Apple iPhone 3GS Review: Bad for Business?

If you’re considering buying the Apple iPhone 3GS or any iPod or related product – especially for business purposes – you’ll definitely want to read this essential article. I was one of the fortunate people to receive a brand new 32GB iPhone 3GS at a discount price. It arrived within a week from placing my order via overnight mail from AT&T. I was excited at the proposition of perusing the 60,000+ state of the art iPhone applications! After getting beyond the glamorous surface and still enjoying a great user experience, I’ve found several surprises that might affect your understanding of the iPhone.

The iPhone 3GS is a true, graceful experience of combining minimalism and modernity with marketing and packaging that is second to none. It was exciting to unwrap and unbox the new gadget that promised so much fun and functionality. It does deliver, no doubt. As a music and video player, it’s still the clear leader both in form, function and audio/video quality. But how useful and practical is it for business? I’ve heard it said many times that it’s more an entertainment device and, to a large extent, this is still true.  This article will explain my experience with the iPhone and also provide information on how it differs from the functionality found in most other phones. Depending upon how you work, this might not all be a completely positive and streamlined experience, especially if you don’t own a Mac.

One Click Purchases Only at iTunes

You must impulse buy everything @ iTunes!

I installed Apple’s synchronization software – iTunes – and was disturbed to discover that the mere act of registering the iPhone with Apple required me to provide Apple my personal information and credit card number. Apparently this might be the case because Apple wants to set up an account for you at the iTunes store, the only place you can buy applications approved for the iPhone. Interestingly enough, I also found that I couldn’t set up a “shopping cart” and could only use “one click purchasing” – the power of impulse purchases where you don’t see just how much all those applications really cost in total. I was beginning to sense a trend focusing on control and revenue from value added services, which is apparently a relatively common perception of Apple’s focus these days.

I downloaded several applications and found them extremely useful. Facebook’s iPhone application is marvelous. A Google Analytics application allows me to see, at a glance, all of my web site metrics including what happens at Safari is a quick, useful and delightful web browser to use. The music and media portion were quick, easy to operate and the screen is beautiful. It’s obvious why the iPod is so popular. Google Maps is splendid being sprawled across a large screen. RSS, podcasting, glorious handling of rich media. One handed operation with the iPhone is generally not possible but there are advantages to its OS that are time saving over a Blackberry. If you type numerous emails, this phone is probably not going to work for you. While you will not get the same, satisfying tactile feedback from a physical keyboard, I was surprised that the iPhone’s screen-based keyboard with error correction seemed to be better than I had imagined. If you don’t regularly type long emails, the iPhone keyboard is extremely serviceable for email with practice and if you have small to medium sized thumbs. It has specialized functions to aid with typing (excellent word correction) as well as cursor placement (hold to zoom in on the screen to place a cursor.) My only gripe is that typing commas or periods takes too many keystrokes and the only way to get a a different keyboard layout is to hack (or “jailbreak”) your iPhone. Instructions on usage are sparse and you will best served downloading the manual for the iPhone from the Apple web site and giving it a quick read.

Unavailable unless you jailbreak the iPhone. Apple

Jailbreak! If Apple doesn't think you need it, you're not getting it from third parties.

But shortly thereafter, I began to discover the frustration that other iPhone users conveyed to me but could not properly articulate. Apple’s need for total control over the iPhone can, at times, greatly undermine its utility. Unless Apple provides all useful and necessary system extensions, you’re simply not going to see them in the iPhone. At times it will feel as if the iPhone is a work in progress with some glaring omissions – after all, it took Apple years and three versions of its iPhone operating system just to implement basic copy and paste functionality.

For example, the iPhone is noticeably missing an easy access “today screen.” Important to any business professional is the ability to see the daily agenda, current tasks and phone notifications quickly. On the iPhone, this is not possible except if the phone has been hacked. Apple is so vigilant about preventing third party developers from creating such necessary additions that it even went so far as to file a patent two years ago for the creation of a long overdue and extremely common functionality. A today screen won’t happen unless Apple provides it. Looking for battery saving utilities that can control common settings for your phone in one contenient place? They just don’t exist as Apple has not provided necessary tools to developers to improve what they believe works well enough on its own. It’s either Apple’s way or the highway! Other odd ommissions the inability to add/remove custom text messages sounds and other alerts (which apparently use a different file type and location) and the need to use command line programs such as “ssh” to log into the phone and make changes. Chances are that virtually all the software tools to customize your iPhone are not provided by Apple but by third parties, which is in direct contrast to what most would expect and where Nokia excels with its Symbian phone customization software.

