The real dichotomy of founder freedom

In this candid, informal vlog, Matthew Kelly reflects on the paradoxical nature of founder freedom. He describes his routine of evening walks in Dubai, during which he talks to AI tools like ChatGPT and Claude as a form of self‑therapy, and reveals how his undiagnosed ADHD has shaped his risk‑taking, impulsivity, and "grass is greener" mindset. Kelly explains how moving from central London to Dubai—changing time zones, climate, and daily routines—dramatically improved his mental clarity and creative output, underscoring the profound impact of physical environment on a founder’s performance. He then examines the downside of unrestricted location and time freedom, noting that it can foster loneliness, a lack of human connection, and a tendency to over‑indulge in short‑term dopamine hits. Kelly critiques his past avoidance of office spaces and remote‑only work, acknowledging that insufficient in‑person interaction hindered both personal wellbeing and business scaling. He proposes concrete solutions: intentionally designing work environments, establishing shared offices or coworking spaces, and making a conscious effort to engage with other founders and friends in person. Throughout, he balances personal anecdotes with broader observations about founder culture, ultimately urging listeners to recognize and mitigate the hidden costs of excessive freedom.
Chapters
So I feel like I always talk about the same shit on this YouTube, um, and I've also recently got into, well, a habit slash a routine of evening walks. Now I'm in Dubai, it's like very hot. Well, people say it's that hot, I actually don't find it that bad, but for me I was doing evening walks of time zones. I'm always working until like 11 PM and then I feel like I need to go for a walk for like an hour before bed. And then often during that time it's probably like a really Black Mirror-esque habit and probably just mega like obcessive founder behavior, but I tend to like speak to fucking ChatGPT or Claude about like topics that are on my mind. And I don't know, it's probably like super weird to admit that, but it's almost like never really got therapy for many things, but speaking to AI has always helped with that. Um, one topic that I was just randomly rambling about the other night, I was actually speaking to, well, my mate about it as well, to be fair. I do speak to humans as well as AI, but it's probably AI more these days, which is kind of part of the problem. Um, and I feel like the problem with me is I spoke, I spoke in a previous video about being mega ADHD and stuff, and I genuinely mean that. Like, that in hindsight, it's probably taken me fucking, I don't know, 10 years to even like realize the intensity of that in hindsight and how it's affected my business and relationships and all this. And I think a lot of founders are that as well, you know. It makes you very high-risk, risk-tolerant in a, you know, positive way, but quite a crazy way to a lot of people. I think it can make you quite impulsive. Um, I think like the net outcome of all that for me is I very much have a grass is greener— not always, but I recognize that myself now more than ever. I tend to have a grass is greener approach to a lot of things. Like example, like I moved from London to Dubai. I spent 7 years in London, central London, and I liked it at the time. I probably almost like— I'm more fond of it in hindsight, right, with like rose-tinted lenses. And I moved to Dubai because a lot of my friends had moved. I wanted to live more in the sun. I liked the time zone because I wanted to have more of a healthy routine in terms of being able to train in the morning. And like, all these things might sound trivial, but for me that all resulted in having a clearer head to do better creative work specifically, which is more of my role now. And also, actually, I felt it was best for the business because I was not in a good headspace the past year I was in London, as in the final year particularly, um, which came from a genetic baseline. But like, environment's a massive one for me. Like, I was living in the wrong place. I left London originally like September 2024 and then came back and like it was just so chaotic. I didn't consider the, the vast implication and impact of like having a good environment, which I've spoken about a lot before, and it's so obvious and even to like, you know, normal people. But for me, I kind of— I think I really, really thrive a lot more in the right environment. And it's never going to be perfect, but for me, like, you know, like I said, time zone, weather, people around you, even just little things like having a nice office and, and all this. And I didn't have that in the last 6 months when I lived in London. I was literally living like an Airbnb, it was crazy. Because partly because of like ultimately ADHD tendencies. And anyway, my point is I've created a lot of freedom for myself, as a lot of founders do, and like financially to a degree, but also probably more prominently, like just location and time in the sense that I can work from anywhere, and a lot of people can, um, but For me, that has always meant like location— you almost by default have like, not literally, but it feels like unlimited options. Then when you're not self-restrained and like, okay, I have to live here to do this job because my office is here, combined with like quite erratic, very creative but sometimes chaotic mind, um, that can result in I think doing things that are not necessarily best for actually best for me overall because I'm chasing like a short-term dopamine hit in some ways. And I recognize this is definitely like a lot of ADHD stuff, and I almost kind of want to use that as an excuse to a lot of