Founder’s Journey: The First 90 Days After Buying a Business

Most people dream about buying a business. The first 90 days show you what ownership actually feels like.

In this episode of Entry & Exit: Founder’s Journey, Stephen Olmon and Collin Trimble break down the chaotic first three months after acquiring Alarm Masters — from stolen equipment and blacklisted domains to learning every role inside the company.

They share the real lessons from stepping into a service business as young operators: resisting the urge to change everything, surviving technology disasters, building trust with employees, and discovering what kind of company they actually wanted to build.

From making collections calls and site visits to uncovering broken systems and redefining culture, this episode is a raw look at what happens after the deal closes — when the real work starts.

Inside this episode:
→ Why they focused on being great employees before great owners
→ The brutal technology and email issues that hit immediately
→ Lessons on working capital, WIP projects, and key man risk
→ How they earned trust with technicians and staff
→ The discovery that shaped their sales-driven growth strategy
→ The coffee-drop tactic that became a scalable pipeline engine

🔗 More Entry & Exit — https://www.entryandexit.co/

Connect:

Stephen Olmon — http://x.com/stephenolmon

Collin Trimble — https://x.com/TXAlarmGuy

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Transcript

Website Blacklist Chaos

SPEAKER_01 0:00

In the first 90 days, it wasn't perfect because when you were what 31 and I was 34, our site was like blacklisted from the internet.

SPEAKER_00 0:10

So hard, so bad, it was sending all of our emails to customers to web servers to spam. And so we were sending invoices out of huge amounts. And they were customers weren't getting the invoices.

SPEAKER_01 0:24

And we're like, you know, the new owners and everyone that you guys are spamming us.

Welcome Back and Van Break In

SPEAKER_00 0:31

We invested in our employees by showing them that we were never gonna ask them to do something we weren't willing to do. And then I think the last thing we learned was just like we were gonna be a sales-driven organization. And that's what we learned in the first 90 days, only because welcome to Entry and Exit Founder's Journey, Episode 2.

SPEAKER_01 0:55

And we're back at it. And if you didn't if you didn't listen to the first one, at the very end, we told uh a story about kind of our our first day in seat. And we in case you haven't, you know, just to be nice, to be considerate, I will let you know again that 8 a.m. we show up and one of the vans was broken into four thousand dollars of equipment was stolen. Just punch in the face. Welcome to SMB ownership, Stephen and Colin.

First 90 Days Discovery Mode

SPEAKER_00 1:27

Yeah, that was uh I think actually what happened, if I recall it correctly, we signed our our SBA paperwork, signed the purchase documents, met with the employees, and then walked in, and somebody was like, Hey, I just got a call from the I think it was the next morning, but maybe it was the next day. It was the first full day. Yeah, I don't remember. I just remember being like the first thing. Yeah, that was not a fun way to kick off the journey, but it was a very realistic kind of um it's like they say if it if it rains on your wedding day, it's good luck. It's sort of like the same thing. Like, I think we've had great luck because it rained on our uh signing day or whatever, and so we've been things have been great, but uh yeah, that was a that was a really great sneak peek into SMB ownership. Um, but here's what I'll say like, and I think we did this right. We really focused on how do we be the very best employee that we can be, and not how do we be the best owner. So we weren't trying to change stuff, manage stuff, really provide any level of feedback, uh, just trying to do all of the jobs uh to get exposure, uh, take people to lunch to really get to know them.

SPEAKER_01 2:42

The owners, too, is a husband and wife, duo, and we knew we had them for like a minimum full-time 90 days. Yeah. And uh the husband, uh Brian, he ended up being with us probably for about four and a half, five months. Yeah. Um, and uh then Tina's with us for six months or so.

SPEAKER_00 3:04

Yeah.

SPEAKER_01 3:05

Um, so that was helpful.

