How Walt Mossberg Built A Deep Relationship With Steve Jobs

0:00Big Tech War Stories is my premium podcast for Big Technology subscribers. The show looks back at big moments in tech and speaks with the people who were there about how it all went down. This week, I have legendary journalist Walt Mossberg on the show and wanted to share the first half with you here, where he talks about his relationship with Steve Jobs. It's just too good to keep off this feed. For the second half featuring Bezos and Gates, head to BigTechnology.com and sign up for a premium membership, or use the coupon code in the show notes below. And now, Big Tech War Stories with Walt Mossberg.

0:37Jobs, Gates, and Bezos. These are the names that established the modern tech industry. And Walt Mossberg built deep relationships with them all. A legendary Wall Street Journal reporter who established All Things D and then recoded with Kara Swisher, Mossberg had the ear of these tech titans, writing an influential column they knew, which shaped the public's perception of their products. And so in this crucial position, Mossberg began to learn what made them tick and indeed what drove the tech giants to their success. Today on Big Tech War Stories, we speak with Mossberg about how he built those relationships with these top CEOs, what they were like off camera, and what exactly propelled them to dominate the industry.

1:22And with that, I want to welcome Walt to the show. Walt, welcome. Thanks for having me, Alex. So let's start with Steve Jobs. There's Steve Jobs, the mythology and Steve Jobs, the figure that the media has painted. There's Steve Jobs, the person. And they're two separate people, I believe. And you got a chance to get to know Steve Jobs, the person. So I'd love to start by hearing your recollection of what Steve Jobs, the person was like in your exchanges with him. Well, I think surprisingly, given certain aspects of his personality where he was very hard-nosed and even rude and mean to people.

2:04I mean, a lot of people write about that, and I think it's true. But surprisingly, in the, I don't know, 30 or 40 hours of conversations I had with him privately, and then all the conversations we did on stage with him, I found him to be easy to talk to, open-minded, and basically optimistic. He was hugely optimistic. For instance, I would say to him, when he was doing the iTunes Music Store and the iPod back in those days, and that was something the record industry, the music industry, was reeling from Napster, But he still had to convince them to let him sell downloaded music at 99 cents a song.

2:53And I said to him, because I had recently talked to some of them, I said, these guys don't get it. They're way behind. They don't understand digital. They don't understand how people want to listen to music now. And he said to me, look, put yourself in their shoes. And he went through a whole explanation of how tough it was for them to pivot on their business model and how in his experience talking to them quite a lot, he thought some of them were trying and that kind of thing. If I talk to him about anything to do with tech, he was never pessimistic. Even right to the end. I mean, the last conversation I had with him was six weeks before he died.

3:42He was obviously very, very ill. It was the evening that it had been announced that he was resigning as CEO. And he was going to become executive chairman of the board or something like that. I think he knew he was dying. I'm sure he knew he was dying. In fact, I don't think he thought he was going to be dead in six weeks. I thought maybe he had, in his mind, maybe six months or something like that. And at the request of the editor of the Wall Street Journal, where I was working at the time, and also for one of the websites I co-founded with Karis Wisher, which was called All Things Digital, I was pounding out a series of personal reminiscences about jobs the person.

4:35I'm pounding this thing out. My phone rings. It's him. He was not going to be on the record. So there were no quotes to go into my story. But when I talk about optimism, this is what I wanted to point I wanted to make. He's six weeks from death. He's just resigned as CEO of Apple. And all he wants to really talk to me about is that he thinks he's figured out how to revolutionize the television and the whole business of watching television and the television set itself. I said, well, what do you mean? How are you going to revolutionize it? You know, I'm on deadline, but it's him. So I'm going to ask him some questions and talk to him.

5:19and I said, how are you going to revolutionize? He said, I can't talk about it yet. But he said, when are you coming to the Valley next? Because I'm based in DC and I went to the Valley very frequently. I said, you know, in a month maybe. He said, that'd probably still be too soon. How about in like three months? I'd love for you to come out. I'd love to show you what I'm doing on television. And that's going to be my project. Now that I'm no longer CEO, oh, that's going to be my project. So I think he was always very optimistic about what technology can do. And I'm not sure that that, and I'm talking about the real person, not talking about the guy up on stage doing marketing, which he was a genius at.

