Kyler Middleton is a Hashi Ambassador and AWS Community Builder. They dive into the captivating world of DevOps and explore the importance of technical expertise combined with effective communication skills. Kyler shares valuable insights on topics ranging from building a robust skillset to the challenges and responsibilities of security engineers. Moreover, they uncover the secrets to achieving developer velocity, integrating automation into workflows, and understanding the foundational knowledge in networking.  They navigate the complexities of the cloud environment and explore the transformative nature of technical and computer skills.

 

Jonathan (00:01.658)

Good day everybody. Welcome to another exciting episode of Adventures in DevOps. I am your only host for the day. Everyone else couldn't make it, Jonathan Hall, but I have an exciting guest today, Kyler Middleton. Welcome to the show.

 

Kyler Middleton (kyler.omg.lol) (00:15.347)

Thank you so much. I'm excited to be here.

 

Jonathan (00:18.29)

I'm glad to have you here. We spoke very briefly before we started recording. Sounds like you have a very interesting sort of professional, maybe life story. I'm hoping to learn a little bit about that. You said you started, I don't know if you were raised on a farm, but there's farming in your background. Tell me a little bit about that.

 

Kyler Middleton (kyler.omg.lol) (00:35.723)

Absolutely. I was raised in Western Nebraska for any international folks. That is the Midwest of the United States, which is very, very rural, very tractor and irrigation and growing stuff out of the ground focused. And I'm currently a sort of seniorish DevOps engineer that speaks at conferences. And that has been a pretty exciting journey, pretty interesting journey.

 

Kyler Middleton (kyler.omg.lol) (01:05.817)

you farm because the family's livelihood depends on it. So get in that tractor, do that irrigation, let's go!

 

Jonathan (01:07.182)

Yeah.

 

Jonathan (01:13.134)

Awesome. So I've never lived on a farm, but I grew up in a farming community. I grew up in central Kansas and a town of about 500 people. So all of my classmates, many of my classmates were farm kids too. So I know that culture. And now I speak at conferences and do DevOps too.

 

Kyler Middleton (kyler.omg.lol) (01:32.423)

Small towns represent. I um my graduating class in high school was 21 students in a town of 1200. I grew up outside a town of 80 so yeah let's go. Like I like that our podcast today is small town kids.

 

Jonathan (01:34.111)

Yeah.

 

Jonathan (01:37.536)

Okay.

 

Jonathan (01:45.443)

They were 32 in my class. It's rare that I meet somebody with a smaller class. That's very rare. Yeah, yeah. So how did you get started? I mean, yeah, what sparked your interest in IT and in computers? How did that happen for you?

 

Kyler Middleton (kyler.omg.lol) (01:49.809)

absolutely tiny little class.

 

Kyler Middleton (kyler.omg.lol) (02:00.915)

I have this adorable little story that a lot of farmers have new technology and they sort of have to innovate because it's gotten pretty difficult to make it work as a farmer, particularly in the United States. It's expensive. So a lot of them had computers. When I was growing up in the early 90s, I'm dating myself a little, and when the computers would break at this time, I don't know if it's still the case, folks from the big city of about 40,000 people would charge by the mile.

 

Jonathan (02:14.221)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (02:30.649)

to come out and fix their computer to drive out there. And that was pretty expensive because farmers don't have a lot to go around. And I was a quirky little strange kid, but I would come out and I would try and fix her computer based on no knowledge mind you. But I would just charge in like brownies and rice krispie treats. And that was way more affordable. And I wouldn't because my mom would drive me in a minivan. So it would be much less expensive for them. And eventually I just learned that like it's fun. It's fun to play with computers. I don't consider it work. I never

 

Jonathan (02:46.798)

Hehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehehe

 

Jonathan (02:52.664)

Yeah.

 

Kyler Middleton (kyler.omg.lol) (03:00.529)

think it's fun to just mess around all day. And there's a lot more air conditioning than in most tractors. So life has improved dramatically here.

 

Jonathan (03:06.753)

Oh, yeah.

 

Nice. Yeah, I did a lot of that too, helping the people around town and out in the country. Computer's broken, Jonathan, you can fix it. And I made a little bit of money. I charged more than Brownies. I think I made $20 an hour or something. I don't remember. It probably changed, but I remember it was something. But at the time, it felt like a lot of money.

 

Kyler Middleton (kyler.omg.lol) (03:28.991)

Totally. I think eventually I started charging when I realized people would give me money because it didn't seem like... computers have always seemed to just kind of make sense and I wish I had a better explanation for that but they're just they're very logical and they always work the same way and people don't and so computers just kind of feel more at home for me. And I got all the way halfway through college I was going to be a children's librarian because children are adorable and I have a toddler now so like that has been amazing.

 

Jonathan (03:33.206)

Yeah.

 

Jonathan (03:47.043)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (03:56.935)

before I realized that like this is a career. This is not just a hobby that people appreciate. This is actually like, they'll give you quite a bit of money to just build computer things. And I did my best to sort of change the track of my life away from being a librarian, which is an amazing career path to an IT tech because there's a lot more money there and that's sad and shallow and the path that I chose.

 

Jonathan (04:00.738)

Yeah.

 

Jonathan (04:06.156)

Mm-hmm.

