Confessions of an IT Business Owner Podcast
Confessions of an IT Business Owner Podcast

Confessions of an IT Business Owner

Confessions of an IT Business Owner podcast is a podcast published every two weeks, where we share inspiring stories of IT Business Owners, just like you, on how they’ve become healthy by improving their cash flow, automated their businesses, and built trust with their clients and prospects by looking more professional, ultimately growing their MSP’s.

Listen to our latest episode:

Episode 1 – Confessions of an IT Business Owner – ft: Scott Spiro

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Scott Spiro, CEO of Computer Solutions Group.

Episode 2 – Confessions of an IT Business Owner – ft: Bob DeLisa

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Bob DeLisa, CEO of Cooperative Systems.

Episode 3 – Confessions of an IT Business Owner – ft: Angel Rojas

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Angel Rojas, CEO of DataCorps Technology Solutions.

Episode 4 – Confessions of an IT Business Owner – ft: Joy Beland

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Joy Beland, CEO of Pink Hat Technologies.

This episode is sponsored by and Check out Josh Whitford and his offering at, and learn more about the perfect channel only offering for your IT firm and MSP business at

Episode 5 – Confessions of an IT Business Owner – ft: Jason Etheridge

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Jason Etheridge, CEO of Logic Speak.

This episode is sponsored by and Check out Josh Whitford and his offering at, and learn more about the perfect channel only offering for your IT firm and MSP business at

Read Transcript

Dave Scott: Hey everyone, welcome to another edition of the Confessions of an IT Business Owner Podcast, where we share stories about how healthy cash flow is critical for the health of your IT business, automation is paramount, and how building trust with your clients by looking more professional is going to help grow your business. I’m your host, Dave Scott, and today, we’re honored to have with us, the CEO of Logic Speak, Jason Ethridge. Today, we’re going to chat about some pretty in-depth things about the wins and losses inside of what it takes to grow an IT business.


Jason Etheridge: If we’d have continued on that path, we would have imploded, because we would have never been able to keep up. And, all of the growth that we had experienced would have eroded.


Dave Scott: Here’s the podcast with Jason.


Hey Jason thanks a lot for joining us on the Confessions of an IT Business Owner podcast. I appreciate it and appreciate your time very much.


Jason Etheridge: Thanks for having me.


Dave Scott: Talk to me a little bit about the name of the company where you were from and what you all do. Let’s start out with your baseball card stats?


Jason Etheridge: There you go. So my company is Logic Speak. We are a managed services provider here in Atlanta, Georgia. And we’ve been in business for almost 14 years now. We started our company in 2004.


Dave Scott: Well, 14 years. That seems like a long time in business years, doesn’t it?


Jason Etheridge: That’s like a lifetime in dog years.


Dave Scott: It is. If it was a Chihuahua, you’d be old and gray underneath your chin. So Jason, talk to us a little bit about the problems that your MSP solves and maybe if you want, this is all about you, so do you verticalize, do you specialize on one thing? Do you service just health care, nonprofit, education small B2B business? So talk about the vertical that you serve and maybe the problems that you’re solving for your clients.


Jason Etheridge: Yeah. Great question. We don’t actually do verticals yet. We do have core competencies in a couple of different verticals but we haven’t yet said, “These are the verticals that we service.” Essentially what we say is that we focus on professional services companies, generally B2B companies, that primarily use technology for their business. And so, the problem that we attempt to solve is to bring proactive managed services to the client so that they’re down less often, so that they are more efficient, more productive and ultimately, we’re more profitable because the less time they’re down, the higher our margins.


Dave Scott: That makes sense. So talk to us, you touched a little bit about the pain points you saw for businesses, but who is your ideal business, who is your ideal persona or your ideal client and why?


Jason Etheridge: Yeah. So, throughout the maturity of our company, just like many small businesses, you start by doing work for anyone who will pay you and you’ll do anything that they’ll pay you to do. And over the last 14 years or so, we have started to mature and grow and knowing who we are, we’re a teenager now. We think we know who we want to be, and so, we focus on companies that are anywhere from 20 employees all the way to our largest customers, about 400 employees strong.


Engineering is a good target for us. The engineering space, I happen to be married to an engineer, so I kind of have it in there and the inside track on the unique challenges of an engineering firm. And then, we are also really heavy into the financial services sector. Financial planners, accounting firms, CPA and tax firms as well.


Dave Scott: I like it. Yes, being married to an engineer sounds crazy cool, I like that.


Jason Etheridge: It has its unique challenges as well as its unique benefits. We are two small business family, we also have a two year old and so we like to say we actually have three kids.


Dave Scott: That is awesome. So is she a partner at this firm or she just works there is a W-2 employee?


Jason Etheridge: No, she owns her company as well. We are we’re fully immersed in the entrepreneurial spirit. Let’s say it that way.


Dave Scott: So talk to me a little bit about that. Let’s go down that path because typically, what we find in with our partners, MSPs, is that it’s usually a husband or wife team. Wife will do sales, marketing, bookkeeping whatever. The husband might do the actual implementation, onboarding, technical aspect or vice versa of those roles, it all varies per company, but that is super unique. How does that work inside of your house every night?


Jason Etheridge: It works on an ongoing basis. We have to be very intentional. Her company is a little bit younger than mine, like I said, we’ve been in business for about 14 years, she’s been in business for about five or six. I probably hit certain milestone before her. There is a tendency to want to participate each other’s businesses, to give each other advice. And we do that when requested, we certainly talk a lot about business at home. But we decided very early on that we wanted husbands and wives and business partners and that we couldn’t do both.


I know a lot of people who are husband and wife teams. We both are type-A red people, if you are familiar with those kind of terms. We decided we couldn’t really work for each other. But we do talk a lot about business and of course I provide all the IT support for her company. If we’re not intentional, work can take over and we’ll put our son to bed and go sit at home on our laptops and work through the night. There’s a tension between spending time at home with each other and focusing only on work.


It’s one that we constantly manage, and don’t always get it right and the pendulum swings back and forth. But we try our best is to both have really healthy family lives as well as focus our business as well.


Dave Scott: Good for you guys for being committed to doing it. And yeah, I love that word intentional. That’s a word we use a lot around here in the office. I got to imagine carving out time for yourselves and your family and your little boy. That’s got to be challenging, carving out time and not becoming overworked, so to speak.


Jason Etheridge: It is a daily intentional thing, that’s for sure.


Dave Scott: Yeah. One of our guests, Bob De’Lisa, he was on our podcast a couple of weeks ago and he talked about your business being your mistress and you can get lost in it. And if you’re not intentional with your time, it can not only be good, but it can be really bad, so I’m not sure if he can relate to that sentiment.


Jason Etheridge: More than you know.


Dave Scott: Yeah, I bet. So talk to me about the role inside of your company. And thanks for sharing what you did about your family dynamic. That is really neat. What’s the role, what role do you play inside of Logic Speak, Jason?


Jason Etheridge: Yeah. The good news about having the growth that we had and we certainly are still a small business, but we are at least to a point of what we call mass. We have a critical mass where I have made it to just being president and participating in the sales organization as well. But, I don’t on a daily basis take tickets, I’m not working in the business on the boots on the ground side of things. I really do get to focus more on, and not exclusively, let’s not kid ourselves.


I’m still a very technical resource. I do still help out from from an architecture perspective on projects as well as escalation of really complicated problems, I’ll certainly weigh in on and try to help, but my primary job is vision casting, leading the organization, managing our finances with my accountant, kind of from a high level. It’s funny, we talked about this today, me and my service manager, looking over the trees down at the horizon, not getting buried in each tree, each project, each deliverable.


Dave Scott: Yeah. I wish more CEOs practiced that. It’s so hard to let go of a lot of those things you’ve been doing for so long, you know what I mean. So it’s really difficult to look over the trees, so to speak, and not get down into them, isn’t it?


Jason Etheridge: No. For several years now, I’ve had kind of a word of the year that I talk about in our company kick off and then we try to tailor things around in terms of what we want to accomplish for that year. And the first time I ever did that, my first word of the year was intentionality. That we should do everything as if it were on purpose, and that we have to intentionally decide what we’re going to accomplish. It’s a very important to me, actually.


Dave Scott: There’s a pastor friend of mine named Matt Chandler and he was diagnosed with brain cancer about six or seven years ago. He was in his late 30s by that time. And after he went through that bout of cancer and he got cured and everything and moved on from there, that was really his word, being intentional.


He’s a super intense, focused, very goal driven individual. I feel like you have some of those attributes and I love that about individuals who really put that into practice and it’s hard, it’s hard to not get distracted and waste time. Butt to your point, it’s so important we have such a limited resource of that. So it’s good that you guys figured that out.


Jason Etheridge: Well, we try. Every day is not a a success, but when you’re trying to do that, when you’re being intentional, even if you fall off a horse, even if you fall off the wagon, the next day you hop right back on and set about accomplishing the goals that you set out. And it’s clarifying. From a vision perspective or vision casting perspective, when you set your mission clearly ahead … And everyone in our company knows what our mission is because I have literally plastered in almost every room of our company.


