Navigating PE Acquisition w/ Jake Levine

Welcome to the $10 Million MSP Podcast. This podcast is where I dive into the real stories of MSP leaders who have gone beyond $10 million in revenue, how they built their teams, created scalable systems, and turned their businesses into valuable wealth-building assets. I'm Brian Hoppe, strategic coach to MSPs. I work with MSPs generally in the $5 to $50 million range. In each episode, I sit down with leaders who have built MSPs beyond $10 million in revenue to unpack the inflection points that truly matter. From the personal stories behind their journeys to the fundamentals like culture, operational maturity, and driving profitability. This isn't another MSP podcast about tools and tech. On the $10 Million MSP Podcast, you'll get behind-the-scenes conversations with leaders who've built thriving MSPs, their biggest wins, their toughest lessons, and the practical takeaways that you can take back and use right now. If you're an MSP owner who knows that growth starts from within, that mindset, leadership, and strategy align to create both wealth and meaning, then this show is for you. New episodes are released every other week. So, let's jump in. All right. Well, today I'm here with Jake Levine, who is the CEO of Robo. And Jake, welcome to the show.

Glad to be here, Brian. Good to see you.

Awesome, man. Well, yeah, just to kind of start, I know that you kind of came into the MSP world from a different path. Um, but actually, kind of what I want to get started with is, um, if you could say, um, what, what do you think like most founder-led MSP owners, um, misunderstand about what it actually takes to run a private equity-backed MSP?

Hmm. Coming in hot. I like it.

Yeah, right. I like to, we like to punch hard to start. Yeah.

Um, Okay, so first, my disclaimer is tremendous respect for all founders, right? I, I have never built, as you alluded to, Brian, I've, I've not built something from 0 to 1, right? And, and that's a skill set in its own right, and I have tremendous respect for it. Um, my foray into the MSP world, like you said, was was jumping in here, uh, acquiring an MSP that was already at, you know, uh, close to $10 million in revenue. So it was a— in some respects, it was already a fully baked thing. Um, but the challenge, uh, to your question, right, the difference with running a private equity-backed MSP, or any company for that matter, is I would say the discipline, the ability to actually create a plan and execute against that plan. And, and I, that's a, maybe it feels a little cliché even saying that, but all the founders I talked to in the, in the MSP world, and again, it's not just MSPs, it's any small business, you know, as a founder, as a sole shareholder, You have the luxury of, you know, doing what you want to do, right? For better and worse. And if you want to take your foot off the gas a little bit because, hey, it's coming into the holiday season, you know, you're allowed to do that, right? And, and you're only accountable to yourself and your team and your customers, right? But, but you can choose how hard to push when and You know, and why? With any outside investors, I would say, but certainly with private equity, you know, there's a very clear expectation. There's a timeline. Now, I think not all private equity is created equal, right? They're not all the big bad, you know, whatever vision people have.

Yeah.

But, but they want a specific outcome, right? They want to grow a business. They have a timeframe and your job as the CEO is to execute on that. So here's where we're going to go. Here's how we're going to get there. Here's the progress I'm making, or here are the obstacles I'm running into and, you know, hold me accountable if we're not getting there.

Yeah. Yeah. Yeah. So that totally makes sense. So, so what I'm hearing is it's, it's kind of like if I'm a founder, I can say, hey, you know what, this year we're going to kind of take it a little bit easy. we're only going to do like 7% to the bottom line because I want to do some stuff differently or whatever. That's not really an option in your world, right? Like you've got to create the plan before the year starts and then you have to execute to that plan. Otherwise they might be looking for a new CEO, right?

Yeah. Yeah. And, and it's, you know, not even in a, like a scary bad way. It's just, hey, yeah, you know, this is, This is what we're looking to do. It's like, it's playing sports, right? Like, hey, you know, you got to hit .300. If you're hitting a buck 50, like, somebody else is going to hit .300 and they're going to replace you, right? So, um, yeah, I think there's even maybe another example that I come up to a lot with founders is, um, where and how they decide to make investments in their business.

Yeah. Right.

As a founder, I mean, every expense you have potentially reduces your bottom line, right? So there's a difference there, but you have the freedom to say, you know what, yeah, this year let's just try this new thing. Let's just, you know, invest $100K into a sales guy and let's just see how it works. Right now with an investment group, you have to be a little bit more thorough than that. I would say, you know, you can't just say, I'm gonna try this and we're gonna see what happens, right? You gotta say, I'm gonna invest $100 grand because I believe these specific outcomes are gonna come from it. You know, we're gonna generate $200 grand in, in gross profit as a result, and if we're right, this will be a good investment and it'll be worth it, right?

