The Beginning Of Tech Giants with Steven Levy, Editor at Large at WIRED

(Intro Narrator at 00:00:03) Hello, my friends. Today we're talking to Steven, editor at large at WIRED, and we discuss Steven's writing on the beginnings of tech giants such as Facebook and Google, how Mark Zuckerberg's dream became the Facebook we know today, and why journalism has changed so drastically since Steven started in the late seventies.

(Intro Narrator at 00:00:28) All of this right here, right now on the Modern CTO podcast. Here we go.

(Joel Beasley at 00:00:34) This is the Modern CTO podcast. You've been writing for a long time. I was hoping you could quickly summarize from the beginning of your interest in writing to where we are today.

(Steven Levy at 00:00:52) Sure. I went to grad school in literature and realized I wasn't cut out to be a scholar. So I started to become a journalist and started writing and was writing about all sorts of stuff. I was super interested in music, so I wrote a lot about that. I interviewed Bruce Springsteen and Bob Marley and then moved to New York City with my girlfriend, who's now my wife. And in 1981, someone suggested I write a story about hackers, computer hackers. I'd never heard of them. I'd never touched a computer at that point, but I did a story for Rolling Stone. And I was fascinated by those people and that world, and I just wanted to write about it more and more. So for forty years I've been writing about that subject, which to me is just one big subject, which is how the digital transformation has changed everything we do and changed who humans are. So to me it's the big story of our time, and I've been honored to have covered it from the front lines.

(Joel Beasley at 00:01:59) And then how are you spending most of your time today?

(Steven Levy at 00:02:01) Well, today I had a couple of guys in to switch some air conditioners in my apartment, and we did some meetings and edited an interview I just did with Steve Case, the founder of AOL. He has a new book out, and I try to keep up with all the OGs of technology that are still active, as well as try to meet new people who are just raw startups, and see what they're doing. So I'm lucky enough at WIRED to be able to cover the whole of what we do, which is everything from AI to who the next CEO of Amazon is. Right? So I get to cover all that stuff, which is a lot of fun. And now that we're traveling again, I get to hit the road again. So it's really been great because I get a lot of freedom there to just cover the waterfront of what WIRED does. And during the pandemic, I talked to epidemiologists. So that was fun. I did a series of interviews with this guy named Larry Brilliant, who was the guy who helped eradicate smallpox, and he had amazing things to say about the COVID pandemic. And we did a series of interviews. So I get to do all kinds of stuff. Technology really is the subject that covers everything. It used to be a little backwater of journalism, and now it's center stage.

(Joel Beasley at 00:03:36) Yeah. I followed Steve Case for a little bit. I think he had a book called The Third Wave or something like that.

(Steven Levy at 00:03:42) Exactly. I interviewed him for that. He reminded me we talked a lot when I interviewed him for The Third Wave. In the late nineties I wrote a story about AOL and also the other online services at the time, like Prodigy and CompuServe, if you remember those. And the title of the column for Newsweek was "Dead Men Walking." And I talked about how the internet was ending that era where we would subscribe to a service and that would be how we'd get our email. I said the internet is going to blow that up, and if you were a business, you weren't going to contract with AOL to run your business. It would be on the internet. And Steve Case hated that column when it came out, and because AOL thrived for a few years afterwards, did that big merger, he always used to say, "Well, Levy was wrong." But ultimately that was right. So when I interviewed him for The Third Wave, maybe six or seven years ago, we went over those grounds. And this time we just talked about whether the heartlands can supplant Silicon Valley.

(Joel Beasley at 00:04:46) Oh, that's his Rise of the Rest tour, or I can't remember the name.

(Steven Levy at 00:04:49) Yeah, yep. He did a bus tour and I thought, how weird for a billionaire, riding a bus.

(Joel Beasley at 00:04:55) Warren Buffett, you can find him in a McDonald's parking lot, so...

(Steven Levy at 00:04:58) Yeah, that's true. You find him at, well, Dairy Queen, DQ. He's the DQ guy because he's got money in it.

(Joel Beasley at 00:05:05) Yeah. So how did you... Have you ever got to meet Warren Buffett, by the way?

(Steven Levy at 00:05:08) Yeah, I did. I met him when I took a job at Newsweek in the mid-nineties, and Buffett was on the Washington Post board at the time. Washington Post owned Newsweek at the time. So as a new employee covering this exciting area, sometimes for the board meetings they would bring up a couple of journalists. Once a year they did a board meeting at the Newsweek offices, so I went up and met him there. And I interviewed him a few times while covering Bill Gates. And he was friends with Kay Graham, who was the publisher at the time, the owner at the time of the Washington Post organization. So I met him several times. Fascinating guy.

