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Episode 101: Trading Fours
Just in time for Thanksgiving, Erick and Rich celebrate 100 episodes of MSP Chat by trading thoughts on the show’s most thought-provoking, headline-grabbing, memory-making conversations. Then, just for fun, they share their favorite “One Last Thing” segments of the podcast in a conversation featuring return appearances by Charizard the Cheeto and Wally the emotional support alligator.
Discussed in this episode:
Episode 5: Navigating the Managed Services Landscape in the Cloud Age
Episode 20: Cracking the Code on MSP Relationships
Episode 27: Why M&A is Still OK for MSPs
Episode 59: End Game of End Games
Episode 66: It Takes a Community to Secure an End User
Episode 71: Don’t Buy Voldemort
Episode 74: No Timmies Allowed
Episode 88: From the Server Room to the Boardroom
Episode 95: Kirk Versus Picard
Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.
Transcript:
Rich: [00:00:00] And 3, 2, 1. Bo Blastoff, ladies and gentlemen, welcome to another episode of the MSP Chat podcast. Your weekly visit with two talking heads, talking with you about these services, strategies, and success tips. You need to make it big and manage services. My name is Rich Freeman. I’m Chief Analyst at Channel Mastered, the organization responsible for this show.
I am joined on this festive occasion in multiple senses as I am every week by our CEO and chief strategist and channel mastered. His name is Erick Simpson. Erick, how’s it going?
Erick: It’s going great. Rich discounting down the last few hours before you and I take a well-deserved. Short break.
Rich: So we are recording this episode the [00:01:00] day before Thanksgiving.
It is due to reach the world the day after Thanksgiving. So by the time you are enjoying this program Erick and I will have eaten way, way too. In fact, we’ll still be digesting. Erick is my prediction. Yeah, that’s my plan, rich. Yeah. Yeah. No, Fri Friday I’ll be on to the sandwiches made with the leftovers by by Friday, so Absolutely.
Erick: Absolutely. They always taste better that way. Oh, they’re so good. Yeah.
Rich: This is. Technically episode 1 0 1 of MSP Chat not even technically. It is episode 1 0 1. As we told regular listeners and viewers last week during episode 100, we very much want to celebrate this milestone that according to the statistics, only about 5% of podcasts ever reach only about 5% ever make it to 100 episodes.
We have made it there. We are very pleased we. Thank you, all of you. Whether [00:02:00] this is your first episode, your fifth, your 100th, thank you for going on the journey with us this and every year around this time, the Thanksgiving week, because it’s a short work week, we do an abbreviated episode of the show.
So we decided to do our episode 100 celebration during episode 1 0 1, which was gonna be abbreviated anyway, and if you’ll indulge us, we are going to reminisce. We’re gonna get a little nostalgic, we’re gonna look back at those 100 episodes and just talk a little bit about some of the many interesting topics we’ve covered and issues we’ve talked about many of which remain relevant in the world of managed services.
So we’re gonna, we’re gonna trade for, as they say. We’re gonna go back and forth Erick, on this. Should I go first? Should I kick off? Lead on my friend. Let’s,
Erick: let’s see what you got.
Rich: Okay. Okay. And I, you may accuse me of cheating here. This is a bit of a twofer, but most of the time what we do on this show as the regular audience [00:03:00] knows, is we’ll talk about something that’s happening in the news.
You’ll provide a managed service, a success tip. We’ll have an interview that’s a thought leadership conversation. Every now and again, though over the course of our 100 episodes, we have actually made news ourselves and in the interview segment. And so what I wanted to kick off with as a twofer is right at the beginning of this year, January, 2025, we had an interview with Fred Cola of Kase.
This came. Two weeks after he and Kaseya had shocked the world by announcing that he had stepped down as CEO, he was gonna be vice chairman. As far as I know, Erick, the very first public appearance that he made after that announcement was on this podcast. And I can tell you this, we, we do this podcast together.
I write a blog called Channel Hallock. I wrote an article based on the conversation with Fred Cola that got massive traffic because no one had heard him. Talk about, why he left and what comes next, and so on. So [00:04:00] that I thought was really significant and interesting, the kind of thing that we do for the audience.
And then a few months later we were able to get his successor, Ranya Sukar on the show. And over the course of that conversation, we got into all sorts of interesting things about. MCP and APIs and stuff that kind of became public knowledge during DattoCon months later. But I, we got her talking about stuff that she hadn’t really talked about at that depth beforehand.
