The Weird Stuff You Inherit: Policies, Holidays, and Other Surprises After Acquisition
19 Dec 2025 · 22 min
In this episode of Bought the Biz, hosts Garth Fossano and Christi Loucks discuss the unexpected operational and cultural quirks they discovered after acquiring small businesses. They start with the lack of formal holiday policies, describing how holidays were handled inconsistently across multiple time zones and how split‑week schedules created confusion. They recount informal practices such as treating "commute time" for remote workers as paid work, and the legal gray area it raised. The conversation moves to remote‑team monitoring with Hubstaff, revealing how employees gamed the system and how sick‑day abuse (e.g., repeated migraine claims) forced the creation of formal policies. Throughout, they contrast informal, family‑like cultures with the need for formal HR policies as businesses scale, sharing personal reflections on the tension between trusting employees and protecting the company. They also touch on leadership insecurities, the importance of understanding granular processes, and how hands‑on experience builds strategic insight. The episode ends with a light‑hearted acknowledgment that business ownership is inherently weird and a holiday farewell.
Chapters
Welcome back to another episode of Bought the Biz. As we head into the holidays, Christi and I are both thinking about some of the oddities and the weird things that we found in our businesses when we took over. One of the top ones on our list is holiday schedules. Are they even written down? Is there a handbook? How does that work? And all of the questions that unfold after that. Stay tuned for this episode where we talk about all the hidden surprises that we found in our business and then get into leadership traits, all these other fun fun areas of small business ownership. You're not going to want to miss it. Bought the Biz is a podcast for ETA entrepreneurs who've gone from searching for a business to actually running one. It tells the real story of what happens after the deal closes, the day-to-day operational, emotional, strategic, and leadership challenges that just don't show up in the highlight reels.
The show is story-driven and practical, sharing real experiences from operators along with clear actionable takeaways you can use in your own business today.
I'm Garth Fossano.
I'm Christi Loucks. Welcome to Bought the Biz.
Welcome back to another episode of Bought the Biz. Today, Christi and I, as we're heading into the holidays, we've been reflecting on some of the sort of funny things that appeared in our businesses when we stepped in. And, you know, one of the first ones that comes to both of our minds is the holiday policy. What did that look like? What did it not look like? What even was it when we got here? And You know, there are so many small things like this that are just sort of out of the blue. You would never expect if you have worked in corporate America and that is what you know, stepping into a small business is going to have many things that are just so different. So holidays, first of all, Christi, I think you said there was not even a defined policy. There was not even a list. Like the way holidays came up was tomorrow's a holiday, right?
For us, holiday, or it showed up like a week in advance on the shared Google Calendar. Now keep in mind, we had the business I acquired, we had a team in the Philippines, a team in India, some Europeans, and then, oh, and a Canadian, and then me in the US. So keeping track of these holidays was, I mean, it was insane, right? And I think the Philippines, they have a ridiculous amount of holidays. I can't remember the number, but it was far more than for sure the United States. So yeah, when I stepped in, it was like all of a sudden these calendar blocks would appear and the team would be like, yeah, we're gone, all of us for the next 3 days.
Ours was maybe a little like, I think I had at least a list of them, but they were not, there was no employee. We didn't have a list. I had a list, but my list was very, very short. It was like, there's a half day on Christmas Eve. I think you're off on Christmas Day, off on Thanksgiving Day, and you're off on, like, New Year's Day and New Year's— half day on New Year's Eve. And that was— and like July 4th and Labor Day. And that was it. There's nothing else. It was like, basically 5 holidays. The other thing that was really confusing for me and like I had to figure out answers for was, well, you know, we ran 7 days a week. So if you don't work on a Thursday, but you work, let's just make this up, like Tuesday, Wednesday, Friday, Saturday, you have a split shift week, like, and Thanksgiving is on a Thursday, like that's your weekend. So what happens? And like nowhere was that documented.
Really? So wait, what were people doing around time off and vacation, or like holidays, right? If there wasn't any, I mean, people taking like just President's Day off ever, or was it just like—
No, it was a workday. It was just work. Oh my gosh.
And how was morale?
