Jerome Chen: 11 years at Cloudflare (and counting)

Hello everyone and welcome to We Are Cloudflare. I'm João Tomé, storyteller at your service and with me I have Jerome Chen, web engineers at Cloudflare based in San Francisco. I'm based in Lisbon, Portugal and that's why I have this virtual background. Lisbon is not that pretty at this time of year. Hello Jerome, welcome. Hi, how's it going? Good. Let's just jump right into our conversation. First, congratulations on being at Cloudflare for 11 years, actually more than 11 years now because it was December 2011, right? Yes, it was. First, I want to have a perspective on who is Jerome. So, where did you grow up and what was it like growing up where you grew up? So, I actually moved around a lot as a child. So, you would never notice that I was born in New Jersey and I don't remember a whole lot of New Jersey. My family moved away when I was like one, basically. And then the first few memories that I can think of is where we moved to Houston, Texas or actually a suburb of Houston, Texas. Weirdly named Sugarland. It turned out that that city had a sugar refinery, so I guess it made sense. But we spent a few years there and then my dad, his job moved to basically Southern California and so we spent some time in Yorba Linda and then we moved back to Sugarland afterward. And then right in the middle of high school, I moved to Pleasanton, California, Northern California. And that's where I finished high school and I went to college in Irvine. So, I've been all over the place. Yeah, and especially in California, right? All over the place. But California is mostly the place you have been. South and North. Yeah, most recently Northern California. Right after college, I basically got a contracting gig at Google and that's kind of where my current tech career started off, basically. Before we go there, when did you start to be interested in technology? Was that early age or not really? I remember it was a 386 computer. Right when I was three years old, my dad kind of taught me the basic commands of MS-DOS specifically so I could play video games. So, I feel like everyone starts out this way. So, the 80s, right? Yeah, pretty much. Yeah, I guess 1989. Late. Yeah, but that's how I got involved, really. But I would say I kind of kept up with technology, at least on some rudimentary level. Clearly, I wasn't at any genius level like some of our colleagues, but what is it? It's usually video games that kind of kept me in the whole technology space and that kind of thing. And so, whenever I got a chance to play with something, I would. And I kind of stumbled into the rest of it. But in terms of when you had a decision where you thought, oh, this technology thing or Internet thing is really engaging, I want to work there. Was when you had to decide what to study or where to go in terms of career? It's not that my parents. They wanted me to be a doctor. And at some point in the middle of college, I kind of decided like, this is not what I'm good at. Oh, you were studying to be a doctor at that time in college, right? Well, yeah. So, basically, I entered the program or entered college with a math degree, basically. And my parents were kind of at the beginning, were kind of like saying, hey, we should start thinking about transferring credits over to a pre-med sort of degree. And I'm just kind of like, no, that's not what I'm good at. So, I happened to be actually okay at computer science and programming. So, I was just like, why should I do that? So, I figured the thing is, I felt that the computer science program, which was good in college, that I didn't feel like it was going to be really that interested in the coursework. So, I stuck with my math degree in pure mathematics while still coding stuff on the side. And in college, I was also an IT guy, so I was fixing computers and that kind of thing. So, it was a great way to make some money while in school. So, yeah, that's how I kind of fell into it. Already in college, in that sense. Yeah, basically. So, my life was so tied to just technology because you had, those friends were just kind of like, hey, can you fix my computer? And when you're in college, you'll do a few things for just as a favor, or maybe you'll make some money in the process so you can eat the next week, that kind of thing. Of course, make some bucks, extra bucks, yeah. Yeah. But then when were you thinking, oh my God, I can have a career here? You had a proposition, what happened there? Like in Cloudflare specifically, or just like... No, no, no, no. In terms of from college to start working in the area, really. So, basically, I graduated college and I was still working the IT job at... Which college was it? University of California, Irvine. So, there was basically a research institute, Beckman Laser Institute, that I spent the end of my college years and the first post-college year or post-grad year, I guess. I mean, I didn't pursue a post -graduate degree, but I was working at this lab. And the thing is, I wanted to do more than just the computers that we were fixing and that kind of thing. I was looking for something bigger or just more things that I could learn, basically. And so, I got lucky at some point where... The funny thing is, I applied for a position, like a contract position on Craigslist to come back to the Bay Area. And if you remember the company Palm... Yeah. So, I was going to