What Did Steve Jobs Get Wrong in His Career?

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Answer by Jonathan Brill, Steve Jobs amateur historian

Every business leader should feel better after learning two things about Steve Jobs:

  1. For most of this life he routinely made catastrophic errors while running things that involved people such as product teams, businesses, meetings, etc.
  • Being wrong so often, so early, and eventually finding a mentor, changed that so drastically that he became a legend, and perhaps the most effective business leader of the modern era.
  • But first, the bloopers:

    At Apple (1976 - 1985)

    • He was wrong about the Lisa and the Mac (which was a product failure and sales flop before being re-everything'd and relaunched after he was gone). Although he was brilliantly right about the marketing for Macintosh, he was running the product team that produced a non-viable product to market at launch.

  • He was wrong about recruiting and hiring John Sculley to lead Apple (Sculley later had him thrown off the Mac product and basically engineered him out of Apple).
  • He was wrong in how he managed people at Apple, including all the managers who stood with Sculley over Jobs in the showdown, in some cases because he was just kind of horrible to them.
  • He was wrong about hardware being more important than software in the early stages of the PC industry.
  • At Next (1985 - 1996)

    • He was right about hiring Avi Tevanian, right about the market opportunity, but wrong on timing. He was about five years off, and really the market was won and lost and won again in a way that he likely couldn't have influenced anyway. He never did have a successful Business to Business win.

  • He was wrong about most of how he ran the business, including the failed opportunities with IBM and other key potential partners.
  • We could say he was right for selling the company to Apple, but really you'd have to confine his role here to negotiating. Everything that was good about it was Avi, and all the money and opportunity wasted was Steve and the other people he hired and subsequently mismanaged.
  • At Pixar (1986 - 2006)

    • He was wrong about buying Pixar and admitted this consistently for 10 years after doing it. It lost him money every single year until he renegotiated their distribution deal with Disney and eventually sold it, but it was sold for value that he didn't create and had nothing to do with (short of funding it and handling negotiations).

  • He was wrong about trying to get Pixar to sell business computing platforms, similar to what he was trying to do with Next. They completely failed at this, were horrible at it, and didn't want to do it anyway. If anything it kept them from doing what they were all meant to be doing: making digital films.
  • He was right about not interfering with their culture, their management choices, or how the company was run - and basically yielding everything to Ed Catmull, a better manager than Jobs would ever be - but that was all part of his agreement with Catmull, so it's difficult to give him credit for that.
  • He was completely right for negotiating all three of their deals with Disney (their first crappy but necessary one, their second really good one, and eventually their sale) and although the product and art was all Lasseter and Catmull, Jobs probably got 5-10x more out of Disney in the second deal than any other human they had access to. At that time of his life it was his strongest suit.
  • He was super duper right about accelerating Michael Eisner's departure from Disney with an orchestrated, public, smear campaign and even more right for building a very close relationship with successor Bob Iger, who would eventually buy Pixar, making Jobs the largest shareholder and then successfully fight to have Jobs join the board.
  • [Pictured here] are Steve Jobs and the creative team behind the ridiculously successful Finding Nemo, including John Lasseter, the legend himself. Nemo was the tipping point that proved Pixar's value to Disney and ultimately won Steve the leverage he needed to get Pixar such an unprecedented valuation. Prior to Nemo, there was still some thinking they could be a flash in the pan.

    At Apple (1997 - 2011)

    He made so many good, major decisions it would be nit-picky to highlight the few errors in judgment he had. He took major, company-threatening risks constantly throughout his tenure and most of them paid off in spades. Most of the product calls that get called mistakes now seem to be sound, reasonable choices at the time. Of course he didn't buy into the idea of third party apps for the iPhone, it was a new product and something like that hadn't really worked before for Nokia or Rim.

    But for every minor decision where he could have been a bit more or less aggressive, he had 4-5 decisions where he just completely nailed something that would have been impossible for anybody else. At this point of his life he was a better manager, better co-worker, and more responsible person than he'd ever been.

    He was still a bit rage-y and kind of merciless on occasion, but if anything those things benefitted Apple. From his coup in getting Bill Gates to commit to supporting the Mac and investing $150m, to cutting many of the highest profile and most beloved products in the Apple development lab because they just weren't consistent with his vision for the company, all of these are crap-your-pants risk level moves, any one of which could have killed the turnaround before it started if they had gone south.

    His second stint at Apple is probably the model by which all other tech CEOs will be judged for decades, and you'd have to conclude that much of that came from so much damn experience being wrong before he took it back over.

    [Pictured here], Steve introduces the iMac in 1998, the first real indication that something at Apple has changed, and that the personal computer market was entering a new era.

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