Lily Hay Newman is a senior writer at WIRED focused on information security, digital privacy, and hacking. She previously worked as a technology reporter at Slate magazine and was the staff writer for Future Tense, a publication and project of Slate, the New America Foundation, and Arizona State University. Additionally her work has appeared in Gizmodo, Fast Company, IEEE Spectrum, and Popular Mechanics. She lives in New York City. In this episode we dig deep into Lily's journey, Security in Open Source, and the finer things in life like our favorite NY pizza joints by the slice! Truly a pleasure to speak to Lily!
Lily Hay Newman is a senior writer at WIRED focused on information security, digital privacy, and hacking. She previously worked as a technology reporter at Slate magazine and was the staff writer for Future Tense, a publication and project of Slate, the New America Foundation, and Arizona State University. Additionally her work has appeared in Gizmodo, Fast Company, IEEE Spectrum, and Popular Mechanics. She lives in New York City.
In this episode we dig deep into Lily's journey, Security in Open Source, and the finer things in life like our favorite NY pizza joints by the slice! Truly a pleasure to speak to Lily!
Timeline Topics
00:00 - Opener/Sponsors
00:14 - Intro to Lily Hey Newman from Wired Magazine
00:28 - Lily's Journey
07:01 - the Overall process of writing a tech article
11:37 - Pitches that get picked up.... or didnt.
13:55 - Writers block and how do you get out of it.
16:34 - Writing for Information Security
21:58 - Sources - what makes for a good source?
23:32 - Is Open Source the future of Security?
27:13 - What would Lily write if she didn't write for Infosec
29:40 - NY Pizza Slice discussion.
30:28 - What work is Lily most proud of.
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- [Narrator] This episode of "The Popcast" is brought to you by these sponsors.
- Hello everyone, and welcome to "The Popcast." I have a special treat for you today. She's a senior writer at "Wired" focused on information security, digital privacy, and hacking. Welcome to "The Popcast," Lily Hay Newman.
- It's a pleasure to be here.
- Excited to have you. So I was like, look, you know, like writing for technologies, is really protecting general security, is just a, it's a harrowing experience. It's tough because you have to like embody the audience, you have to embodied the, you know, the technologies and all of that. But I want to talk about your overall journey. You know, how'd you get started in this path?
- I got started in this path because I have always been really interested in the evolution of technology, but I also could always tell that writing was my strongest skill, you know, and that was kind of my comfort zone. So, I think I wanted a way to meld those things rather than, you know, pursuing hard sciences or pursuing engineering or becoming a developer or something. I wanted to be able to really have my writing at the forefront or, yeah. So yeah, that, that was how it evolved. I, you know, took a lot of science courses, sort of like pre-med or something essentially in college. And I, was just looking for, well I could do technical writing, I could, you know, I was trying to figure it out. And then my college advisor said to me, "Well, I don't understand, aren't you "going to be a journalist? "You know, you're the Editor in Chief "of the school newspaper. "And you're."
- Can we go back? Let me, I'm sorry to interrupt you, but let's go back a little.
- Oh sure. So you're growing up in your writing and all that. Well, where'd you grow up if you don't mind me asking?
- I grew up in New York City.
- Okay. So you're surrounded by amazing writers and there's The New Yorker and there's all these things. When you're growing up, like when you a Highlights person, then you went right into The New Yorker? Talk to me about that progression. Let's talk about that.
- Okay, we wanna go like way, way back?
- Yeah.
- I think for me, I dunno, like what media was I consuming as a kid or something? I think, yeah, my parents definitely subscribed to The New Yorker. And, you know, to your example, and a lot of like, you know, newspapers and magazines and I would read those. But I think also growing up in the city, I also just really tried to take advantage of like student tickets for music. I was really a big band nerd. Really into playing clarinet and saxophone. And so I would go to jazz. I would go to classical music, opera. And I just, even as a kid, I really valued the access to that stuff. And yeah, I think, but I think I am just such a, my brain is like a really words brain. And so I think, you know, it's just all always tied in to writing for me. Yeah.
- And where are you familiar at an earlier age at, like for in Wired or like, you know, kind of like when did you first get exposed to like Wired itself?