 

Jonathan (04:13.259)

Mm-hmm.

 

Jonathan (04:20.474)

Yeah, nice. So I know what kind of highlights you want to hit on in your story here, but let's jump ahead to now. What are you doing right now? And then we'll go back and fill in some of those gaps.

 

Kyler Middleton (kyler.omg.lol) (04:31.243)

Totally. I work for an EHR company in the United States. And EHR is a medical records for doctors and nurses, but also for patients to access their medical histories and doctor's notes and get prescriptions and stuff like that. And I am a senior principal DevOps architect or something like that, but I literally can't remember. It's something long and bureaucratic. So I go by the cloud security check on the internet

 

Jonathan (04:57.737)

Mm-hmm.

 

Okay. Yes.

 

Kyler Middleton (kyler.omg.lol) (05:01.237)

to remember. It's a little catchier. But primarily I'm like a free agent within my company. I go around and I find projects that are stuck. And if you've ever done consulting, projects get stuck because of there's a lack of technical knowledge, or there's a cultural gap, or there's both. Those are the most challenging where they're kind of threatened by you being there. And you get to try and unstick the project. So I'm a professional project unsticker. And I find it very, very fun.

 

Jonathan (05:22.039)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (05:31.177)

to sort of unstick stuff and teach people how to do computer things.

 

Jonathan (05:34.882)

Cool. And you mentioned that you speak at conferences. What are your favorite or most recent topics that you've spoken about?

 

Kyler Middleton (kyler.omg.lol) (05:42.091)

Totally. Last year, I spoke at RSA, which was just an incredible way to get started. Jump to the top of the stack, and it's all downhill from here. And just talked about how do you secure a health care environment? Clouds being used for secure workloads are pretty new in the industry for military, for health care, for payment card stuff. In the cloud, clouds are notoriously insecure. So how do you make sure that it's safe for your data, for your regulations?

 

Jonathan (05:49.614)

Mm-hmm.

 

Jonathan (05:53.431)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (06:12.705)

require us to be secure. So how do you justify putting it in the cloud? So I've spoken on that a ton. There's a lot of things you can do and there's a lot of ways to do it wrong. So it takes a great deal of skill and expertise. And also just teaching primarily folks that are historically disenfranchised, minorities, queer folks. I'm a queer person myself, so I connect with those people, those people being me.

 

Jonathan (06:36.034)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (06:37.159)

And I love it. I came out, I work a few years ago as a transgender person. And since then, just folks of all sorts of minority groups have reached out to me because I'm very friendly and I'll talk your ear off and been like, hey, can you help me? I'm trying to ask for help and no one will answer my questions. The stack exchange of the internet is never helpful. The stack exchange of the internet tells you you're wrong to ask that question and go figure it out your damn self.

 

Jonathan (06:54.776)

Mm-hmm.

 

Jonathan (07:01.898)

Yeah, yeah. Cool. All right.

 

Jonathan (07:10.87)

We'll pause here for a minute. We can edit this part out here. How do you, yeah, I'm trying to figure out where we want to go from here. Do you want to make this like a narrative? Do you want to go back and sort of fill in the gaps of your career? Do you want to talk, you want to dive into something about security, about healthcare? Where do you want to take this show?

 

Kyler Middleton (kyler.omg.lol) (07:13.867)

That's a lot to dump on you there.

 

Kyler Middleton (kyler.omg.lol) (07:34.447)

I think either is fine. I love talking about cloud security. Let's, yeah, let's steer into just like technical industry cloud stuff. But we could certainly scatter in narrative stuff. I like both.

 

Jonathan (07:38.222)

Okay, wanna do that?

 

Jonathan (07:46.902)

Okay. All right. Well, let's cut back in with the edit. Talk to me about some of the of the problems maybe you're solving. You say you go around and get things unstuck. Is there one in particular recently maybe that stands out that would be interesting to talk about?

 

Kyler Middleton (kyler.omg.lol) (08:05.571)

Yeah, absolutely. This is a great, this is a great segue for I'm speaking at CloudSec Next in a few months, I think. I hope it's not sooner because I need time to write that conference talk about moving a company of about 1,500 repos and 200 developers from an internal bitbucket server, stash is the old name for that, to GitHub and making sure nothing breaks, you know, while you're building the plane as you fly it. It took me about eight months to migrate.

 

Jonathan (08:12.831)

Okay.

 

Kyler Middleton (kyler.omg.lol) (08:35.705)

over and I had a totally downtime-free migration which was absolutely incredible and incredibly complicated. And I got it working, which is fun. The conference talk specifically is about I wrote dozens of tools and didn't get fired, migrating my company to GitHub.

 

Jonathan (08:53.286)

Nice.

 

Kyler Middleton (kyler.omg.lol) (08:54.203)

Absolutely, and tons of fun, tons of challenges. I could probably talk for our entire hour on that if you're interested, but just trying to find big projects that sort of marry culture, processes, technology together. That's what DevOps is after all, so just trying to find the heart of DevOps and make it work for us.

 

Jonathan (09:10.658)

Mm-hmm.

 

Jonathan (09:15.435)

Mm-hmm. A lot of people I talk to who are security focused tend to sort of, I don't want to say this in a negative sense because I don't mean it that way, but they're less hands-on. They're more conceptual. It sounds like you're really hands-on though. Is that a fair assessment? Yeah.