SPEAKER_00 3:06

And that was a huge help. And I would say if you're buying a business and it's your first platform, you need to negotiate for like likely longer than 90 days, unless you like I had industry experience, and even still, and Steven and I have run other businesses prior to this, so it's not like we didn't have business acumen, but running a business with I forget how many employees we had, 11 or 12, yeah, uh, and a bunch of customers, thousand customers, is a different story. And so, yeah, we learned we learned a lot. We also learned, I think, Steven, you can agree, how much work and key man risk was uh landing on those owners uh then more than we anticipated. I mean, they were working two and three jobs, yeah.

SPEAKER_01 3:49

They had multiple jobs essentially, and they were living at the office, like they were grinding and they were in their early 60s, like yeah, it was uh it was not like a precious little small business, and they're just kind of chilling. They were after it.

Tech Debt and Legacy Systems

SPEAKER_00 4:06

No, yeah, it was it was a lot, and I will say this um, that first 90 days I was very anxious because I was like, dang, I don't know how I'm going to improve all this stuff and do both of these people's jobs because I kind of acted as the main operator, and Steven was really managing a lot of our back office stuff, and so I was like thinking, how am I gonna really focus and do a lot of especially what Brian was doing because he was doing all of sales, all of operations. It's insane. And so we we really wanted to fix a bunch of stuff. The temptation in that first 90 days is like, I'm gonna go fix this, I'm gonna go do this, I'm gonna provide feedback, I'm gonna cut these employees, and we really did it. We we only cut really one employee in the first 90 days. Um, and this was an employee that was a friend of the owners that they were kind of high hiring part like for a short period of time, a season while the guy was between, I don't know what his deal was, I don't even remember. Um, and he just really wasn't he wasn't really doing anything and he was just kind of helping out around the office. And so aside from that, we really didn't let go of anybody or make any staff changes in the first 90 days.

SPEAKER_01 5:11

We also did not really change much, if anything, along the lines of technology quickly, but we quickly learned how god-awful, you know, the legacy systems they were using were and all the gaps. Like, man, we probab not that we wouldn't have done the deal, but we probably should have leaned in harder to fully understand the technology gaps they have.

Daily Grind and Office Move

SPEAKER_00 5:37

Yeah, yeah. I think a lot of people that are buying businesses, especially young, uh uh young folks that are like, I'm gonna go buy this whole business, really undervalue or don't think enough about how hard that technology transition is gonna be. And in our case, they've been using the same platform for 20 years. Yep. And so all the data was there and it wasn't in a normalized database, and it was just a mess. Like it was so hard, it was all local. So it's like, hey, you want to go like customer calls you in the afternoon on your way home and say, Can you send me this invoice? No, not till tomorrow. I can't. It was just it was tragic. I mean, that was really hard. And so what we really focused on, I I mean, you can correct me if I'm wrong, was let's not change anything. Let's figure out the state of the business, let's understand the team, let's develop a culture, let's understand and take a lay of the land, let's do a 90-day discovery and be as effective as we can. Let's work late, let's stay long, let's get there early, let's figure out what we have to do so that we can understand what needs to be fixed. And then at the end of the 90 days, we can really prioritize what we need to do. But in that first 90 days, it was fixing. I mean, I remember literally making uh collections phone calls for two hours in the morning, and then I would spend, uh, I'd go out and do a couple site walks, and then I'd uh come back and I'd go grab lunch with the guys uh at a job site, bring them lunch. I'd I'd go to another project to check in another guy, and then I'd come back and I would do trouble signals to call customers that had low batteries or whatever on their systems, and then do answer any emails, and then I would like try to close out the day with some sales initiative. And that was like every day for the first 90 days.

SPEAKER_01 7:17

One of the things that we did change in the first 90 days or right around day 90 was where the office was, because you you know, you're driving all over Houston, but the office, I mean, you were driving what, hour and 20 minutes one way? It was insanity. And so that's one thing that I think you know, you brought it to me, but I was like, I mean, because I was in Dallas and I was like, dude, you you're gonna waste away on the highway killing this like precious time, yeah. And it's gonna be demotivating, discouraging. So one thing we did do was we did move the office much closer, kind of up to the the north side of Houston, which I think was a yeah, really good decision than we did it when we did.

