First Contact Transcript

Episode 17: Ev Williams on Coronavirus and the ‘Extreme’ Tech of the Future

First Contact with Laurie Segall is a Production of Dot Dot Dot Media and iHeart Radio.

Hey Guys- I want to do something a little different for this episode of First Contact. About two and a half weeks ago I interviewed Ev Williams who founded Twitter and Medium and Blogger. And I had asked him you know about the Corona virus and his thoughts on it and two and a half weeks ago I would say, here in the United States, everything looked very very very different. And so this episode as we release it, I wanted to talk to him again and ask his thoughts on it now. Because you know this is such an extraordinary moment and I would say that a lot of us are grappling with “what does this virus mean for us?” “what does it mean for our families and our parents and our loved ones?” and a lot of us are beginning to self isolate, to go home and spend a lot of our lives digitally. And I think there’s extraordinary power in what’s about to happen in our relationship with technology and this fear during this moment. And so I wanted to chat a little bit with Ev about that in light of everything thats happened. Uh and to give you a little bit of a sense of where I’m at, out of precaution, I am uh self isolating and understanding the power of digital and digital connection and really trying to grapple with what it’s going to mean to be human in this era where there’s so much fear and we are relying on our digital connections. So bear with me for the sound, how we’re going to do this is I decided to go back and interview him but it’s a phone call and I had to take it from home, so bear with us for the sound and we’re going to play that interview, and once we play that -it’s only 15 minutes- we’re going to get to the main interview where you can hear about the future of media. And the thinking behind this is this is a future facing conversation, and whats occurred in just the last week here in the United States, is I think game changing for the future and what it means for all of us. So take a listen and we will have the other part of the interview right after this phone call. 

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Laurie Segall: All right. Okay, here we go.

Ev Williams: All right, let’s do it.

Laurie Segall: All right. As I’m sitting here self isolated in my, in my New York apartment. Um, you know, everything feels really different now. And I had asked you at the time two and a half weeks ago like how worried about Coronavirus are you. You said something like ten percent worried, and by the way, I was kind of with you, because I don’t think any of us thought, what was going to happen was going to happen. Um-

Ev Williams: Right.

Laurie Segall: So I wanted to give before like we play the episode for folks and all that kind of stuff, uh, because so much has happened in the two and a half weeks that we sat across from each other. And by the way, we would not be sitting across from each other now.

Ev Williams: Right.

Laurie Segall: Um, we’re remote, given the state of things. Like how, how are you feeling about it now?

Ev Williams: Uh, very different, and I mean I think it’s it’s an understatement to say so much has happened in two and a half weeks, because it feels like it’s really two and a half days everything has changed. and I think everyone, especially if you spend, spend a lot of time on Twitter as I have. I think I’ve spent more time on Twitter in the last week than in the last few months, and that’s just, it’s pretty terrifying. It’s easy to get completely swept up in the stories and the, the rhetoric. And there’s a lot of noise, but I think there’s a lot of really valid, concerning information coming out.

Laurie Segall: Yeah. How do you think … I was thinking about this, because like I’m home. and I think increasingly we’re all going to be living these digital lives for the time being. Like-

Ev Williams: Mm-hmm.

Laurie Segall: … by the way it’s so weird to be sitting here talking to someone who created like, you know, major companies that shaped the modern internet, right? And, and I think we’re in this weird mode where like we’re going to be really relying fully on living in a digital state for a little bit. You created Twitter. You created Blogger. You created Medium. Like how is our relationship with tech gonna change do you think in the, in the coming weeks, maybe months?

Ev Williams: Um, I don’t know. I haven’t had a chance to think about it too much, but I’m very, I think, in some ways grateful and appreciative of just the infrastructure we have now to deal with this. And it’s fairly recent, and this isn’t even a thing. Like Twitter, I think, shines in moments like this. And that’s great, but all the other infrastructure we have now. Just the fact that, many of us are in any way have the, the broadband and the videoconferencing actually works, and the things we need to do our jobs and stay informed are there. And so it’s feasible. And actually for many companies, at least like mine, not that disruptive all things considered. The most disruptive thing is, is probably for most people I know the kids being out of school. It’s, uh … Um, that’s the hardest thing about working at, at home. But, I think that being fully immersed in the digital world and being further apart individually and even not having the opportunity to break from that, even if that’s your day to day job and then it’s, it’s evening time, and you don’t have that opportunity to go out in the world and connect with friends face to face or go to restaurants or go to a show,I think that’s going to be hard.

Laurie Segall: Yeah. My whole career I’ve sat across from people like you and asked questions like with tech how do we maintain our humanity.

Ev Williams: Mm-hmm.

Laurie Segall: I feel like, maybe it’s kind of personal to me right now, because I’m sitting here self isolating. Like, and the only connection I have now is like, it’s so weird, I’m literally doing this interview with you where I’m taking a call. And to give you a sense I’m basically like trying to make sure the sound is okay under a sheet . You know? Like to give everyone a very authentic sense of like what this is like. Um- As we talk about like the fear as like we’re going to live totally digitally to a degree, how do you think we can maintain our humanity during this time?

Ev Williams: Well, I think the, the counter is that the pandemic affects us all. Obviously it affects some people worse than others, and we’re not all, in exactly the same boat, but it is … it brings out humanity is what I’m trying to say in, in a way where, So, I think it makes it much clearer as any real, real crisis does or any threat, that, you know, what is important. And people usually come back to the same things about friends and family and, and caring about your community. And so it’s a weird situation, because you can see that. You can see that online, even though people aren’t necessarily doing that physically. At least what I see and what I think about is, is the caring and how do we, how do we help each other through this. So that part of our humanity, I think it will bring out.

Laurie Segall: Hmm. This is where I like to get specific. So how are you going to do it? How are you going to make sure?

Ev Williams: Well I’m very … I feel very fortunate that I’m with my family right now and with, a couple close friends. And so we’re, we’re, hanging out together.

Laurie Segall: Hmm.

Ev Williams: So I think there’s, um … I mean for me just I had a delightful conversation with my seven year old – … and, we’re in the same place. So I’m glad I don’t have to talk to my seven year old through videoconference, but, um, he’s in great spirits so far, because he’s at … you know, gets to skip school. And, uh, we had this funny conversation last … He actually asked me last night, “If you had to die not of old age, how would you die?”

Laurie Segall: Mm-hmm.

Ev Williams: And it was a pretty deep conversation with, uh, with him. And so… It doesn’t get much more human than that.

Laurie Segall: Yeah. I know. What was your answer? Hopefully it wasn’t Coronavirus. Please tell me it wasn’t Coronavirus, Ev.

Ev Williams: No, it was definitely not getting sick.

Laurie Segall: Okay.

Ev Williams: It was definitely-

Laurie Segall: Okay, good.

Ev Williams: Sickness seems to be … And we went, as, as seven year old boys will do, we went down some pretty gruesome routes there after that, which I’ll spare listeners.

Laurie Segall: Um, it feels like we’re also getting to live in this full on digital almost like experiment as we all start isolating in fear of the virus. I sat down with you for over an hour, and we talked about the future of media and your thoughts. When we come out of this, do your thoughts change at all on the future of media given what this almost like digital experiment we’re beginning to live kind of looks like? Does this change how you feel about the future of media?

