Scale Like a CEO
Join host Justin Reinert as he sits down with founders who’ve navigated the jump from do-it-all entrepreneur to strategic CEO. Each episode uncovers the key milestones, hard-won insights, and practical tactics you need to build a high-performing leadership team, overcome decision fatigue, and scale your business with confidence. Tune in weekly for quick, actionable conversations designed to accelerate your path to CEO mastery.
Scale Like a CEO
From Vision to Reality: Building a 20-Year Business Blueprint
Twenty years ago, Keith Schoolcraft sketched out an organizational chart for his fledgling IT services company. Taking a Friday afternoon to map his vision for A Couple of Gurus, he created a blueprint for what he wanted the business to become five years down the road. Years later, Keith accidentally rediscovered this document and was stunned by how closely reality had followed his initial plan. That simple exercise hadn't just been wishful thinking—it had fundamentally shaped his decision-making and guided the company's evolution into the successful enterprise it is today.
Keith's approach to scaling reflects a methodical mindset that permeates everything from hiring practices to process documentation. While early growth decisions were reactive—adding staff when workload pain became unbearable—the company eventually developed sophisticated metrics to anticipate staffing needs before they became urgent. Today, A Couple of Gurus uses KPIs like workstations-to-engineers ratios to make proactive hiring decisions, supplemented by an internship program that creates a pre-vetted talent pipeline.
As the company expanded, Keith discovered that processes that worked perfectly for small teams often failed at scale. Creating comprehensive knowledge management systems became critical, leading to the implementation of an enterprise wiki in 2004 that continues capturing essential organizational knowledge today. Keith's "salt shaker principle"—inspired by high-end restaurants where items always return to their designated positions—provides a framework for maintaining standards across the organization while successfully delegating responsibility.
Now serving clients nationwide with team members distributed across multiple states, A Couple of Gurus stands at the exciting intersection of established IT services and emerging AI capabilities. Keith sees this technological evolution as the next frontier, presenting opportunities to help clients leverage new tools strategically rather than fearfully. His journey offers valuable lessons for founders in any industry: create a clear vision, build scalable processes, embrace delegation, and never stop learning from the community around you.
Yeah, you know, one was deciding.
Speaker 1:I think having a plan for what you want it to look like is helpful.
Speaker 1:I remember when it was there's just a few of us in the beginning and I had done this org chart and it was like what I wanted the organization to look like in the future, you know, and I knew that future wasn't today, you know, but it was like maybe five years away. What was fascinating is I had ran across accidentally ran across that document some years later and I was really surprised at how close we ended up moving into that direction, because I had taken that time, you know. Uh, I probably took a Friday afternoon off and just kind of said, hey, what do I want this thing to look like in the future, you know, and and that was a big piece of the puzzle, but it what it ended up doing for me is it helped eliminate decisions, because I knew how I wanted to create the teams, I knew how I wanted to start, you know, uh, what departments I wanted to create and things like that, and a lot of those things are still intact today, you know, which is pretty cool.
Speaker 2:Welcome to Scale Like a CEO, where we dive into the journeys of successful business leaders. Today, we're exploring the story of building and scaling an IT services company. We'll be talking with Keith Schoolcraft, who's grown his business from a small team to a thriving enterprise over two decades.
Speaker 3:Keith, thank you so much for joining me on Scale Like a CEO. Just to get us started, I would love to hear a little intro about yourself and your business.
Speaker 1:Yeah, my name is Keith Schoolcraft and I'm the CEO of a couple of gurus. We have been around for over 20 years, based out of the Twin Cities in Minnesota, and just have had a long-term passion for technology and serving customers, and ever since I first started I wanted to grow the business, and so we've done that, slowly over the years and methodically.
Speaker 3:And, within the industry that you serve, what's one of the biggest challenges that you're solving currently?
