Nov. 2, 2025

How MSPs Can Stay Relevant with AI (EP 920)

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How MSPs Can Stay Relevant with AI (EP 920)

Discover how ASCII Group is guiding managed service providers to stay ahead of industry change, with new AI strategies, community-driven education, and exclusive member programs.

Uncle Marv welcomes ASCII CEO Jerry Koutavis for a candid conversation on why vendor-neutral collaboration is the key to thriving in a rapidly evolving MSP landscape. Listeners will learn about ASCII’s 40+ years of industry leadership, how to approach client discussions around AI, and why moving “from VAR to MSP” is only the beginning. The episode includes a preview of ASCII’s AI Collective and provides insights into building trust and optimizing service delivery amidst constant change. 

Why Listen:

  • Learn how to kickstart impactful client conversations about AI
  • Discover ASCII’s vendor-neutral, collaborative resources for MSPs
  • Hear about upcoming AI Collective webinars and member code sharing
  • Get insights on navigating rapid tech change with confidence
  • Connect with a CEO who leads 1,500+ MSPs nationwide

Companies, Products and Books Mentioned: 

SPONSORS:

SHOW MUSIC: 

SHOW INFORMATION: 

Hello friends, Uncle Marv here with another episode of the IT Business Podcast coming at you live from the ASCII Cup, the last ASCII EDGE event of the year. We are in the city of Philadelphia and I am joined by the CEO of ASCII, Jerry Koutavis. Jerry, thank you for taking a few minutes out of your busy day to join me. 

Oh, this is great Marv. Marv and I really appreciate the opportunity and it's just wonderful to be in this city for the first time as we wrap up our event series and just looking forward to next year. Is this really the first time it's been here? Yeah, we've looked at Philadelphia as a market that we could have an event at but we've always, you know, when you build out events there's always some variables that come into play and we never had a chance to really firm up and solidify having an event here but it's been great. 

Obviously, the attendance is strong here, the engagement is really high and so this is something that the team looked at and it's great to see the results. So yeah, we're super happy. Okay, I'm actually surprised that this is the first time here. 

Of course, I got chastised earlier by some members because, you know, everybody always says, oh you're going to come to my area and not reach out and I'm like, you're in Jersey, that's like two states away and they're like, no, it's next door. Right, right, exactly. And we do got some people from New Jersey that made the trek which is not that far like you mentioned.

Head vendors come from Boston. I mean, it's, I didn't realize how close it is to everything and I just use the excuse, I'm from Florida. Yeah, it's a different market up here. 

Obviously, there's a lot of MSPs that are doing business across state lines given the proximity but yeah, again, it's just been wonderful to see sort of the people showing up and the participation has been great. So yeah, just wonderful. Nice, very nice. 

Well, let me ask, I mean, this is the last event of the year. I can tell you this, great turnout, the room is full, standing room only in some of these sessions here. So it's been great but I guess the question really is, you know, where do we see ASCII looking at the history? I mean, ASCII, you know, 40 plus years, the oldest, you know, group of its kind. 

Everybody's trying to, you know, do the next best thing. Everybody's trying to, you know, grab eyeballs and, you know, grab attention and stuff. ASCII is still here, you know, plucking along. 

Why do you think that is? Well, I think it's, this is going to sound a little bit corny. So there's an element that our team has been instilled with our team and also from the owner for many, many years is that we really truly care about where the industry is and where they should go. So the reason why we've lasted for so long is that we have optics into where the concerns are for MSPs well ahead of when it actually gets to their sort of attention, in a sense. 

Okay. So we're at another point today where there is a concern for the industry and so for our members to remain relevant and for the industry to remain relevant, we have to clearly see what we should be doing now as we prepare for future services and future revenue. And again, this technology evolution that is taking place with smart systems and the ability to do things quickly without a lot of previous weight, if you will, in terms of programming and what have you, all this is going to be such a means for our industry to grow. 