 

Kyler Middleton (kyler.omg.lol) (09:31.211)

Absolutely, and no one knows what to do with me. I am I was told yesterday at work that I have reached the highest level possible by an individual contributor. There's nowhere left to go unless I want to be a manager and I don't I like to lead I don't like to manage. I don't care about your dental plan. I want to do technical work. I want to be hands-on so I've just started to sort of reach out to podcasts to conferences It's the only way I can figure out how to keep growing my skills. So that's the plan

 

Jonathan (09:50.235)

Mm-hmm. Right.

 

Jonathan (10:00.094)

Yeah, nice. Yeah, I've bumped into that. I've talked to many people who bump into that, you know, depending on the company you're in, how far you can go. But like the corporate environment is designed for people to move into management. And fortunately, many companies are trying very hard to accommodate those who want to continue down the technical track. But it still feels like there's kind of a dead end there. Eventually, maybe you have two more levels now than you did five years ago, but eventually you're going to bumped into that dead end. And that's unfortunate.

 

Kyler Middleton (kyler.omg.lol) (10:13.107)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (10:28.507)

Absolutely. I talked to our HR business partner and I was like, what can I do? Like, can we create another level for me? I promise I'm cool. I could do it. And they were like, well, focus on your skills. It felt very much like what you would tell an intern when they're trying to get a role at your company. It's like, go read some books, you know, make sure you do a good job at your job. And I'm like, no, I'm doing that. I promise. I, this is a different challenge than what you're conceptualizing here. But yeah, it's definitely.

 

Jonathan (10:44.558)

Mm-hmm.

 

Jonathan (10:56.683)

Yeah.

 

Kyler Middleton (kyler.omg.lol) (10:58.461)

cultural problem across the industry that there are techie people that understand that they would be a poor manager. I don't want to manage. I would do a bad job of it. I want to lead. And that's hard. That's hard to find a niche for it because I think I have to create it. So I'm gonna help create it. I'm gonna do it.

 

Jonathan (11:11.362)

Mm-hmm.

 

Good. Awesome. Do you have any advice? I usually say the advice questions till the end, but I just wanted to ask this one now. Do you have any advice for other people who might be bumping into that dead end? What can they do? I mean, you told about what you've done and they could apply that I'm sure, but maybe you have some specific advice for people who are feeling this frustration.

 

Kyler Middleton (kyler.omg.lol) (11:34.183)

Yeah, absolutely. I am pretty technical. I'm not, I'm not...

 

junior in the technical sense, but that's not where I stand out at work and that's not how I get accolades and how I get known in this industry. Primarily, it's because of social skills and talking to people and communicating how stuff works. You can build the most amazing tools in the world, but if the human people around you can't use them and understand how they work, they are not benefiting very many people. Your impact on your company, on your industry, on your career is going to be capped. It's going to be limited.

 

Jonathan (12:04.5)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (12:11.901)

as you can be in your spot and you know your thing backwards and forwards, it's time to focus on the soft skills and teaching. Make sure the people around you understand it. I like to talk about this metaphor of like, if you are just an expert at this one thing and nobody else knows it, you have built a moat around your castle and that's amazing. Your company can't fire you ever. That sounds great, but all the new skills, you're not going to get assigned to. All the new industries, all the new developments. Nope.

 

around it. Everybody else is going to be moving on without you until they don't need your castle anymore. So I don't I don't encourage people don't build a moat around your stuff. Teach everybody what you know. That's what I've done at work. I make myself redundant as often as I can because then I can move on to the new stuff. And your managers and your peers will notice that like you're a fount of new cool stuff. Hang out with Kyler. She will give you all the cool stuff about modern technology and just hanging around with her you're going to learn some stuff. And like

 

that's totally a soft skill and I find it works very, very well.

 

Jonathan (13:15.906)

really good advice. And I would just add one thing that I can imagine some people think, because I hear this complaint or this fear frequently is, if I do that, then I might get fired or might get laid off if I'm not necessary. But there are a thousand other companies out there who would love to have somebody with those sorts of skills. So yes, maybe you'll be laid off because you're not quote essential.

 

Kyler Middleton (kyler.omg.lol) (13:39.129)

Mm-hmm.

 

Jonathan (13:43.675)

in some managers eyes unfortunately, but other managers would love to have those skills. So it's not, it's still a good long-term career play in my view.

 

Kyler Middleton (kyler.omg.lol) (13:52.307)

Absolutely. I totally agree. I think the answer to that question is, yeah, absolutely. Just like you said, you might be laid off because you have made yourself redundant, but you know what you've done is you've automated something useful and that is always going to be a portable useful skill.

 

Jonathan (14:07.702)

Definitely. Cool. So you speak about security. It doesn't sound like you limit yourself to security. You do lots of stuff, but I guess security's a nice hook to sort of hang your identity on and that personal brand. So let's talk about security a little bit. I don't really know where to start because it's such a big topic. So I'll start one place I've started a few times before when I talk about security, and that is...

 

Literally the question, where do you start? Because I worked a lot with small company startups and they often have the idea that, well, once we're profitable or once we have customers or whatever, then we'll worry about security. And that's really dangerous, of course. But what advice to give to somebody who's in this mindset of security is a someday thing, where do you start?