people that probably thought I was being rude to them, whatever, but including my girlfriend. But, um, I think being like ADHD— and I'm not just rambling about ADHD— but like being entrepreneurial and having those tendencies to be less rigid and again probably just quite chaotic I think it's great for building a brand, but I think at scale it can be sometimes harder to build a business. And I think that there are two distinctions. I still think it's net good as a founder, and most founders are that. But anyway, coming back to my point, um, as a result of like too much choice through like self-inflicted freedom, if you will, which actually has a downside. And I've always had a lot of freedom, certainly location-wise and time-wise. I've always worked myself, and even when things weren't going that well, I still had like location, time freedom, right? And there's a bit more financial freedom now, but you know, there's obviously levels to that. But anyway, generally financially speaking, I've got a good amount of freedom. And then I moved to Dubai, and this was also true in London, by the way, because like, because I didn't have to go to the office. We never got an office, and then we did get an office, and then I didn't quite invest in it because I didn't— I thought maybe I want an office that's somewhere else, or like a bigger space. And before you know it, I've kind of like spent 2 years in a routine that was like, yeah, it was good, but I probably lacked like, honestly, like a level of human interaction that in hindsight would have been nicer. And I undervalued that myself because habitually, for the, I don't know, first 6 years of my entrepreneurial career before that, I'd always just worked fully remotely on a laptop when I had no team. And then when I got a team, I was like, oh, I don't really want to be in the office because I'm not used to that. Um, but actually not being ever around people, especially the team in the business, probably did make a lot of that a bit harder. And that's a whole other, you know, conversation around office versus remote. I think there's plenty of pros and cons to both.. But for me, I basically was always like trying to— always thinking probably too much about, oh, this isn't quite right, whatever, that I didn't just sometimes lean into it and just do the fucking thing. And actually, that resulted in me probably just feeling quite lonely. And that's probably kind of what I'm saying in this video, especially as a solo founder. I've got a shitload of founder friends, but I think they probably all ironically probably feel this to a degree in their own little bubbles, and then no one really talks about it because you're guys and I'm not even saying it as like being a little bitch or whatever. I'm more just saying it's definitely something I've noticed, and probably even more so since like moved to Dubai, and that was great, and I live in a lovely place, and my routine is really nice. But now, like, the irony is, and I have loads of founder friends that even live in like— not loads, you know, a handful that live within about a mile of me. There's two in fact that literally live in my neighborhood, one of which— well, I'm not going to say their name, but in case they don't want me to say their name, but own two big brands that I've probably spoken about before here, and you probably know if you're in the space, but you definitely know. So like, it's a great place, and for me, on paper, it ticked all the boxes. And I guess what I'm saying is you can go to a sunnier place, but it doesn't solve the core problem. And the core problem for me was probably just not having enough like human connection, ironically. And that's coming from someone that didn't want to be in the office and moved away from the office with The problem was that setup wasn't right for me. So because it didn't feel quite right, I never really invested in it. But then I haven't also taken the time yet to design my environment to the correct degree in my new place that is definitely better foundationally for me. But what it's missing is ironically what I had in London but never really used. Wasn't fully set up perfectly 'cause like, whatever, we had an office but weren't really like fully using it and the environment wasn't like, I didn't really invest in that environment like emotionally or physically, so it was never that good for me personally. Um, and that still exists and that's fine. Like, our London team is there, but half our team's like fully remote anyway, and we're doing more shoots out here and stuff. Um, I guess I'm just rambling as normal, but my point is like, I've kind of— I feel like a lot of fans relate to this. You almost like, through success to a degree, having the freedom and stuff, you're then at more risk actually compared to most people. Like my brother, for example, who's an easy, easy example. I don't think he watches this, but he wouldn't mind me saying it. You know, he has a normal job, and I think he's far happier than me because he has more enforced routine, more enforced structure with people and locations. Whereas for me, it's like I could quite literally just not leave my room for 3 months, like my home office, right? I don't mean like literally, but, you know, go to the gym, go home, and that sometimes feels like the routine. Often that is the most productive when I'm working on certain stuff. But then I kind of think, is it all about productivity? And actually, B, even if it is, is that the most productive versus, I don't know, being 3 days where it's more in person? Actually, the sort of stuff I'm doing now, for the first time ever, like, it probably would be more productive to be more in person, whether it's in a studio like this or in a paddle court shoot