6:09And I'm not talking about what some journalists and analysts who didn't really know him, the picture they painted of him. And I'm talking about the real person. He was an optimist. Yeah, it's amazing. Six weeks before death and trying to schedule a meeting three months out. So I watched a lot of your interviews with Jobs and with Gates, who we'll talk about in the second half ahead of this conversation. And one of the things that struck me about him also, and I'm curious what you think about this, is that he seemed serious, like really on task. I think a lot of CEOs today have their job as CEO, oh, but they do something else or they have other interests that they seem almost more passionate about.

6:53Even Bezos, who seems single track when he was running Amazon, said the most important thing that he was doing was Blue Origin. Jobs, when you see him talk, just seems serious, on point, totally singularly focused on Apple. Does that come through in your conversations? Oh, absolutely. And I think you've hit on a very, very important point about him. And obviously, he was a co-founder of the company. I didn't really know him until his second, well, what they call his second coming. His return to Apple when it was almost out of business. And he rescued it. And he led the development of a whole bunch of game-changing products over a fairly short period of time.

7:36But he was totally focused on the company. But interestingly, not in the way you think about business today. I never heard him talk about the shareholders. I never heard him talk about the stock price. The only time I heard him talk about the market cap was the day their market cap surpassed Microsoft's, which he said, this was publicly on stage. Kara, I think, asked him about it. And he said, to those of us who've been in the industry a long time, it's surreal. But he says it doesn't have much to do with how we run our company and why we come to work every day. It just doesn't matter. But privately, in hours and hours and hours and hours of conversations, in person, on the phone, whatever, he never, ever mentioned the stock price.

8:32And not only that, and you can double check me, but I don't think he ever appeared. This is in the second coming. I don't know about in the very early years after their IPO, but in the second coming, starting in 1997, I don't think he ever appeared on one of those quarterly earnings calls. He considered it not important to his personal mission or job With one exception They did have a kind of a mini crisis With one of the models of the iPhone Where they had put the antenna on the outside bezel of the phone And if you held it a certain way It would attenuate the signal and he flew back from Hawaii where he was vacationing, held a press conference.

9:32You might remember this. They gave away for free rubber bumpers that went around the outside that took care of the problem. I'm pretty sure that phone sold very well. They basically solved what could have been a big deal. And I think that was close enough to one of these quarterly calls that he did appear for some period of time on the call. That's the only exception I can think of. So the point I'm trying to make is he was very, very focused on the, not just on the company, but particularly on the products. And I'll go further. He was one of the few tech executives that I had the privilege or the experience of covering who was just laser focused on the consumer.

10:28Not the enterprise, not the cell phone carriers, not the stock market, the consumer, the average person. Not the tinkerer Who wanted to open it up And do things with it And all that kind of stuff He wanted to make a Easy to use Just open it up and it starts up And you can do what you need to do with it Thing for consumers I know people think that was marketing But it wasn't This is what he cared about And it was different than Gates who was also single-minded in those days on his company. This was different than anyone else. He just wanted to make what I would call information appliances. I'm talking to you right now.

11:24It happens to be on an iPhone. I could be talking to you on a Mac. I could be talking to you on an iPad. Those things are all in that design tradition. That's why he cared about design as much as engineering. So yes, he was serious and he was laser focused. And you ended up building a pretty deep relationship with him. And I think a lot of people are curious how you were able to do that. So you start your relationship with Jobs by meeting him at a party. And that eventually develops into what seems like weekly 90-minute phone calls on Sundays, speaking with Jobs. So how did you go from point A to point B in your relationship with Jobs?

12:06I didn't. There was no continuity between those two things. Somewhere in the period of his exile at Next, you know, was during that period in 1991, I started my tech column and the journal had some advertiser event or something. They had a party in Silicon Valley. I wasn't a speaker to my recollection. I had nothing to do with it, except they asked me to come be at the party. Because by then, I can't remember the year, but my column was quite well read by the tech industry by that time. And so I went to the party. And at some point in the party, Steve Jobs walks over to me. Now, I knew him. I knew what he looked like.

