and the widespread adoption of each are evidenced by the significant market share captured by each vendor. What requires a bit more under-the-hood analysis, however, is an evaluation of how well the devices actually perform as business tools and communication devices, more than simply comparing aesthetic preferences or brand loyalty.

Using any tool or technology requires some learning curve to master, and since both devices are currently available in the U.S. only through AT&T, a network performance/availability and pricing plan discussion between the two is a non-issue. What matters most to a small business owner (and admitted technophile) is practicality, features, and performance.

My primary reason for upgrading to the BlackBerry Bold from Research in Motion (RIM) in the beginning of 2009 was to make use of reliable 3G-data tethering, a nearly indispensable tool for those of us who need Internet access with our laptops and do not wish to add a separate data plan or the ever-so-20th-century USB modem dongle. When Apple announced its 3.0 version of software, as well as some hardware enhancements in its latest iPhone 3GS device, I finally considered the device to be entering the realm of what I would consider usable as a proper business tool. Despite being a huge fan of Apple products and owner of multiple Mac computers and iPods, I have resisted the iPhone since its inception as it has paled in comparison to the functionality of BlackBerry devices as business tools. Now having finally jumped on the iPhone bandwagon a few weeks ago, I have identified strengths of each platform in both architecture as well as native and third-party applications.

Architectural advantages of the BlackBerry Bold

A smartphone is, first and foremost, a phone. As such, any comparison of features such as design, applications, and usability all yield priority to functioning as an voice communicator. Comparing devices side-by-side (again, using same network in the same location), the Bold has superior audio quality using the headset directly, and in particular, when using the speakerphone. RIM’s audio design team raised an already high bar for audio performance with the Curve to an even higher standard with the Bold.

With any phone these days, communication is now frequently expected to take on written forms, such as sending/receiving text messages (SMS), email, and instant messaging (IM). The Bold’s keyboard is extraordinarily comfortable and is the best thumb-typing experience I have enjoyed to date (including Palm devices and definitely the iPhone). While I am quite impressed with the iPhone’s error correcting mechanism, it simply cannot rival the kinesthetic feedback offered by physical keys, and it is particularly ineffective at error correction when dealing with proper nouns, numbers, and symbols. I found it ironic in Steve Jobs’s initial announcement of the original iPhone two when he voiced contempt for the “cheap, plastic keys” used in other phones as being a hindrance to elegance and usability. Would these be a similar hindrance as the “cheap, plastic keys” which comprise their complete line of desktop and laptop computers? After all, if touch-screen keyboards were truly more efficient for data entry, we would all be using full-sized touch keyboards by now.

Having a physical keyboard also provides a wide number of single-press shortcuts to applications as well as assignable press-and-hold speed dial functionality for contacts. This translates to potentially over 100 single-touch operations which can be launched from the home screen (compared to the iPhone’s 20 icons per page, including the bottom dock). Further, hotkey functionality is designed into many BlackBerry applications along with context-menu features (via the trackball click) and full-menu features (via the dedicated menu button sporting the BlackBerry logo). This allows for access to a wide range of actions within an application with a one-or-two thumbclick reach.

What’s also great about the BlackBerry is the spell checking while typing feature, where an unobtrusive underline for a potentially misspelled word is identified and may be corrected by a quick trackball-initiated click to select a proper spelling. On the topic of the trackball (a BlackBerry hallmark since the Pearl), this mechanism is extraordinarily efficient for edit text (cursor placement) and copying/pasting. As such, any task which involves typing is a far easier, more efficient, and more accurate task on the Bold than the iPhone. On top of the kinesthetic physical advantage, the Bold offers an impressive autotext feature which allows for the addition of custom abbreviations (ala software like TextExpander) to further expedite typing tasks for common words and phrases.

Other advantages of the BlackBerry is that its operating system (OS) is a multi-threaded architecture, meaning that more than one application may be executed concurrently. This is particularly helpful when launching a web page in the browser, snapping back to BlackBerry Messenger or the email client to fire a response or copy some information, then jumping back to the browser to find that the page rendering has continue to load fully in the background. The BlackBerry is also highly configurable to a great level of detail regarding user options and profiles, and 3G data tethering via USB or Bluetooth and multimedia messaging service (MMS) actually work with AT&T’s service. Further, BlackBerry devices include media cards and provide an extremely handy automount feature when connected to a computer to facilitate file transfer to/from the media cards or internal memory from a computer. In using my phone as a primary business line, I also find great use in having a swappable battery which I have on-hand to maintain a full charge on-the-go. Given the fantastic support for Google application synchronization, having “cloud sync” of calendars and contacts is easy (and free) even for us non-Exchange users.