Ev Williams: Uh, I haven’t really had time to think about that deeply yet. Um, and, I would guess in the very long term no-

Laurie Segall: Yeah.

Ev Williams: … but, I think what’s very clear, this transition to Medium the last few days is this crisis has sucked the air out of everything else. It has our full attention, and, I mean that’s, that’s having a dramatic effect on media right now. Um, and how long that lasts is impossible to predict. I think obviously things are going to get worse. It could be if we were to talk in two and a half more weeks, we would be in a completely different state.

Laurie Segall: Yeah.

Ev Williams: Um, and, and it’s going to get gruesome, so certainly the shorter im … term impact on media is it’s hard to talk about anything else, and then the longer term is if there’s a likely recession and how does that affect consumer spending, and therefore the ad business as well as subscription businesses. I expect all that to have pretty big ramifications over the short term, but that short term I, I would … you know, is months and years.

Laurie Segall: Yeah. … You know, I know that there could be a panic. People’s lives could be at risk. Will this change the rules around social media and misinformation? Or have you seen any changes even in the last week or so? Or do you sense anything changing?

Ev Williams: Um, I don’t know. I’ve been just in my own efforts to get information. It’s interesting, because I had curated my Twitter followings well enough that I felt like I was getting very high quality information, but then again, maybe everyone feels like that. I would dip into … I would see some retweets and some comments via my timeline on a whole different Twitter where there’s some serious BS being bandied about. And and I was like, “Wow, people are still saying this?” You know, like downplaying the whole thing or having conspiracy theories. So that is definitely out there, and bad actors will take advantage of, heightened stress and any opportunity to, to spread misinformation, and this is probably the biggest one of all times. Will that lead to anything? I don’t know. I don’t know.

Laurie Segall: It’s a leadership moment for everyone, right? Are you, are you finding it’s changing you as a leader? How do you want to lead during this time?

Ev Williams: The big thing for me focusing on the company is just trying to help people feel some sense of stability as we go through this and there are obviously going to be companies that, are going to be hit hard, going to have to do lay offs, aren’t going to be able to get their next round of funding. I’m not really worried about any of that for us but it’s going to increase. You, you know, you see headlines about that, and if you’re in a start up then you wonder, “Oh, is my company in trouble?”

Laurie Segall: Yeah.

Ev Williams: And so I’m trying to, to create, some sense of stability and also just trying to rally people. And everyone wants to do, positive things, and so what we see on Medium is like there’s a lot of good information on Medium so someone had the idea, “Hey, we … what if we made everything around Coronavirus that we have control over, we put … make sure it’s outside the pay wall.” And so people don’t feel like, you know, they’re being charged for what can be important information. And so looking at those opportunities to actually be of service and not opportunistic, but actually like, “Oh, if … there’s a role we can play,” and we feel fortunate that we’re … I mean, this is why we exist to help people get access to good information and good ideas as well as express things and connect with other people. And so, so we, we feel like we can be relevant and encouraging people to come up with those ideas, act on those ideas, change plans that maybe, you know, our longer term plans don’t change. But I think that helps both … It helps other people, but also help, helps the team, you know, really feel like not being totally overwhelmed and distracted by the bad news if you feel like you can help something.

Laurie Segall: Right. Are you afraid?

Ev Williams: I’m, I’m not afraid much for me and my family, but for the yeah, for the world. For sure, and for all that … I mean, there’s definitely going to be a lot of people really sick, and, everything I read and talk to doctors I know say we are … the … our healthcare systems are definitely not prepared. Um, yeah. That’s scary.

Laurie Segall: Alright well thank you for doing this. I appreciate it. Stay healthy. Wash your hands.

Ev Williams: All right.

Laurie Segall: I’ll talk to you soon.

Ev Williams: All right. Thanks, Laurie.

So that’s it for that portion of the interview. Now this is the portion of the interview we taped two and a half weeks ago. 

Laurie Segall: What do you think communication looks like in 50 years? 

Ev Williams: Oh, wow. 50 years. I tend to think things get more extreme. I think a lot of the uh, sci-fi visions of people being totally jacked into the matrix whether it’s VR or more likely AR, augmented reality. Like the fact that we’ll have heads up displays and glasses that project information to our eyeballs. I think that will totally be true. 

Laurie Segall: And do you think that augmented layers we’re all just gonna be in like a giant video game of sorts?

Ev Williams: Yeah, basically.

I want to start by taking you back, it’s the middle of  Winter in 2016 . I’m meeting up with one of the founders of twitter, Ev Williams. Its been six years since I last interviewed him, his chosen spot: a bookstore in downtown New York.

Now I remember thinking at the time this guy founded three major tech  companies: Blogger, Twitter, and now Medium, – a publishing platform. And he wants to speak amongst books? Books which have almost become like ancient artifacts because of the digital world that he helped create.

But when you get to know Ev, you’ll understand that words, thoughts, and the sharing of ideas are in his DNA. Knowing him a bit better now,  I couldn’t think of a better place for us to talk about the future of technology.

I’ve interviewed Ev many times over the years and of the Silicon Valley CEOs I’ve spoken to, he’s one of the more curious founders I’ve met.

Where other founders like to talk, you see him listening. He’s quiet and he sits back but knows how to read a room. And most importantly, he has a proven track record of creating communication tools that fundamentally change the way we speak to one another. 

So pay attention to what he has to say about the future of media, there’s a lot to sift through.

Will augmented images be projected into our eyeballs?

Will Silicon Valley ever move beyond the attention span economy?

Will the future of media look like an all-encompassing video game?

And why is it that someone who has experienced insurmountable success is still so afraid to fail? 

There’s a lot to explore… and no one better than Ev Williams to help us make sense of it all.

I’m Laurie Segall Segall and this is First Contact 

Laurie Segall: Ev, you are the founder and CEO of Medium. Also, you were Twitter CEO for severall years, and Twitter came out of Odeo, which was a podcasting platform. So you were way ahead of your time. And before that you created Blogger, which pretty much revolutionized blogging online, wouldn’t you say?

Ev Williams: As opposed to the blogging offline that we were all doing in the early ’90s?

Laurie Segall: Fair. Moving on. Well this show is called First Contact, and I am – was super excited about this, because I did some digging for our first contact. Do you remember our first contact?

Ev Williams: Was it at South By?

Laurie Segall: Yeah.

Laurie Segall: It was 10 years ago. And, you were the CEO of Twitter at the time.

Ev Williams: Mm-hmm.

Laurie Segall: Okay. So I found a photo. There it is. Oh yeah. Yep.

Ev Williams: Oh, wow.

Laurie Segall: Yeah. I wish our listeners could see that. Um, but that was 10 years ago, and I-

Ev Williams: Why am I in the middle?

Laurie Segall: Well, because I, I think I was interviewing you, it was March 23rd, 2010, and I was interviewing you. I was actually, um, a production assistant at the time, pretending to be a producer, um, but interviewing you, as the CEO of Twitter, so much has happened in 10 years, I would say. We talk a lot about kind of beginnings here. I want to go back to Nebraska.

Ev Williams: Hm.