- I definitely read Wired a little bit, but mostly like in a doctor's offices or, you know, something like that. I don't know. Maybe that's weird to say, but I didn't have, I don't want to lie and say I had a subscription as a kid because I didn't. But I, one of my, I think one of the things that got me into tech reporting was really science reporting. This is probably a good way to say it. Like I was always really into, Nova and Nature and, you know, reading the science section in The Times on Tuesdays in The New York Times. And I remember, you know, in, I think 1995 when the Galileo probe, you know, was taking photos of Mars. And so it was always really interested in that stuff. And so I think it was really science journalism that got me interested in tech journalism. Because it's, and that's what got me interested in security reporting is it's the same concepts, right? Same idea.
- That to me, and again, I read some of your articles because I was introduced to you because of the SIC Store ceremony we did, right? And you did the article on it. And I was like, "This is very, very descriptive." And it's like, like you said, it's almost like a science paper. And that's what I think is so good about your, amazing about your writing is just that.
- Oh thanks. It's, it's very like, you know, detailed versus, "Hey, I'm just going to tell you about this event, "the people that are doing it." You're going back and you're giving that like slight history, that's to me is what a scientific mind does is going back and finding like the traces back to all that. So that, you know, I wasn't trying to like do this, like, you know, forensics on your writing style and all that. But I was just like, I kind of see that. That's why I asked that question about, you know, going back to what you read growing up. So let's go, now we'll flash forward. We're going to get into DeLorean. We're going to go back to college now.
- Cool.
- And so you're in college and you're like, "Okay, I want to be, you know." Your advisor said, what? And I'm sorry, I cut you off there. So.
- Oh no. He said, you know, I, he was like, I said, maybe I should do technical writing. Like what, you know, what types of, what should I think about doing after college? And he was just like, "I'm confused. "I thought you were going to be a journalist. "I don't understand." And I was like, "Oh yeah, no. "I obviously should do that." You know, like that is the way to meld, you know, my interest in, you know, evolving interests at that time in science and tech and engineering into, and meld it with my, you know, curiosity about people like, you know, interest in finding out more about the world, desire to, you know, hold power to account. Just like these sort of vague. I mean, I was in college, like not to overstate it, but, you know. And I was just sorta like, "Oh yeah, "you're right."
- Where'd you go to school? If you don't mind me asking?
- I went to Johns Hopkins in Baltimore.
- Got it. Crab cakes. Yum.
- Yes. Faidley's, shout out.
- No doubt. All right, so I want to talk to you about your overall process. Let's say we have an assignment in a month. Like talk to me about which, god, I'm being generous with a month, right? But like.
- Yeah, I was gonna say.
- Right, right? But like, let's go with like, "Hey, you know, "I got an assignment," and like, talk to me about your overall process.
- Well, first of all, I think at Wired, I feel really lucky to have a combination of assignments and stories that I pitch, right? And it's sort of this continuum. It's, I dunno, it's not to not give my editor credit for all of his brilliant ideas, but just sort of, I feel like there's a dialogue going on, you know, where it's less like, was it assigned or did I pitch it? And it's more like trying to figure out what we want to cover and need to cover, you know, to bring the readers the information we want to make sure they have. So I, you know, I think the process is sort of also related to whether it's related, whether the story is going to be connected to like a news situation that's actively playing out that's like a huge, you know, thing going on, which may be, is, you know, the Solar Winds hacking or a big ransomware attack, you know. Not that we have a lot of those going on right now or anything. You know, so it's like, is it a big story where we are trying to, you know, add reporting to it or, you know, analyze and explain a piece of it or go deep on, you know, like Wired loves to do wonky, explanatory aspects, you know, just carve out one part and, you know, explain only that that might be getting missed by other coverage. So is it something like that or is it a story where we are gonna, you know, bring a new story to the table. Or in, you know, new, so is it part of a bigger narrative or is it, you know, us starting that narrative or can, you know, contributing something new? So I, you know, I think that's a big part of the process. And then, from there I'm definitely a big, like, try to find the zone person. Like, you know, it's can be hard to find the writing zone. And you know, of course you're getting on calls, doing a lot of reporting, trying to figure out, you know, I try to think about, well, what are my questions? What are some questions that I would have if I hadn't been following something as closely? And, you know, getting the answers to all those questions and the story evolving as you know, I'm hearing what sources are saying. Sorry. Hearing what sources are saying. But then, also like trying to get to the point of like, "Okay, we know what the, I know what I'm going to write. "I need to wrangle it all into something "and go into the zone and, you know, "make it come out of me or something." Like to produce it. So it appears in the world and not just in my brain.
