Apple’s long history is rife with defining moments…and, therefore, with roads not traveled that might have led to radically different places. I call the twenty-five items in this story “unanswerable questions” because none of them have right answers: Nobody knows what would have happened if things had turned out differently. All you can do is speculate. Which is what I do, briefly, for all of the questions below. But mostly, I’m curious what you think. These questions may be unanswerable, but it’s still a blast to try and answer them anyhow, as I hope you’ll do in the comments…

Let’s start at the beginning, shall we? After the jump, that is…

1. What if Steve Jobs and Steve Wozniak had never met?

Today’s Apple may be a company dominated by a single mind, but at the start, there were two geniuses behind it. Steve Wozniak gave the Apple II sexy color graphics, slots for future expansion, and other impressive features;  Steve Jobs put it in a case that was anything but clunky, and marketed it like a master. The skills of the two founders were astoundingly complimentary, but they might never have partnered up at all if their mutual buddy Bill Fernandez hadn’t introduced them to each other in 1971.

Harry’s guess: It’s hard to imagine any scenario in which Steve Jobs never became a big deal doing something, or in which Steve Wozniak wasn’t a major figure of early personal computing history.  But if Apple had lacked either Jobs’s packaging and marketing gifts or Woz’s technical chops, it might not have made it into the 1980s, let along lived on into the next century.

2. What if Steve Jobs hadn’t visited Apple PARC?

In 1979, way before Apple released the Mac or the proto-Mac known as the Lisa, Steve Jobs talked his way into a guided tour of Xerox’s PARC, the fabled research facility that spawned graphical user interfaces, the laser printer, Ethernet, and other breakthroughs that just about everyone except Xerox went on to turn into successful products. Jobs and other Apple staffers visited PARC twice, and came away dazzled by its Alto user interface. And who wouldn’t be? In the days of command-line interfaces, its icons, menus, fancy fonts, and mouse-driven design were literally a preview of computing’s future. Apple cheerfully borrowed Xerox’s concepts for the pricey and unsuccessful Lisa, then reused them for the Macintosh, the first computer to bring a rich graphical interface to the masses.

Harry’s guess: The Jobs visit to PARC is the stuff of legend; it’s tempting to riff on the idea that if it hadn’t happened, we’d all be banging out DOS commands on our keyboards today. Or, alternatively, that Xerox would have released a Mac-like computer that changed the computing world forever. Um, no: GUIs were such a good idea that they would have dominated no matter what. And Steve Jobs was so persistent that he would have turned Xerox’s good ideas (as well as numerous ones not seen in Alto) into Apple products one way or another. As for Xerox, it did commercialize the Alto interface in its Star workstation. Used one lately?

3. What if Woz hadn’t crashed his plane?

Steve Wozniak’s brilliant engineering was just as important to Apple’s early success as Steve Jobs’ marketing wizardry. But in 1981, Woz totalled his Beechwood Bonanza, doing severe damage to his memory. He recovered from his bout of amnesia, and did some engineering work for Apple thereafter. But only a little work, and mostly on the Apple II, which was in the process of being eclipsed by the Mac. Otherwise, he filled out the 1980s by returning to school, becoming a teacher, bankrolling the US Festivals, and founding an unsuccessful universal remote control company called CL 9. He also continued on the Apple payroll, but the two-Steve era was over.

Harry’s guess: Woz was a virtuoso, which made him the most important figure of the first period of personal computer design. But it also makes it less likely that he would have continued to thrive in the more corporate, team-oriented era that followed. My guess is that he would have put aside engineering in favor of all his other pursuits, from educating kids to Segway polo, no matter what. And I can’t blame him.

4, What if the Lisa had been a hit?

In January 1983, Apple released the Lisa. The innovative and well-equipped machine sported a revolutionary user interface, a mouse, 5.25″ inch floppy drives, and a whopping 1MB of RAM–and a $9,995 pricetag that made it an unsuccessful, out-of-reach oddity in an era when many businesses weren’t sure they wanted computers at any price. By April 1985, the Lisa line was dead. That wasn’t a tragedy for anyone concerned, since the similar and far more affordable (if underpowered) Mac had debuted more than a year earlier.