Because I want people to see it every single day as they walk through our office, I want them to constantly be reminded of what we’re here to do and why we’re here essentially. And so, that’s important.


Dave Scott: Jason, talk to me about … Speaking of intentional, let’s be intentional and talk about some of the wins that you’ve had over the years. Share with us, if you could, about maybe some of the top couple of victories or wins that you’ve had over the last 14 years.


Jason Etheridge: Yeah. I’m happy to. Probably my story, in a lot of ways, mimics a lot of your listeners. When I started out I was working for another company and we got gobbled up and acquired by Hewlett-Packard. And so we went from a company of 200 something employees to 140,000 employees, which, talk about culture shock, that is the very definition. I worked there for a while and then my business partner, who I started Logic Speak with and I decided that it was time for us to branch out on our own and that we really had a passion for the small business.


And that’s what we had known and where we had cut our teeth. That’s when we started Logic Speak, and ultimately, the name Logic Speak comes from the fact that we want to translate technology into the terms or into the language that our customers speak in the business so that we’re not using three-letter confusing acronyms and geek speak, that we’re actually translating what we know how to do into our customers business. So, that’s where the name came from.


We grew, our first three or four years were high growth, double, triple year revenue. People find out that you’ve struck out on your own, so you get a lot of organic growth that way. And then in 2008, we hit the housing crisis and thankfully, we weren’t that tied of the commercial real estate industry so we had to hang on with both hands. And we took a haircut. People always ask me, “What was that like to go through and what you do it again?” And certainly, I would never choose to do it again,.


But I will tell you, that that was a very clarifying time for our company because we had we gotten fat and happy, money had always come in. We never really struggled for money before and had some pretty big name client that helped keep us from worrying about money. But again, we’ve gotten fat and happy and weren’t as concerned with the profit margins as long as there was money in the bank. Money was increasing every month and so it was no big deal.


So when the housing crisis hit, we were forced, as many companies were, to have to learn how to do more with less. And ultimately, to have a hyper focus on efficiency. And those lessons that we learned in 2008, while I wouldn’t choose them to do again man, I wouldn’t trade them for the world because it has shaped the very nature of who we are as a company, and our focus on metrics and our focus on efficiency and productivity.


Those things we’ve got, we cut our teeth on those things during the crisis, that’s been a huge win. We made it through that. Like I said, we all took haircuts and we made it through that and then started growing again as the market started to improve and kind of really started to hit those, not necessarily double and triple, but really consistent growth rates. And in 2012, my business partner who I started the business with, he had two kids had a wife and that was getting burned out.


And I at the time was still single and so I carried the mission that we had originally started with and the vision for the growth that we wanted to accomplish. So we made the decision that that one of us was going to buy the other out, and since he was burned out and I still carried the mission, that it would be me bought him out. It was a very interesting process, which we could talk for a whole another podcast on, about the process of valuing your company and trying to decide what its worth to you, if you’re going to buy it, what ultimately you intend to do with it and what its value has for you.


So I did that. We negotiated on a number over the next three months or so and he felt like he didn’t get enough and I felt like I paid too much, which means it was probably the right number. And then when the deal is done, the dust has settled you sit back at your desk and this thing that you now own outright or after three years when the payments are made, the thing that you own, you now have to decide, what is the state going to be? What do I want it to be?


Dave Scott: Because now it’s yours.


Jason Etheridge: Yeah. Now it’s yours. There’s no one else to blame. Young can’t say, “Hey, this guy didn’t do what are you supposed to.” It is now yours. The first thing that I did, and I don’t really remember why, it probably was via a leadership podcast, that I’m a big fan of that I started to learn about this, but I really wanted a clarifying mission. I needed something to laser focus, sort of point my employees to as what was going to be Logic Speak 2.0. And the example that I’ll use, real quickly is that, when we started our company, you go through the business planning, you kind of follow traditional business planning and, “Oh, what you need is statement of value, you need a mission statement, you need all of these things.”


And so we had this big, long mission statement there was three paragraphs and talked about shareholder equity, all kinds of stuff that no one cared about. Nobody ever read. And if you asked any of our employees, they couldn’t tell you a single thing about it. So I started the process of creating a one sentence mission that encompassed what I believe and what I wanted Logic Speak to be, and that’s what we rallied around and that’s what I rolled out as Logic Speak 2.0.


If you’ll indulge me, I wanted to tell you what our mission is. Our mission is to use our our abilities and technology to have a positive impact on the lives of our clients and our employees. So it doesn’t say anything about shareholder value. It doesn’t say anything about business success or all of these things. At the end of the day, I feel like I’m put on a planet to have a positive impact on the people around me. And by way of extension, that’s what my company is here to do.


We’re here to serve people and have a positive impact on their lives, and if we’ve done that, then I feel like everything else will work itself out.


Dave Scott: I love it. There’s one thing I want to go back to though, and that is a awesome mission statement. I love it, super clear, super succinct. Tell us what you do from a technical as well. So I love that addition in there. You talked about when you had parted ways with your former business partner, and by the way, it sounded like it went as good as it can. And there’s a friend of mine who owns and M&A company that actually services the IT industry. They’re called Revenue Rocket in Minneapolis.


And I hear all about the trials and challenges of M&A and buying out partners and buy-cell agreements. So yeah, I can totally relate to.


Jason Etheridge: It’s emotional when it is something that yo-


Dave Scott: It is.


Jason Etheridge: It’s like Solomon splitting the baby. You’ve got to take this company and decide who’s going to take the baby or or split it up. And fortunately, Jared and I, he is a man of integrity. He never wavered in that. And so we were able to have a very calm, rational but sometimes emotional conversation about the value and the end of the day, we’re still friends. He’s moved on to another company and so we still get together every three to six months and chat and commiserate and laugh and cry together.


I really feel good about that because as you said, I’ve heard horror stories where courts get involved. It’s just awful, but it went really, really well.


Dave Scott: Do you ever miss it? Do you ever miss having a business partner to bounce ideas and thoughts on and lean on in times of trial?


Jason Etheridge: That is a great question actually that no one has ever asked me. You are person number one to ask me that question. I will tell you what I do miss, I miss the camaraderie. I miss being in the trenches with somebody where there’s no other choice but to succeed together. I kind of miss the shared, ho about this, the shared yoke, the burden that you can walk with somebody.


My advice to people today when they talk about starting businesses, especially if they start with a partner is that it shouldn’t be 50/50. We started with the best of intentions, we started with shared focus and shared goals and shared ideals. But it’s like I believe in a marriage, it has to be 51/49, at the very least because at the end of the day, somebody has got to be the tiebreaker. And if you’re not, then you ultimately, and this is what we fall into, you ultimately make decisions based on the nose, based on, we can’t agree on this, so ultimately the opportunity passes by.


It’s not a very good business practice to make decisions based on what you can and can’t agree on. If Jared and I had been for 51/49, we might still be in business together today. But but when you’re 50/50, it gets to be very challenging to make each other agree on things.


Dave Scott: Yeah, it can. And I was in business with my college roommate, best friend. We’ve known each other since we were, gosh, 18, 19, 20 years old, whatever it was, and we’re both in our 40s now. And yeah, when I left that partnership, when I left working with him on a daily basis, that was the biggest thing I missed. I didn’t miss … I miss the daily grind and the sludging it out in the trenches, you know how it is.


You’re working together for a common purpose and your serving customers and hopefully making people’s lives better, and making a few bucks for yourself as well. But yeah, the camaraderie, the sharpening of iron as iron sharpens iron. That was a big thing that I missed, that we don’t work together every day anymore. And yeah, it sounds like you can totally relate.


Jason Etheridge: And what I found, just real quickly for your listeners, the way to replace that, especially as you get to a certain size, because as you mentioned it does get very lonely at the top. And it gets stressful because that ultimately the buck stops with you every single time. That can be a very isolating feeling. I worked with an executive coach and his recommendation to me was, even if you’re the only owner, you should have a leadership team around you that can share the burden. I have never done that, because I didn’t want to burden other employees.


I didn’t want them to feel like they had the burden of the company when they don’t have any ownership. But he asked me a very clarifying question, he said, “When you were working for another company, if the CEO of that company had invited you into the conversation in terms of the leadership of the organization, would you have felt like it was a burden or would you have been privileged to do it?” And I said, “Oh my God, I would have loved it. It would have been amazing to be part of the conversations.” And he said, “Why would you rob other people at your company of that opportunity?”


I did that and now I have a leadership team and we meet twice a month. And I literally, I have hands open in that meeting. I tell them it’s a meeting of equals, it’s not me versus them or me telling them. It is literally us around the table, deciding how we’re going to lead this company forward. And I can bring tough decision to them, “Hey, we need to let go of an employee, hey, here’s our revenue, here’s our net profit. Have a look at it, and tell me what you think.” It has helped me to be able to again, have that camaraderie, have the partnership of people who care about moving the company forward.


You got to pick really good people to be on that leadership team. But if you do, they’ll help propel you forward and you’ll be able to replace that feeling.