(Joel Beasley at 00:05:51) About how many of these interesting people do you meet become people that are in your life forever and you communicate with them regularly?

(Steven Levy at 00:06:01) Ratio is probably pretty low because I talk to a lot of people, but there's a bunch of them. Yeah. You know, like Bill Gates, I've been interviewing since the early eighties. And before he died, Steve Jobs, I interviewed many, many times. It was a professional relationship. It was a relationship. I went to his memorial service. Other people sometimes become actually friends that you kind of hang out with all the time. The day that I first saw the Macintosh, I was covering it for Rolling Stone. I got in before the Macintosh launched, so this was late 1983. That day I met not only Steve Jobs, but the people who did the Macintosh, the Macintosh team. Guys like Andy Hertzfeld, the great hacker, Bill Atkinson, Susan Kare, the artist, Joanna Hoffman, who was the marketing person. And those people, we hit it off and they became my friends ever since. We watched our kids grow up together.

(Joel Beasley at 00:07:00) Oh yeah. The reason why I was asking is selfishly, so I've done I think 530 interviews, and I'd say maybe one out of 50, I end up... they become a part of my life and we text each other pictures of our kids and things like that. So that's why I was curious because you've met so many people.

(Steven Levy at 00:07:17) Yeah. Usually for every book there's a couple of people who you wind up getting a connection with. You know, I did a book about Google, and I connected with this guy who was one of the VPs, Bradley Horowitz, and we became good friends. I just went to his wife's birthday party.

(Joel Beasley at 00:07:36) And what was the Google book about?

(Steven Levy at 00:07:38) It was called In the Plex. It was what I tried to do is the definitive story of Google up to the minute where Eric Schmidt resigned and Larry Page took over again. And I tried to nail what made Google Google and spent endless time there, talked to hundreds of people, and spent time in China. A big part of the book was about Google's China experiment because to me that was sort of the moral test of Google at the time.

(Joel Beasley at 00:08:10) And so what's the one big takeaway from that book?

(Steven Levy at 00:08:15) Well, it's the struggle to have these incredibly innovative founders who put a stake in the ground. They said, "We are not a conventional company." And the struggle of becoming a giant company while being rebels, while being disruptors, right? At the time I published the book in 2011, they were still in that game. I'd say another decade later, Google is by many accounts a much more conventional company. The founders aren't there anymore. The guy running it is a terrific guy, super smart guy, but he isn't out on the edge the way Larry and Sergey were.

(Joel Beasley at 00:09:02) Yeah, absolutely. I mean, for me, I have my personal investment philosophy is I focus on companies where the founders are actively involved in the company, because I've seen what happens when they leave and then a board takes over, a private equity firm. It's just not the same.

(Steven Levy at 00:09:17) How's your Meta investment doing?

(Joel Beasley at 00:09:21) Oh, can you text Mark for me? So how did that project even come up, the Facebook project?

(Steven Levy at 00:09:29) So I've been covering Facebook since pretty early on. I met Mark in 2006, or early in 2006, and wrote a Newsweek cover about them the year afterwards, and wrote a lot about it when I went to WIRED in 2008. And didn't think I'd write a book. But then one day, I think it was 2015, the end of the summer, Mark posted that a billion people had been on Facebook, that platform, in the past twenty-four hours. Right? Not just monthly users, but a billion people that day. And I thought, that has never happened in all of human history, to have such a huge percentage of humanity in this network where anyone could communicate with anyone else. It was something I felt I had to write this book. So then I really wanted to get deep cooperation. So it took me a year to get all those ducks in line. And literally a year to the day after Mark made that post, I was on a plane to Nigeria to see Mark go to Africa for the first time and begin the research on that book. And I interviewed him nine times during the course of the book.

(Joel Beasley at 00:10:48) What's he like?

(Steven Levy at 00:10:49) You know, in some ways, what you see is what you get. He is... I think he wants to make interviews work, but he's kind of literal. He does have a sense of humor, but it's super dry. You really have to spend time with him before he gets loose enough to share more things. Right? He's very defensive. You could see in the people who are at the top of the hierarchy at Meta, which is the name for what used to be Facebook, there's people who have been there for almost twenty years now. He has to know you really well to trust you. And he really values people who stick around, and some of those people... a lot of people left, but the ones... Chris Cox is the head of product, Andrew Bosworth, Boz, who joined the company in 2005, I think. Naomi Gleit, other people from 2007, 2008. Those are the people who are helping him run the company... who we really know... it's like a country... who he really knows and trusts.