12:57I knew lots of stuff about him, but I had never met him. And I had no reason to meet him. I didn't ever review a Next computer because it wasn't a consumer product. And all I ever covered were consumer products. Came over to me. It was maybe about a 15-minute conversation. He said he liked my column, which was nice of him. I said something about how screwed up Apple was. And he agreed. And I said, asked him what he was trying to do it next. And then he talked to me. But I mean, it was a brief encounter. Now, nothing continued from that. Nothing flowed from that. That was just a encounter at a party.

13:41He kept working on Next,$10 ,000 boxes for researchers and universities. And a good example is that the first web browser by Sir Tim Berners-Lee was done on Nextbox. He kept working on that, and I kept working on my column. And I never called him, and he never called me. The hour and a half phone calls you were referring to were the next time I talked to him. And that was very shortly, within like two weeks or a week after he came back to Apple in 1997, I started getting these phone calls from him at home on Sunday. And, you know, I'm not dumb. I knew that I was an important, one of a number of important journalists that he had to win over.

14:38He had to win over a lot of constituencies who were under the correct impression that Apple was almost dead. And he had to persuade these constituencies. I'm sure analysts and journalists and investors and whoever, his own employees in some cases, and his vendors and all of that, and the retailers. He had to convince these people that Apple had a future, that he had a plan, whatever. So I'm not dumb. I thought, well, he's calling me because I'm on the list of people he has to bring along and convince. But it turned out these phone calls, and he did some of that at the beginning of the call, the first call.

15:24The reason the call was an hour and a half was we would talk about everything. We would talk about where the industry was going. And we would talk about, he would talk about his criticisms of the minutiae of design of the Apple computer products that existed at that time. Because he hadn't done his own yet, you know, and he had studied them. And so one minute we'd be talking about, I don't know, an icon or an angle of plastic somewhere on the computer. and the next minute we'd be talking about what was Microsoft doing, what was Intel doing, what was HP doing, whatever. I mean, he had a fast mind, everybody knows that, and he had a deep well of curiosity.

16:16And he did those calls, I don't know whether it was four or five weeks in a row, and you know it sucked up a part of our Sunday I think they were like early evening calls usually or later in the evening and after a while my wife got annoyed that it was like second up time out of our weekend but they were fascinating calls and those calls are what started my relationship with him. And a relationship between journalist and subject is kind of a unique relationship because you can have these deep conversations, talk an hour and a half, I mean, definitely enjoy speaking with each other, talking about the industry, where things are heading.

17:01And then you write about the subject. So how did the relationship then deepen after that? Was it that Jobs, because you're not going to write nice things all the time. Was it that Jobs was able to sort of see criticism and say that was fair? where did the relationship go from there? No, no, no, no, no. Here, let me explain. Let me explain it this way. So I just finished telling you that he was focused on making products that were easy to use for consumers. Anybody that has wasted their time trying to follow my career knows that starting from the very first line of my very first column, my whole thing was that PCs and eventually other digital devices fell into this category.

17:59We're all too hard to use. They're basically were made by geeks, for geeks. The columns and articles written about tech were written by geeks, for geeks. I mean, I was doing something different and I believed, And to the extent I crusaded for anything consistently for 27 years, it was these things needed to be easier, fewer bugs, fewer hassles in general in using them. And if you looked at the landscape of who was making computers, because it was really, I mean, there was the early days of digital cameras were around the early 90s when I started. And there were certainly some cell phones that I wrote about, but mostly it was computers.

18:47You know, laptops were like revolutionary and cool. And a lot of people don't remember that laptops did not even have little, not only didn't they have trackpads, they didn't have any kind of pointing device. I don't know if you remember this, Alex, or you're too young, but she had to buy on Windows laptops, she had to buy a mouse or trackpad that hung off, I mean a trackball, I'm sorry, that hung off the side of the laptop and plugged into one of the ports. that's what you had to do for a few years before they just started to build it in apple was if not the first one of the first to build a pointing device in and in their case the very first one was a track ball and they made sort of an indentation in the lid so that when you closed it it closed over the track the track ball was sunken as much as they could and the Lid had a combination for that.