With regard to reception – at times my AT&T GSM iPhone received better signal than my Verizon Wireless Blackberry 8330 – even in the New York City Subway (take 34th Street and Herald Square as a good example.) The phone reception isn’t perfect, cuts out in some areas not covered as well as Verizon (such as Roosevelt Island), but the audio quality when connected was at least as good as other phones. I did find the audio quality of the flat ear speaker to be somewhat tinny and difficult to hear in noisier areas, but not enough to be a dealbreaker. I use a headest which minimizes this issue. The audio and video player is second to none, both in terms of functionality and audio fidelity. Perhaps I could get over my fair first impression and use the iPhone for business after all – there is tremendous utility that benefits from the iPhone’s operating system.

Spam Email

No spam filtering. Smut everywhere.

Email POP or IMAP setup on the iPhone is quick, simple to use and well crafted. It visually provides a very good user interface and experience. My joy was short lived when I began to realize that I couldn’t easily have emails automatically set to justify to the width of the screen. My Blackberry was able to format these emails automatically so that text was legible at the right size. My choice on the iPhone was to either view in landscape mode or make the size of the screen bigger and scroll from side to side and down to read, which is rather laborious. There was no way to filter spam and none of the 60,000+ applications in the iTunes store provided much relief. Sadly, I read a post by a spam prevention developer that Apple simply doesn’t provide tools for developers to modify or extend the iPhone OS in certain areas. Common features such as “select all” to delete every item in a mailbox is not provided, nor the ability to dump email from all your accounts into one consolidated mailbox. It is not possible at present to download email attachments. Email is getting there but will take some time to add functionality that most of us who use email regularly have come to expect as standard on other devices.

If you run a business and manage any kind of photos, text files or other media files with regularity, the iPhone may provide a frustrating and disorganized experience. Apple believes that the phone should follow the principles of cloud computing and use wireless technologies to transfer all of your documents and files. Not surprisingly, some problems can be resolved using wireless services purchased from Apple such as “mobileme” which will add additional cost to your purchase. But more disturbing is that Apple didn’t leave any option to use the “old” method of simply using a cable to connect your device to a PC to drag and drop files or synchronize them.

Unlike any other PDA you’ve had for years, the iPhone has no “disk mode” – it isn’t made to act as a USB drive where you can plug it into your PC, drag and drop files onto the phone’s “hard drive” which makes the files available to all your phone’s applications. If you’re a doctor or lawyer who uses dictation, get used to having to manually turning on WiFi and connecting to a WiFi enabled computer just to transfer your files each day. But even with WiFi there is no drag and drop process. There is no file “explorer” type functionality to browse the phone’s vast 32GB storage area – each application can only see files which have been transferred to the phone using that application’s specific transfer utility. The uploaded files are stored in that application’s private folder, so you can expect documents and files to be scattered amongst different applications on your phone and not in one convenient place. If you only require document viewing, there are applications that allow you to use your iPhone as a USB drive and drag and drop files onto the mounted iPhone. But this method does not allow any of the files, for example a photo, to be accessible for editing in your favorite photo editor – remember that the application you want to use must be the application that transferred the file to your device via WiFi or other wireless method. I think this is awkward at best.

iTunes synchronization still does not handle – to my great surprise – any documents such as text, Word, Excel and PDF files. iTunes only handles “tunes” such as audio and video files.  I find this extremely frustrating and time consuming. As my iPhone stays in its USB dock most of the time, connecting it to WiFi is, to me, a needless hassle. If you have 3 different applications to read or manipulate files, you must connect via WiFi (by finding the phone’s IP address or pairing the device) and then using each individual application to transfer respective files and to sync them. If you’re on the road and don’t have access to WiFi or to the wireless network, you simply won’t be able to get a file into your iPhone to view or edit using your application of choice. And as per the above, even if a document is on the phone, you can’t move it from location to location – the only solution I could find is to use application A to download the device onto a hard disk and then use application B to upload that file back onto the iPhone. Again, this makes file management an incredible chore and unique only to the iPhone.

No, that's not file navigation.

No, that's not file navigation.