SPEAKER_00 8:02

Yeah. We also didn't hire anybody new. We did promote somebody internally, but we didn't really hire anybody in that first 90 days.

SPEAKER_01 8:08

Yeah.

Working Capital and Cash Lessons

SPEAKER_00 8:09

Uh and uh we we promoted some uh one of our senior techs to be kind of an ops manager type role to really interface and take some of that load off me. And in the early days, that was really helpful to just kind of deflect some of the highly technical stuff that was coming in. Um, and dude, I I I think about all the time like all the just like random stuff that you get hit with in that first 90 days that you're just like chomping at the bit, you're like, I could fix that, I could fix that, I could fix that. Like, what are we doing? And we really had to like bite down and be like, okay, we're gonna wait. We committed to 90 days of discovery and just stressing out about that. Hey, how about this though? One thing, kudos to you from a like kind of financial diligence perspective. One thing we didn't stress about, and I think a lot of people do when it's early operator, is working capital. Yeah, um, we had plenty of working capital that we brought into the deal, um, and the business was kicking off recurring revenue and it was running pretty lean. So on hand cash wasn't our our big concern. And I would say that a lot of operator journeys don't have that. They say, dang, I did not get enough operating or sorry, working capital. I should get I should have gotten more working capital to start. And I think you know, we we did a good job of of that.

Email Spam Disaster and Domain Switch

SPEAKER_01 9:27

Yeah, it's hard when you do have plenty of working capital. Yeah. So yeah, I was very grateful that we kind of um I wouldn't say it was excessive, no, but it it was like a healthy amount. And um we never really there was I can remember one month, which I know I'm kind of jumping ahead, I won't you know go deep on this, but I can remember about nine months in because we were trying to scale and we started to started to change some things where maybe there was a month where we were like, man, cash is really tight, you know, for what we felt comfortable with. But other than that, we never really were in that hard of a a place from a cash position, which is a huge blessing. Um, one thing that was not a blessing was that Steven, Mr. Marketer, decided Oh god, I forgot. Let's upgrade the website. Because it was, you know, it was a little rough. Like it it looked old, it presented old. And so I was like, hey, we're gonna it gave boomer. It it it was presenting boomer. Love y'all, Brianatina, if if you ever watch this. Um and I I still to this day, I don't know what happened, but somehow in making that transition, I still think it was GoDaddy's technical team that made a mistake and then never wanted to admit it to me, even though I like tried to make them admit it. But somehow our site ended up getting marked as malicious. So we had alarmmasters.com, which is like a nice domain name. Sounds good. Well, today, if you try to go to our website, it that would redirect, and we live on the alarmmasters.com because our site was like blacklisted from the internet so hard, so bad.

SPEAKER_00 11:13

Well, and it went, it went levels deeper than that because not only was our website it would say malicious content, so you couldn't get to the website at all, which was a problem. But the bigger problem that we had was that it was, do you remember this? It was sending all of our emails to customers' web servers to spam. Yes, and so we were sending invoices out. Oh, it's a huge and they were customers weren't getting the invoices, and and even just wrote customer communication. We would just be like, hey, by the way, blah, blah. They wouldn't get it. So we were calling them, like, oh yeah, your emails in our spam. So I I mean, I I remember like losing my SHIT because I was like, dude, what?

SPEAKER_01 11:50

Like, we're already in the thick of it, and I can't send emails to customers, and we're like, you know, the new owners, and everyone's like, you guys are spamming us, and it just it was so bad. And so finally we just made the decision to make the hard cut over to the new domain, and it was really painful, but it was the right decision because we just were able to move on from that problem, yeah. Um, but uh years later, we finally, after all sorts of appeals and submissions, were able to finally like clean up. So we still have that old domain, but uh man, just stuff that you don't expect. It's like really like come on, like don't yeah, don't tell me we're gonna have to deal with this, also.

