Winning Customer Transition Strategies for MSPs with Matt Yesbeck

Are you leaving money on the table when offboarding MSP clients? 

Matt Yesbeck and his son Gage saw a massive gap in the MSP industry—no structured way to transition low-value or misfit clients without losing revenue or damaging reputation. Instead of accepting the status quo, they built MSPX, the first-ever MSP contract exchange platform, helping IT service providers monetize client offboarding, ensure smooth transitions, and protect brand reputation.

In this episode of WIN Podcast, Carrie Richardson digs deep into:
✅ The story behind MSPX and how it’s transforming the MSP industry
✅ How Matt and Gage launched an MSP AFTER creating a tech startup
✅ The real challenge of pruning clients—and how to make it profitable
✅ The father-son dynamic of running two businesses together

If you’re an MSP owner, IT leader, or entrepreneur, this episode is a must-listen. Learn how to WIN in the MSP space by making strategic moves that fuel growth.

💡 Subscribe now and don’t miss out on game-changing conversations that help you scale, sell, and WIN!

In this episode we refer to The Pumpkin Plan for MSPs, a book by Dave Cava, who was a previous guest on WIN - Check out his episode here!

Carrie Richardson and Ian Richardson host the WIN Podcast - What's Important Now?

Serial entrepreneurs, life partners and business partners, they have successfully exited from multiple businesses (IT, call center, real estate, marketing) and they help other business owners create their own versions of success.

Ian is certified in Eagle Center For Leadership Making A Difference, Paterson StratOp, and LifePlan.

Carrie has helped create and execute successful outbound sales strategies for over 1200 technology-focused businesses including MSPs, manufacturers, distributors and SaaS firms.

Learn more at www.foxcrowgroup.com

Book time with Carrie here!

Be a guest on WIN! We host successful entrepreneurs who share advice with other entrepreneurs on how to build, grow or sell a business using examples from their own experience.

Transcript

att Yesbeck helps MSPs WIN when they Pumpkin Plan Their Client Rosters
===

[00:00:00] Carrie Richardson: Good morning, everybody. And welcome to Win. My name is Carrie Richardson. I'm a partner at Fox and Crow, one of the developers of the MSP sales process. And with me today is Matt Yesbeck, who is the founder of the Internet's first MSP contract exchange platform.

[00:00:20] It's called MSPX, and frankly, I've never seen anything like it before, so I'm really excited to Learn a little bit more about it. Matt also owns an MSP in Virginia. Matt, thanks for joining us today. How are you doing? 

[00:00:33] Matt Yesbeck: I'm doing well, Carrie. 

[00:00:34] Carrie Richardson: I understand that, first of all, you have a business partner relationship that is interesting.

[00:00:41] Tell me about that. 

[00:00:42] Matt Yesbeck: Yes, my business partner and head of operations is my son, Gage. We partnered up in June when we opened our MSP. So far, so good. 

[00:00:53] Carrie Richardson: Now, are you partners in both ventures or only in the MSP? 

[00:00:56] Matt Yesbeck: Yes, we're partners in both ventures. As a matter of fact, [00:01:00] he was the one that identified the gap in the MSP space concerning contracts.

[00:01:06] It was his spark of an idea that got us together working on that. And then, A year later, we get into opening our own MSP. 

[00:01:16] Carrie Richardson: That's interesting because it usually goes the other way. MSPs usually build something that they believe has market viability and pillage the profitability of their MSP to build their new business.

[00:01:27] You're starting an MSP after starting a company that supports MSPs. 


[00:01:34] Matt Yesbeck: It's just circumstantial. We found ourselves both being laid off from our corporate MSP jobs, after MSPX was already launched .

[00:01:41] Five months into it and trying to work on that and gain traction on that while we're both collecting our biweekly corporate paychecks. Things came to a screeching halt, and we had to regroup and decide were we just going to go out and get other corporate jobs or we're going to take more control of our future and eat our own cooking, so to [00:02:00] speak, and jump into the business.

[00:02:02] That's what we chose to do. And so that's how MSPX came to be before YesTech. 

[00:02:08] Carrie Richardson: So originally it was more of a side hustle that you were building together 

[00:02:11] Matt Yesbeck: That's a good question. In the middle of the night when I wake up, the gears start turning. So sometimes nights are three or four hours if I'm lucky, but, it's that good kind of restlessness.