 

Kyler Middleton (kyler.omg.lol) (15:02.055)

Oh my goodness, it's so hard to define and sort of put a box around it because it's like DevOps. It needs something different to every single person that you talk to. But I think that's important to remember. I've run into security engineers that they live in their vertical and they've decided that security is the only thing that matters. If it's not secure, we shouldn't do it. And that's needed in some places. If you're in a regulated industry, you have to do that full stop. But in a lot of industries, you just need to be competitive.

 

So I try to focus on it's often called developer velocity, but in practice it just means make stuff easy for the people that are writing your thing that makes you money. If they're writing an app and that's how you make your money, make their lives easy. And you do that by making the tooling work well. Look at pre-commit checks, look at automated testing. If they take an hour to test their code somehow, can you shard that testing over a couple builders and make

 

Kyler Middleton (kyler.omg.lol) (16:02.189)

to build the thing that makes you money and easier, it'll make their lives better and they'll really like to have you around. And it becomes really easy once you've automated those things to shim in security tooling and scanning tooling. Like once you've automated those testing procedures, you can start to shim in all sorts of security bolt-ons. I know like on paper, we hear this a lot from a lot of really smart people that like security from the onset. And I love it, but it's often just not possible

 

and to be competitive you have to move fast and security is hard. So you will almost always be in situations where it wasn't built securely. It's your job to help as much as you can and that means shim and security, automate everything that developers do, and just make their lives easier.

 

Jonathan (16:53.23)

Do you think, let me rephrase that question, how much does an individual developer need to understand security versus let a professional, security professional, so to speak, sort of guide them or tell them when they need to do something?

 

Kyler Middleton (kyler.omg.lol) (17:10.779)

I think it's interesting because...

 

In the data center world, when it's in your data center, in your garage, or like down the street, very, very little. Your database engineers need to understand databases, your network engineers need to understand the network. In a cloud environment, those lines are so fuzzy because everybody can do everything. And that's what I actually just encourage. I don't, I don't think you should fight the stream of desiloing in cloud environments because I think it's just going to

 

Kyler Middleton (kyler.omg.lol) (17:43.105)

So I think you need to teach your team how cloud security works. Which resources do you have that have public IPs? How can you limit access to them or have like a web application firewall in front of the services you're building? At least for the stuff that those teams might build. If a database can be on the internet, they need to understand what a WAF is. If a VPN might be in the internet, they need to understand how to log connections to it. So just I think those you're sort of going to be helping

 

your team's specialists that historically have not had to desilo, to desilo their skill sets and learn about security holistically around their thing. And that's hard. That's a cultural battle and it always will be because they're happy in their moat. Databases and networks have been the same for decades, but I'm sorry cloud is just changing the world.

 

Jonathan (18:28.768)

Mm-hmm.

 

Jonathan (18:37.486)

Yeah, yeah, that's one of the complaints I suppose, or observations at least that we hear, especially about DevOps, is that everybody has to learn new skills and there's just so much more to learn. But I don't really know, I mean, there are some ways that we can limit that, but in general, I think that it's just the reality. There is more to learn.

 

Kyler Middleton (kyler.omg.lol) (19:01.781)

Yeah.

 

Absolutely. And there's, there's so much you can do, but it just, you won't ever cover the whole gap because even if you have just a perfect knowledge today, things change literally every day. All of the platforms are developing new things. Kubernetes is going to eat all of our lunch anyway, and that's a totally different take on networking and workloads. So I think you just have to get used to learning. I think that's just part of most professions in the cloud space now is prepare to

 

Jonathan (19:23.884)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (19:33.469)

career because otherwise you'll get left behind.

 

Jonathan (19:37.026)

So you've talked a bit about automated testing and making life easy for developers. How do you see that intersecting with a regulated industry like healthcare? Because there's a lot of security and privacy concerns there. And I hear a lot of people on social media saying, well, you know, that continuous delivery thing is good for you, but here in this regulated industry, it's not possible or it's difficult or whatever. How do you see the intersection?

 

Kyler Middleton (kyler.omg.lol) (20:06.099)

Absolutely. So I speak at conferences occasionally, and that's almost always the focus is, how do you justify having all these regulated workloads? Because I'm in the healthcare in the United States, which is a highly regulated industry in the cloud. And you need to explain to folks that the cloud is not what it was 10 years ago, where, I mean, S3 is still just a trash can fire of vulnerabilities, but most services have matured

 

Jonathan (20:32.91)

I'm going to go ahead and turn it off.

 

Kyler Middleton (kyler.omg.lol) (20:36.633)

are secure-able at this point, and even easily secure-able in some cases. So I think you just have to work with folks to increase their knowledge and modernize their knowledge in some cases, because some people just gave up cloud a decade ago when it was not a secure place for workloads, and help them learn.

 

Jonathan (20:53.39)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (20:57.619)

But I think it's also notable that your developers today are not doing things securely. And I think that's important for people to recognize. People have this idea that like, things are perfect. If I move to the cloud, there's a risk. Things are not perfect. You need to work with your developers. They have static access keys all over their computers. They're often stored or shared. I worked with a DevOps engineer about a year ago who kept absolutely every password on notes on his desktop. And this is not a secure encrypted note. This is the sticky notes.

