Dial Up Motive

Hello, everyone. Welcome to episode 22 of Dial Up Motive. I'm your host, Dan Hollinger.

If you haven't been to the show before, this is where we explore the early technical and Internet histories with Cloudflare employees.

Today I have Sean Richardson.

He's a growth marketer at Cloudflare. Sean, welcome to the show. Hi, thanks for having me, Dan.

Awesome. We're glad to have you and we hope to explore some of your earliest or most foundational experiences with early tech and how it brought you here to Cloudflare and what you're most excited about for the future.

So kicking things off, what are you doing here at Cloudflare today?

At Cloudflare, I work in the Pago group as a growth marketer where we're working to help get more free users and more paid users and move them up the channel into all our good services of WordPress APO and Argo and Pro and Biz.

And Pago, for those that aren't speaking Cloudflare language, this is all of our kind of free our Pro and Biz plans for our customers that are able to basically just self-serve.

Self-service credit card, etc.

Yeah. It's a month-to -month. Awesome. And how long have you been with Cloudflare?

I think this week marks my 90 days or so. 90 days. So you're done with your 30, 60, 90 plan, right?

Yeah. Now you got to make up the rest of the year.

And you're dialing in from Austin? I'm based in Austin, Texas. Yeah. Awesome.

Well, glad to have you. And with that intro out of the way, would love to learn some of your earliest experiences on either we can start with the computer.

I've talked with folks that we start with a calculator.

As you can see from my background, I was the early 90s kid with a Packard Bell, CD-ROMs and floppy disks and just learning to love computers and the Internet.

And I would love to learn more about your story.

Yeah. So I think I started with an Apple IIc, I think, or the similar in the classrooms at school.

And then we had one at home for a while with the big five and a quarter floppy disks.

So, you know, bigger than the ones you got behind you.

And then eventually, you know, we as a family got a Forma 400 Macintosh. It was sort of their one of their education focused machines.

And I remember that stack of floppies brings back memories of doing backups of the machine because you were always worried about it was going to fail.

And then there were disk doublers.

So you would use a little bit of processing power you had to double the size your, you know, the hard drive.

And that would, you know, try to try to eat every little bit of performance out of the machine you could.

Yeah. I mean, you were dealing with so little memory, so little hard drive space.

I mean, I think I remember backing up across some floppy disks as well and just having to take a game across, you know, five floppy disks and being like, well, I hope this worked.

Exactly.

Then you were paranoid about your backups because you were paranoid about your live data.

It's a different age in some ways. And then, you know, slowly dial -up services started rolling out.

I lived in a small town in Texas. You know, so we had Prodigy for a while, but you were in a walled garden sort of there.

And then AOL and then, you know, fighting with the parents over the phone line and then getting a dedicated phone for that.

And then just really getting paranoid about what your dial-up bill was going to be because every minute you were on line cost something, you know, and figuring that out.

So you had a few of those memories where, you know, you're playing along on the Internet and then suddenly someone picks up the phone.

My experience was I was playing a game. Suddenly the game froze.

And then 20 seconds later, a family member would scream, you know, are you on the Internet?

Well, not anymore. You can have your phone call. It's fine. It's too late now.

I didn't capture the flag. Our team lost. Yeah. And then started getting into VBSs.

Really the quest there, you know, one thing I remember is trying to get some of the early speech synthesis stuff for Apple.

They didn't just include the library's default, but they were available on Apple's FTP or Gopher.

Maybe it was even Gopher site.

But to get on Gopher, you had to get on the Internet. So it was trying to find some way to get to the Internet from where I lived.

And so you go to some VBSs had minor uplinks or they would mirror some of these things down.

And so, you know, you'd start setting up the VBS and then there was, you know, lots of rankings and credibility and all this sort of stuff.

So one thing you could always do is there was sort of a reciprocity of if you hosted a VBS, then you got more permissions on other VBSs.

So you would set up, install the software and run it.

And then at some point in random time, they would call back and log on to your system and you'd create an account for them and then you get upgrade permissions on their site.

And, you know, that was all fun and whatnot.

But, you know, still some, you know, VBSs, you know, they were small, they were trying to learn them, etc.

And then, you know, finally, where I lived in Horton HS, we got dial up actual Internet from a company.

Started being released.

And, you know, I think that might have been right around the time. I upgraded from a 2400 to a 9600 baud modem.

