In conversation: Walter Isaacson

In his final months, Steve Jobs opened up all aspects of his life to his sanctioned biographer, Walter Isaacson, granting more than 40 interviews. In an exclusive Canadian interview, the author of Steve Jobs talks about the computer mogul’s genius, and his dark side.

Q: You write that Jobs was “the ultimate icon of inventiveness, imagination and sustained innovation,” but you could also add master salesman to that list. Wasn’t his greatest product himself?

A: No, I think his greatest product was actually Apple, because it combines his marketing skills with his engineering and design skills. At Apple, everything is integrated—all functions of the company. He was a master showman; he knew that the unveiling of a product should be a grand moment. But he personally helped design the packaging, so when you opened an Apple product you felt a bit of excitement as you saw the iPhone in the little cradle. I know that seems silly and small, but it was marketing tied in with the sort of whole aura of owning an Apple product.

Q: So was his ability to synthesize all of these various things in itself singular?

A: Yes. Look at the grand philosophy of Steve Jobs: it’s to control the user experience from the silicon chip to the shirt on the store clerk. The hardware, the software, the content and the devices are all tightly integrated, and the marketing is part of that as well. Companies like Microsoft and Google make software they license out to other people who put it on hardware and it’s sold in other people’s stores. That’s a good business model, but it doesn’t make for artistically pure and delightful products.

Q: When Jobs first approached you to write a biography about him in 2004, you turned him down. Why was that?

A: Well, in a casual conversation, he said, “Would you ever think of writing a biography of me?” And I thought, well, he’s younger than me, and in the midst of an up-and-down career, so I said: “You know, maybe 20 years from now, when you retire.” I didn’t realize that he was sick, and once I did I also realized he was transforming industries while battling cancer, and what a dramatic story that was.

Q: But the turning point came when his wife, Laurene, approached you in 2009 and said it was sort of now or never?

A: Yes, we just happened to be together, and she mentioned, “If you’re ever going to write about Steve, you ought to do it now.” It was right after he went on his medical leave that involved a liver transplant in ’09, and I hadn’t really focused on the fact that he was that sick. He had just transformed the music industry and was doing it to the telephone industry, so it was a pretty dramatic time.

Q: He was a famously controlling guy, yet he pledged that he wasn’t going to interfere with your work. Did he keep that promise?

A: Yes, except for a cover he thought was ugly. He started expressing that sentiment strongly to me, and said he would only keep co-operating if he got some say over it. I thought that was a great offer, since he had a great design sense.

Q: What did he object to about the first cover?

A: Oh, it had a little picture of him when he was young inside of an Apple logo. It was gimmicky.

Q: When he called you, was it one of those infamous Steve Jobs conversations?

A: Well, he expressed himself clearly and forcefully, but I knew enough about Steve that it neither surprised me nor worried me, because that was his way of being honest. He could be brutal, but it wasn’t something you were supposed to take personally.

Q: He was also a charismatic figure with an ability to get people to buy into his vision, which was so powerful his friends referred to it as his “reality distortion field.” How did you deal with that?

A: I tried to talk to as many people as I could. The tough thing about Jobs is that he had such a strong personality that those around him remember the exact same meeting in different ways, like the movie Rashomon. Even the scene of his resignation from Apple—I interviewed Steve and three other people, and I got four different versions.

Q: Your book is filled with examples of Jobs’s wilful cruelty to others. Is there one instance of his callousness that really stood out for you?

A: No, just the opposite. He could be tough on people, [but] it was never deeply cruel. It was all about the moment, and it ended up creating a team of brutally honest star players who loved to have strong conversations and disagreements. Once you learned to take it, it was in some ways inspiring.

Q: Inspiring for some people, right? I mean, you’ve quoted one of his friends saying that his big question for Steve was, “Why are you so mean?”

A: Right, but that’s about snapping people’s heads off, or saying rough things. You judge it by the outcome, and even the friend who said that remained close to Steve to the end, and was at the memorial service.

Q: One of his former girlfriends suggested to you that he had narcissistic personality disorder, and the former CEO of Apple called him bipolar. Do you think there was an element of mental illness in Steve Jobs?

A: He had an incredibly intense personality, and certainly felt like he was special and all the rules didn’t apply to him. But I don’t think there was a mental disorder.

Q: Jobs was adopted at birth into what was a pretty loving family, but some people still see that as an explanation for his later behaviour. Do you think he had abandonment issues?

A: He said his adoptive parents made him feel special and chosen. But I do think that there was a journey throughout his life for understanding and enlightenment that had, as one of its elements, figuring out who he was and his place in the world.

Q: You’ve dealt with that spiritual side of Jobs too, what you call “his compulsive search for self-awareness.” Was he self-aware?

A: Oh, yeah. He even had a good sense of humour about himself. If you asked, “Why are you so tough on people?” he would say, “That’s who I am. I don’t want to be one of those artificially polite people who never can make a dent in the universe.”

Q: That attitude manifested itself in a kind of binary viewpoint as well, where products were “amazing” or they were “sh—y,” and people were “enlightened” or they were “a–holes.” How was that outlook linked to his success?

