Cloudflare TV

Dial Up Motive

Presented by Dan Hollinger, John Engates
Originally aired on 

Human-interest segment asking Cloudflare employees what their first Internet experience was and how it informed them joining Cloudflare. Dial-up modems, bulletin boards, punch-cards, Twitch, Twitter and more.


Transcript (Beta)

Hello. Hello. Welcome everyone to episode 28 of Dial Up Motive.

On the show, we explore the early Internet experiences of Cloudflare employees and how it shaped their lives, their careers, and ultimately how they made it to Cloudflare.

I'm your host, Dan Hollinger.

I'm dialing in from the Bavarian coast. And on with me today, we have John Engates, Field CTO at Cloudflare.

John, thank you for taking the time.

Hey, Dan, good morning.

Good afternoon, whatever the time zone is where you are, but pleased to be here.

Thanks for having me on the show today.

I try to cast a wide net when it comes to time zone because even if folks aren't catching us live, there's one of the recordings and who knows when or how people prefer to listen to this.

So yeah, always good to aim wide in our global culture.

Got caught up on that a couple of times.

I've done some meetings and said Good morning and everybody looked at me like, What are you talking about?

Anyway... Well, and I assume, you know, as part of your role as Field CTO, the global nature of your calls and your meetings comes into play almost daily.

Yeah, it does.

So a field CTO is an external-facing role, primarily customer-facing. We talk to partners around the world, we talked to industry analysts, people that are sort of interested in Cloudflare from an outsider perspective, and oftentimes it is sort of global in nature because customers are now everywhere.

Cloudflare is global in its product breadth and depth, and so the customers tend to be everywhere as well.

And time zones don't matter much on Zoom calls.

People just jump on when they can.

And so, yeah, I've been on some calls lately with folks from all over the world.

And, you know, we talk about all kinds of topics.

You know, mostly it's how customers are leveraging Cloudflare, how other customers are using us to solve a particular problem, whether it be on the Web or on their own internal network.

We've been talking a lot about Zero Trust lately.

You know, the topic lately has been around a lot of the how to prepare for potential cyber threats in context of the war that's going on in the Ukraine region.

And so a lot of people are worried about that.

They're nervous and they're asking questions about how do we bolster our security?

And those are a lot of the kinds of conversations I've been having lately.

And how would you say a field CTO differs from a CTO in kind of a normal capacity?

Are you jumping on the plane more?

What's kind of the the work distribution there?

That's a good question.

I have been a CTO for many years and I've done it in multiple companies.

And so my first CTO role was at Rackspace. It was a partner of Cloudflare.

So, at that role, my early days of CTO, it was very much internal focused and I was building the products and helping guide the solutions that we were delivering to customers and really spending time on the what we were building and what we were selling kind of aspect of it.

And then in the latter part of my career there at Rackspace, it sort of shifted.

As cloud computing came into the picture, I spent much more time externally telling people about what cloud was, what it was going to mean, how it was going to evolve, or my predictions on that.

And so in my experience, CTO can very much be an internal-focused, product development engineering kind of a role, or it can be very, very much the reverse, which is external-facing and trying to shape and guide customers on the market to the right solutions or the right outcomes in terms of their uptake of the products.

I also, you just asked the question about travel.

I used to joke that CTO stood for Chief Travel Officer because I basically spent a lot of years on the airplane.

So far at Cloudflare, I've been here about six months so far, and have not traveled for Cloudflare yet, so I feel a little bit like that CTO, Chief Travel Officer is a bit of a lie in this role because so far it's all been Zoom sessions or online, but it's about to change.

We're planning some conferences and events and I've been invited to do some dinners and spend some time with customers sort of in the different parts of the world where they are.

So I think it's about to pick up big time. Yeah, it's been chief telemarketing officer or telemeeting officer.

Zoom Call Talking Officer.

Chief talking...

yeah, that one works too. So it truly is kind of the truth in terms of the role.

You do spend a lot of time communicating, whether it's internally or externally.

It's a communication role.

Well, given what you're doing now, happy to kind of take the conversation back, start to wax nostalgic and really dive into what are some of your earliest experiences with either technology or the Internet?

And how did that kind of define your early career?


Well, it's a good question. I have been interested in computers forever, basically as long as I can recall.

I always liked gadgets and toys that were electronic.

And then when computers sort of hit the market, this was like mid-'80s, my first computer was a TI-99/4A, it was basically one of those little half-gaming, half-real computer.

