Trey Guinn: Around the World and Back to the US

And we are live. Welcome to We Are Cloudflare, everyone. I'm João Tomé. I'm a writer and storyteller of sorts. And here with me, I have Trey Guinn, field technologist at Cloudflare based in San Francisco. I'm based in Lisbon. Welcome, Trey. Howdy. Thanks so much for having me. Good afternoon, I should say to you. Yeah, for me, it's a good afternoon for you. Good morning. Thank you for being here early, because it's early there. Let's jump right in. You're one of the oldest employees at Cloudflare right now. You're celebrating your ninth anniversary. So it was 2013 when you arrived at Cloudflare, right? Yeah. So it's been a little over nine years. Best job I've ever had. And the longest I've ever been in a job. Makes sense. You have like a very interesting story in terms of where you started, where you went from there, New Zealand, Amsterdam. But before we jump into those experiences, let's get to know you a little bit better. So in a sense, for those who don't know you, where did you grow up? What was growing up? It's Texas, right? How was growing up there? Can you give us a sense? Yeah. So I grew up in South Texas, a town called Corpus Christi. You only go there on purpose. It's not on the way to anything. But it was on the Texas coast. And it always surprises people when I say that I grew up on the coast in Texas, because they think that it's just deserts and horses. But so I grew up sailing and surfing. And there's where, I guess, as a kid, my dad bought a 386 when I was 12 years old for the house. And I was constantly taking the thing apart, putting it back together, putting new operating systems on. I think that's where my love of computers began. What computer was that, the first one that you started to deal with? I mean, it was a 386, but custom-built. So you can buy all the parts. And I remember begging and pleading with my dad that it costs about $100 a megabyte for more RAM. So we went from four to eight megs. And it was a big deal. And then going from Windows 3.0 to 3 .1, and we had a TCP stack. And I think Prodigy was my first use of the Internet. It was a lot of fun. That was early 90s, right? In terms of Windows 3.0, it seems early 90s. So it makes sense. So you were, right from the get-go, let's say like that, interested in technology and gadgets and building stuff, in a sense. How did you decide what to study, what to do to go to college, in a sense, too? What was the path there? It's funny. I think I've always enjoyed understanding how things work. And I think that's what has led me to technology, and particularly the side of technology that I work in. So oftentimes, my career was as an infrastructure architect and trying to take the bits of Lego pieces and put them together. And I guess, where did that start? So my dad was a doctor. And when I first went off to university, I thought, my dad was a doctor, I'm going to be a doctor. So I was majoring in biochem. And I had to take some electives. And I took my first programming course in my freshman year of university. And I was like, this is really fun. And I basically just decided to switch and start studying computer science. And I mean, but leading up to that, I guess I was working, I did an on-campus job, like, helping to run the campus network. So that was probably my first job in computer networking. So that was a lot of fun. Yeah. So this was Texas, right? You were still studying there. You weren't going anywhere in terms of leaving the state. The US, yeah. I was in San Antonio, Texas, a university called Trinity. And I started there. And then after I did the campus job my freshman year, my sophomore year, I took a job building NT networks. So I was sort of working on the side of university. And I think it was an interesting thing where I was, you know, you're building sort of, I was small. And so I would run cable in the walls and stuff, but like building NT networks and like learning about, it was like right when I was switching to like 10 base T networks and towards ethernet away from the sort of like those funny T connector networks. And I did that job. That was when I was in San Antonio, then I changed schools and started living in Austin, Texas, and did another job that was similar. Also building sort of like Windows NT networks for small businesses. Did that job while I lived in Austin. And then after that, I moved to New Zealand and ended up doing like an infrastructure architecture job for a software company, New Zealand, which was a blast, but learned a lot about latency. When you live that far away from everything, you really become aware of what's going on, latency. And then that was for about three and a half years. And then I moved to Amsterdam and did sort of like an SRE role. And again, an architecture role for a high availability hosting managed services company. Then I worked at a high frequency trading company that was sort of globally distributed. And then I ended up being an architect at KPMG. Anyway, so these like, these like, the only thing I think about this is that like, there were like, there was no like line you could draw between these jobs. It wasn't like I had some grand vision in mind. But when I got this job at Cloudflare, I was like, oh, I'm now like, I had been working in essentially Internet application delivery and computer networking my whole career. But the thing that like brought it all together was working with customers at Cloudflare. So it was funny that