SPEAKER_00 12:31

Another thing that I thought that was really challenging was um, and again, if you're buying a service-based business that does projects, this would be a big one, is like managing WIP uh work in progress projects where things were agreed to with the prior owners that I maybe wouldn't have agreed to, and I was like, okay, well, whatever. But then even stuff for like months-long projects, so then like the old owners were out, yeah, and then like the project was kind of left and not in a perfect state just because the transition wasn't done. And I honestly take full responsibility for that, but it was like it just it was challenging, like do handling the projects that were in flight, those ended up being zombie projects for us that just kind of carried on for a while. And we had hired, you know, promoted a new ops manager, and he was kind of involved in some of those, and some of them he wasn't. And it was just like if you're you get your hands around the whip really tight. Like, I would say first 90 days we did not focus on that enough. Where you got to get in and understand where are the projects, where are the financials for those projects, where's the billing, like what is the customer's understanding of the scope and punch list? Like, it literally might be worth sitting down and doing like redoing like a kickoff meeting right in the middle of the project to say, hey, here's what I'm reading from the scope, here's where we are on this project. Like, how do you feel about everything going on right now? Because that was a time vortex.

SPEAKER_01 13:52

The last thing I'll say is in the first 90 days, it wasn't perfect because you were what 31 and I was 34. Um we were young. 34 and 32, 32 and 34. Yeah. Yeah. That's right. So, but like we presented young, you know, and that was felt. But I do think in the first 90 days, I do think that um, I would say especially you did a really good job at building rapport and gaining trust. And like, yeah, you know, look, first few weeks, did some of those technicians go home and tell their significant other, like, dude, some kid bought our like probably that would have been fair, yeah, you know? Yeah, uh, but I do think in the first 90 days we started to gain some respect and trust.

SPEAKER_00 14:42

Yeah, I agree. I think that we invested in our employees by showing them that we were never gonna ask them to do something we weren't willing to do, and by leading with uh a question rather than uh a prompt or a command and just asking a lot of really good questions. And I think that that really changed the game. And and just to close out this this episode, like I think what we learned in the discovery was a few things. One, we desperately needed new technology, didn't needed a CRM, and needed everything to be on cloud so that I could work from this anywhere, needed to be able to do uh move the office so that I could have better quality of life, so I could be at the office and not have to commute three hours a day. Um, we needed to cut some people internally that were redundant or not really working hard enough. We needed to promote other people that were doing a great job and were underutilized. Uh, I think we also learned that there was a lot of there was no vendor relationships really. And so we we really spent a significant amount of time building dedicated vendor relationships so that we could start selling and getting economies of scale and getting our techs you know more equipped, et cetera. Um, and then I think the last thing we learned was just like we were gonna be a sales-driven organization. I think that this industry is characterized by being operations driven. We really wanted to be sales driven. And that started with the origin of me doing coffee drops. And what that was is me just going around to our top 100 customers and just dropping off a coffee. And while I was there, I was just getting tons and tons of pipeline. And I realized that was the inception of dang, that's a whole sales strategy. And in Stephen's words, if you could do it once, you can do it a thousand times. Amen. And that has been the motto of our entire business, and that's what we learned in the first 90 days, only because we wanted to be great employees and not be great owners. And if we would have skipped ahead of that, I don't think we would have gotten any of the value.

SPEAKER_01 16:27

Totally agree. Um, so the next time on Founder's Journey, I think we're covering kind of the the first full year. Yeah. Um, and some of the themes from that, which were gnarly things. So um, if you're interested, like, subscribe, please, um, you know, put like a little heart emoji on. Yeah, if you would whatever you feel like, you know, send it to your mom. And uh well, yeah. Oh, with the other half? Oh, yeah, there it is. We're like rough alarm, blue collar, big blue collar energy. Um yeah. Um, so yeah, that's a wrap.

SPEAKER_00 17:09

Thanks for listening. Appreciate it. Have a great week.