Entry & Exit #65 Scaling From $1M to $10M: Leadership, Technology, and the Systems That Drive Growth

The difference between a $1 million business and a $10 million business isn't just revenue. It's how the entire company operates.In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down what actually changes as a security business scales from $1M to $10M in revenue. Drawing from their experience building Alarm Masters, they discuss why leadership, technology, and smarter investments become critical as a company grows.They also explain how to escape the owner bottleneck, automate manual workflows, and build a sales team capable of supporting the next stage of growth.

The difference between a $1 million business and a $10 million business isn't just revenue. It's how the entire company operates.

In this episode of Entry & Exit, Stephen Olmon and Collin Trimble break down what actually changes as a security business scales from $1M to $10M in revenue. Drawing from their experience building Alarm Masters, they discuss why leadership, technology, and smarter investments become critical as a company grows.

They also explain how to escape the owner bottleneck, automate manual workflows, and build a sales team capable of supporting the next stage of growth.

In this episode:
→ The biggest differences between a $1M and $10M business
→ Building a leadership team that removes the owner bottleneck
→ Why your technology needs to evolve as you scale
→ Automating manual tasks to improve efficiency
→ Shifting from daily operations to strategic investments
→ Using financial models to make smarter growth decisions
→ Why over-hiring salespeople can protect revenue targets

Connect:
Stephen Olmon — https://x.com/stephenolmon
Collin Trimble — https://x.com/TXAlarmGuy


