Confessions of an IT Business Owner:
The ConnectBooster Podcast

Subscribe to the ConnectBooster Podcast

  • This field is for validation purposes and should be left unchanged.


Tune in to hear inspirational, honest stories about what it takes for a tech business to survive and thrive, from some of your favorite leaders in IT.

Brought to you by ConnectBooster’s President and Co-Founder, Ryan Goodman.

Listen Now!

Tim Conkle – Roland Technology Group & The20

Apr 22, 2018

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 Tim Conkle, CEO of Roland Technology Group & The20. 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
Ryan Goodman: 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 in building trust with your clients by looking professional will help grow your business. I’m your host Ran Goodman and today you’ll learn about some profound struggles related to owning and growing an IT business and how Tim Conkle from Roland Technology Group and The 20, overcame them.  
Tim Conkle: Vision without execution is a dream. You can dream big. You can have a vision of what you want to be, and the problem is, is a small, small company execution is a nightmare.  
Ryan Goodman: Here’s the podcast with Tim. Well Tim, thanks for joining us on the call today, appreciate you spending a little bit of time with us here at Connect Booster and Confessions of an IT Business Owner.  
Tim Conkle: Uh-oh.  
Ryan Goodman: You didn’t know it was going to be this deep, did you?  
Tim Conkle: I didn’t, but this’ll be more like therapy.  
Ryan Goodman: We’ll probably both do each other some good, how about that?  
Tim Conkle: Absolutely.  
Ryan Goodman: Beautiful. Well why don’t we get a couple of the basics out of the way? Tell us your business names, because you are an entrepreneur’s entrepreneur and own multiple businesses, and also where people can find you online.  
Tim Conkle: Start at the beginning, Roland Technology Group was my natural MSP based in Dallas. Then from there, we built out a, just from pure need, a VoIP company, and that VoIP company is Cytracom and you can find it at And then from there, the next iteration with us was obviously The20, you can find it at That is a aggregation of lots of MSPs moving in the same direction, ultimately if you look at it that way.  
Ryan Goodman: Sure. So talk to us a little bit about how you got started in technology and that started with Roland Technology Group, is that correct?  
Tim Conkle: It did, it did. In fact, me being in technology probably was the least likely thing to happen in life for me. Because when I was in high school you had a pager, never touched a computer, went in the military and by some osmosis of being in the infantry, I get stacked into a room where I’m working on a computer. I literally fell in love with computers in the military.  
From there got out, obviously went to college for the programming side and got a bachelor’s degree in that and then thought that I would write code forever. In actuality, I never wrote any code whatsoever, outside of college I never wrote a single line. I went down the route of infrastructure, worked for a company called EDS. Most people will know that because Ross Pero owned it and ended up selling that company to General Motors for 3 billion bucks. So I worked there but I had the technology bug, so in 1992 I literally bought a company that was founded in 1986, which was an IT company.  
Back then everybody built white boxes and had a storefront and all the other things that went with it. But I was much more business-minded just from my background. So I took that IT company, which was really a residential IT company, fixing computers for every day people. I took it completely towards the B2B space and eventually completely out of the residential, or anything that would even have an [inaudible 00:03:54] component to it, if you want to know the honest truth.  
Ryan Goodman: So the exposure to computers and technology was in the military. What about the passion behind becoming an entrepreneur and starting the business and deciding that I’m going to buy this business in 1992. What was the drive behind that? What was the reason behind that?  
Tim Conkle: So if you look at my family itself, all of my uncles own their own business. My dad owned his own business. All of my brothers own their own businesses. It’s literally in our blood. My dad, my mother has 11 brothers and sisters, eight of them which are boys, all but one literally have a business that my dad started and gave to them. So my dad was notorious for teaching us how to fish, in other words, creating entrepreneurs.  
Ryan Goodman: Right.  
Tim Conkle: So it’s literally in our blood, I think.  