Laurie Segall: Where you’re from. And talk about how you got into all of this. So, I watched a commencement speech that you did, and you were talking about, this giant idea sharing machine that you were into.

Ev Williams: Mm-hmm.

Laurie Segall: This thing you’ve kind of always been obsessed with. And had something about, like, opening up the second edition of Wired Magazine and just, like, falling in love with this idea of connecting our brains.

Ev Williams: Right.

Laurie Segall: What about it was so interesting to you? And don’t give me this, like, ah, you know, like, large answer, like, because, like, I- You know, I just hate when founders do that, when they’re like, “Oh, I just really wanted to connect the world.” Like, that seems so broad. Like, you were this guy in Nebraska, like, and you opened up this second edition of Wired, and you were just like hooked, in some capacity? What was it?

Ev Williams: So you don’t want a large answer. Can I give a Medium answer?

Laurie Segall: Yeah. Yeah, yeah.

Ev Williams: That’s a joke. I think I was captivated by the notion of getting out of where I was, because I was from this very small, rural place, and, pre-internet growing up, and I’d never traveled, and, I just was itching to… see the world but, not in a traveling sense necessarily, but just to kind of break out of there. And so the idea of getting access to the world and ideas through this little box on our desks as it was at the time was super compelling, and, it wasn’t, I wouldn’t claim it was altruistic of connecting the world. It was just the idea of being connected, and it was more from a, um, idea-knowledge perspective than a social perspective. I wasn’t necessarily looking to make friends but, um-

Laurie Segall: Did you have friends growing up, or?

Ev Williams: Did I?

Laurie Segall: Yeah. You- Was it… Were you kind of like a lonely kid, or was it a, I mean, was it kind of a form of connection?

Ev Williams: I was, I was lonely, but I wasn’t a loner. I was social. There just were very few people, and, uh, so, I think I was spending a ton of time alone. And by this time I had gone off to college, actually, and then I, I had quit, but I was looking, I was still having that feeling of, there’s more out there in the world. In fact, my cousin, I had a cousin from Kansas City, which was the big city, and he came and visited us on the farm one time, and he gave me this book, Jonathan Livingston Seagull. Do you know that book?

Laurie Segall: Mm-mm.

Ev Williams: Um, it’s like a children’s book. It’s a fable, and it’s about this seagull who is different, and he wants to, to, break away from his flock and basically… and my cousin wrote a note in, in the book saying something about, regarding that, that he saw that in me, and that I could, you know, get out of there, or, uh, um, you know, it was okay.

Laurie Segall: Hm.

Ev Williams: And so I think it was that yearning to be… uh, in a different place than I was and more connected to the greater world that really compelled me.

Laurie Segall: Hm. I, um, I think for me, so growing up for me, like, I was the only Jewish girl at a very Christian conservative Southern school and had parents that were divorced. And I think for me, I, because of that, for some reason I always felt like a little bit of an outsider, and so I always liked outsider stories.

Ev Williams: Mm-hmm.

Laurie Segall: And that’s why I went to go on to do what I did, I think, which is tell outsider’s stories, which you could argue, you guys are now all insiders in some kind of way. You guys are all very powerful now, but, um-

Ev Williams: I don’t know who “you guys” is, but I still feel like an ou- outsider for sure.

Laurie Segall: Tech, Tech CEO. So I guess I, I guess I, I ask you that, um, to a degree. Like, when you say you’re talking about this book, you’re talking about this idea of, like, doing something big or being different. Where do you think specifically that came from?

Ev Williams: I don’t know whether it was, was something I was born with or just, I mean, there’s all kinds of narratives that I could imagine.

Laurie Segall: Mm-hmm.

Ev Williams: In wanting to, to do something important growing up in a place where I didn’t feel important, but as I got into it, it was, it was compelling in its own right, just technology in, and the internet specifically, in the, um, early ’90s, I guess, mid-90s, and then started Blogger in ’99, was, was just so interesting because of, you could sense the potential, and, not that I or anyone saw the future in detail, but you, there was, the, the talk about it at the time, about connecting the world and sharing ideas and information at our fingertips and all the media ever produced being, you know, accessible and, all that is true now and we take it for granted, and that was such a, like, it’s a transformative thing and the way I look at it now is, is that, there’s so much that we take for granted that has emerged over the last 20 years, and all kinds of it is, is broken, and is it good or bad, and, and there’s, there’s problems that come with it. And I think it’s all still very interesting, because in 20 years, we’ve completely changed how humans get their information and how they communicate with each other, and of course it’s broken, and of course we still have to work on it and make it better, and so while a lot of the novelty has gone away and a lot of the, the painful reality is, is, is come up, there’s still all these exciting and really cool things that we don’t even think about now that I think are still pretty cool. But back then it was, oh my gosh, could this really actually be true?

Laurie Segall: I read that you kind of went West, and because you were looking at Silicon Valley, which you thought was just, like, geniuses, I guess, like, Baywatch and, like, something else. I know that’s gonna come back to haunt you now that I’ve said it. It was like Baywatch geniuses and something else was like Silicon Valley.

Ev Williams: Probably. Yeah.

Laurie Segall: How did, how did you feel when you first got there?

Ev Williams: Yeah. That was my, so, when you’re not from California, when you’re from the Midwest and you only know California from TV and movies, it kind of all blurs together.

Laurie Segall: Uh-huh.

Ev Williams: So you assume that surfing and the beach have something to do with- with computers and, and everything else, but, um, yeah, northern California, I, I traveled to California for the first time when I was, like, 24, 25, and I saw the ocean for the first time when I was 20. So that was on the other coast. I went to Florida. But, so everything was new, and, I was nervous, but I did feel in California… uh, instantly, I noticed two things. One is, there were no bugs. Like, in the air. It was during the summer and it felt like a movie set.

Laurie Segall: Hm.

Ev Williams: What did I know of movie sets? But it, because I was in California, that’s what came to mind, because in Midwest, in the summer, there’s bugs. And it felt very strange and, and not real. But it also felt very comfortable in that, because everyone there seemed like was from somewhere else, and so that feeling of being an outsider was, was lessened, because it was a community of outsiders. Those are the two things I remember when I first got there.

Laurie Segall: And so we fast forward all these, all these years later, we talked about, like 20 years later, and this whole idea of this idea sharing machine that you had in mind, um, you connected the world in all these different ways with Twitter, Medium, Blogger. I know everyone asks you now, like, how do you feel, how do you feel about what’s happened with Twitter, how do you feel, all this stuff, and I remember the headlines, like, you know, Ev Williams is gonna fix the internet and all this stuff, like, but like, behind the scenes… Like, when you’re sitting at the dinner table, and, like, you’re with your wife and kids, and like, you think, like, whoa, you really did create this incredible ecosystem for us to all, you know, share information, how do you feel about it?

Ev Williams: Well, the first thing even hearing that, I feel uncomfortable, like, saying that I did these things. I was part of something, and I think the main thing that I feel is incredibly grateful to be a part of, um, both Twitter and the greater, the, the internet as it’s, um, grown and emerged over the last couple decades and to be, just at, at the forefront of that and, and helping that along was just an incredible experience that, yeah, I feel lucky to have been a part of is the main thing. And, I don’t spend a lot of time lamenting choices we made or, or regret. I’m very focused on what’s new and interesting and, and what can we do next. Now over the last six months I’ve been living in New York after spending 22 years in San Francisco and, and Silicon Valley so mostly I just feel like there’s new interesting stuff to explore, and I don’t feel like because I was apart of something, um, I, I get questioned, like, do I regret things or would I have changed things, and all that gets very complicated and nuanced, um, and I don’t, um… I don’t know how to answer those questions.