And if you need any more good reasons to be a an MSP chat regular here are two great examples. You will now and again, get stuff that is newsworthy and you just don’t get anywhere else.
Erick: Awesome, awesome. Fer there, rich. I’ll give you that one. I’m gonna take a little bit of an opposite position, and I’m gonna talk about some MSPs and MSPs, former MSPs that have gone on to help other MSPs.
My first one, it happened in episode 62, [00:05:00] and we were joined by the well-respected, well-known Nigel Moore. Of the tech tribe and we had quite a freewheeling. I would just say Ozzy impacted conversation. It was very fun. Nigel, is, can be a little bit irreverent, but his experience and his insights are just spot on.
I had a lot of fun interviewing Nigel and, an old friend of ours, rich. And it’s always really interesting. To speak to an MSP kinda like myself, that has crossed over into helping the MSP community and vendors raise, the rising tide concept lifting all boats.
So I just really appreciate Nigel for doing what he does for MSPs and vendors and helping us, steer and modify and improve. Channel for everybody as well as, the end customers that we all serve. So that was really fun. If [00:06:00] you wanna catch that, it’s episode 62. It’s paddled.
Rough is enough.
Rich: Nigel is one of those rare examples of a person who is both extremely intelligent and informative and a whole lot of fun to be with. And yeah, I, I remember enjoying that conversation with him a lot. And the other thing I’ll say, if I remember right. Because he was doing it from his home office in Australia.
I think it was like 8:00 AM for him, if not early. He kicked the day off for us to come on the show. So we appreciate
Erick: that too. Yeah. And he might’ve either just come out of the surf, ’cause I know he surfs every morning or was getting ready to go in the cert before starting his day. Yeah that’s Nigel’s day.
Rich: My second pick here you picked an MSP. I’m gonna do the same thing. What was it? It was episode 27, so this is a long time ago. June of 2024. We had two figures from the MSP world on the show. Peter Melby, the CEO of New Charter, a big, very well known MSP [00:07:00] Rollup. Craig Fulton an advisor at Evergreen Services Group, which is also a roll up.
He for many years worked at ConnectWise. He was chief product Officer for a while. Part of why I wanna bring this up, it’s a fond memory for me. So I one day just got this brainstorm, it would be interesting to talk to a couple of these roll-ups and get some insights that might be useful for our audience.
And I thought who do I know? How about Craig and Peter? I sent invites out each of them individually wrote me back and said you understand the other guy is a competitor of mine, right? Yep. And I thought, no, actually I should have thought of that. I didn’t neither one of them wanted to back down or back out.
They came on the show not quite knowing what to expect. It was a really phenomenal conversation. And then you fast forward a little bit, so that’s June, 2024. March, 2025, I was at a [00:08:00] conference in Austin, Texas that Evergreen hosted, and one of the speakers was. Peter Melby. It’s like I, I brought peace to Craig and Peter such that even though they do compete to acquire MSPs, they collaborate as well.
And so I feel really good about that little bit of Kumbaya brought to the world by MSP Jack, IMSP chat.
Erick: I’ve thought about that several times since Rich, and I’m like, yep you actually, invited these two. Into the octagon and they came out better for it, and they were very respectful and supportive of each other.
During that call. It was, you and I we talked about it, before the show. And we’re like, okay, let’s see what happens. And it was a great episode. And yes, and since then we’ve had more folks from, these types of ancillary. Companies and organizations that are now also part of this MSP channel, right?
And you’ve been to, several [00:09:00] events from, for m and a and PE and Rollup and all that other stuff. So we’re seeing the inflection of not simply bringing, two folks that might have been competitors, the other, but maybe MSP chat is helping, elevate the conversation and open the door.
For more of these types of events and conversations and collaborations. And of course we love reporting what’s going on in, on that side of the fence for our MSP listeners as well. So I’m gonna give you more credit than even you humbly wanted to note there.
Rich: I like that thought very much.
Erick what your turn, what’s your
Erick: alright, so one of the other really fun. Interviews that we had was with Matt Lee, PAX eight’s Senior Director of Security and Compliance. Also a, an MSSP came from our, my world. On the other side. The episode is episode 71, don’t by Voldemort.
