Cloudflare TV

We Are Cloudflare

Presented by Andrew Schafer, João Tomé
Originally aired on 

Join host João Tomé to learn about some of the remarkable people behind Cloudflare. On this episode, you'll hear from Andrew Schafer, a member of the Cloudflare team for over 8 years.

Don't miss Andrew's blog post:


Transcript (Beta)

Hello and we're live. Welcome to We Are Cloudflare everyone. I'm João Tomé. I'm a writer and storyteller of sorts and with me I have Andrew Schafer that was at Cloudflare until last week.

Hello Andrew. Hey how you doing? I'm good. I'm in Lisbon right now and you?

I am in San Diego, California. So yeah, so a further distance, so eight hours of difference between us in terms of time zone.

Afternoon for me and late at night for you.

True, true. Let's dig right in. I'm very curious because you had, you are, you stayed at Cloudflare eight years and your path in Cloudflare in a sense was summed up in a very popular blog post where you explain a little bit of your story.

So why not start a little bit of explaining, because I think it's a good story, how you end up at Cloudflare because it wasn't, there was a few tries right in a sense?

Right, sure. So I was a philosophy lecturer at the University of California, Santa Cruz, which is great training for technology because I had, you know, Apple computers from 1982 and, you know, all these types of crappy electronics.

And then I ended up getting into the US Peace Corps, government organization, and I was sent to rural southwest China for two years.

And during that time, I thought I was going to come out and... That was in what year?

What year was that? 2011. So 2011 to 2013, I was in China and I went into the Peace Corps thinking that I was going to use my Peace Corps experience to go into a PhD program and pursue academia and all of that.

But two years in the middle of nowhere, China by myself gave me lots of time to think about my potential future.

And I sat in the private sector and I knew when I came back, I wanted to make a career change into technology in particular because it was the exciting space to be.

So I ended up getting my lecturing post back at UC Santa Cruz on the way back from China, moved to San Francisco and was commuting a few times a week to Santa Cruz.

And then I just, I did 60 informational interviews in 60 days and talked to people from Google and Square and people in construction and project management, all this stuff.

But to do what? Because you were a philosophy major, right?

Yeah. And then, well, that was the question. It was like, well, great. You have all this interesting experience, but what does that have to do with technology?


So I had to through a colleague at the university who knew Matthew from Utah, I ended up getting put in touch with Matthew and I went through all these interviews and talked to him and Michelle and John Graham-Cumming and all these other folks.

And they all said, wow, you're great. We like you. You don't know anything about technology, which is true.

So I ended up, I spent my, you know, I was, I had a lot of time on my hands.

So I learned HTML, CSS, and JavaScript, and I built a website and I hosted a video that I made about my Peace Corps experience.

I put it on Cloudflare and made it Cloudflare colors and wrote a little letter to Matthew and Michelle on the website and then sent it to him.

And basically Borderline harassed Matthew for about four months.

And that was like 2014, right?

The company was still small. So it was a small company. It was very small. I, yeah.

When I joined, I was employee 70. So at that point it was, I don't know, 50 people, like the beginning of 2014, whatever it was.

So anyway, I emailed Matthew a lot.

And at some point he said, all right, hang on. And the next day he sent me an offer letter and I was, I was ecstatic.

I did it. I made this, you know, it took me forever.

It was a lot of, a lot of time and effort and hustle, but yeah, I got in the door of this, you know, really, really weird tech company that wasn't really clear what they did, but I knew it was strange and interesting.

But I'm, I'm curious and hearing you and reading your blog posts, I advise anyone who, who loves this type of thing to read the blog posts and I'll share it in a minute.

But why did you want to enter Cloudflare in a sense, because you weren't tech savvy, you, you know, so the company did something very specific in terms of the Internet.

Why Cloudflare?

What drove you there in a sense? Yeah, well, so I, I was doing all these informational interviews and I was at the Square office and I was at Google and what other tech, I was in some other offices.

They were kind of bigger and just to seem, you know, they're tech companies, but they still seem a bit more corporate and people are, you know, it's a bit more organized and whatever.

And Cloudflare was like, that was the, that was the real deal.

It was like a tech startup, Pilates balls and Ikea desks.

And, you know, it's a room that it was not about the, it was not about the beauty of the room or the coolness of the office.

People were clearly dedicated to a project and doing something, you know, seemed like it was hard and interesting and weird.

It was just, that was it. That was the, you know, that's the whole image of Silicon Valley, right?