Dave Scott: I completely agree and dude, that is so spot on. There is a book that I have in my office, I’m actually looking at it right now called, Team of Rivals, and it’s about Abraham Lincoln’s choice of his political cabinet. The whole point of the book is, he found success, incredible success because he surrounded himself with good individuals, some of whom were really stubborn and appointed, and direct, but that made them sharper and better as a team.


They all had a deep profound respect, love and care about each other, and they all expressed that in written word. So, it’s a really touching book and it’s a really good book, you should read it sometime.


Jason Etheridge: I’ll check it out. Similarly, I read The Big George Washington biography, and it’s funny you mentioned that. George Washington did the exact same thing. He had Hamilton and Jefferson, who were arch rivals and they were part of his cabinet.


Dave Scott: So, talk to me about the day you left your old 9 to 5 job, and it sounds like you possibly were acquired. Let’s go back to that for a minute, you touched on it a little bit earlier. What was the feeling like, the instant or maybe the moment that you knew that being self-employed was the direction you were going to go in? Talk me through that day where you left your normal 9 to 5 and ventured out to create Logic Speak.


Jason Etheridge: Sure. To back up just a step, when my business partner that I started the company with, I actually recruited him to work at that company that we got acquired at together. I recruited him to come work for me, and he said to me, he just got married and he said,” I will come work for you at this company, if you all agree that within five years, will talk at least about starting our own business together.” And so, I said, “Hey, of course.” I didn’t know it would come so soon. I said, “happy to do that.”


And it was only eight years later when HP bought us. So, it was very prophetic that that would have happened so quickly. But in terms of starting our own company and how I felt about it, I know this is going to sound weird, but I think I was just young and excited enough that from a risk perspective, I calculated everything based on the probability of something happening or the risk that something would happen. And so, I’ve never been one to shy away from a calculated or a strategic risk, or one where I believe the probability ways in my favor.


And so, I never had any sort of fears around starting my own business. I think I was young enough as well, I think I was 25 or 26 at the time. I didn’t have a family, I didn’t have a wife and a child to support. So I knew that if everything fell apart, that I had a network of really close friends and family that any of which would take me in. And so, you have to be willing when you have your own shingle out there or when you start something.


It’s like Columbus, when you get to the new world, you burn the ships. And that’s what I did. It took me a while again, to leave HP. And of course, Logic Speak was well underway at that point, we had everything planned, and we had our business plan. And our first client even. It was really perfect timing. I got the call, “Hey, I’m sorry, I’m really sorry you’re going to be laid off.” And they granted us the seniority from our own company.


So I got three months worth of severance, and that three months salary, was really the foundation of the investment into Logic Speak. I wasn’t upset at all, I’m like, “Oh okay, no problem, we’re good.” And so they were shocked that I wasn’t upset. Well, long story short, the HP transition team got word that I had been laid off, and I was the only one who knew anything about the infrastructure. So they made their way back to HP’s HR team and then made it back to me and then they said, “Congratulations, you’re not laid off anymore.”


And I said, “No.” And they said, “What?” And I said, “Well, no, you promised, I’ve already made plans. I’ve got things working and you can’t unlay me off.” Turns out from a legal perspective, they actually can’t unlay you off, but they made side deal with me, that if you agree to say one more month, we promise to lay you off again.


Dave Scott: So, did this sweet severance come along with it, once they re-laid you off?


Jason Etheridge: It did, exactly, because if they wouldn’t have done that, which they were nice and honored that. But if they hadn’t, I would have to quit with nothing. Instead, I got three months severance.


Dave Scott: That’s interesting. How did your family feel about your transition? Maybe those close to you not necessarily your family because it doesn’t sound like you weren’t married at the time, but what did those around you say to you when you decided to venture out and start your own IT firm?


Jason Etheridge: Thinking back on it, I think that was one of the coolest things, is that everyone to a person, was super supportive. Not everyone had advice for me, a lot of my friends and family, non of them at that age had started their own businesses before, but I just remember this outpouring of support for what we were trying to do. There was excitement around it, people were constantly interested in how it was going and how things were progressing. And I feel kind of like it takes a village.


Certainly, when you’re going to do something like that, when you’re birthing a business and creating something from nothing, it’s invaluable to have a network of friends and family who get what you’re trying to do, who are supportive. And let’s face it, who understand when you have to miss that family reunion, or when you have to miss the guys hanging out to play poker, because you’re working all night.


There’s a lot of sweat equity that goes into starting a business, and having people that understand that and who are willing to support you, and who bring you a pizza, when you can’t look up from your computer to stop, that kind of a thing, it’s invaluable. Not that you can’t do it without it, I know some people who have done it without it. But it certainly made that time of my life, a lot less lonely and a lot more bearable. To have the underpinning of really close friends and family who understand.


Dave Scott: Yeah. No doubt in that you too, you hit the nail right in the head, it does take a village to grow a business. It does. You can’t do it on your own. And the more that you do try to do it on your own, the worse it becomes. So, I can totally hear what you’re saying on that point.


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Dave Scott: So, talk to me about the why. What keeps you going? You’re doing all these things, you left your security, you ventured out. You had, sounds like a really great support mechanism, which is fantastic, very few people have that. Knowing all that, that’s the functionality of it. Talk about the forum, like what’s the why, what keeps you going everyday? When you put your feet on the floor at 4:00, 5:00, 6:00, 7:00 am. What keeps you motivated to keep going? What’s the why behind it?


Jason Etheridge: Yes, so really, as we mentioned what our mission is, is an outpouring and a flowing of my personal mission in life. And so, I love to come to work every day, I’ve had this conversation with other people who are like, “Oh man, I hate my job, or I wish I didn’t have to work or I wish I could change careers.” A lot of these things. And I my heart goes out to them because I recognize that not everyone gets to love their job. It’s certainly a benefit and you certainly can use a job to pay for the things that you are passionate about in life.


So, there’s a model for that as well. But in terms of me, I get to get out every single day and come to work and do something that I love. And the other thing that makes it really possible is, I get to surround myself with phenomenal people, people who get our mission. People who are all in and engaged in helping us to get further or faster and to do great things. Literally, I’m looking right now, if you look above my door in my office, walking out into our kind of bullpen area, it is the word serve.


And really, what I’m passionate about is serving other people, I’m a servant at heart. I love helping other people, I love that feeling that you get from knowing that because of you, someone’s life was made better. And so, that’s why I keep doing it. And as long as Logic Speak gets to do that, and as long as I get to work with really phenomenal people, who really make this place work, then I’ll keep doing it. There’s no reason not to.


Dave Scott: That’s awesome. Man, looking back over the last 14 years, there’s got to be some points every once in a while, where you just put your foot up or feet up on your desk or whatnot and looked back and said, “Man, we’ve really accomplished a lot.”


Jason Etheridge: That’s true.


Dave Scott: That’s awesome.


Jason Etheridge: And it’s one of those things, so funny you mentioned that. If you’re not careful, especially as a small business when things are really, really fast and it’s so fast pacing, everything is changing and moving so quickly. One of the things that I talk to budding small business owners, or people who’ve been in the business like a few years or certainly, my wife and her company, is that you have to take that time to look back. Not all the time, because we all want to advance, we all want to progress, we all want our businesses to grow. We all want to take over the world, we want to succeed.


But you’ve got to have that time, that really still quiet time, to look backwards and see how far you’ve come, because if you don’t, like we talked about before, it is lonely and it gets daunting, and what is it all for? And is it all worth it? But if you can stop and look back and see how far you’ve come and what you’ve accomplished, then it will give you momentum and it will propel you forward to go further. It’s kind of losing weight, like you lose weight one pound at a time, when you look up and you’ve lost 30 pounds and you see somebody after six months, and like, “Men, you’re so skinny.” And you’re, “Well, I feel like I’m the same as I was.”


But that’s because you don’t see those small increments of investment over time. Same thing, you have to look back to be able to appreciate.


Dave Scott: I know firsthand how tough it can be to run a business and own a business. Let’s talk about some of those struggles, some of your peers might have delivery struggles, maybe some of your clients have left en masse, hopefully that hasn’t happened to you because that sucks when it does happen. Talk to me about some of the more prevalent struggles that you’ve worked through over the last few years.


Jason Etheridge: Sure, absolutely. Certainly, one of the struggles, when I bought the company outright, the first thing I had to do was evaluate everything that we were doing. And also the excitement around buying out the company and the single vision, and the single voice, casting vision. There’s an initial uptick for your company in terms of additional clients and growth and that kind of thing. We found ourselves, our client base and our revenue grew faster than our internal maturity and systems were growing.


And so, what that causes is, overwhelming your people, overwork, constant frustration with your clients who love you and want you to do what they need you to do, but if you can’t get to them fast enough at the end of the day, they’re going to find someone who can. And so, we really have a crisis of maturity back in those days, it was about, I guess, now five years ago. We really had to look at how we were doing everything that we were doing, what systems were we using, are they the right systems, are they going to propel us forward? Or are we suffering?