But we, as an industry, have to recognize that for this to take place, we simply just can't look at how we operate today as sort of the best way to say it is that if we maintain the way that we operate today and just bolt in some of these new opportunities, it won't work. We have to change the thinking of how we have the relationship with the client. So AI is going to push us in that direction out of our comfort level the same way that the market was pushed for us to move from a VAR to an MSP. 

So this is a different flavor completely, but it is something that everyone has to do and obviously everyone's talking about it, but we're going to make sure that our community sees things in action, bringing members into the fold that actually have created solutions, showing and sharing back to the community how those things were done and implemented and executed, and giving people the opportunity to simply learn from each other like Aspen's always done since the beginning. So nothing really changes other than us making sure that we see on the horizon where things are going and then we pay attention to it and then provide the resources, direct feedback from the membership in terms of what they're doing, and that's going to lift everybody up. Right. 

Now as part of that forward-looking mentality, how much of that is coming from your relationships with vendors because you are vendor neutral, so you're talking to everybody, and how much of it is coming from members? Yeah, I think that we have this sort of, you know, we hear feedback and obviously insight from the vendor community and at a high level we're gleaning data that shared with us, but you know we're more in tune to what is actually happening within the membership and what they're seeing in the market. So it all plays a role in us sort of molding a picture of where we should be going as a community, but we weigh heavily in terms of what the members are seeing in the marketplace, what is taking place, and quite frankly you will also have a gut check internally. We know sort of where members are in the transition to start offering services on AI or start building a better relationship with their customers. 

So we have a good beat on that just in terms of how we ask certain questions of the community. So combining all that data, we really do have a framework of building out, okay, if we see these problems and we're hearing it as well in the marketplace, this is sort of the prescriptive strategy that we need to start delivering to the members. So taking all that, you know, into sort of netting it out, we're going to make sure our members are staying relevant.

That's the key thing. Can they stay relevant in the era of AI? And they can. They can. 

So we're at our last event in Philadelphia, eight events in, every time we ask questions of the audience, where they are in this journey, and more and more people are raising their hand, and it's coming up quicker in terms of like where we were in February this year compared to now. It's amazing to see that people are getting out of their comfort zone and going down the road of like, okay, this is something that I have to start to explore. But yeah, it's probably going to be the most exciting time and the most scary time for our industry all at once. 

Yeah, we are being told that we need to jump on board. We need to add this to our portfolio. We need to find a way to help our customers with this. 

But at the same time, a lot of us don't even know the technology ourselves. Do you have any sort of early feeling about, you know, how AI and emerging tech, because this is going to, you know, this is going to open the doors to other tech as well. But do you have any thoughts about how all of this is influencing the future of the managed services industry? Absolutely.

So we have, and what's great about asking what I love, and I'm technically dangerous, but I am a tech head. I love technology. I started off as a programmer and then shifted into marketing. 

But, you know, my trash eating that I used to use when I was in high school, there's something about technology. And so the reason I bring this up is we're at a position where we see technology coming to us early on, and it's continually coming to us early on. So for the audience that may not know who ASCII is, you know, Arnie Bellini was a member of our group. 

So Arnie showed me ConnectWise when nobody knew what ConnectWise was. And so I'm bringing up that as an example. The same thing with Kaseya, Datto, and you go down the list.

So we're seeing and having conversations with companies that are going to approach this industry and help MSPs, and we're having those conversations now before it's a brand name. So why does this all matter? It matters because the speed of which things are moving, I feel, and I just came off the stage when we were talking about this, is that we all need to slow down a bit. And we need, right now what's happening is there's pressure on our industry to move. 

You're going to be outdated if you do not take this approach or start looking at us. And we get it, we understand. But that same pressure is happening at the end users.

So your customers are under that same sort of ideology in terms of like, you have to do this, or you're going to be extinct. But what's unfortunate right now, if you can just visualize a 50s dance in a gymnasium, you had all these boys lined up on the wall, and all these girls on the other side of the gymnasium lined up on the wall, and everybody's in the same boat. They want to dance, but they just don't know how to start. 