Speaker 1:Yeah, a lot of us. We serve a specific marketplace, which is the SMB marketplace, and they still have the same challenges larger organizations. So if you look in the manufacturing sector, for example, you've got large manufacturing that will have internal IT departments, whatnot, and then you have small, midsize manufacturing that may or may not have anybody in that space and in today's world of CMMC regulations and other, you know, other cybersecurity things that they'd have to adhere to, it's really hard to find folks that can do that kind of work as well. So the CMMC space is one, the med device space is another. The CMMC space is one, the med device space is another. Those are a couple of spaces we specialize in that are kind of unique, that not everybody does.
Speaker 3:Excellent, Excellent. And so you said you've been running the business for 20 years. I'd love to hear a little bit of the journey of guessing you started out as one guy or two. One guy? Or two, two. Well, you're two, two gurus, right.
Speaker 1:So you're bigger than that now, I believe, Right so tell me a little bit about the journey of how you grew the team. Yeah, you know, uh, one was deciding. I think having a plan for what you want it to look like is helpful. I remember when it was there's just a few of us in the beginning and I had done this org chart and it was like what I wanted the organization to look like in the future, you know, and I knew that future wasn't today, you know, but it was like maybe five years away.
Speaker 1:What was fascinating is I had ran across accidentally ran across that document some years later and I was really surprised at how close we ended up moving into that direction, because I had taken that time. You know, I probably took a Friday afternoon off and just kind of said, hey, what do I want this thing to look like in the future? You know, and and that was a big piece of the puzzle, but it what it ended up doing for me is it helped eliminate decisions, because I knew how I wanted to create the teams. I knew how I wanted to start. You know, uh, what departments I wanted to create and things like that, and a lot of those things are still intact today, you know, which is pretty cool.
Speaker 3:Yeah, that's great, I love you know it happens like that, right, you sometimes set out on a vision and even if you don't have that thing in front of you, it was still all in here anyway, and so you've got that that you're carrying with you, and so you know what were some of the decision points that got you to say, yes, I can add this person to the team. And you know, I think that's one thing that founders often struggle with is're like oh my gosh, our workload is so high.
Speaker 1:We're having a hard time staying up. We need to hire someone else to help with this. As we've gotten along, we've gotten a lot more methodical about it and you start measuring things right. And you start measuring things right, so you start putting together some KPIs, some key metrics. You know, number of workstations to engineers, for example, is one metric right, the amount of tickets created per endpoint, different things like that that actually help you decide how many engineers you need. So, and now when you bring on clients, you can say, okay, this client is this size, or we've brought on X number of these types of clients. We know that by you know, at this current rate, you know, by fall or by spring, we're going to need some additional and Um, and then where we, we have shifted, uh, and this has been how it took a long time to kind of get here.
Speaker 1:But um is, we started an internship program, um, and that internship program has been really great and not every, every intern stays on for for a job. But, uh, they do gain valuable skills, uh, and it's a lot of, it's a lot of fun to work with them and watch the young folks grow and, you know, see their eyes opened about all the different possibilities, but then sometimes the opportunity is right and you add them to the team, and so then it starts to. What's nice about that is they're already a little bit familiar with kind of how you do things. What's nice about that is they're already a little bit familiar with kind of how you do things, and so when you get to that point where you can have those internships, it really changes the hiring cycle.
Speaker 3:Yeah, that's great. I think it's a great. That's a great opportunity to be able to try out talent before you commit and it also gives them some real world experience. I love that so random and I rarely, you know, plug other businesses, but I'm curious if you've ever heard of Parker Dewey and their micro internship.
Speaker 1:I have not. That sounds interesting.
Speaker 3:So I'll have to I'll connect you with some info later then because they they do these micro internships where it's a really great opportunity, where it's, you know, it's not even a full summer thing, it's a. Here's a very discreet project that I need worked on, Um, and a lot of those things then turn into longer term projects, Um, you know, it's like another great way to try it out, um, but your, your, your internship program just made me think of that and bringing on full-time people.
Speaker 3:But as you transition from just a few to growing the team, what are some challenges that you encountered in that journey?
