Pod Insights Big Technology Podcast How Walt Mossberg Built A Deep Relationship With Steve Jobs About this episode Walt Mossberg is a legendary tech journalist and longtime columnist for the Wall Street Journal. This is a preview of our premium Big Tech War Stories Podcast where Mossberg joins to discuss how he formed connections with industry titans like Steve Jobs, Bill Gates, and Jeff Bezos, and what drove their thinking and strategies. In this preview we cover Jobs, discussing his optimism, focus, and unending curiosity that led to long hours of conversation with Mossberg via phone. We also discuss the relationship between the tech industry and the press, where Mossberg has some interesting thoughts, and even some optimism of his own.
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1:03 Alex Kantrowitz? Big 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 up 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.
1:41 Alex Kantrowitz? Jobs, 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 re-coded 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.
2:26 Alex Kantrowitz? And with that, I want to welcome Walt to the show. Walt, welcome.
2:31 Speaker 01 Thanks for having me, Alex.
2:32 Alex Kantrowitz? 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.
2:56 Speaker 01 Well, I think surprisingly, given his certain aspects of his personality where he was, he was very hard-nosed and even rude and mean to people. I 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, gee, his music,
3:36 Speaker 01 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, and from Napster, and but he still had to convince them to let him sell downloaded music at 99 cents a song. And I said to him, because I had recently talked to some of them, I said, these guys don't get it. They're, you know, way behind. They don't understand digital. They don't understand how people want to listen to music now. And he would, he said to me, look, put yourself in their shoes. And he went through a whole explanation of how tough it was for
4:20 Speaker 01 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, you know, that kind of thing. If I talked 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. He was obviously very, very ill. It was the evening it was 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,
5:05 Speaker 01 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, at the request of the editor of the Wall Street Journal, where I was working at the time, and also for the website, one of the websites I co-founded with Kara Swisher, which was called All Things Digital, I was pounding out a a series of personal reminiscences about Jobs, the person. I'm pounding this thing out. My phone rings. It's him. It was, he was not going to be on the record, so there were no quotes to go into my story, but
5:47 Speaker 01 when I talk about optimism, this is what I wanted to, the 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, 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. And 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?
6:29 Speaker 01 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 a CEO, 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.
7:13 Speaker 01 And I'm not talking about what some journalists and analysts who didn't really know him, the picture they painted of him. I'm talking about the real person. He was, he was an optimist.
7:25 Alex Kantrowitz? Yep, 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. 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, but they do something else or they have, you know, other interests that they seem almost more passionate about. Even Bezos, who seemed single track when he was running Amazon, said the most important thing that he was doing was Blue Origin.
8:03 Alex Kantrowitz? Jobs, when you see him talk, just seems serious, on point, totally singularly focused on Apple. Does that, did that come through in your conversations?
8:15 Speaker 01 Oh, absolutely. And I think you've hit on a very, very important point about him. 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. But he was, 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.
8:55 Speaker 01 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, it's, 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. He couldn't.
9:36 Speaker 01 And 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, 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 jobs 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
10:20 Speaker 01 bezel of the phone and if you held it a certain way, it would attenuate the signal. And he glued back from Hawaii, where he was vacationing, held a press conference. You 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 the, 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.
11:03 Speaker 01 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, not the enterprise, not the cell phone carriers, not the stock market, the consumer, the average person, not the, you know, not the tinkerer
11:45 Speaker 01 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, he just wanted to make what I would call information appliances.
12:26 Speaker 01 I'm talking to you right now, it 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.
12:47 Alex Kantrowitz? 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?
13:10 Speaker 01 I 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'd 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 was none. I had nothing to do with it, except they asked me to come be at the party because by then my, I can't remember the year, but my column was, you know, quite well read by the tech
13:47 Speaker 01 industry by that time. 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. I 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
14:28 Speaker 01 and he agreed and I said, asked him what he was trying to do at NeXT and then he talked to me. But I mean, it was, it was a brief encounter. Now, nothing continued from that. Nothing flowed from that. That was just a encounter at a party. He kept working on NeXT $10,000, you know, boxes for researchers and universities and good example is that the first web browser by Sir Tim Berners-Lee was done on a NeXT box. He kept working on that and I kept working on my column and I didn't ever call them and he never called me. The hour and a half phone calls you're referring to were the
15:11 Speaker 01 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.
15:25 Speaker 01 I started getting these phone calls from him at home on Sunday. And, you know, I'm not dumb. I, I knew that I was an important, one of a number of important journalists. That he had to win over, he 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.
16:08 Speaker 01 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, you know, 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. The reason the call was an hour and a half was, we would talk about everything. We would talk about where the industry was going, we would talk about, he would talk about his criticisms of the minutia 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.
16:52 Speaker 01 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 was, and he had a deep well of curiosity. And then he, and he did those calls, I, I don't know whether it was four or five weeks in a row. And, uh...
17:29 Speaker 01 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 sucking up time out of our weekend. But they were fascinating calls and those calls are what started my relationship with him.
17:50 Alex Kantrowitz? 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. And then you write about, 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?
18:26 Speaker 01 No, no, no, no, no.
18:29 Speaker 01 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.
18:43 Speaker 01 Anybody that has wasted their time trying to follow my career knows that
18:50 Alex Kantrowitz? Your first sentence.
18:51 Speaker 01 Starting from the very first line of my very first column.