A: I think it gave him the temperament of an artist, which is either “It’s perfect” or “It sucks.” That separated him from most technology executives, who put out version 3.1, then 3.2, and never try to nail it. I think that passion was also the reason he wanted end-to-end control over all the products he made. I’m not a psychologist, so I don’t know what causes somebody to become such a perfectionist, but that’s the way he looked at the world. Even the original Macintosh team, he made them sign the inside of the computer case because, he said, “real artists sign their work.”

Q: In the book there are a lot of scenes of Jobs crying when he’s confronted, or told no, or even when he’s happy. Was that manipulative, or was he really that fragile underneath it all?

A: I don’t think his crying was manipulative, I think he was a very emotional person who could be deeply touched by the people he loved, such as his wife, or by a great design, or even a beautiful piece of ad copy.

Q: In 1985, he was ousted from Apple, the company he had founded. What lessons do you think he absorbed from that?

A: I think his real learning experience was after, at NeXT Computer, where he got to indulge all of his best and worst instincts. He wanted to make the product a perfect cube, and over-designed it so that it became overpriced and flopped in the marketplace. So I think that once he came back to Apple he realized he had to be more sensible and more mature. In a broader sense, that’s the whole narrative arc of the book, whether it’s in his personal life or in the way he ran Apple the second time or even the way he handled cancer, which was in a romantic and poetic way at first, but he quickly then looked for the most advanced scientific ways to handle it.

Q: What about his relationship with money? Compared to a lot of moguls, he lived a fairly simple life with a modest house in Palo Alto.

A: Yes, he lived in a normal house in a normal neighbourhood, having dinner almost every night around the kitchen table with his family. He didn’t try to become a celebrity or have an entourage. When he was very young and went to India on a pilgrimage, he was penniless, and a few years later he was worth more than $100 million. He said money didn’t matter to him much when he had none, and it didn’t matter to him much when he had all he could possibly want.

Q: He was a guy who was capable of acts of generosity, but not particularly generous. You write that his philanthropic foundation was left to wither.

A: Right. His wife is a very noted and active venture philanthropist who has started Education Track, which is a great after-school program in America, but Steve focused more on work. And I think that when we look at what’s going to transform education, all the good work of the non-profits might not end up being more important than the invention of the iPad, which could transform education for everybody.

Q: You quote Bill Gates as saying that he wished he had Steve’s taste. But in some ways Jobs’s obsession with design was almost paralyzing. You tell this amazing story about him refusing to put on an oxygen mask after his liver transplant because he didn’t like its looks. Did he care too much about form?

A: Well, he cared passionately about it. But how else do you explain why the iPod and the iPhone and the iPad were completely transformative, whereas rival products have trouble catching hold? There’s an artistry infused into them that doesn’t exist in HP tablets or Microsoft music players.

Q: You write that Jobs was a genius, but not overly smart. What do you mean by that?

A: He didn’t approach things in the rigorous, analytic way that a Bill Gates would. When Steve came back from India, he said, “I learned the importance of intuition as opposed to just relying on Western rational thought.” And that ability to use intuition, imagination and aesthetics in assessing a problem allowed him to think differently. He was ingenious more than simply being really smart.

Q: Sometimes that became a trap. When he was diagnosed with pancreatic cancer, he spent nine months trying to heal himself through juices and diet. How he could he be so dumb?

A: Well, he had a poetic, alternative aspect to his personality that went back to his hippie days. His romantic side first looked for alternative ways to deal with it. Then he engaged his rational side and ended up with the most advanced cancer treatments based on DNA sequencing and targeted therapies. So, as always, with the cancer, with his work, with his personal life, the romantic side of Steve connects to the sensible side of Steve.

Q: The devices he created or helped create at Apple are a huge part of his legacy right now. But technology changes so fast that soon even the most amazing of them will be obsolete. Will his accomplishments seem so amazing 20 or 30 years down the road?

A: I think he will be judged by how well his greatest creation, Apple the company, fares. Devices come and go. The question is, can you continually reinvent the future by connecting artistry with great engineering? And I think at the moment, the people at Apple who trained under him can keep that legacy alive, just as the people who trained under Walt Disney could do it.

Q: Did the public reaction to his passing surprise you?

A: The emotion surprised me, but it’s connected to the emotion inherent in the products he made. He knew how to make a connection. I can’t imagine any other business leader provoking this outpouring upon their death. I just think people felt that Steve Jobs was able to create things that showed he had an understanding of our desires.

Q: In the book, you compare him to Henry Ford and Thomas Edison, and say he’ll be the sort of business leader who will be remembered 100 years from now. But you’ve also written biographies of Benjamin Franklin and Albert Einstein, and you don’t invoke their names. Jobs doesn’t belong in that pantheon?

A: I think he’s very much like Benjamin Franklin in being inventive. Franklin knew how to tie imaginative ideas to practical products—the lightning rod being the best example. And he was always curious, always driven. As for Einstein, he’s in a different quantum orbit. He was the ultimate person who knew how to think different, to use the words in Steve’s famous advertising campaign.