(Joel Beasley at 00:12:02) It's bigger than some countries.

(Steven Levy at 00:12:03) Well, it is. Yeah. It's a little smaller than it used to be in terms of market cap, but it is a giant country in terms of population. Yeah. It's probably... there's more population on Meta than any country in the world. There's no country that has 3 billion people.

(Joel Beasley at 00:12:23) Yeah, absolutely. And financially, I'm sure it's bigger than some of those small countries. The world's a very, very big place. I don't want to cover all the points in the book because people need to go buy the book, right? And what's the title so we can direct people now?

(Steven Levy at 00:12:34) It's called Facebook: The Inside Story.

(Joel Beasley at 00:12:37) Excellent. And then what was the... the one thing that caught my eye from it was there was something that Mark originally initially intended for it to be, and then there's what actually came about. What's the difference? What was he originally intending for it, and what did it become?

(Steven Levy at 00:12:55) So the idea was, and the mission statement was, to connect the world. When Mark started it, he was connecting Harvard and then went to colleges, right? He portrays it as saying, "Oh, he just did this thing in the dorm room and thought, how would it work at Harvard?" But he was ambitious. Before the month was out where he launched Facebook, and it was February, the shortest month, he launched it at Columbia and sort of took over other campuses. He's a big Risk fan. So he looked at the college campuses around the U.S. and later the world like a Risk game where you'd move into one, and sometimes there'd be competition and you'd knock off that person. And then, weirdly, the first campus besides Harvard where he started it was Columbia, which actually had a competitor on board. And he felt, "Let me take on this college where there's somebody already operating this sort of connecting, Facebook-like system, this network. And if I could knock them off, then I'll be even stronger as I go from campus to campus and take over the world." He went to Silicon Valley after a few months for the first summer of Facebook and met up with people who were very used to blitzscaling, as Reid Hoffman, the founder of LinkedIn, says. Hoffman was an early investor and had this ambition of, "Maybe we should connect everyone in the world." But he was just thinking of people connecting with each other in a network, sharing your personal information, your personal experiences kind of way. It wasn't thinking of it as an entertainment medium where influencers or people with funny videos or whatever would get hundreds of thousands or millions of views. But when they determined that that could happen, a process began where it became less and less of your friends and family and connections, and more and more, "Let's hold these people here, keep their attention, get their information so we could sell personalized ads to them." And that sort of drove what the company was and what the platform was until it is what it is now, where the company is focusing on TikTok-like little videos, which really have nothing to do with... your grandmother's not making a TikTok video.

(Joel Beasley at 00:15:39) Speak for yourself. No, I just actually... I did an interview with the head of technology for the United States for TikTok, and I hadn't actually used TikTok. And when preparing for that interview, I had my team show me what TikTok is, and we did a group call right here in this office. And I put my phone up. They showed me how to get involved and everything, and I got it. But I'll tell you what, boy, did that thing give me a headache. You know, I'm on Instagram and I read online. I subscribe to a couple different journalists I enjoy, but just the quickness of the videos, and it just was... it was not my... it's just not my thing.

(Steven Levy at 00:16:20) Really? Yeah. So you didn't get sucked in? You didn't go down the rabbit hole?

(Joel Beasley at 00:16:23) No. In fact, I spent three separate sessions trying to get into it. I was trying to teach the algorithm what I was interested in so it would give me stuff that I would like, and I just couldn't get into it. Now YouTube Shorts, however, they typically last about a minute or so, and that's really good. And I think it's so good because it's known me for twenty years, right? Versus TikTok knows me from the moment I register. So they were really good at being able to serve me content that I would like.

(Steven Levy at 00:16:54) It's interesting. I find, you know, TikTok, you could look at it intending to spend maybe a couple of minutes waiting in line, and then after you're in line, I find you're still looking. It's a time sink that I try not to fire it up too much because half an hour is burned away in a second.

(Joel Beasley at 00:17:14) Oh yeah. What's your favorite social media platform?

(Steven Levy at 00:17:17) Well, I like Instagram a lot these days because my son is a photographer and he posts a lot on it.

(Joel Beasley at 00:17:23) Oh, nice. You have grandkids on there too?

(Steven Levy at 00:17:25) No, no, no. I have one kid, and he hasn't spawned yet.

(Joel Beasley at 00:17:30) Yeah. I just had my third last week.

(Steven Levy at 00:17:34) Really? Oh yeah. Congratulations.

(Joel Beasley at 00:17:36) Thank you. Thank you. It's crazy. But I want to talk a little bit about this whole podcasting thing because you've been around professionally since before the internet got popular, and you watched it. For context, I'm 34.