Architectural advantages of the iPhone

The iPhone clearly shines in two areas: anything involving pure reading or passive viewing, and having a flexible software development kit (SDK) for application development. Having incorporated MobileMe cloud synchronization was a huge feature when introduced (one I was awaiting since the original iPhone release) and elevates the status of both the device and the MobileMe service as true business-class tools (giving credence to Apple’s clever tagline, “Exchange for the rest of us.”). Visual Voicemail is a nice feature as a phone, but is certainly not a game-changing attribute.

Superior BlackBerry applications

BlackBerry Messenger is a great application which stands apart from other instant messaging (IM) clients, though it is restricted only to BlackBerry users. Using email within its underlying proprietary protocol, it easily allows for group chats and eliminates the 140-character limits of short messaging service (SMS). Further, in the realm of messaging, the BlackBerry OS provides a very clean integration of all messaging applications from supporting applications including emails, SMS/texts, Facebook, Google Talk/AIM, BlackBerry Messenger, and the like. It cleanly does so by aggregating incoming messages or active chats (if configured accordingly) to appear in the main message window, along with a small icon for the corresponding application. Along this line, it would be great to see a Twitter client incorporate this same functionality with direct messages.

As for other native personal information management (PIM) applications, the BlackBerry is very strong with its built-in calendar (week view, built-in task reminders), tasks, and memo applications. With AT&T, the Telenav software is very well integrated, providing accurate routing and point-of-interest assistance via speaking, typing, or selecting “Drive To…” within a link from contact or calendar event.

Other third-party applications which are of great use on the BlackBerry (and have superior functionality than the corresponding iPhone versions, if they even exist) are

• Vlingo (including the ability to create a “note to self” as or memo/task)
• Salesforce.com
• BBNotePad for editing text files within internal memory or on a media card
• Bluetooth keyboard driver for Universal Freedom portable keyboard

Superior iPhone applications:

Hands down, Safari Mobile is the best smartphone browser on the market. Its user interface, speed, accuracy of rendering, and automatic synchronization of bookmarks via MobileMe, is fantastic. What is surprising is that after two years of development, however, it still lacks support for Flash animation, as well as a simple ‘find text in page’ function which is only a shortcut keystroke away (by typing the letter ‘f’) in the BlackBerry mobile browser.

Similar to web browsing, reading HTML email on the iPhone is a dream. A very practical and important business advantage over the BlackBerry email client is having direct access to all of my IMAP mailboxes, something which RIM will likely never implement on BlackBerry devices given their desire to sell BES/BIS servers.

Other third-party applications which are of great use on the iPhone (and have greater functionality than the corresponding iPhone versions, if they even exist) are

• iPod/media player functionality: While the BlackBerry has a media player and it is easy to transfer to/from a memory card, the iTunes integration for media synchronization is top-notch, as are the iPod and Photos applications on the iPhone.
• Application store: The availability, user interface, speed, and push notification of updates for installed applications provide for a far superior experience in this are on the iPhone.
• The fantastic Remember the Milk (RTM) task/project management application which synchronizes with its corresponding online service provides a much more flexible way to view, sort, and interact with tasks compared to the BlackBerry’s native Tasks application.
• 1Password
• Tweetdeck
• YouTube
• FlightTrack
• iRentMovie for Netflix account/queue management
• HP42s calculator (yes, I still have an affinity for geeky calculators even after leaving the engineering world by trade)

Strange iPhone omissions

Despite now being on OS version 3.x after finally supporting such basic mainline features as copy/paste, Bluetooth tethering, and MMS, I am still amazed that a number of similarly “basic” functions are still missing from the iPhone OS and its bundled applications. Most, if not all, of these functions are supported by competitive handsets, and a number of them have been available for years in non-smartphone devices (i.e. regular phones):

• No Bluetooth object exchange (OBEX) profile support (allowing transfer of objects/files such as contacts, photos, or other files to other devices with the same capability
• Calendar
  • No week view
  • Cannot change calendar assignments (colors) for an existing event
  • Cannot tap-dial phone number listed as location
• Contacts
  • Cannot assign a new contact to an existing group
  • Cannot create/edit contact groups
• Safari Mobile: cannot find text within a web page (within Safari mobile)
• Cannot assign ringtones by contact group
• Cannot automount phone memory as an external disk (even though iDisk is now available)
• Voice recording via Bluetooth headset

In summary, the iPhone is great pocket-sized, connected computer and media viewer providing a flexible platform for custom application development. The BlackBerry’s place as an industry leading workhorse amd high-quality personal communicator remains well justified, not only in providing the common-sense expected features of a business tool but in providing a fair amount of personal/entertainment features, as well. Since most of the omissions and deficiencies of each platform noted above are software-releated, it will be interesting to see if either Apple or RIM will take note to improve their already great devices and remain highly attractive in the increasingly competitive smartphone market.