Laurie Segall: You said something about, make sure technology makes things easier, but do you worry that things got a little bit too easy?

Ev Williams: Yeah. Yeah. I think, so that, um, something I realized a few years ago, and Tim Wu has, has written some great stuff on this, but I realized at one point that the way to make something successful in technology and probably most businesses but at least technology-enabled businesses was simply to make something easier, something that a human wanted, you make it easier, and that could be connection, it could be in romance, it could mean status, it could mean goods delivered, it could mean the answer to, I don’t, information, and you, you go through the list of major things people want, entertainment, and you look at the major tech companies, and what they’ve mostly done is that this thing that people have always wanted, we made substantially easier, and you look at how the big tech companies have, what they’ve gotten really, really good at, and take Amazon, and it’s one click, and literally patenting the idea of buying something with one click, that was a major value creator, and then the free shipping in Prime so you didn’t have to think about it and always having the lowest price and having the best selection, and, and Google, how they’ve been obsessed with speed and low friction, and company after company has, has basically used technology to reduce friction and make things easier. So in many ways that’s great, and then obviously humans are humans and they, they want things that aren’t always good for them. And I think society as a whole has kind of gone through this sugar binge. And now, we’re, we’re reeling in that and saying, oh, well, like, we shouldn’t have allowed all that technology, or, we shouldn’t have, partaken that much. But, I think we’re figuring out how to deal with that. How are we gonna deal with the fact that there is all this stuff that’s immediately available and, and it’s exploiting many base instincts, in the same way that junk food exploits base instincts, and saying, how do we delay with that? How do our kids deal with that? How does society deal with that? And how are people manipulating that and manipulating us in ways we don’t even know?

We’re gonna take a quick break to hear from our sponsors, but when we come back, Ev talks about clickbait, the worst offenders, and why Medium is different. 

Also, If you like what you’re hearing, make sure you hit subscribe to First Contact in your podcast app so you don’t miss another episode. 

Laurie Segall: I, I read from a blog post you posted it  was like 2015. You said you, “I was never a fan of RSS readers. Sometimes they made things easier to read, but I didn’t like how they took content out of context, especially from sites where I liked the design.” But then you kind of went on to create Twitter, which, like, it seems like it’s like- Everything  is just, like, can be taken out of context to a degree, right?

Ev Williams: Yeah. Yeah.

Laurie Segall: I mean, maybe that’s a, that, that doesn’t make complete sense.

Ev Williams: Or creates a new context.

Laurie Segall: Yeah. But it certainly seems like this moment has kind of lost a little bit of context, or, or something.

Ev Williams: Mm-hmm.

Laurie Segall: Like, what do you think is the solution to, to some of, to some of our Internet’s latest issues?

Ev Williams: I think context has a tremendous amount to do with how people interpret information as well as what they share, and, I think what we’re focused on Medium on doing is enabling thoughtful and meaningful content to, find its right audience and, and find a receptive audience, and what we’re fighting against is the fact that there is, the, the way that, that the content distribution systems of the internet have evolved over some time is for optimization of attention. On the internet, it’s like, the goal is to distract you. And, the reward is if you actually capture enough attention cheaply enough and get, distract enough people, then you make money. And that’s what we rely on for our information. And so I think it’s, it’s, it’s systemic. It’s not a matter of, well, we need better publishers or we need better, um, better systems to control the bad stuff or we need to kill misinformation. It’s much more fundamental, I think, in how, are there systems that allow people, whether journalists, writers, um, uh, experts, people who are sharing information and knowledge, is the incentive structure rewarding the right thing? I think it, for the most part it’s not today.

Laurie Segall: And so, uh, I mean, I remember, maybe it was three years ago, I mean, you’ve been ta- you were kind of talking about this before people were talking about this. I give this to you.

Ev Williams: I’ve been kind of obsessed with, on this for a while.

Laurie Segall: You, you’ve been obsessed with this. I mean, it’s, like, okay to talk about this now- But when you started talking about this, it kind of wasn’t okay to talk about as a Silicon Valley leader. Like, I will give you that. Like, you had stepped away from Twitter, but you were on the board at the time.

Ev Williams: Yeah.

Laurie Segall: I don’t think people fully understand this. Like, the first time you said this, like, it was kind of controversial, right? Like, now everyone is like, oh, the attention economy, and like…

Ev Williams: Mm-hmm. Mm-hmm.

Laurie Segall: And, you know, our attention is not being, now this is like a whole buzzword in Silicon Valley. But like, when you came out and you were like, our attention is under attack, like, I can imagine, first of all, that got awkward in the boardroom at Twitter because, isn’t that their business model, correct me if I’m wrong?

Ev Williams: Correct. Twitter does make its money from advertising.

Laurie Segall: So, was that awkward?

Ev Williams: Um, yes and no. But, I mean, maybe… it gets complicated, because then I, um, not, I’m not on the board of Twitter anymore. But I do make a distinction between types of advertising, and the advertising and distribution systems such as Twitter and, and Google and content advertising but it gets a little, little complicated. And so, advertising in general-

Laurie Segall: Who’s just like the worst defender? 

Ev Williams: Oh gosh. Um, There’s no actual, I, it’d be too hard to name the worst offender. I mean, we’ve all been across the web and seeing these, um, just terrible sites that are overloaded with ads and the clickbait and there’s, there’s, we can all recognize the worst offenders when we see them. But I think about what, what’s complicated about talking about this? And, in the Twitter case, I don’t think that’s at all the worst offender, nor is Google. There’s a, a defensible argument that that’s the best way to, to fund a, an information distribution system because the content itself doesn’t get promoted based on its advertising, which is different than other systems where, where the content has the advertising embedded in it. There’s a time when television seemed to be trash and movies where the only high form of, um, video entertainment. And now that’s no longer true. What changed to make that no longer true was the best television stopped being funded by advertising. And then consumers got a much better value proposition, a much better product, via streaming and first of all, HBO and other premium channels and now that’s the norm. Music went through the same thing. There’s a time when music was, the whole music industry was going to be out of business because of Napster. And then obviously for decades there’s commercial radio. And now it’s healthier than it’s ever been. And the consumer value proposition is amazing. For 10 bucks a month, you can get access to everything you’ve ever wanted in these great playlists and discovery. So I think there is reason to be optimistic that if you change the system and what’s rewarded, we can get to a much better solution.

Laurie Segall: So  take me to the reason behind building Medium and what you found because this is,, this is a reaction to a lot of the stuff we just spoke about.