Speaker 1:The processes that you developed, two things happened. One is communication changes, and the processes that you developed when the team was smaller don't always scale to when the team is larger, and so that's an area that people sometimes forget to look at. And what ends up happening is when you have a process that starts breaking down, you kind of look everywhere else first until you realize let's review the process, and sometimes where you keep your process documentation, and sometimes you end up having process documentation in more than one location, or you'll use some process automation software. Well, does your process automation software match your SOP? And we found a few instances where they were close but they were slightly mismatched and it was causing problems.
Speaker 1:Uh and uh, you know you don't discover those things, um, until you've you've been running those processes a long time, and then usually it's something changes, uh, that that forces you to.
Speaker 1:Um, you know, maybe you had a person, a personnel change or someone had to take over for a while, and then and forces you to. You know, maybe you had a person, a personnel change or someone had to take over for a while, and then, and then you really find out. You know, I always kind of use people go on vacation and someone else does their role for that period of time, like it's sort of a test of your process, documentation of how well is it written and and how well you know how well can someone else pick it up. So you sometimes, when you can do a little test like that, it it helps you, uh, find the gaps a little bit, um, but you know as you get, you know as as the further along you go, the more sophisticated, the longer your processes to get, the more sophisticated they get and the easier it is for them to have variants.
Speaker 3:Yeah, I can imagine that. Imagine that being challenging. I mean, there's just the knowledge management piece can be so challenging and as you scale and try to rely on that knowledge management, it's really a test of the quality of that knowledge. It makes me think of there are times when I've had you know, when I've been running teams, where I've had turnover and I knew that we didn't have you know, that there was too much knowledge in that person's head. But I also realized that you know I could understand, like what are the critical things? That if they fall down, that you know things are really going to fall apart and I would grab those and sometimes I would kind of let everything else fall, like let let the pieces fall because let's test our systems and see, like, what actually needs to be rebuilt, what isn't, you know, working right, um, and so, yeah, it's an interesting opportunity.
Speaker 3:It's your. When you said, um, when you've had people go on vacation, that being really a test of right, the documentation, that's what made me maybe think about it. You said, um, when you've had people go on vacation, that being really a test of right, the documentation, that's what made me, yeah, maybe think about it one of the things that we did over the years and still do, um, uh, you're, you're, familiar with a wiki like wikipedia.
Speaker 1:Um, we have an enterprise wiki, enterprise grade wiki that we use internally, um, and and the whole sole purpose and we've we've we've ingrained in this into our culture is to capture that tacit knowledge that people are keeping in their head. And you know, I'll tell engineers or even administrative people like you don't have your. Your documentation doesn't have to be perfect. Just write down the 10 relevant bullet points that we need to know. You know we can figure out the mechanics of how to push the buttons, but you know we need to know what those decision points were that were critical in. You know what you decided in setting said thing up Right, and that has really helped over the years. We've been able to keep that tacit knowledge in-house as a result of having that wiki database in-house.
Speaker 3:Yeah, that's great, and I'm curious, if you've looked at just a side tangent that's making me think of this is I'm curious if you can take these big bunches of disparate information and kind of essentially throw them in a drive hook up. You know one of the generative AI tools and you now have your knowledge base right. I'm curious if you're doing anything with that.
Speaker 1:Yeah the Microsoft's co-pilot has. I call them connectors, microsoft calls them applications. They're fundamentally a connector to another application, and so in our case, we use a Confluence wiki by Atlassian, and so Atlassian is pretty well known company out there, and so we can now open a copilot instance that's to our Atlassian instance and then query all the knowledge base that's in there, because we've been entering data into that wiki since we first started using it in 2004. So that's a long time to put data into a system, and so one can imagine that after a while it can get hard to find things, and that's where AI can help bring that together.