[00:02:20] It's two full time jobs, but it is so rewarding because we're building our own future. We're working together, father and son. We're supporting our families and we're building a community and certainly trying to contribute to the MSP channel.

[00:02:36] Carrie Richardson: So you mentioned that Gage was the one that identified that there was a gap in the managed services space. What was that gap? 

[00:02:43] Matt Yesbeck: He had come out of college in 2018 and he came to that question of what am I going to do with my business degree?

[00:02:49] And so with that, he was able to get in with a local M. S. P. Who graciously hired him on. He worked hard and worked his way up and absorbed it like a sponge and was [00:03:00] promoted to M. S. P. Director five years into that. One of the tasks was to essentially apply that pumpkin plan where he needed to look at their book of business and their P and L identify customers that needed to be pruned so that the more flourishing customers could grow.

[00:03:17] So in that process, he realized that there's just no good way to part ways with a customer, right? You can send them a dear John letter there. It's me, not you. It's certainly hurt feelings. The client feels left out in the cold. Now I got to go to a Google search and find what other MSP might be able to take our business.

[00:03:36] And if you're not technically minded, that's very scary. And then on the revenue side, Even if it was a break fix customer or a low MRR customer, it's still revenue that is gone .

[00:03:46] He brought that idea to me and we started doing searching and just could not find anything in the industry. Any platform, any means to facilitate a better parting. So we just decided build it ourselves and we [00:04:00] engaged our developer. worked on building out the marketplace for probably the better part of five months to get to what we have today.

[00:04:08] It allows that MSP that have identified those customers that need pruning, a place to go and list it on the marketplace, get one final monetization of that contract. And then get presented with other MSPs that you can negotiate with to place that customer, in what you would perceive to be good hands.

[00:04:29] And so it's much easier to part with that customer, knowing that they're going to be taken care of. You're not going to have bad word of mouth, which is huge in this industry. We can't have that floating around town, as well as being able to get one last, bump of revenue from that contract on the way out.

[00:04:45] Carrie Richardson: So have you noticed that managed service providers are collaborative in your community, or are they competitive? Do you get to know [00:05:00] the other players in your space or people closely holding their cards to their chest? 

[00:05:05] Matt Yesbeck: Yeah, it's a good question. we've identified a few dozen MSPs in the Richmond area.

[00:05:11] I'm at every business networking event that I can possibly schedule. All in an attempt to build, brand recognition and likeability and trust and all that good stuff.

[00:05:21] The events that I attend, I've probably met maybe four other M. S. P. Execs. Those people have been very receptive. We actually gravitated towards one another in those meetings and or networking events and talked for quite a while because We try to look at each other as collaborators, not competitors.

[00:05:43] Then probably the larger share of that few dozen in Richmond seem to be elusive or very private, not really wanting to engage with someone else in their space. 

[00:05:53] Carrie Richardson: We call it coopetition.

[00:05:56] In the call center space, for example, we would get a [00:06:00] lot of inbound calls that just weren't appropriate opportunities for us. And I hate the idea of someone having to end up with a company I don't trust or a company that I know to be

[00:06:13] unethical or underperforming, so I'd much rather help them find a nice home and give them some suggestions of competitors. And so I have a nice list of like people that I've maintained good relationships with.

[00:06:27] And one of those people bought my call center. So when it came time to transact, a lot of the advice he had given me, we had implemented. So transitioning my contracts over to him wasn't challenging because half of the things that I was doing, he had told me how to do Managed services isn't unique. And the way that you're delivering the service isn't unique. 

[00:06:49] Matt Yesbeck: Yeah, no, 

[00:06:50] Carrie Richardson: We use connect wise, 

[00:06:52] Matt Yesbeck: Yeah, no, absolutely. And I'll tell you that. the few good relationships that I've had.

[00:06:57] And again, I've gone to lunch with some of these people that [00:07:00] again are direct competitors, but, we look for ways that we can collaborate. And when I tell them that we specialize in, the Apple Mac platform, that's how I actually ended up having an out of meeting luncheon with a few of these people because they're getting, calls into their MSP about.

[00:07:18] support for these, platforms and they don't want it. they have customers that may have project work that involve the Apple Mac platform and they don't want it. So they look at me as someone that they can, white label a service for, leveraging what our specialty happens to be. So again, it's just identifying different areas within the MSPs that are here in Richmond, where we can collaborate together, We need to have that mindset because without that mindset, you can't really have a collaborative community of MSPs. 

