Back in April, when Apple announced iAd as one of it’s “tent poles” of iOS4, I was pretty ready to just hold for Windows Mobile 7 and see how that looked. I’d had some time to mess with my sisters Zune HD and between that experience, and some of the Win 7 demos I’d seen, I was thinking maybe it was time to make a switch.

Not so much.

Of all the ways Microsoft could have gone after the iPhone – the hardware, the ecosystem, any of it – they pick iAd? The new platform is going by the name Toast for now and the goal is, as stated above, to turn their phones into “an ad-serving machine.” Good lord.

Like Apple, Microsoft is trying to spin this as a feature:

“For consumers, what this means is basically seamless experiences, seamless social connectivity”

Uh, what? On what planet is advertising a seamless, social experience? Advertising by its nature is about disrupting the users experience. It’s about taking them out of whatever they’re doing and saying “hey! look over here!”

What really takes this platform over the top for me is that while iAd is limited to applications, Toast runs in the main OS, serving ads right to the home screen of your phone.

I’m a bit a stuck record on this, but since we’re all here I’ll say it again: display advertising is an artifact of the print and broadcast worlds. It ignores all the best aspects of the web in exchange for showcasing its most boring. Worse, its left huge sections of the digital content economy in shambles, resulting stupid pagination schemes, and user hostile page layouts all designed to squeeze in one more ad. It’s bizarre to me that here on the cusp what should be the next wave of connected systems two companies that should be leading the charge are playing last decades game. I was genuinely hoping Microsoft would come into the mobile space with Win 7 and give Apple something to think about. But if this is how they’re going to do it, what’s the point?

Here is how I responded:

I think the author is well intentioned, and in a lot of ways, dead on about the issues of advertising online. My issue is that I don’t think fixing advertising is going to be what ultimately helps brands online.

My view is that advertising isn’t just a tactical approach, it’s also a way of thinking. It has fundamental notions of how the marketplace works and how brands relate to their customers. Advertising is about punctuating one narrative stream with another, something that doesn’t exist online. There is no stream online. Agencies, I think, often underestimate the power of the hyperlink. It defines the way people conceptualize the web, and it’s non-linear.

The web has fundamentally changed this brand/customer relationship though, and presented brands with opportunity to not just talk about themselves, but to actually provide a real and meaningful experience rather than just the promise of an experience at some later time. If a brand wants to know what the future is, or an agency for that matter, it’s not contained in the mindset of advertising, rather it’s in the world of product and service design.

There is a reason restaurants don’t advertise their food IN THEIR OWN RESTAURANTS. So much better to give them a great meal with great service once they’re already there. The web is a brands restaurant, the people are there. Give them something to love.

The bad thing about a dictatorship is that once the leader looses it, the whole thing starts to come undone. And they always lose it. There’s always something, some person, some event, that starts to place seeds of doubt and in the end, that single point of vision becomes a tyrannical mess of paranoia and irrational behavior. It’s clear Jobs hates Google. Not in a competitive way, but in some deep, personal and increasingly irrational way. For a guy who seems to have never made much of a bad decision, this target fixation has seemed over the last months to begin to take him off his game.

iAd is, for me, the first real manifestation of this unraveling.

Thursday morning, I tried to get out of the house early so I could stop by Voodoo doughnuts on my way into the office. One of the advantages of having your own agency is that you can declare any day that Steve Jobs is on stage as a company holiday. I had made it known early in the week that we’d be taking the morning off and taking over the conference room to project various tech blogs, eat doughnuts, and talk about Apple magic as it happened. For most of the presentation, for 6 “tent poles”, thats exactly what we did. Then came tent pole 7, iAd.

Here is my fundamental problem with iAd: It’s make no sense from a brand strategy point of view. It’s irrational, and philosophically counter to nearly every previous decision Apple has made under Jobs. To be clear, it’s not crazy in the way that most people will ever notice, after all, most of us have spent the last 15 years being trained to expect display advertising as just a way of life. But advertising is fundamentally user hostile. That’s the core nature of it, it’s why it works. It makes you stop whatever you were doing and look at something else that you didnt choose to. While it probably seems histrionic to take something so seemingly small and blow it up to this size, I do believe this marks a fundamental change in motivation for Jobs and Apple.

What Id like to do is agree with people like John Gruber that Apples motivations are to preserve the overall user experience of the iPhone, and honestly up until iPhone 4, that has always been what I believed. But iAd negates that premise on fundamental level. This is the first time I can think of Apple has chosen to make money at the direct expense of it’s customers product experience. People can, and have, argued for a long time that those of us supporting Apple and its draconian control of it’s platforms we’re just begging for this to happen. But I think it’s critical to consider that until iAd, the goal was to create a specific notion of quality user experience. For many of people, it wasn’t the experience they wanted, but that it was customer focused is hard to deny.

