“It’s starting… :-)

Those were the only two words in an no subject email from my 18 year old son yesterday. That and a link to this story.

Hours later, “…the ultimate combo: Starbucks and iPhone!” from my 20 year old daughter.

At first I did not know which to be more impressed by, that Austin knew about CP 24 or that Cassidie might finally consider trading her Blackberry for an iPhone. But quickly, the real weight of this story grabbed hold.

I tend to seesaw between eras. Occasionally I romanticize the imagined simplicity of yesteryear, only to wish tomorrow’s technology was here today.

For those who know me, there isn’t a new technology I won’t try. Be it iPads, iPhones, or Taylor Made R11 Irons. If they announce, I line up. It’s how I am wired.

However, in the case of Starbucks announced iPhone App, it has less to do with my technological obsession and more to do with the disdain I have for a wallet that is, quite literally, a pain in my a _ _.

I have never liked cash. Bills but especially coin. I was an early adopter for paying for anything and everything, no matter how small the amount, using plastic. I have endured the stares and glares, and I long ago got over the feeling of guilt from eye-rollers who think nasty thoughts of the guy buying a stick of gum with a credit card.

For the record, $4.83 on a credit card is a faster transaction than the person who insists on counting out eight quarters, ten dimes, twenty nickels, and eighty-three pennies.

My penchant for plastic over cash has nothing to do with credit and little to do with reward, although I am appreciative for the Air Miles and Aeroplan points I have accumulated and redeemed over the years. Indeed, it has all to do with convenience. Mine, not yours, as selfish as that may sound.

Damn the cash-loving and tax-evading taxi drivers. Don’t know what mean? Flag down a cab, run up a $7 fare using a credit card as payment. Watch carefully as suddenly the transaction won’t process. I find plugging the terminal back in helps. Add $1.50 “processing fee” to the fare and there’s your tip.

For as long and as much as I have been a fan of plastic over cash, I have longed even more for the day “chip” on a phone would trump as the preferred method of payment. It couldn’t get here soon enough was my personal bias in credit-card research I did years ago for one of the big two.

I am the exact demographic Starbucks is targeting. The guy who might leave the house forgetting his wallet but not his phone.

I accept we still have a few years to go before all my credits cards, bank cards, drivers license, health card, Costco card, reward cards…etc. are on my phone. I for one look forward to ability of leaving my wallet at home, not simply forgetting it.

For now, I will reward Starbucks for being among the first even if that means learning the metro-sexual name for “large double-double.”

RIM still doesn’t get it. In a previous post I argued that most people work to live, not the other way around. Why would people want a Blackberry device that does not let them be who they are outside of 9-5, when they can have an Apple device that does both?

I get it, there are a bunch of CIOs out there who buy into the “corporate only” model upon which RIM’s philosophy is entrenched. All that RIM co-CEO’s Lazaridis and Balsillie are achieving at Devcon this week, is to confirm their heads are still in the sand on this important and self-defining point.

Fair enough, they are entitled to do so.

In the meantime RIM will continue to lose market share as its stock price plummets to $6, while Apple’s share of the market will continue to grow and its stock price soars to $532 before long.

The folks at Apple must be beaming. Just days before the release of iOS 5 and the iPhone 4S, the Blackberry maker suffered yet another near system-wide outage that has even the most die-hard and loyal Blackberry users pondering a leap to iPhone and all things Apple.

Full disclosure, I am a former longstanding and headstrong Blackberry/PC disciple who made the switch to everything and anything Apple just over two years ago.

My toolkit includes an iPhone 4, iPad 2, Macbook Air, Time Capsule, Apple TV, and AirPort Express to name but a few of my contributions to Apple’s soaring stock price. I was also one of those with questionable priorities who thought nothing of standing in sub-zero temperatures for an iPad 2 and who yesterday refreshed his iTunes “check now” icon countless times until iOS 5 became available at 1:03 pm. And yes, earlier this year I was among those who foresaw and was critical of RIM for not better managing their inevitable demise.