like we did the other day that was with more people. Um, and then I feel like a bit of a hypocrite because I've like kind of checked out indirectly— not checked out, but self-selected out of some of the more in-person stuff that my own business does have, i.e., the office presence and so on. But again, that wasn't the right environment for me personally at that time, but I haven't rebuilt it elsewhere. And that's purely out of probably habit in a way. And also just like always thinking grass is greener, 'cause now I'm here a bit and it's like, ah, should I be in the office in London? But then actually I went there for a month and it's fine, but it's just not for me. I prefer having a bit more freedom and not doing the central London commute and whatever. I say it's just funny because you basically create your own loneliness in pursuit of productivity. But then I kind of get to the point where I'm like, okay, I'm actually being really fucking productive, but do I enjoy only seeing my girlfriend Monday to Friday? I don't know, probably not. And she wouldn't mind me saying that because she probably feels the same about me because she also works from home a lot of times. Um, and yeah, it's almost like I've chased freedom, but then you kind of lack I guess, like, without sounding cringe, a bit of that, like, community and belonging side. Because of, like, changing countries, and you can absolutely build that. And ironically, I have a much— I have a great network. I'm very fortunate to have that, but a lot of it's online, and I've— I just don't make the effort to do it in person. Um, and that's the same for a lot of founders. And for me, there's a lot of guilt almost attached to, like, being away from my desk, which sounds ridiculous, but I think that's, like, a very limiting belief, but it's very true. Because in the past when I thought I got a bit lazy, I got distracted or whatever, and for me I associate that with the beginning of my last business failing, which was true but might have been a correlation, not causation, right? Um, so yeah, anyway, I think the fix ultimately is acknowledging it and just fucking making an effort to get around more people. And like, even me and a few founder mates now thinking about why don't we just get like a shared office where, okay, some of us have like one or two team members here like I do already, like our finance guys here One of our creative people are here. Someone else is maybe moving out. So it's not like there's no one around. It's not like there's no business case to have a presence here, but probably because it's only a few people, you come, ah, do we need it, whatever? Do we just go to a cowork space? But even that I haven't been doing because it's so efficient in my home office. And I even set up a podcast studio on the top floor of our villa that we're renting, and literally I've never used it. So I come to this place instead because I'd rather get out of the house. 'cause it gives you more accountability as well. So yeah, I think the solution is just getting around more people and realizing that you can have any setup and you can have the freedom and that's great. And for me, that brings out more creativity and I feel healthier and whatever, and that's all good. But there are always going to be certain parts that lack unless you design the environment to plug those gaps basically. And I just haven't done that yet. And even it's like just as simple as fucking like, hanging out with other founders. It sounds like ridiculous because a lot of it's just online. Like, you know, you've got a lot of internet friends on Twitter, especially YouTube, Instagram. And I could probably put one tweet out and meet 10 people tomorrow in Dubai, like for sure. Maybe 50 people if I was in London. Um, I just don't, and it's probably a bad habit. And then you realize, oh shit, I've not actually made like any new friends in like the past 2 years. And my core group of friends is very solid, and I'm at that age where it's probably less and less asked, but It's definitely something I'm aware of, and you can't— the main question is like, okay, like, let's assume that the business keeps growing and is very successful, which I obviously want it to be, but like, even then, okay, let's assume it does that, but you spent the next 5 years working almost entirely in your spare room office. Is that really going to be fulfilling? And that's where I'm a bit like, okay, probably, you know, grass is greener, rose tinted. I look at brands that have like the sick office set up and think, I actually fucking want that now. The irony is I had a bit of that and I kind of ran away from it because it wasn't the right setup for me for many reasons, and that's fine. But I think we can have both. So yeah, that's basically it. I could ramble about this all day, but it's something I've been thinking about a lot, and it's just like a funny irony that the freedom you create, it almost becomes like a loneliness prison if you don't proactively do something about it. And I haven't been proactively doing something about it, but I have been thinking about it and I'm talking about it, and I should probably actually just go and do the things I'm talking about doing to fix it, which I am now doing. So yeah, this one came from like a 1-hour walk thought, but I thought I'd share it because I think it's pretty relatable to a lot of people. And yeah, if anyone's down to get like a massive fucking studio office space in Dubai and has a similar business, then maybe drop me a DM. But anyway, I'll wrap it up there on this one. Let me know if you can relate, let me know thoughts in the comments. Otherwise Yeah, watch something else, subscribe to the pod, and I'll catch you in the next one. Cheers.










