Chris Kirkland on Running TokyoCheapo.com, Living In Japan, and Lessons On Entrepreneurship & Living Nomadically

[01:42] Paul: Today I'm talking with Chris Kirkland, a bootstrapped entrepreneur who's been living nomadically since 2006. He's also a headstand enthusiast and a founder of several web businesses including artweb.com and tokyocheapo.com. .com. Welcome to the podcast, Chris.

[02:02] Chris Kirkland: Thanks for having me, Paul. Pleasure to be here.

[02:05] Paul: Excited to talk to you today. I thought, so I have a number of questions. I thought an interesting place to start, especially given the name of one of your websites, Tokyo Cheapo, would be to talk about money. You said you're a bootstrapped entrepreneur. You also write about cheap things to do in Tokyo and several other cities now. On one of your posts, you wrote something about money, and you wrote, we don't require vast quantities of cash to be happy.

How did you come to that conclusion?

[02:41] Chris Kirkland: Well, I think there's a fairly strong scientific consensus around that. You know, it's, it's, uh, there's no secret that beyond a certain point of money, more money doesn't make you any more happy. Uh, below a certain point you know, it's difficult and you are unhappy to some extent. So basically having enough money and having way more, there's not as big a change as you would imagine. So yeah, I don't think I've got any kind of novel insight on that. It's just, it's basically a scientific fact.

[03:14] Paul: And how have you thought about that since working as a bootstrapped entrepreneur and how you think about money? Did that change from what you were doing earlier in your career?

[03:25] Chris Kirkland: Yeah, but, um, there's several stages to this. Firstly, I think, um, one of the things being a bootstrapped entrepreneur gives you is freedom. And, you know, that's almost something that money can't pay for, you— money can't buy. Like, um, a lot of people who take this path do it because they want to be their own boss, they want to be in control of their time, and it's exhilarating. It's tough sometimes, but, you know, most of us wouldn't trade it for doing, you know, the corporate, uh, treadmill type affair. So there's that sense of doing it for the freedom.

Then I suppose as your path of life changes, your kind of budget changes. And I must confess, nowadays, like, I'm not quite as much of a cheapo as I was, um, kind of at the beginning. But, you know, I'm still living in a small apartment with few possessions. So in a sense, I've still kind of got that cheapo ethos. So, um, I guess another factor, if you, you know, if you have family, if you have dependents, then that's obviously going to change what that sort of comfortable range of income is. Um, but at a certain point, if you're kind of browsing through Ferrari photos thinking about buying a car, then you've got to sort of ask yourself, okay, Is this something that I really need?

There's this point at which you realize, "Okay, I shouldn't need to worry about money anymore." I think that's a fairly low bar.

[04:52] Paul: Right. Yeah, I think a lot of self-employed people I talk to, entrepreneurs, freelancers, there's often an inverse trade-off at the beginning when you're either leaving a default path. You actually find you can get more freedom by trying to make less and creating more time. Um, which perhaps is the only viable option to keep The Pathless Path going, right? To actually create those Tokyo Teabows or the ArtWeb.com. Did you find something similar at the beginning of the journey?

[05:22] Chris Kirkland: Absolutely. I mean, I was absolutely broke when I started ArtWeb.com. It was a, you know, I had no choice but to like try something. I, you know, I just got rid of my best paying client who, uh, or one of my big paying clients, we sort of had a falling out and suddenly I had to do something. And also at the time, um, I don't know if it's just the exact timeline, but there was a point at which I kind of moved out my house and I was actually living in my office. And I think I was at my happiest because I just reduced my overhead so low.

I wasn't making a lot, but I wasn't spending a lot. And I was just like, I just felt so free.

[06:04] Paul: Yeah. Did that give you a sense of power? Just knowing, oh crap, I can actually just radically reduce the expenses if I need to at any time.

[06:14] Chris Kirkland: Absolutely. That kind of stoicism of realizing that you can basically live sort of sleeping rough on the floor with a small blanket, you know, having baths in the sea. I didn't have a bath in my office, so I just go to the sea and like wash in the cold water. Sometimes I'd go to a friend's house and use their shower, but I just loved it. I mean, I didn't stay in that situation for more than a few months, but I just found it really empowering, really realizing that I just didn't need much.

[06:42] Paul: That's fascinating. Do you think entrepreneurship, people are most drawn to it because those type of experiences almost come as part of it or forced, and it's hard to kind of create those exercises for yourself on your own?

[06:57] Chris Kirkland: I think people are drawn to it for different reasons. I always think of myself as being quite risk-averse, although my life probably contradicts that. But, uh, what drew me in was the freedom. But, you know, you definitely get some people who are just, um, you know, they like the roller coaster ride. That's just what they are familiar and comfortable with.

[07:18] Paul: So you ended up in Japan after taking a trip there. And basically deciding to not board the return flight back. First, I'd love to hear, like, I hear this from so many people in Asia. Why are so many people, uh, staying in Asia and not boarding their return flights back?

[07:38] Chris Kirkland: Well, I would say Japan is a different place to Asia.

[07:42] Paul: That's true. Yeah, it's a, it's a high-wage, um, high-wage place as well.