(Joel Beasley at 00:17:51) So some of my earlier memories of the internet were the free CDs being everywhere at the grocery store. They'd put these free AOL CDs everywhere. When you saw podcasting start to come up, what were your first thoughts?

(Steven Levy at 00:18:05) So, you know, I wrote a book about the iPod. It was called The Perfect Thing. And the thing I loved about the iPod was how you could take your music collection and shuffle it. Right? And it'd be like your own radio station.

(Steven Levy at 00:18:21) So I liked the shuffle function so much that I wrote the book like a series of essays that you could shuffle. And we did four different versions of it, determined by picking ping pong balls, you know, kind of out of a paper bag. And, you know, the introduction was the same, but things were in different orders. I actually did four different versions of it.

(Steven Levy at 00:18:43) And one chapter was about podcasting, because that's where, you know, the pod and podcasting is named after the iPod. So it started off with this thing is delivered by RSS. Right? And it was very much out of the blogging community. And interestingly, the guy who did Blogger, Evan Williams, started a company called Odeo, which was going to be a podcasting company. But when Apple announced its podcasting app, he realized he was going to get snowed under. So he shifted the company to an idea that one of his engineers came up with called Twitter. So that was the evolution of that. And I always thought it was a great digital play on radio. Right? Radio, no one ever had like a VCR for radio. Right? People didn't tape radio shows and keep them, but podcasting allowed you to asynchronously listen in on an interview like this, which is super valuable because, you know, all this great stuff happened on the radio that you actually literally had to be there to consume. And of course, because these interviews were going to be accessible, more people would submit to being interviewed, and more creative people got in the interview business, you know, like you and other favorite podcast interviewers. So I'm actually super impressed at how that field has taken off and built to what it is today. I still think that we're waiting for the greatest podcast app. I haven't seen that. I'm not satisfied, certainly not with Apple's podcasting app or the ones from the streaming services. So I think that's, you know, I'm waiting for someone to crack the code of that.

(Joel Beasley at 00:20:34) Me too. And I've seen Spotify has definitely taken a huge market share in the past two years, because we've been doing this for five years. And, you know, we look at our stats all the time, and it tells us which player people are listening through to the best of its ability. And we've just seen Spotify crank up.

(Steven Levy at 00:20:51) Right. Well, I guess then the question is when these platforms take over, so then it becomes a discovery issue. Right? So they have, also a company like Spotify, they bought these companies. Right? So some of the content is content they own, like Joe Rogan or whatever. And the question is, if I'm putting a podcast up on Spotify, how can I get attention when they have their own stuff up top? Right? You know, this is an issue that you were seeing all over tech when you have these platforms, some of which the content is theirs, other content people promote from advertising. So if you don't have a lot of money to advertise, and you're not owned by the platform, how do you get the steam to bring in the users? There's nothing like a neutral search engine to find what you want.

(Joel Beasley at 00:21:45) Just relentless work and bringing as much value as you possibly can to the audience. Right?

(Steven Levy at 00:21:50) Right. Well, you know, if you've cracked that, that's great because it really is a terrific hump to get over to get the initial audience, then maybe you'll get word of mouth and people, you know, sharing, hey, here's a great podcast.

(Joel Beasley at 00:22:05) We market this thing like crazy too. So we'll take a clip of you saying something interesting, and we'll show it to people. We'll micro target on the different platforms to people who are interested in books and technology, so that when they see you, they're like, you know, you're connected to their interest, and then there'll be a link to continue listening to the rest of the show. And so—

(Steven Levy at 00:22:27) Do you do paid advertising?

(Joel Beasley at 00:22:28) Yeah. So the evolution of this, I'll give you the 60-second backstory. Right? Software engineer for 17 years, built systems, sold them. So I'd build small teams or teams of teams and do that. Had some success in real estate software. My mom passed away, and I got to be there in the room. And that was a huge defining moment for me because it made me realize how finite life is. And so I had this idea to write this book about sharing my knowledge, and I had it for years. And so I made that the decision. I was like, I'm going to write that book now. So I immediately started working on it. It took me about a year, and it was called Modern CTO. And it was simply saying, hey, I don't know everything, but here is what I did, and here's my experience, and here's the issues I learned along the way, and, you know, write me if I'm wrong. And before I put it out, I didn't want to get flamed, you know, on the internet or yelled at. So I started sending copies of it to other CTOs, and I said, hey, can we jump on a call? And that turned into the podcast. Two years, it was just like an expensive hobby. In year three, we were so booked up. Like, we were booked up six months in advance. And a company—I can't remember who was our first customer—but they came to us and they said, we can't wait six months. We have a product launch, and we need to get it out to your audience now. And I was like, all right, well, if you pay the production cost, I'll get another producer, and I'll have them come in and I'll have them produce up the episode and all the content and deliverables and all that. And they're like, yeah, we have a budget for that. I go, really? They're like, yeah. I was like, well, how much are your budgets for that? So for me, I was doing it because I wanted to meet interesting people and talk to people about the area that I spent most of my career in. And I was hoping that it would land me VP of engineering at Uber or something cool through relationships. I didn't expect this to become the business. And then we started making podcasts for other companies, and that grew the business even farther. So it's been a pleasant surprise, but I'm no longer writing software anymore.