Yeah.

And, and there's just an element of showing your you know, your investors, your board, whoever it is, that you've kind of thought that through in a way that I think most founders don't have to. I'm not saying some of them don't, that, you know, by their nature, maybe they want to as well, but they don't have to in the same way.

Yeah, yeah, 100%. And you've probably heard it said, like, the difference between, you know, a best-in-class MSP and, you know, average or bottom quartile is the ability to create the plan and execute to that plan. And, you know, combined with the skill of the leadership team or the management team. And so, you know, it does follow that, like, actually, yes, a lot and probably up to 3 quarters of MSPs don't actually manage the business that way. And so it's probably a good discipline to have in place where you're sitting. But also it probably comes with a good bit of pressure associated with that as well, right? I'd imagine.

Completely agree. Yeah. I mean, I think just if you, if you sort of step back, right? I mean, I'm responsible both for my team and keeping them employed, which I take very seriously. I'm responsible for our customers, keeping them happy and safe and secure, which I take very seriously. And I'm also responsible for a group of people's money, which I also, you know, take seriously and get stressed out about. So yeah, that's the element again that the founder doesn't have, right? It's sort of their money at stake rather than a whole bunch of other people.

A whole bunch of other people. Absolutely. Awesome, man. Well, well, thanks for, thanks for diving in quick. Um, just to kind of like zoom out a little bit, um, maybe just give us kind of the quick version of your story as far as like, hey, how did you, how'd you come into the MSP world, uh, become CEO of Robo? What was kind of the, um, you know, the, the, the events that led up to kind of where you're at today?

Yeah. Yeah. So. I guess short of taking you all the way back to the, I don't know, you know, the origin story at birth, I—

Right.

I will say I was— most of my career professionally has been curiosity-led and very much a— I've always been a jack of all trades, master of none, right? I came out of college, I worked in political campaigns, I worked at a startup in the educational world, I worked in real estate investing, I had a brief stint in the beverage alcohol industry. And so I've always kind of jumped at opportunities to, to learn and, and take on what I felt like was a big challenge, you know, some sort of outsized responsibility. And back, I don't know, maybe it was 2015, 2016, I was thinking about going back to grad school. I was a political science undergrad and, you know, short of enjoying reading the news, I didn't feel like that created a lot of value for me. So I was thinking about going back to business school. And I heard about this idea of a search fund, which maybe listeners will be aware of. We're the guys that spam your inbox, you know, saying we want to buy your company and we're going to preserve your legacy, right? There's a massive number, it feels to me, of searchers out there now relative to what there used to be. But I, I became enamored with that idea because I thought, gosh, what a way to challenge myself, what a way to grow and develop and, and put all these ideas in my head or put them in practice that I had in my head about how to run a business and build a team. So I went back to grad school, uh, at the University of Chicago, and while I was there, I got to know an investment group called called NextGen Growth Partners.

Okay.

And they are a private equity firm that also focuses in this kind of search fund world. So I got to know them and their team really well over the course of a couple of years and ultimately joined them. And the idea from the jump was, hey, you know, you'll help us go find a company that we get excited about collectively that we think we can acquire and grow and eventually sell. So that was in 2019, 2020, right when COVID was hitting. Um, I was flying all over the country, you know, trying to learn about a million different companies. I mean, I, I remember looking at a, uh, a label printing business in California that was really cool. I looked at a, a cell tower maintenance business in Little Rock, Arkansas that was Really well-run business, but as soon as I stared at one of those cell towers and saw how high it was, I thought, I can never run this business. I'm gonna be terrified of it.

Yeah.

I looked at a pet food manufacturer, which was growing like gangbusters during COVID but, you know, too frankly growing too fast for my ability. So along the way, I found Rovo in Austin.

Okay.

And I had been familiar with the MSP world, certainly, as a lot of investors are. And I knew there were a lot of things to like about it. I frankly had expected that I wouldn't find the right opportunity in the MSP world because there were so many other investors milling around. And, but I found an opportunity in Austin with Robo where I think it was pretty, you know, pretty common founder story. It was a founder who had built a really good business, really good team, really good customer base. Wasn't necessarily what you mentioned, Brian, a really highly, you know, OML, high maturity operation.

Right.

And, and the founder, I think, was tired, right? He was tired coming out of COVID He dealt with that wave as so many MSPs had. And he was feeling like, man, I'm, I'm just, I'm bombarded everywhere. I don't have the time. And he hadn't really been able to organize the business or delegate and elevate, right? So he was stuck in the weeds everywhere. Yeah. And when I pitched him on, look, I can join, I can take a bunch of this off your plate. You can continue to be, you know, a high-level resource to customers. You can continue to be a partner to customers, but, but let me take all the operations and, you know, business building off your plate. He was, he was excited by that. So we ended up acquiring the business in early 2022, and we've been running ever since.