And yes, I think there might have been a couple of cuss bombs. Matt dropped there during that [00:10:00] interview and it was a really thought provoking. Chat about everything from, agentic AI to cybersecurity and some, some in insight that Matt brought that’s that reflected that MSPs and SMBs were, are going to have better cybersecurity and compliance than enterprise organizations.
That stuck with me. And this is the opportunity that we’re seeing now. I think we reported recently on one of our recent MSP chat podcasts about the potential for cybersecurity and growth in the SMB, which will be eclipsing that in the enterprise spend recently. If you’ll recall, rich, that episode is seven episode 71 titled Don’t Buy Voldemort, a Direct Quote.
From Matt Lee
Rich: and just by the by. Yeah. The episode featuring the fact that according to [00:11:00] Microsoft, based on data from IDC total Global IT spend by SMBs will be greater than total Global it spend by enterprises next year, 2026. That was episode 100 the last show that we did. And yeah.
Great pick. Matt Lee episode you’re talking about there that the, the reason Matt is both beloved and respected, the way he is in the MSP community is ’cause he always shoots straight with you. And I, that, that’s not the first time I’ve interviewed him. I’ve interviewed him since.
The thing that always strikes me is. In any conversation, any interview I do with him at least once, and usually more than once, he’s gonna say something that catches me totally off guard. And the example you cited there about, smb SMB is having better security is a great example of that.
It’s huh, that wouldn’t have thought that myself didn’t see that coming.
Erick: Yep, yep. Yeah he’s he’s he’s the great dropper of. [00:12:00] Interesting soundbites, that’s for sure.
Rich: Okay, I’m gonna go here. Here’s number three. For me, and once again that I’m shameless, I’m cheating. It’s a twofer because twice now, I think both this year, 2025, we have brought live panel sessions, record in front of a live audience at an event onto this podcast as a podcast segment.
We did one of those. At at Dacon recently, and then the first time we did it was at Kaseya Connect, I think in the spring. And both times we had really great panels on stage. And it for, I think for us, but I hope for the audience as well. There was something just really. Exciting and live and dynamic about getting up in front of real live people and audience and just that energy of the reaction from the audience and and the input from the panel people speaking with each other and as well as speaking with us.
It was just really great. The only two [00:13:00] times we’ve done that so far I enjoyed it enormously and I think those are both really good episodes.
Erick: Absolutely. I think it’s it brings, like you said, it’s a unique energy. We’ve got the, the live audience there with reaction. Too bad we don’t have mics like getting their response.
’cause we’re asking them for feedback and things like that. And, just the prep beforehand, all right, we’re going live everybody. We want you guys to go crazy. And, it doesn’t actually come through on the recording of the podcast, but they are going crazy and yelling and clapping.
And it is great to have. The insights of, it’s four interviews in one. We normally have, one or two interviewees, maybe three on the MSP Chat podcast, but having that live event recorded right there with four, three or four well-respected MSPs and this getting that real world knowledge from them, from anything from, ai, how they’re leveraging ai, how they’re improving their service desk efficiencies.
All this. Really actionable intel is being shared. Again, just [00:14:00] another example of MSP sharing with other MSPs and boy at MSP Chat Rich, we wanna make sure that we are promoting those voices and doing more of those types of live events because it does help expand and broaden that message.
Of course, the more that we promote it in social media and the panelists and the sponsors of these. These sessions that we do are helping to promote it just gets the word out. So again, doing our part for the channel. You’re up. Third choice. Alright, so my next choice is an episode we did episode 77 and it’s titled 75 Days of Uptime.
In that episode, what was really cool was the discussion that you and to me, the couple things, one that I really enjoyed and I’m, always keen on having discussions around is talking about the trade-offs between MSPs using these all [00:15:00] inclusive managed services bundles and platforms.
If you recall, rich, rather than going the bespoke, best of breed. Bundling and the unique opportunities, but also the unique challenges, the pros and cons where, hey, if we got a bundle from one provider, let’s call it, say a K 365 and user or versus ConnectWise bundling things together or any other vendor.
It makes it easier, I think, to package, deploy price and support. But there’s also that risk that’s, one single point of potential failure or risk from a cybersecurity perspective. So there’s trade offs. We discussed all that, and we also discussed when it makes sense to add some bespoke things and how MSPs are differentiating themselves and getting maybe the best of both worlds.