do... Had a tablet, a small tablet, right? Yeah. Yeah, the tablets. Yeah. And I think they got acquired by HP or something like that. It's been a long time since I've thought about this. And basically, I applied for a contract gig and they were going to roll out Windows 7 or something like that for their environment. And it was supposed to be a three-month gig and it was just going to get myself into the door in the Bay Area, like texting. Turns out, I never showed up for the first day because I think the week before I was supposed to start, I got another contracting recruiter and saying, hey, so we've got this gig at Google. Do you want to take that? Do you want to take this contract gig at Google? And it's like, oh, yeah. Okay. Yeah, sure. And so, how long is the contract and everything? And it turned out to be indefinite. Ultimately, it ended up being about 11 months. What were you doing at Google at that time? So, as a tech staff administrator, basically, kind of like the company-wide IT group, in a way. And so, we were the front line of basically this front line to fix computers or devices and stuff like that internally at Google, basically. So, if something went wrong, we were the first people to talk to. So, we did a lot. That was around what year? I want to say 2010. What was next for you in terms of career path? It was a learning curve, right? Yeah, it was a little bit of a learning curve. But then, I had a friend refer me to what... It was kind of like a similar situation, but I ended up at Apple afterward. So, it was still a contract position. And I spent almost a year there, too. And it was kind of an interesting thing. It was a similar thing. It was a system administrator. It was IT stuff. But we were kind of like an adjacent group to the... What is it? Mechanical design portion of Apple. So, I got to see... And under NDA, of course. I got to see a lot of the products get built. So, the last thing I saw was the iPad 2 launch, and the iPhone 4S, and that kind of thing. And so, being kind of adjacent to it was actually kind of a really cool thing, because it's just like you got to see the discussions and stuff like that of how they put parts together. Some of the things were in terms of durability, they actually had desktops dedicated to drop testing and that kind of thing. And we had to be in the middle of all of that just to kind of manage those computers and that kind of thing. It was history in the making, right? And you were close, because of course, the launch of the iPad. I think it was the last launch Steve Jobs made on stage. Yeah, he passed away. Yeah, Steve Jobs passed away right before I left that job. And the funny thing is, there are a lot of the rumors around Steve Jobs. Like you don't talk to him, that kind of thing. And I mean, the one time that I saw him in Cafe Max, I was scared, I ran. Because of the rumors of what he usually did. Yeah. And so, I didn't want to be noticed. But yeah. But I mean, I learned a lot during that time but what kind of ultimately ended up was that obviously, I was a contractor and I was looking to get converted into Apple corporate and actually have a be an actual employee. But time went on and there was no real movement in that. Then came Cloudflare, right? Actually, before that, let's talk about the party you went where you were not an employee, but you were at the Cloudflare party, right? Oh, yeah. Well, so basically, what happened was that two of my friends, they were from high school in Pleasanton. Two of my friends were working earlier than me. Basically, they invited me to this, they had just moved into the 665 3rd Street loft. And so, they were just like, hey, well, we're having this party, do you want to come by and check it out? And I'm like, well, I mean, why not? We'll see. This should be interesting. And they were two of my closest friends because we had worked together on projects in high school. So, just like, okay, we'll see what you're up to. And so, I went to this loft party and ended up hanging out. I had a good time. And they kind of pulled me into this photo that you see. Not sure why. There's more dedicated photos here. Yeah. And so, and the company was so small then. I got pulled into this and not knowing that I was going to be joining the company a few months later. And so, that I... So, here and here, and it's like, here's the team, call for a team, and there are you, not a member of the call for a team at that time, but present in the photo. Do you know if any of the others were not all, if there was any other person that was not a employee in the photo by some reason? Well, okay. Some of these people are significant others. So, you can see Michelle's husband. What is it? There's Jason's wife. And then the rest of the people don't work here anymore. It's more than 10 years. So, this is November or October 2011, something like that. The blog post is from December, I think. Yeah. It was a few months, I think, before I actually officially applied and interviewed. It was kind of wild because I was like, am I supposed to even be here? That kind of thing. But I was just like, I just went with it. It was fine. Not knowing that that would be my office later in that year. So, it was kind of, I don't know, a little bit surreal to talk about from here because there's the old logo with the capital F and everything was just kind of like the old school t-shirts. I had visited them