Steve Jobs’ 5 Biggest Mistakes

by Chris Seibold Nov 11, 2009

Steve Jobs was recently named Fortune's CEO of the decade. The choice seemed obvious, Steve worked a lot of magic with Apple turning a company three-weeks-from-bankruptcy into a darling of consumers and investors. On the other hand, an award by a magazine is just a matter of opinion. It is preferable to try to add some sort of metric to Steve Jobs' performance as Apple's CEO. Apple is a publicly traded company so we can use a quick and dirty measure of Steve Jobs' success: the change in stock price. If you had put a $100 in Apple the day Steve was announced as CEO that one hundred dollars would be worth $16,000 today. Try to get that kind of return out of CDs.

With that in mind, it easy to conclude that Steve Jobs is good for Apple. But even the best CEO makes mistakes, let's take a look at some of the biggest missteps by Steve Jobs since his return to Apple (yeah, you won't have to hear about the Apple /// or the flaws of the original Mac).


The iPod Hi Fi

When Steve Jobs is passionate about something you can tell. While most public speakers attempt to show passion by inflection or yelling (insert developers, developers, developers) Steve uses a more compelling technique. He explains why he loves the product and counts on the audience to feel the same way. It usually does.

However, watching Steve introduce the iPod Hi Fi, you could tell he loved the product, but the love stopped there. The wannabee boom box, probably did sound fantastic (not that many listened to it) but people tend to rip music and collect music in a less than audiophile quality so even if the speakers were fantastic very few would ever be able to tell.


Steve Jobs knew that video was the next wave when it came to creating stuff and his solution was iMovie. iMovie was a remarkable program developed by Glenn Reid. The first iteration was simply mind blowing. Well, film pros detested the thing, but anyone who wanted movie editing at their fingertips drooled over the program. Steve likely imagined iMovie would sell a lot of Macs (it sold at least one, to me) and likened the coming video revolution to desktop publishing.

However, iMovie was held back by the technology of the time. To use it you had to have a digital camcorder, and since most people were still on dial up, even if you made a movie it would take forever for anyone to download it.

The interesting thing is that Steve was right about the coming video revolution (say hello to youtube if you doubt that) but Apple missed the chance to ride the wave.



When OS 9 came out it was mostly there to bridge the gap between Classic Mac OS and OS X. Telling people to upgrade to OS 9 from OS 8 just to help out development isn't a good sales pitch. So Apple sweetened the pot: Upgrade to OS 9 and iTools came along for free. You'd get a .mac email addy, some web space and a few other goodies. Mac users loved it and Apple killed it. Why? Because of the cost according to Steve.

So Apple replaced iTools with .Mac (which is now .me). Instead of free, users got to pay $99 for the joy of using Apple's servers. Oddly, almost all of the functionality of the original version of iTools was offered later, and without cost, by other companies. Apple's chance to lock in Mac users to an Apple service was lost for the sake of a few dollars.


The G5

You remember the G5, right? It was made by IBM and was the first 64 bit chip in a personal computer. Not only was the G5 64 bits, it was screaming fast. The chip that would squash Intel.

But, the G5 didn't squash Intel and it didn't move a bunch of Macs. In fact, the G5 held back the laptop line at a time when people were beginning to opt for laptops over desktops. If you wanted a Mac laptop in the G5 era you had to put up with the fact that the G4 was obviously inferior to the G5.

Not only were laptop users made to feel like second class citizens, the chance to really sell 64 bits in all its glory was wasted on a chip Apple wouldn't stick with.


The original iPhone

How can the original iPhone have been a mistake? The thing sold like crazy, people fell in love. The problem wasn't with the sales or the acceptance, the problem was with its limitations.

A pokey EDGE connection when all the apps were web-based, a sky high $500 entry price and developer lock out added up to a device that was a lot less than it should have been. That the original iPhone was so widely accepted speaks more to the state of competition at the time and marketing than the quality of the original iPhone.

This list should tell you something about Steve Jobs and Apple. The easiest thing to take away is that Steve Jobs isn't perfect, but the more important message is that with a few exceptions, Steve and Apple get things right.




  • I’m not sure whether I get why these things are mistakes

    iPod Hifi: yes, underwhelming. Didn’t damage Apple but why bother.

    iMovie: you’re saying it was a great success, but Apple should have built YouTube? I would label that “Apple could have built Youtube”... and as such not so much a mistake as one of MANY different directions Apple could have gone.

    iTools: I tend to agree that could have stayed free and that would’ve been good for Apple. I note you’re not criticising iTunes, just saying it was a mistake to charge for it.

    The G5: You’re not actually criticising the G5, more IBM aren’t you? Or just the PowerPC in general? I don’t think we can say that overall the PowerPC was a bad move for Apple - but I agree it fell behind on the laptops. Originally, the G4 laptops were ahead of the curve… but then they languished.