[00:07:48] Carrie Richardson: What I've always heard is there are a lot of world changing ideas and there isn't a lot of world changing execution. Nobody can steal a client.

[00:07:58] If a client is unhappy, they are [00:08:00] going to leave. And that's not on nobody's taking them from you. You lost them. 

[00:08:04] Matt Yesbeck: Yeah, absolutely. And I think it's just a matter of ethics and integrity. If you're having to rip a customer another MSPs fingers, it's probably going to be fruitless because they're happy.

[00:08:15] So why in the world would that customer, and you're just going to create a bad name for yourself anyway. the customers that come to us have come to us. That door of opportunity is opened. I'm sitting in front of a prospect because they're disturbed and they're not disturbed because of anything we've done.

[00:08:30] They're disturbed because their current provider is dropping the ball in some way. And that's not my fault, but it is my opportunity. 

[00:08:37] Carrie Richardson: As somebody that did nothing but displace managed services competitors on behalf of other managed service providers, you're only 90 days away from hating your I.

[00:08:46] T. provider. Something always happens. 

[00:08:49] Matt Yesbeck: Or a few bad consecutive support calls. Especially if that's from a C level person or an owner that can form that opinion really quickly. So yeah, there's a lot of [00:09:00] work that goes into keeping those relationships strong. And again, if an MSP is doing all of that, it really makes me wonder how many, trunk slammers, might be, contributing to that.

[00:09:11] elusiveness, I don't know. I don't know, but I just know that yes, tech wants to collaborate with every MSP, in my area and outside of my area. I can be a resource of boots on the ground for someone in another state. Should they have one of their customers open a branch here, or they have a one time engagement that needs remote work done?

[00:09:31] I'm open. We do everything above board ethical and we operate with integrity. So there's nothing to hide here. 

[00:09:37] Carrie Richardson: I've seen, I have seen firsthand, we sponsored peer groups way back in the day. And I have seen the companies in those peer groups grow from million dollar MSPs into 50 million dollar powerhouses who are now active in the M& A space and they're going to exit for a significant amount.

[00:09:59] And [00:10:00] 10 years ago they were a million dollars in ARR with four points of EBITDA and couldn't figure out how to staff. I don't think you can go to your peer group and sit quietly and not tell anybody what you're doing and expect that you're going to thrive or learn or have anyone reciprocate and share their knowledge with you.

[00:10:19] And then you give back. 

[00:10:21] I see a lot of MSPs now who have moved on. They've sold their business and like myself, they get sucked back into the IT channel. They come in as consultants, willing to share knowledge. You've spoken to a couple of those organizations already.

[00:10:35] Encore comes to mind because you mentioned Pumpkin Plan and, they wrote a book, Pumpkin Plan for MSP. And for those of you who haven't heard about Pumpkin Plan, the book is by Michael Michalowicz. It's a great book. I recommend all business owners read it and, profit first. Also by Michael Michalowicz.

[00:10:55] Another great book. Pick up a twofer somewhere and [00:11:00] begin your entrepreneurial journey towards unprofitable clients. 

[00:11:05] Matt Yesbeck: And if your specific industry happens to be the MSP industry, Dave and Shawn essentially licensed the ability to rewrite that book with the title of Pumpkin Plan for MSP Owners.

[00:11:19] Carrie Richardson: There is a win episode featuring Dave when he released the pumpkin plan for MSPs.

[00:11:24] So you've got a brand new platform, brand new MSP. How do you spend your time? And what are you most looking forward to handing off when the time is right?

[00:11:38] Matt Yesbeck: Yeah, good question. So for MSPX, we are in A site refresh and new feature release phase, so that is taking a lot of our time, but it's exciting, as we strategize in how the interface is going to look, and the additional services that we look to release [00:12:00] here at the end of the first quarter, beginning of second quarter.

[00:12:03] Very involved and time consuming, but exciting. and obviously on the yes tech side, it's daily work for me to continue to build the brands, and market and sell to prospects here in the Richmond area. it is juggling. a lot of balls in the air.

[00:12:18] Young and full of energy. And I get up every day ready to rip and roar and so does my son and partner. So it's a great collaborative effort between the two of us to bring these both to life and get them flourishing. And then the end result, specifically for MSPX, I think we'd probably like to get that rolling really well, and see a large community, a build Around it and leverage it for the benefit of the entire industry, and then exit out of that.