Speaker 1:And I've seen a lot of people because over the years, people have a tendency to keep everything because they don't know if they're going to need it at some point in the future. We see this with clients all the time, where they're afraid to get rid of their, their data, and this is sort of becoming a little bit of an issue for AI. Because you know, if you have, um, you know, 12 versions of your company handbook, which one's the authoritative, you know AI is going to read them all, you know. Uh, so there's, there is a situation going on here where us and everyone, because Microsoft's co-pilot is contextually aware of your entire environment. So it's aware of your SharePoint, it's aware of your email, it's aware of all these things. So kind of pairing your data to authoritative data is something that we need to start thinking about.
Speaker 3:Yeah, that's interesting. I haven't thought about that. But it's like you know, managing a database, right?
Speaker 1:Garbage in garbage out.
Speaker 3:You've got to keep your data clean.
Speaker 1:Yeah, 100%.
Speaker 3:Yeah, Okay. So I want to go back to others on the team. As the team grows and you said kind of one of your pain points or what you decided to move forward with is when it's too painful or when you've got too much work and it's time to just start adding people. So tell me a little bit about that balance of delegation and when you know it's right to start delegating work.
Speaker 1:Yeah, I think I there's a little thing I kind of would say to myself in my head which was it? If it, can I delegate this and will it? You know, and let's say they really just really fail on it, Is it going to take me down? And let's say they really just really fail at it? Is it going to take me down? If the answer is no and it's just causing a little bit of pain, then delegate it, Right. If it's something that's going to take you down, then you need to question, Right, and then maybe you need to delegate that. If you're going to delegate it, delegate it with, uh, you know, a lot of process, uh, and and clear, defined expectations behind it, Right, Um, a lot of the other stuff that we worry about delegating is is immaterial, Um, and I think you have to kind of come to terms with yourself that no one is ever going to do it exactly the way you do it.
Speaker 1:But if you can impart on them the principles behind the way and why you do things, they tend to will want to adopt, that you know, um, I have this principle of the salt shaker that I, that I tell, tell people which is when you, when you go at a uh dying at a high-end restaurant, you'll notice that after someone leaves there's a very specific spot for all of the things on the table. So the salt shaker has a very specific spot and as people are dining and coming and going, you'll see that waiter or waitress they'll always put those items back in the very specific spots they go. So I teach that principle to our team, which is if you see something at a client site that seems off, that's outside of our standard way of doing things, that's a salt shaker situation and you need to move that salt shaker back to that center of the table where it belongs.
Speaker 3:Yeah, that's such an interesting analogy. I love it. I haven't. I haven't heard of a similar analogy before, so I really like that. So I'd love to hear about your vision for the future of the business, and you know what's the, what's the future look like for a couple of gurus.
Speaker 1:Yeah, we, I mean we continue to plan and grow. We currently, with, you know, while we're Minnesota based, we've started to expand beyond this geographic region, especially with computing, a lot of computing being in the cloud these days, it doesn't really matter where clients are located, um, so our team is now distributed, um, uh, in several States. Uh, as a result, uh, and so, um, that's really opened up new opportunities, um, that perhaps in the past, you know, we wouldn't wouldn't have considered, and so now we're serving customers and and clients across the United States. So it's a it's kind of a fun time. I think we'll continue to.
Speaker 1:I think we're at the beginning of this whole AI.
Speaker 1:You know revolution, evolution, and a lot of people are still getting their head around it.
Speaker 1:A lot of people are, you know, figuring out what they do, and that, for me, is the exciting part of technology is discovering its potential and what it can do for you and how it can make life better. You know it. We, you know society, has always appreciated the advancement in technology. It has allowed us to do things that we couldn't otherwise fathom before. You know you just look at transportation right how long it took, you know, for aviation industry, when, when the airplane first came about to jets right, that time span was, you know, whatever a little less than a hundred years, but it made a great impact on society, and I think we're going to see the same thing with AI, and so I think part of my excitement is discovering and figuring out what's our role going to be in that, uh, in that as, as it unrolls, and how can we get people thinking differently about, you know, not not being afraid of it, right, uh, but taking advantage of it and using it strategically, you know, uh, and and using it to make life better.