Let’s try a real world example – Documents to Go, the standard for Microsoft Office viewing and editing on many mobile platforms. How do you get files onto the iPhone for viewing and editing in Docs to Go? If you receive a Word document via email, there is no capability to download the attachment onto your iPhone at all. Even sending to a Hotmail or web-based email account is no solution, since the iPhone browser (Safari) will not allow you to download the document. You cannot simply drag and drop your Word document onto the phone if it’s plugged into the USB port. And, remember, there is no document synchronization option using a wired connection either. So… how do you get that file into the iPhone? (i) You must have a WiFi connection. (ii) You must obtain a random number on the Docs to Go iPhone application to enter into the Docs to Go desktop software to “pair” the device (even more complicated with QuickOffice which requires you to obtain the phone’s IP address). (iii) You can now transfer files using the Docs to Go synchronization software. In contrast to how this has been done on other mobile platforms with “one button” or automatic synchronization of all yor files, you can see how much of a hassle this can be if you intend to use Docs to Go.

Outlook sync works quite well but don’t expect synchronizing your calendar to be easy if you’re a power user. I discovered rather quickly that the built in calendar system has limitations and doesn’t provide several common features such as default alarm time, e.g. setting your alarm to ring one hour before every appointment unless manually entered by the user. There are some PIM replacements but far from their counterparts appearing on other mobile operating systems. Many PIM applications follow Apple’s “cloud computing and always wireless” focus, choosing to sync with Google calendar rather than Outlook (such as the popular Pocket Informant.) Task management is not offered out of the box, none of the good choices are Outlook compatible and virtually none have desktop clients for the PC to view and enter your tasks. You’ll probably need to view calendar in one desktop/web-based application and tasks in another. Synchronizing your iPhone with two desktop computers requires going to users who have hacked files to “trick” iTunes into permitting this function. That’s not acceptable, especially since most business professionals will have at least a desktop home/office PC and a traveling netbook or laptop.

So what can you expect from the iPhones 60,000+ applications? Some of them are very good and extremely easy to use. This is a tremendous asset the iPhone has over many other platforms. The overwhelming majority of iPhone applications are games, useful tools for purposes other than managing the iPhone, and iPhone optimized versions of popular web sites – the iPhone is the new WAP. If you’re looking for efficiency navigating the most popular web sites, there is no subsitute for the iPhone.

iPhone apps are just the new WAP. Love the big ads too.

iPhone apps are the new WAP. Superb ease and user experience. Get used to the advertisements!

Numerous iPhone applications provide a completely new experience that is different from other “freeware” on other mobile platforms. They are designed to collect an email address from the user (usually for service based applications) and/or to provide what appears as flash-based advertising on the iPhone. There is a great potential for marketing and revenue collection on the iPhone which is one incentive for iPhone developers.

On the dark side, there are a dearth of external applications that enhance the existing limitations of the phone OS and business tools that work well with a PC. If a feature isn’t present in the phone, it could be a while until you’ll see it appear. It took years just for Apple to provide “copy and paste” functionality on the iPhone and we wonder how long it will be until there is spam filtering, power saving utilities, true file management and attachment downloading, all which are critical for business and available on every other platform but the iPhone. As echoed before, most good solutions are available only on the Mac, such as tasks management.

Battery life – unfortunately with the iPhone 3GS, there is a significant probability that your iPhone may not last through a single day without charging the device somewhere. Apple reduced the size of the battery in the iPhone 3GS by 15%,which is exacerbaged by the iPhone’s dependency on using energy challenging wireless connections and applications that always believe you are connected. My estimation is that 40 minutes of phone usage, 80 minutes of PDA usage, 30 minute email check and 40 minutes playing music will easily push your phone at or below the critical 35% mark, even with Apple’s “solution” for its middling 3GS battery life (recommending that purchasers reduce or remove all the features which compelled consumers to buy the iPhone.) An example of why the phone drains batteries so quickly is the software – if you do so much as open an email account to review your emails, the iPhone attempts to connect wireless. There is no way to turn this off. And like numerous other iPhone applications, even being in “airplane mode” with the radio off, applications will warn you incessantly that the radio is off and give you a convenient but annoying ability to open the control panel to turn it back on.

Unfortunately Apple also seals the iPhone so that there can be no user replaceable battery. If you’re questioning whether the battery life can be anemic, ask yourself why there are so many third party aftermarket solutions, which for the iPhone translates to purchasing an expensive power brick to carry with you on your journey. Battery saving utilities you’d find on Windows Mobile, Blackberry, Palm or Android devices are only available on the iPhone if you “jailbreak” the phone, meaning you have used a program to break Apple’s proprietary OS from preventing the use non-Apple approved applications (and which will void your warranty.) Even the “today” screen which is popular on virtually every handheld but the iPhone, is only available from a third party developer for phones that have been freed from Apple’s shackles.