So I was ready to just really, really just download all so fast.

Yeah. That was broadband back then. Yeah. And, you know. Yeah.

And in the VBS world, like it sounds very much like the Wild Wild West where you're almost just trading on a reputation.

Yeah. That, oh, I have access to this and this is my level of access.

Oh, and you can double check my level of access over here.

And, you know, building what seems like a very small network of folks.

And you're you're only kind of claim to anything is that you've either been established somewhere else or you've established yourself on a network.

What kind of bulletin board sites were you visiting or taking part in?

I was really just trying to explore and learn.

I mean, I had you know, it was you know, I didn't have a local user group meet up.

I, you know, only had a few friends who were even remotely into technology that level at the time.

It wasn't sort of the popular thing to do, especially in, you know, 20,000 person town, Texas at the time.

And so it was just really trying to explore and just figure out what all you could do and tinker and, you know, see if there were software being on a Mac limited some of the software exchanges I could do.

So it always be like, oh, do you have any, you know, wares or similar, you know, free software or shareware or whatnot that you can upload?

And I had limited access to what I had or could run. But, you know, you sort of gather things to use as credits to sort of get access to see what people had, because even just being able to roam around would cost you sort of bandwidth credits, if you will.

Yeah, there was no consolidated search. No. You know, and from a software perspective, there's no Pirate Bay, there's, you know, you were really, and in most cases, probably at this stage, you were just hunting for the sake of exploring and learning.

Yeah. Like, oh, I didn't know this was available.

Now it is. Right. How do I learn it and use it? Yeah, I mean, it was, yeah, I mean, it's sort of like going for a walk in the woods and getting lost on purpose just to go and get lost and see new things.

And, you know, with no real objective other than that satisfaction of learning and doing something that, you know, you had never done before and few people at the time were doing.

It seems so different to, you know, the day and age now where, you know, we have CDNs which make the constant distribution relatively straightforward.

We have massive indexes of this content.

You know, it is rather straightforward to find or discover, and you're much less wild wild west, but still still growing and evolving.

Yeah. Yeah. I mean, yeah, this just finally like an up -to-date version of a C library or something was a really big deal because, you know, this was before even, you know, I can remember a few years later in high school ordering CDs of Linux distributions because that was the fastest way to get the latest copy of, you know, Debian or, you know, even OpenBSD.

And, you know, getting excited about getting the CD from Canada so that you got the crypto libraries because Canada could distribute them, but other people couldn't and then OpenBSD had these great stickers and...

Well, if you think about it, the bandwidth of mailing a CD was faster than your 96k, you know, baud modem.

Yeah, yeah, yeah. I mean, substantially. But yeah, then it was, yeah, it was interesting.

And then, you know, you'd load that in and you'd get an OS installed and that was a big accomplishment.

You were like, all right, weekend accomplished.

Good, you know. Now, did you feel, you know, you're already taking things farther than your peers?

Because, I mean, it sounds like it was the Oregon Trail generation, you know, you had that available.

Some people were getting into tech, at least a little.

But, I mean, if you're actually getting, you know, asking for Linux CDs, were you kind of pushing the bar, you know, not only for your area, but just kind of your own technical level?

Yeah, I mean, I was definitely getting told by, you know, I may have gotten told by one or two programming teachers in school to stop showing people what I was doing.

Because it was, you know, we were trying, we were trying to just compile a simple hello world.

And I was showing them, you know, things drawing, you know, graphics and stuff on the screen.

And they wanted to jump to that and I was ruining the lesson plan.

So, you know. Heaven forbid you try to teach people. Right, right. Or, yeah, or expand your own knowledge ahead of the timeline that the teacher wanted you to.

But no, so I mean, then, you know, I think around that time, also, I was talking about the Internet provider.

You know, that was a really big deal. It was going to be the raw Internet, relatively unmetered, you know, barring again, because the bandwidth was so, so small that you could actually get to your house because of the modem issue.

So maybe we're up to 57, six modems by then, or, you know, something like that.

And, you know, just one memory I love from the time was just, I distinctly, I pinged the new Internet provider I had about, you know, if they were going to have shell access on any Unix machines, try to just start learning that.

And then if they were going to have web space, and, you know, because you needed a server somewhere to put, so that you could have to be files up to put them on the web to point things at.

And you needed somebody else to, you know, have Apache and, you know, have all that sort of taken care of.