before in the Palo Alto office when there were just like six people and that kind of thing. That was wild. I'm sure Matthew can talk a lot about the fun challenges of being in those first days. But I knew where they were and I had known Chris, who was already working there at the time, know it was going to get bigger in this case. The company was small enough where it felt like a fun science project still. But at the same time, we didn't know it was going to blow up in this way. Maybe Matthew and Michelle knew, but we didn't know. But yeah, more than 10 years after. First, I want to learn a bit of what you do right now at FallFlare and what did you start doing when you joined the company and how your work evolved? Currently, I think we're still working on the team name because we're working on basically our original team split. We were originally the core metal team and what we did was we provisioned basically servers for the core and various tasks around that. And we're responsible for an internal system called Zinc. But when I joined Cloudflare, interestingly enough... So now you're a web engineer. In terms of position, what you do is web engineering, right? So the funny thing about the web engineer title is it hasn't changed even though my role has changed. I know the feeling. Yeah. It'll make sense when I tell the story. But the funny thing is no one ever bothered to change the title and I never pushed. Basically, I joined Cloudflare as a support engineer. So at the time, it was kind of like me, Justin, Payne, and then a few other people who were just kind of manning the support queue. It was incredibly tiny in comparison. The funny thing is that I originally applied to be an SRE because I felt like I was good enough at that time, but definitely I was not. So looking back, I was just not ready. I joined Cloudflare as a support engineer. So this was December 2011, right? Yeah, December 2011. And as I was kind of just getting to know the ropes in the next year, I was... Oh, and Cloudflare was like 20 people at the time? How many? So yeah, I was the 21st hire. So yeah, 20 to 22. But a fun fact is just that I think JDC might have already mentioned this, but we started technically on the same day. December the 5th, yeah. Yeah. And he, I think, accepted first because I think Matthew gave him the offer first, but I was the first one in the San Francisco office that I know of. So which one of us is actually first is still up for debate. But I think 11 years later, we're just like, same day, whatever, at the same time. But yeah, it would be funny because JDC over the years would visit and be like, hey, hello, my nemesis. So this is John Graham-Cumming, our CTO, that joined at the same time, just for people to understand. And he was working at the time from London. He was the only employee not in the US at the time. Yes. Yeah. So that's one of those fun little things that we hang on to over the years. Yeah. So how evolved after that? How evolved what you did and how what you did was connected to the company being bigger and also having more customers, all that? Like over the months, I was asked to help out with partnerships for a little while. And it was it's not like the partnerships that we know of today. We establish a lot of partnerships with hosting providers and that and getting ourselves integrated into various web hosting systems or just integrate into like the dashboards of hosting systems. Not only was I was helping hosting providers on board to that, I had basically a little bit of help or a little bit of time working on the integrations themselves. Integrations of what specifically? Like the integrations into the hosting platforms, basically. And basically, the idea was at the time, just kind of like distributing Cloudflare as much as we can and exposing the idea of Cloudflare for like anybody who's running a website, that kind of thing at the time. And so we were trying to make it as easy as possible to have very few clicks and having Cloudflare on your website with very little setup, basically. And so we established a lot of relationships with hosting providers and that kind of thing. And I got to be part of that. And there are photos of this, but I got taken to hosting con and different conventions that are hosting related, which I didn't even know existed until I got there. And so, and we were, I was kind of like part of all that in between doing support as well. And then... You were juggling. The company had so little employees, it was so small that you had to juggle things. Everyone has to do everything, right? In a sense. Yeah. Yeah. That's interesting. And yeah. And I mean, I think it's like the classic startup life, you know, it's just like a lot of people end up being, you know, wearing multiple hats. And I ended up acquiring a third one in the form of we had Dean, I think one of our first sales guys, say, hey, we need somebody like just technical to help me out with this call with like a larger customer. This was like at the time where I think enterprise in business was just kind of being started. And he asked me if I wanted to join. I'm like, okay, we'll see if I can help. We'll see what happens. And so it turned out I was doing Trey's job before he got hired. Trey Gwin. Actually, I spoke with Trey a few months ago here in this segment. Yeah. So basically, like when Trey interviewed, at some point, Michelle was just like, okay, you're