And the way I always said to my employees, if we had continued down that path, we would have imploded. Because we would have never been able to keep up and all of the growth that we’ve been experiencing, would have eroded, not overnight, but certainly when we weren’t able to keep up.


Dave Scott: And that is so important to understand that early on, to work through some of those struggles because to your point, if you don’t, the wheels will come off the bus very quickly.


Jason Etheridge: And we have experienced that. You mentioned that kind of mass exodus, the way I’ve said it to my employees, is that, “If you don’t handle your overwhelmed problem, your customers will handle it for you, they’ll leave and you’ll be less busy. It just might not be the customers that you want to leave that are going to leave. And so, you should do that again, intentionally and decide which customers are the right customers to work with, and which ones aren’t or else they’ll pick for you.”


Dave Scott: One of the things that we do, is we focus on building a good clear persona, like, what are the problems and the pain points that we solve overall, for who we think are ideal prospect is, and our ideal partner is. And then we also identify who isn’t, because you don’t want to be wasting people’s time, going back to being intentional, like we talked about earlier. To your point, you have to be you have to be willing and be careful to understand that everybody is going to grow in certain respects, and you have to be just cognizant aware of that.


Jason Etheridge: It’s who you choose not to work with, is everybody as important and sometimes more important as who do you chose to work with. I think a lot of times we forget that, and we’ll take whoever will pay us, but if you’re spending time on companies … We call it fitting them into our box. We have an ideal customer and either customers are moving toward that box and getting in that box or they’re already in that box, or they’re moving away.


And if they’re moving away from our box, we need to help them find the right company to service them because we are not that company. And that’s critical because it will allow you to focus your margin on the customers that do fit your model, that do recognize your value, that do participate in the maintenance of their own systems and they see the value of managed services. So, I can’t echo that strongly enough.


Dave Scott: So, automation is critical to any business as you know, talk to us a little bit about the processes that you’ve automated and also talk about some of the tools that you use as well.


Jason Etheridge: Sure. Well, and that kind of dovetails is really nice where we were when I bought the company. When I bought the company, we were using our own custom developed help desk solution, which again, worked well for what we did, but it only did two things really well as opposed to the entire landscape. And so, we did that for help desk, and then for billing, we literally manually entered invoices into Quickbooks every single month.


I mean, literally talking about inefficiency. That’s why I say, we were literally imploding, we could not keep up with the growth from a financial perspective, from a billing perspective, and certainly from delivery perspective. The first thing that we did was we chose a new PSA, a Professional Services Automation tool. We looked at all of them, because I’m a systems guy, my background, which we haven’t talked about that I actually went to school to be a developer. I loved softwares, kind of liked Bill Gates in that way, software kind of will take over the world.


But anyway, I looked and it came down to me to ConnectWise and Autotask, I know people who love both and I certainly would never speak badly of either one. We happened to be an Autotask shop, but it was really the key, it was a foundation of our desire to become a systems and a process focused company. And then we started to build everything on top of that, we layered on and we meant to do our automation from a patch management and monitoring and management perspective, and that was critical. So, we early on we worked with Hound Dog GFI Logic now SolarWinds and that was kind of our platform.


And then we recently have migrated to Autotask Endpoint Management, because we really believe in that single pane of glass, and then I feel like Autotask has a compelling story with the tight integration that they’ve made in the whole center stage platform. We did that, then and just to kind of ConnectBooster a little bit.  I was at Autotask Community Live, I forget how many years ago, and one of my buddies there, who’s also in Autotask PSA user and he’s like, “Hey man, have you heard about Connect User?” And I’m like,” No, what’s the ConnectBooster?”


I’m like, “No, what is ConnectBooster?” And he’s like, “Oh, let me show you.” So, he logged into his own ConnectBooster portal to show me the solution and the fact that it integrated with Autotask, and did integrate with Quickbooks. So, that now we can generate invoices out of Autotask, like it automatically go into Quickbooks. And oh, by the way, your customers have a place to log in and enter payments into their ACH information or credit cards. And from a billing automation perspective that was the final solution in the loop, the closing loop of working the time, billing the time, sending it to clients and then getting paid for it.


Dave Scott: That is awesome. How does the automation of those tools you talked about Autotask, some of the other automated tools, obviously ConnectBooster is one of those. How have they helped your business grow? What have they done for you all internally?


Jason Etheridge: The real magic, if you were behind many services, is to be able to disconnect the value that you provide to your clients, from the hours that a human is putting, what I call jokingly, putting fingers to keyboard. Essentially, you want to transform the value to the customer in up time, efficiency, productivity, ultimately profit for them, and how well you are automating what you do. Or how you do that, is in automating everything that you can use.


So, instead of having someone manually push the  button every time, you write a script to do that, you use RMM  to install software, you use ConnectBooster to automate people’s payments, you use your Autotask PSA or Connectwise to send out invoices, and to automatically put them in your billing or your Quickbooks software. Ultimately, automation, the elimination of repetitive or redundant tasks, helps you to be more efficient, which in turn helps you to be more profitable.


So, you’ll be able to take on more clients and add more revenue, without adding headcount and staff, and those staff that you do have, will be able to accomplish the value that you provide to your clients much more quickly and much more efficiently.


Dave Scott: I love it. That scalability is huge as you grow and it sounds like you’re figuring that out.


Jason Etheridge: At the end of the day, if you don’t do that, if you continue to  do things the manual way or what I call the brute force way, you will grow, and  you will succeed, and  you will have success, but it will be much slower, and you’ll only be climbing the rungs of the ladder one step at a time. And what I mean by that is, I climb up the rung, I get a new client, I hire another employee. So, then I have to climb the rung up, hire another employee, I get a few more clients, I hire another set of employees.


And so, you’re keeping the business going, but are you increasing the value at the bottom line? Or are you making talk about your enterprise valuation? Are you making your business more attractive? Or are you increasing their value inside your business, the owner’s value? Are you doing that or are you literally just taking money from clients and handing it to your employees. Money from clients, handing from your clients to your employees. If you’re doing that, that’s not increasing the value of your business.


Dave Scott: Plus it’s that much more stressful like, why would you want to put yourself through the ringer if you don’t have to everyday? You know what I mean?  I’ve always baffled my mind. And oftentimes on my own worst critic too. So I say that tongue in cheek, so, take that with a grain of salt. But man, it’s like beating your head against a concrete or a steel beam. It’s like, why would you continue to do that if you don’t have to? And that’s the value of creating something that’s scalable and flexible and that’s great.


Jason Etheridge: And let’s face it, it’s a lot easier to be  much smaller, if your net profits are going to say the same, or the value of your business is going to say the same, just be smaller. That’s a lot less stressful.


Dave Scott: It is, isn’t it? I was talking with a friend of mine recently, his company is exploding with growth and he’s like, “Dude, things are so stressful, my business partner and I are fighting all the time, and there’s three of them.” and he’s like, “I’m going to cut one off the business and the other one is just not cutting it.” And he’s like, “I wish I would not have grown to be this big.” They’re pushing like about 20, somewhere between 25 and $30 million in revenue, they have couple of hundred employees and he’s just taxed. He’s burnt out man.


And I was listening to him and he’s like, “I wish sometimes that I would have just stayed smaller, like I wish I would have been that soloprenuer, that unemployed digital nomad, so to speak, where I had myself in five or 10 employees and built a really nice nest egg.” A ‘lifestyle business’ and done it that way, because as you grow, as you know, it’s almost easier to stay small because of the challenges that come as you grow and it’s not just one, it’s like half a dozen that will hit you at the same time.


It’s hiring challenges, it’s funding challenges, it’s how you write off expenses challenges, it’s payroll issues. And do you do your payroll differently, it’s creating a benefit structure that hires good talent or not. It’s all those little things, it’s your marketing engine. The smaller you are, you can take referrals. You don’t have to necessarily be really awesome at sales and marketing, but as you grow, there’s more competition. And you can’t do that, you can’t do the same things that get you from 2 million to five million, to get you to $5 million to $10 million.


And to be honest, you can’t have the same people that took you from two to five, to five to 10, to 10 to 20 million. And that’s another thing my friend is struggling with, he’s primarily hired a lot of his friends and not his family, he’s kind of been against that, but he has hired a lot of really close friends and some of these guys are very junior level. If we were to grade them like you grade the public school, like A, B, C, or D, some of them are B, C, D players.


And they’re bringing the rest of the team down, and they don’t have the skill set, and the panache, and the moxie, to get their company above that hump, to get them from 10 to 15, or 10 to 12, and 12 to 15, and 15 to 18, and 18 to $1 million in revenue. And it’s a really tough slog. So, I completely understand what you’re saying when you mentioned the fact that it’s almost easier to stay small.


Jason Etheridge: I haven’t read it actually, but there’s this book, that somebody recently was telling about, the title of which explains exactly what we’re talking about. What got you here, won’t get you there.


Dave Scott: Amen to that. It’s true.


Jason Etheridge: That was a very kind of succinct way to play.