Ev Williams: Totally. So we, I started Medium eight years ago, so 2012, which was before, certainly before a lot of people were talking about advertising and before fake news, I mean, fake news at the time was, was The Onion and the Daily Show. It was delightful. Um so I saw what happened with social media, which I thought added this whole interesting layer and realtime,  information exchange speaking of Twitter specifically, and there was nothing like that on the more on the bigger side, so to speak. So, Twitter people would exchange links and then you’d click off to a website and you’d read an article and often it wasn’t yet optimized for mobile. And it had all these ads in there and it was kind of an, and if you were publishing a website, then you go to Twitter or search or email and try to get someone to come there. And if they came, they weren’t, they probably weren’t logged in. So if you wanted the comment or something, just the systems didn’t feel modern and they didn’t feel evolved and they also didn’t seem like, again that, that the best stuff was floating to the top. So the idea was create a place where anyone can write and publish and help the good stuff, find, you know, find audience. And so that’s what we created in 2012 and it’s still the case today. Medium. Anyone can write on Medium, anyone can publish for free. It’s read by about 140 million people a month visit Medium. Many of them, log in and use the app. Many of them are paid subscribers. It’s all ad-free and it ranges from the amateur storyteller or the individual who wants to rant to professional journalists and publications.

Laurie Segall: So where does Medium fit  in the modern media landscape? If someone who sees kind of into the future and says like, this is where I think media is going, where do you think it fits?

Ev Williams: Well I think it’s, um, our aspiration is to be the best place to publish and find quality, thoughtful content on the internet. And, I think we can achieve the best place to publish for the vast majority of individuals and organizations because it’s just way easier and more efficient to publish to a network. And the same reason for the same reason that if you have a tweet to share, you don’t share it anywhere, but Twitter, if you have a video, you might put it on your own website, depending on what your goal is. But if you just want audience, you’re going to probably going to put it on YouTube. So we’re trying to achieve the same thing as the default and the best place to, to find your audience and to build an audience. But without the downside of, of having to, monetize with only advertising and really where, where a system and, and when you change the business model and you change what’s rewarded, then you create a space for quality and thoughtfulness and help. Good stuff rise to the top. So we’re not trying to get everyone to publish on Medium, but we’re trying to get those people who are really trying to put stuff out there that is a value and is worth, to put it on Medium and make it the best place to find that stuff. And, uh, that’s our goal.

Laurie Segall: How has the subscription model been? I mean, has it been difficult to get people to subscribe? will people pay for quality? I mean, this is the question of the internet, right? Will people pay for quality content?

Ev Williams: People will, people will, I mean, we’ve been doing this subscription for, we’re entering our third year or just entered our third year, we’ve done three years. Sorry. Um, and, um, it’s gone very well. And so the…

Laurie Segall: The founders always say that. What does that actually mean?

Ev Williams: Yes. Um, well we don’t share a subscription number,

Laurie Segall: Okay.

Ev Williams: But most, most people are, are, are surprised. And what we’ve learned. So it’s been, um, super interesting because what we’ve done is not just put up a paywall and charge money, which a lot of publishers have done. And even three years ago when we started that, the default assumption was no one will pay on the internet or certainly no one will pay for written word content. That’s all free there. It’s ubiquitous, there’s too much of it. And on top of that, Medium  is mostly user generated content. It’s an open platform anyone can publish. And while we now have an editorial team that publishes some, the vast majority of what’s on Medium comes from individuals who can publish outside the paywall or behind the paywall and get paid. And so we, we did something that, that is very unusual, which is with an open platform, charged a subscription. And so open platforms lend themselves to advertising business models. This is YouTube, this is Twitter, this Facebook. This is everything because it’s all about volume and quantity. And as the platform, you generally don’t pay for content. And so advertising tends to make very little per content, especially internet content, but, but there’s lots and lots of it. And the quality doesn’t matter if you’re making money from advertising cause people aren’t paying for it. And for all those reasons, advertising is a model that makes sense for, for a platform where as a publisher who wants to charge a subscription and you think of the new Yorker and the New York times that, um, and it’s like, Oh, it’s all about quality and brand and um, trust. And so what Medium has done is what the biggest thing we’ve figured out is, is how to blend these two because we believe deeply in the open model and that the idea that great ideas can come from anywhere and many of, historically the best stories on medium, that had been surprising and unique and valuable and interesting have come from places you would never expect. And we have lots of famous people when we have professional journalists and we have all kinds of people that publish on Medium. But time after time, the thing that comes out of nowhere and blows people away is because it’s open and free and anyone can publish. And so we hold that dear and we hold the fact that, people should pay for quality and we should reward quality and that lenses. So, what we’ve done is blend those models and we do a lot of work to curate the best of Medium help, make sure that people are seeing both what’s interesting to them and what’s actually good. And when we do that, what we find is, is people happily pay.

Laurie Segall: Do you worry that especially now that good information is, is harder and harder to get? I mean, do you think it’s, we’re going to have this almost like junk food epidemic for information where like you’re going to pay like only the people who can afford it are going to be able to have good information. 

Ev Williams: Hmm. Yeah.

Laurie Segall: And then, and so when your kids grew up, if they grew up wealthy, there’ll be able to have good premium information and then if not, they’re going to have like the bad information that’s like the, you know, look in the dumpster of the internet, and then we’re just going to create a world of haves and have nots. Like, do you worry about that?

Ev Williams: It’s, it’s a good question. I think there we need to think about that a bit more. I think in the near term we won’t have that because one of the, one of the nice things about the model like Medium has, which same as the New York times has, is the people who are willing and able to pay it actually are subsidizing it. It’s not a hard paywall what happens is it’s actually a little bit of a, it’s, it’s good for everyone in the sense that the few people who pay for Medium enable a hundred plus million people to read Medium and not pay. I think that can continue. I don’t know if that will always be the model, but what that allows is then because certain people are paying and in some authors and publications can do very well in a subscription model who couldn’t even survive in an advertising model ‘cause different types of contents, not just that it’s paid for differently. It’s different types of content will work better in advertising model versus a subscription model. and one of the things that’s been really, informative as we’ve been building this is engagement and value are not the same thing. And if you build a, an advertising based platform, what you learn and what Silicon Valley engineers obsess on all day long is how to increase engagement. And engagement is measured in all kinds of ways and everything’s measured and it’s all about making the charts go up. And it’s like if we move this button or if we change the density of the listings or if we do this, that if we send more notifications will people spend more time, and so you have these charts and you try to make the charts go up. And in an advertising business, those charts are very tightly correlated with how much money the business makes because what you’re selling is that attention. So it’s all about capturing more and more attention. With a subscription business, so at Medium, we have all those charts as well. And, and you know, we’re very familiar with that model and what we notice is those things you can measure do not necessarily correlate with the business. They don’t necessarily correlate with subscription. Because what we’re asking people to do is make an evaluation of is this worth my time, not just worth my time, but am I willing to pay for this? Do I feel good about that time I spent? And, there’s no way to actually measure how much value someone is getting except if they’re paying for it. And so what we found is there are certain types of content that will be consumed and, people are less likely to pay. And there’s other content that, that may be consumed in less numbers, but those people are very happy and we can all imagine things that, may not be wildly popular but we feel really good about consuming or we get a lot of value out of personally. Um, and that is worth something to us. So that’s a roundabout way of saying by building these subscription models or this model in particular, we can enable things to exist that are extremely valuable. And for a lot of people they will be free and they’ll, because they’ll be subsidized by the people that they’re really valuable to. And the writers who are writing them are going to be able to get paid in a way that they would have never been able to in an advertising model. And they’re going to reach an audience. They would have never  been able to say in a book model because they’re still open and free out on the internet.

