The messy middle part of building a scaleup brand past 20 employees - everything is hard - Ep 105

A solo episode (Ep.105) monologue by the creator Matthew Kelly reflecting on the challenges of leading a scaleup (~16 full-time employees plus agencies). Topics include founder role-shift from doing→managing, delegation guilt, cognitive load of oversight, reclaiming high-leverage creative work (product/brand/content), and operational habits (equipment, steps, chair, work hours). The speaker plans to audit time use and redefine his role to focus on high-leverage and enjoyable tasks.
Chapters
Yo. So back with episode 105 of Documenting the journey, which is crazy. I don't know there's that many series on YouTube or podcasts where people that get all views have done 105 episodes, but I'll probably keep doing 500 episodes at this point, actually. Hopefully we don't take 500 episodes to get to where I want to be, to the point where I probably won't make YouTube videos, but maybe at that point I'll just do them for fun. Anyway, I'm quite enjoying this Selena gomezi esque or just pop star esque microphone setup. I think it'd be good for bringing the pod back. I actually bought this new new shure microphone that you can't see on screen, which is what I used a few videos ago. And I just. Classic case of like man mats and man gadget stuff. Just buying stuff that's super complicated that you don't have to use like an XLR thing into this processor. And I realized I could have just got two of these anyway. So I can put this on here for like team calls and shit. And every time I do a team call, I sound like I'm on a podcast, which is quite interesting. I can also just hold it, which I think is more casual. Also, quick note, I've probably like optimized the fuck out of my like working setup. This is a temporary place. I'm in an Airbnb right now, but studio display, nice microphone, nice boom arm, which makes that stuff way easier. Big proponent on office chairs. I get a bad back. So I had a Herman Miller in the office. I've now got another Herman Miller. This is the Herman Miller Aeron remastered size B. I used to have a size C. Anyone that's a fucking chair snob will know what that is. But yeah, I'm going off on a tangent already, but people that like always say, oh, why would you spend so much on a chair? Trust me, if you're spending like 12 hours a day on a chair, right? Or at least like 6 to 12 hours a day depending on what you're doing. I get a bad back from years of rowing. I think I tweeted debodevs f ed. Still pretty fucked now actually. But yeah, having a good chair really helps. So don't know if you can see this is my Herman Miller Aeron. Anyway, that maybe that's a separate video on optimizing office setup. Something I've been thinking about last night. I've got into this new habit recently of going for like minimum 10 to 15,000 steps a day, which is helping me lose some weight, to be fair, if anyone can notice that. And during those walks I. This might be super autistic fandom mode, but maybe it's relatable. During those walks I speak to ChatGPT about things that are on my mind. I also speak to humans about that sometimes, but more often than not, at least on my walks, it's with ChatGPT which can be a great therapist in many ways. One thing I was speaking about last night that I've kind of been thinking about overnight and I thought, fuck it, I'll just drop on here and make a video speaking about it, which is the start of the pod now it seems is like the messy middle of not being, you know, super early stage startup, but also not being like fully fucking optimized with systems team. A perfect team for everything. And you know, stepping back as founder and doing just what I want to do fundamentally what what I mean by that is, you know, I used to do everything as you do and there's a lot of challenges with that and then, you know, but you're obviously ultimately responsible for everything and you do everything yourself and then you obviously hire a team, blah blah, blah blah. And I've been through that in a previous video, so I don't want to go through every step. But like now where I'm at is we have a great team and people doing essentially every key function of the business. Obviously I'm still involved but like largely my role is annoyingly right now at least kind of gone from doing to managing. And like I touched on in the previous video, some of that's good but in other areas I want to go from managing to actually just doing again. And I still do do, but the problem is because I'm managing a lot of things, both like preparing, planning one on ones, you know, like assessing things a lot of the time and feeling like I have to get involved in a lot in a lot of stuff. I end up then not really doing a lot of the stuff I want to be doing I actually should be doing that would also actually make more sense for the business, I. E. Like product, brand, you know, new market growth stuff, stuff like that, stuff that will really move the needle. And I told myself the last year is what I should only focus on. And