- Does it just materialize? Like sometimes you're like, you look down, it's like, "Oh, I was in a trance "and I come out of the trance." And it's, you know, like that? Is it almost like.
- Yeah. A lot of, for me, a lot of times, and then when I go back, you know, and look at, 'cause of course we always want to be back-linking in stories. Not to, I mean, also to promote our stories or whatever, but mainly, you know, so people have the past context and know our past coverage and can read back if they want to. But sometimes as I'm doing the back links, I'm like, "Whoa, I wrote that story?" And then I'm like, "Oh yeah, "I remember, but I was just so deep in the zone," you know. Like going back a few years or something. It's like certain stories, they, yeah. It's just like it materialized and you were in a trance the whole time.
- Civo was an alternative to the big hyperscale cloud providers. They've launched the world's first managed Kubernetes service powered exclusively by k3s. With sub-90 second cluster launch times, a simplified Kubernetes experience and predictable billing, Civo was on a mission to create a better developer experience. Get $250 free credit to get started. Sign up today at Civocloud.com/popcast. That's C- I- V- O- dot C- O- M- slash P- O- P- C- A- S- T-. Go check them out. Let me ask you this, has ever been like a pitch that you made and you were upset that it didn't get accepted because you were like, I mean, look, we all get, like, all of my episodes, I think are the greatest. They're like my children, right? Like just, you know how it is. Every piece you write, it's great. But like, has there been a situation when you were like, "This is such a good story and I, "this should've got picken up." Or conversely, one that got picked up, you're like, "I'm so proud of this one."
- Well, in terms of pitches that I, you know, wish had been picked up or something, I think the crucial thing about that is like, sure, sometimes it's frustrating, you know, if you pitch something and editors aren't like seeing what you're seeing. But I, at least to me, a huge concept in journalism is like, if your pitch isn't getting chosen, there's something not right. Like either you didn't do a good job pitching it, not to be negative, you know, either the pitch wasn't, you know, crafted correctly or, there's just something going on there, you know, because when something is clearly a great story, I think everybody recognizes that, you know? And so, sometimes I'll feel maybe frustrated with myself that I couldn't figure out, like if I have a lot of enthusiasm for something and I couldn't figure out how to convey that to others, that's like a failure of communication on my part, and so I'll be like, "Well, how can I get it across better?" You know, or how can I capture, you know, why I think it's important? But yeah, I try to, you know, I don't really, I don't feel like, I'm trying to think. I don't feel like I have a lot of like, you know, "They'll rue the day that they didn't accept "this pitch." Like things festering inside me.
- You know, like, again, this, part of the reason I wanted you on the show, 'cause I'm a fan of your writing, but also that I want folks that are technical people that are read your articles to understand this process. 'Cause well, none of us really understand, like you, you know, you have a window into the technologist world, right? We don't have a window into your world, right, to understand this, right? And so that's why.
- This is by design.
- Yeah, exactly. I wish I had this grand plan, you kidding me? I'm in my basement for god sakes. All right, so let's talk about writer's block. I mean, has like, what is your, you know, how do you get out of that writer's block, if you, you know?
- I think the pandemic is a good thing to talk about maybe because I did find, it was a lot harder. Some sometimes it was really into work because I was so happy that I, you know, had something I'm passionate about and that felt fulfilling, that I could do every day. And I also, you know, felt very grateful and appreciative that I had a job where I could work from home and, you know, just be collaborating with people I really enjoy working with every day, even if it was remote. So, you know, I think, that was great when it was flowing, but also the pandemic created a lot of times where I'm assuming it wasn't just me, like, you know, we all felt like, just harder to get motivated, harder to feel into anything. Even though I also feel lucky that, you know, I think, I dunno, I know some friends, all of whom have, you know, great jobs and whatever, but sometimes in certain industries, they struggled with feeling like, "What does this matter? "Like why does it really matter today?" And I felt very lucky that I always feel that, you know, my work is very purposeful and is contributing something tiny, you know, not trying to be arrogant here, but just like, you know, I always think I have the privilege of getting to feel like I'm trying to, you know, participate in human discourse or whatever. So that's, so that was great. But yeah, it was definitely, sometimes you just didn't feel the spark when you have not been out of your house in, you know, weeks or whatever, you know? So, I think I thought more about writer's block in the pandemic. I don't know. I don't have a lot of answers. Like, you know, I just try to, I think I will say I do draw a lot on how much I like working with my coworkers at Wired. It makes it fun. And so when you're, you know, just not really wanting to get a draft done, or you can just can't find the zone, like I was saying before, you just can't get in the zone. I think I lean a lot on like joking around with my colleagues to try to get back into it.