(Steven Levy at 00:24:28) Well, congratulations. No, that's great. You know? Because that shows—look, I never thought I'd be writing about technology. When I went to college in the late '60s, early '70s, you know, we thought the computers were part of the war machine. They were dehumanizing people, right? And when I started meeting the hackers, I realized that it was the opposite. These people were using it to augment what's creative about humans. You know, the narrative of the industry I cover has changed. You know, some of that optimism proved to be, let's say, overhyped, and we didn't see the dark side of it. You know, certainly those days were exciting. You know, when I was in college, I idolized Rolling Stone. I thought, you know, that what was happening in music was more exciting than anything. I thought maybe I'll be a rock critic. But by the time I became a journalist in the mid-'70s, even though I started writing about music, I didn't feel that it was at the center of the culture anymore. You know, not like it was in the late '60s when Jimi Hendrix was playing and, you know, Dylan was doing his stuff and, you know, the music was really changing the culture. But in the early '80s, I sensed the computers were doing that. And that was the exciting thing. So even though I wound up writing for Rolling Stone in the 1980s, it wasn't until the early '90s when I joined, started writing—I wasn't working full time then, but started writing for Wired, which was going to be the Rolling Stone of technology—did that connect. And I realized that, you know, I was on the equivalent of the Led Zeppelin plane in the culture by writing about Steve Jobs and Bill Gates and AI and things like that.

(Joel Beasley at 00:26:19) Oh, yeah. Wired is the brand. Right? It's the highest value tech publication brand that I can think. And there's definitely more modern ones, but there's that aspect of trust where you've been watching the brand since the moment you started.

(Steven Levy at 00:26:35) Yeah.

(Joel Beasley at 00:26:35) And I think that's valuable.

(Steven Levy at 00:26:37) Yeah. Yeah. When Kevin Kelly, who was the first executive editor, asked me, he said, I'd like you to write, you know, this story for us. Yeah, it'll be the cover of the second issue. And I thought for a minute, I'd think, gee, you know, I wonder if I'm going to get my expenses back because I'm not sure there's going to be a second issue.

(Joel Beasley at 00:26:56) That's funny.

(Steven Levy at 00:26:58) Little did I know that I'd be writing for Wired when we're about to celebrate our 30th anniversary.

(Joel Beasley at 00:27:03) And what is your title? I read it. It's editor at large.

(Steven Levy at 00:27:06) I'm an editor—I'm just a writer, but I am at large. I'll write about anything. Right?

(Joel Beasley at 00:27:11) That's what at large means?

(Steven Levy at 00:27:15) Yeah.

(Joel Beasley at 00:27:15) Oh, okay. Cool. See, I'm learning. And how has journalism changed? Because, obviously, that's something that sounds like 101 stuff that I didn't know and just learned. And I'm just a very curious person, so when I got into it, I just wanted to know information. I never claimed I was a journalist. And as things progressed, I needed it to stay more interesting for me, so I started venturing out into different technologies and questions like that. I wouldn't say I consider myself a journalist because I think that I haven't put in my time, educationally to be to have that title. But how has journalism itself changed from when you started in the '70s to today?