 

Jonathan (21:04.567)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (21:27.653)

Windows where that was all of the like root credentials for all of our accounts that were and we had to change all of them and it's just

 

Jonathan (21:34.889)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (21:36.367)

If you think that your environment is perfectly secure and cloud is going to hurt you, you're wrong. Your environment's not perfectly secure. Cloud adds transparency, and that makes you think that things are terrible, and it's just because you're looking closer than you were before. So use those tools, use those transparency, X-ray your environments, you will find all the things that are wrong, and then you can fix them. So I think knowing more is not gonna hurt you, it's just gonna help you be more accurate with what you're seeing.

 

Jonathan (22:04.554)

I was speaking to somebody, I think it was on last week's episode actually, where they said that, I asked a question about cloud versus on-premise. And I think I cited DHH in his recent move to his private cloud. And I'm curious to get your take on this with regard to security. You just talked about the concept that our on-premise

 

data center is secure because we can touch it and it feels secure, whereas hosting it on AWS or Google in a different state potentially, even a different country, feels distant and far away and scary. The guest last week made the point that that's often much more secure than your on-premise, especially depending on the skill set of those running your data center and how rigorous you are in keeping things patched. What do you think about that? Yeah. Just...

 

trying to finalize a question and it's failing so edit that part out please no just dive in just dive in I'll leave it to the editor

 

Kyler Middleton (kyler.omg.lol) (22:59.592)

When-

 

Absolutely. Wait, do you want to retake it or I can just dive in? Perfect. Okay. I think a lot of people's first exposure to the cloud was like Gmail and Facebook and Office 365 from Microsoft.

 

And one of our exchange engineers, I was helping them migrate from on-premise exchange to Office 365 to the cloud, which almost every company has done at this point. The local exchange servers are incredibly rare now. And he explained, and I was like, why are you doing this? I've heard the cloud is worse. Like, are you, aren't you risking our security? And he said, do you think we are better at running an exchange server than Microsoft who wrote this tool and like knows how it works?

 

Kyler Middleton (kyler.omg.lol) (23:50.309)

of course the people that like do I think I'm smarter than the entirety of Microsoft at running exchange? Absolutely not. So yeah absolutely.

 

Jonathan (23:58.295)

Right.

 

Kyler Middleton (kyler.omg.lol) (24:01.319)

That's not to say that clouds are not secure, but they are just constantly pentested by dozens and probably hundreds or thousands of pen testers, including you. When you notice strange things, just report them to your, your TAM, to your, to your technical people, to your support staff. And, uh, they will, they will get looked at. Um, and that's just not the same.

 

Jonathan (24:06.931)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (24:25.271)

ecosystem for vulnerabilities as you have with the local software on your computer. Often developers are running old versions of software, your servers are almost always running old versions of stuff, and that's something you need to take a look at in the cloud too. It's entirely possible just to have a virtual machine that's just entirely old and not updated. It's on you to keep it updated, but there are tools that can help you do that, and you should be looking at replacing all of your servers with Docker builds that are regular.

 

rebuilds because as it gets older it gets more vulnerable because people learn more about it.

 

Jonathan (25:01.526)

Yep, yep, cool. Hmm, where else should we go today?

 

Jonathan (25:13.698)

Okay, so edit that pause out please.

 

What got you interested in security initially?

 

Kyler Middleton (kyler.omg.lol) (25:23.251)

I think it's hard. And that's kind of all. I have found my primary motivator for almost all of this stuff is I like to...

 

Jonathan (25:25.023)

Okay.

 

Kyler Middleton (kyler.omg.lol) (25:35.127)

lower the gates for the people that are kept out. And so I was one of those people for a really long time. Like I referenced Stack Exchange because it's just infamously a terrible place to ask a question. You'll almost always get called a name when you ask a question instead of get an answer or an explanation. Reddit's become really similar. It seems like it's just the natural consequence of social media is existing for a while. But those skills are transformatively life-changing,

 

Jonathan (25:38.04)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (26:04.981)

computer skills, but there are fences built around them and I don't understand why that is. And I can't change culture, I can't change that, but what I can do is create content for people that don't understand security but want to learn it and that they have been burned before by people telling them that you asking questions and not knowing means you shouldn't be here, you don't belong here. And that's, that's awful and that's something that I fight against everywhere I can. And I've lost track of your question, but that is, that is

 

me.

 

Jonathan (26:36.222)

Yeah, my question was how you got interested in security. And you said it was hard, so.

 

Kyler Middleton (kyler.omg.lol) (26:38.859)

Totally. I am steering towards things that are hard and where there are boundaries around stuff.

 

Penetration testing, security, both of those things are just incredibly difficult and niche, and there are very few people that are good at it. But primarily, also just for me, finding my own niche of stuff to do, the people that are really good at it are often not very good at talking about it and teaching it, and it changes rapidly. And it's just a difficult place to keep a pulse on and keep people educated. So I'm just trying as much as I can to find complicated stuff that's hard for people to find approachable.

 

and then make it as approachable as I can. And that's not always possible. I can't keep up with everything either, like just like we all can't, but I'm doing my best to just.