I sort of like inadvertently had lined up all this experience that all came together suddenly for this new job when I became the first solution engineer at Cloudflare. Exactly. The first, because when you started, the company was just starting for people to get a sense. The company was just a few people, like a few dozens, like 40, 40 people, 42 people. When I started, I like, I like to remember that I'm 42nd. I'm not positive if that's the case, but I, you know, of course, 42 is a good number. It is a good number. But before that, I'm curious about New Zealand, because that's a big change in the life of someone just changing to the other side of the planet, in a sense. And again, latency. And recently, I saw some something about that latency in New Zealand and how that evolved. And also Australia. How was it like for you in terms of life there, but also in terms of work, in terms of technology, in terms of doing things there? Yeah. So, well, I guess, first off, like, how did I get there? I was working in this small IT services company. Like we were basically, you know, building computer networks for small businesses in Austin, Texas. And I went on a, I went on a vacation. So two things happened at the same time. I went on a vacation with my mom up to Canada. Our birthdays are near each other. And I met some Irish kids my age, who were on holiday working visas. And I'd never heard of that. And I was like, wait, this is a thing you can, you can travel and work and, and what have you. I'm, you know, I'm like, 24 years old at the time, 23 years old. And I was like, this is, this is something I've never heard of. And then I also came back. And I was in Austin. And I thought, huh, oh, actually, what happened with the company I was working for small, like a six, seven person company, but the owner wanted to basically exit out. And he said, let's do like an employee buyout. It'll be based on seniority. But Trey, you've been here like five years already. So you get like a third of the company, if you'll just stick around for like three or four years. And it was not gonna make me a rich man. But I was like, wow, this is amazing. All I have to do is buy an apartment, find a wife, and I can die, you know, you know, already, like my whole life can be done at 25. And I thought that was maybe not the wisest move. I was like, how do I know I want to spend the rest of my life here if I haven't tried out other places. So those two things, like discovering Holly working visas, and this sort of like decision around do I want to spend the rest of my life kind of where I grew up, made me say thank you so much for the opportunity, I think when I quit my job, sell everything and travel around the world. And when I first got to New Zealand, I thought, you know, I basically, you know, I built computers for, you know, for fun since I was 12. And then like, as a job, since I was like, 15 years old, like in the mall, I was doing, you know, building computers. And I got to New Zealand, I was like, you know what, I'm finally gonna go work in a bar or work in a ski field, I'm gonna do one of these jobs like that everyone else did. And I got to New Zealand and realized that if I got an IT job, I could do a lot more snowboarding. And so it was actually a little easier to support the snowboarding habit. And so I sort of accidentally got a real job in a software company. And it was, it was fantastic. It was a really great experience. A bunch of people in a similar age, and learned a lot about business culture in New Zealand, which I thought was interesting, I think, because it's a very partly just because it's a small population, and the culture is very casual, you can kind of approach anyone, everyone's very helpful. And also businesses tend to be there, they tend to be like substantially less specialized. Because if you're going to be a technology company, so I worked at this company that was a software development house, but I like helped build a data center. And we did a bunch of hosting. And suddenly, like you did a thing that might be seven businesses in the US was one business in New Zealand. But you get to wear a lot of hats. Exactly. You learn a lot doing that. It's interesting, because you you did the different path than Tom Paseka. It was our first guest since I started doing this. And Tom went from Australia to San Francisco to work at Cloudflare. And you were not in New Zealand because of Cloudflare, but you did the different path you were in New Zealand and Amsterdam. I'm curious, in terms of how how do you cut came up in terms of knowing about Cloudflare wanting to work at Cloudflare? Is there a story there? Yeah, well, while I was in Amsterdam, my last job was in Amsterdam was as a enterprise architect for KPMG. And, you know, that was internal KPMG. It's a huge company, you know, it was like 200,000 employees in 140 countries. And I was part of, I guess a lot of people don't realize this, but they're KPMG and the big four, all these, they are cooperatives. So you have like a central group that licenses out the brand. And then you have member firms around the country, around the world. So you have like the US KPMG and the German KPMG and the, you know, the South African one. But there's a central group that licenses the brand up and also sets all these standards. And that central group, which is called KPMG Global, it's about half IT folks. It's actually not very big as a Swiss cooperative. And it's about half IT folks, because what