My thought if I jumped in and wanted to become an MSB [00:16:00] tomorrow with a, with an eye towards selling that practice in three years, that also, had a, has as a factor in there. So that was a really unique conversation. And then we had, as our guest, it was, you have Sue’s general manager US at a terra when we started discussing a terra autopilot, which also was there.
Fully automated kind of AI help desk powered tool. And it just started more and more of these conversations that we’re now tracking these different AI services and solutions for MSPs in the channel. So I think it was two really good kind of discussions that we had and just evolving that conversation about ai.
It seems like every episode we have some take on ai. But that was one that was really focused on a tool. And we’ve covered others along the way that MSPs are testing and thinking about introducing into their stack.
Rich: Yeah. You know that whole all in [00:17:00] one versus bespoke stack conversation, such a nuanced, interesting conversation.
It’s on the one hand we’re well aware, there’s all sorts of data from GTIA and elsewhere that MSPs are consolidating vendors. That, so they’re looking to get more of the stack from fewer vendors, and that’s because fewer relationships to juggle and the integrations are tighter and all that kind of stuff.
At the same time though, there is that concern about do I really wanna have that many eggs in, in one basket? And then, a another interesting fact about that conversation is if you look at some of the biggest MSPs out there roll-ups, like new charter that we were talking about before, they tend not to get everything from one vendor.
They, differentiate sometimes by building a bespokes stack. And there are different. The correct answer for you as an MSP might be different at different stages of your evolution. It’s just a lot to talk about there. And yeah, that was a good conversation [00:18:00] to that we had and got into on that show.
Erick: Yeah, and you nailed the key word there is differentiation, right? Because that’s also if I’ve got the exact same stack as, my competitors. How hard do I have to work now in addition to create some differentiation. So yeah, great conversation. So that’s episode 77, titled 75 Days of Uptime.
Okay.
Rich: Folks, that leaves us with time for just one last thing. Although we are going to spend a little bit more time than we would need for just one last thing. ’cause Erick and I so enjoy that part of the show that we wanna just revive a few favorites in that area as well. Do you wanna go first this time?
Erick: Sure. We’re gonna talk about a few of our favorite one last things or ones that you know. We could pick quickly from a hundred shows. So the first one I’m gonna, I’m gonna go with Rich is we talked about this new Lego GPT AI app that you [00:19:00] could basically just type in what you want to build.
And the Lego GPT app would build it for you and tell you what blocks you needed in order to construct it. So I thought that’s a super killer app. If I had younger kids, I’m sure that I would, be engaged with that with them. Lego is just such a phenomenon. There’s nothing you can build that there’s nothing you can’t build.
With Legos. I, there’s a Lego museums, there’s, Legoland down here in San Diego. So I thought that was a really cool, one last thing we talked about. Lego GPT. So I liked that as one of the ones that stuck out in my mind
Rich: re reason enough for the hundreds of billions of dollars worth of CapEx being poured into AI data centers is that you can combine AI with Lego and come up with something that much fun.
Yeah, that was, yeah,
Erick: AI for fun,
Rich: right?
Erick: Yeah. Yeah speaking. How about you
Rich: Rich?
Erick: Yeah, go ahead.
Rich: [00:20:00] Way back in episode 20 we and we were fairly early to the existence of this company and its product it’s a company called SUNO. And it’s basically an AI service that writes music for you.
You give it a prompt and it writes songs for you. And we had it on the show. To write us a song about MS Pcha. And I, and I gave it the simplest possible prompt you can imagine, and it came up with two different songs that were both really interesting. I, part of what made me think about this show, Erick, is just recently, the last week or the week before Suno, closed a series C funding round that values the company at $2.45 billion. Right now, I personally still haven’t quite figured out what that. Services for other than fun of the kind that we had. I’m not sure why it’s valued at $2.45 billion. I should dig into that a little bit, but we sure had fun with it.
And the thing that I remember we were both impressed by is I gave it this [00:21:00] simple little prompt in which I said, write us a song about a podcast called NSP Chat. It didn’t get confused by what MSP mean. It didn’t think, oh, that he must be talking about the airport in Minneapolis or something like that.
It actually gave us a managed services podcast song, which was impressive.
Erick: It was. It was shocking and scary too at the same time. And that was episode, what was that? 2020 episode? 20. So if you guys wanna listen, pick, get a listen. Episode 20. And we’re gonna link, all the episodes that we’re talking about.