[00:12:49] Sell that off to, a larger, entity that can take it and continue to run with it and build it out, to be the best version of its possible self, right? [00:13:00] Yes. Tech. that's something that's more generational. and it's, that's the ideal anyway, getting into it right now. I don't know what that's going to look like 10 years down the road.

[00:13:08] if we. are doing extremely well, and we're very well organized and positioned for, a possible, exit. We could entertain that, but for now, we're just looking at it as something that we can build as a family, and, to the benefit of our grandchildren and great grandchildren.

[00:13:26] We'll see how it goes, right? Because technology is always shifting. We don't know what that's going to look like in 15 years, 5 years, 10 years, But that's the overall ideal. 

[00:13:34] Carrie Richardson: You talked about a delineation between yourself and Gage, where Gage is more content on the operational side of the business, and you're more, focused on the sales and marketing part of the business.

[00:13:48] How do you decide, as partners? What's going to happen? What's the I know I run a business with my husband. We don't always agree on [00:14:00] things. He is the managing partner of our business. His word is final. So I, my opinion matters. But I don't sign checks. I don't sign contracts and I don't make the final choice.

[00:14:10] How do you resolve conflicts when you don't agree? 

[00:14:14] Matt Yesbeck: And for he and I, we are a straight down the middle 50 50 partnership. I am his father, so there's certainly some seniority and authority there, but I in business, try to never exercise that, right? 

[00:14:27] We understand that but we talk everything out and yes, we don't always agree with the direction and sometimes we'll just let that percolate and revisit it, and just try to whittle it down to where both of us are happy with whatever move we're going to make. And that's worked well so far.

[00:14:44] And typically again, like the operation side is really his side of the business. And so even though he'll talk to me about. tools he might want to use or things he might want to implement on the operation side. He does involve me in that thought process. I largely leave [00:15:00] it up to him to make those choices.

[00:15:02] and I would say the same is true on the business development side for me. we again are always strategizing on how to best position the business from a sales, marketing and business development perspective. And he has a lot of good young, fresh ideas and suggestions. And I certainly always, value that feedback.

[00:15:21] But yeah, sometimes it's contentious. and there's some friction there, but that's just to be expected, whether you're related or not. I think for us being related we are much more, willing and quick to, settle any arguments or disagreements, much faster with fewer hurt feelings.

[00:15:40] And so I think that is going to be the glue that really holds us together, for the longterm. 

[00:15:45] Carrie Richardson: And what do you think your first hire will be? Your non family, who's your first non family hire? What role will they have? what are you most looking forward to handing over to another person? 

[00:15:56] Matt Yesbeck: I would say that if I'm doing my job correctly, [00:16:00] it's going to be an engineer, we're going to need to hire someone to assist gauge. With the customers that I am bringing on board and to support them in the way that we had positioned that we would when we sold the deal.

[00:16:13] I wanna make sure that our customers always have an exceptional customer support experience, and that, they've always got, knowledgeable hands on the keyboard to be taking care of, their infrastructure and their needs. And then of course, for me, on the business development side.

[00:16:28] following through with the QBRs and making sure that we're strategizing with the customer and highlighting things that they can do from a technical perspective to, help their business be more efficient. and yeah, to answer the question, I think we'll probably end up needing to hire an engineer first now.

[00:16:42] I've spent nearly three decades in the MSP industry, but on the technical side. So I really had to, educate myself, on the marketing and sales and development that I'd never had to worry about before, because someone else was doing that and hiring me and putting me on a contract to handle the technical side of things.[00:17:00] 

[00:17:00] Thankfully, I do have a personality. I'm affable. I'm somewhat, extroverted. I can walk into a room and comfortably meet people and start conversations. And it really, to me, it's just building the additional knowledge needed from a marketing and sales perspective.

[00:17:12] and there's a lot of, live and learn stuff, but that's why to your point earlier, peer groups or mentors are so important because they can really help save you a lot of time, heartache and money. and so I've really been leveraging the knowledge of other gracious people. 

[00:17:29] Carrie Richardson: So both of you came from corporate I. T. backgrounds. What's been the most surprising part of being an entrepreneur? What did you not expect? 

[00:17:37] Matt Yesbeck: The saying goes, you don't know what you don't know. We didn't get into this with any preconceived notions of ease.