The drive to be a part of that, right?

Build something to be a part of that beginning in a sense. And the first time I met Matthew, I was in a room with him and there's a glass room at our first office.

And he said, the people behind me are scary smart. I was like, whoa, what does that even mean?

But yeah, they were, they were, you know, brilliant people building this thing that intrigued me.

He said, you know, I just being thrown into a whole new world is it's pretty exciting.

Absolutely. And you, you entered the company as a writer, right?

So that's a very general title to, to enter a company, especially a tech company as a writer.

So what was that beginning in terms of what did you do?

You learn a lot, of course, that's usual at Colfer, I would say, but what was that beginning like?

You were associated with the marketing team, right? Yeah.

I think technically I started, I reported to Matthew and Michelle, but I guess that was part of the marketing team.

I got the title writer because I, before I got hired, I took a whole bunch of blog posts that were posted and rewrote them, you know, in a better way, quote unquote, than they were written before.

But a lot of it was, you know, the blog was a huge piece of marketing.

So I think Cloudflare spent something like $0 on marketing for the first, I don't even know, seven, eight years of its growth, some, some long time period.

So I did a lot of writing, like for Matthew, for Michelle, for John Graham coming, other engineers that had interesting information to share about DDoS attacks or the technology they were building, and they weren't writers, or they didn't have time to.

So they maybe sketch up some notes or write some stuff and I'd, I'd work, rework it and then publish it for them.

I wrote a bunch of the mark early marketing stuff. And then the, I think the biggest thing I did was all the help menus in the Cloudflare dashboard, we rebuilt a new dashboard.

So I, I went around and interviewed every engineer that built the technology.

And I wrote the help menus, like, what is the technology?

What does it do? At that point, I actually had access to make pull requests.

I was literally making pull requests up to the, up to all the code. It was, you know, that would never happen now.

There's no way they would give me access to that type of stuff now.

But yeah, it was, I did all kinds of stuff. So it was, in a sense, you grew a lot with the company doing different types of things, because always learning, you were writing, you were writing, you had to learn a little bit more of each subject of each thing.

I can relate to that, actually.

But what was it like to then to be in other parts of the company, with the company bigger, even leading teams?

What was that growth like? Sure. So the next thing I did was I moved over to the customer success team.

And I felt like I had a real big advantage, because I knew theoretically what all this technology did, because I had learned about it.

And then when I was interacting with clients who were actually using it, it became way more tangible.

It's one thing to have like a rough idea of what this, like what a web application firewall does, and kind of what it did.

But then when I had clients who were paying us lots of money, who are very stressed out if their site is offline, or they're getting attacked, or whatever, it all becomes really way more real and visceral.

So that was great. I was able to understand the tech and understand my client's needs and what was going on.

Yes, it was interesting. And we did some of the very first upsells. We did an upsell on bandwidth in whatever, 2015.

And someone reached out to me and said, hey, I think our contracts are for renewal.

Do we owe you any more money? I was like, I don't know.

Let me get back to you. I went to this guy named Albert, who built our database, and had him like, run this custom command to pull up their bandwidth.

We didn't even have that metric. Like, yeah, the bandwidth grew, so let's charge her more.

It was just like that. Like, okay, well, you owe us this much more per month.

I'm like, okay. And I signed the contract. That was my first upsell.

It was just, it's amazing to think that that was how it all began, because we were figuring it out as we went.

It was a really special time. Of course. And everything you did, if it was the first time, you would learn things and set what would be that area, in a sense, how it would be built, in a sense, also.

Right. So new guidelines, new things, right?

Yeah, absolutely. We were setting precedents all the time, whether we wanted to or not.

Exactly. That's a good learning curvature there.

Absolutely. And then, so product marketing, customer success engineering, in a sense, also, right?

Yeah. But then you had the special project of building the Cloudflare's China office, right?

Yeah. A few years after I was there, we launched a big partnership with Baidu, the Google of China.

And so our involvement with China got a bit closer.

And Matthew knew I spoke Mandarin. And so at some point, people started suggesting that maybe I move to Beijing to help work on that project when it gets up and running.

But that took a few more years for it to really...

Before the partnership was built enough that having people close to Baidu in Beijing made sense and building out a sales team.

So that wasn't until 2018, yeah, late 2018, that I left for Beijing.

So I relocated to Beijing and worked on that office.

We're doing a lot of hiring. I ended up owning accounts in India and Australia and New Zealand and in China.