And they were like, Oh, yeah, we're thinking about doing that.

And, you know, they were, it turns out they were, you know, three or four people in a rundown building that had gotten, that had bought a whole bunch of modems and a whole bunch of phone lines and got a T1 and, or, you know, maybe a T1 even.

And some Sun workstations that they got off a local refinery, who was unloading old hardware, and they were, you know, so they had all these Spark stations to run the servers.

And it was, anyway, I wound up meeting the guys, they offered me.

So yeah, sometimes it's better not to see how the sausage or the network gets made.

Correct. Especially back then, when it was like a handful of people thinking, yeah, I can, I can throw these things together, or good enough to get that T1 and then start selling it.

Like, and for most people, they're oblivious to, you know, how, how either, how much duct tape is involved in getting it together.

And that's, you know, 100 or 1000s of people's of Internet connections.

Yeah. So I mean, back then when I eventually started working for them.

Back then their points of presence were a little different than Cloudflare's. Their points of presence were a closet that they would give free Internet access to a business to run, you know, 10 to 20, 30 phone lines into that, into that closet.

And then they would bring in some plywood or a board, and they would have the mount that we would mount the modems to the, to the boards with either some straps and some screws or, you know, may have been some duct tape involved from time to time.

And so you just have these sort of giant power strips with a piece of wood and modems attached to, you know, 15 with a US Robotics modems, you know, or whichever modem at the time was our fast and reliable one and strapped to there.

And then, you know, that was a point of presence to bring to the local because again, you had long distance fees.

So you wanted to bring it to set up a new local exchange and have your users not have to pay long distance fees that they'd be willing to.

It was one of the upsells was like, oh, we're so local that you don't have to pay the long distance fees.

You just pay us to get on the Internet, not that plus the phone company bill.

And, uh, yeah, it was, it was interesting, you know, and then much like Cloudflare now has, has hardware that they decide this has some, some quirks to it.

We would learn that, you know, certain serial number ranges of US Robotics modems had really bad reliability issues and have to go swap them all out and all over Texas at the time.

So, and this was your first job at what age?

So I believe it was, it was, I was 16. So, or maybe I guess it would, uh, yeah, Texas.

So I would have been 16. I just got my driver's license, just gotten access to the car.

Yeah. The company you called like, Hey, are you doing XYZ?

And they're like, well, we're thinking about it. Do you want to come work for us?

Yes. Yeah. So I asked them, Hey, are you going to set up web space? I'm looking to play with this, this web thing.

And, um, they're like, Oh, actually we're looking for a webmaster.

Um, that's to, to, to really date it. Um, and, uh, would you be interested in coming in and talking to us about it?

And, you know, I hadn't written any HTML at this time.

I was trying to find the space to then start learning HTML or to do something with it other than run it locally.

And, um, while it walked out of there with the job, um, and some shock looks on their faces as they were, they did not know they were talking to a 16 year old kid and the way to bucko five, maybe.

Um, and, uh, I drove from there to the mall and went to the computer, the video game slash bookstore, little tiny bookstore at the time in the mall and bought the one book I could find on HTML, which, you know, about the width of my pinky.

And, uh, started doing stuff for them. And so I built some graphics for them, built their homepage.

Um, I was in a mess. You're an example of, you know, you say yes to the opportunity first.

And then when no one's looking, figure out how to do the opportunity.

I, I did not. It sounded like a lot of my work here at Cloudflare.

Okay. Um, I have, I have, you know, you adapt, um, they, they needed help.

I wanted to do some stuff and, uh, then it expanded.

They needed Mac software. So I helped with their training, their people on like how to do Mac drivers for the PPP connections and the, whatever the other one was.

Um, and so we had, we made Mac software and that became a big selling point for them, um, in the area.

Cause, um, it was just, there was a, yeah, there was a large sizable enough Mac community that wanted to get on the Internet.

And I think Apple was shutting down eWorld or Apple had a whole, their own little ISP for a while.

Um, that was like mini prodigy or something.

And, um, yeah, no, it was a great opportunity. Learned a lot of stuff, started getting into Unix.

Um, it's funny on, on the Cloudflare thing there. We quickly learned that, um, we were suddenly hosting a whole bunch of, um, illegal wares on one of the big servers.

Cause it hadn't been locked down and people had probed the Internet even back then and found space with bandwidth and put the files there and we're sharing them all over the place.