we really had to do was get everyone's technology working together, the member firms technology working together. So my job there was on a 20 person enterprise architecture team. So there's a lot of architecture. And I was responsible for basically standardizing how all the data centers and Internet applications were delivered, also worked on identity management and other things. And in that role, we had this, the KPMG website was a big website offered in lots and lots of languages at the time was hosted on SharePoint, which if you remember how terrible that is, especially like, you know, especially 15 years ago. And it's a funny story. So do you know how translations, like automated translations are done? Most people, you know, I used to think that automated translations were done because this computer got smart enough to understand meaning and then write it in another language. Really, most of it is it's matching. Like if you can just find big bodies of text that are already translated for you, that's what they do. And so they go, there's translation services will go crawl and look for these bodies of text. Well, KPMG website, big website, lots of text in like 20 different languages. And like an early person that was building this service, like early days on AWS with auto-scaling decided to crawl the KPMG website and auto -scale it. So they just crushed the website. Cause you know, they just, you know, they basically sort of dossed the site inadvertently. But at KPMG, they didn't know what was going on, but like, they just saw the website fall down. So they like, you know, failed over from Europe to the US and came up there and then it fell down again. And they're like, we're under attack. What's going on? You know, eventually it was like, let's check the user agent. We called the company said, please stop that. And they stopped. But in the moment I was looking at that problem and I was like, you know, we need like a rate limiter that's like in the cloud that everyone goes through. And I started Googling around and sort of looking for things like that, load balancers, firewalls, rate limiters, but like that would somehow sit in between the user. And I came across this company called CloudClear, which seemed to be essentially the first company in the world to come up with this idea of putting logic, like at the middle of the Internet. And I, at the time I ended up calling up and chatting for like an hour on the phone with Michelle and she was like, yeah, we're not ready for something like KPMG. Cause I think at the time it was like eight people at CloudClear. I talked for like an hour and I was like, and I was super impressed. I mean, with Michelle, obviously, but also with the company and what they were doing. And I became just a total fanboy. So I had my job at KPMG, which I was doing, but every day I was like checking the CloudClear blog, seeing what new things. What are they doing? Yeah, exactly. And, and I just got, I got really excited about it and went home, told my wife, I said, you know what, we need to move to San Francisco. Like, you know, one, it's a little, little too rainy for me in Amsterdam and I want some more sunshine. But two, I was like, you know, I'm a technologist and I really want to be in San Francisco, Silicon Valley, the center of this. And there's this company CloudClear I'm super, super keen on. And so, yeah, we basically moved without having a job, which was, which was interesting. Yeah. Yeah. Sorry. I'll, I'll keep telling this story, but yeah. No, that's a, that's a great story. Again, you, you moved, you did that because you're passionate and you thought, Hey, they're doing something different. They're doing something I want to participate in. That's a good story right there. In terms of your path in the company, you have occupied different roles. Can you guide us a little bit of the roles you have done at the beginning and now as a field technologist? Yeah. So yeah, so I was in Amsterdam, saw this company that was really cool. My wife and I decided we're going to move to San Francisco, did it without having jobs yet. So we literally like packed our stuff up, moved. But I like, I had my eyes, you know, my, I was laser focused. Like I want to go work at CloudClear. So I just kept calling until they eventually put me back on the phone with Michelle. And I said, you know, I've got this idea because I can see that you guys have, you're obviously serving small business, free customers and self-service customers, and you're clearly getting to go up market. And like what you're doing is powerful and you're going to go after like larger customers. And I said, I think you need, I didn't know what it was called, but I think you need a person that can talk to and understand the needs of enterprises and help them adopt this technology. So you need someone who's a technologist, but also comfortable talking to the business, that sort of thing. And do like, well, maybe we're probably going to hire someone like that eventually. And I said, well, I'm in San Francisco. Let's try to arrange an interview, et cetera. And then sort of talked my way into the interview. At the end of the interview, they're like, you know what? I think you've convinced us that this job makes sense, but we're not really sure you're the right guy. And I was like, whoa, this is my job. This is the, like, I'm pitching this job. So I said, well, how about, you know, I didn't have nothing to lose. I was like, how about I come work