Very useful application and the bottom advertisement is ubiquitous!

In the end, there are many positive aspects of the iPhone I didn’t cover including its fast processor, ease of use, excellent wireless implementation, etc. I merely covered the issues to let the buyer beware before purchasing the iPhone. For most who just want to view documents they have received in email (like the old Blackberry), the iPhone will work just fine. It has a superior user interface for many applications but it comes at the expense of being very limited in many instances with significant improvements potentially a long way off. If you like the ease of drag and drop – which I do – you’ll find getting document management a tedious, unrefined chore on the iPhone. This is double if you do a great deal of file transferring on the road and don’t have access to WiFi at work to connect to your PC.

Am I keeping my iPhone? The jury is out. On one hand, it’s a joy to have every day on my daily commute. It has so many applications that make surfing popular web sites a joy to use. On the other hand, the constant need to recharge the device and awkard document management that requires WiFi leaves me wondering whether I’ll still be happy when all those incredible mobile phones released in Europe and Asia finally hit the US. I’m not sure that the Palm Pre is ready for prime time but, if my sources are correct, if you can hold off for 3-6 months, you’ll start seeing new arrivals on the market like the powerful HTC Touch Pro2 that may be more satisfying for document usage and email management than the iPhone. The rumored “Storm 2” may also provide significant enhancements that might make the business tailored Blackberry the mobile device of choice for business. The iPhone is a great tool and whether it’s unique and proprietary system will work for you is your choice.

Michael M. Wechsler, Esq.

Internet / Mobile entrepreneur since 1989, Intellectual Property attorney since the mid 1990s, former in-house counsel at, Senior Vice President of Business Strategy at Zedge, Co-Founder of the IDT Internet Mobile Group, E-Discovery expert and legal consultant with Kroll Ontrack, and owner and operator of

Michael M. Wechsler, Esq. – who has written posts on The Law Professor.


  1. Jeli says

    You really don’t know how to use your iPhone do you?

    You recommend jailbreaking but dont know how to use the file manager apps out there or even better iFinder, etc.

    The first thing any jailbreaker should do is install the Safari addon pack and enable file downloading.

    Just sounds like you don’t like Apple and used this as an excuse to complain.

    Sounds like what you were looking for was a laptop. I hear Apple sells a few.

  2. Frank Scherer says

    That is the most useful review of the iPhone I have ever read. I have bookmarked it and will email to my friends who are undecided. I am no longer on the fence. Thank you.

  3. Michael M. Wechsler, Esq.thelawprofessor says

    Actually, I know my iPhone rather well. What you need to do is read a little more carefully. Most iPhone fans love their phones and think that jailbreaking is a right and option. It isn’t. It voids your warranty. If you want to do that, go right ahead but that will not be an option in an overwhelming number of businesses. I cannot imagine any company buying 500 iPhones so that they can void their warranty immediately. As I said, the iPhone only becomes a truly useful and efficient business tool if you jailbreak the device – but this isn’t an option for business users, perhaps only for individuals with a small business.

  4. Michael says

    For those who questioned just how poorly the iPhone is designed as a business tool, apparently it is Apple that has refused to allow USB sync and crippled the iPhone! Incredible! As stated in the article, you can’t just dock your iPhone and watch it all sync. For every application you must (a) turn on WiFi, (b) connect the iPhone to the desktop application for each application to enter “pairing mode”, and then (c) perform a sync. Insane and a colossal time waster. Here’s the proof directly from the DataViz site, which provides documents to go and the explanation of why the iPhone is the only phone you can’t sync documents to while docked.

    Question: Can I synchronize Documents To Go for iPhone through a USB cable?

    Answer: No, this is not possible because Apple does not make USB synchronization available to third party applications. In the current iPhone OS, a third party application cannot access files outside of its own location on the device. This location is known as the application’s “sandbox”. Unfortunately, application sandboxes are not visible on a desktop when the device is mounted via USB. The iPhone OS keeps the application sandbox area hidden and only accessible by the application on the device. For Documents To Go, this means that files must be transferred via WiFi since using a network connection is the only supported means of accessing our sandbox from a desktop.

    We understand that WiFi connections can be problematic for some users and we are currently researching alternatives.


    For those of you wondering, Documents to Go just recently crashed on my iPhone. All the documents I had in the Docs to Go sandbox were lost, unavailable to any other application on the phone. On Blackberry, Windows Mobile or Palm devices, your documents are stored in the general memory and accessible to any application on the device.