19:56So that was me. I was focused on consumers, not enterprises, and I was focused on ease of use. Well, it turned out that I spent just about as much time with Bill Gates as I did with Steve Jobs, and I spent just about as much time with lots of other people in Silicon Valley. I would go to Silicon Valley. I would stay there for a week. I would see 15 or 20 companies. Many of those trips, I didn't see Apple at all. So I mean, I saw lots of companies and covered lots of things. But his philosophy and his interest in what he was doing coincided very closely with mine. And that was, in my mind, the foundation of the relationship.

20:48Now, when you ask, how did he take criticism? Yeah, let's hear this one. So because what they were doing generally coincided with what I thought everybody should be doing, most of my Apple reviews were generally positive. Some were very negative. Like I remember I wrote a totally negative review of Mobile Me, which they canceled. And, you know, he called an old hands meeting and he pointed to my column as part of the evidence that the thing was no good and whatever. But even if I wrote my style of – remember, I was a reviewer. The Wall Street Journal had a beat reporter covering Apple, a beat reporter covering Microsoft.

21:35But when I went to those companies, they knew I wasn't going to post something the next day. I had no responsibility for their earnings, for who got what job in the hierarchy. I had no responsibility for any of that. My only responsibility was their products. And I got to choose which products I reviewed, which companies. You know, I had a lot of pitches and I had freedom to choose. The editors never got involved. So even when I wrote writing partner, Katie Barrett, who also had a column along with mine, And when we would write, when I would, particularly me, if I would write a positive column saying, this new iMac is fantastic.

22:29It's the best desktop computer on the market. And if you're looking for a desktop computer, I recommend you buy it. But in every single column, whether it was Apple or somebody else, even if the column was predominantly positive, I would have a section on downsides because everything has downsides. Even essentially good things have downsides. And Jobs would call me. I would get a call from Jobs during a workday at my office. And, you know, sometimes he would call, one time he called me and he said, you wrote that the iMac should have an SD card slot in it, which a lot of other computers already had.

23:20Do you still believe that? I said, yes. He said, thanks and hung up. I think he was in the middle of a meeting and somebody said, well, Mossberg wrote this, maybe as a point. and Jobs couldn't remember. He wanted to double check, so he called. That was one kind of call, but the kind of call I want to talk about is the call where he's complaining about the criticism in a generally positive column. He'd call and the beginning of his phone call would be, hey, well, I'm not calling to complain about your column. And what that meant was, I'm calling to complain about your column. Oh my God. and he would say you know i don't think i think you were too tough on us on this that he would be focusing on the last part of the column which was the downsides usually and he would say i think you're wrong about this or i think you're you're not being fair to us on this and you know he wasn't yelling or screaming or anything which he was perfectly capable of.

24:23Yeah, I did have arguments, usually in person, when we were talking about various things. But these calls, he was generally calm, but he would have preferred a column that said not one negative word about his product. And he complained, and I listened. And I said, you know, I disagree, Steve, I just disagree, but I'm happy to hear what you have to say. And that was his method of complaining to me. You know, it seems like this type of relationship between the press and a tech leader is almost a lost art today. And I'm curious what you think. And this is something that I've been thinking about, you know, watching your interviews and through this conversation of whether this type of relationship is even still possible today, where tech, a lot of tech leaders have come to view the press as overly hostile.

25:21and also I think probably more importantly that they view and maybe this is right that they have avenues to audience that they can directly communicate with audience and not have to go through for instance the Wall Street Journal to speak with those consumers that they really care about so much so I'm curious what your thought is. Two things I want to stress again that I was not the person covering Apple or covering Jobs' performance as a CEO. That was not my job. My job was strictly to review products. And that means that when you talk about the press, it's a very specific, narrow role. And because many of these people cared a lot about their products and knew that I had some influence with a large number of people, not just my readers, but other journalists, whatever, we could have a relationship where we talked about products.