Okay. All right. So, so coming up on 4 years, um, it sounds like, uh, for you. Awesome. And, uh, you know, I guess, I guess we could, you know, we could either, we could be excited for you or we could be like, man, we could lament that you found yourself in the MSP industry. Right. Because there's, there's gotta be a lot more businesses that are like easier to run, um, out there that you probably could have picked. Right.

Yes. Yes. I, I could not agree more.

Yeah.

I, I, I, so I get together every now and again with some of my buddies who, who have the same investment firm backing them, and they ended up buying other companies in other industries. And, and I give them crap all the time because there's, again, so much that's amazing and attractive about this industry, don't get me wrong. But I, I think you and I would both agree, Brian, that the The operations of an MSP, I mean, are a never-ending, constantly evolving, constantly complex battle, right? I mean, you're just, you're trying to fix these problems as they come up. And then the more you grow, the more different things break, you know, the, I mean, the SLI, like, assembly line or factory, you know, metaphor, I think is very apt. I mean, it's a— It's a factory that you're trying to build all the time and something breaks every single day. So I got a buddy in a business, uh, without going down a whole rabbit hole, his company was essentially renting, uh, renting steel plates that you would drill into vacant properties in their doorways and in their windows. And, and it keeps, you know, people from breaking into vacant properties, right? So operationally, think about that. Pick up steel, put guys on truck, drive out to site, install steel, drive back to office, right? Like, that's, that's the operation.

Get paid, you're done.

And they, and they, and they rent it out, right? It's just an annual rental. And, and so, you know, I look at—

No 24/7 monitoring.

No, none of that. Threat assessments look very different in his business. And, and look, like, I know that every business is hard, every industry is hard, but, but yeah, I think MSPs are uniquely challenging in their evolution.

Yeah, and I've never met a bored MSP owner. Like, there's always plenty of things to do. And, you know, it is kind of a never-ending process of improvement and And fixing the things that come up and all of that kind of thing. Real quick, can you give us kind of a sense of scale as far as what you mentioned, buying it at $10 million? Where's Robo at today or around $10 million? So where are you guys at today?

Yeah. So we're now, we'll end this year around probably $23 million in revenue. Okay. Next year, the goal is to get to $30. We have a team right now of about 75. I think we actually— we— 76. I think we recently hired 76 across a few different offices now. So we have Austin, we have North Texas, we have Portland, Oregon, and we have Tampa, Florida.

Okay, gotcha, gotcha. Okay, and then are you guys— it sounds like you're on a— well, you have offices in some other places, probably some acquisitions in there. Is that kind of, um, the, the main plan for growth for you guys? What's kind of the, the growth path that you guys are going down?

Yeah, it's a, uh, for apologies for the cop-out, but it's a, it's an all of the above, you know. We certainly are, are building and trying to get better at our sales and marketing strategy, right? I mean, I think like so many in our industry are, we're all trying to figure out how you, how you sell this service better, especially without knowing exactly when the right time is for that customer to buy. I think that's one of the hard parts, but we've been building there and had really good success this year with new logos. But, but yes, you, you Uh, assume correctly, Brian, we're also, we're also looking to acquire. So we've acquired, I mean, since we first bought Robo, we've acquired 3 other MSPs. And I expect that we'll acquire over the next 2 years, you know, probably 5 to 6 more. Um, that would be the goal, uh, where it makes sense, of course. You know, I think it's really easy to, to get caught up in You know, the deal for deal's sake. And I think that that can get dangerous, right? That can be challenging for the business, for your customers, etc. But I do think, as a lot of people in our industry are doing, there's an opportunity to get to a certain size and scale faster by acquiring. Sure.

Yeah, 100%. And I mean, there's the multiple arbitrage and all of that kind of stuff that goes along with it as well. And its challenges, right, with the acquisition, the integration, the potentially having a whole new office to manage and all of those kind of things, which we might get into that a little bit more here in a little bit. But I kind of want to shift just for a minute as far as like your experience. So, you know, coming into the CEO role, thinking about that experience for you, What do you feel like the biggest gap was between what you thought being CEO would be and the reality when you showed up?

Interesting. You know, I guess what comes to mind, there are a million learnings. I'm humble enough to acknowledge that I had no idea what I was getting myself into in general.

Yeah.