And it was it was hard to articulate how bizarre that experience was.

It was incredible. I was on a flight every two weeks.

So I started meeting friends in Beijing. And they try to plan like, going to have drinks or hanging out or this and that.

It's like, oh, yeah, I'll be back in two weeks.

But every week, I will be back in two weeks. I was flying all over Asia, which is also incredible because I had worked with Cloudflare so much around the US.

And then going to a Cloudflare event in Bangalore or in Sydney, Australia, or seeing the same clients that I saw in L.A., I saw them in Taipei and Taiwan.

It was epic. And you can see also, in a sense, first how different the world is, but how global the company could be.

So the Internet is really global.

Everyone needs it. And what Cloudflare does is very important, not only in the US, but even on the other side of the planet.

So although the cultures are different, the people are different, of course, there's a lot of diversity there.

But the Internet is, in a sense, the same, right? Yeah. I think one of the biggest takeaways that I got really early on working with clients at Cloudflare is that Cloudflare is essential infrastructure for any company using it.

It's not like a little marketing widget that if it breaks, we're like, oh, whatever.

If Cloudflare doesn't do what it needs to do, it really impacts an organization, financially and otherwise.

And so that's really exciting, because there's a lot of pressure to perform well.

And also, when I was reaching out to clients, they would respond immediately, because what we were doing for them was so essential.

They wanted to hear what was the update, what was the new product, what's going on, do you want to have a meeting?

It was great in that sense, to be offering a service that was that valuable to people.

It's interesting, because last week I was in our event, Connect, in London, and I was speaking with some clients, customers, some were engineers from other companies, heads of technology in some companies or something like that.

But the interesting thing is how passionate they are from a product that it's not their product, but it makes such a difference that they feel some type of passion for it.

And I think that's really interesting in a sense, because you can see that it's something that makes a difference for their lives, their companies, their day-to-day work.

If they're more efficient, they will be better at their job.

So it makes a difference in a sense.

Yeah, I mean, it might be one step too far, but maybe not. I say that Cloudflare, for a lot of organizations, is mission critical.

It's so key, it's so important.

I heard that type of feedback last week. Of course, Asia has so many different countries, different cultures, from Japan to Australia.

Do you remember any particular interesting story from specific to that region that you want to share in a sense that probably will only happen in that region and not in another?

Oh, yeah. Being in the Singapore office was wild because we had folks from India interacting with folks from Japan and Australia on a daily basis, and people from Malaysia and Singapore and people from Korea.

It was just like so, just like a whole different group of people, so interesting.

My big takeaway, at one point, I owned all of India's accounts, which was really difficult because while I know a lot about China, I've interacted a lot there and studied China deeply and all this stuff, I know very little about India.

I was operating as if they were Americans, but they're not.

They're not interacting with me in the same way.

I was totally out of my league. I just took a lot more time to do the same type of work because I didn't understand culturally what was happening.

I hired this guy out of India.

I remember the first few calls I was on with him, the way he handled situations blew my mind.

He's from India. He understands what they're doing, understands the culture.

I was like, oh my God, you just got something done that would have taken me a week.

You did it in 15 minutes because you know what's going on culturally.

That was really eye-opening. It was super interesting to be a part of all that.

Of course, every culture has a way of doing stuff.

Sometimes the little things matter a lot, in a sense. Also curious and going back a little bit to China, your time with the Peace Corps there, you learned Mandarin.

I think that's pretty awesome. Two years in there and you learned the language.

You were really involved in what you were doing there, right? I was super dedicated.

I also had lots of time in my hands. The Peace Corps, when we first landed, we landed in Chengdu, the capital of Sichuan province.

We spent three months with seven days a week Mandarin language training.

We lived with host families who didn't speak English.

It was all Mandarin all the time, basically learning survival Mandarin.

I was sent out near the border of Tibet in Sichuan province in a small town of 5 million people.

I'm sharing your blog post. Cool. Yeah, some photos here. I had to speak Mandarin.

There wasn't any English. In fact, there wasn't that much Mandarin either because people speak local dialects.

But I was certainly living in Mandarin all the time.

This is the city you lived, right, Ibin? Yeah, this is from the outside.

I was part of this bike club. We used to cycle way outside the city. On the way back, this is looking towards the downtown area on the Yangtze River.

Okay. And this is in the classroom, right?

Your students? Yeah. Classroom. Most of my students were female.