Speaker 3:Yeah, that's so great, and you know how big is your team today and how big is it going to get.
Speaker 1:Yeah, so today we're about, we're right, around 20 people and we will, which we have approximately stayed true to the one person per year ratio. That'll probably accelerate, actually, as as we move forward. Um, uh, uh, I, I would, I would expect that rate to to start to double. Um, you do, when you get to a certain point, um, you know, there's a lot of things that are hard to survive for small businesses, right, um one, when, in the beginning, you're trying to figure it out, right. Then, when people hit their first recession Right, my first recession was the 2008 recession there's business schools don't go over how to survive recessions, right, that's not a class, you know, you learn that by trial and fire. Right, you learn that by trial and fire, right, you, you learn that, uh, by going through it. Um, so, uh, uh, uh, you. Then you start to that knowledge starts to build upon itself, right, and so you know it's.
Speaker 1:It's interesting to see companies at different stages because you know they're. You know, at the beginning you're trying to figure out, well, how should we do payroll? Well, you know, now, we're you know now, then we hit the how do we do payroll in multiple states with multiple laws and multiple, you know HR things to figure out right Like that. That that's a different, you know. So going back to doing payroll at a single state would be nothing, right, you know. So as you start to go, you are learning different things and you are able to accelerate your growth because you're not going back from the beginning again.
Speaker 3:Yeah, I would imagine there's a lot of lessons learned in there and you can just kind of continue to to multiply your growth Well, and the other thing is you're not afraid to learn from someone else. Yeah Well, and you know, when do you make that that pivot, that you're not afraid to learn from someone else.
Speaker 1:I see a lot of people. It's usually when, when they've tried everything, everything that they can think of, that works, and they just run. You know, sometimes you get too laser focused in your own wheelhouse or in your own business, you know, and you don't see what's obviously in front of you. I had a friend once who ran a similar company up in Canada. He's since retired but he was losing this major client. And that's one of the things that a lot of people will experience either a loss of a major client or a loss of a key person. And those are things you don't normally plan for.
Speaker 1:And he realized that you know he had too much staff for you know, the managed services side of his company. And on the same note, about 10 minutes earlier, he was talking about you know how do I? He's got all these projects and he didn't know how he's going to get these projects done. And I said to him wait a minute. He was at a point where he was thinking about letting staff go, but yet he had this other side of his business that he didn't have enough staff. I said have you considered moving some people over from side A to side B? And it was such an obvious, simple, you know answer to the problem to someone on the outside, but he was so close to it he couldn't see it. And you know, and I I knew he just needed more time to backfill you know the revenue loss. And he went ahead and and implemented that strategy, uh, and, and you know, over a couple of quarters, recovered the, got the projects done and recovered the loss revenue over a couple of quarters, you know.
Speaker 1:So, uh, sometimes I think if you're too, if you're too close to it, that's a great time, uh, to bring somebody else in. Peer groups are great for that and you know whether they're an industry peer group or a local owner's peer group. There's. A lot of people have come before you. After a while you start to realize that it doesn't matter what business you're in. There's a certain set of fundamentals that are universal. Uh, and you know, dealing with people is one of those things. Um, and those are are things that other people can speak. Uh, speak into those problems and you know you can really learn from what. How did they handle a situation? You know. And then you take that knowledge and you bring it in house and, and you know, figure out how you need to, to, to attack the problem, you know.
Speaker 3:Yeah, Thank you for that. Community is so important, I think, in in learning and growing and kind of seeing how other people do things. Yeah Well, Keith, thank you so much for joining me. Uh, on me on Scale, Like a CEO, If people want to get in touch with you, what's the best way for them to find you?
Speaker 1:Yeah, feel free to send me an email directly. Keith at a couple of gurus dot com, Happy to chat. I always love talking business with people. Even if you're in my same industry, you know there's plenty of work to go around for all of us. Let's move forward together.
Speaker 3:Great. Thank you so much, Keith, Thanks.
Speaker 1:Justin.