    The Original iPhone: Should have had 3G? Yes that would have been nice. But at that time 3G/2G hybrid phones were more chunky/heavier than 2G only phones… so Apple chose to keep the phone thinner and lighter. If I’d had the choice of 5mm thicker to get 3G… I’d have chosen 2G like Steve did.

    There are other mistakes Steve has made of course. Nixing the Newton might be one. I think if AppleTV had been able to play AVI files it may have really taken off (and if preventing that feature was a bargaining chip with the studios…. then did it work?). And the biggest mistake is some of the easy changes that could get made (eg MMS on iPhone) but aren’t because Apple tends to focus where Steve focuses… and that has its limits.

    Greg Alexander had this to say on Nov 11, 2009 Posts: 228
  • Quick note: iTools I accidentally said iTunes. And MMS example on the iPhone is something that was eventually fixed, possibly because it was such a well noticed omission… there are many other tiny omissions.

    Greg Alexander had this to say on Nov 11, 2009 Posts: 228
  • Hi Greg,
    Half the point of the list was to point out that the failures of Apple since the return of Steve weren’t all that big. The other half was to point out that Steve Jobs is not magic. Everyone thinks that Steve creates hits with force of personality but that just isn’t true.

    The products actually have to be pretty damn good. It isn’t enough that Apple loves them.

    Why the hell wasn’t the apple tv on the list? What am I thinking?

    Chris Seibold had this to say on Nov 12, 2009 Posts: 354
  • Hehe.. yeah I wasn’t going to mention the AppleTV….. smile

    Greg Alexander had this to say on Nov 12, 2009 Posts: 228
  • A big issue with leading edge technology is having the infrastructure for it.  You used the example of digital cameras.  Attempts for smart phones needed the bandwidth.  We have the Newton now, but it’s called the iPhone.

    I’m not much of a TV watcher, and have absolutely no interest in AppleTV, but have heard that a majority of those who download movies already have boxes and are Netflix customers.  (I’d rather have all of my TV components connected by USB with smart technology that turns on my stereo and remembers that local channel 4 is 654 on my Comcast box, or when my wife hits 7, to automatically go to 7-1 on her TV).

    Howard Brazee had this to say on Nov 12, 2009 Posts: 54
  • “or when my wife hits 7”

    Howard, I like you, I appreciate you comments. But your wife is seven? Dude that is just sick!

    I kid because I love. You’re right, there is a time for everything. One of the Newtons failures was that the rest of the tech world just wasn’t ready.

    Chris Seibold had this to say on Nov 13, 2009 Posts: 354
  • One of Jobs’s biggest mistakes was targeting IBM instead of Microsoft in the mid-80’s and not going after the enterprise market enough (also, Macs were too expensive).  That strategic error has relegated the Mac to minority status in computing.

    His other biggest mistake is the cryptic approval process in their locked-down monopolistic App Store, which is causing a huge backlash among developers and could potentially lead to an exodus to the Android market.

    Beeblebrox had this to say on Nov 14, 2009 Posts: 2220
  • Good thoughts Beeblebrox

    I agree… I guess Apple wants TOO MUCH to be in total control. Of course, this control has helped them in several ways, but hindered them in others.

    I would like to see
    1) Much greater transparency for App approvals
    2) A general attitude of making Apple products work with any and all competitors - much like IBM did to get back on track. BUT naturally work best when it’s Apple-to-Apple
    3) An Apple Enterprise with free reign to do what it takes to get in corporate, run quite separately to the rest of Apple. Perhaps the only way to do that is a joint venture with someone like Oracle/Sun.
    4) Perhaps a deal with either HP or Dell to put OSX on a small PART of their range of computers. There are unprofitable hardware segments where money can be made on software.

    Greg Alexander had this to say on Nov 14, 2009 Posts: 228
  • “One of Jobs’s biggest mistakes was targeting IBM instead of Microsoft in the mid-80’s and not going after the enterprise market enough (also, Macs were too expensive).  That strategic error has relegated the Mac to minority status in computing.”

    This article was written with an eye towards stuff after Steve’s return. I’d say you’re right, the biggest mistake (so far) Steve made was thinking that he was competing against IBM (hardware) instead of competing against software.

    The price of Macs was more the fault of Sculley than Steve.

    The app store is a completely different issue. It is both the best and worst thing Apple has ever done. I don’t see a mass exodus to Android coming though I don’t see that as a bad thing if it happened.

    Chris Seibold had this to say on Nov 15, 2009 Posts: 354
  • Steve might still be a genius and can see that the future is HTML5 and not flash, but the fact of the matter is consumers need flash today. Steve is putting his issue with Adobe before his consumers. -Gauthier, Houghtaling and Williams

    GHWLegal had this to say on Aug 09, 2011 Posts: 9
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