So that's interesting. Just highlighting, you know, even at that small scale kind of a lack of observability, a lack of analytics or logs, like no one's coming through the logs and actually checking who's accessing what.

And so to have an open connection that, you know, in both a black hat or white hat or gray hat world, you know, people would then find a way to, um, you know, either abuse or, or use it in ways that you weren't, weren't expecting.

So it's interesting that, you know, at that early stage of the Internet, there are still many of the problems that we're facing today of, of people finding, you know, whatever loophole they can or bad code they can and then finding a way in.

Yeah. Yeah. Um, yeah, definitely. And, you know, back then when the pipes weren't big and there wasn't a lot of space available.

So, you know, suddenly that person putting wares up there and a hundred people starting to try to download stuff from it then ruins the Internet connection for, you know, 200 dial-up customers, you know, who are relying on those pipes.

So, um, you know, it's, it's a, it's the same challenges, but it, again, it does tie into like Cloudflare's mission of like, you know, we can take these giant DDOSs and other hits where, you know, people don't even have to worry about this stuff, but provide the insights, you know, with access and teams and all these other products where all these things that are hard to remember to, you know, they just added an overhead when you're trying to build and stand up stuff.

We can take on a lot of that burden for our customers.

And I know at the top of the show, you know, I introduced you as a growth marketer.

How did you go from, you know, literally plugging in kind of at an early ISP in the beginning of your career at the dawn of your career towards kind of the market building or marketer level approach?

Yeah. Um, so, you know, I went off to, I went up to, went off to college at Dartmouth and there I got into computer science.

My advisor wanted me to balance computer science and math I was doing with something on the other end of the spectrum.

So we, we found anthropology. So I studied anthropology, which studied humans and behaviors and marketing and thinking and evolution alongside, you know, computer science.

And so that was always been an interesting dynamic in my life as I look at, you know, computers are such a part of humans and humans are such a part of computers.

Um, and then, you know, I went from there. I worked at a nonprofit getting computers to underprivileged schools and kids, and then, um, started a few startups, went to business school, um, business school learned, you know, a lot about marketing.

I was gonna say, did all your startups, um, succeed, fail, or is that what led to business school of like, oh, I've, I've tried this a few times and, you know, I can't balance the books or what did that journey look like?

Yeah. Um, the, the business school kind of was the tech part. I got the marketing, the business side, um, you know, less balancing books and more, you know, how do we position and how do you even to, to like a, to raise money or to, or to a customer?

How do you start marketing this? How do you think about that?

How do you think about those numbers? Um, put, put some of that in and then also the net, you know, just some good networking and, and et cetera.

Um, and then while I was there, word got out, you know, that I'd done some startup stuff and been an engineer and et cetera.

And so suddenly I was having, you know, lunches left and right of people who wanted to start their, I've got this idea.

Um, yeah, I need a tech founder.

Yeah. No tech. And also, you know, I happen to be taking these MBA.

Can you be a tech founder? Well, more frequently it was, I'm not looking for a tech founder.

I want an advisor because I'm just gonna, I'm gonna shove some money at this undergrad.

I, I'm going to, I'm going to find an undergrad to build this for me, um, for a little piece of equity and some cash.

And I'm going to be this, uh, tech company guru.

And you're like, well, but you probably need a tech founder.

And that, that was always my first part of the conversation was trying to like, if you're talking about building a tech company, you probably need a tech founder.

Yeah. And especially if you're a non-technical founder and you're trying to boss around, you know, an undergraduate that knows how to code or it's just learning how to code.

Right. That, that, that doesn't seem like a recipe for success in most cases.

Yeah. And not to say that you couldn't get lucky and there's not, you know, brilliant undergrads out there.

I'm not trying to diminish the skill set of undergrad.

No, it's not even, it still seems like a roll of the dice.

Well, it's more, it's more, if you're going to empower, if you're going to rely on them for that amount, that, that, I mean, for a giant amount of success of the product, you probably should enable them and, you know, make them a co-owner in, from the start so that they have that buy-in et cetera.

Because if they don't have that, then you're really disenfranchising them.

And what advice might you give to other, others out there watching this that maybe started life in the engineering side, got the computer science or engineering degree, and then want to explore getting that business degree or that MBA?

What, what do you think are some of the perks or benefits to that?

