Texas-based technologist Brandon Cross has both a background as an MSP and most recently DevOps. With the IT paradigm shift to AI, there is both a convergence and divergence of MSP workflows. Brandon has crossed the bridge to the DevOps side and is experiencing significant professional success. This 10+ minute podcast explores both sides and what SMB Nation MSPs can do TODAY to, in most cases, reboot the traditional MSP model to include AI on the DevOps side.
It’s a compelling conversation so refill your coffee and soak in the sunshine!

The full transcript is below. You can listen to the podcast HERE.You can link to Brandon HERE.
Harry Brelsford | CEO | SMB Nation & O365nation | 0:05
Hey, nation nation, we are back. It's, we'll talk about this in a moment. It's starting to go roasty toasty down here in Texas. We're sitting at mid-June and we got a couple months ahead of us, so keep the AC on. I'm with a fellow Texan, Brandon Cross, just down the road.
I called my nurse next door neighbor in San Antonio. I'm out in the Austin area, but in this state, we're next door neighbors. It's a big state. Brandon, how you doing down in San Antonio? How are things?
Brandon Cross 0:39
Hey, Harry, doing good, doing well today. Things are things are definitely getting hot down here too, but you know, we've got the Spurs mania that just has passed through the city. Of course, the outcome of that we would have preferred to be a little different, but it's everything is, you know, is what it is. But yeah, San Antonio is rocking and rolling. It's been
Crazy down here for the last few weeks, for sure.
Harry Brelsford | CEO | SMB Nation & O365nation | 1:02
Yeah, well, Spurs are a young team. We shall return. We shall return now. Yeah, yeah, no, I'm excited. I didn't like the ticket prices. I didn't drive that 70 minutes door to door, but I that's I.
Brandon Cross 1:06
That's right, exactly. So.
You know what happened was people were excited from New York when they came into San Antonio because the ticket prices and the cost of visiting the city is so much lower than over there that they felt like, you know, they were getting the deal of a lifetime here.
Harry Brelsford | CEO | SMB Nation & O365nation | 1:32
Yeah, yeah, tell me about it. Hey, let's get down to business. So you're a frequent poster, which is more or less how I met you with some of the good work you're doing in the MSP community and the DevOps community and so on. Appreciate you. The topic today is MSP divergence.
did a piece a little while ago about MSP divergence, and it was basically DevOps versus cybersecurity. So over to you. What are you thinking?
Brandon Cross 1:57
M.
Sure, Harry. So what, you know, I noticed, because I've been in the MSP space for a long time. Okay, I've started my first MSP back in 2004 from a break fix environment that I had put the, I'd cobbled together when I was in high school. And so the, you know, the MSP world has
has kind of ridden the gravy train. And now, you know, things have changed, right? MSPs have to evolve. And one of the areas, and this isn't even the most recent area of evolution that MSPs are facing, but a few years ago, I started to roll out, I'd sold my MSP.
Harry Brelsford | CEO | SMB Nation & O365nation | 2:25
Yeah.
Brandon Cross 2:42
and I was rolling out and trying to figure out what the next thing was. And I thought it was going to be cybersecurity for me because I was so heavy into cybersecurity work when I was running my previous MSP that it seemed to be like the direction to go. But I actually ran across the DevOps cycle of things.
And that is an area where I actually became very focused and started to grow. And so that's where I think MSPs can diverge one of those two directions. There's other directions they can go, you know, be in a VAR, vertical vendor for some, you know, line of business application or something like that. But really,
The 2 major lines they're heading towards is are they securing environments or are they managing software deployments that organizations are standing up that are custom applications they're running in-house?
Harry Brelsford | CEO | SMB Nation & O365nation | 3:36
Yeah, yeah, I just read an article. Good timing today to meet up with you again mid-June, folks. But I doom scroll at 2 A.m. So, you know, Brandon, don't ever get old. It's goofy when you're older and your sleep patterns. So there I am doom scrolling.
And there was a piece about AI is going to eliminate apps. And it was an interesting conversation. I don't completely agree, but it seems like that's one of the DevOps conversations, right? Is this going to take down the
The context of this article was, you know, you're getting tired of SaaS fees, you know, $99 here, $100, a lot of $100 hollers with SaaS, right? And is this going to take that down? Any thoughts on AI versus applications over in the DevOps side?
Yeah.
Brandon Cross 4:34
Absolutely, because in the past, you know, building an application was a very, very big challenge. It was a huge task, okay, managing it, setting it up, writing all the code, everything was very complicated. Now, in this kind of like newer sort of AI driven, I don't want to say vibe coding world, but in a world where an organization can sit down
Harry Brelsford | CEO | SMB Nation & O365nation | 4:52
Ha.
Brandon Cross 4:55
and they can give somebody inside of their company a directive and that person can log into a website like Replit or Base 44 or Lovable, there's a variety of systems and start to build something that resembles the feature set that they're already paying for. Then these organizations are moving over to these
in droves. And that's driving, I think, the actual opportunity for MSPs in the DevOps space. Because when an organization launches some containerized service that they just created in Lovable or something, then they don't really know how to properly manage that.
Harry Brelsford | CEO | SMB Nation & O365nation | 5:33
Yeah.