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 What are they doing that's like super manual, and how do we automate that and throw that workflow into technology to cut that task that normally takes 20 minutes down to two minutes? Everything is filtered through you. You're doing everything at 40% quality because you have too many things on your plate.At one million, everyone is maxed out to 130%. There's no breathing room. You probably won't get to 10 million in most scenarios with really immature tech stack.Welcome to Entry and Exit. My name is Steven Olman, and I also have Colin Tribble with me. And we run this awesome podcast called Entry and Exit, and we also are business partners. We run Alarm Masters in Texas, which is the greatest state in America. Um, today we're talking about how to go... Or really the difference.I mean, it, it would be good if you go from 1 million to 10 million in revenue. I encourage you to do that. Uh, but really talking about the difference. What does a million-dollar in, in kind of top line revenue security business look like versus a $10 million version of that same type of company? And I wouldn't even say a lot of it's inherently connected to the life safety industry.I think a lot of these things are kind of truisms across a lot of kind of sweaty B2B service type businesses. Um, so we'll talk about a handful of really core differences that we've experienced. And so, uh, what's, uh, what's the first one? What's the first thing that really- Yeah ... stands out? We, we talked about this a little bit before the podcast started, but I think the first thing that came to mind is a fully fleshed out leadership team.Yeah. Um, and so you could say people, right? Like, obviously you have more people, um, but if your people... If there's just, like, 20 people and they all report up to you, then you don't really have layers or levels of the organization, and so you are... Everything is filtered through you. You're doing everything at 40% quality because you have too many things on your plate.Versus, you know, at a $10 million business, you're... Which is still not huge, but you've got a, you've got a, a bit of a leadership team. Like, for us, we've got, you know, director of ops, director of sales, director of customer success, director of finance. Uh, d- many of them have managers below them that are doing- Yeahdifferent things and have different groups below them. Um, and that's at w- at each branch location we have that. And so you start to build out, um, levels of leadership. And, and what that does from, you know, in a lot of different ways is obviously it takes off a lot of tactical and sort of operational tasks from the owners- Mm-hmmbut- Yeah ... it also enables you to kind of get into your niche of what you do very best, right? So wherever you are most well spent, your time's most well spent, you can go allocate that time appropriately because you have that time back. Um, the temptation here is, is to take a long time and, like, not to hold onto stuff and not let go of things and, um, you know, that, that's a quick way to be inefficient and, and have your employees on your leadership team leave.Um, letting them kind of... If you find the right people and letting them kind of fail and Try and experiment is the best way to get there. But I, I will say, like, the leadership team is definitely the first thing that came to mind for us. Do you have any comment on that? Yeah. I mean, doer versus designer.We've used that language before, you know? Like at a million dollars you, as an owner, are probably doing way too much, and you probably have not designed a team to be a well-oiled machine. Um, maybe you're starting to think about it. If you're at 10 million, you inherently have delegated some things. There are some systems, there are some people that have proven themselves to be trustworthy and you can depend on.Um, and so at that point, um, ideally you're, as an owner, sitting in more of a designer seat, and that looks like designing teams and systems, and a lot of that is predicated on people that you can build that all on top of. Yeah, no doubt. I also think that, um, you end up finding people that are good at thi- or better at certain parts of the business than you are.Like operationally, I'm not strong. Mm-hmm. And I, and I don't even mean technically. Like, it's not that I technically have it. I just mean I don't think- well operationally. Like, that's not where my strong suit is. Um, I am not a detail-oriented person. Um, I am, like, task-driven, not process-driven, and I think if you are going to be in operations, you need to have, be a process-driven human being.But obviously, like, I do sales really well, but we hired, you know, a sales director who is, thinks just like I do, but we work really well together, and he kind of, like, reads my mind, and I'll be like, "Hey, I wanna go try this thing," and he's like, "Great, I got it," and he can kind of take it off my plate. So I can kind of give him a blueprint for something, and he can go run with it.So I think that that adds a tremendous amount of value to you to enable you to grow and to do what you do very best. Like, every owner has, like, a, "Man, if I had 15 hours a week extra, here are the things that I would do." Like, and- Right ... I would crush it. Um, it enables you to do that. So I, I agree. I think that that is the number one greatest difference.Um, and a lot of that is predicated on the financial ability to, to do that, and when you have, you know, a, a greater, uh, kind of financial means, there's more kind of revenue churning through the system, you can invest in things like, drum roll, brr, technology. Mm. Um, technology and systems, um, that's, um, another very big difference between our experience going kind of from one end to the under- other end of the spectrum, is just a, uh, completely different, uh, set of technologies that we utilize, a real felt expense, both, uh, I mean, time- Yeahenergy, effort, money, uh, that we deployed into that to get from point A to point B. And so, um, if you are at... You know, I, I think about a lot of, like, more, like, home service type businesses that exist on, like, Jobber, you know? And, like, you could scale something like that for a while, but eventually, if you're becoming, like, a mature, sophisticated operation, you have to migrate off of Jobber, and maybe you go to something like a ServiceTitan.You know, if you're in that world, it's kind of a natural progression, right? So in the same way, like, if you are in our industry and you're at a million bucks versus, you know, 10 million, pushing 10 million, technology probably looks a lot different. Yeah, it does. And it, and it's more expensive to own on an ongoing basis, and it's more expensive to implement, but it drives more value.Mm. Um, and most of the technology that you're gonna set up entirely on your own is not gonna drive a ton of value. Um, and you're, you're not gonna ha- And, and even if you c- like Salesforce theoretically you could set it up yourself, but I, I wouldn't, even I wouldn't do it, and I, and I could. Um, and it's like you- the value is in the setup, the value is in the cleanliness of your data.Um, that's where things really become interesting and things become powerful. Um, and you can invest in more data, in more technology that then ultimately automates workflows, which makes your people faster, and it means you get