I think the, maybe the learning that stands out is figuring out, I guess, well, 2 things. Okay. One is communication, right? I mean, the classic leadership kind of axiom, right? Like, you know, you have to be in the business of just repeating yourself all day long. You have to be telling your team, you know, what, 7 times before they're actually listening. You have to, you know, preach the gospel until you're so tired of it, you know, and only then maybe the message gets through, right?

Yeah.

And I think that was a, that was a learning for sure. I, I thought, oh, well, I'll say a thing, people will think it makes sense, they'll just go do it. No, of course they don't, right? I mean, yeah, they don't get it yet. Yeah. So, so that was a big one. Uh, and then the second one, I think, and I'm not sure how to describe this, but kind of learning about how to manage the tempo of people, you know, the how hard we push in any given moment. Especially when it comes to implementing change, because a lot of what I've gone through in my experience has been changing the way we used to do things, right? When I first bought Robo in Austin, there was a lot that we changed in the business. We changed our revenue model, we changed our PSA system, we changed our org structure, you know, really. And so I think going along with communication, it's tempting in your head to just say, well, cool, we're gonna just knock all these down like dominoes. But, but you, you can't do that. I mean, people have a, I don't know, you know, some, uh, like equilibrium here when it comes to how much change they can tolerate before they just stop listening and don't do anything, right? So I think figuring that out, and that to me feels— it's a feel thing, you know, there's no way of planning that, just trying to read where people are at and see, can we go faster right now? Can we push through that change? Or do I have to prioritize a little bit differently?

Yeah, yeah, that's really interesting both because I find that to be the case, especially Well, the first thing you were talking about as far as like overcommunicating, um, and I, and I found that with my leadership and my MSP, which was like, hey, I'm, I'm actually need to say these things literally every time we get together. Like for me it was, okay, here's why we exist. Um, here's, here's where we're going. Like here's our future vision and here's what our, our values and our culture are. And, um, and, and I literally talked about it every single time, uh, that we got together as a team. And it— I found that once, by the time that I was like, oh my gosh, I can't believe I'm saying this again, then it's like, yes, we're starting to get it. Like, everybody's starting to get it.

Mm-hmm.

And, and then it's finding different ways to say it and different illustrations. And, and how do you make it like connect with people and, and all of those kind of things. And so I definitely relate to that one. And I think that probably most leaders don't yet realize like, oh, I need to, I need to say it and then I need to keep saying it for as long as it takes. Yeah. So I thought that was a great observation.

And the follow-up, right, is just so, so important. And maybe that's where we Intertwined with like my, my comment about pushing change and the tempo of that, you know, like you have to— at least what I've found is I have to have the energy and the focus to keep following up on whatever message or whatever thing we're trying to get done. Because if I don't, and if I then immediately jump to the next area, the next area, you know, we'll, we'll lose traction on that initiative, right? So I have to be willing to do the full repeat communication, repeat the why, repeat the why, you know, until, until we really get to that finish line, whatever it is. Um, so that's tough for me.

Yeah.

Because I want to just like knock them out and keep going, but it's just, I don't know, I haven't been able to do that yet.

Yeah, yeah. And, and there, you're, you're right, there is only so much pace that you can go at, um, until, you know, people— yeah, I mean, eventually people will check out when it's just too much, right? And, and so, and not maybe not completely check out, but it's like, then it's like you sometimes you have to slow down in order to speed up, right?

Yeah.

Um, so, so, and on that note, like when you— because you're, you're, you come in, you, you're You're like, hey, we've got all these changes to make. I want to do all these things. How did you go about kind of building credibility with the already established team that's in place?

Yeah, I mean, I don't know is the short answer. I think my more thoughtful answer, I guess, is I knew there were certain things that I would not bring to the table and that would not create credibility for me, right? I knew I was not technical and this is a technical business.

Mm-hmm.

So, I couldn't relate in that way. I knew objectively I'd never been CEO before. Right? I couldn't say, hey, I've got a track record of doing this 5 times and this is why you should listen to me. So I think what I leaned into was in fact the opposite, saying, hey, I am new to this. I don't know anything about how a server is architected, but I want to learn.

Right.

And I want to— and I'm going to show up every single day. And I'm gonna keep asking questions, and I'm gonna keep, you know, trying to figure out ways to make your life easier or make this business better, and I'm just gonna stay at it. And I'd like to think that the persistence has built credibility.

Mm-hmm.

And the— I think there's an element of that classic, you know, you build credibility by just doing what you say you're gonna do, right? It's— it doesn't have to be some complex thing. It's just, yeah, Brian, I told you I'd follow up and do this thing. Great, I followed up and I did that thing.

Right.