But I learned basic programming by typing in the programs that came inside of magazines.

They would show up once a month, you'd get a handful of programs that you could type in.

And my learning there was really around how to make those programs do something besides what they were intended to do.

And so I would make changes.

And so that led me to just really get involved in computers.

Then the family got a better computer.

We got a PC clone.

This was one of those original, 4.77 megahertz PCs.

So this takes you back a long time.

I mean, this is like Generation one PC, but again, just sort of ripped it apart, understood all the software and the hardware aspects and upgrades and did all the things that you do on a computer.

And that stayed with me, that sort of curiosity around computers and technology.

Even in college, when I got to college, I was not a computer science major.

I was more on the business side of things, but the computer science lab was open to all students.

So I spent time in the computer science lab where they had Internet access.

And so one of the very first things that I did, actually, what led me to check out the Internet was my curiosity around what you could do with it.

And one of the things that I had discovered sort of in my, I guess, tinkering with technology is that there was a particular calculator.

I'll bring up my little example here, this prop.

This is a Hewlett Packard 48 calculator that I used in some of my courses.

And in the manual for that calculator, there was a link that said you could FTP or Telnet to the Hewlett Packard BBS.

So instead of dialing up to the BBS and using long distance, at the time everything was long distance, you could telnet or FTP.

And so I said, I've got to figure out what that is.

I got to go download some programs for my calculator and figure out how to get them.

And so you went to the computer science lab, they had green-screen terminals there that you could basically get on to the Unix machine.

It was a Silicon Graphics machine that was, I never physically saw the machine.

Basically, it was a remote kind of client access to it, a login shell.

And at that point, I sort of became an Internet convert.

I loved every aspect of the newsgroups and IRC and figuring out how all the protocols worked.

I mean, the way to learn the Internet at that point was basically get a Unix manual and figure out the UNIX commands because there was literally no browsers, there was no graphical interface, it was all text-based.

But that's what got me on to the Internet.

And from then on, I mean, that's been my sort of career trajectory.

So now I have to ask, what was the first thing you downloaded to your calculator?

It's a question I don't know if I know the answer to.

I mean, there were so many little cheesy programs that were just like, you know, moving the little bouncing ball.

But I think it was probably a bouncing ball thing.

Literally, it was like one of those little graphical animation-type applications.

Because I remember that even, kind of in my high school days, with the early TI 89s and 90s, and when you, knowing the group that would install Snake or any of the very basic games or Hangman on their calculator and that's how they passed the time during pre- calc.

So it's fascinating to see that as a potential jumping-off point for both the Internet and early interaction with tech.

Yeah, well you can imagine those engineers at Hewlett-Packard, they were probably all on the Internet long before we were.

They were a little older probably than I was, certainly.

And so they probably came out of university like I did and wanted to have Internet access at their job and brought it with them into the workforce.

And that's exactly really my story as well.

After my time at university, when I left, this was like, again, the mid-'90s and internet access was not universally available.

There really weren't that many places to get it other than higher education or government or some very technical industries.

And so one of my friends from the computer lab at college, he called me one day and said, You want to start an ISP?

And I said, Yep, I do.

So we basically got together.

I worked basically for free on that little start-up for a few months just as a sort of evening gig.

I had a day job working on real computers, but my evening sort of time was spent just tinkering around, figuring out how to build an ISP.

And eventually, I joined the company, but super fun time in my life just basically figuring out all the moving parts of modems and dial-up access and making sure everything worked.

And I assume there's really no book on the shelf at that time or even on the Internet of like, hey, how to build an ISP.

You were pretty much figuring it out as you go like you needed this level of connectivity, this level of hardware, start pulling in customers that are dialing up still in this day and age.

What were some of your initial surprises or things you enjoyed the most about that role?

Well, you're describing it perfectly.

I mean, it was basically figuring it out as you go.

I mean, we had to figure out how to connect the modems.

I remember one of the funniest stories was my partner at the time, he was trying to figure out how we would organize the modems so that they didn't clutter up the room where we were installing them.

And there was a lot of cables.

You know, this was a time when each modem was a - separate...

- Cable management wasn't a thing yet. No, it wasn't.

You didn't have beautiful pictures and memes on the Internet yet of cable management.

We didn't know about cable management, certainly.

So he had this idea.

Basically, these were USRobotics Sportster modems, the cheap ones, not the really good ones.