And I'm telling everybody that is listening to this right now, get off that wall, and walk over and start having these conversations, because we're all in the same boat right now. And this is probably the best opportunity to start building a relationship with your customers where you know, it may not be where you want it to be. This is a means to create a foundation to have a conversation, because again, we're all kind of in this together in such a weird way. 

When we moved it from VAR to MSP, that was more advantageous for us. Because we had the tools that our clients could not get. That's right. 

It's not the same today. Correct. So now we're in the same boat. 

The end user needs to understand how they need to develop our utilize these new systems, and we do. And we're not going to get ahead until we both have sort of a conversation, and it could be simply this. We're tracking AI, and because it's moving so fast, we want to make sure as a baseline that there are some security measures in place with you and your staff. 

Do you have an AI policy? No. Okay, let's establish that. Do you know what your staff is using related to these tools? I don't even know if they're using them, but maybe you run a report, and then the CEO of that company is going to go, wow, I had no idea. 

And some of these tools may not necessarily be the best for your business from a security perspective. That's the starting point. That is literally a means to have a conversation that's productive. 

You don't have to go in there and say, listen, I want to sell you an agent, and let's figure out all the plumbing between all these systems and creating these smart API webhooks and connections to deliver a product. Let's just, as a baby step, let's just start with security, which is our, that is our wheelhouse as an industry. Let's start there, secure us as you, as the authority of that client, and then that is the baseline to have future conversations when they go, okay, you know what, we ran across this, I know you have a problem with X, Y, and Z. I think we may have a solution. 

Let's talk through it. Regardless, that's in the future, but starting a baseline is so important right now, and it is primed, completely primed for you to build a relationship in a conversation that is not necessarily being had, I say probably by 80% of the industry right now. So you mentioned baseline. 

I had a conversation with a client just a couple of weeks ago. They're a law firm, and they are all about, we've got to get AI or else we're going to be left behind, and we decided to have a conversation. Why do you need AI? What do you want it to do? And come to find out, really what they want is the automation part of AI, and I told them, I said, well, you realize your case management software has a lot of that already built in, you're just not using it. 

So before we go adding AI, let's take advantage of what you do have, then we can introduce AI that can take advantage of all the stuff that you already have, and just those discussions, I mean, you made a comment earlier that I was going to ask you about is, you know, you said that a lot of our issues are not just the technology, it's speed. It's how fast we are having to adapt. Let's just say six months ago, eight months ago, we're in October, the buzzword is, you're going to be a prompt engineer.

That is not relevant right now. You don't have to be a prompt engineer. These systems are intelligent at the point where you're going to be able to put something in, and then it's going to do all the prompting behind your question.

Now, great, you're going to have to create a starting point, you want to make sure that starting point is very efficient, but that's not what a prompt engineer is about. So that whole segment of what the market was saying to us is gone bye-bye so quickly, okay? So again, it goes back to the speed of things and how we need to pause. So these systems right now aren't sophisticated to the point where I can go in and tell it that I want to build out this particular application. 

If it's a low-end application website, yeah, it can crank it out, but once you start getting into more details and what-have-you, it's not there. It's not there. It will get there, but it's not there yet. 

So I think that as technology is evolving and they're fixing these particular systems and platforms and what-have-you, we have to just do blocking and tackling. The blocking and tackling is, one, talk to our customers. We're in the same boat. 

We're seeing a lot of interest in AI, but we are concerned about security. We want to make sure that your data is not getting used in these training systems, and more importantly, do you have a handle on what your actual employees are doing? Let's look at that first, okay? And then everything's going to kind of come from that, and you'll be surprised. As we're having these conversations, who knows where we're going to be from a service perspective once these platforms really settle into what actually they're going to do well and then how that's going to help us with our customers.