It's, it's not, um, and, and if you do that enough, people at least feel you are, you are dependable as a partner and as a, as a leader. So, um, Yeah, I mean, I think that was the foundation. I would say there were probably also some important moments where I tried to get other people to validate the vision that I was trying to chart for us.

Mm-hmm.

And so that validation was probably really important too, because it was one thing for this newbie, non-technical guy to say, We need to get better at this thing. We need to go in this direction as an MSP. And it was, it was another when I, I started to bring managers and team members to, you know, IT Nation and other conferences. I started to bring in outside perspectives and they would say similar things. And then the managers would kind of look at me and be like, oh yeah, I guess what you're saying Isn't BS, you know, it's real. Yeah, like, yeah, you know, trying.

Yeah, so yeah, 100%. I mean, yeah, you know, just, and just the, I think too, this is the fact of like showing up, you're like, you're, you're, you're showing up every day, you're, you're in the trenches with them, you're, you're having integrity in, um, in, in, uh, you know, doing what you say you're gonna do. And that, and that builds a lot of trust as as well.

Yeah.

Which I love that. So, I'm curious on like, because, you know, being a private equity operator, I'm sure there are some tensions that kind of show up between you and the board. And so, I'm curious, like, where do you kind of see those tensions show up between you as operator and private equity, and how do you kind of navigate through those things?

The first few things that come to mind, I guess, are probably related to what I mentioned earlier. Where to invest, when to invest, how you justify that.

Mm-hmm.

I'm, you know, at the end of the day, I'm, I'm no different than a founder. And I feel there's a lot going on on any given day. There's, I think a lot about my style is more intuitive in general. And I, I pride myself on, you know, doing the math, but, but if I'm honest, it probably starts mostly with intuition. Oh, I think we should invest in our customer success team because it feels to me like that's a missing piece for our customers and it's going to improve retention and it's going to improve our ability to cross-sell, upsell. And, and I can tell myself that story really quickly.

Yeah.

And there are times when, yeah, I just want the flexibility to say, You know, let me just go do it. Let me just go do it and try it out. And, and I don't want to have to justify it in a big Excel spreadsheet and PowerPoint slides to my board either, right? I mean, it's not— I don't love doing that. Um, so there's, you know, there's a, there's a kind of a time cost there, I guess. Sometimes, um, you feel like you have to, you have to put in that, that time to justify decisions. when you'd rather just go and do them.

Yeah.

I think there are other elements. Again, just generally, hey, we— like my tempo comment, you know, any outside party, I'm really not gonna even single out private equity because I think if you had your cousin Sal who's an investor in your business, right, he's not in the business every day. If he wants to make money from the business, it's really easy, you know, to, to sit in the cheap seats, right? And say, well, why aren't you growing faster? Right? I mean, that's just— it's easy to do that.

Yep.

And so there are always times when an outside party says, well, why aren't— why aren't you going faster? Why, why can't— why can't you implement that change faster? Why can't you, you know, sell those new logos faster? Why can't you improve that gross margin faster. And I think most of the time that doesn't even come from a bad place. It's just, it's the reality of kind of distance from the ground, if that makes sense, you know. And so there are times when I'll sit in a board meeting and I know it's coming, right? They're gonna say, well, you've, you know, you told us you thought you could get this done by the end of Q4. And I've got to be the guy that says, yeah, we're We're still pushing, you know, we're not quite done yet. And so those are, those are not fun conversations, but I think it's the reality of a business with real human beings in it.

Yeah, yeah, I mean, absolutely. And that's, yeah, it makes a lot of sense because there has to be, you know, and I would say at least some sense of healthy tension all the time, right? Because it's like, hey, you, you know, if they're pushing for, hey, this level of growth or whatever, and you're saying, well, yes, I would also love to do that, but here are some realities that we have to deal with, right? That it's not necessarily just straight up like, oh, we can just do that super easily, right? And so, yeah, I can imagine that there's a lot there that's like, okay.

Yeah.

Um, we, we have to negotiate those things and, and, uh, and, and kind of come to an understanding in, in certain, certain spaces like that, which, um, and, you know, and I would imagine, um, you know, it's, it's kind of that— it's, it was just that push-pull, right? It's, it's a little—

it's—

Yeah. And, and, well, talk, talk about like, I mean, how do you, how do you think that affects you versus like, uh, just a founder without a board Where it's like, hey, you've got somebody saying, let's move faster, let's grow quicker, let's do, let's achieve our plan quicker. You know, what, what, how do you see that? Do you see that as a benefit for you versus somebody else? Or do you think it's kind of like, you know, I don't know, it's pretty, it's pretty annoying having that all the time. I don't know.