Ryan Goodman: That’s incredible. What an environment to grow up in. This is a side question, but what were some of the dinners conversations that you guys had? One of the fears in my life is, how do I teach my kids to have a great work ethic while growing up in an entrepreneurial household and having more than I had. What were some of the things that your dad did to make sure you guys knew how to work your rear ends off?  
Tim Conkle: It’s kind of crazy, I boil everything down, that I am, how I think, how I do business to three real stories with my dad. One is, every morning at breakfast we would all, we all ate breakfast together, all my brothers and sisters, which I had seven brothers and sisters. Every morning, my dad went through a ritual of talking about, “We’re Conkles. We can do anything we want. You’re the smartest kids in the world and the only thing that will ever keep you from being everything that you ever imagined in your mind to be is not executing on your dream.” This was a story that got told almost every single morning.  
The other thing he did was he taught us to dream with our eyes open every morning. Typically when we ate, he would tell stories, grandiose stories of things that were much bigger than we were. But he always told us these things when we were awake, alive and well, which meant he taught us to dream with our eyes open. He’d always say, “Dreaming at night when you’re asleep is okay, but it really never brings anything to reality. Learn to dream with your eyes open. Dream bigger than you are and you’ll always be more than you ever thought you could be.” So that was the second thing. There’s long stories to go with that.  
The third was, a story about a motorcycle which I tell all the time at different conferences and things. That story is the foundation principle for every successful thing I’ve ever done in anything I’ve ever done. If it’s followed, all 20 members that come in, hear that story. It’s the first story they hear from me when they come visit my office in Dallas, because it guarantees anyone that applies three basic principles, it guarantees them success. You cannot fail. I don’t care what you’re doing. I don’t care if you apply it to marriage. I don’t care if you apply it to your kids. I don’t care if you apply it to your business, it doesn’t matter.  
In life, and if you look at my life in all the things I’ve done, I can attribute it back to the basic fundamental I learned in that story. Or that, it’s a story I tell, but it’s a real-life event that happened with my father. I always thought, and still to this day think my father is probably the smartest guy I have ever met in my life and he is truly, truly, truly a guy that thinks outside the box. He has no boundary. His mind has no boundary as to what he can be and what he can do and all the other things to go with it. Incredible, incredible childhood.  
Ryan Goodman: So the motorcycle story, you have me on the edge of my seat, my friend. Is this proprietary? Or can I get a confession out of you?  
Tim Conkle: You know what, it’s not proprietary, but it really takes on real meat when it’s white boarded out. It takes about 45 minutes to tell the story. So I would love to tell that today. I don’t think we have time for me to tell that story.  
But the reality is, is everybody, even look at The20, the people live by the principle and it just works. So no, at some point I would love to share that story with you. I just think we’d run out of time today if I went down that road.  
Ryan Goodman: That makes sense. And I think all of you out there in podcast land that are listening to this, I’m taking notes. Please don’t be taking notes while you’re driving. I’d say the call to action here is seek out Tim and seek out the events that he’s speaking at, because I know I’m going to be going to The20 to make sure I’m hearing the motorcycle story, or at least maybe I can get a private session.  
Thanks for that, and thanks for the advice and sharing really what help drove the success and also obviously worked very well in your family to foster the entrepreneur mindset at the beginning of every day and really at the beginning of life, for you guys as a family. Incredible.  
Tim Conkle: Oh yeah. Yeah.  
Ryan Goodman: So, shifting gears a little bit. What are some of the things that you’ve learned in growing your business that most people wouldn’t know, even today, about managed IT?  
Tim Conkle: My personal opinion is that managed IT or an MSP is swiftly getting overtaken by other things. If you call yourself an MSP five years from now, it’ll be kind of like calling yourself break/fix right now. Nobody wants to be break/fix, right?  
I think that stretching the boundaries of what a company is and all the other things. Think about this for a minute as a simple thought. If we think about an MSP, and I tell this at conferences all the time, I would say 99% of MSPs from a client’s perspective is a bad business decision but a necessarily evil. Now that’s a big statement to make.  