- Gotcha. So, you know, you work, you know, your writing is predominantly for like information security. And the information security community is wrapped a little tight, you know, because it's the high stakes. Okay, look you think about ransomware. It's very high stakes, right? Do you ever get that pressure to get it right? You know what I mean? Like, cause I'm on InfoSec, what I, you know, it's tough. Like I kind of want to understand like, hey, there's ever been somewhere where an article where someone was like, "No, this is incorrect." And you know, that kind of thing. You know?
- Well, I guess the way I feel is that the summit, okay. I don't know how to say it. Some of the pressure on Twitter or in like the discourse, I'm doing air quotes, of the InfoSec community. Like sometimes I think it can be unfair or, you know, people are being called out when they shouldn't be, or sometimes it can be a gender thing or it can be, you know, because someone's different in whatever way. And so that's obviously unacceptable and I like, I don't, it's the trends toward that sometimes I don't think are okay. But so not condoning that, but as a general thing, I think people being really rigorous and wanting reporting to be super, super accurate and true should align with what journalists are trying to do anyway. So again, they're like, I want to separate that sometimes I think there can be a bit of like a toxic discourse that is like, not, that's different and that, you know, but if we're sort of in just sort of pure, like if you're wrong, you get called out in a world that is fair and equitable, I think that is fine. And I, work so hard and sweat my stories so much to try to not have a situation where that would happen, you know? But it's not because I'm trying to like avoid getting called out, it's because the whole point of my job is to, you know, get stuff right and be accurate. And it's, you know, look what I've found is like you can't, you know, there can be, I sometimes have like, I spell someone's name wrong, or I get a, you know, like you can't be perfect all the time, but I've found that like the community overall again, you know, I think sometimes things can get kind of intense on social media, but with sources, like in, in my source relationships and in the feedback I get one-on-one and things like that, small mistakes, I haven't had a problem with on the, like, I try to keep it really rare occasion that they happen. So I think, more, I'm just like pretty motivated to try to not get stuff wrong as part of my craft or something.
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- Yes.
- What makes for a good source just for, and again, folks that are listening don't understand the whole vernacular of like, you know, journalism, and all that stuff.
- Oh, I mean, oh, it's like a huge topic. I think, you know, what makes a good source is, I think a shared vision about the importance in a democracy of disseminating information. You know, and sources can, they can only contribute what they can, you know, like it's, it doesn't mean one, you know, one source should be everything to all people and know all things. It's just like, if everyone contributes what they can, then we have a better understanding of what's going on in the world and things that aren't going right. You know, and, you know, shine a light on, problems that we, as a society need to address. So, you know, that's like super lofty. In practice, I think, yeah, good sources are just down to chat, you know? Like, you know, just to share their expertise.
- Awesome, awesome. So, I mean, you know, open source right now is this really hot topic, right? You know, and I live it, I've been living in it for the last, I don't know, five years, right? And so, you know, like, do you feel like open source is, you know, the future of security, like in terms of like, how do you feel about like, again, I'm not going to put you on a spot and say, "Okay, "I'm going to go back to this interview. "She said this," but like, you know what I mean? What do you think of open source and its impact on security?
- I think, okay. I think open source is great. I love open source, but I think, like it would go better if, like, I, there are struggles with capitalism and open source, right? Like it would be better if society could be kind of all in on open source, which is like, I mean, that just is not how anything works right now. So I think that, you know, makes it complicated. I just hear about so many great projects that are understaffed or people are volunteers. And what happens if someone is sick or has a kid, or, you know, whatever? Like, and so many of the problems in open source security come from like, well, there's a vulnerability and we don't have a point person, or this is no longer maintained. And everybody, you know, incorporated this, you know, code into their other things. And it's just everywhere. And, you know, it was written in the nineties. You know, like all these types of problems, which doesn't make me down on open source. It's just like, I just wish there was more person power available, you know, to realize an even greater potential of open source.