(Steven Levy at 00:27:55) Oh, dramatically. I mean, I think that—I mean, basically, what a journalist does, what a writer does, you know, can you do this in your podcast? You know, you research your guest. Right? And you figure out, driven by your own curiosity, because you are the stand-in for the listener. You know, okay, and when you're writing, you're the stand-in for the reader. What do people want to hear? Right? What is the story? Right? So kind of talking to people, looking at research materials, going on site and seeing for yourself. These are the tools of journalism that are involved in the story, but everything else around it has changed. The distribution method, the headlines, you know, for in the early part of my career, forget the tools I use to produce a story, but 100%, everything you wrote was within the covers of a magazine or a newspaper. Right? And the only people who read it were people who plunked down their quarters to read that hunk of paper, right, which they turn the page and they'd read it. Right? And you weren't concerned about the numbers, you know, the publisher would figure out how many copies to print, but who read it among the buyers, you'd never know. And that wasn't really something you thought about. Obviously, some pieces were more popular than others, but other pieces were just important to be there. And when you had a headline for a story, the assumption was the headline might draw you into the story that was right underneath it. Right? You know, you didn't have to explain yourself. So you think about a headline now, and stories now exist in isolation. You know, people don't—when they're online, they don't necessarily read the whole package. People don't go online and say, wow, even though you're a subscriber to Wired, you don't sit there and go to the Wired website and read one story, the next story, the next story, the next story. You know, you'll get a clue to that or maybe you'll go to the homepage and see something and then come back a couple days later and see something else. Maybe you'll even have an alert for a writer, you know, that you like. But, you know, there's many people encounter the stories in isolation. They'll say, oh, here's an interesting story. And you'll be drawn in by a headline, which sort of has to explain itself. So I took a couple of years off from Wired in 2014 and joined Medium, you know, founded by Evan Williams, the guy I mentioned earlier that did Odeo and Twitter. And I started a publication called Backchannel. And we basically did a story a day. And I learned that certain stories, which could be great in the context of a publication, like a really interesting thought piece, an essay. Right? It was really tough for us to put across if we were just doing one story a day because each story had to claw its way into people's attention. Right? So, I mean, I remember I tried to find some of the best young writers who I could find. One was a writer, woman named Casey Newton, fantastic writer. But, you know, the thoughtful pieces she wrote didn't fit for us. Right? Now she's a great writer for The Verge. Right? You know, where she's a natural fit and she works within the context of that. She wrote a wonderful book about the aftereffects of To Kill a Mockingbird, right? Harper Lee. So it changes the content, what content gets rewarded in a certain case. There's certain kinds of stories that once you could do in the context of this publication that you purchased, they probably aren't going to get as much attention now. So suddenly the content changes of journalism. And, you know, if you're going to fund expensive investigative reporting, you have to have almost a different kind of business plan to go because you might spend six months on a story and you release it. And, you know, the same day you'll release a story that was written in two hours, you know, based on something whimsical. And that two-hour story might draw more than the solid investigative, painstaking work you did to expose a scandal.

(Joel Beasley at 00:32:32) Yeah. It's a super strange thing that's happened. Do you think that there's a way out?

(Steven Levy at 00:32:37) You know, there's publications like Wired and The New Yorker and The New York Times, you know, I've sort of figured out a way to deliver that in-depth journalism and build an audience that wants to see it. Right? You know, you can't, you know, there's still an argument for buying into the whole package.

(Joel Beasley at 00:32:58) Yes. Well, me personally, I like long-form content.

(Steven Levy at 00:33:02) Yeah. Well, that's my heart, you know, and that's what I love to do. And I love that you could do it in Wired, and sometimes it'll be in print and sometimes, you know, sometimes not. But, you know, I could still write these 7,000-word stories that take months to do and travel for it and, you know, deliver something that is worth reading that day and a year later.

(Joel Beasley at 00:33:28) What writers are you reading in technology?

(Steven Levy at 00:33:32) You know, there's a great book behind me. John Markoff, who's a terrific writer for the New York Times for a long time, just published a book about Stewart Brand, who was a pioneer in a lot of things, called Whole Earth, behind me here. That was great. I think Taylor Lorenz, who writes for the Washington Post, created this influencer beat, and she's very good. Lauren Goode is a colleague at Wired, does fantastic work, and she's been writing some great features as well as doing gear stuff. So the field is just brimming with great writers. And, you know, my former colleague at Newsweek, Brad Stone, has written wonderful things about Amazon.

(Joel Beasley at 00:34:13) Is there any books about how to interview people well that aren't, not like job interviews, like journalistic interviews?

(Steven Levy at 00:34:23) You know, that's a great question. It just so happens, Wired, we do this thing called Skillshare, where we do internal presentations for the staff to share our techniques and things like that. So I'm literally doing one on interviewing.

(Joel Beasley at 00:34:39) I went to search for a book on this because after the podcast started making money, I thought, well, I need to put some of that money behind my education, learn how to become a better podcast host. And I went to search, and I found tons of books about how to interview, like job interviews that dominate the search results when you start searching for this type of book. And then I was looking for radio host interviews or different types of interviews. The closest thing I found was a very short mention about it in one of Howard Stern's books.