We’re going to take a quick break, but when we come back, almost ten years after leaving Twitter, Ev Williams explains why it’s still difficult for him to talk about exiting the company he founded.

And if you have questions about the show, comments, really anything, you can text me on my new Community number: (917) 540-3410.

Laurie Segall: Um, it’s been a year since you’ve left Twitter’s board and you were there for 12 years and I think leaving any job and I mean you weren’t day to day.

Ev Williams: Right.

Laurie Segall: I know you created this company. Um what was the hardest part of like completely stepping away?

Ev Williams: Um, well it was very hard to do that. Um, it’s something that I thought about doing for years and, Twitter is a very large part of my life. My identity. Like I said, I feel very lucky to have been a part of it. I also stayed on the board because I wanted to be helpful and I felt an obligation to be, to be helpful. And I don’t know if I was, but I, I tried my best to bring conversations and participate in conversations that, that were brought to the board or that, or that I thought we needed to have on the board and that ranged from how to be helpful to the business to how to help make sure we do the right thing. And, there was a point where I felt like for the time I was spending I could be more helpful doing other things. And so that was sort of my equation. The other reason, I liked being on the board for a long time. It was tremendously educational for me to see as a, as a student and a builder of businesses to see a company go from, from zero to a public company worth billions of dollars and having thousands of employees and seeing the issues that came up and seeing the different rounds of, of management and leadership and, how they handled the many, many challenges that were extremely complex was even if I didn’t feel I was always being helpful, I was always actually learning a great deal. And so I started to see decrease in returns just because the company had been the size, it was in public for a while. And, so that’s why I got off the board. As far as the most difficult part, I think it was just giving up that part of my identity, although I realized, you can’t unfound something. So I, it’s still, it still is. I mean the main people, if, if people don’t know me as like, um, I don’t usually volunteer that information, but other, someone else will say, I co-founded Twitter. So the identity hasn’t really changed that much. But, but I felt like, am I making a mistake? Should I, or it was probably the obligation part. I still also care about the company and so many people there that I was like, am I, it’s like I’m quitting them. It’s like I’m breaking up with them. I had sort of that feeling and like, uh, like I, I shouldn’t do that and I owed so much to the company that I should just stay as long as possible. But I got over that. 

Laurie Segall: Was there like a point that you were like, is this time to go? 

Ev Williams: Um, yeah, it was the beginning of last year, so, yeah, a year ago I, I often, you know, just try to assess life over the holiday break and say like, what do I want going forward? So it was, it was right after, after that that I, I think it was after that, that I, that I told, um, Ahmid and Jack. 

Laurie Segall: Hmm. It is funny though, I think, um, identity is a really big thing for tech founders and because startups are like children to a degree and you live and breathe them. I think that, um, people don’t talk about to get to where you’re at and the seat where you’re at, where you can just casually talk about a lot of these things. It comes with like an extraordinary amount of um resilience and a lot of these downtimes that we don’t really talk about. Everyone has failings in their jobs? Everyone goes through things. But how did you, because I think we can talk about it now that you’re seeing, you know, we just talked about Medium. And it doing well. How did you move on? How does one move on?

Ev Williams: Um, it’s still not that easy to talk about. But time is, is a big thing. It’s been a decade almost. It’ll be a decade this year, since I left. And, you know hopefully I’ve grown in that time and, gotten distance. And I also, I just see it much more balanced now. I’ve learned a lot about people and politics and relationships and I can own a lot of the, for a long time and just felt like this grave injustice and betrayal. And now I look at it more neutrally and say like, okay, I can see, I can disagree with this conclusion or how this and this was done. I can also see the logic and I can see also, the gift that I got of freedom and the ability to, to pursue different things. And, for a long time it was, I didn’t necessarily look out that way, but that’s how I think about it.

Laurie Segall: Let me see. You had a mentor who said during tough times, you had to change for the better or you just get frozen, how do you change for the better?

Ev Williams: That was actually, yeah, I forgot about that. But that was when I was still dealing with a lot. And, yeah, he said, given, given what you’ve done already, you’re, you’re going to be better because of this. You just don’t know how yet. And that started a long journey of sort of introspection and I dunno how much of it was recovering from that, but I think, I think had I been caught up in running the company for, you know, it was totally crazy for lots of years and probably still is, but, I probably wouldn’t have taken as much time to grow personally. And so that’s been part of what I’ve been doing the last few years via health, meditation, kids, family, you know relationship development, all of, all of those things have helped me create that distance and sort of that, the more even uh, view of it.

Laurie Segall: How do you take care of your head when you’re a founder and you talk about like you know taking care of yourself personally and- and that kind of thing?

Ev Williams: Yeah.

Laurie Segall: Like what do you, what do you actually do?

Ev Williams: What do I do? Literally, what do I do?

Laurie Segall: Yeah.

Ev Williams: I uh-

Laurie Segall: I mean I actually think like tangibles are kind of interesting.

Ev Williams: Yeah. So, the things I do now that I think looking back I was just silly not to have done before are the things that everyone  does. It feels cliché to say it, but I try to get enough sleep. So like seven to eight hours of sleep every night and I exercise. I meditate, I eat well or at least better than- than I did at one time. You know all the kind of the classic things. Um, another thing that uh, I think has helped a lot with the, with the culture and medium is just um, developing much better relationships with my team through training and workshops and stuff. That’s been really healthy thing for our culture and a very big difference from how I ran things in Medium.

Laurie Segall: Hmm. What do you think when you look to the future in 50 years, you have kids now, I mean what do you think communication looks like for your kids in- in 50 years? Are they even on Twitter?

Ev Williams: Oh wow.

Laurie Segall: Does CNN exist?

Ev Williams: Uh, gosh.

Laurie Segall: Like is advertising a thing? Like just take us to the future.

Ev Williams: Uh, wow. 50 years. I tend to think the thing, things get more extreme, but in more than one direction at once. So on the one hand I think a lot of the  sci-fi visions of people being totally jacked into the matrix whether it’s VR or more likely AR, augmented reality. Like the- the fact that we’ll have heads up displays and glasses that project information to our eyeballs. I think that will totally be true and a real thing. And I’m sure we’ll have ambient always on, audio in our ears and maybe even I’m- I’m not up to speed on the neurotransmitters you know sending information directly to our brains, but I know people are working on that. I think all those things will be true. I also and so, like everything else, that’ll be good and bad. It’ll be partially touted as oh, we’re not looking at our phones the whole time because we’re getting just the information we need. But I also think that’ll be overwhelming. I think hopefully because I like to be optimistic, we’ll get over the sugar high of- of information. I think the misinformation and fake news and abuse and all those things that are part of the internet today, I think there’s solves to all of those. I think that-

Laurie Segall: Really?

Ev Williams: Yeah.

Laurie Segall: Do you really think we’d get on top of this?

Ev Williams: Yes, I think we get on top of all of that.

Laurie Segall: I don’t know Ev..

Ev Williams: I think we get on top of all of that.