I tell people that if I educated them that they wouldn’t sign their own paper. And then they wonder why they have such a conflict getting a client to sign it. It’s because they really don’t like doing business with us. They love what we provide. We provide a working environment and everything. But the actual business itself, I don’t know of any other business on the face of the earth where there is absolutely zero goal alignment. Think about that for a minute, right?  
In IT, for a long time, the goal of the client and the goal of the IT company are two separate things. They’re diabolically opposed to each other because one cannot grow their business and do the right thing for the client under how things are done now. So, I think there has to be a shift in this industry towards more of a business mindset instead of, just this thought process of, “”Okay, I’m going to go in and I’m going to sell this guy IT.” Because it’s such a bigger conversation now. They’re not looking for IT. They’re really looking for more. And then they’re looking for goal alignment.  
I tell this story a lot of times, and it’s simply this. If you were to want a car today, let’s say you had in your mind a red Volkswagen Beetle. It was a beautiful car. It’s what you wanted. It’s got the tulip holder on the dash. Although you’re probably going to put a cigar instead of the tulip in there. So you go and you find a street somewhere in somewhere USA. There’s three dealerships right next to each other and it happens to be all Volkswagen. You don’t understand why, but it’s there.  
So you walk in the first one, you want to drive the red car that’s up on the stands. You drive it. It’s beautiful. It’s wonderful. It’s great. It’s incredible. So you take it down the road. You love it. You come back. You sit down in the office and what is the dying question? What is the dying question that every person has in that room? Or the person that’s buying it, what do they have? And it’s simply this, “What does it cost?”  
Ryan Goodman: Exactly.  
Tim Conkle: The guy tells you it’s $1,000 bucks. Next dealership, you’re a smart guy, you’re like, “Man, there’s two more right next to each other. This is easy, I just walk right next door.” So you walk next door and you walk into that dealership and you talk about the red car and the guy tells you this story, he says, “You know why there’s three dealerships right next to each other? It’s because we’re three brothers and we argued with my dad as to who was going to run the business when he retired. So what he did was he created three offices in this one dealership and said, ‘Hey, may the best man win. But you’re going to scale and share everything together. You’re going to provide everything exactly the same way. Same cars, same service department, same everything.'” So now, the dying question is, when he tells you, “You can buy that same red car from me.” The dying question becomes this, “How much is it?” And the guy says, “It’s $2,000.” And you’re like, “Wow. I think I’ll go to the third one.”  
You go to the third one and he starts to tell you the story, you say, “Hey man, I don’t care. I don’t want to hear it. I know you can sell me the red car that was on the stands. I’ve already driven it. I’ve already done it. Your brother next door already told me why you three exist. I just want one answer and that is, how much is it?” He says, “It’s $3,000.” Which car do you buy?  
Ryan Goodman: You go to the first.  
Tim Conkle: Of course, because you just made a business decision. It’s the same decision that every business makes inside of a room when they have three IT companies in and when the IT company leaves, seven, eight days later they call back and they say, “Hey, I noticed that you hadn’t called us back. I really thought that this was going to be a great fit.” And all the other things. You finally get them to answer you back. They basically say, “We bought on price.”  
Ryan Goodman: Right.  
Tim Conkle: Our industry has long sold on price because there’s no real differentiator. So now they buy on price, but now the frustration that comes in. Let’s say there’s a fourth dealership. This is typically how we sell to our clients. You walk in the dealership, you know the car that you want and that’s that fourth brother that they shoved him way in the back, but you found him and the dying question is, how much is it? And he looks at you an winks at you a little bit and says, “Man, I’m on your side.” He said, “Don’t worry about how much it is. Just take the car. I’ll send you a bill.” How many people buy from that guy? None.  
But it’s the same with the IT. We walk into a room and the guy says, “How much is it going to be?” And we really can’t quantify it. I don’t know what it’s going to be. It depends on what happens. So if our industry doesn’t shift, other companies are going to take our business away from them. Companies like The20, that now have shifted, instead of an IT sale, or even a delivery system, we’ve shifted to a business sale. We have aligned the goals of ourselves and the business owner as one.  