(Steven Levy at 00:35:09) Well, he's a master interviewer. You know? I mean, some of the great interviewers, Howard Stern, Marc Maron. You know, it's interesting. Joe Rogan is, you know, he's been criticized a lot. I've been critical of some stuff he's done.

(Steven Levy at 00:35:23) But I think he's a very good interviewer because he draws out what he's curious about. But you're right. I don't know. I can't think of any great book. You know, I saw on the plane the other day, they had some MasterClass things just in the seat of the plane ahead of me.

(Steven Levy at 00:35:40) And Malcolm Gladwell did a segment in his thing about interviewing. And a couple of things that he said were things that I had already written down that I was going to share with Wired. And one of them is, you know, just don't be afraid to ask dumb questions. Right? You know, and don't pretend. The biggest sin you could do in interviewing, there's a few of them, but one is to pretend you know something when you don't.

(Steven Levy at 00:36:04) Right? If someone gives an abbreviation and you figure, well, I don't want to look dumb. I'm not going to ask what that means. Or uses, you know, refers to something that the person seems to think you should know. If you don't know it, just say, what is that? Because chances are your listener might not know it either, right?

(Steven Levy at 00:36:24) And the other thing is, and you know, I think you do this already, I could tell, is just to ask, what do people really want to hear? Right? And to be direct. And sometimes if it's an embarrassing question, I find the best thing to do is ask it directly. Don't get all mealy-mouthed and say, well, gee, you know, my editor says I should ask this or, you know, or some people say that. Just ask directly, you know. I mean, in the Steve Case interview, one thing that I wanted to ask him about was he, you know, he has this fund that he started a few years ago, a $150 million fund to invest in these companies. And the guy he picked to run the fund was JD Vance.

(Steven Levy at 00:37:07) He had just written the Hillbilly Elegy and was a hot commodity, and was known as a person who brings people together. That's what Steve really wanted. Steve is very much into bringing all sides together, you know, people not being polarized. And I said to Steve, I said, listen, you know, you picked this guy to do this, but I looked at the index of your book, you don't mention the guy once. Yeah.

(Steven Levy at 00:37:34) Did he turn out to be something that you felt, you know, he wasn't when you picked him? And, you know, he gave me an answer and then I went back to him and I said, well, wait a minute. You know, do you think he snookered you? And that was what I was thinking. I didn't want to put it in any other more delicate way.

(Steven Levy at 00:37:50) And, you know, he said, well, I don't know if I'd use that word, but, you know, but just asking things directly. You know, I also asked him and said, what were the returns on the fund? What, you know? He didn't share the number, but ask directly.

(Joel Beasley at 00:38:02) Yeah. I think that is fantastic advice. I wish I would have heard earlier. But, yeah, I found that people are not shy to share their assessment of you as an interviewer. So going around and getting to do, well, once the podcast started to get popular, I started to get invited to conferences, and I'd go give a talk, and then people would come up to me after and share different things.

(Joel Beasley at 00:38:28) And so I would sort of figure out things that I was doing that people liked or, yeah, or whatnot. And, ultimately, what it came down to was just being super self-aware of who I am and just being that person because I just happened, I didn't choose this genetically, I'm a curious person.

(Joel Beasley at 00:38:46) And so as long as I'm asking questions and then making sure that I am thinking about what is the audience wanting to hear about? What's the next thing that they should hear about? Because sometimes I'll get excited with the next question I want to know about, and I have to remind myself, okay, we need to make sure we finish this line because it's somewhat hard to go back to a line of questioning.

(Steven Levy at 00:39:09) Well, also, I mean, it's important, you know, to both prepare and have a lot of questions you want to ask, but also to listen. Because, you know, during the course of an interview, the subject is probably going to say something which you haven't thought of, and is a really interesting path to follow. So, you know, you can't just be thinking, you know, about your next question. But, you know, and this is particularly important in podcasts like you do or interviews on stage, which I've done a number of them. Like, I've interviewed, you know, Jeff Bezos and Sundar Pichai and just any number of people on stage.

(Steven Levy at 00:39:51) And a podcast is like that. When you interview someone, you know, just your tape recorder for a story, you know, you could just jump anywhere and you could bumble and, you know, it really doesn't matter. But when you're doing this where people are going to hear the conversation, you know, it's important to listen to pick up because quite often, your subject's going to say something that you want to follow. I've interviewed Bill Gates a lot of times. And quite often, he'll say something that, you know, that sort of opens up a really interesting path.

(Steven Levy at 00:40:23) And so you don't want to fall into a trap where you say, well, I've only got a half an hour with Bill Gates. I want to hit these points. Right? So I'm thinking, you know, when's the next question? So this will be going on about something.