Laurie Segall: Like in the years that we’ve been talking it doesn’t, it- it feels like I don’t know.

Ev Williams: I think we get on top of all of that. I think it’s still really early. It’s still all driven by advertising and- and that’s fixable.

Laurie Segall: Do you think that, do you think that the fund of the business model of Silicon Valley changes in order for that to happen?

Ev Williams: Absolutely.

Laurie Segall: How?

Ev Williams: It has to.

Laurie Segall: What does it change to?

Ev Williams: Uh because-

Laurie Segall: Everything is subscription based?

Ev Williams: Most of the people, because everybody who can is going to pay for a higher quality information just like they pay for higher quality entertainment. Like you don’t know anyone who can afford it who doesn’t have Netflix and probably three other streaming services or Spotify or Apple Music and it’s just way better. And the same thing will happen with our news and information that we consume, as well as probably your social networks which will also exist, but they’ll all be much more. Now they’re just going to be a downside of that as well. Maybe there’ll be more  gated communities. Maybe there’ll be more uh, filter bubbles.

Laurie Segall: You’re just going to create like the ultimate I don’t know, Silicon Valley where like we can’t even be in your presence because?

Ev Williams: I don’t know what you’re talking about. I- I live in New York.

Laurie Segall: That’s… Okay.

Ev Williams: Um, so I think all that’s going to happen. There’s also going to be a, one- one trend in general is that the internet reflects the real world more and more over time. And so one of the reasons we’re going through, even  if you look at cyber security is because most- most of the internet was not built, was like communities that were small towns and didn’t have locks on their doors and then they, they became big cities and people decided they needed to take security much more seriously and we need police forces and that’s just, that’s taking a while. And so that’s all gonna happen I’m sure. I think it’s mentally and emotionally I am concerned about what the, that extreme looks like even if we’ve addressed some of the more blatant issues we have today and I, so I think on the other extreme there’s going to be hopefully enough nature or nature like, experiences where people can complete I think there’ll be a big trend toward completely unplugging, real life interaction and that will be a way to live at least part of your life.

Laurie Segall: Hmm. What do you think is um, well for actually will you go a little Black Mirror with me for a moment?

Ev Williams: Sure.

Laurie Segall: Someone in here has said to me like he’s like, “Well I’m worried about Netflix um, and the idea that like they’ll be able to measure your facial expressions and- and know the second,” you talk about this instant feedback and how bad it is.

Ev Williams: Yeah.

Laurie Segall: And- and know the second that you’re not interested-

Ev Williams: Hmm.

Laurie Segall: …and able to- to target and- and do that kind of thing. Do you think when it comes to the future of media like the media companies will be able to know the second we’re not, our attention is- is gone and be able to- to kind of act accordingly?

Ev Williams: I think that’s much more likely with CNN than with Netflix.

Laurie Segall: Do you think CNN will exist in- in 50 years?

Ev Williams: The brand will. Big media brands don’t die, but Netflix um, because when they start doing that it’s gonna be the same thing when we get someone to read something on Medium that they- they click on because it appeals to their base instincts, but they don’t value and so because, now Netflix may create an advertising business as well and be doing that. I don’t know if Netflix will be independent in 50 years, but they’ll probably be owned by Disney I hope not by the way. I just read that on Medium so, uh speculating.

Laurie Segall: What do you think is the single most important ethical issue when it comes to the future of tech and us complicated human beings?

Ev Williams: Most important ethical issue. Well the biggest-

Laurie Segall: What do we need to pay attention to.

Ev Williams: I mean  to frame it as an ethical issue is by the way I think Netflix will be all video games in 50 years too.

Laurie Segall: Why?

Ev Williams: ‘Cause they’re more compelling. That- that’s the thing that will uh, capture people’s attention more. Entertainment’s going to shift more to video games.

Laurie Segall: Do you think it’s all, and do you think that augmented layers we’re all just gonna be in like a giant video game of sorts?

Ev Williams: Yeah, basically.

Laurie Segall: Well, looks like…

Ev Williams: You said to go Black Mirror so.

Laurie Segall: Your kids have a great future ahead.

Ev Williams: Uh, no there- there will still be storytelling. Storytelling is- is not going anywhere, but the um, ethical issue and the issue that I’m most concerned about and we’ve talked about before is- is climate and it’s tangential to most of the things we’re talking about, but on the other hand completely related because I think the- the reason the world has not done enough for climate change so far isn’t because of lack of information or lack of possibilities, it’s because of media manipulation and politics. And by those who it’s not in their interest to do, to do things. So I see that as- as the biggest issue by far that- that we need to- to grapple with and as an, as an ethical issue it’s not clear to me what- what tech does about that, but I worry about it.

Laurie Segall: You did Blogger, Twitter, Medium, you just come up with like a new form of communication Every so often that fundamentally changes things. Will Medium be your final act?

Ev Williams: I think so. I can’t see starting another company from scratch and there’s so much more I want to do with Medium. I do really feel like we’re- we’re scratching the surface and there’s- there’s not really anything it can’t be. Certainly if I were going to start another internet and media thing, I can do all I want to do and all I can imagine within Medium. If I were to start another company, it would probably be totally unrelated.

Laurie Segall: I want to do a quick lightning round. Who would you rather have dinner with Elon Musk or um, Mark Zuckerberg? Who’s at your table?

Ev Williams: Do I have to pick? Can I have them both? I just like them-

Laurie Segall: Do you want them both?

Ev Williams: Sure. I’d love to have them and see what they chat about.

Laurie Segall: The feature that you wish you’d created on Twitter but you didn’t?

Ev Williams: Oh, well you know a silly thing that we should, it’s basically Instagram.

Laurie Segall: What?

Ev Williams: There was a very long time when you couldn’t upload a picture to Twitter.

Laurie Segall: Mm-hmm.

Ev Williams: And then eventually we built it in, but I think we could’ve done everything that Instagram does as a, as a separate separate app or a separate feed or something.

Laurie Segall: Hmm. The media company you’d like to buy since um, you’re, I think you’re a billionaire. You’re a billionaire , and Benioff bought Time. So everyone’s doing it these days in your position, I know you, didn’t you want to, you wanted to buy-

Ev Williams: I don’t think I can answer that.

Laurie Segall: Why not? Stop looking at your PR people. Why not?

Ev Williams: Um, okay.

Laurie Segall: You can answer whatever you want.

Ev Williams: Okay. Disney.

Laurie Segall: Okay. Years ago you told me no regulation would be better than bad regulation, what candidate is best equipped to deal with the nuances of social media issues from tech companies being too profitable from the spread of misinformation?

Ev Williams: I don’t know.

Laurie Segall: Which one’s the worst candidate to deal with it?

Ev Williams: I don’t know.

Laurie Segall: Oh man. So are you not political?

Ev Williams: I’m political when I-I- I haven’t, I don’t want to weigh in on the current uh, democratic candidates. I will certainly get behind one.

Laurie Segall: Uh, do you have a free ride to space or a doomsday scenario like a bunker kind of thing?

Ev Williams: No.

Laurie Segall: I think that’s, no?

Ev Williams: I don’t worry like that. No.

Laurie Segall: Okay.

Ev Williams: We’re all in it together.

Laurie Segall: Um just in general, no that’s not because of coronavirus just in general.