Yeah. Yeah. I mean, I liked that you You said healthy tension, right? Because I think the other way to say that is accountability. And accountability is, in general, for me, I think accountability is a good thing. You know, I came from growing up playing baseball. I played college baseball. And so, you know, you need a coach to push you, right?

Yeah.

I mean, I always felt I did. Some people maybe have like their own internal motivation all day long, but I benefited from the external nudge. And I think that's true in business, you know, for the most part, right? Having healthy accountability is a good thing. Just challenges you to sharpen your decision-making, to think about, you know, where you want to go and how fast you want to get there. And so I think it's good. Now, I also acknowledge I've never actually lived the opposite, right? And don't get me wrong, there are days when I feel like, oh, it'd be so nice to not have outside investors and not have this accountability.

Right.

But I think on net, are we, are we pushed to be a better business because there's some sense of accountability. Yes, I do. I do think that's by and large true. And, and it doesn't mean that, you know, founders who don't have that are not running good businesses. Not saying that at all. But, um, but I think accountability helps.

Yeah, yeah, 100%. And, and I, I, you know, with all, all of the MSP owners that I talk to and work with, um, you know, it's the folks who don't have that, a board at this point, they're going to things like peer groups or working with somebody like me as a board-level type of advisor in order to like install that sense of accountability for them. Because you find folks that just, they're, you know, maybe they're coasting a little bit and maybe they're like, actually, I want this, but I feel pretty comfortable right now. So do I actually want to push myself I'm not really sure, but then, but ultimately it's, you know, it's a really good thing to have accountability in place to ultimately get what you want, right? If you, well, if you want something and don't have it yet, then, well, there's a reason for that. And so other people can help you get there. So that makes a lot of sense. So, so just like, just thinking about, you know, I'm thinking about leadership right now in general, as far as like, how, you know, how has, how has your leadership grown, do you think? Or, or what kind of new levels of leadership have you stepped into since you've been running Robo?

Hmm. Well, I feel like to get the best answer to that question, you should actually ask my team and see if they have noticed a difference in my leadership style and quality and abilities.

Are they available now?

Can we bring them in? Yeah, dial them in right now. I mean, I think, again, when I came into this, There's no doubt I was naive in many respects.

Mm-hmm.

I don't think I came in, you know, arrogant or full of myself. I mean, I knew there was a lot to learn and a lot that I had to prove.

Mm-hmm.

But I certainly— I would say I did not have the patience. And I did not have the empathy that I would like to think I have now.

Hmm.

I think as I've learned these lessons around communication, around tempo, around change management, around the, you know, the need for that vision and those values that you talked about, Brian, which I totally agree with, I think I've gotten better at Um, at conveying that and, and explaining that.

Mm-hmm.

Um, I think that I have also gotten better. I don't know that this is necessarily leadership in the, you know, philosophical sense, but I think that I've gotten better at bringing in other good people.

Mm-hmm.

And I definitely have experienced, like, a cliché thing, right? But I mean, everything is easier when you have great people. It's easier to be a good leader. It's, uh, it's easier to build a good company, right? I mean, just better people, uh, who are— who share your vision, who are self-motivated, who are excited to go do and achieve, they make everything run more easily, right? So, I don't know, maybe I'm trying to say a good leader finds good people, maybe. But I think that's been really important as well.

Yeah. Well, and a lot of CEOs that I talk to that are, you know, your size and bigger, Especially, it's, I mean, the job actually becomes more about finding the right people than, you know, than even like running the company per se, right? It's finding the right people, it's building the right leadership team, and, you know, and then, you know, letting brilliant people be brilliant and do their thing. And then you're focused on the people. You're focused on the culture, um, and, and much less so on, you know, running, running the, uh, you know, the operations of a, of a company, right? Or of an MSP because, because you have brilliant people that are, that are doing that for you. So, um, you know, and, and all of those things kind of like, you know, they can, they can feel a little, you know, squishy, right? Uh, Mm-hmm. I'm, you know, thinking about, you know, when you say leadership or, or you say mindset or culture or, or that kind of a thing. It's like it goes over people's heads a lot of the time because, because it's kind of, well, they're, they're, um, you know, soft or kind of squishy concepts. But, uh, but the more folks that I talk to in, um, you know, in the higher levels of leadership, it's like that's what they talk about. Because it turns out that when you learn that and when you live it, those become some of the most important things, um, that, uh, you know, that you're talking about there. So. So yeah, I really, really like that.

I think about an investor, Brian, that I have who told me something early on, and I've been trying to live this. And he basically made the argument, he said, look, you should not be better at doing any task in your business than the manager of that task or function, right? So, yeah, if you are, um, and I think it's a natural transition for a lot of founders especially, right? You founders, most mostly of MSPs, start these things because they were great technicians, right?