- And my thought on the security piece is like, you know, in responding to like external actors, to me is easier with open source. Meaning, you know, you don't like, if you think about the Solar Winds as an example, right? This was like a software supply chain hack and all the things that happening there versus like being an open source perspective, you wouldn't be able to kind of see things that were occurring, being able to address those things, to be able to, okay, this is happening. I can quickly patch this because you know, maybe the abundance of the world are saying, "Look, external actors, they're do doing it "from an another place. "We're seeing this. "Maybe we can address this by a rule set or, "you know, some type of patch roll, "that, those types of things." So, I mean, that's part and parcel why, you know, a lot of these projects are getting much more momentum now because it's seeing how you can react quickly to those things, so.
- Yeah. And I'm all for it. I mean, it's, you know, I think the momentum is great. I just feel like the economic incentives to do proprietary are still there. So it's like, it's just challenging. But again, I really want to emphasize, like big proponent, you know, it's not to be a downer. It's just like, I.
- You're talking about the reality of it. I mean, that's your job as a reporter, like to report the news, that's what you're doing here. So, that's great. That's awesome.
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- That's awesome. So I'm going to switch gears and ask this question. If you weren't writing for InfoSec, you know, and all that, what was, like you talked about science earlier, what would it be something that you'd want to like write for, from, there was another genre of some sort?
- I have always been really interested in like material science, things like battery science. I really like writing about, and this ties into security, but I really like, or sort of, I get my fix, for you know, in security the same way, but I really like writing about, you know, physics, math, stuff like that. Stuff that's really hard to write about. And that's very, meaning like, not like, "Oh, it's so hard, congratulations to me." Like where it's literally difficult to figure out what to say because there's so few like analogies to the real world that you can use and it's so abstract. I find that challenge really interesting. And I think it's very rewarding, you know, and I'm not an expert anyway, but when I can attempt to capture some of the nuance that experts are feeling an emotion about, like they're excited or they're scared, or they're confused, and they don't understand why their findings are this way. And you can try to capture some of the nuance of why for readers who are total lay people in that area. And, you know, couldn't really make much of the paper, and that's that's me too. You know, like I couldn't, wouldn't know all the drama and the stakes from just reading, you know, the technical write-ups. That is, yeah, what I find really interesting. And so that's fun in security too. But if I weren't writing about InfoSec, I would yeah. Want to write about still something kind of similar in that way.
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- Oh, wow. Okay, you're asking the like the serious questions.
- No more InfoSec crap. Let's go to the real right now.
- Talking about things that are going to be controversial and used against me decades later. All right. I'm going to say, slice, Sal & Carmine on Broadway and 100th, 101st.
- Nice. You been the Joe's on Bleaker?
- Yeah.
- Okay, all right.
- Joe's is good.
- We're going to grab a slice after this pandemic at some point. I'm telling, wait, are we done? Wait, we're still in it. Okay, well, we are gonna grab a slice. That's cool. All right, so here's my last question for you. What work are you most proud of?
- Yeah. You know, you were also talking about earlier, what is like a pitch that I'm very proud of? And I was sorta like, I sort of conveniently skirted around that and didn't answer that and only talked about like pitches that have not gotten chosen. And the reason was like, I'm very, I, you know, there are a lot of, there a lot of stories that I'm proud of. I hope that's, you know, good. And I hope all reporters feel that way. There are a lot of stories where I was like, where I'm like, "Yeah, I got that." You know, "I got it. "I captured it. "Or I figured it," you know, or like, "Somebody told me exactly what I needed "to know," or, you know, sometimes we say like, "The money quote," or whatever, you know, you got the perfect thing. But I think the thing that I'm most proud of and that I strive for the most and just to keep, you know, want to keep going, doing more and more is just covering big topics over time through incremental news coverage. Like, I think I'm proud that, you know, like we were talking about back linking in stories and linking back to previous coverage about the same topic so people can catch up. You know, I feel good when I do a bunch of back-linking in a story and I really have written a bunch of different things, you know, that are relevant to the new story and I'm going back and I'm like, "Yeah, that was interesting." And, you know, "Oh, you know, "people said very interesting stuff in this story "and it was a new, you know, spin on it." Or I remember I had never thought of it that way or, you know, so I think that's when I feel most fulfilled is when I feel like I have stayed on something over time and sorta like slowly peeled away the layers.
- Awesome. Well, Lily, we did it. Thank you so much for being on the Popcast.
- Yeah, thank you for having me and going on this journey into my history.
- It's been an awesome journey. Appreciate you. Thank you.