I had two male students. And you were doing lessons in terms of teaching them what in particular?

English. English. Yeah. So that's why you needed the Mandarin to teach them in a sense.

Well, yeah, because their English was pretty good.

They learned English their whole lives, but they had a long way to go.

But for what I learned about Chinese culture is that they were really, really hesitant to make mistakes.

They really didn't want to lose face that way.

So it helped to have me as the teacher use Mandarin and make all kinds of mistakes.

They're laughing at me. I'd say silly things. I didn't know the right words sometimes.

And they thought it was hilarious because I was speaking to them like a third grader or something.

And I think that made them more comfortable. Like seeing me being silly and foolish with my language skills and trying to learn helped them feel more comfortable using English because, yeah, you've got to make mistakes to learn.

Failure is a resource. And with language, man, you're going to fail all the time, which is wonderful because then you can learn faster.

Here's some memorabilia, your card as a writer back in 2014. That was it. When I first joined Cloudflare, Matthew said the company had, it was like a flat structure where there was no hierarchy at all.

There wasn't a need for it then. So the titles were extremely minimal, like engineer, writer, whatever, marketing.

So that's my title, actually, content writer.

Yep. That's it. Eli, the computer guy here.

That guy's amazing. Hilarious. I knew so little about technology that I spent hours and hours watching all of his videos on the iOS.

I'm drawing a blank on it now.

Which way? OSI model and networking and what DNS is, just like all the fundamentals because he breaks it down these really simple ways.

He's great. John Graham-Cumming used to walk by my desk and comment like, what are you doing with this orange guy on your screen all day?

I was like, I am learning so much from this guy. It's like the Mr.

Rogers of computing. True. And sometimes it's not easy to learn when you're speaking with very experienced engineers.

I have a sense also. So you must dig in more on what can help you to understand some of the layers.

Although now I think we explain a lot better in terms of onboarding and all that.

Probably at the time it was different.

No, my onboarding was reading Cloudflare's blog from blog number one through the current blog.

That was part of my onboarding. I didn't do that because there were so many, but I definitely read dozens of blog posts.

Yeah. Yeah. It's helpful. It's a whole textbook. And then you tried to do code and do more and more stuff regarding that, right?

Yeah. I basically, we have our solutions engineers have a homework assignment they give to candidates.

And so I just completed that assignment, which it's pretty technical.

It's not, you know, it's not, for me, it was pretty technical.

I think for a lot of folks, it's not that difficult, but it involves standing up a web server and putting Cloudflare in front of it and doing these things like, you know, hosting something on the web server.

It was great.

I learned so much by doing things hands-on. I just, that's, that to me was such an exciting part of working at Cloudflare because I didn't know that much about any of this stuff.

I was really curious. And so I got into the command line, learned a bunch of command line tools, and I could go ask all the engineers in the building how to do things.

If I got stuck, it was fantastic. It was super interesting.

You must explain us your big horse award for strong words. Sorry.

And here it is the award. So basically a good friend of mine at the company one day, like said something like, Hey, big horse, want to go get a cup of coffee?

I don't know, whatever it was, like something silly like that. And I thought it was hilarious.

And I made a friend of me, I was like goofing around and I Googled like stupid horse drawings.

I just like put that Google query and that's the image that came up that, that big horse thing that, you know, first grader drew came up.

I just wrote strong work above it. And we, so the, the CSM team had some sort of segment where we were supposed to present something for beer meeting.

It was like a big deal for, I can't remember why. And I was just being goofy.

I was like, Oh, Oh, we should order a, a big horse trophy and give it out to a support member because the CSAP team does so much work that no one sees.

Like we should honor them with a big horse award.

And I was like, Oh, that sounds completely stupid.

But I lobbied it. It's like, no, we got to do this. And I, I got the trophy.

I ordered it. It's like, look at this thing. It's gorgeous. And then at your meeting, it was like an employee of the month award type thing, which, you know, that doesn't scale, but it became a thing where it was hilarious.

And so we had these big horse trophies and then we started shipping them out to London and Singapore for people who are doing, you know, like if they got some sort of recognition for completing, you know, a project or whatever.

And then we made these stickers.

So people had, uh, big horse stickers on their last class. Well, those are all the renditions that I made some of them.

And also other team members made a bunch of these.

It was hilarious. Usually Friday afternoons at like three o 'clock, these got created, you know, makes sense.

It's all about brainstorming and sometimes weird brainstorming gives us more human ideas.