Dave Scott: Yeah. And that is really hard. You know, you’re the CEO, you’re the guy. It’s really hard when you have to stare in the mirror in the morning and think, “Gosh, I really might have to let this person go. Or I might really have to transition myself out of this role.”  And some of those decisions are extremely emotional, they’re extremely taxing, extremely stressful. But it’s like Marcus Lamone, has once told our CEO at IT Nation a couple of years ago, when he keynoted, he said, “Hey, I get all those things but that’s the bed that you made you need to sleep in it. And that is part of the territory in going along with it and if you don’t like it get out. And if you can slog through it, then it’s for you.” And those were truer words I don’t think were ever spoken.


Jason Etheridge: Yeah. For sure.


Dave Scott: So I wrote a blog piece a few years ago called The 31 Things I would Tell My Younger Self. It was one of the more therapeutic blog pieces I’ve ever written. If you could go back Jason, if you could talk to the younger Jason, what are some things that you tell yourself?


Jason Etheridge: Ob boy, we don’t have the time for that nor enough therapy dollars. But, I think the biggest thing that I would tell myself, starting out my business again, and again, I talk to a lot of people in the industry we either are just starting out or really want to grow or just want to commiserate with someone who’s been there. And essentially, kind of the two things that I focus on most often that I would tell myself or that if I could do differently I would, would be to be intentional sooner in my life because it took me a little while to figure that part out.


To decide ahead of time where I wanted to go and what I want to accomplish. The other thing would be to read the book The E-myth, revisit it sooner so that I could understand the value of systems and process even when it was just me. And when I read it, it was literally like, “How does he know? That’s us. That’s me. We have that problem.” And essentially, the solution, not to give away the punch line but the solution is you should treat your business even if you’re just one person like it’s a franchise, like it’s Ray Kroc to McDonald’s, and make the hamburgers the world around the exact same way.


And if you can internalize that vision of systematizing what you do, no matter what sized company you want to have, it will make getting here a lot, a lot faster and a lot less pain.


Dave Scott: Those are wise words that you tell your younger self. Well, Jason, what’s one thing that you’d do differently knowing what you know now?


Jason Etheridge: In typical fashion, I’m not going to be able to do just one, but I’ll you one or two. So the one thing I would do differently is I would use a PSA quicker. We thought for a while we could write our own help desk system and sell that. And so we were kind of suffering from what kind of company we want to be? Are we a software development shop or are we an IT shop or are we a helpdesk shop or whatever? Are we a product company?


I think I would have abandoned our custom built help desk solution, or never even gone there. I would’ve gone with an Autotask or a ConnectWise a lot more quickly. That, I think, would have made a big difference. And the other thing that we did that was super transformational is that we found a coach or a consultant in our industry who helped us remake our service delivery process.


And ultimately, that has been one of the most transformational things that we could have done was to … Because at the end of the day, it was like whoever wants to take the tickets that you want to take, build the relationships with these people. But, “Oh, if this ticket comes, I don’t want to take it.” We really hadn’t focused on the maturity of how we deliver our services. And if we could have done that sooner, I think we would probably be double the size that we’re at now.


Dave Scott: Yeah. And that’s part of the operating maturity model too. You have to understand some of those things sooner than later. I completely hear what you’re saying about getting a PSA sooner than later, I think that’s really great wisdom. Jason, what’s one thing if you’re talking to a young guy a young gal a young couple, whoever it might be. They’re just starting their journey as an IT business owner?


Lastly, what’s one thing that you would impart to them? What’s one piece, what’s one nugget of wisdom that you would share with them? Or one or two.


Jason Etheridge: Yeah. And honestly, I think this goes back to the other thing I would tell myself back at 26 is, the business will take as much time as you’ll give it. So if you give it 80 hours a week, it will take 80 hours a week. If you’re going 100 hours a week, it’ll take that. If you give it 60 or whatever. So you need decide up front when you’re starting your business that you’ll set some guardrails for yourself around how much time you’re willing to give your business. Not that there’s not a season in life that you put in 80 or that you put in 70 or whatever.


But set some guardrails so that you don’t lose that connection to the outside world, so that you don’t abandon your wife, if you’re already married when you start your business or that you don’t not see your children grow up if you have small children when you start your business. Or like I was, when you’re single, that you don’t delay getting married because you don’t spend time dating because you’re focused on growing your business.


All those things are … Starting your business, growing your business. Those things are great and they need to happen. You’ll need to split and sweat equity, but you need to set some guardrails so that you don’t get a season of your life pass you by and then you look at one day and you wonder, “Where did all the people go?”


Dave Scott: Yeah. That is fantastic wisdom and knowledge. There’s a couple of friends of mine that have passed away suddenly of cancer in the last year and it’s been really emotional for me, it’s been really hard, it’s been extremely eye opening. And one of the things I’ve heard time and time and time again is, “I regret not doing this. I regret not spending time with this.” You can make more money, you can buy more cars, you can meet more people, you can network more, you can always watch goofy cat videos and Tony Robbins videos on Facebook till the day is long, but you’ll never get more time.


So, go ahead and start, go ahead and do what you want to do. Go ahead and start that dream, go ahead and take that step, and realize that it’s often not as hard as we think it will be, versus what our mind portrays it to be, if that makes sense. So that’s great wisdom. And to your point, if you don’t do that, you’ll look back at 80 years old on your deathbed and go, “Dang, I really wish I would have done this differently”


Jason Etheridge: Absolutely.


Dave Scott: Jason, lastly, where can people find you?


Jason Etheridge: Yes, so my website is, and that is And you can reach me at Twitter @Jason_Etheridge, E-T-H-E-R-I-D-G-E. And I would love to interact with you guys. Certainly, shoot me a tweet or a direct message, and if there is anything that I can help with, I … The other thing we didn’t talk about is, I’ve done some consulting with other small businesses to, like I said, to kind of help them to move further faster. And if there’s anything I’ve learned along the way, I love trying to help small businesses not to make the same mistakes or make different ones, or maybe learn from some of the things that I’ve done.


If there’s ever an opportunity where I can do that, I’lI love to invest back into other small businesses to try and help them to do some things well.


Sponsor Message: Before we end today’s episode, we’d like to thank our sponsors, 5 Step Marketing and BVoIP. Don’t forget to take advantage of your free one hour marketing strategy session with Josh and his team. That link, again, is That’s the number 5, And check out BVoIP if you’re looking to improve your telecom strategy. You can find BVoIP online at


Dave Scott: Jason this has been wonderful, man. I really appreciate it. I appreciate your time and thanks for coming on the podcast.


Jason Etheridge: Thanks for having me. It’s always good to catch up with you.


Dave Scott: And thanks everyone again, for joining us today on the Confessions of an IT Business Owner podcast, where we believe that healthy cash flow is critical to your business, automation is paramount, and building trust with your clients by looking more professional is ultimately going to help you grow your IT business. To learn a little bit more about our podcast and listen in and download all of our recent shows, visit us online at That’s


And to learn a little bit more about Jason’s business, like he has said, visit him at and feel free to follow him on Twitter. Thanks again everyone for joining us on today’s show. We’ll talk to you soon.

Episode 6 – Confessions of an IT Business Owner – ft: Chris Schalleur

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Welcome to the Confessions of an IT Business Owner podcast. In this episode, you’ll learn about some profound struggles related to owning and growing an IT business from the perspective of Chris Schalleur, CEO of Christo IT Services.

This episode is sponsored by and Check out Josh Whitford and his offering at, and learn more about the perfect channel only offering for your IT firm and MSP business at

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Dave Scott: Hey, everyone. Welcome to the Confessions of an IT Business Owner podcast, where we believe that healthy cash flow is critical for your IT business, automation is paramount, and building trust with your clients by looking more professional will help you grow your business. I’m your host, Dave Scott, and today we’re going to talk with Christo IT CEO Chris Schalleur about a lot of the things that he went through in terms of growing and starting his IT business.


Chris Schalleur: If you’re chasing money 60, 90 days down the road, you’re kidding yourself. You just can’t operate like that, at least not sustained, because if you stub your toe, you’re done.


Dave Scott: Here’s the podcast with Chris.


Chris Schalleur, sir, thanks for joining me. I really appreciate you taking the time today.


Chris Schalleur: Awesome. Thanks for having me, Dave.


Dave Scott: So Chris, we obviously know your name, since I just announced it to the world, but tell me the name of your company and where you’re all from. Give me kind of your baseball card stats.


Chris Schalleur: Oh, sure. By day, we’re Christo IT Services. We’re a 15 person MSP just north of Philadelphia, about a half hour north of city hall. We’ve been part of the community since 1999. We started really focusing on managed services and all of that fun stuff in 2005.


Dave Scott: That’s awesome. Are you typical Eagles fans, being that you’re from that area?


Chris Schalleur: Yes. Yeah, it’s definitely Philadelphia pride in the office here. I’m probably a fish out of water. I’m actually a Dallas fan located in the Philadelphia area. Most of my staff has begrudgingly allowed me that while still rooting for the Philadelphia Eagles every once in a while.


Dave Scott: Nice, nice. You love the team that America loves to hate.


Chris Schalleur: Yes.