All right, you took that question right out of my playbook here because I was going to ask you what some good actionable steps would be, but you just mentioned it there. Let's go ahead and transition real quick, because I know we did not talk to ASCII at all, but as this is the last event of the year, obviously your work doesn't stop. Do you have anything that's already on the horizon that you can talk about for, you know, the next few months or the next year? Yeah, we do. 

I appreciate the question. So what we're going to be providing to the membership is a whole webinar series called AI Collective, and this series is going to start with some key platform providers all on one virtual panel talking about where they see the industry going and how they're utilizing tools currently to help MSPs. So it'll be a thought leadership panel. 

Hopefully we'll get into the speeds and feeds debate between the different platforms, but I don't think it's going to be. So we're going to have that, but what's interesting is we have members of the group right now that are doing things with AI, building dashboards, building integrations, building ticket triage optimization, of marketing systems, a variety of things. All those people, and if you don't know who ASCII is, ASCII is a community that is all about sharing and growth, and these companies are willing to actually share how they build it, show you the process, show you the tools, so you can get an idea like, oh, I can do this. 

And we have members right now that are sharing the actual code on certain things that they're doing right now. So that series is going to take us into well into the year in 2026, and then there's some other things that we're doing at our events for next year, going back to sort of that client conversation. So we're going to have a lot of content there on how to approach the client, how to best position yourself to gain the intel that you need, so you can actually help them out and monetize additional areas based on this conversation. 

So this is all going to tie together for us to actually help our members understand these systems, examples of how these systems are used by our members, and then allowing the members to actually gain access to code to understand how they can actually quickly adopt some solutions for themselves and tweak them as they go on this journey with us. All right, well, folks, you've heard it there. There's a roadmap for 2026. 

No wonder you had a bunch of AI stuff in your head. You guys have a roadmap already done there. So as you can see, folks, ASCII group, basically a resource hub, I mean, for managed service providers, collaboration, education, thought leadership as to where you should be looking down the road. 

Be sure to take a good look at them. If you are not a member, consider being a member just, I mean, to be a part of the conversations like we just had. And, of course, oh, yeah, there's discounts, there's programs. 

What is it, over 70 programs that you can be a part of? Yeah, there's over 70 programs, and I know I was harping on some of the forward-looking stuff, but ASCII is, basically, if you're an MSP out there doing $50 million or under, we have people in the group at every level that is looking at us as a resource. It is the ability to get questions answered, connect with people that can help you with projects, and ASCII, from a headquarters perspective behind the scenes, is influencing the discussion, helping you with educational direction, with experts that are coming out of the community, or third-party experts that we feel have good strategy and content that we want to share with the group. And this sort of automation of people sharing and learning and passing business back and forth, where vendors aren't part of that conversation, so it's still private, it's something special, because, unfortunately, people use systems that I feel may not be the best for them long-term, because you don't know who's giving you that advice, and you don't know if that person is a vendor or an MSP. 

There's no... Shiny object syndrome. You got it, you got it. Our conversations aren't conversations that other people in the group look at as opportunities for poaching, or looking at opportunities for potentially positioning for business in the future. 

These are owner-led conversations where their interest is the same as yours. They want to help you, and you have a resource to get help, especially in a market today where things are moving so fast that it's important that people truly, truly look at where they are and where they need to go, given where the market is, ultimately. And that is optimization, efficiency, and the manner that you're going to have to have a business strategic conversation and relationship with your clients. 

All right, well, folks, there you have it. Jerry Koutavis, CEO of the ASCII Group. Be sure to check them out. 

I'll have links in the show notes. ASCII.com. And, you know, you can see Jerry at a lot of industry events, and grab him and get inside the mind of a CEO that is leading 1,500 MSPs in this organization. Jerry, thank you very much for your time, sir. 

And that'll do it, folks, and we'll be back with more from ASCII Cup in Philadelphia. Holla!

Jerry Koutavas Profile Photo

Jerry Koutavas

President

As President of The ASCII Group, Jerry Koutavas is responsible for creating resources and services aimed at helping IT and managed service providers better manage their time and their bottom line.