[00:17:44] we certainly understood. The technical side of things, because that's what we were both doing. and we knew there was this whole layer of business operations, and finances and business expenses and all the things that go into owning a business, the tax [00:18:00] preparation for it, all these things, that we were never doing firsthand.

[00:18:03] So we knew there were going to be challenges in that respect. and so we've just tried to be very, sensitive to those areas And just try to do the best that we can to make sure that we are doing it correctly. But again, that's why peer groups and mentors are so helpful because they can speak to these things.

[00:18:21] and really start the gears turning in directions we weren't even thinking of because we're not that large yet. so you talk to an MSP That's two or three years down the road from where you're at, and they give you some really great insights. So you know where you're heading, if you stay on your growth track, and then the things that you're going to need to implement to make it successful.

[00:18:43] There are many things we didn't know, especially on the business development side of the house. We were very confident with our technical knowledge and ability. but it was the whole BD side of things that, we knew we were somewhat blind to.

[00:18:56] Carrie Richardson: So with the platform, which isn't the same really as running an [00:19:00] MSB, you both knew how to provide IT support. It'll be your first foray into, an internet marketplace for lack of a better way to describe it. any surprises on that side of the house? 

[00:19:11] Matt Yesbeck: Surprises, man. It's every day it was something new when it comes to building out the platform.

[00:19:17] we had reached out to many MSPs just to get on the wait list, just to send out really a poll to say, Hey, this is what we're. in development to bring to the market, what would your interest be? We had, three or four questions that you could answer in an email and give us the feedback and the demand for something like that was very high.

[00:19:39] So the feedback was absolutely promising. and then some of the other pointed questions that we asked helped us to, shape. How the platform was gonna work. I guess one of the surprises would, be the amount of excellent feedback we got, within the community of MSPs that we're looking for, and excited to see the [00:20:00] release of a platform like this.

[00:20:02] Carrie Richardson: I'd like to give shout outs to people that are helpful. 

[00:20:04] Matt Yesbeck: Then here you go.

[00:20:05] I would certainly say that Doug Lowenthal from MSP fuel. Has been an absolute gem of an information sharer, and he has been very generous with his time, especially in the last few weeks. And so I would definitely shout out to him, in recent memory. And everybody else, honestly, that I'm not thinking of right now.

[00:20:28] You win an Oscar and you're all these people you want to thank and you just go blank. I want to thank everybody That's given me any of their time, any of their platform. Carrie, thank you for allowing me to come onto this podcast and speak about MSPX, and everybody else that's willing to give of their time.

[00:20:44] Carrie Richardson: to allow me to try to bring more exposure and awareness to what we're trying to bring to life. So thank everybody. 


[00:20:50] Everybody deserves a shot at being an entrepreneur. Not everyone's built for it, but. I wouldn't trade. even the worst day owning my own business [00:21:00] was a pretty good day compared to having to come in and punch a clock for someone else.

[00:21:06] Matt Yesbeck: Yeah, absolutely. in terms of the collaborator versus competitor thing, I find the MSPs that aren't in my immediate area are much more friendly and much more willing to impart, right? Because they don't feel any direct competition. If they're further away than that, it seems to be an open community that, is, open to share. 

[00:21:30] Carrie Richardson: I think you'll definitely find that in the hallway of any event that you attend in the MSP space.

[00:21:35] Like the people on stage are great, but where I'm learning the most is usually sitting, having a cup of coffee with somebody at the breakfasts or a quiet chat. 

[00:21:46] Yeah, absolutely. 

[00:21:48] Thank you so much for joining us today.

[00:21:50] Carrie Richardson: I look forward to watching the development of MSPX. 

[00:21:53] Matt Yesbeck: Please check out the marketplace . It's the Internet's first marketplace for the buying and selling of managed services contracts.

[00:21:59] [00:22:00] you can visit that at www dot mspx dot store. there's a little video there where you can watch that minute long video. There's a nice long landing page that gives you some really good information, some blogs at the bottom. if you would like to sign up and log in, please do.

[00:22:17] Carrie Richardson: Welcome to the channel, Matt. I hope we treat you well. 

[00:22:20] Matt Yesbeck: Absolutely. Oh, and one more before I part, and then I can be reached at Matt at mspx. store. 

[00:22:26] Carrie Richardson: All right. Thank you so much for joining us today. 

[00:22:30] Matt Yesbeck: Yes.