Dave Scott: And your staff loves the team that you can thank us for your first round draft pick for, named Mr. Carson Wentz.


Chris Schalleur: Yes. Yes, absolutely. North Dakota, absolutely. He’s been a very … He’s been a new life blood in the Philly Eagles, yeah.


Dave Scott: Yeah. Brady, our CEO, and I talk almost daily about how the Vikings should have drafted him. That’ll be one we’re kicking ourselves probably for the next two decades on. So, Chris, we know a little bit about what you do and where you’re from. What was the passion behind starting your IT company?


Chris Schalleur: I was always a computer guy. I always played around with computers. I was always the go-to guy growing up and in my first couple of jobs in chemical engineering and marketing and stuff like that. Eventually got to a point where I started doing moonlighting, and then started a business. I like to talk about people coming to work for me as one of my biggest honors. They put their faith in me and in the business and our passion for things. It’s always such a big honor to have somebody come and put their livelihood and trust in us. I always tell people one of the first gut checks, about two or three years into the business, was hiring that first person. I still consider that one of the biggest leaps of faith that I had.


Dave Scott: Yeah, I love that. I think it sounds like, and just from knowing you a little bit outside of the four walls inside of ConnectBooster, you guys really pride yourself on that culture, right? That’s one thing I’ve always admired about you.


Chris Schalleur: Yeah, we have some really long-tenured guys that have worked for me for 12, 13 years, all the way through a couple new guys on the team. But our average tenure is probably five or six years with the team.


Dave Scott: That’s awesome. That’s awesome. Let’s transition a little bit. I want to know a little bit more about the day you left your old nine to five job for the opportunity of being self-employed. What was that like?


Chris Schalleur: Well, it started with a pink slip, which is always a great start to any story.


Dave Scott: Right?


Chris Schalleur: I was one of those huge startups that went from 50 person company to a 300 person company and then a year later they were back down at a 50 person company again. I had been moonlighting, so I had already … We just went for it. Funny enough, I think it was almost 60 days later we found out we were pregnant with our first one.


Dave Scott: Oh man.


Chris Schalleur: It was always just a gut check there, which happens throughout the course of anybody’s [inaudible 00:04:56] participation in this journey.


Dave Scott: Yeah. That is stressful. Holy cow. So you were moonlighting, you got the pink slip, but let’s back up a little bit before that. When did you first have the notion that you wanted to be self-employed?


Chris Schalleur: I’m the son of an entrepreneur.


Dave Scott: Okay.


Chris Schalleur: So it was kind of cooked into me, because my father was working out of a fourth bedroom up in the upstairs and having clients visit and phone calls and things of that nature. He was staring an accounting practice up. So I can remember just being raised in that house of this is important. My mom worked for my dad at the time, as well, so I was kind of incubated into that entrepreneur mindset from a very early age.


Dave Scott: Yeah, that’s awesome. So what was your perception, as a little kid, watching your parents live through that and go through that professionally? Because for my kids … I have two daughters, and they’ve seen me do both. I’ve worked for large Fortune 500 companies where I punched in, punched out, eight to five, Monday through Friday. I was simply a number in the HR department, and I had an employee number and a badge and everything like that. They’ve also seen me struggle and work 60, 70, 80, 90, 100 hours a week some years, so it’s been crazy for them. One of my daughter’s perceptions is, “Hey, this is really cool, Dad. I’m glad you’re doing it.” The other one’s like, “Hey, this sucks. This is hard. I don’t want to do this and I begrudge you a little bit because you did this.” So what was your perception, growing up in that environment? What was that like?


Chris Schalleur: I don’t remember having any aha moments. Maybe when I got into my early teens, you get into middle school or high school. But as a younger kid, it was just the way things were. Dad works 80 hours a week. I remember getting in trouble once when I was a little kid when I said Dad was a workaholic. I didn’t know what the term meant. I just thought it was … Somebody said something on TV and I said … I was over at a friends house and that got back around to Mom real quick, of course, and, “What do you mean by that?” I was like, “I don’t know, I just thought it was funny.” “You don’t say that.” “Okay, well.” But it was just kind of how our house was. I mean, this was … You work really hard. We always had great times together and everything like that, but it was …


There was no aha moment probably until high school, when I think what started to click for me was … I was a swimmer and had swim meets and stuff like that, and my dad as always there. So part of what clicked for me was having that flexibility as an entrepreneur, as a business owner. He was working so that he had that flexibility to show up for a swim meet in the afternoon. That kind of clicked for me as what I want to do for my kids.


Dave Scott: Yeah. I think, for a lot of self-employed people that move into the season of entrepreneurship, because there is a difference. There’s a Carol Roth book … She’s a businesswoman and an author. She wrote the book The Entrepreneurial Equation, and she talks about the difference between somebody being self-employed and having one or two employees versus somebody who’s an entrepreneur. But I think the freedom that either one of those categories, either one, a person who’s either self-employed or entrepreneurial fits in. I think the freedom that you get, that being that digital nomad, so to speak, or unemployable, as I like to call it. I think there’s a lot of value in that, in not being tied down. Yes, you have to work. Some weeks it’s 40, 30, 40, 50, 60 hours. Under 40 or 50 probably doesn’t happen, truthfully speaking.


Chris Schalleur: Sure, sure, sure.


Dave Scott: But I think anything over 70, 80, 90 hours a week is probably the norm. But there’s a lot of value that comes with that, right?


Chris Schalleur: There is, as long as you’re not lying to yourself, Dave. I mean, you’re going to go through spurts, especially as the business hits certain tiers, as you get out of that hundred, $200,000 tier and you get into the three or four employee tier. Then you get into half a dozen tier. You’re going to hit those tiers where you’re going to have to put a sustained time of, “I don’t see any daylight ahead of me.” You’re going to hit those black periods, but as long as you keep true to yourself and that, “I’m going to get through this, and this is why I’m doing this,” and you’re not lying to yourself that, “Well, the next level is just [inaudible 00:10:04] the next level,” you’re going to be okay.


Dave Scott: What gets you through all that? Talk to me a little bit more about that, like what gets you through those seasons or those periods?


Chris Schalleur: For a couple of those periods I had the blessing of having my wife work with me. A lot of people kind of go, “Oh my god, how was that?” I was like, “Well, it had its bad days and its good days.” Because you’re with each other all the time, but at the same time, when you get home at night, you know how the day was already. If it was a bad day, you both had it, so it was experiencing that together. So there was a lot of positives that came out of that. Since then, my wife’s gone back to quote-unquote her “real job” or her real career, but it is working with my team in the office that … Hey, this is what we’re working on now. That gets you through those solidarity pieces. Then coming home and obviously getting a hug and kiss from the wife and the kids is obviously going to get you through just about any bad period in your time.


Dave Scott: Yeah, no doubt, yeah. Yeah, amen to that. Truer words have never been spoken. Tell me the story of what draws you back into your office every day. You put your feet on the floor and realize, hey, this is a new day. What draws you back to it every day?


Chris Schalleur: Over the past year or two we’ve been working on new cloud solutions and new ways of talking to clients about technology. Since we’re obviously in this industry that’s constantly changing, having that something new to talk about with people. Or, everybody’s seen the headlines recently with cyber security, and having that ongoing conversation of like, “This is constantly evolving and I have something to tell you about. I have something to talk to you about.” That’s really kind of what really gets my jets firing.


Dave Scott: That innovation piece, that creativity piece, it sounds like, is really important to you.


Chris Schalleur: Yes, absolutely.


Dave Scott: Yeah. Looking back on everything over the last, what, 14, 15 years of business, you got to put your feet up on the desk every once in a while and go, “Man, it feels good to be here at this point that we are today.”


Chris Schalleur: Every once in a while. I’m a little bit of a blushing boss on that kind of stuff. I get thank yous from clients and I get thank yous from staff and stuff like that. I appreciate it, it’s always appreciated, but if we’re not constantly having that conversation, having that, “Here’s what value I can bring to the table,” it’s going to be short-lived. I kind of always have that whisper in the back of my mind of, “We got to be bringing something new, otherwise we’re yesterday’s news.”


Dave Scott: Yeah, no, I hear you. I think I’ve never met an entrepreneur that likes self pats on the back. It’s just not in their DNA. To your point, if you’re not sleeping, you’re working. If you’re not working to think about something innovative to bring additional value, there’s something missing. So I hear what you’re saying on that.


Chris Schalleur: Yep.


Dave Scott: I know firsthand how hard and tough it can be owning and running a business. Talk to me about some of the struggles in owning your managed service practice. You talked a little bit about the struggles of maybe working with a spouse, or in your case it sounds like it was a blessing, the struggles of hiring good people, and things of that nature. So talk to me about one or two things that’s hard about running and owning a managed service business.


Chris Schalleur: Part of it is what we were just talking about, keeping up with everything new, because it is so constantly changing. One of our biggest struggles, in the beginning, was to come up with our quote-unquote “stack”. This is what we’re going to bring to the table. Because it’s so easy to get distracted, and we didn’t have a value internally for what consistency meant to us as an organization. What I mean by that is, well, we had these eight different solutions, as opposed to, here’s the value in just having these two solutions and here’s the value in just having this one solution. That was really one of the biggest struggles, is bringing all of that together. It took literally years to finally consolidate all of that and have one solution stack that we’re going to be able to provide to our customers, and it was absolutely invaluable.