In the show notes here, the one that I mentioned about Lego GPT, that was episode 76, titled Human to Human. And just another aside, rich, I think I read somewhere on the internet, so it must be true, and maybe I’m remembering it incredibly, but I think there’s this a country song written by AI that’s now like topping the charts or something crazy.
So I don’t know how to feel about that myself. I’m like that, that shouldn’t be competing for, human [00:22:00] generated, art in my opinion. So I hope it’s not, they’re not trying to jockey for, having Grammy nominations. I know that there’s also that, that that AI actor or actress that now has got an agent and are trying to shop for, we’re just going too far with some of this stuff, rich.
Here’s my next fun one. It’s episode 66 and it’s titled, it Takes a Community to Secure an End User. And the one last thing we talked about there was the, I forget, millions of dollars paid at auction for a Cheeto that was shaped like the Pokemon character Charizard, right? I thought that was just one of these.
Weird moments in history where a, made up Pokemon character, the shape that came out of a Cheeto, somebody paid an enormous amount of money for at auction. What is the world coming to?
Rich: And what I remember about that one, Erick, is I, I could easily appreciate the absurdity of that kind of money being [00:23:00] paid for a Cheeto shaped as a Pokemon character.
But you were the one you’re like which Charact? And you knew the name. Yeah, I was just totally lost and Oh wow. Okay.
Erick: Yeah, I have young kids, so yeah, we went through some of those the Pokemon trading card days and all that, so I knew exactly watch the Pokemon cartoon with.
One of my sons and it was Charizard. Char. Char. That’s what the Charizard says. Back to you Rich.
Rich: I’m gonna bring us home on on one last thing here. So for the folks who have been enjoying this show, for most Audible, let’s say it’s 100 episodes, this will make sense to you because it was for a while, especially in the first few dozen episodes, a running theme on the show.
Erick and I would just express an enormous skepticism about emotional support animals on airplanes and at airports and elsewhere. And so there, there are probably multiple instances of this I could have cited for this this little celebration [00:24:00] here. But I chose to pick the one I don’t have the episode, actually, it’s episode five all the way back to episode five.
So this is the first time. Is it the ostrich rib? I was looking for the the ostrich. What I came up with is the first time I think we talked about this, was Wally, the emotional support. Alligator. That’s right. The alligator. Somebody tried to get Wally into the the ballpark where the start off the Phillies play and failed to pull that off.
And yeah, we came back to ridges and all sorts of other animals in later episodes.
Erick: Yeah, I was, I knew you were gonna pick one of those, so I didn’t choose. But yeah, we’ve had quite a number of emotional support animals and, people just keep trying to get these animals in and we were, we’ll keep reporting on those for you, everybody.
Awesome. Awesome.
Rich: Folks, speaking of awesome, it is awesome that we’ve made it to a hundred episodes that you have supported us in doing that. We so much appreciate that. [00:25:00] And happy Thanksgiving to everybody out there. Erick and I are gonna be back with another f. Full length, regular episode of the show, episode 1 0 2 in a week’s time.
Until then, I will simply remind you, this is both a video and an audio podcast, which means if you’re listening to us right now, but you’d like to check us out on video, you can go to YouTube, looks up there if you’re watching us on YouTube, but you like audio podcast too, you can go to Spotify, apple, Google, wherever it is.
You’d get. Your audio podcast, you’re probably gonna find us there too. Just search for MSP Chat and wherever it is you do locate us, please subscribe, rate review. It’s gonna help other people discover and enjoy the show just like you do. This show is produced by the Great Rust Johns. It is edited by the great Riley Simpson.
They’re both part of the team with us here at Channel Mastered. They’re ready, willing, and able to help you with a podcast. But really, podcasts aren’t what we’re about at Channel Mastered. Channel Mastered is about helping vendors. Build, grow and optimize MSP channels, and you can learn more about the many ways we do that at [00:26:00] www.channel Mastered.com.
Channel Mastered has a sister organization called MSP Mastered, that’s Erick working one-on-one with MSPs to help them grow and optimize their business and learn about. that at www.mspMastered.com. Once again, we thank you so much for all the support and joining us here on the show. We’ll see you in a week, happy Thanksgiving.
Until then, we will simply remind you that we always do yet can’t spell channel without [00:27:00] MSP.
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