26:25I think you're right that there's a much greater hostility in Silicon Valley toward the tech press and the press in general than there was even seven years ago when I retired.

26:40However, I have still noticed, I still know a lot of the, particularly the reviewers at the different publications, like my successor at the journal, Joanna Stern, my former colleague, Lauren Good at Wired, my former colleague, Eli Patel at The Verge, where I was the executive editor. for a couple of years. And my observation is that these people, when some big announcement or some big thing is coming up, the companies will open the door and let a seasoned reporter like these in and talk to them. Now, I don't know if the relationship is exactly like mine. I feel like I had, yeah, they fed me the PR.

27:37for the first 20 minutes of whenever I was there. And then we had a real conversation. I don't know whether that's still the case today, but I think it would be wrong to say they've shut all the press out. If you are going and you're not asking about the stock price, you're not asking about earnings, you're just asking about why does the Vision Pro cost$3 ,500? and where can we expect to see you go with this? Which, of course, Apple being Apple, they wouldn't exactly tell you. Or ask questions about, well, when will I get one of these to test on my own, which most of the major reviewers have already done.

28:22Then I think they'll see reviewers, not just Apple. I'm talking about everybody. But reviewers are just one section of the press. And I think it's, look, it's bad. A lot of what's happened in tech, tech media relations, it's bad. It is. Yep. Okay. I have one last jobs question for you and then we'll go to break and talk about Bezos and Gates. So I just, there's an art to asking him a question, isn't there? Because I was watching one interview with him, you and Kara and him in 2005. and you had him dead to rights on the phone. He was dancing around trying to say that there was not going to be an iPhone and then eventually he admits it.

29:07What does he say? I say, he says, I thoroughly understand the question and I will have to leave the answer up to our actions in the future. In fact, you know, the same hard disk you use in the iPod mini is now in some Samsung and Nokia cell phones. I know that you could put music software, music firmware in there and all that, plug headphones into it. Why isn't that true, that it's going to move into the cell phone? I thoroughly understand the question. Excellent. I'm going to have to leave the answer to our actions in the future. Uh-huh. All right. A.K.A. we're building the phone. When you were going into a conversation with Jobs, how did you think about the type of questions that you had to ask him?

29:56it was one year and i can't remember which year it was where he just outright lied and said we're now working on a phone that's not the one you're referring to but even the one you're referring to i mean you know they always had a policy and i'm not saying they're the only company that did but they had they were certainly the company that had the most uh uh hard and fast policy on not talking about future products. He clearly, I mean, in 2005, the phone came out in 2007. They were well down the road of designing that phone. And he just didn't want to say that. And, you know, once the phone was out, he explained, you know, we thought it was better to build the iPhone into a phone because we thought everything was going to be ingested into the phone and played back from the phone, whether it was music, video, text, whatever it was.

30:51And that's, we now know that to be true. He was evasive at best about that on stage. And you know, nobody likes to be lied to or misled. So Karen and I, I mean, we enjoyed interviewing him very much. The audience enjoyed listening to him very much because he was thoughtful and would explain things. But on that particular thing, it annoyed us, to be honest.

31:21You asked me about how did we think about the questions we were going to ask. You probably will not believe what I'm about to say, but this is the 100 % God's honest truth, and Kara would back me up on this. We would have maybe 14 or 15 speakers. They would be excellent speakers. I mean, over the 17 years or something like that, that we did the D conference and then the Code Conference, which are the same conference with a different name. And we own the Code Conference. Dow Jones owned the D conference. But we independently and without interference ran both conferences. And there were some small changes, but it was basically the same thing.

32:04Over those 17 years, this is how we would plan it. We would have maybe an hour, an hour and a half, the two of us. a couple days before the conference opened. We would have arrived at the resort. There were a lot of logistical things going on, as you can imagine, but we weren't very much involved in that. We did rehearsals of who's going to come onto the stage, from what entrance, when, and that kind of stuff. We had all that stuff. And our policy was never to give what we called speakers. They weren't really speakers because they were just interviewees. There were no podiums or anything like that.