Something else that we really kind of worked on. We had a number of acquisitions through the years, and that didn’t help on the consistency, because when you acquire things you don’t really have the luxury of bringing in exactly everything as you have it now and as you would want it. I’ve talked numerous times in numerous pieces about all the different acquisitions that we had, and all the pains that go along with assimilating those clients as well as assimilating the staff that comes along with them. It was really a growing point for both my business partner and myself as far as who we were as leaders and what we wanted to become.


Kind of the most recent struggle for us was we finally had a sit down with ourselves and said, “Look, we can’t continue to grow the way we’re growing and still be able to provide service to time and materials clients.” We had a number of clients that had been with us since the very, very beginning, and we finally just had to have personal sit downs with them and say, “Look, we’re not going to be the … I know you put your trust in us over the years and when we were little guys, and you helped us grow, but unfortunately, we’re moving on from this and we’re going to need to move on from you as a relationship, as a vendor.”


Dave Scott: Interesting. So it sounds like you guys have gone through a handful of M&A deals, or merger and acquisitions, where you’ve had some struggles not only from a resource perspective but, like you talked about, the post-merger and acquisition tasks. Like how do you assimilate people from their culture to your culture? Do you keep some of the team members? Do you not? What’s the revenue stack looks like? Do you offer more product offerings? You touched on that a little bit. So talk to us a little bit more about that, like what was your overall opinion of M&A? Is that something that you have a bit of a sour taste in your mouth about, or is it something that you’d recommend to other peers?


Chris Schalleur: Oh, so many lessons learned on that one, Dave.


Dave Scott: We’ve got time, so go ahead and regurgitate everything.


Chris Schalleur: Here’s the first one, and this actually relates to your world. One of the biggest lessons learned was have a very blunt conversation about invoicing, and how companies say, “Well, we invoice on the first of the month and everybody pays on the 30th of the month,” is a very different conversation from everybody pays before the first of the month. Very quickly with one of our acquisitions in 2009, we quickly ran aground almost in the first 30 days because the cash flow wasn’t there on day one on the M&A. That was horrific, to the point of where was that $100,000 that we were expecting? Well, we’re not going to get that for 30, 45, 60 days from now. That was quite a gut check there.


Second lesson learned that I had was really that the acquiring company really needs to be using some sort of system, a PSA of some sort, because having Excel and Calendars as a mechanism for delivering their IT services is … You can’t know what value you’re getting if the company’s not using a system.


Dave Scott: Right, yeah. Did you acquire somebody who wasn’t using a PSA at all?


Chris Schalleur: Yeah, actually, two of our biggest were Excel and Calendars. They had hit the point of four or five employees and were hitting those points that I’m sure a lot of the listeners have had where you reach that point and the wheels start coming off. You can’t manage beyond that point. So they were on the point of making the decision on investing in some sort of system, and instead decided to get out of the business.


Dave Scott: Wow, interesting. So invoicing was a huge issue post-M&A because cash flow wasn’t available, based on maybe the financial due diligence, and the acquiring companies didn’t really have a good process, or a software tool, I should say, for delivery, right?


Chris Schalleur: Yes. Those were absolutely huge for us. That cash flow was a very, very tough lesson.


Dave Scott: Yeah. Being shorted a hundred grand or whatever that dollar amount is, is not … That’s not a stressless situation, right?


Chris Schalleur: No, that’s a big oops.


Dave Scott: Yeah, right, exactly. Did you guys go through an M&A advisory firm, an M&A firm? Or did you use an attorney or a broker? How did you go through that process?


Chris Schalleur: When we first looked at M&As … We’ve done six of them throughout the course of our company lifetime, going on 20 years now.


Dave Scott: Okay.


Chris Schalleur: Most of them have been small, one, two, three person shops. They were all done with an accountant and maybe a couple hours with a lawyer just writing something up, and it was a pretty cut and dry kind of thing.


Dave Scott: What was the post-acquisition like? Was there a plan, or was it just, “Hey, here’s the keys to the new operation with all these new employees,” violent shove in the small of your back down a steep hill, and away you go with lots of bumps and bruises along the way? Or was there a post-acquisition strategy that you all had in place by working with an M&A team?


Chris Schalleur: The plan was always to have sit downs with each of the clients, sit downs with each of the new employees. Eight times out of 10 that worked.


Dave Scott: Okay.


Chris Schalleur: Sometimes the wheels came off just from a … The clients that you’re acquiring have businesses and timetables and things that are going on. Your interruption of that has very little validity to do with their day. Most of the time it worked okay. Our biggest lessons learned was that we didn’t get granular enough with the acquiring value companies.


Dave Scott: Ah, got it.


Chris Schalleur: When you’re our size … I mean, once you get up into the millions upon millions of dollars, that’s a different story, but typically in our MSP world you’re dealing with a couple million dollars and less companies. This is my biggest lessons learned in 20/20 hindsight, is there’s absolutely no reason why during the due diligence process and evaluation process, you can’t go line item by line item, company by company, and assign a value to each of those companies and what they are in terms of value that you’re going to be paying for, what the expectations are. You can assign a different plan to each one of those companies, based on what their needs are, based on what the history is, upcoming projects, what the owner of the business that is that client. You can get that granular. There’s no reason why you can’t.


It is going to take a little bit more time, but it’s absolutely … If you lay that out during the evaluation and the due diligence process, you will come back in spades as far as being very, very clear with both who you’re buying, the owner of the company that you’re buying, as well as yourself and not peanut buttering the value over however many companies that you’re buying.


Dave Scott: Yeah, no, and I think you hit the nail on the head when you talked about doing and going through the due diligence process. What I hear often in M&A world is people that go cheap regret it. Don’t go cheap. Spend the proper amount of money and time to do it right, up front. Go through that really fine … Take a fine toothed comb to the due diligence process to make sure that everything is set.


Chris Schalleur: Yeah. Us being entrepreneurs, we have a tendency to kind of gloss over those details.


Dave Scott: Right.


Chris Schalleur: What you want to do is you want to bring those detail people to the table with you, those lawyers that are going to go over every single line item, because we have a tendency not to.


Dave Scott: Right.


Chris Schalleur: We have a tendency to rely more on gut check and looking in the eyes of somebody and handshake and really what your feeling is. When you go to that table, this is not the place for that. You want those accounting lawyer people by your side that are going to be those detail people.


Dave Scott: Yeah, no, I think that’s really good wisdom.


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And now, back to the show.


Dave Scott: Let’s talk about the value of automation inside of your business. I think we all can agree that it’s critical to the health and success of any IT company. Talk to me a little bit about what processes and systems that you’re automating today.


Chris Schalleur: A lot of what we automate now really comes from our ConnectWise PSA system. It pretty much runs our entire business. It runs everything from the ticketing to the invoice. A lot of people in the MSP world are familiar with it, but we’ve really automated a lot of that to take away the need for more overhead in our business. We are really kind of expense conscious in our MSP, so wherever we can avoid having a person do something, even if it only gets us 80% of the way there with automation, we’re going to automate it rather than having somebody sit there and do the busywork, for lack of a better term. We really, really abhor throwing a warm body at something. We’re really going to automate the hell out of it, instead.


Dave Scott: You talked about PSA. What sort of things are you all automating through your PSA? Are you automating everything from delivery to support tickets to quoting? As you know, we use ConnectWise here at ConnectBooster, and we love it. We use it for quoting, our sales guys and our marketing team uses it for quoting purposes. What are some of the other things specifically that you’re all automating through that?


Chris Schalleur: We board, B-O-A-R-D … We board the hell out of just about anything that we can compartmentalize in the business. We automate everything from the quoting process … We actually use the ticket system for our sales pipeline. We use activities and stuff like that, and my salesperson does all of that. But once we get an appointment, once we have somebody who wants to sit down and meet with us and we’re actually going to spend some time with, that moves into a ticket. We start automating that process all the way through a qualification state, through a tech assessment, automatically attaching those checklists and due diligence processes during that courting phase and vetting phase for a new prospect, all the way through to the quoting phase and getting that proposal in front of the prospect and getting them to sign.


Dave Scott: That’s the beauty of automation. You talked a little bit about the why that you’ve done it. What do you feel like the improvements have been by automating a lot of these what I would call manual tasks or manual time sucks?


Chris Schalleur: In most small businesses, you typically have some sort of champion of XYZ, whatever it happens to be. This person knows how to do this, or this person knows how to do this. One of the really big benefits that we’ve seen out of the automation of it is that it doesn’t … If that person goes on vacation, or they’re just not in that day, that excellence that they have, those little nuances, can be part of that automation, and it can be done the same way, the same excellent way, by any member of the organization.


Dave Scott: Yeah, and I think that efficiency speaks for itself, doesn’t it?