then in a way it feels like since hiring loads of people, well, not loads of people, we're a team of like 16 full time now plus agencies and so on. And you think, oh, it gets a point where I don't have to work anymore and I got loads of time back and all this. But then just new work multiplies and expands to fit the space that was created by delegating something to someone else. So like, even when we hire David or Maryland, it's been a massive game changer in many areas. But then it's also just giving me time to then start stressing about something else. Right. And then I'm trying to get better at being, I guess, a manager. I mean, I kind of said I don't necessarily see myself being a CEO as much I kind of hate that term. I technically am that right now. Don't necessarily see myself being that forever. I think I enjoy more the creative zero to one stuff. I kind of. I don't just mean zero to one in the business. I mean zero to one in any part of the business, I. E. A new country, a new product, whatever. No matter what level the business already at. I'm naturally drawn to that stuff far more than I am like a fucking performance management review or something. Or like anything to do with HR if I'm completely honest. You do need that, but I'm not the guy that enjoys that and therefore probably shouldn't be doing it. And I don't do most of that anyway. But yeah, I'm kind of in this paradox where I've hired people to free myself up, which I have and have freed myself up. But then you still end up wanting to have input in a lot of areas. Certainly the areas that are most keen on, like I said, like product brand growth. But even those areas have team members for. But then I feel like obviously need to guide them and give feedback and be involved. And I obviously do want to be involved as I should. But basically what I'm saying is there's probably more work now than there was when it was just me doing everything in many ways. And there's more cognitive load as well because I'm thinking about other things like, well, you know, how do I communicate this or how do I give feedback in this without, you know, coming across wrong? Or how can I assess a situation that I might lack context on because I'm not in the details of it all the time, etc. Etc. For example, like we had some massive delays with like a new website thing we're doing and my instinct was like, oh well, I don't know, we've obviously done something wrong there. But then, you know, dug into the details and it was XYZ reason to an agency, freelancer, something broke, whatever. But because I'm not in the weeds all the time on every part of the business as I can't be, you know, I don't know that. So you end up feeling like you sometimes don't know as much about the business as you used to. At least like in like the business as usual trenches stuff anyway. So yeah, it's just kind of a big reflection of like you think you're gonna have loads of time back to do all like the strategy and brand and like vision stuff. And I should do some of that. Some of it's complete fluff by the way, but I often think strategy is another word for procrastination. But it's also true. Coming back to my previous video, like brand drift and so on, had I spent more time on this, which I'm now trying to do at the weekends and like last night, Friday night I spent loads of time, or a few hours at least, basically trying to draw a line under where we've got to on like the brand drift and trying to reset it, which I'm going to present back to the team next week. And maybe it lands, maybe it doesn't, but either way I think we need to do it. We probably will in 2026. So yeah, basically I got no fucking time to do the stuff that I think is high leverage because I'm still probably too involved in a lot of other stuff. And that's partly because I'm just used to being super involved. Partly because some like functions of the business and team are newer and I want to like set the tone and be involved. And then also partly because I just, you know, have the founder guilt of if I'm not involved, like not. It's not gonna, not that it's not gonna get done properly because it will and often does and usually does. But like the guilt of, oh, if I'm not involved, I can't be working hard enough. Right. And then I also find myself pre glued to my screen now actually more than ever. Like, I mean today it's Saturday, I'm probably going to be sat here working all day. I mean, that's fine. I'm like a founder. I'm in that stage and that's my duty in many ways. But in other ways it's sometimes not that productive because I find myself working till, you know, 11pm and my desk from like 8am to 11pm obviously with breaks and gym and so on. But like broadly like that every day is probably, I don't know, 10 to 12 hours at my desk actively every day because it just feels like, there's so much to do, and it's not necessarily stuff that needs doing now, but it's stuff that if I don't do it now, it will ultimately be done at a later date. And if I could do it now, that should, in theory, move the business