Of course there are already ads in applications so it could be argued that iAd doesn’t really change much. Or, to Jobs’ point in the presentation, this is a chance to make those ads better. This line of reasoning doesn’t seem to hold water though either. For a company allegedly so focused on preservation of good user experience that they’re willing to through Adobe under a bus, why would they invest so heavily in making intrinsic to the iPhone experience a system that would invite what is arguably the worst aspect of user experience on the web into their device? I can’t think of a reason. But the real difference here is that with iAd, Apple has actual financial motivation to have the iPhone/App UX degraded. Previously, Apple could take no position on in App advertising, but now, with a 30% cut of each ad, the more ads that go out, the better Apple does.

One could argue that Apple introducing iAd is better for their customers in that it allows more developers more opportunity to create applications and make a living off them. And this is true. But if Apples motivation were bring more developers into the fold, why on the same day they announce iAd would they choose to proactively lock out Flash as a development platform. Gruber’s take on this, as it has been from the start, is the Flash is simply not capable of producing a user experience at a level Apple feels is on par with the overall device. Fair enough. But if UX is the central issue, it’s hard argue that in app advertising, ads Apple will not be vetting, produce any better UX than Flash. After all, iAd gives huge amounts of iPhone user experience control to ad agencies, people with no track record of being able to produce anything other than bad UX and no motivation, monetarily or otherwise, to do anything other than throw away work.

Rather than spending their time and resources to update the App Store, something thats been asked for from nearly day one, iAd seems to be an investment by Apple in a race to the bottom. Tying application developers’ livelihood to the same display ad system that has left huge parts of the content creation industry on the web in shambles. Why not instead invest in making structural updates to the actual purchasing process to help elevate the developers doing the best work, and then help them find a way to actually charge a living wage for their work? Why not take the same, revolutionary approach Apple always has and find a way to free developers from having to find ad real-estate in their applications so they can focus on continuing to make their, and Apple’s, products even better?

The only logical answer is clear: To beat Google.

But given that a company whose name has always been tied to changing the game, such an investment in playing someone else’s game leaves me wondering: does Apple have the cultural and organizational underpinnings to manage a system that is both open to outside development and the clear frontrunner in a category, while maintaining their history of a clear focus on user experience? If iAd is any indication, the answer is no.

With Mac, Apple has always been able to be the contrarian second place. Making huge profits while catering to a smaller, but vastly more loyal base of fans. The iPod on the other hand is clearly the industry leading platform, but it’s closed. Apple has always had top to bottom control of everything that goes it save for the music. iPhone is something different though. It’s neither the plucky niche product of Mac, nor the highly controlled iPod.

In Apple’s seemingly desperate effort to control this rapidly expanding system, the strains on the dictatorial system are becoming evident, and it’s not clear Apple has the systems in place to stay sane. In fact, it would seem this new found position has resulted in increased paranoia and a fixation on beating specific competitors in specific ways rather than making revolutionary advancements. That they would try to lump iAd in with other user focused features is either completely disingenuous, or evidence of increasing detachment from reality. For whatever reason, Jobs has decided his mission now is to beat Google first, beat Adobe second, everything else comes third, including Apple user experience.

This isn’t to say that Apple will stop making good products, they’ll likely continue to for a long while. But as a post-Jobs Apple moves nearer, the questions of what drives the company without him become more important. iAd is a strong signifier of the kind of brand confusion that I think is beginning to emerge, and without Jobs in place, the “do what it takes to make money” path is now just viable as the “make great products” one. We’ve all seen “money at any cost” Apple of the 90′s, and it wasn’t pretty.

The good news is this: if you do manage to punch the monkey, you’ll win an iPad.

Note that every aspect of each device that HP pulls out is a technical specification. It’s the size of the screen, graphics cards, ports and so on. No where does HP mention the experience of using the iPad as it compares to the Slate. There is nothing about ease of use or ease of installing applications. Most striking to me: no mention of the OS.

To be fair, HP doesn’t have total control over a lot of these aspects of the device as they’re the hardware manufacturer so it may only make sense to speak to what they can own. Additionally, this may be intentionally geared to the person who would be looking at the HP in the first place.

None of this is meant to be critical of HP, I just find it interesting to see what motivates a brand, and how those motivations manifest themselves in the final product.

digital = new kids;
print = old guys in suits.

But that aside, it got me thinking again a question I’ve had for years: why is it assumed that there is a direct line from print to digital any way? The relationship between print and digital is about as close as print and architecture.

My question is – why don’t people draw a line from industrial design to digital?

After all, these two disciplines have far more in common. The relationship between aesthetic design and engineering. The concept that the thing you’re creating will be used in a place and in a way that you can’t control. And finally, the concept that something can be iterated over time.

Looking at digital products as product design efforts would have, I believe, a profound, and profoundly positive impact on the way work gets done, especially in the marketing space. It would release agencies from the mental model of a system that no longer seems to produce meaningful work. New team dynamics would emerge, new types of clients relationships would form, notions of timelines would be recreated, and new (and I believe more important) concepts of success would necessarily rise up.

So any way – why is it people seem to pair up print and digital?

I know this video is a few weeks old, but I keep coming back to it. Partly because it’s just funny to watch, but mostly because it’s such a great example of advertising mentally in an experience world. What we have is the difference between wanting to tell people your brand is fun, and exciting, and all about them; and actually being those things.

You can’t really fake this anymore.