[07:47] Chris Kirkland: Yeah, I mean, it's It's not the obvious place to go when you're doing the kind of location, um, location-independent sort of lifestyle arbitrage because it's not that cheap to be here. Um, but it's, um, I mean, in my particular case, I was just sort of wanted to try somewhere new. And, um, coming from the West, you can't get more different than Japan, really. It's, uh, it's a fascinating place. Um, in many senses it's a very comfortable place. It's very kind of, you know, the trains run on time, it's spotlessly clean.

So, um, I think for a certain type of people it's very alluring.

[08:24] Paul: Yeah, that definitely resonates. I think Taipei has a similar, uh, vibe. It's, it's still one of these places that's very, uh, homogeneous like Japan, and the culture is very different. Um, but also has all the things you need to kind of, uh, live similar to cities, uh, all over the world.

[08:45] Chris Kirkland: Yeah, certainly. I mean, I've spent time in Southeast Asia, other places in Europe, even briefly in India. I couldn't see myself like, you know, maybe I would miss a flight out of Thailand, but I don't think I would stay there for 10 years. You know, I'd like, okay, I want to go back somewhere where it's clean. So yeah, but maybe some people in Southeast Asia, they get hooked on the nice weather and the cheap food. So it's probably down to sort of personal preferences.

[09:16] Paul: So what shifted from, okay, I'm going here for a trip, to, okay, I'm gonna stay here?

[09:23] Chris Kirkland: Well, the backstory for Japan was, um, it was already in the back of my mind that I wanted to move to Japan. So this was meant to be like a sort of reconnaissance mission. I was going to come over for 5 weeks, sort of test it out, maybe see who I could meet, laying the foundations for moving back. 6 months to a year later. Um, but, uh, at the back of my mind I knew it was a possibility that I would just decide to stay. And after 2 days I was just, uh, I don't know if I can swear on this podcast, but I was just, fuck it, I'm not gonna go home, I'm just staying here.

So I suppose I'd already kind of planned in advance to move to Japan, and I just moved slightly earlier than I intended.

[10:07] Paul: Yeah, and what was your plan like once you mentally committed to staying there? How were you thinking about, uh, either work, sustaining your, your life, um, trying to hack a living?

[10:18] Chris Kirkland: As far as, uh, quite a bit younger and more, um, uh, uh, I don't know, idealistic and, um, uh, maybe more comfortable with doing crazy things. So that was part of it, but I already had a job, so to speak, because I'd already founded Artware. I had my first, at the time, sort of semi-successful internet business. So I didn't really need to go looking for money. All I really needed to do was to figure out the logistics of actually living in Japan, you know, things like what kind of visa would I have to apply to, how do you rent an apartment just like the basics. So it was actually fairly easy for me because I had half the equation already solved.

I wasn't really looking for money. It was just like the logistics of moving there.

[11:11] Paul: Right. And how was running a business online back then? I know everything was pretty early in terms of digital online. Maybe Japan was even more advanced than the US or Britain at that point. Uh, and I know things just didn't work pretty much.

[11:30] Chris Kirkland: Yeah, it was very different. I mean, like, Skype calls were really difficult. Like, there was much less tech available. Cloud services were just starting up, you know. Uh, it was much more kind of, you know, being like an early pioneer. A lot of stuff was a lot harder.

Um, but the main thing was, is it was so new and novel. Like, nobody was doing this. I almost felt like I was cheating, right? Like, I was in the center of Tokyo, this sort of tall office building, looking out over all the skyscrapers, like doing a Skype with somebody in the UK who had no idea that I was in Japan. You know, speaking to one of the artists for ArtWeb, and I just felt like, you know, I was just sort of deceiving this person in some way. But of course, it's pretty normal now.

You know, we're used to just kind of, um, you know, you phone the bank and you're half expecting to be routed to some other country.

[12:25] Paul: Yeah, you have no idea where that call is actually going.

[12:28] Chris Kirkland: Yeah, so yeah, I mean, like, yeah, there's— there was the experience for me of being quite kind of, uh, like, just novel. Um, and then I suppose, you know, the technology foundations were there, so it was doable, and, um, it was easier than it was before. You know, technology just iterates and improves. So, um, yeah. It was good fun.

[12:54] Paul: So you're still living nomadically, living out of a few different locations you keep going back to. What convinced you that this was kind of a journey or a way of working, a way of being that you wanted to keep going on indefinitely?

[13:13] Chris Kirkland: So I suppose in a sense I've stopped. The traveling. And I've— as quite a few people do who live this lifestyle, you tend to sort of converge on a few specific destinations. You basically sort of live in one place and visit other places, right? That's, that's kind of what I'm doing. I had, I had kind of several stages in this journey.

The first one was basically going to Japan. I'd had like a little taste of working remotely when I was in India. And then like moving to Japan was like my first real taste of kind of being remote, even though I was relatively static because I was in Japan for a few years. Then I had like a kind of full-on sort of remote hopping around, 3 months here, 2 months there, 6 months here. But about 5, 6 years ago, I basically, you know, set roots down in Tokyo. I'm kind of taxpayer here, I rent an apartment here.