for free and like audition for a couple of weeks. And luckily they were nice enough to say, yeah, I guess, all right, you know, we'll take some free labor and see what you have to offer. And we can, we will both learn something out of this. Best drive. Yeah. And that job became a solution engineer, a solution engineering, working with our, with our enterprise customers, basically helping them get the most out of Cloudflare. And luckily they let me stick around, started doing that role. So I was technically, I guess, the first hire that was brought in for our like enterprise sales team, our contract sales team. And it was around as we built the, built the sales team up. And then because I was there first and lucky and I guess competent enough, I ended up getting to, to build the SE team. So like that progression at Cloudflare was, I was the first SE. And then we had a handful of SEs and then it was like, okay, well, I guess I'm going to lead that team. And then essentially built that team up to about 160 people in a big global sort of global group. And which of course I had never done any of this before. It was an amazing experience and opportunity. Just doing it. Yeah. Yeah. And, and so I would say that because like, you know, being the, being the one SE is one job and then being the manager of a team of four is a different job and being the manager of a team of 30 is a different job. And then having teams in different, in organizations of different jobs. So I feel like I've had 15 jobs at Cloudflare over the year. And so then last year to sort of finish the story last year, I you know, I came back to talking to Michelle and Chris Merritt, my boss and said, you know, I'm like, I'm really passionate about our technology and helping our customers in real. And I want to be that advisor to help our key customers. And I mean, I love the benefit I'm able to provide as a, as leading solution engineering, but I want to get kind of closer to the customer and close to the technology again. And so sort of talked to JGC as well and said, how about, how about we do this sort of field technologist role where I can work with sort of strategic customers, partners, government agencies and, and help share with them what we've learned at Cloudflare essentially, and try to, try to help them solve their problems as well. So that is how I ended up in the role I'm doing today. So that means you go all around to meet those customers to be there. So you're always traveling, always meeting different people, explaining what we do, helping them in a sense. Yeah. I mean, tomorrow I'm getting on a plane to Canada. I'll be meeting with Canadian government and then some Canadian customers. Last week I was in Los Angeles and, you know, so often and meet with some, some customers down there. I mean, it's a, it is really my dream job that I can be in this role to, to help our customers do better, but specifically as we, as we sort of go up market into larger and larger customers, we have to be able to engage them at different levels. And I'm able to sort of work with like their CISOs and CIOs and just sort of share what we, what we've learned at Cloudflare. I think of it funny, you know, I think back to where I started at Cloudflare, I got so excited because of our blog and how we were, I think it's one of the ways we make the Internet better is that we share a bunch of knowledge. And so I feel like I'm like a human embodiment of like, like carrying the same mantle that of what, what our blog is trying to do. I'm trying to do that just directly with these large customers and governments and other groups. Yeah. Of course. Yeah. That goes to a question that mainly to can you guide us a little bit of, for those who don't know what you think is the Cloudflare, Cloudflare culture, the way Cloudflare usually does things. And also while doing that, can you share with us some of the memories, the favorite memories you had since, since you started? And I'll share my screen with, showing here some of the pictures. Yeah. You know, it's funny. I remember, because I started at Cloudflare, we were small and we were, we were getting bigger. Let's see, what do we have? The actually, if you, yeah, if you pull up maybe like the picture, yeah, this one, beer, one of the, one of the last beer meetings we had in our old office. So this is sort of the whole company when we were still in the office I was in, not the first office, but the second office of Cloudflare in San Francisco. And I love that about beer meeting, where it's that, that sort of curious nature. We really always wanted to share and have, I mean, sort of curiosity and transparency. And so we always talk about what were we, what are we working on and why are we doing this and, and bringing everyone sort of along for the ride. Beer meetings now are, and beer doesn't actually stand for anything. It's just that we say it's not beer at the end of the week. But it brought everyone together. And now of course, and do them virtually all around the world and have people presenting from different offices, still bringing everyone together and sharing with them. And it's still one of my favorite things about Cloudflare is knowing all the cool things that the different teams are working on. And I think it really contributes to your point around like, what is the culture of Cloudflare? I was going to say, I remember when we basically started hiring like HR people and built the HR team and what have you, and we had to