Example, if you took a break/fix company, think about this, sitting at a table and you look across the table and say, “Hey, I’m only going to charge you when it breaks.” And then you ask the goal of the business owner. “Hey, what is your goal?” “Well our goal is for it to never break.” How does the break/fix guy make more money and hit the goal of the guy that’s across the table? It’s an impossibility.  
It’s like telling your kid, “Hey, if you don’t have a dirty room every morning, I’ll give you $100 bucks.” What’s it going to be every morning? Your goal is for it to be clean. It’s going to be dirty every freaking morning, why? Because that is how the reward are enumerated. So IT companies that are enumerated by things broken our out of scope or things like that are always going to major in the ways of making more money.  
Ryan Goodman: We’d like to take a quick break to highlight our sponsors and some of the things they’d like to offer our listeners.  
Do you want to generate more leads and learn how you can grow your business using a proven strategy? Ever wondered how you can leverage digital marketing to accomplish this while taking your advertising to the next level? Then consider having a conversation with Josh Whitford of Josh is an expert at helping small businesses grow using innovative tactics that have worked for large brands such as,, and many more.  
Right now Josh is offering a free strategy session for one hour to do a deep dive with you to learn about your market and collaboratively develop on online marketing strategy based on your target audience. The strategy session is free and you have the flexibility to either implement the strategy yourself or have Josh implement it for you. This is a turn-key solution. This is only for our podcast listeners, so check out Josh and his offering at, that’s  
Our second sponsor for today’s show is BVoIP. BVoIP is the perfect channel-only offering for your IT firm and MSP business. BVoIP works with businesses around the globe to incorporate cloud communications into your big picture telecom strategy. Their program is built for MSPs, IT firms and cloud service providers. BVoIP happens to be the VoIP provider for your friends here at Connect Booster and Connect Booster’s parent company BNG. So check them out on the web at And now back to the show.  
Tim Conkle: So I think our industry, and that was a real long way of answering your question. But I think there’s three basic fundamentals that every IT company, I don’t care how big you want to get, you have got to master three fundamentals, lead gen, you’ve got to make your phone work. You’ve gotta make a potential problem or a company with a problem. You have to make a way for them to call you or find you. Lead gen, you have to do marketing.  
Next is sales. I just talked through sales and how sales are all the same and no uniqueness. The20 brings about a very, very unique way of doing business. I have never had a member not change and shift to this model. Nobody has ever even balked at it.  
The third is you gotta be able to scale. You’ve got to be able to compete with your mind shifts, your all covereds. You’ve got to be able to compete with multi-location companies. If I walk into a company in Dallas and they tell me they have a Boston location and they say, “Hey we want an IT company that has a Boston office.” I’ve got to be able to compete at that level. If I can’t, in time it’s going to hurt all of us.  
Ryan Goodman: So we’ve talked a lot about some of the struggles that the industry as a whole is facing. Things you’re going to need to address. Certainly you have answers to a lot of those struggles and problems and the methodology that you’re working through with your group of MSPs and IT service providers inside of The20.  
How about some of the personal struggles? Some of the, have you had a brick wall moment as Tim Conkle? If you can identify one, and what have you done personally? Because as we’re talking, to entrepreneurs here, not only are we talking industry-wide, but there’s also the mental game of being an entrepreneur and sometimes you’re your own worst enemy. Any examples of that throughout your business tenure?  
Tim Conkle: I think you can look at the first 18 years of trying to build an IT company. My goal was to hit a million dollars in revenue. If you look, 96% of MSPs never hit a million dollars. So when I hit a million dollars I could have said, “Hey man, I’m a 4%er.” And stopped right there.  
Ryan Goodman: Right.  
Tim Conkle: But the real problem was the 18 years. Entrepreneurs and people that are in business have one basic fundamental flaw, they are adverse to change. Even though they know that they have to. It took me 18 years to figure it out. The reality is, I don’t care how many conferences you go to. I don’t care how many tools you buy. I don’t care how many books you buy, how many mentors, how many anything that you do. If you are not willing to change, and for 18 years, I thought I had the tiger by the tail. “Hey, I know how to grow.” But the reality is, the brick wall was literally adversity to change.  