 

keep building stuff and keep releasing it. I write about a blog every two to three weeks and I open source all the tools and often it's like I figured out a problem here's a tool I wrote that'll help you and I think I have like a hundred repos public on my github so like I'll pitch this later but just if you solve a problem share your solution it helps people. I learned I don't have any formal education in tech I have a web design minor from college and

 

Kyler Middleton (kyler.omg.lol) (27:56.733)

the internet and reading people's stories. So if you share your story, you're helping people. That makes the world better.

 

Jonathan (28:03.215)

Mm-hmm. I wanted to ask what kinds of activities you do, because you've been hinting at, and we talked about conference speaking, but you've now mentioned your blog. Aside from unsticking people at work, how do you accomplish your mission, or how do you further your mission of making tech security more accessible to people? What are the different ways you do that?

 

Kyler Middleton (kyler.omg.lol) (28:25.899)

Totally, and I find that my real job, my day job, is a really great on-ramp for stuff that I wanna share. So at work, I work with people that are in their verticals and they have a problem that I can't deploy this securely, or how do I test this code and make sure that I can't merge bad code? And I spend a week or two weeks or a month solving that problem, writing tooling, updating our automation to do it.

 

And then, you know, you're not alone. If you found a problem and had to solve it, you're not the first person to run into that problem and you won't be the last. So if you've written a tool that does a cool thing, put it on the internet, write a blog. That's what I do primarily is a lot of my blogs, I call this series, let's do DevOps. And it's just supposed to be as approachable as possible. All my code is shared. I explain what all of it does and where it fits positionally in like your automation, your testing, your deployment

 

code to your environment and like and then at the end it has a link to all the code because you can just go and do it and the goal is just get people doing this write your own code go and play go and test this stuff out and steal from absolutely everyone. When I work with new people in tech they think oh well I don't know how to program because I can't remember how to I can't write a loop in bash I can't write a loop in anything I steal everybody's code and that's what everybody

 

Jonathan (29:51.446)

Hehehehe

 

Jonathan (29:55.201)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (29:55.813)

because you need to look stuff up. That is true of literally everyone you work with. So go steal stuff. Tech is a weird place. Tech is like academia. When you find something novel and very valuable, put it on the internet. Someone will take it. Make sure your work is OK with you sharing what you do. You might want to apologize and ask permission, but do as much as you can.

 

Jonathan (30:16.386)

Awesome. Yeah, I love sharing too. I mean, obviously I'm on this podcast. I blog a lot and have a YouTube channel. I like to share what I learned too. And lately I've been live streaming, going through tutorials to learn something new, which is a little bit, makes me a little bit vulnerable. I feel personally, I feel vulnerable because I'm not in my like smart zone.

 

where I've learned this, I'm an expert, I can teach you. I'm like, I'm learning at the same time and I make mistakes. And I think I did it yesterday and I spent 30 or 45 minutes trying to do something, decided it was the wrong way and it ended up being a one line code, a one line of code, completely different way than my first approach. I was like, okay, that's how you write one line of code in 45 minutes.

 

Kyler Middleton (kyler.omg.lol) (31:06.043)

I love that and I think that's important for new folks to remember. Remember or senior folks when you were new, remember back where you were surrounded by the smartest people you'd ever met and you thought, do I belong in this room? Do I deserve to talk to these like geniuses around me? And that's how everyone feels when they're starting. So I think that's very valuable to show that.

 

These smart people around you, they seem smart because they've done a lot of dumb stuff. They've done it wrong many, many times. They've practiced a lot and you just haven't seen them when they're new at the skill. They've been doing it for years and now they're amazing and they look like I roll out of bed and I know how Kubernetes works. No, I don't. I've spent a lot of time doing it wrong and trying to fix stuff. Ha ha ha.

 

Jonathan (31:33.742)

Mm-hmm.

 

Jonathan (31:50.07)

Yeah. I think it's also really useful to, it's humbling to remember that, I mean, I have however many decades of experience and I still make stupid mistakes and I still waste 45 minutes doing something that was ridiculous. And it, I personally, I forget that unless I'm doing it in front of somebody. So in that sense, it's also useful for me, not even just for the newcomers watching me, but it's useful for me to humble myself.

 

and remind myself that I'm not as perfect as maybe my public persona that I try to put forth, maybe is. So I think it's good for everybody.

 

Kyler Middleton (kyler.omg.lol) (32:28.799)

Totally. I think there's a lot of people that give talks, and me, I've been talking about myself this whole time and how like smart I am, but I think it's important to remember that we're not. We're just working hard and we're doing our best, and that's everybody. So like you deserve to be here. You listener, you deserve to be here, and you can do this too, and just keep messing around with computers. That's all we did. Lots of messing around and you'll learn a lot. You won't even realize it.

 

Jonathan (32:48.974)

Mm-hmm.

 

Jonathan (32:53.767)

So you briefly mentioned that you don't have a formal tech education. You did some web design stuff in university. I'm curious to hear how you educated yourself. Did you use some, like I use the public library a lot, but back before the internet was really big. What was your story? How did you educate yourself? How did you get to the point where you are?

 

Kyler Middleton (kyler.omg.lol) (33:00.725)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (33:16.459)

Totally. I initially built a call center for a phone protection company that have those little cases on your phone.