Yeah.

They were, they were the best technician and probably combination of customer service related, you know, sales related, right? So They could do that better than anybody else. And then they're, they're growing. They're, you know, now they're adding an actual service department, not just a handful of techs. They're adding a back office, accounting, you know, AP, AR. They're maybe adding sales. And there's periods where, you know, they're, they're the best seller in the business, right? They're the—

Yeah.

They're still the best escalation resource in the business. But my investor, you know, always talks about like, you cannot be the best at any of those functions. If, if you are, then you're not doing a good enough job at bringing in new people, right? So I have to have a CFO who's a far better finance and accounting guy than me.

Yeah.

I have to have a sales leader who's a far better salesperson than me. I've got to have an ops guy who's far better at ops than I am. And yeah, you know, I think that's a, that probably moves in like step functions as you grow. Yeah. But I try to keep that in mind a lot. I think that that's key to this whole thing.

Yeah. I mean, I think you're spot on there and I see that all the time. And especially between, I would say like the $5 to $10 million, especially where it's like you know, it's this big identity shift with owners because I'm, as an owner, I'm used to being the guy with all the answers.

Yeah.

And I'm used to being the one who, who, you know, it's every, the kind of the whole business revolves around me. Um, but you really, you can't unlock those levels of growth if you're still operating in that space. And so I think what you said there is absolutely brilliant. It's like, I, you know, your job becomes replacing yourself in all of those functions and finding people that are smarter than you. Because if you're the smartest person in the room, well, you need to, you need to make a better room or find a new room, right? Um, and, and so, uh, so that, that really, really resonates based on a lot of conversations that I've, that I've had and, oh, and a lot of the work that I do, um, with my clients as well. So, um, man, that, that's really, really good stuff. So. Okay, so I'm gonna ask you another question. I might already know the answer to this, but we're kind of, you know, kind of as we start to wrap up, what would you say is the biggest mistake and/or the worst decision that you have made as a CEO?

You do know the answer to this already, Brian, because we have talked about it before. But I will, Give you 2. I'll give you one very tactical one, and I will give you one more, you know, ethereal one, I guess. The, the ethereal one is— and it's like, it's such a cliché, right? You, you, you should fire faster.

Mm-hmm.

You know, holding on to people that I knew were not the right fit And for any number of reasons, I wanted them to be the right fit. You know, maybe as people, I really liked them a lot. I really enjoyed them, but they were not, you know, they were not better than me in that role, right? Or they weren't as good as just the business needed them to be, and they were not the right fit. And I think that most owners, most CEOs, founders, Like, you feel that, and it's really easy to try to give grace for a while and hope that things change. And my experience has been often they don't change, and so you just end up kind of wasting time. Then my tactical mistake, uh, do not change your PSA system. Unless you are Uh, a very small MSP, right? If you're— I think if you're small, if you're, you know, less than 10 people maybe, you know, then sure, the consequences are not significant.

Mm-hmm.

But as you get bigger, gosh, I mean, there's, there's no point. I did that recently, as you know, Brian.

Mm-hmm.

And I switched, I'll say, from one, you know, well-known legacy provider to another well-known, but, you know, upstart provider here. And, and to be fair, it's not that the product is bad. I think the product is good. It's, it's probably better than the legacy one I was on, but, but the cost of that change is not worth it. You know, none of these tools are, you know, 3x better than any other. ConnectWise, Autotask, Halo, you know, you name it, like none of them are 3x better than each other. They're all fine. And any engineer who sees a demo and says, oh my God, our life is going to be so much better. I don't think is appreciating the cost of change. So, um, I would not go through that change again because that, you know, back to my comments about tempo and prioritization and, and just frankly, you know, the private equity elements of having a plan and executing that plan. Wasting time on a, on a PSA migration, uh, is in no one's Yeah.

Okay. Well, yeah. So it sounds like, you know, it's not so much the, you know, that it's not a better product or anything like that. I mean, it totally could be, but the opportunity cost of changing— I mean, the actual financial cost plus the opportunity cost plus all of the time cost is just like, it's too much.

Yeah.

Is what it sounds like. Yeah. And, and so that's why, I mean, my advice is always like, if you don't absolutely have to change, then don't change and figure out how to make what you have work better for you.

Yes.