Thinking that … And you can boil that down to living on an island. Every IT guy that’s living out there that’s living on an island, one, never has the catalyst to change. But if you think, it’s ironic, because people go to conferences over and over and over and over. I was at a conference and asked this simple question, “How many people have been here five times?” Had a bunch of hands fly up in the air. And then I said, “How many companies, out of those, have grown five times more than you were when you first came?” And I might have got two hands.  
Why do we do the same things over and over and over and over and over and over and over and over and over and over, when we know damn well they don’t work and then we gripe about not growing? You literally have to change. And that was the hardest thing for me to do. You can’t micromanage. You can’t control everything. In order to grow, you have to change and you have become very open-minded and you have to try stuff. Basically you have to spend money sometimes. And that’s a hard thing for MSPs to get around.  
Ryan Goodman: That’s great advice.  
Tim Conkle: They’re like, “Oh wow. Well if I spend $1,500 bucks for lead gen and I don’t get anything back, man.” Well if you didn’t spend the 15, you’ll never know. I mean. So no, I think the biggest wall was just being able to change. Because when I changed, it was exponential. The growth was exponential. It’s no longer, can I hit a million or two million or three million or four million or five million or six million? The money is a by-product of doing things right. Money follows a successfully run business, period.  
Ryan Goodman: So the advice, if you could talk to your younger self in addition to saying, “Remove the adversity to change.” What would you tell your younger self, now after seeing what you’ve accomplished today?  
Tim Conkle: Knowing what I know, this is pure honesty, I would have started The20 a whole lot sooner. Here’s why, our problem is, as small IT companies. And let’s just talk about sub one million, for a minute, because that makes up 96% of the marketplace. The problem is, trying to do everything yourself and being paralyzed.  
I say this all the time, vision without execution is a dream. You can dream big. You can have a vision of what you want to be, but if execution doesn’t exist … And the problem is a small, small company, execution is a nightmare. Why? Not enough time, not enough people, not enough money. So the only way around that … If you think about The20, just a basic fundamental, let me take just marketing is a basic fundamental. If you took 10 small companies, their thought process would be, “Hey let’s hire 10 marketing people and we’re going to market.” That’s their execution plan.  
Well they don’t have content, they don’t have anything. But that’s their plan. So let’s say they paid each one of them $40 grand, just as an example. That’s $400,000 a year. Wouldn’t it be a novel idea if 10 IT companies were sitting around a table and the 10 said, “Hey, we really need to market. But let’s do it together instead. So instead of marketing one at a time, 10 different times, 10 different ways, managing 10 different people, all of that stuff. Why don’t we do this one time? We’ll market one way, one time, we’ll hire two people to do it and we’ll all get the upside of scale.” Ultimately, that’s what The20 did. In just that example right there, I found $320,000 that is already being spent that has absolutely no return without adding something to it.  
Ryan Goodman: It’s a beautiful concept. And not only beautiful in concept, it’s beautiful in execution as you guys are doing it right now.  
Tim Conkle: Oh, it’s beautiful, yeah.  
Ryan Goodman: I know we have a number of mutual partners coming to see you guys here at the conference here for The20.  
Tim Conkle: Yep.  
Ryan Goodman: Which I would highly recommend individuals to reach out to Tim, his team. He talked a little bit about the ways to contact him and his team at the beginning of the podcast. We’ve really gone through some excellent information here, Tim.  
I almost feel like I’m doing injustice asking this last question, because we’ve really boiled down a number of points. But in closing, if we were to drive home a single point to peers listening to this podcast, and specifically, maybe individuals that don’t know about The20, or don’t know about your story, what do we want to leave them with?  
Tim Conkle: I think simply this, if you look at the next five years in the IT space, what you see is a consolidation happening. Which means there’s going to be lots of big companies to compete with. So as small guys, if we’re going to exist, we have to do something different.  