You know, it was a call center, so I actually think Relative to call center morale, we did pretty well. And there were like a lot of fun things that were done around the sort of culture, I believe, you know, just because at the time that business was focused on selling dog training. Everyone at the company loved dogs, loved pets. Like, if your dog died, it was very acceptable for you not to show up to work like that day, the next day. Like if you had a—
Yeah.
Yeah. So there were some other things that were sort of, you know, we were more understanding of, but, but that was definitely a weird one around, around holidays and like, how do you answer these questions? And, you know, coming from corporate America, I'm like, wow, this is, this is actually like a risk. Like, what is the appropriate policy? And we're in multiple states. What is it for this state? What is it for that state? So that's the way I looked at it, whereas everyone else doesn't think about that at the company. There's like, oh, you know, this is— yeah, we work on President's Day.
Right, right. That's so interesting, the dog thing.
Oh yeah. Oh yeah.
I mean, not to knock it, like I was a wreck when my dog died, but still a dog dying over a president's status is, you know.
Oh yeah.
Oh, an interesting priority.
Yep. Yep. Here was another crazy one that I found. Um, and this was, I'm quite certain this was not written in the training materials, but in the new hire training that was sort of passed down in a way. New employees were being told that there was commute time because we all worked remotely. And so, you know, you don't have to commute. So like, think of commute time when you work from home as like a way of just getting ready for the workday, which actually makes a ton of sense. Yeah, but there were a couple subtle things slipped into that in the way that prior employees had been educated on it, you know, that you need to check your emails in your commute time to get ready for the workday, which actually sounds like you're starting work. And so an hourly place like that is— I don't think that that's allowed. I'm pretty confident that that's not allowed. So those are some just funny things that you're going to unsurface at an organization and have to, you know, bring in line with, you know, appropriate practices.
And what did people do when you changed it, assuming you changed it?
Yeah, I mean, I think because it wasn't formal, like there was no policy, it was just like, well, we need, you know, just don't train people this. Like, and, and it was sort of those are going to be phased it. Like, it was like, yeah, I just never talked about it. Like, I was like, that's crazy if that was what was happening. Like, we're not doing that. And I'm just never talking about that. And there's high enough turnover in a call center type business where You know, and I actually don't think people were following it. So it wasn't like needed to go back and do some sort of major retraining. But I think there are a lot of funny, I don't know, funny things in a small business relative to what we expect from corporate America. Like, or we did Deloitte, man. They had every policy to the nines, was done perfectly in compliance in every possible way. And you're going to step into a small business and it's, it's going to be wild. And yeah, yeah. So I think there's so many questions like this that you're going to need to think through and you're going to uncover things in this type of category for years, I imagine.
Yeah. I just remember finding like, I mean, we didn't have a ton. I don't remember there being a ton of policy like HR type policy. Now there was kind of like there was a baseline. There was enough to have at least a a foundation of like expectations. But I just found like little things that I just was, I was never expecting to manage, or, you know, I'd like kind of sit back and be like, do I really have to have this conversation right now? Like, I guess I do. But the, like, the one example I can think of is, so we had again like remote staff overseas, and so part of the part of what had been set up that I, you know, there are pros and cons to this as a topic, which we don't have to get into here, but like we really, we did a lot of time tracking and screen tracking, um, with a tool called Hubstaff. And essentially it's, you know, like a little Big Brother-y to make sure that everybody's actually doing their jobs and, um, not, you know, playing, uh, during work hours. Now, our team did work like US hours, so they were working overnight. Um, it wasn't like they were logging on when I was asleep and I had no idea what they were doing, or, you know, like, there was a level of visibility that I had no matter what because I could send them a, you know, message or whatever. But I did find out that there was a way that they could game the the system and still have screens up that Hubstaff was not recording. And so I found out that somebody was gaming, literally gaming during working hours, and his work product was also on the decline. So I had to have a conversation about like, you can't play video games at work, and I am going to keep recording you. And it's just one of those moments you're like, wow, this is a conversation that I'm having right now. It's fine, I'll have it. It's what's required, but I did not expect this.