 

eventually turned that I grew it from like 12 to 200 people, which means you like rebuild it a couple of times. That's a whole different ball of wax having 200 agents taking calls versus 10. And then eventually got into networking and just read all the books and I picked networking intentionally because it doesn't change very fast. Cloud was really scary. I didn't understand it at all. It changes all the time. So I thought that's too scary. I'm going to start with something easier. And the network engineers are mad at me already listening to this story.

 

knew it had been the same since like 1990. TCP has not evolved since 1991 and that's great because that means I can learn it and it won't change. So I don't have my books behind me anymore but I think I have I had...

 

Jonathan (34:08.645)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (34:14.815)

three CCNPs and I sat for a CCIE and I have a couple of CCNAs and these are all Cisco certifications on how to do networking and firewalls and VPNs and stuff like that. And just read. I just read and read and read and studied. And that helped a ton to kind of formalize my knowledge of the basics. And I say the basics, I don't mean that networking is simple. I mean, everything is built on each other. And network is very foundational.

 

Jonathan (34:24.905)

Mm-hmm.

 

Jonathan (34:44.276)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (34:44.929)

a software engineer and you're just writing Java, you should probably understand how TCP works and like what are ports and why are ports important. And I find that almost everything is that basic stuff. You think that like I'll just dive into Kubernetes and I'll learn how to solve this problem. You can, but you're not going to be able to connect those dots as easily as if you start from the ground up foundational knowledge, which is networking, how to loops work, how do you

 

places, what is a VPN, just sort of that basic knowledge. And you'll find that almost all of that cool stuff, I've referenced Kubernetes a couple times because it's so complicated and people, when you try and work with it, it's like, oh, this is a huge new thing. Kind of. It's a software load balancer and a different way to do networking, but it's still based on TCP IP. And so if you know how that works, you can map that over. And I had the same challenge when I started doing cloud. I was told like, it's the cloud, it's different.

 

Jonathan (35:35.992)

Yeah.

 

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (35:44.709)

totally no it doesn't everything just has an IP and it just talks to each other using TCP IP. So your skills no matter where you're at are relevant and just focus on the basics and you can build really cool stuff as you build up. Since switching from network over to cloud I haven't found books that really help. I've done a lot of podcasts. I wrote a course for Pluralsight and that was incredibly difficult but you also get a free Pluralsight subscription and I find

 

Jonathan (35:50.498)

Yeah.

 

Jonathan (36:04.686)

Hmm.

 

Jonathan (36:13.285)

Oh.

 

Kyler Middleton (kyler.omg.lol) (36:14.629)

videos and Pluralsight. So yeah, do it! Do it for the subscription, don't do it for the money. It's great.

 

Jonathan (36:16.337)

Mm-hmm.

 

Ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha

 

Kyler Middleton (kyler.omg.lol) (36:21.447)

And just playing around. Cloud is very approachable. I can't buy a Nexus 7K for eight grand and keep it in my basement. My partner would just murder me if I did that. But for AWS and Azure and Google, you can just go sign up for a cloud account. And for like $5, you can do a whole month of labs. So it's very approachable. And you should be doing it. You should be hands-on. It will help you learn faster if you do it yourself.

 

Jonathan (36:39.79)

Mm-hmm.

 

Jonathan (36:46.646)

Yeah, oh definitely. I think tech is kind of like swimming. You can read about it all you want, but until you start practicing, you're not gonna know how to swim. Ha ha ha.

 

Kyler Middleton (kyler.omg.lol) (36:55.887)

I like that. Yeah, you're definitely not gonna learn swimming from a book.

 

Jonathan (37:01.654)

As long as you can learn a few techniques. Once you know the swimming, you can read an article about a different stroke and then go practice that. But yeah, so I'm not poo-pooing reading. I think reading is great. It's not enough by itself.

 

Kyler Middleton (kyler.omg.lol) (37:15.603)

Totally.

 

I think Linux and cloud often you just like find a guide that someone wrote and it has all these long commands that you will not understand and like maybe find it from a reputable source so it won't delete all the files on your computer. But then just go run those commands and break them down. What are they doing? Why are they? What's a pipe between commands? Like what does that do? And just go do it and see what happens. Make sure to delete it after so it doesn't charge your credit card. But like go play. Go go do stuff. See what happens.

 

Jonathan (37:43.019)

Yeah.

 

Good advice.

 

What else would you like to talk about? Is there anything I should have asked that I haven't? Any other topics you'd like to discuss? We have a few minutes remaining.

 

Kyler Middleton (kyler.omg.lol) (38:01.503)

not really. I could talk about like arguing with experts but I don't know if that's very useful. I think I think it's really fun to argue with my co-workers. Okay let's do it.

 

Jonathan (38:10.382)

Well, let's talk about it. Why not? We have time. So tell me about arguing with experts.

 

Kyler Middleton (kyler.omg.lol) (38:18.699)

Totally. So I think there's, and again, I do my best to frame all of the stuff I talk about from a beginner's perspective, because we were all a beginner once and we're all beginners in all these different verticals. And I find it so much fun to...