doing too much. So I need you to like choose which way you want to go. And then Trey ended up taking over for me for that quasi solutions engineer thing at the beginning. And then I would continue to do like partnerships. And because partnerships ended up being like super close to the call for API, I ended up starting to work on that too. And that's where I where I got my web engineer title and never left. So on the API. Yeah. Yeah. So yeah, in terms of those more favorite, also challenging moments, working at Cloudflare, which ones you you would highlight in a sense? Well, the thing is, like, a lot of those things ended up, like, I spent the most time on what was called the WW team at the time, but like, has since splintered off into different teams. Most recently was the API team that was working on a lot of my focus. And basically, there was something about like, I mean, okay, so I worked on a lot of the API endpoints and code there. But what I ended up focusing on at some point was just kind of the uptime, the reliability of Cloudflare's API, which like, maybe doesn't get a lot of attention. But the thing is, people are using it and are, you know, what, because we're a Cloudflare, our own API has to be up, right. And so a lot of the challenges were basically, every time, every time we started growing in terms of usage and stuff like that, we had to make changes so that we could handle more load in that, in that area. So the API, the API itself, and going from like, what, what was like a simple, like few servers on Apache, ended up going into like Nginx with PHP, FPM, and then evolving it and like moving that whole thing into Kubernetes and that kind of thing. So the challenges kept, kept coming, because we kept on growing. And like keeping up, keeping up with that was, I mean, there's no one thing that I can point to, but it was like, it's, it was a series of things that built up over time, basically. And then it turned into what we have now. Exactly. Finding the right hardware, the right procedures of growing, growing, constantly growing, right. Those are challenging situations. In terms of favorite moments, possibly you had like moments in data centers. Those who were at the company in the beginning usually have any, some sort of story in a data center or something, or other stories, favorite stories you want to share? So the one data center story that I, that I've got was that because like, as you know, we've like, I was in partnerships earlier. We, I had to visit Seattle for, for a thing. And our SREs were just kind of like, Hey, can you install some more RAM in the Seattle data center? I'm like, okay, perfect. Sure. I'll do that. Just get me the clearance and stuff like that. And we wanted to do some, some sort of out of band, like communication early in Seattle. And so they gave me this little console server that had a SIM card in it. So you can connect to it out of band. That's not like in case the data center was actually down. And so basically I had to put a SIM card into a console, a console server, and for whatever reason it got stuck. And so, and it was kind of like a freak accident in a way. And the normal interaction for it was for whatever reason broken. And so I thought, but the thing is, it was properly inserted at the time. It looked like it was properly inserted at the time and the console server would just not work with a SIM card. So it was just straight up broken. And I was terrified because I thought I had broke it. So, but I, in order to get the SIM card back out, I had to take a, like a dental floss pick and forceps to like extract the, to extract the SIM card. And, and like, basically I told our networking team, just like, okay, this happened. I don't know how or why, but like this happened, but I'll get the rest of the stuff done in Seattle. So, yeah, scary, but. Scary, scary moment. And it was like your first time and then something went wrong. So those moments are scary for sure, right? Yeah. So, but we got through it. I think the data center is still there, so. But in terms of other moments, you want to highlight favorite moments at the company, any fun stuff that happened? Not that scary. Well, I mean, I guess I have to talk about like the IPO. We got, I got to go to New York and like see all that. 2019. Because, yeah, 2019. Like the thing is, I didn't know, it was like, I mean, we, like at some point it would, there were, there were rumors that it was going to happen, but then we, we knew that then they kind of like announced it internally and that, that kind of thing. I don't know if I'm supposed to say that, but I guess it's all after the fact now. Always announced internally first, right? Yeah. Yeah. But it's like, in terms of the timeline, anything, but I, I, I mean, because I had been around a long time, I was, I had a very high chance of going, but it was kind of like a surreal thing. Cause I always thought like the New York Stock Exchange, what was just kind of like a fake place in a way you just see it on, see it on TV and just like, okay, that's what, that's what the stock market looks like or a stock market looks like. And then being on the floor, I was just like, okay, well it's smaller than I thought, but this is actually kind of like interesting. I think I lost you there. I just lost you there of the reaction, of the reaction. Can you repeat the reaction? Oh, okay. Oh no. It's for, for me, it