I mean, I think that that's the thing you have to expect. I mean, talking to a bunch of searchers in more like blue collar, not remote, getting people to show up for work is a huge thing. And that was something we have seen in sort of your big brother comment reminded me of this one, but a common way to call out at our company when the call center model was to say, hey, you know, my power's out or my internet's out. And a lot of people would do that. And we would often ask like, hey, can you send us a screenshot of like the outage that's reported or, you know, whatever that is? And we would have people do that. But then we did have a manager who would like literally call their power company or their internet provider and check the status at their address and catch them. And Again, that's one of those things I'm like, that makes total sense. Like, that seems very reasonable, but also like, is that allowed? I don't even know. And it seems kind of— it does seem borderline invasive, but you're right. Like, that's the kind of checking that sort of needs to be done for your video game example, right?
Yeah. I remember too, just that you— again, I knew as we were going to start talking about this that I would think of more examples. So, but one of the things that I've Maybe, so maybe call it somewhere like 3 to 6 months after I acquired the business, I noticed— so we didn't have like a formal, um, like sick leave or like sick day policy or anything like that. It was just like, hey, if you're not feeling well, like, take the day. And I'm actually— I'm kind of fine with that with remote work. Like, it's— it doesn't really bother me. Um, but I started noticing that the team, the remote team, all of a sudden they would— there was a high increase in sick days that were being announced. Like, oh, you know, I'm sick. But every single one of them, Garth, was, I have a migraine. And I was like, there is no way my entire remote team is having all of these migraines across everybody. Like, it's not happening. So We're going to nip this in the bud and have a new policy. You can't keep doing this. You can't just put a Slack message that you have a migraine and then 2 days later your colleague says, "I have a migraine," and then 2 days later the next person says they have a migraine. I'm like, "This is not real. This is not real, you guys. I know it's not real. So stop playing me." We now have a policy.
Yeah. I think it's actually one of these big questions that I have is, I love sort of the informal, like, let's be good people version of this. And I honestly genuinely sort of hate a lot of the big corporate feel that, you know, you would get at Deloitte. And so I actually wanted to be like, oh, you have a migraine? No big deal. Great. Like, go take care of it. Like, that's the way we want it to be. And then unfortunately, we sort of like get burned a couple of times and you move into this policy sort of version. And, you know, as our company has grown, had teammates tell us like, it doesn't feel like a family company anymore sometimes. And like, you know, we— it's because we've been burned enough or, you know, we're trying to build the processes for scale and, and, you know, that is working. I do wish it could also be a family company, but sometimes I have this like push-pull emotional feeling that like I really do miss sort of the small little business type model as well. But I also know that that, that's like not why we got into this too. Yeah.
Just the less formal, human to human.
Yeah, absolutely.
I definitely too, I have learned, I don't think it's a flaw, but I do have to be aware of it. I am very trusting and like very, I assume good intent right out the gate. So if someone tells me they have a migraine, I'm like, well, I've had migraines before. I know how terrible that is. You know, go rest. But yeah, there does hit a point where you're like, but then I also feel like I'm a little bit being taken advantage of potentially here as the new owner. And then I get— my guard goes up, which I don't like that either. So I think what's the good thing about policy is like, it's just, it's factual, it's black and white. It's a roadmap and so you just eliminate the ambiguity out of some of those scenarios. So it's like, even though I know I would like to trust people when they really have, if they say they have a migraine, it makes it way easier when there's just a policy.
I agree. And it sort of get, you will basically get fatigued on these types of questions where you're answering the same thing over and over and trying to handle each one in a one-off way, that will become incredibly tiresome and a big burden. And I think that's actually a really interesting point. And I think maybe a cool question to ask of you is, you know, regardless of whether or not you have a policy, these types of things are going to come up in a small business for all the ETAs and searchers out there. I think you need to acknowledge that and accept that. And, you know, I was just making this comparison to Deloitte and one of the things that I question a bunch is like, you know, now you end up spending your time working on these kinds of problems instead of, you know, at Deloitte, big strategic problems where, you know, because of all the policies and formality, like, no time is spent on what we just talked about. And so in your own personal career growth, like, you know, as you think about how you spent your time over the past couple years, do you think it's a— this is a good learning experience that has helped you develop, or do you sort of wish you were getting to spend and being able to be more focused on those higher value sort of tasks? Or is— I totally misled that with the word higher value. That was, that was way too leading. Yeah, so, so please strike that from the record.