Ev Williams: No.

Laurie Segall: You know I feel like a lot of people in Silicon valley have those.

Ev Williams: I- I don’t have those. I do have… My dad still lives in the farm I grew up in in rural Nebraska, so that’s sort of like could always retreat to there.

Laurie Segall: Okay, some personal questions. When is the last time you felt really uncomfortable besides-

Ev Williams: When you’re asking me questions about politics and Mark Zuckerberg.

Laurie Segall: You know it’s sometimes I think people maybe think because you’re a big founder, you probably don’t really get uncomfortable. Um, but I- I can imagine you get uncomfortable sometimes.

Ev Williams: Absolutely.

Laurie Segall: When?

Ev Williams: Um, I was uncomfortable when you were asking me about being fired from Twitter. I was-

Laurie Segall: It- it still to this day feels sensitive?

Ev Williams: Yeah.

Laurie Segall: Why?

Ev Williams: Uh, it’s embarrassing.

Laurie Segall: Really? Look at all the things you’ve gone and done since.

Ev Williams: It’s uh, I don’t know it’s not a logical thing necessarily.

Laurie Segall: I guess it- it makes sense. It was really public.

Ev Williams: Yeah. Yeah, well no it was sort of, it was one of those euphemisms at the time. Like I’m, spending more time with family, slipping away, but um, yeah I mean talking about failure is uncomfortable for me.

Laurie Segall: Why?

Ev Williams: Um, ’cause I’ve spent I think most of my life trying to succeed.

Laurie Segall: Isn’t failure just part of success? I mean if I could go back to any founder I’ve ever interviewed, the only thing that most of them have in common is a little bit of insanity, a lot of resilience, and the ability to fail over and over again.

Ev Williams: Yeah, you know I don’t feel sensitive about, I fail many things in terms of like here’s an idea that I think would work and it doesn’t work and I’ve gotten much better about embracing being wrong. But that-that- that’s a different thing I feel like.

Laurie Segall: I can imagine that it- it felt, it felt tough.

Ev Williams: All right.

Laurie Segall: Uh, I saw something you wrote you were talking about um, some of the stuff you kind of put you through, yourself through in building a company and you were saying I certainly would’ve uh, would’ve made more progress overall had I gotten more sleep and taken care of myself, but I don’t feel like I could’ve done it any other way given the person I was. I needed total immersion driven out of fear and lack of knowledge.

Ev Williams: Hmm.

Laurie Segall: Um, what were you so afraid of like when building a company? 

Ev Williams: Um, depends on what time I was talking about, but it was, it like in Blogger times where now when laid off my whole team and almost went out of business. I just didn’t see any alternative to that was acceptable. It was a little, it was a lot of pride I think and ego. didn’t want to fail I guess. And I didn’t want to, I didn’t think I was qualified to get any sort of job that I would want. Um, this is during the kind of the dot com bust and so it just seemed like unacceptable to fail.

Laurie Segall: Hmm. You know we talk about um, money and this bubble. You have a lot of money and Silicon Valley’s problem is that to a degree no matter how optimistic you guys are and I know you are an optimist and you’ve claimed to be an optimist. Um, you guys live in a bubble and increasingly it’s smaller. So how do you fix the problems in the world um, that are created by the tech that, much of the tech that you guys have built when the bubble you live in is kind of shrinking?

Ev Williams: Shrinking in terms of what?

Laurie Segall: As in, it’s probably harder I can imagine um, that it’s probably harder for you to understand and grasp the real world when you live in such a bubble and I-

Ev Williams: Yeah.

Laurie Segall: Granted you live in New York. You aren’t as Silicon Valley as many of the founders I know um, you speak a little bit more openly than some of the Silicon Valley founders I know. Um, but it is a bubble.

Ev Williams: Yeah. Yeah I think it’s the biggest thing is just try to be open. I mean I, and that is part of moving to New York and getting different perspectives and talking to people, but I can’t… I think the biggest thing is not, is having people in the company who um, who have different perspectives and really building diversity into the company and- and a culture of listening and then also relates to a, a willingness to be wrong. I think that that exchange, I’m happy to debate things and be wrong and have opinions and that’s something we try to engender in the company. So I think just it’s not “I don’t know everything”. I have to keep reminding myself of that and I’ve, I feel like I know a lot less than I used to think I know. So that’s good.

Laurie Segall: Is it hard to do? I know a lot of people we’ve had on the show so far had talked about it’s harder and harder to speak truth to power in Silicon Valley.

Ev Williams: Hmm.

Laurie Segall: Um, especially in these tech companies where there’s a billion dollar bottom line. It is harder sometimes to go to the top and- and say what’s actually happening. Maybe that’s not the case as much in Medium.

Ev Williams: I don’t know. I mean I’m sure I- I probably can’t say whether that’s hard at Medium or not, but um, it feels like there’s a lot more of that happening in Silicon Valley than- than there used to be, but in terms of people. Well maybe not than there used to be. At Silicon Valley I would say that’s one thing that people underestimate that has always been a really healthy aspect of Silicon Valley companies, certainly compared to rest of corporate America and corporate the world is that there is sort of an attitude of everybody’s smart and has something to contribute and I remember when I was at Google in 2003 and 2004, lots of people at the company was a couple of thousand people and engineers and other people didn’t have any problems standing up at an all hands and calling out Larry or Sergey or Eric on something in front of everyone. And the whole or in email, more likely um, and the do not be evil thing was taken very- very seriously. Um, and now there’s walkouts and- and so I think that- that tension and people’s willingness to do that is- is a good thing and healthy and it keeps uh, founders in check and a big reason that founders are I think not as much in a bubble as they would be is because their employees don’t let them be.

Laurie Segall: Do you believe that the products you’re responsible for will do more good than bad when you look back at history?

Ev Williams: Um, yes I have to believe they will do more good than bad especially the- the one I’m working on now.

Laurie Segall: Cool. How do you want to be known?

Ev Williams: I don’t need to be known.

Laurie Segall: Huh. How would you want your children to view you?

Ev Williams: Um, I would them to view me as- as working very hard to do what I thought was the right thing. That’s it.

I hope you enjoyed getting inside Ev’s brain a bit. Now we’re trying something new this go around. We’re adding show-notes so you can get a bit more context from these conversations. So for that photo we spoke about – my first contact with Ev- back in 2010 – see our show notes. And you can also find a link to the full transcript of this episode. Also let me know what you thought of the episode — I’m trying out this new community number so you can text me and I swear, this actually goes directly to my phone. The number is 917-540-3410, so text me. And here’s a personal request. If you like the show, leave us a review on the Apple Podcast app or wherever you listen to your podcasts, and subscribe so you don’t miss an episode. You can follow me. I am @LaurieSegall on Twitter and Instagram, and the show is @firstcontactpodcast on Instagram, and on Twitter you can find us, we’re @firstcontactpod. 

First Contact is a production of Dot Dot Dot Media, executive produced by Laurie Segall Segall Segall and Derek Dodge, and this episode was produced and edited by Sabine Jansen and Jack Regan, original theme music by Xander Sing.

First Contact with Laurie Segall Segall Segall is a production of Dot Dot Dot Media and iHeart Radio.