18:56 Speaker 01 My whole thing was that PCs and eventually other digital devices fell into this category. Were 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 there was really, I mean, there was
19:39 Speaker 01 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. You know, laptops were like. Revolutionary and cool. And a lot of people don't remember that laptops did not even have have little. Not only didn't they have track pads, they didn't have any kind of pointing device. You had to buy, I don't know if you remember this Alex or you're too young, but you had to buy on Windows laptops, you had to buy a mouse or trackpad that hung off.
20:20 Speaker 01 I mean, a track ball, 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. So that was me.
21:02 Speaker 01 I was focused on consumers, not enterprises, and I was focused on ease of use. Well, it turned out that, you know, 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 see, 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.
21:46 Speaker 01 And that was, in my mind, the foundation of the relationship. Now, when you ask, how did he take criticism?
21:54 Alex Kantrowitz? Yeah, let's hear this one.
21:56 Speaker 01 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 that, you know, he called an old hands meeting and he pointed at my column as part of the evidence that the thing was no good and whatever. But even if I wrote, my, my style of, remember, I was a reviewer. The Wall Street Journal had a beat reporter covering Apple, a beat reporter covering Microsoft.
22:38 Speaker 01 But 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 and the hierarchy. I had no responsibility for any of that. My only responsibility was their products. And I got to choose which products are 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, my writing partner, Katie Barrett, who also had a column along
23:18 Speaker 01 with mine, when we would write, when I would, particularly me, if I would write a positive column saying, "This new iMac is fantastic. It'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.
24:01 Speaker 01 I would get a call from Jobs during the 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." Do 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 he has 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
24:44 Speaker 01 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.
25:00 Alex Kantrowitz? Oh, my God.
25:03 Speaker 01 And he would say, you know, I don't think, I think you were too tough on us on this. 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. Yeah, 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 prepared a column that said not one negative word about his product.
25:48 Speaker 01 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.
26:02 Alex Kantrowitz? 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. And 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.
26:45 Speaker 01 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.
27:25 Speaker 01 We could have a relationship where we talked about products. I 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.
27:42 Speaker 01 However,
27:45 Speaker 01 I have still noticed, I still know a lot of the, particularly the reviewers
27:53 Speaker 01 at the different publications. Like my successor at the Journal, Joanna Stern,
28:01 Speaker 01 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.
28:13 Speaker 01 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,
28:38 Speaker 01 yeah, they fed me the PR for the first 20 minutes of whenever I was there. And then, 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 or you're not asking about earnings, you're just asking about You know, why does the Vision Pro cost $3,500? Where can we expect to see you go with this? Which of course, Apple being Apple, they wouldn't exactly tell you, but or ask questions about,
29:19 Speaker 01 well, when will I get one of these to test on my own, which most of the major reviewers have already done? Then I think they'll see, 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, in tech, tech media relations, it's bad. It is.
29:44 Alex Kantrowitz? 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. What does he say? He says, "I thoroughly understand the question, and I will have to leave the answer up to our actions in the future."
30:17 Speaker 02 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?
30:34 Speaker 03 I thoroughly understand the question. And I'm gonna, I'm gonna have to leave the answer, I'm gonna have to leave the answer to, to, to our, you know, our actions in the future.
30:47 Speaker 01 Uh huh.
30:48 Alex Kantrowitz? All right. AKA, 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?
30:59 Speaker 01 It 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.
31:22 Speaker 01 Hard and fast policy on not talking about future products. He clearly, I mean, in 2005, 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. And 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.
32:05 Speaker 01 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.
32:25 Speaker 01 You 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 Karen would back me up on this. The way we would have maybe 14 or 15 speakers. They would be excellent speakers. We would, 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, you know, 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. Over those 17 years, this is how we would plan it.
33:10 Speaker 01 We would have maybe an hour, an hour and a half, the two of us. The date, couple of 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 the speak, what we called speakers. They weren't really speakers because they were just interviewees. There were no podiums or anything like that. But we, it was our view that it was a bad idea to make up a long list of questions.
33:51 Speaker 01 So whether it was Steve Jobs, or Bill Gates, or you know, the CEO of GM, or the CEO, or Bob Iger, or whoever we had, we were interviewing, we did not have a long list of questions. We would tend to go through the speakers, decide who would ask to go first, if it was the two of us, or if it was going to be a solo, who would do the solo. Most of the interviews were actually solos. We called solos, meaning I did it alone, or Kara did it alone. And we would, but we would jointly figure out what might be a good opener, and what topics we had to touch on in the interview. And if it was the two of us, we would decide, well, who would take what?
34:36 Speaker 01 Who would take like the other? So for instance, when famously Mark Zuckerberg broke out in a big sweat, it was because I was hammering him on privacy. He had just come from one of his many privacy scandals the week before. And I was hammering him on privacy. He was having a lot of trouble putting a coherent sentence together. I really wanted to move on to another topic, but he was very flustered. And eventually Kara could see it better than I could, because of the way the chairs were arranged. But she was worried he was going to faint. So, and I could see something was wrong. So I got off the privacy topic.
35:20 Speaker 01 We had other topics to discuss with him. But that's just an example of Kara and I saying, okay, we want to get to this, this, and this. But first, we have to do privacy, because it's important. And I think Kara said to me, why don't you take that? I said, fine. I had actually written stuff about it, you know, and you take that. So that's what we did. It was, there was much, much less planning than people might have expected. We wanted to let the conversation flow.
35:51 Alex Kantrowitz? All right, so I think we can take a quick break, and then go into a very quick segment on Bezos, and then get into Gates. If you're a big technology war story subscriber, if you're a big technology subscriber, and you're seeing this half, if you upgrade your subscription, you can get the second half, where we're going to talk about Gates and Bezos, right after this. And you can do that at bigtechnology.com. All right, we'll be right back.
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