more ROI out of your people. Because something that they used to do that was super manual, you took off their plate.That's the lens through which we look at every single day. I, I think one of the biggest things in my job, literally, is unlocking bottlenecks in the groups of people that work for us to maximize what they do very best. So from the customer success team, to the technicians, to the salespeople, to the billing folks, everywhere across the business, I'm always thinking, "What are they doing that's like super manual, and how do we automate that and throw that workflow into technology to cut that task that normally takes 20 minutes down to two minutes?"And now they get that time back to focus on other things. And, and when you're at 842K of annualized revenue, you are just- Yeah ... hustling. Yeah. Trying to, you know- Yeah ... make things work, and you don't necessarily feel like you have the time or space or dollars to even start to think that way. Mm-hmm. Agreed.Which there is, there is actually a catch-22 there a little bit. I, 1 million to 10 million is a really big gap, and I do think in order to get to 10, you have to start making some of those bets throughout that process to get there probably. Yeah. Um, that looks different for different people in different industries or businesses, um, different like sizes and shapes of that type of decision.But you probably won't get to 10 million in most scenarios with really immature tech stack. Nope. No, you won't. And you've gotta make the... And this kind of leads us to our last point, which is like you've, you've gotta start to make, um, a- a- ultimately $10 million and, and more, and really we started to feel this more around 6, 7 million, you start to make- you become an allocator.And that's basically the majority of what I spend my time on, is evaluating where we should place our bets. And like a really crude way to explain this is like, hey, if you're a stockbroker, your whole job is to take either your capital or other people's capital and put those chips on certain stocks or investments that are gonna return you the best amount of dollars.And you know not 100% of them are not going to hit, and so you just hope more of them hit than, than don't, and you just... And then what you wanna do is you wanna find the double down. Like, okay, is that scalable? Can I, can I do that again, and again, and again? Mm-hmm. And so that's what, that's what I'd spend the most amount of time, my time on is like building stuff, finding things to add, uh, to invest in, and then bringing that to Steven and our leadership team and say, "Hey, guys, like here's what I'm kind of thinking about investing in."Both from a, by the way, both from a time perspective and a money perspective, 'cause as you get to 10 million- Yeah ... and you get more people and you get technology, then you've get- you've got more time to play with. At 1 million, everyone is maxed out to 130%. There's no breathing room. At 10 million, there's not a ton of breathing room because you're growing, but there is more.And so you get to make- Yeah ... a judgment call on what do I wanna invest my team's time in and our money in to really drive the most amount of value. And then it's not just like a lick your finger, stick it up in the air and hope it, you know, which way does the wind blow. You really start to assign numbers and build models behind it to say, okay, well, if I'm gonna invest this many dollars, what do I think the expected return is gonna be?What's kind of my worst case, base case, best case? And like modeling off of that, and then rolling that into your financial forecast to say, okay, what kind of incremental gains does that get me? And so it, it becomes a little bit of a, a finance game once you're sort of at 10 million. You know, you just start to like, okay, how does this affect our business, and what is this gonna do for us next year or even in five years from now?Yeah. We just recently started allocating, uh, dollars to a new hire that you are quite excited about. I am. Which is a fun little tease for maybe a future- Yeah ... episode. Yeah. Um, what, what's, uh, what is a recent allocation decision we made, Colin? Yeah. I, I wanna talk about that hire because- We will ... uh, it, it's, it's been, it's been really, uh, impactful, but I, I won't do it right now.But the, uh- You're not gonna do it. Okay. I'm not gonna say it. Okay. I'm not gonna say it. I want pe- people to hear 'cause the, in the next two episodes they're gonna hear what, who that hire is, and I want them to hear more about that. So, um- Right ... but one- What a, what a tease. Yeah, I know. One of the things that we've, uh, invested a lot in is, um, is salespeople.Um, so we have actually... It's a funny thing. Whenever you start to grow and you start to build a scalable sales team, you say, "Okay, well, I've got, you know, three field salespeople, two, uh, inside salespeople, a sales manager, and I'm producing X million of dollars from this business. Well, in the next year my new goal is to do 100% or 50% or 20% more than that, so then I need to, like, hire to reach that goal."My existing people, like, yeah, theoretically they could produce more over time, but you don't wanna rely on that. You wanna rely on historical data. So it's like, hey, if, if each rep is gonna produce, field rep's gonna produce 3 million bucks, that's $3 million, you know, or a million dollars per rep, it's $3 million.So if I wanna do 5 million next year I gotta hire, uh, I gotta have five reps. But, and that's two big buts, number one, that assumes that every rep hits, and that also assumes that every rep stays. Right. And both of those things are not gonna be true. So you need to actually look at what they actually hit from the year before.You may add a little bit to that, but let's just say it's a million dollar quota per rep but they only hit 750 per rep. Then you gotta actually over-hire by one, but then you found out, oh, I ended up having to replace two reps because I just had natural churn. Okay, well then I need to hire two more to, to cover what is gonna probably be my replacement.Because if your goal is to have five reps at the end of the year, and you only have five reps at the beginning of the year, you're not... Y- y- you have to have five reps fully selling the whole year basically- Yeah ... at a minimum to hit your goal. So that means is for us, we want five field reps, which we have today, five field reps, but we're actually hiring two more.Not that any of these reps we expect to let go, they're all really strong reps, but just naturally speaking- Yeah ... people leave, people move on- Right ... people do things. And so, and we need those people ramped. We can't have them learning right now. So, so that's where we're really focusing and investing dollars today, is investing in the sales team, and over-hiring, and even hiring as an insurance policy to make sure that we are for sure gonna hit our number based on that.Yeah. Speaking of allocation, if you wanna allocate More time to us More likes You could... More likes, more little clickies, you know? Mm-hmm. You could, you could like, subscribe, comment. Yeah. Uh, have a great newsletter, allocate a little time to that, you know? Preach. Little cup of Joe, little cup of us. Yeah.It's nice. Yep. I love it. So just prayerfully consider. Thanks for listening.

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