I have another prop I'll show you in a second, but the cheap ones were these little white external modems, and you had to have a big serial cable and a power cable and a RJ 11 plug, basically a phone cable all plugged into the device.

And then heat was an issue because if you stack them, the ones on the bottom would heat up the ones on top and the ones on the bottom would start to fail.

And so it was a real problem.

His idea was to Velcro them to a big sheet of plywood on the wall.

I mean, think about sort of this wall.

You got to get this picture in your head of this big giant sheet of plywood and Velcro modems all the way across, you know, in rows and columns.

Every once in a while, one of those Velcro pieces would fail and one would just sort of fall off the wall.

And that was pretty crazy. And so we learned the lesson there, we had to get better at, again, cable management and reliability.

Those modems were not intended for 24/7 usage. And so we eventually upgraded to a better version of the USRobotics.

This is a Courier.

Oh, nice.

- You brought props.

- I brought a prop. Yeah, this one, I don't know if you can tell, but this one says "John's modem" on it.

This is literally one of the later generation of the USRobotics Courier modems.

That was the next phase is really sort of building on a better class of modem, but then long term we ended up with more of a carrier-class solution for modems where you had to buy real rackmount gear and you brought in your phone lines with T ones or ISDN lines.

And I also remember having to learn about how telcos worked when you're ordering T1s and ISDN PRIs and all these different circuits, all of a sudden you have to sort of navigate the telco world.

And that meant, you know, learning all their technology and terminology and understanding what these circuit IDs meant and the coding out of all that stuff.

So, you know, a lot of learning, you had to really figure it out on your own.

There was no manual and no one in the telco world really completely understood the Internet world.

And so it was a bit of a challenge, even translating some of the things that we were trying to accomplish.

What's fascinating is hearing, essentially your guys's iterative model of let's start with the MVP.

So how many modems can we get?

Quality is not a factor right now.

But then over time, as you were building out your system, you upgraded kind of where you needed either for capacity or better storage and cable management.

And from my perspective, it's fascinating.

You typically think when you're dialing onto the Internet, even back in the modem days and 28K and 56K modems, that it's going somewhere highly technical like, yep, I'm dialing out to a data center somewhere and they have their stuff together.

And so to really actually make that a real image of like, no, you're dialing into a modem that's hanging on a plywood sheet and you're hoping it doesn't fall off because that's how you lose your connection or that's the game you lost was your modem fell off that day is, I think, a very good image for just the early Internet and the wild, wild west that it was as these ISPs were ramping up.

Yeah, I mean, it really was what you're describing.

You had to learn as you grew and you didn't have unlimited funds to go out and buy a data center.

We eventually ended up with something that resembled a data center. It was a smaller facility with real racks and with real power infrastructure, back-up.

We did all the things that you needed to do to create a proper infrastructure over time.

But that came with more money and more subscribers and more technical know-how on our part.

And the things that we, the mistakes we made, we learned from and we improved upon over time.

And that's really how I think all businesses tend to work.

I mean, today you don't see as much of the physical aspect of that because the world has digitized a lot of things.

And so a lot of it's in code.

But I think even people that are building businesses today that are software businesses don't have it all completely wired tight.

I mean, they're really figuring things out as they go and putting proof of concept or MVPs or things that are just seeing how the market will accept it.

And that's still the case, I think.

And kind of on the business side of things, you know, being the CTO, how did you find getting a business loan back then, kind of describing to a bank, hey, we want to be an ISP.

Here's what an ISP does. When the Internet was still in its infancy, was that its own unique challenge to highlight, hey, here's revenue projections, here's what the service is.

Was that easy back then or was there a particular challenge around even getting financing?

Well, the good thing was that was sort of my partner's part of the role.

His job was the business side and the sales.

I mean, that's another important lesson when you're building any kind of a business is have, you know, take inventory of your strengths and understand what you're good at and then find the partners and the people to fill in the gaps that you're not so good at.

So my partner, he was really on the fundraising/marketing/sales.

I learned a lot by watching him.

He was a very scrappy, entrepreneurial, kind of a guy.

I was more the one that figured out how the technology worked.

Spent a lot of time in the telco closets and the basement of the, you know, the room where, or the building where we had modems and going to see customers.

That was another thing that I learned a lot about is customer service.

A technologist doesn't tend to want, most technologists want to work on the technology, they don't want to deal with the people aspect of it.