With my bias and disclosure fully stated, it should come as no surprise that my advice to those in the Blackberry community who are, post-the-outages and other corporate woes, feeling a little shellshocked and wondering what to do next; by all means switch … and quite possibly … as fast as you can.

However, as head-in-the-sand and kool-aid drinking as I might be for the Brand Steve Jobs left behind, the leap to iCloud requires a little more thought than it does to convince yourself that you “must have” that next “beautiful” piece of hardware.

The decision to upgrade from an iPhone 3GS to an iPhone 4 was a no brainer. Much in the same way as I upgraded my less than a year old Macbook Air to the iCore 7 model. And despite my threats that tomorrow I refuse to buy the non-iPhone 5, chances are you will be able to spot me just outside the Square One Apple store sometime after midnight tonight.

But my penchant (read as OCD) for just about anything Apple markets hit a wall yesterday after I acquired and then really started to think hard about all that iCloud truly entails. As for iOS 5, go for it. But iCloud? You may wish to proceed with caution and thank RIM for my hesitancy.

Don’t get me wrong, the allure of everything iCloud promises to deliver is just that, alluring. The thought of not having to sync all my devices via cable is a level of functionality I have long awaited for. But, and this is a BIG but, do I really want to put the things I treasure most (my pictures, my music, my videos…etc.) in a place over which I have no, or very little, control?

It’s one thing not to be able to BBM or email for a day or two, but what if an attack on the cloud is far more catastrophic than merely a temporary outage? What if, Gulp-gulp and God Forbid, by some natural or unnatural occurrence all my valuable and momentous keepsakes were lost, stolen, or otherwise disposed of?  Be it a malicious attack from the outside or inadvertant glitch on the inside, am I willing to take the risk?

This is old-school thinking on my part, I know. I get it that I am supposed to simply let go and trust a technology I stopped fully understanding years ago. Thirty years ago I used to service my own vehicles. In today’s version of computers on wheels I wouldn’t know where to begin, yet I still drive. Moreover, the corporate world has for years relied and even insisted upon central servers for housing and accessing data as opposed to the near unmanageable array of standalone personal computers, few of which are ever properly or frequently enough backed-up.

In my case, I run a small corporation with enough on-site and off-site back-up reliability to fully safeguard my business and my personal digital effects. Add to this, I am admittedly a control freak about my equipment and data. As a general rule I don’t allow others to touch or use my equipment. Odd as it may sound, I can live with and accept responsibility for a SNAFU of my own doing, but I am far less forgiving if I put that trust in someone or something else and it fails. If and when that happens, I am not a particularly pleasant person to deal with, and/or I blame myself for not taking appropriate control in the first place. But I digress…

The point remains that in the first 24 hours of playing with iCloud I have already encountered enough unknowns to make me leery of jumping in with both feet. There are definite glitches and a few ill-conceived features. For one, the inability to manually delete photos from photo-stream is the most flagrant example of a disadvantage that outweighs the purported advantage. I have, consequently, disabled photo-streaming for the time being. There are other examples. To date I have been unable to sync music or videos across devices and I have been unable to connect with some who I know are also registered with iMessage. The promised lock-screen camera functionality either does not work or is missing. The list goes on.

These are still early days in the iOS 5, iCloud, and iPhone 4S Genesis. I am sure the few issues I have outlined and the many I haven’t will be addressed and ironed out in the days and weeks to come. And while I am still a little baffled about the odd-timing and combination of iOS 5, iCloud, but no iPhone 5, the Apple product line is still far superior in my mind than anything else. Mark my words however, sales of the iPhone 4S will be a fraction of the iPhone 4.

For those wondering if they should migrate away from RIM Blackberry-Playbook to to Apple iPhone-iPad? Of course you should. But even from this die-hard Apple supporter, you may wish to ascend to the cloud with caution.

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