forward, right? So there's always that kind of guilt of, I've done the stuff I probably need to do today, but I could do more because we want to grow faster, we want to get there. So therefore I'll just sit at my fucking desk for the next, like, the whole weekend, basically, often. And to be honest, that's been true for me for, like, the past eight years in many ways, and probably is even more now because the business is at a stage where, like, we've built this machine and it's, you know, it's obviously a lot stronger than it was two, three years ago, even a year ago. But I also feel way more pressure and way more, like, opportunity costs if I'm not doing stuff. And also the stakes are higher if I massively fuck up, like a month or a quarter or, you know, don't deliver on the things I said I'm going to do anyway. I'm going full ramble mode, which is me after two coffees. Not rainbow dust. I haven't shipped any here yet, annoyingly. Two coffees and. Yeah. So I don't know. Don't know if this is relatable. Basically, what I think I need to do is probably, like, a lot of things just fucking audit. Where I'm spending the time, where is actually a good use of time for me personally, but also the business, most importantly. And then, like, ruthlessly draw a line on the things that I shouldn't be getting involved in even if I want to. And it comes down to focus, right? Focus is saying no to you want to do as well as stuff you don't want to do. That's the real focus. It's easy to not do the stuff you don't want to do. I probably need to literally, like, redefine my role in writing, which I have done recently alongside David or md, to kind of split the roles, but there's probably more that needs to be cut out of there. And also I'm just drifting into stuff that isn't in that because of the reasons I said before, like founder obsession and OCD and paranoia and all that. So, yeah, it's just a reflection. Like, I feel like in the pursuit of trying to be really effective, I end up doing things that aren't that effective. Because I think I need to be involved in everything. And actually, I definitely fucking don't. And I shouldn't be. In fact, I think it comes down to clarity on the vision, clarity on everyone's role, including mine. Trusting the team and then just focusing on high leverage stuff. And actually also stuff that I enjoy more because stuff that you find yourself naturally doing. Like, what are the things you would do if money wasn't a thing? Right. And there was no pressure. And naturally they're the things you're probably better at. And I know some of those things for me, some are probably on the edge and then you should probably do more of those because you're better at them. And if you're better at them, you'll probably get better results and you'll want to work harder at them. Right. I'm trying to avoid doing things I hate in the business. There's obviously certain things still, but a lot of that has been delegated elsewhere. So. Yeah, and then I'm trying to probably lean more into content and I kind of got into this mindset I shouldn't be any. In any brand content. Maybe the podcast is a waste of time and all this, but now I think that's kind of like potentially one of the highest leverage things for me and the business, potentially. So there's more I want to do there. But then it's almost like, because I'm so used to being at my desk for the past eight years at a screen, it's kind of this weird feeling of like, oh, I can't possibly, like be out filming content for a day or week, for example, because that's not high leverage or like, I don't. That doesn't feel like hard work enough. But it's complete because that could be way higher leverage than me sat staring at a document for three hours that actually I could just, you know, put to one side and do something else Anyway. Yeah, this is probably relatable. I feel like I get stuck in this pattern of I need to just grind until I make it, you know, until the business gets to where I want it to be. But actually that's not always that productive. So, yeah, I'm just documenting this process for me because I'm in this kind of awkward middle stage. I feel like it's probably like the middle in terms of, like the life cycle of the business, you know, broadly in terms of my involvement. And yeah, in the spirit of the pod, I do just talk about that's happening. So this is one of those things. Anyway, I'll wrap it up there. Let me know if it's relatable. Let me know anything you want to see. In particular, let me know below if you actually want to see the actual pod, come back with guests. I have this vision of doing like a round table with like, seven people in like, a pink actual professional setup, which is probably more admin than I think. But yeah, let me know anything you want to see. Anything you don't want to see. Whatever on the pod, I'll keep making it anyway. But be cool to lean into what people actually want to see a bit more as well. And as always, appreciate you watching. Subscribe to the pod and I'll catch you in a bit. Peace.