Brandon Cross 5:37
And that's where DevOps is going to come into play.
Harry Brelsford | CEO | SMB Nation & O365nation | 5:40
Mhm.
Yeah, what I'd like to do, and I think you and I both, you know, we have a mentor inside of us to, I don't like the word coach. There's too many coaches in our space, but how about, how about encourage people in our space to keep their chin up and there's always opportunity. And I guess one of my lines is,
When I read that, I've gotten to know you pretty quick. It's always been this way. You know, that we've always kind of had paradigm shifts in technology and, oh my God, the sky is falling. And, you know, whether that was the hysteria over Y2K or, you know, clouds going to wipe out.
The the laptop, but it's always been.
Brandon Cross 6:21
Yeah, exactly.
You're right. Those have been huge fear-driven, you know, scenarios. Today, there is the AI one is right there. And it is something that will be very disruptive to a lot of people, but it's also anytime you get disruption, you get opportunity.
Harry Brelsford | CEO | SMB Nation & O365nation | 6:43
Yeah, yeah, exactly. And now, speaking for myself, here, and maybe you can coach me for lack of a better word. So, you know, I had the good fortune or misfortune. When I first moved to Seattle, I was an adjunct instructor at those
you know, trade institutes like the, well, even before the Alaska Computer Institute, and then down in Seattle Griffin College, you know, the old Tuesday, Thursday night for two hours at night. And these were good people. These were working people, you know. And I mean, like Domino's delivery drivers who were just trying to get a step up in life and learn at the time, you know, and you were there, man, the M
Brandon Cross 7:14
Yep.
Harry Brelsford | CEO | SMB Nation & O365nation | 7:27
CSE certification, so the Windows, yeah, Windows NT and good, good people, good people. And because I taught at Griffin College at the time, you know, one of the side benefits is free tuition, right? Like, hey, Harry, do you want to sign up for Visual Basic or C, or well, I guess we just called it C.
Brandon Cross 7:29
Yeah.
Harry Brelsford | CEO | SMB Nation & O365nation | 7:48
plus or C then.
And here's what I found. It was not a natural act for me. I basically dropped out of both. It wasn't a good use of my time. I was newly married and I needed to be mindful of, you know, home time, family time. And, but it wasn't a natural act. I mean, dude, I got my *** kicked.
And Visual Basic wasn't even that hard. So how do you respond to that? I'm not alone, right? A lot of MSPs came up through infrastructure and, you know, SMS and reboot and, you know, the registry and HKEY, the hives. I mean, that, I still have.
Nightmares about that, Snitz. Any words of wisdom, because I just thought, you know, it's just not what I do, dude, was coding at that level.
Brandon Cross 8:42
You know, software development is really difficult and takes a particular type of mindset. Infrastructure and systems people oftentimes have a different type of mentality, a different way of thinking than software developers do. And that's why there's a big divergence between those two communities. So one of the things that AI has done is it's given SysOps people an opportunity to essentially become
DevOps without trying. The beauty of the way that you can run, you know, some of your operations today is that a lot of answers that would otherwise take you a long time to get can be quickly gotten by using systems like Claude Code. So, and Claude Code even runs on PowerShell, so you can literally install it on a system and just say, here's what I'm having a problem with, figure it out.
and then it will tell you exactly what commands it's running every single time, which you can go verify and validate. So there's ways to bridge the gap. When you're developing software now, you prompt for it. You basically, it's about connecting the interconnected layers. It's about, if you understand what an API endpoint is and how it receives, you know,
Harry Brelsford | CEO | SMB Nation & O365nation | 10:04
Yeah.
Brandon Cross 10:05
what used to be that complex sort of the semantics of software development and inserting functions and parameters and scopes and keeping all that orchestration in your mind doesn't exist in a lot of the AI apps because you're looking at the API endpoints.
And, uh, and and and you're looking at the database tables and how they connect, and that's that's practically it.
Harry Brelsford | CEO | SMB Nation & O365nation | 10:32
Yeah, yeah. Any final thoughts? We're almost at about time. I told you in rehearsal that we do like to be mindful of time because I'm not a well-known Austin podcaster, no names please, that has a daily 90-minute show. And even, I don't even want to listen to myself for 90 minutes. So any closing thoughts? And I'm going to put your LinkedIn
Profile link in the blog.
Brandon Cross 10:58
Yeah, get ready for a lot of garbage AI apps to show up at your clients and get ready for people that are setting up automation of those systems at the user level to start showing up behind the scenes. And
have a plan for how to govern that. And that's what I would say is my final thoughts.
Harry Brelsford | CEO | SMB Nation & O365nation | 11:24
Yeah, great. Hey, stay on the line. I want to talk to you for a minute, but we're going to stop recording. So Nation, Nation, before you know it, we're right on top of the 4th of July weekend. I actually have a fun podcast coming up with a well-known hacker along the lines of Kevin Mitznick, who unfortunately we lost a couple of years ago.
But we both started with the Apple 2 Plus. So folks, holiday week, I got a giggle for you. And thank Brandon, thank you for your time.
Harry Brelsford | CEO | SMB Nation & O365nation | stopped transcription