Answer by Jonathan Brill, Steve Jobs amateur historian, on Quora

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

1. For most of his life, he was very bad at running things that involved people, product teams, businesses, meetings, etc.

2. Being wrong so often so early and eventually finding a mentor changed him 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 to 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.

Jobs and John Sculley

At NeXT (1985 to 1996)

  • He was right about hiring Avie 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 probably couldn't have influenced. He never did have a successful business-to-business win.
  • He was wrong, for the most part, about 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 Avie, and all the money and opportunity wasted was Steve and the other people he hired and subsequently mismanaged.

Jobs and the team of NeXT at one of the famous early meetings at his place in Palo Alto

At Pixar (1986 to 2006)

  • He was wrong about buying Pixar and admitted this consistently for a decade after doing it. Pixar lost him money every single year until he renegotiated its distribution deal with Disney and eventually sold it. But Pixar 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, which was similar to what he was trying to do with NeXT. Pixar completely failed at this, was horrible at it, and didn't want to do it anyway. If anything, it kept Pixar from doing what it was meant to be doing: making digital films.
  • He was right about not interfering with Pixar's culture or 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 Jobs credit for that.
  • He was completely right for negotiating all three of Pixar's deals with Disney (its first crappy but necessary one, its second really good one, and eventually its sale), and although the product and the art were all Lasseter and Catmull, Jobs probably got five to 10 times more out of Disney in the second deal than any other human it had access to. At that time of his life, this deal was his strongest suit.
  • He was superduper 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.

Jobs and the creative team behind the ridiculously successful Finding Nemo, including John Lasseter, the legend himself (second from right). Finding Nemo was the tipping point that proved Pixar's value to Disney and ultimately won Jobs the leverage he needed to get Pixar such an unprecedented valuation. Prior to Nemo, some thought the company could be a flash in the pan.

At Apple (1997 to 2011)

He made so many good, major decisions it would be nitpicky 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 decisions 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 in which he could have been a bit more or less aggressive, he had four or five 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 benefited Apple. From his coup in getting Bill Gates to commit to supporting the Mac and investing $150 million, 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, if it had gone south, could have killed the turnaround before it started.

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

Jobs 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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