was just like, I, I got to the, the floor of New York, New York Stock Exchange. And it was, it was just kind of, I don't know, it's, it's surreal in the sense that you only see it on, I would only see it on TV. And I didn't think it was an actual, it was an actual real place until I was there. And part of it was I was just like, this is a real place. I guess it's, it's actually smaller than I expected. I don't know what I was thinking. So it seems like a movie studio of some sort. Yeah, it felt like that in a way. It was just like, did they just set this up for us? That kind of thing. I don't know. It's just that, like, you see enough of the news where you, you think it's like, it's way bigger than, than it really is and that kind of thing. But I don't know. It was, it was kind of like, I feel like one of those once in a lifetime things that you get to do is like, you get to watch the company that you've been working at go public. And you get that. And before COVID, like, you got to like, hang out on the floor and that kind of thing. So I, it was, it was kind of a, that, that was kind of a wild ride for me. So special moment there. Yeah, it was definitely a special moment. So I, it took me a while to understand that, like, it was that transition from, we were kind of like the startup and I, I always knew we were the startup and then transitioning into a public company and just kind of like adjusting to that mindset, that kind of thing. So, but yeah, that's interesting. And I'm curious first, just to wrap things up, two things. One, what do you love the most in terms of doing your job? Like what do you love the most? And the second is what is the main thing about Cloudflare that most people don't realize that they should? In all my positions anyway, I always felt that the, the thing that I come back to in terms of like what I'm doing at Cloudflare is the, even though it's not like visibly, always visible on a blog post or anything, it's just the amount of impact or the, the preventative stuff that I've done over the years where things could have been way worse. Or, I mean, of course accidents happen and that, that's fine. But the, the fact that we can come back to it and like just still carry on is something that I thought was important to me. And so like the amount of impact of, of, on like just people and the Internet in general, general is a scary thing. But the thing is, it's just like, I got to be a part of it. That was something that I was looking for when I, when joining, because it was one thing to be like just kind of like a siloed engineer at Apple and Google and transitioning to like being into like a very significant part of the team at the beginning and also, you know, throughout the years. The, the big thing that for, with Cloudflare, I'm sorry, what was the question again? That second question. No, no, no. It's what's the main thing about Cloudflare that most people don't realize, but they should. I feel like we've done a lot of good in alleviating some, some of that over the years, because like there were a lot of misconceptions early on, where like there were a lot of sort of conspiracies, I guess, that we get ourselves into. I think we've done a good job like over the years of debunking. I feel like we've, we're so transparent as a company. Like there are definitely like assumptions that people will make, but there are like assumptions that they would, that people would make about what is it, companies in general. So it's a hard question for me to answer. Of course, of course. Actually, you already, I think you answered a bit in your previous answer, actually, because in a sense you just explained how Cloudflare has like a real world impact on the Internet, like avoiding attacks, avoiding things. That's also a good perspective there. There, there are a lot of things that like we run or like are a part of that we don't like talk about, but, but I think how we recently did the, nevermind, I don't know I can talk about it. The impact reports? Yeah, the impact reports, the things that we, the, some of the things that it's like fed rampant, that kind of thing. But yeah, I don't know, like we've accomplished a lot in 11 years. So it's been a wild ride. What would be your advice to anyone that is thinking of joining Cloudflare? Do you have like advice? Why should they consider or think about Cloudflare and how could they like be better and make it better in terms of joining the company? Over the years in Cloudflare, and I think it's just something that we talk about all the time, being curious about like just how the Internet works and that kind of thing will get you a long way. If it's anything that I've learned over the years, it's like, I don't really like, I know stuff, but I don't know everything. So, and that's something that I continue to have, like, or continue to realize when I'm at Cloudflare. So like be prepared to learn or actually want to learn. Be curious about the like technology around you and the emerging technology that comes out like on the Internet, because it's like, especially now the Internet's kind of like an evolving place. So if you're ready for like the sort of ride that you're I feel like the proper mindset to like continue at Cloudflare or work at Cloudflare and that kind of thing. It's, and granted, I've been here for 11 years, but it's really not like anything else, it feels like so. Thank you. That's a wrap.