Microsoft Looks a Lot Like Apple in 1997 — Which Should Scare Apple

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In the mythos of Steve Jobs, there’re a couple of big moments. One of them is his taking the stage at the World Wide Developer’s Conference in 1997, a meet-up of Apple devs that usually veers toward the code-crunchy side of Apple, and simply taking questions for an hour. It was Jobs unfiltered, before the carefully controlled keynote presentations: sarcastic, angry, petty, but brilliant. Here’s a (very grainy, very 1997) YouTube clip from the event.

Skip to 2:30 to see Jobs take the stage, but the key moment comes around 4:30 in, when a developer asks about the status of OpenDoc, an ambitious and beloved way of standardizing a lot of moving parts within the Macintosh ecosystem.

Jobs, newly reinstated at the company, had, in his own words “put a bullet in the head” of it. His reasoning? “Apple suffered for several years from lousy engineering management,” he says. “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are.”

The whole speech is impressive in how much it lays out almost exactly what Jobs and Apple would do over the next ten years, leading up to releasing the iPhone, and, eventually, overtaking Microsoft as the most valuable tech company in the world. The Mac OS would become simplified, leading up to OS X. Bright colors (and later aluminium unibodies) would make computers not just tools but objects to admire on their own. And Apple would take great pains to cement what it meant to be an Apple user.

The Mac had always been popular with professionals who worked in graphic design, thanks to its being the first to bring together a graphical user interface in a way that made intuitive sense, and Apple’s working with companies to develop software for creative professionals: the whole Adobe suite of products from Photoshop to InDesign, or video-editing software like Final Cut Pro. But in the ten years following Jobs’s return as CEO, Apple would cement itself as the laptop of choice for people who made their living in creative fields, period. For anyone you could fuzzily describe as belonging to the (ugh) “creative class,” the Mac was king — even for people like, well, me: writers who really only needed a working web browser and a some sort of word-processing program. Macs were for laying out visions and taking what’s inside your head and substantiating it in the real world; Windows machines were for filling out spreadsheets, and also, uh, filling out spreadsheets. Apple was an underdog company built for the artist, Microsoft a beige behemoth built for the cubicle, crushing any competition it could find.

Apple went after this creative-class market share for two reasons: One, creative professionals, for better or worse, are more influential in culture and society than, say, CPAs. Two, creative professionals are also a highly lucrative market, willing to pay the higher margins Apple puts on its relatively underpowered machines for a more aesthetically pleasing product, both inside and out.

It did this through marketing — Apple remains obsessed with image and perception. Its “1984” ad is iconic. Fighting to regain market share from Windows, its “Switch” ads in the the early ’00s were amusingly effective. But there were no ads that so directly drew a comparison between the Mac user and the Windows user than the “Get a Mac” ads that ran from 2006 to 2009. You know the ones. Justin Long, looking like he’s about to head out to a Wolf Parade show, rattles off the capabilities of being a Mac. John Hodgman, besuited and politely prim, is the eternally beleaguered PC.

Watching them now, the ads have aged incredibly poorly. Perhaps it’s just because I’m older, but Long is a little too smarmy Road Runner to Hodgman’s Wile E. Coyote.

But it’s not just the slightly out-of-date fashion or the smugness that makes the ads seem weird. It’s the last two days, which saw first Microsoft and then Apple roll out their new lineups of personal computers. I found Microsoft’s Surface Studio intriguing as hell — bold and different and unlike any other desktop PC out there. I found the MacBook Pro with Touch Bar to be a more powerful and lighter version of the same thing I’m typing on right now, except now there’s a slightly goofy strip of touch screen added to the top row, where I could theoretically type out some emoji or something.

More to the point, Microsoft and its Surface brand of computers are aggressively targeting creative professionals by offering them something new and different: the ability to interact with their entire screen the same way they would a piece of paper. They’re willing to make new devices like the Surface Dial and see whether customers respond. The first Surface computer was a disaster — a fuck-up that cost Microsoft nearly $900 million. (The Lisa, Apple’s first computer with a graphical user interface, was a similar failure.) They kept at it, and now the Surface line represents the leading edge of what computers can look like and do. And Microsoft now wants those premium customers, those graphic designers and video editors and illustrators, to come along with them. Much like Apple in 1997, it’s entirely possible this effort will fail. (Unlike Apple in 1997, this would not destroy the company.) But Microsoft, using that total control of hardware and software that Apple proved could be so potent, is taking chances.

Apple now sits on over a half trillion dollars in market capitalization. The iPhone is the undisputed king of phones, the iPad still at the top of the heap when it comes to tablets, and a walk through any office or coffee shop will show you that Apple still firmly controls that demographic of professionals who might say “Daydreaming is actually part of my job, you know?” Apple as a company doesn’t even really need computers anymore — they make five times as much money from their phones as they do their computers. This may explain its odd complacency, so similar to Microsoft in the late ’90s, when its OS and software and web browser happily sat on top of the world, churning out money. It might explain why Apple would fail to update its desktop computer, vital to any actual creative professional who needs as much processing power as possible at the sacrifice of portability. Why, instead of offering a risky but innovative new way of interacting with their computers, they gave up a row of keys its head of product declared “didn’t matter” and replaced it with a thin strip of touch screen with dubious usability. (Watch the Apple keynote yesterday, and you’ll notice that even Apple’s own employees, demo-ing their own devices, seem to struggle with using the Touch Bar.) Apple’s laptop line seems adrift, without focus. It seems incapable of saying no to a hundred things and saying yes to one exciting thing. Apple still remains incredibly good at industrial design and manufacturing; its products at every level where they touch the consumer are still best-in-class. The Surface Pro 4 is a very interesting computer, but the MacBook Pro I’m typing on still just feels better in dozens of tiny ways.

But there’s a real sense of a company that’s coasting when it comes to computers. I have no doubt there is feverish action around next year’s iPhone, which will mark the tenth anniversary of one of the few pieces of consumer tech that you can legitimately say changed the world. I don’t get the same sense of urgency around a new iMac desktop, or figuring out how to keep someone who lives their life in Photoshop a satisfied customer. And the lesson of Microsoft in the 2000s should be instructive here: Complacency and taking the customer for granted can cost you.

In this light, those “Get a Mac” ads don’t just seem dated and self-satisfied. They make you wonder about who exactly these characters are. Hodgman, nerdy or not, seems to actually be doing things, doing a job. Long, smiling, in an unzipped hoodie, seems like a rich college kid who might claim to have made a short film, but when you took a look on his MacBook Pro you’d just find, well, nothing.