(Steven Levy at 00:40:37) And, you know, the question is, what, why is he talking about this so much? What is it about that that compels him? And then you kind of zero in on that. And I find some of the best questions you ask are either tell me more or why.

(Joel Beasley at 00:40:52) And I think that it would be great if you were to record it and publish it or maybe send it to me privately or something.

(Steven Levy at 00:41:02) With Gates, I always try to ask him a question that he's never been asked before in every interview.

(Joel Beasley at 00:41:08) Oh, okay. That's a good one.

(Steven Levy at 00:41:10) You know, I, like, for instance, once I saw in his website, he mentioned a lot of books he's read and, you know, one was Catcher in the Rye. So I asked him if he identified with Holden Caulfield. What did he say? Well, he had a great answer. He said, well, I'm not quite like Holden, but I'd love to see the ducks at Central Park.

(Steven Levy at 00:41:34) And I mean, he had totally a great recall of the book, and we riffed on that for a couple of minutes. It was really interesting.

(Joel Beasley at 00:41:44) Most memorable interview you've done?

(Steven Levy at 00:41:46) Well, actually, before I interviewed Bob Marley. Nice. And that was unbelievable. My first Steve Jobs interview was great. It was, you know, when the Macintosh was coming out, you know, and he just hit me with the force of this personality that was great.

(Steven Levy at 00:42:04) You know, sometimes when you're interviewing someone, I love it when you're interviewing someone about something important and maybe the person has not been interviewed a lot before. So some of the early hackers I interviewed from MIT, those were super exciting because I realized when I was doing the book that this was the birth of computer culture. It all started there. The Mesopotamia of computer culture was in, you know, Building 26 at MIT with the Model Railroad Club and then the AI lab.

(Steven Levy at 00:42:39) And these guys had never talked to a journalist before. It was kind of like going down, you know, like the river and finding this tribe that, you know, hadn't been contacted before. They were wary of talking to a journalist on one hand, but on the other hand, they were open, you know, they felt, well, I guess someone should tell the story even though this guy doesn't seem too technical or whatever, but he's asking me. And, you know, it was just fascinating as they unfolded the story, which turned out to be so significant.

(Joel Beasley at 00:43:11) Final question as we wrap up. You inspired me to ask you a question that you've never been asked before, so here it goes. You finish your interview today. AC is all working good. You decide to go for a drive.

(Joel Beasley at 00:43:23) You get in your car. You're driving down the street, and you're at a stoplight. And pulls up next to you, rolls down his window, it's Elon Musk. Okay? He's right next to you at the stoplight. He's like, hey, Steven. Come check out my new helicopter. And so you go to his house, and he's got the helicopter, and he shows it to you. And then he says, I want to show you something else as well. And he's got a time machine behind the curtain.

(Joel Beasley at 00:43:46) And the way this time machine works is you get to go back. It's specifically 100% dialed into the moment after your Bob Marley interview. Okay? And you get to tell yourself something for 30 seconds, get 30 seconds of advice to talk to yourself in that moment of time, then that'll help you for the rest of your life. What would you tell your past self?

(Steven Levy at 00:44:07) Make an extra copy of the tape.

(Joel Beasley at 00:44:12) Did you lose your Bob Marley interview?

(Steven Levy at 00:44:14) Didn't lose it, but my battery was low. And when I played it back, it was like...

(Joel Beasley at 00:44:24) Oh, man. Were you able to publish the interview and get it all taken care of?

(Steven Levy at 00:44:29) I did write the story. Yeah. Yeah.

(Joel Beasley at 00:44:30) Okay.

(Steven Levy at 00:44:31) I hand-transcribed it. You know? But I actually, I can't, I have, and if I had an extra copy, I know where the tape is. I know we didn't throw it out, but if I had it now, if I ever find it, I could, you know, put it up in audio software and speed it up.

(Joel Beasley at 00:44:50) There you go. Well, this has been fascinating, Steven. I really appreciate you coming and hanging out with us. So tell me about your newsletter.

(Steven Levy at 00:44:58) I do a newsletter every week. It's for subscribers only. It's called Plaintext. If you go through the link, you can get a year of Wired, including my newsletter, the print version, and unlimited web for $5 if you follow this link.

(Joel Beasley at 00:45:13) Send it to me. I'll be your next subscriber, my friend. And we made a podcast. How do you feel?

(Steven Levy at 00:45:19) My pleasure, Joel.

(Joel Beasley at 00:45:19) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn or send me an email, [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.