like, you know, write down like, what is Cloudflare's culture? And it wasn't that, I don't think it was written down first, like it sort of evolved naturally. And then we just recorded what we had been doing. And that, and that culture was always about, you know, helping this is an altruistic culture, the sort of helping the Internet be better, helping to make the Internet a better place, but also with transparency and curiosity and being really, really principled. And so that's what we say the culture is, but I think pretty unique for me, at least in all the jobs I've worked in, in different companies, this is the one where it most feels like it's not just a saying, let's put it on a wall. Like you really feel like we really do sort of live the values of the company. And the blog is a reflection of that. It's a different type of blog than most corporate blog, for sure. Do you have any story about this wall, posted walls? Yeah, so this was a little bit before my time, but in the first, you know, I think when there were six, seven people at Cloudflare, they had, you know, Michelle ran like actual, like a physical Kanban board, right? So like, what are we working on this week? What's going on? And it was all posted notes. And so it's like, okay, we're going to build speedy support. We got to get our customer support and we're going to get Zendesk set up, you know, et cetera. And they had all the tasks for the week. And then we just physically moved it posted across. And which I thought was very clever. She thought to herself, I should keep these posts and notes. It's like for historical purposes. And so this was when they moved into this office, they took all these posts and notes that were able to cover this entire wall with all the things that had happened early days at Cloudflare. And now all these posts and notes are cut up into little pieces and framed and now hanging in these fancy offices that we have around the world, which is, it's kind of funny. It's like a little bit of history and you can go up and read the different things you were doing or the company was doing when in the very, very early days. We don't have a lot of time, but let me show you this one. It's with Woz. Yeah. One of the co-founders of Apple. Yeah. So this is a whole company, right? This is basically the whole company outside of JGC in London. Exactly. But this was basically the whole company at the time. Woz was working for a storage company, or he was an advisor to a storage company that we were buying high-speed hard drives for, essentially, high-speed storage for our edge nodes. And so because of part of this deal, they're like, hey, we'll bring Woz by and let everyone meet him. But it was such a cool experience. Actually, I'll tell you one other geeky story. When you sign up on Cloudflutter, you're signing a website on Cloudflutter, you have to set, particularly on free or pro, you set your DNS servers to Cloudflutter DNS servers. And they used to be, basically, they were all supposed to be ninjas. There was a whole idea of tech folks that were like ninjas that made everything great. And so you had different names for different DNS servers, and they were all different ninjas. And Lee Holloway, one of the founders, I believe it was his brother, drew all the different ninjas for the different DNS servers. And one of the DNS servers was Woz, woz.ns .cloudflutter.net. And that is a print of the Woz ninja, because he liked to write a segue around. Do you know why I know that? I know that because of the blog. I read a blog post that explains that. I just read it, and it's an old blog post, but I just read it last week, actually. That's a good story there, for sure. Before we go, we have two minutes. Let me ask you in two minutes, main highlights, difficult times, and favorite memories you have from Cloudflutter. I mean, so many to choose from, but I guess one would have been the scrappiness of flying out with Matthew to Washington, D.C., where we had to go swap. We're talking about fixing these hard drives and the edge nodes. We had to go swap a bunch of hard drives in the IAD data center, which we did till like 6 o 'clock in the morning. Talking to SREs who were bringing down traffic and bringing down node at a time. And so here, it's just Matthew and I, we're swapping hard drives. And we finished at like 6.30 in the morning, get back to the hotel, have a quick shower, and then head to the FBI to talk to the FBI about Cloudflutter, who FBI later became a customer because of that meeting. But there was like no sleep, and you're doing everything from swapping hard drives in a data center to pitching a major government agency. So that was definitely a cool story that I will never forget. That's really doing everything in a small company that is growing, but you do everything. That's a really nice story there. Any tips for anyone hoping to join Cloudflutter before we go? You should definitely come work at Cloudflutter. I mean, that's the first one. It's an amazing place. And we always say this internally, but I firmly believe it, which is we are just getting started. Every day I'm talking to customers and people in the industry, and I just realized that we're just at the beginning of a new architecture for how all computing is going to work. And Cloudflutter, it's not guaranteed that we're the company that's going to necessarily dominate this, but I feel like we're the first mover advantage. Almost out of time, and we're out. Thank you, Trey.