 

ask why, like I'm like I'm a three year old. When people say like this is the best way to build this or you have to do it this way, why? Can you walk me through that? What is what are the precept positions that this is based on? Because those are important for me to understand. And all of this is based on just like if you understand the context of how and why something was built the way it is, that will make you a much better engineer than just knowing like how

 

Jonathan (38:37.418)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (39:04.301)

Is there a reason that they can't use this new technology to do it better? And that's sort of one of those skills that

 

sounds very basic, but it's part of how you become a senior engineer instead of just a just a junior or just an engineer is you're not learning how to build stuff anymore. You're learning why. Why are we building it this way and how do we do it differently without breaking it? And that just takes time. I don't have any shortcuts for you. Every tech is different in that in that space,

 

Kyler Middleton (kyler.omg.lol) (39:42.193)

massaging sometimes because people can feel threatened when you're like justify why you built it that way but really that's a part of a DevOps like a healthy culture you have to focus on blamelessness which we haven't talked about but I've also spoken on in conferences that you have to just make it safe psychologically safe for people to go poke stuff and hit buttons and not be fired but you also have to like make it okay to ask why because all of this

 

Jonathan (40:04.142)

Mm-hmm.

 

Kyler Middleton (kyler.omg.lol) (40:11.573)

should be adding comments and say why are you doing it that way? Please explain it to me. And if you are threatened by that kind of behavior that's something you need to work on yourself because that's coming. DevOps cultures require that sort of healthy dialogue, those healthy dialogues of why did you do it this way? So get there and if your culture at your work is not there see if you can push it that way. Start doing tech talks among your team. Start having folks explain

 

built a project and why they built it that way and why they didn't build it a different way. That's a good on-ramp to just starting those dialogues and sort of getting your place to a healthy DevOps culture where other more mature DevOps things can grow.

 

Jonathan (40:56.887)

Very good.

 

Jonathan (41:04.106)

All right.

 

Jonathan (41:08.59)

I'm trying to think of a nice segue here.

 

Kyler Middleton (kyler.omg.lol) (41:12.799)

you want to argue with Kyler you can come to these places.

 

Jonathan (41:15.067)

There we go. That's a good one.

 

Jonathan (41:20.374)

All right, let's get it back in here. So, Kleiler, if people are interested in practicing their arguing skills that you just encourage them to do, and are you a willing participant in this arguing?

 

Kyler Middleton (kyler.omg.lol) (41:34.983)

Absolutely. I am, I am not above the fray here. Bring it on and come argue with me.

 

Jonathan (41:41.282)

How can people get in touch with you to do that arguing?

 

Kyler Middleton (kyler.omg.lol) (41:45.231)

I have an incredibly domain bookmark site called kyler.omg.lol. That is an actual real website you can go to and it has links to everything. I'm very active on Medium and that's a great place to bring you arguing skills because I publish a lot of beginner focused DevOps labs where you can go and actually get the code base, run the tool, I explain how the tool works and why it works the way it does,

 

me why in the comments on those articles.

 

Jonathan (42:18.738)

Awesome. Are you on social media too, or is it better just to follow you on that website and on medium?

 

Kyler Middleton (kyler.omg.lol) (42:26.211)

Medium's my favorite. I was on Twitter until it was acquired and then I have jumped ship like a plague rat and now I'm Primarily on LinkedIn. My name is unique enough. You can just find me based on my name Kyler Middleton or Kyler OMG. LOL, and it has a link right to it

 

Jonathan (42:30.476)

Yeah.

 

Jonathan (42:42.402)

Great, that's great. I'll be sure to send you a request on LinkedIn too. Let's move on to picks. That's something we like to do on this show is just pick something that you would recommend usually. I suppose you could pick something you don't recommend, but I don't know if it's ever happened before. Do you have any picks in mind or would you like me to go first? All right.

 

Kyler Middleton (kyler.omg.lol) (42:57.483)

I'm gonna go to bed.

 

Kyler Middleton (kyler.omg.lol) (43:01.479)

I could totally go first. I have recently discovered what is called a pink drink. I don't think people have a video, but it is bright pink, lemonade and oat milk from Starbucks. It's amazing. And my toddler would probably pick kitty socks. She's almost two and she won't wear socks unless they have a little picture of a kitty on them.

 

Jonathan (43:13.973)

Interesting.

 

Jonathan (43:23.574)

It's hard to go wrong with kitty socks. I'll have to get me some. Well, my pick is going to be kind of anticlimactic because I think everybody already knows about it and if you're interested in it, you already have plans. But I went and watched Oppenheimer, the new movie over the weekend. I haven't been to the cinema in two years since my two and a half year old was born. I think we've been once. So we decided to make it a deal. We went and had...

 

Kyler Middleton (kyler.omg.lol) (43:25.227)

Ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha ha

 

Jonathan (43:48.886)

had dinner and we did the IMAX version. So we went and watched the film and it was fun. So that's my pick for the week. I don't need to say too much about it because everybody already knows if they care. But it's a good movie.

 

All right, well, thank you so much, Kyler. It's been a pleasure chatting. I love the topic of encouraging new beginners. It's something that's important to me too. So I'm really glad that you're doing that. I'm glad you came on here to share some of your mission with us here on Adventures in DevOps. Let's stay in touch.

 

Kyler Middleton (kyler.omg.lol) (44:20.408)

Absolutely. Thank you so much for having me. Thanks all.

 

Jonathan (44:22.626)

All right, thanks everyone. Until next time.