If you look at the idea of the marketing thing for The20, take that out to all the pieces of an IT company. Your ticketing system, why would 10 companies do it 10 times, 10 different ways? Upgrade it 10 times, maintain it 10 times, pay setup fees 10 times, pay professional services 10 times. At some point, you have to step back and say, “You know what? I don’t have to control every single thing. Let me look at” … And I would challenge everyone, if you truly want to grow and be in a competitive environment, I would challenge you to look at The20.  
And the reason being is, is we deal with the most important numbers on a profit and loss sheet. So if you’re the owner of a company and you own it, question is asked all the time, which number is most important? I always hear the bottom number. I would argue that. I think the most important numbers are the ones in the middle. When we individually, as IT guys, have to pay over and over and over and over and over and over and over, for vendors, minimums and all the other things that go with it, we throw so much money out of the door that’s in the middle, labor, all of that.  
What if we could scale, and that’s what The20 really is, it is a scale organization. How to take a two, three, four, five million shop and make them a 60 million shop overnight. One, giving them a competitive edge and all the other things that go with it. But the reality is, it’s about making the bottom number the best it could be.  
It reminds me of a story with Marcus Lemonis, who does the profit, the TV show The Profit. In this story he’s buying a 50 million dollar company, he’s buying 51% of it. That means that Marcus Lemonis, if he makes this sale, he can walk out in the world and tell everybody that, “Hey, I’m a majority owner of a 50 million dollar company.” So if what you want to do is to be able to tell people, “I have tons of employees and I do this, and I got a million dollars in revenue.” If that’s the horn you want to blow, it’s fine. But it’s kind of like this story. Marcus Lemonis buys 51% of this thing and he buys it for $750,000. 50 million dollar company, think about that for a minute.  
Now, I told lots of people and lots of people said, “Well at least it’s worth one times revenue. 25 million, blah, blah, blah, blah.” No, the problem was all the numbers in the middle was bleeding out. Every bit of profit, so there was no profit at the bottom. So for everybody listening, the thing I’ll leave you with is, every guy starts a business to build wealth, personal wealth for himself and his family. Remember this, it’s all about squeezing the middle to make the bottom really, really plump. I think that’s the best advice I can give people today.  
Ryan Goodman: That’s great advice.  
Tim Conkle: And I’ll say this as my last statement.  
Ryan Goodman: Sure.  
Tim Conkle: And that is, I’m open to anybody, if you’re stuck out there and you’re trying to figure something out and all those things, I’m a very open, easy to reach guy. Reach out to me. I really want people to be successful, period. Whether they’re part of The20 or not.  
Ryan Goodman: Before we end today’s episode we’d like to thank our sponsors, 5Step 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 And check out BVoIP if you’re looking to improve your telecom strategy. You can find BVoIP online at  
Tim, you’re a busy man and I gotta tell you I really appreciate you spending the time with us today to really talk to all of us out in the community. And again, guys, if you’re driving, pull over to take your notes, listen to it again. Tim, it was a pleasure talking to you. And I’m looking forward to seeking you out, ’cause I need to hear this motorcycle story, brother.  
Tim Conkle: Cool stuff man. Hey, I appreciate you guys having me today. And most people will find this pretty crazy but I don’t think I cussed through this thing and typically I do. I mean this was clean, man. People will be like, “Man, that’s a different Tim Conkle you had.”  
Ryan Goodman: You’re a class act man. Hey, do you need to throw something out there?  
Tim Conkle: No, no.  
Ryan Goodman: I don’t want to throw off your game buddy.  
Tim Conkle: No, no. No, no. I’m good. Again, I appreciate you guys having me and I will talk to you guys later.  
Ryan Goodman: Thanks again for joining us today on 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 professional will help you grow your business.  
A special thanks again to Tim Conkle, from Roland Technology Group and The20. Roland Technology can be found online at, and The20 can be found at  
To download the full podcast or to listen to some of our previous episodes online, check us out at  
Thanks again for joining us today on The Confessions of an IT Business Owner Podcast. We’ll talk to you soon.