But I found that the people in that era, it was all new to them.

The idea of dialing up to the Internet.

We had one gentleman call into our sales line and asked about how big was the internet and did he need to bring his truck.

Basically, like was it something that he needed to drive home with because he didn't understand what it was, what was he getting?

And I mean, literally, he was getting a floppy disk with our startup, you know, we called it our startup disk.

And, you know, there's one of those in the background.

I can see it on your screen right there.

So you've got a little three-and-a-half-inch floppy disk, and that's what we gave out.

It had a driver for TCP IP that was called Trumpet Winsock and it was basically literally a dial-up adapter for getting PPP connected to the ISP and that's all you needed, basically.

An email client, browser, a few other pieces of kit there. But literally, the customers didn't have any idea what any of that meant and we were teaching them as we went.

Did that customer feel gypped?

Did you...

Like wait, you got me a floppy disk? This is not, you know, this is the Internet?

I don't know how to use this.


Crazy story there. Speaking of people who walked in the door to get a floppy disk.

I met my wife in the year 2000, literally the first year I joined Rackspace, I met my wife.

It turns out that she had come into my office at the old ISP and picked up one of those startup disks probably three or four years earlier.

I didn't ever interact with her then, but she remembered it very clearly that she came in, she knew where the office was, she knew some of the people.

She said, "There was a blond girl there." And I said, "Yep, I know who that was." And it was crazy that we didn't...

we crossed paths, but we didn't meet at that point.

But then five years later or so, - we got married.

- You guys were still working UDP back then, but then were able to establish a TCP connection.


A few years later. That's right.

We got to really work the nerd jokes along those lines.

Well, you pulled a good one out of the hat there.

Well, it's fascinating that not only did this early-career ISP allow you to learn and develop so much and bring about a good business partner, which you made it sound very key to building out a business is making sure you're not doing it alone or you do have additional resources to specialize where they can.

It also helped you find your wife.

It did.

It did. I think I've learned that lesson over the years in numerous roles and opportunities I've had, is this, you know, understanding your own strengths, understanding what you're good at, and then really amplifying that in terms of your focus as a role or a career.

If you can carve out a role for yourself where you're doing what you do best and then again, honing that skill or amplifying that versus a lot of people end up along their journey, in their career, they're told, "Well, you're not so good at this.

You should get better at that." You know, you get this review at the end of the quarter or the end of the year and they say, "You need to improve on your your presentations.", or "You need to improve on your delivery to the sales, in the sales function.", or whatever.

But ultimately, if there's something else that you are excited about and compelled to do every day, get up every day and you feel excited about it, that's where you ought to focus.

And I feel like my CTO roles over the years have always been... I've always had the opportunity to do what I do best, which is again explaining the technology to people that may not understand it as well as they need to or they want to.

And sort of bridging that divide between maybe a business user and a technology, a new emerging technology, like Zero Trust or like cloud computing or whatever, whatever the latest is.

That's oftentimes what I've gravitated to is blending and bridging the gap between those two worlds.

And I mean, I think that analogy makes a lot of sense of sharpening your strengths, doubling down on where you're getting the most value, you're able to provide the most value, as opposed to trying to improve things that you might be weak on.

Not to say to do that wholesale, but find the things that, "Yep, I'm not adding as much value there.

I'm going to spend my time and effort mastering or getting additional mastery of what I'm good at." Yeah.

And then if you're lucky, you can find people who will support you and you can build trust with the people around you to understand what you're not so good at.

I mean, I think ultimately you want to have a relationship with your coworkers where you trust them enough and they trust you enough to share some of the things that you might not be so good at and that you might be willing to allow or ask for some help on, because that's hard for some people.

They don't want to ask for help.

They want to try to go it alone and they want to go, you know, they don't want to admit that they have any weaknesses.

But when you can evolve your, you know, your awareness of your own skill set and get to the point where you can ask for help and you can trust people to not take advantage of your weaknesses.

I think that's really where you get into the zone and you really do your best work.

And with our last few minutes, you know, I'm fascinated to learn what you're most excited about with your work here at Cloudflare.

What are you most excited about for the future of the Internet?

Well, I think, you know, the thing that I've learned through my life is the Internet has been immensely important to me.

It's been my career basically every step of the way.

I think everybody approaches the Internet in a different way.

You know, some people get completely invested in it and involved and other people use it for whatever business they're trying to sort of accomplish.