I— here's what I'll say. No, I hate writing policy. I hate— well, I'm very glad that ChatGPT is where it is today because it's definitely a good starting point, uh, relative to what I had a few years ago even. Um, No, I mean, of course, like, I don't, I don't like doing that stuff. I would rather spend my time working on the business, not in the minutia like that. But I will say this, you know, with like, with one of our businesses right now, I'm kind of stepping in just to help, you know, build a lot of like structure and process that we, that we need, just because I have the experience. I kind of know what to build, so Um, you know, we're, we're allocating some of those tasks over to me. And while they are tedious and, um, quite frankly annoying in many cases, it— I, I like— I am learning to really value what they bring to the business. And like, one of my biggest— I, I really like making order out of chaos. So when I see chaos in even the minute details, it's like, I want to fix that. And while I also have this huge list of strategic things that I need to get to, I know how important it is. And I've learned how important it is to have that structure and have those like guardrails in place. So when I'm doing it, as I'm, you know, drudging through it, sometimes it's like, no, this, I can see where this leads us in the big picture. And that, I think, I don't know, that's my take. Like, yes, I don't like it, or no, I don't like it. Yes, I need to do it. And I also know why I need to do it.
Yeah, I think that makes sense to me. And I think if I were to answer the same question, I would say, you know, having worked at Deloitte on the similar type of problems that I work on in my small business, you know, at Deloitte, I never got the deep understanding at the ground level. And while it was always much more 30,000-foot view, strategic, and, you know, the execution details much further down were, you know, let's say this, like overlooked. And I think that there is so much learning to be had being at that more tactical level, and it gives you a much deeper understanding so that you can be more effective at the 30,000-foot strategic view. And so I think the way I would say it is it's actually just part of the process. And, you know, the example I think of, I worked for a CEO who was an operating partner for a private equity company, and I worked in that portfolio company with him. And he and I met at the office at like 6 a.m. every day for a month to work on a particular board deck and I got to listen into this stuff, see it, hear it. And he didn't really use much of it. And I was like, afterwards I was like, Frank, what the heck? I spent so much time with you on this. And then we basically wasn't even used. And, and his comment to me was like, that was the process. Like by going through that process, we got so good at this that we didn't need it. But if we didn't go through that process, it would've been a disaster. And that was sort of an eye-opening moment. So I think in a very similar way, You know, getting in at this level is very important for the process and for the learnings that you're going to take and actually is a big driver of the value too.
I found it's like to that point, like I found it, I'm like insecure if I don't know the, the nitty gritty, like I'm insecure, I get insecure about my ability to lead and like run the company if I don't know how things are done on a very granular level. Maybe that's a control thing. Like, that could be a personality flaw, but I think it's a control thing. It is like, because I'm like, I, in order to make this as good as I possibly can, in order to optimize this, whatever it is or this is, I need to know how it's done and I need to do it myself so that I understand the nitty-gritty that I need to then improve on.
That is a whole nother topic that we should address, I think. I mean, we're gonna put it—
I think we should be insecure business owners.
Um, that would be another topic, but I'm thinking of sort of the right attitude and approach to leadership so that your business can scale. I think you're right. Like when you step into these small businesses and especially when you have a PG, like the level of detail and depth that you just described, I think is something everyone needs to have. And then as you get more comfortable with what's going on and as you move up, like you shouldn't go back down to those details, right? To hire somebody to run those details.
Right.
And I think that that's sort of part of the scaling trajectory and process. And I just sort of feel like from my own personal experience that when you have a PG, no one is going to stop you from getting into that level of detail so that you have that full confidence.
Yeah, because I don't trust myself to make the right decisions if I don't know the details, because then I could overlook something, right? Or like I could not fully understand the nuances of a situation or a process or a workflow or, you know, whatever it may be. So like, I'm not sure that my— I'm not sure that my diving into the details comes from like a healthy place, but I'm not sure either. But I think that it's like— but I think it's actually ultimately good, I think, to get in there.
Yeah, at the right time, in the right place.
Yeah. And then once I have my arms around it, it's like, okay, now I actually feel like I could even go write job description because I know the freaking role. Like, I've done this, I get it. So it's, yeah, I think that's, yeah, it's an interesting dynamic.
Perfect. Amazing. Any other weird things?
Yeah, I mean, the whole thing is weird. Business ownership is weird.
Yeah, that's a good way to describe it. Perfect.
All right, we're gonna wrap it up on that.
Yeah, have a great holiday, everybody.
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