And so that sounds like you'd be along the same lines. Okay. Yeah. And, you know, and we've definitely had this, this kind of, this conversation before in different contexts, but, you know, But I think it's helpful, you know, it's helpful for others to hear because I hear all the time and people ask me, you know, hey, I'm thinking about making this change. And, you know, if you want to, okay, but it's, you know, it's probably gonna hurt more than it helps, especially in the short term. So awesome, man. Well, okay, so I'm gonna— so I've got a few rapid fire here. This is just like first thing that comes to mind. Quick answers. So, um, so first one is, what's a belief that you have changed your mind about in the last few years?

That Windows sucks. It does not suck. I used to be a Mac guy. Okay. Okay.

Yeah. Okay. Well, there you go. Um, I'm still, I'm still a Mac guy. Just because it's simple for me, but it's okay. What is something that you've been curious about lately?

Interesting. Business related, I have been curious about how to scale customer success across multiple sites, because that is a very, you know, timely challenge for us right now.

Yeah.

Um, gosh, outside of business, I'm perennially curious about, um, physics. That's a random answer, but like, uh, as a, as a guy who, um, again, I was like political science, I was all about you know, touchy-feely stuff. And I'm not an engineer. I mean, and, and so I, I envy a lot of my team who have that engineering brain, uh, because I don't understand the first, you know, thing of it. And I'm a big Formula 1 fan.

Okay.

And, and a lot of Formula 1 is about, you know, different physics challenges. And, you know, so all that boggles my mind. And I, and I watch, uh, I watch any YouTube video I can that like dumbs it down enough for me to understand something.

I love that. I love that. I can, I can definitely geek out on some physics and astrophysics as well. So, so what's one thing that you can't live without in your daily routine?

Coffee addict for sure, for caffeine.

Love it. Yeah.

Love it.

Okay. And then what is your go-to way to unwind?

The healthiest way for me to unwind would be going for a run, which I have a love-hate relationship with. The unhealthy way for me to unwind, uh, which my wife will make fun of me for, is playing video games, being like a, you know, an adult who plays video games. So one of those two things I will do.

Could be healthy or unhealthy. It probably depends on your posture. Um, there, because there, well, there's a reason you're drawn to it. So, you know, and if we had more time, we could totally unpack that.

Um, right.

Okay, and then last but not least, what is the— what's like a book or an idea or a piece of advice that has shaped you the most?

That's a very big question that I don't know that I feel prepared to answer. I guess 2 things pop into my mind. Um, uh, at risk of being cliché, um, the book The Alchemist, um, I thought was a just a phenomenal book on, you know, mindset in life, right?

Yeah.

And dealing with learning, growth, change, you know, optimism versus pessimism in life. So I, I find myself going back to that every few years, and it kind of resonates differently depending on what I'm going through in that particular moment.

Mm-hmm.

I, I'll say also recently a book that I read that, um, um, that I found a lot of value in, and I'm gonna now butcher the name. I'm trying to look for it on my desk here, but It was called, you know, frictionless service, frictionless service, something like this. I'll find the name, you can post it somewhere.

Yeah, yeah.

But the argument that they made, which I thought was really, really relevant to our business, was what people value most, and they look— the writers, you know, looked at all sorts of companies, not just IT, but anything with a customer service element, and they make the argument that people don't actually care about the touchy-feely personal interaction that they had with your company. What they want first and foremost is resolution to their issue. And so the fastest most direct way for them to get their issue resolved is the best way.

Yeah.

Now, if you add on when, you know, time allows some interpersonal dynamic, great. But their argument was that we often overstate the importance of that at the, at the risk of not delivering a frictionless Service experience. Like, that should be the goal, not the happiest, but like longest service experience. So that one was pretty impactful.

Awesome. Okay. And so is it the frictionless organization?

Yes, I think that's right.

Okay.

Yeah.

Delivering great customer experiences with less effort.

Yes.

By Price and Jaffe. Okay. Awesome, man. Awesome. Well, thanks for that. I hadn't heard of that one before, so it's Now on the list. Um, well, Jake, man, this has been great. I really appreciate you, uh, joining us. So, and, and if people wanted to learn more about you or get in touch with you, uh, where should they go?

Yeah, shoot me an email, jake@robo.net.

Um, there you go.

Take a look at the Robo website, robo.net. Awesome. Um, find me on LinkedIn, you know, however you want.

Great. Well, perfect. Well, Jake, thank you so much, um, again for, for joining us and, uh, love the perspective and love kind of what we, uh, what we jumped into today. Um, so thanks so much, man.

Thanks for having me.

Thanks for listening to the $10 Million MSP Podcast. I'd like to encourage you to take just one insight that you heard today and put it into practice because small shifts create big momentum. If you enjoyed the episode, make sure to rate and subscribe on your favorite platform so you never miss a conversation. Thanks again for tuning in, and I'll see you in the next episode.