You know, so I think the, the challenge can be, you know, as I think it was said in Goodwill Hunting, there's, there's not much you can't learn for $1.95 and late fees at the, at the local bookstore.

But at the same point in time, it's not just about the learning and the books and et cetera.

It's about that experience of being around the people with that very different mindset.

So, you know, I think, I think that's, you know, find interesting people who challenge you, not just within your current realm.

It's, you know, I would go to meetups that are something you don't, that's not even in your universe, you know, or, you know, join a speaking club or, you know, just, just get exposed to those new ideas because you just never know when that little bit of, you know, magic's going to happen in your own brain or chemistry with someone else and, and lead to, lead to that understanding of that, the other parts of the equation.

Yeah. I know that was kind of my personal experience was in a way you're just picking up additional languages.

So, you know, I'm not fluent in marketing, but I can speak marketing.

I'm not fluent in accounting, but, you know, I know enough pigeon accounting to get by.

And that combined with a handful of programming languages or an engineering approach to design and bringing up problems tends to be a very interesting set of languages and then allow you to do more or unlock more problems.

Yeah. Yeah. Try to bring yourself closer to the center of as many intersections and spaces as you can and maintain some expertise, but, but be able to be that bridge because the more to your point, the more you can be that translator or, or at least understand, you know, the, you know, without some level of abstraction, the better.

Yeah. So we, we went from, you know, dialing into a few bulletin board systems, hacking together a Texas ISP, getting your, your MBA.

And, and then I guess what led you to, to Cloudflare in your final steps?

So Cloudflare, you know, I'd launched, you know, a successful startup on the, in the past and was looking to move away from, I was working at a family office here at Austin, looking to move away from them.

Just, they were, we, I'd taken them for nine years of stuff.

And I was just going through lots of lists and old markers and stew lists and companies I was curious about.

And I realized Cloudflare had been one of them for a long time.

Like I was telling you earlier, I think I joined and created my first account in January, 2012.

And, you know, Cloudflare has been sort of, I guess, part of my life since then.

And I was talking to my wife and we were trying to brainstorm on companies and ideas and et cetera.

And, you know, some openings happened up and Cloudflare has been exploding in growth in Austin.

And here we are.

Awesome. And yeah, glad to have you and, you know, that range of experience and in our final few minutes, what are you most excited about kind of for the future of technology or the Internet, either, you know, what you're doing today or what Cloudflare is doing today or some of the other companies out there?

So, you know, something I'm really, I'm excited about is, you know, I wish it had happened sooner, but it's happening finally is I think security and privacy and trust are really starting to like become top of mind for a lot of people.

And I think, you know, it's like I look at my honors thesis work I did undergrad was around PKI and a lot of those same comments, a lot of those same comments or concepts of why should I trust this device, you know, are starting to come around of like, you know, let's put it on the network and not worry about it is going away.

And it's let's put it on the network and it can establish itself and its credibility and its trust and what it can do.

And we can bless it to do as few things as possible.

And we can monitor it. And if it starts misbehaving, we can shut it down quickly.

You know, and getting rid of this, getting rid of some of the, you know, I think, you know, VPN and a lot of these concepts and like having to give things full access and then dial it back and being able to flip those equations to the easier, let's just trust it as little as possible and then open it up and being able to do that at an increasingly micro level.

So rather than network to network, being able to do it, like all devices are their own island and they have to have paths to do anything else.

So whether it's a camera or it's my thermostat, you know, why does my thermostat need to be able to talk to my TV?

So almost, you know, solving those same problems from those early ISP days and taking just a different paradigm of, you know, we're not going to have it wide open.

How do we have it limited or check every single time with the proper permissions that can be monitored and reduced or grow over time?

Yeah. And it's not always malicious. Sometimes it just, you know, devices have bugs or devices fail, but you know, I don't want my thermostat setting my house on fire no matter what.

I mean, hopefully. When the robot operating comes, you know, I'm trying to be nice to my virtual assistants.

You should be. All right. They have long memories. They do. You know, they probably have a marker and index of all the times I, you know, say thank you or show gratitude.

That will spare me in the apocalypse. Or they have video that they can just go watch later and catch up.

All right. And with that, we're near the end of the time.

So Sean, I thank you for taking us through your Internet journey and your dial-up motive.

For anyone catching the live stream, thank you for catching the show.

And for anyone watching a recording, I hope you had a wonderful morning, evening, or good night.

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