Harry’s guess: This one’s easy. The only scenario in which the Lisa would have wound up a success would have involved it keeping all its good stuff but getting a lot cheaper–evolving, in other words, into something almost exactly like the Macs of the later 1980s. That didn’t happen in part because the Mac itself came along. But if the Lisa had gotten affordable and flourished, it might have been the Apple computer that continued on to the present day. The biggest real difference might have been the nameplate on the case. Oh, and Apple would have presumably had to hire someone other than Justin Long for its “I’m a Lisa” ads.

5. What if Apple had licensed the Mac OS in the mid-1980s?

From almost the moment that the Mac arrived in 1984, folks were telling Apple that its strategy–selling its own software on its own boxes–was all wrong. Among the naysayers was a guy who knew a thing or two about selling software on other companies’ boxes: Bill Gates. In a famous memo from July 1985, he recommended that Apple license the Mac OS to other manufacturers, and suggested three in particular: Northern Telecom, Motorola, and AT&T.

Apple gave Bill’s advice serious consideration, then declined to pursue it.  (unless you count a different Apple administration’s brief licensing of clones a decade later). For the most part, it’s stuck with its initial software-and-hardware strategy through good times and bad, and taken it into new realms such as music players and phones. The idea is core–pun unavoidable–to what makes Apple Apple. But when Gates wrote his memo, it wasn’t clear that the Mac was going to make it, Steve Jobs had lost his power struggle with Apple CEO John Sculley (although he hadn’t quite resigned yet), and Windows hadn’t shipped. More than most times in its history, 1985 was a time when the company might have decided to license its OS.

Harry’s guess: It’s always a mistake to claim that Apple would have essentially been Microsoft if only it had deigned to license the Mac OS–the move would have been so contrary to its instincts that it probably would have screwed it up. And Windows, unlike the Mac OS, had the advantage of being an extension of DOS, the dominant computing platform of its time. I think it’s possible that a licensed Mac OS might have been quite successful; I also think it’s just as likely that Windows would have come to dominate the market from a sales standpoint anyhow.

6. What if Steve Jobs hadn’t left Apple in 1985?

In 1983, Steve Jobs hired Pepsi president John Sculley to help him run Apple. In 1985, Sculley forced Jobs to resign on the grounds, basically, that he was impossible to deal with.Thus began twelve years of Apple history that were nowhere near as exciting as Jobs’ first reign at the company or his current one.

Harry’s guess: It’s beyond debate that an Apple that had kept Jobs on the payroll would have had a different history than the one that limped along for more than a decade without him. How it would have been different is tough to say, though. Almost anyone would come to the conclusion that being fired was good for Steve Jobs: He went away and founded NeXT (which built the operating system that serves as the Mac OS to this day) and Pixar (one of the most influential and profitable entertainment companies ever). And he eventually returned to Apple as a vastly more seasoned, disciplined person. If he hadn’t spent the years in exile, it’s possible that Apple would have boomed in the 1990s and the iMac, iPod, and iPhone would have come along just as they did. But I think it’s just as likely that Jobs would have been a different, less successful sort of entrepreneur, and Apple a different, less successful sort of company.

7. What if NeXT had succeeded?

Jobs’ second computer startup made an extremely cool workstation that was a decade or more ahead of its time. It just turned out that there wasn’t much of a market for it. The company drifted from business model to business model and received infusions of cash from outsiders such as Ross Perot and Canon for a decade; its life as an independent venture ended when Apple bought it in 1996, acquiring its Unix-based OS and bringing Steve Jobs back into the fold.

Harry’s guess. It’s not hard to come up with alternate scenarios in which NeXT would have been more viable. But they all involve it making products for use by big enterprises, programmers, and/or scientific and academic types–not friendly little computers, music players, and cell phones for consumers. If NeXT had thrived, Steve Jobs might well have been prosperous, respected, and happy; nobody, however, would have regarded him as a god, or even a household name. And I almost certainly wouldn’t be writing this article.

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