You know, you can do any kind of a startup nowadays, and literally it almost always comes back to an Internet connection to get your business online in some form or fashion.

And then there's the people that just use it every day on their smartphone and use it to communicate.

I think communication, it has become the predominant tool for communication.

I rarely use the phone anymore.

The traditional phone, I use the Internet.

We all text, we all use chat.

And so the Internet has become part of our lives that we can't untangle that anymore.

There's no way to figure out where we stop and the Internet starts.

I mean, even your personal thoughts go into your smartphone sometimes in the form of notes or things of that sort.

So, you know, I think we're going to keep figuring out new things to do with the Internet.

I imagine the metaverse, the term metaverse. I mean, it gets thrown around a lot, but there's probably something there that is going to evolve and change.

You know, the time that we spend in front of a PC or a laptop, it may evolve over time as better interfaces come along.

I think that there's going to be more mobile Internet in terms of what's in the car, you know, the self-driving cars that we've been promised for a few years.

That will eventually get here and then you'll have more opportunity to make a better experience in that vehicle.

I think 5G is going to change fundamentally the way that we interact with our devices because they're going to be so much richer in terms of what you can do with them.

And then when you put all that together with the work that we're doing at Cloudflare is really, you know, we talk about our mission to build a better Internet, and I think Cloudflare is working hard on that.

And it's really for everyone, not just for businesses, but individuals as well.

So if you want to share content or do whatever you're excited about, you can put it online and use some of the Cloudflare products to really get that secure and reliable and scaled.

You can really match the scale of, you know, I think back to those early days where we didn't have any scale and we'd had no way to lean on other companies for it.

But now any individual has the ability to lean on really the technology being provided in a platform like Cloudflare and do some amazing stuff.

You know, you can really create a whole business around some of these technologies and get them to the market very quickly.

So it's exciting.

Security is a factor in every business.

And I think that's one that we're focused on in a big way with our Zero Trust solutions.

And that's what I've been spending a lot of time on lately.

Yeah, that's one thing that's been fascinating is just how easy it is now for anyone or a business to get connected to spin up compute resources.

There is ideally less Velcroed modems on the wall as they're going through their early phases as a business, they're able to do A/B testing on a broader scale across more markets.

And so the ability to experiment seems to have only increased as accessibility to communication and accessibility to easy compute and easy connectivity has increased.

I did a blog post, one of my first ones at Cloudflare when I joined, when I started to really explore all the different things you could do.

And it was from the perspective, not so much of a Cloudflare employee, but as a user.

What could I use for free on the Cloudflare platform?

And Cloudflare Pages was very interesting to me.

Basically, you could build a website essentially for free, and that was such a tremendously difficult task in the early days of the Internet.

And now it's so simple.

I mean, you can follow simple steps and get a website up and running that is globally available and scaled beyond your wildest dreams if you need it to be.

And you can take traffic from any user anywhere on the planet and it's reliable and it's secure and it's amazing really what is possible.

And just exploring our platform was like taking me back to my early days of figuring out how the Internet worked.

And there's so much to learn.

There's so many paths that you can go down.

And it's exciting to see how fast things are evolving, and it's really just been built on top of other people's open source projects or other people's ideas.

That's the beauty of the Internet, too, is just that collaboration.

It's not just communication, but it's the ability for people to share and build on top of other people's innovations as well.

And I mean, that can be said for something like Cloudflare TV as a whole is we've tried to find a way to better communicate and maintain company culture during a global pandemic.

How can we leverage the solutions available to us?

How can we leverage our own global network and find a way to have that communication still both created and then shared broadly?

And John, I thank you for your time.

You know, we're at the end of the session.

It was fascinating learning about the early days of wild, wild west ISPs and what the technology was once you opened the door.

And, you know, I'm glad you kind of helped launch your career as well as help launch your marriage.

Well, it was a lot of fun to chat with you today, Dan.

Thanks for taking me down the path of the memories and thank you for the time.

It's always fun getting nostalgic about the early Internet days.


Thank you. All right.

Thank you, John. And everyone catching us live or either one of the recordings.

Thank you for taking the time to wax nostalgic with us. Everyone have a great evening, morning or goodnight.


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Dial Up Motive
Human-interest segment asking Cloudflare employees what their first Internet experience was and how it informed them joining Cloudflare. Dial-up modems, bulletin boards, punch-cards, Twitch, Twitter and more.
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