And this is a very human idea, I would say.

And it has a good heart because it's, it's trying to, to give a merit to someone in a sense.

Yeah. The whole thing was just trying to, it was just a silly way to, uh, give people credit.

Like, Hey, you, you're doing an amazing job.

Uh, we want to reward you, like, you know, and just like create, just like telling them they're doing good work.

I think that goes a long way. If you, if you are honest and sincere with saying, Hey, I think you're doing excellent, excellent work here that people receive that.

And this is just, I do that all the time.

But we still have five minutes. I'm very curious to learn more in stories. You told me one, uh, recently regarding, uh, rail gun, uh, the, the technology that John Graham coming did, and that has, uh, a type of nerf guns, uh, related story, right?

Yeah, that's. So I think this, this shows, uh, the time period of Cloudflare when I joined.

So I think it was the first or second week I was there. Uh, Matthew, Michelle and other folks were going to some sort of conference and we had this technology called rail gun that I can explain.

It just, it sends the diffs of a website.

So it's saying the whole image that waits faster and lighter. Uh, any who, what they were doing as a marketing tool was they had bought all these nerf guns that shot discs and they ordered rail gun stickers.

They had cloud, the Cloudflare logo on them and they put the rail gun stickers on the guns.

And then I sat after work next to Matthew and Michelle with some other people.

And we were just sticking rail gun stickers on these little discs so that during the conference they could shoot them out.

It was amazing, but it was, yeah, it was great, you know, it was whatever six o 'clock and we were sitting around and chatting, but that's, it was a tiny company, you know, it was just, and they were figuring things out.

It was, it was amazing. Absolutely. Uh, even, even in terms of, uh, a lot of products, you you've seen the birth of many products of Cloudflare.

Do you have a favorite one or? Oh yeah, Argo, a hundred percent Argo. Why?

Because Rustem launched it and I was the first one to sell it. And I had this company that had this application and they were expanding into India and, um, Brazil.

And when we turned on Argo and we saw the differences, it improved the speed, uh, of the load of their application by like 75 or 80%.

It was incredible in those areas because like the further away it was from the origin server, the more chance it had to, uh, smart route the traffic.

It was, it was amazing. It was so exciting because it was the first like big product that I got to experience, like really added huge value.

It was a slam dunk, uh, to, to have the people procure it. It's like, Hey, would you like your traffic to be 80% faster in your target market?

Of course they would.

So it was so win-win. It was like the best sales motion ever was a part of, cause it was just like high fives all around.

You're happy to pay us. We're happy to render the service.

It was great. It was, it was super exciting and fun. Uh, and you know, again, we, like I had to submit a JIRA ticket to get the graph to understand how the percentages were and all this and that.

And you know, it was like, it was sort of half baked at time.

Uh, but yeah, the company, uh, got it and it worked really well for them.

And it was, it was super fun. That was, we took a trip to LA for it.

It was really fun. So this is the blog post from 2017 about Argo.

I also have here the famous railgun. And John explained to me that the 2404 is the port here in the gun is the port that is used in with railgun service.

Uh, so those types of details are what make Cloudflare's blog really interesting to people.

Cause like, you know, those people who know, no, like I didn't know that, but engineers would know that.

And they noticed that like those types of technical details.

So interesting. We have one more, a little bit over than one minute. Do you have any advice to someone that wants to join Cloudflare that would do also some of your peer review?

Oh, sure. It'd be the same advice I would give to anyone joining any company, but at Cloudflare, it's especially important.

Learn what the company does.

It's like, it's, it'll take your time. It'll be difficult, but if you actually understand the technology and the value it brings to the table, the conversations you're going to have with people internally are going to go so much smoother.

I think engineers do this by default. If you're on the business side of things, do the research, like really understand what Cloudflare does, or at least the biggest picture of what Cloudflare does.

It'll make all the difference.

Cause then you really know what this is about, the power of it and why it's so valuable.

And I think that just helps people realize like, okay, this, this person gets it.

They, they, you know, they know what we're doing. They want to be on board.

Okay. Let's talk further. Do you have a word or an expression to summarize your period, eight years at Cloudflare?

Diligence overcomes all.

That's a good one. So thank you so much, Henry. Hope you like it and good luck for your new adventures.

Okay. Thank you so much. It's been amazing. Thank you. Bye.

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We Are Cloudflare
Meet all the people who make up the Cloudflare team from all offices, all teams, all levels, in as many languages as possible.
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