Chris Schalleur: Yes. You can’t put a price tag on that, because once it becomes part of your culture and that, it’s just how things are done. The expectation level just rises, and that’s your new baseline. So new people coming into our company, new employees, even new customers, you get that wow factor.


Dave Scott: Yeah.


Chris Schalleur: You can’t put a price tag on that. Well, on day one I had this, this, this, and this. It just happens no matter what. If somebody’s out sick, if somebody’s on vacation, like I said, it still happens. As much as they’re awesome, you don’t have to rely on human beings. You can rely more on your processes and allow the team to get things done instead of an individual.


Dave Scott: Yeah, no, and I love that. I think, too, and I have this conversation a lot with Matt Bitzegaio … He’s our chief technology officer here at ConnectBooster. We often talk about the value of either being small or embracing the chaos that’s going to come with growing as a business. One of the things that it’s easy to do is stay small so that you don’t have to automate and you don’t have to do a lot of these things so that you can scale and grow your business, because scalability is key as you grow. If you’re not, that’s a huge roadblock. But as you grow to your point, you can’t rely on awesome human beings to do a lot of the things that you did at 2 million or $5 million. Once you get to 7, 8, 9, 10 million and 15 million, 20 million in annual revenue, you really have to take a focus and take a step back and remove people from certain functions so that these things can be automated, so that you can grow and scale without people jumping off the rooftops. You know what I mean?


Chris Schalleur: Yeah, yeah. One of those ones is in your world. I mean, accounts receivable is … You could pay somebody to sit there and poke people all day long. Why? Why not automate that? Why not have something that pokes people automatically? I mean, I’m sure most PSAs do, but ConnectWise has an awesome university article of set up an accounts receivable board, set up automated statuses, and just let it run.


Dave Scott: Yeah.


Chris Schalleur: You might cringe at that, and I get that. When I first heard this, I had that cringe factor of, “Well, it might rub people the wrong way.” Nope, get past that.


Dave Scott: Really? That’s not truth? That’s not fact?


Chris Schalleur: When I first heard this, “Well, you got to treat your clients with kid gloves. Don’t ask them too often to get paid,” and everything like this, and always had that cringe moment with people. You got to get past that. You got to get past your own head trash of you provided services or you’re going to provide services, that they need to pay. Automating that is no way going to offend anybody. It just isn’t. You’re providing a business transaction and, “Oh, by the way, here’s your invoice.” A couple days later, “Oh, by the way, I haven’t heard anything from you, here’s your invoice.” I mean, there’s no reason why you can’t poke people like that.


Dave Scott: Right. I love it. I think sometimes we like to make things harder and like to think that they’re harder than they actually are.


Chris Schalleur: Yeah. Unfortunately, I’m probably … I don’t take offense when I get a notice in the mail. Why would any of my clients?


Dave Scott: Right. Me neither. I actually think it’s a point of pride, because it tells me that they’re focused on their customers and their followup is good. If I didn’t ever hear from somebody and I just got a random invoice like six months …


Well, here’s a story. About 10 years ago my wife and I were selling our home. We got into a bit of legal trouble, not anything on our end, so I hired an attorney. Everything worked out fine in the end. Everything was hunky-dory, albeit during my vacation, which was awesome, right? My week and a half long vacation, I’m having to deal with attorney phone calls and going back and forth. But all that to be said, everything worked out just fine in the end. But, literally seven months later, I get a bill, and we didn’t get a bill from our attorney. It wasn’t a lot. It was like a couple thousand bucks or whatever. And I’m like, “This guy has really crappy followup.” He is a bulldog of an attorney and I’m grateful that I worked with him and he’s awesome, but he is not that talented and that smart to be above good customer service.


As a consumer, as a customer that … and as somebody in marketing like I’ve been for a long time, I really pride myself, and I try to filter things through the lenses of good customer care and good customer service. When that doesn’t happen because people don’t pay attention to meticulous details through good billing or good invoicing, it just kind of shows up as a blight.


Chris Schalleur: It does, and I think that’s probably one of the biggest struggles in our little IT community, is that 99% of us have come out of the technical end of things. Providing that service, saying thank you to somebody, shaking their hands, fixing their problem, making their day better, and then leaving wherever it happens to be, either remotely or in person. Then exactly kind of the story that you … All of the other stuff happens. The invoicing, staying up at night trying to generate your time sheets and trying to do this and that and the other thing, and it isn’t done as well because less importance is placed on it. Because most of us came out of the tech field and that’s where the priority lays, is fixing the problems, not necessarily putting on the best face on your invoicing process or your accounts receivable process, because it’s typically an afterthought, for lack of a better term. But it really does … It’s as much as your presentation as how quick your service is and how good your service is.


Dave Scott: Yeah, I completely agree. I wrote a blog piece a few years ago. It was pretty therapeutic. It was called The 31 Things I Would Tell My Younger Self. If you could go back in time and you could talk to your younger self, after seeing what you’ve accomplished today and a lot of the victories and even defeats that you’ve had, what would you say? What sort of wisdom would you impart on a younger Chris?


Chris Schalleur: Wow. Stay away from the fried foods. No. Probably the biggest thing would be similar to what I had spoken about earlier. Get out of your own way. Stick with what you’re good at. As much as it pains everybody to part with that money, hire somebody to do that job, either a 1099 or an employee. Because they can, regardless of what you think, they can do it better than you. Because your part-time brain is just never going to be as good as somebody whose sole focus is to do that.


Dave Scott: That’s good wisdom. Knowing what you know today, would you do anything differently? I know you talked a little bit about M&A. Would you maybe not go through an M&A deal without doing one thing, or would you and to hire this sort of person? Or would you hire this sort of person, or would you do one thing differently? What’s one or two things that, knowing what you know today, that you’d do differently?


Chris Schalleur: I would get more into the process earlier. We relied a little bit too much on that individual excellence that I talked about earlier, where we put it down on paper as to why are they excellent? When they do blah blah blah for you, why are they excellent? Actually writing down all the little nuances of what they do and how they care. You have this fantasy, or I did at least, of, “Well, that’s some of the magic of what Christo IT is about. We have these wonderful people and they do this wonderful job,” and somehow, by writing it down, we were somehow going to kill the magic. I don’t know if I consciously or subconsciously thought this, but getting more into that process earlier would’ve absolutely been … If I could go back and whisper in my own ear, just write it down.


Dave Scott: I love it. Lastly, what’s the number one point or message that you could drive home to any of your peers listening to this podcast today? Imagine somebody in your shoes, maybe they’re just starting out or they’re in the middle of a interesting season. What’s the one point or message that you would want them to hear?


Chris Schalleur: I would actually have two. One, cash flow is everything, which is an easy one. It translates all businesses, but if you’re chasing money 60, 90 days down the road, you’re kidding yourself. You just can’t operate like that, at least not sustained, because if you stub your toe, you’re done. You’re going to have a major problem. So cash flow is absolutely everything.


The second thing I probably would highlight for everybody is to get granular within yourself. What I mean by that is, you can go line item by line item, you can go client by client, and get really, really specific about not only making sure that you’re providing the best service to them and going, “What do they need? What is their road map? How can I provide better consulting services to that client?” As well as granularity on your inside, for yourself. Are they a profitable client? Is there anything that we can do to get more efficiency out of that one client? We can talk about generalizations and things that overlap and umbrella the entire company, but it’s very rare that we have, once we reach a certain size, that we’re not going to that line item by line item detail and paying attention to those fine things. Because even if you squeeze just a little bit out of each one of those line items, it’s going to make a huge impact on the bottom line for yourself.


Dave Scott: I like it. Chris, where can people find out more about you and your business?


Chris Schalleur: I’m kind of a Facebook junkie, so I’m all over Facebook. We have our cartoon characters there, so we talk about our unique selling proposition there and our different cartoon characters and what makes Christo IT different. That’s a great way to find out more about them, and on LinkedIn. If you could look up Chris Schalleur or Christo IT services, I’m usually on LinkedIn as well.


Sponsor Message: Before we end today’s episode, we’d like to thank our sponsors, 5 Step Marketing and BVoIP. Don’t forget to take advantage of your free one hour marketing strategy session with Josh and his team. That link, again, is That’s the number 5, And check out BVoIP if you’re looking to improve your telecom strategy. You can find BVoIP online at


Dave Scott: Chris, hey man, I can’t tell you how much I appreciate you as a person, as a friend, and as a partner, so thank you so much for being on this podcast today.


Chris Schalleur: Awesome, awesome, awesome. Thank you for having me, and always great to talk to you, Dave.


Dave Scott: All right. Thanks Chris, we’ll talk to you soon, buddy.


Chris Schalleur: Bye bye.


Dave Scott: Thanks again, everyone, for joining us on the Confessions of an IT Business Owner podcast. Thanks again to Chris Schalleur, the CEO of Christo IT Services. If you want to learn more about the podcast, download the show and even the transcript, and if you want to take a look at the case study that we actually published about Chris and his company and the automation tools that he uses to grow his business, you can check all that out at Thanks again, everyone, for being on the show and joining you us today. We’ll talk to you soon.


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