(Note: I began a draft of my review of Steve Jobs by Walter Isaacson back in 2011. This week I dug it up, rewrote a lot of it, but the core of my review is the same.)
Summary: Steve Jobs by Walter Isaacson is nothing but a huge, missed opportunity.
Steve Jobs was written by a man who not only didn’t know Steve Jobs, but has no understanding or insight into the world of computers Jobs helped create.
Isaacson had a lot of sources to pull from when he began this book. There was a handful of times where I knew exactly where he had pulled a story or quote, whether it be from Jobs’ commencement address at Stanford in 2005 or story from Andy Herzfeld’s (one of Apple’s first employees) Folklore.org. Or the introduction of the first Macintosh. Or his ‘Values’ talk in 1997 after his return to Apple. Or the awesome interview with him at Wired in 2002.
Isaacson managed to badly summarize the key moments in Apple’s history and Steve’s life because he didn’t have a thorough grasp of the computer industry. I also noticed inconsistencies in how he referred to different computer acronyms and functions within computers and operating systems.
Despite the persistent sense of unease I felt, paragraph after paragraph, I continued reading through the book. Occasionally I was rewarded with anecdotes and details I had never heard before—like the fact that Jobs wanted to rename the Macintosh to be ‘The Bicycle’ (inspired by my favorite Jobs quote).
It wasn’t until I finished the book and listened to John Siricusa’s reaction did I realize how badly Isaacson botched it. Siricusa gave his review in episode #42 of his podcast, Hypercritical, with Dan Benjamin. It’s the best and most (hyper)critical review you’ll ever read on Steve Jobs. As I listened to Siricusa list out all the problems and errors in the book, I kept thinking to myself, “Damn, that’s what I was thinking too!”.
Before getting into all his nit-picky problems, Siricusa first summarizes his take on the biography by referencing an interview with Steve Jobs in the documentary, Triumph of the Nerds (1996). In the interview, Jobs is asked about his fallout with the guy he hired to run Apple, John Sculley. The board of directors at Apple eventually voted to keep Sculley and fire Jobs. Jobs replies, “What can I say, I hired the wrong guy.” (Here’s an excerpt, around the 3:41 mark)
In reference to Isaacson, Siricusa says (my emphasis):

Reading the Walter Isaacson Steve Jobs bio, if I had to summarize my take on the book, I would say, what can I say, he picked the wrong guy to write his bio because Walter Isaacson, for whatever his strengths might be, was absolutely the wrong guy to write the official biography of Steve Jobs.
He continues:
I can’t emphasize this enough—the thing that’s special about this book, because many, many books have been written about Steve Jobs and Apple, is that this is the one book, with the one guy, who had official, authorized access to Steve Jobs. […] It was notoriously difficult to pin down Steve Jobs. He doesn’t like doing interviews. He doesn’t like talking about his personal life at all. So this is the one time that he says, “c’mon, I want you to do a book about me, you can ask me anything.”
And (my emphasis):
The reason I say he’s the wrong guy is Walter Isaacson does not know this industry. The industry Steve Jobs grew up in and defined. That’s strike one. But strikes two and three is that he doesn’t know and he didn’t bother to learn about it. That’s the most egregious sin. It’s like he didn’t feel the responsibility of, “I’m the one guy with the authorized Steve Jobs biography, I know nothing about this industry at all, but I better buckle down and learn.”

[…]

If you don’t know the industry, how can you know what’s important in the life of this person? What Walter Isaacson came in with is sort of a generalist, lazy-person’s knowledge of computers and what he ends of focusing on in the bio are sort of human interest, general interest stuff. Family, friends, relationships, money, gossip. Things that are sort of common to the human experience and he should write about those, but it’s impossible to have any real insight in a life like Steve Jobs if you just look at the parts that are common to all lives. […]

You’re missing out on what’s special.
First, I recommend every read the Steve Jobs bio if you haven’t already. It might suck, but there is knowledge in the book you won’t find elsewhere.
Once you’ve done that, check out episodes 42 & 43 of Hypercritical to hear Siricusa’s full review. It’s awesome.