And I'm here, you know, 7 to 8 months of the year.

[14:16] Paul: So you've done a ton of creative things. I mean, just go to— I'll link up to your website, but you talk about music ventures you're doing, coding ventures you're doing, your websites, your writing. Where does that energy come from? Have you always been wired to create? I know from an early age you were in a band. Um, yeah, where does this all come from for you?

[14:41] Chris Kirkland: Well, my mother is an artist and my father used to work at IBM as a programmer, so I think just a natural product of those two forces. Uh, you know, my mum was always immensely creative. She was always like cheering us on, like doing drawings and writing stories. And then, you know, there's my dad, sort of calm in the background with this logical programmer mindset. So I guess it's just like a natural progression in a sense. I think every— everybody really has like a basic sort of creative core.

It's not always that visible, but it's definitely there. So I think it's probably mostly to do with my upbringing. Like, I had, you know, great parents that just allowed me to do my crazy ideas all the way from childhood through to adulthood.

[15:32] Paul: Right. How did Tokyo Cheapo start?

[15:36] Chris Kirkland: So, uh, very simple really. Me and, um, a good friend Greg Lane, we were in a cheap izakaya, uh, which is like a sort of tapas bar, Japanese tapas bar, and we were just like discussing ideas of new businesses that we could start, um, because we're both looking to do something new. And amongst some of the sort of software as a service ideas we came up with, there was a moment of calm and we were both like Yeah, nobody's done a site about Tokyo on the cheap, have they? Yeah, we should do that. Yeah, yeah, let's do that. And, you know, a week later, threw up a free WordPress theme.

We like bashed out a few articles because both of us had lived as bootstrapped entrepreneurs in Tokyo. Um, you know, neither of us had ever really made that much money. We've made enough, but we'd basically been used to being cheapos. And, uh, Japan is actually quite a cheap country. it's not like Vietnam or something, but it has this reputation for being super expensive and that probably comes from the '80s when Japan was seen to be taking over the world. But basically since about 1992, everything has stayed the same price.

Basically it's pretty cheap here.

[16:48] Paul: Yeah, and is food similar to other places? In Asia that it's relatively affordable as long as you're kind of going to the right spots?

[16:58] Chris Kirkland: It's very affordable. I mean, you can throw $300 on a meal, but you can also spend $3. It's, uh, you know, the, the ramen, the soba noodles, the rice bowls, um, you know, you can get meals in those restaurants for anything from $3. So, uh Yeah, and the quality is amazing. It's like the sort of cost performance for food in Tokyo and indeed the whole of Japan is very good.

[17:27] Paul: I like that as a metric, cost performance of food.

[17:30] Chris Kirkland: Yes.

[17:32] Paul: So what started to resonate as that started gaining some readers in Tokyo? Was it how you were positioning it? Was it just literally that nobody was writing about these things? Because I know the landscape, especially the like blogging and media world, was a bit different when you guys were starting.

[17:54] Chris Kirkland: So even when we started, it was 2012, you know, starting another blog in 2012 seemed like a crazy idea. But the specific landscape for media about Japan, there weren't that many good websites and no one has focused on this sort of content about Turkey on the cheap. It really stood out. It was a very distinct idea. We started getting good signs. People liked the site.

We got good comments. And literally every month we just saw the traffic going up and up. So we kind of fairly early on knew that we must be onto a good thing.

[18:30] Paul: What has changed as you've run that site from the beginning and how you think about running it now?

[18:38] Chris Kirkland: I suppose the scale, the fact that it's, you know, it's a serious business now. Like, when we started, it was just Greg and I sort of doing it as a side project. Um, after a year, we realized that it was going to continue growing, so we hired an editor and started, like, hiring people to write instead of doing it ourselves. We would commission freelance writers to do some of the articles. And that kept on increasing. We would get more traffic, we'd have more writers, and the site started to make a little bit of money, certainly enough to pay for the editor and some of the writers.

But after about 4 years, we got to the point where it was, you know, a nice amount of traffic, but it was just taking up so much of our time. And we realized, okay, we've either got to turn this into a profitable business or we need to just keep it as a side project because it's just too much of a distraction. We need to actually pay the bills. So basically the story of the last few years has been the business side, and that's gone really well. And so yeah, we've kind of— we're probably about 10 full-time staff with another— on any given month, you know, there's up to sort of 20, 30 people on the payroll, including all the different freelancers and part-timers.

[19:58] Paul: Wow. So what have you started to learn about managing remote teams through that? I mean, you were working as a remote worker and then now you have your own team. What is, what is that looking like in today's world? I know there's a lot more written about how to manage freelance or remote teams, and perhaps I think it's kind of natural in the media world, but what stands out for you?

[20:25] Chris Kirkland: Oh God, it's a big topic, that. I think, um, the first thing I'd say, having been doing remote work for, you know, one and a half decades, is, um, to a certain sort of basic functional level, it's quite easy, especially with today's tools. But to really do it properly, you really have to go that extra mile on learning how to use the tools properly learning how to commute, um, sorry, communicate properly with people in remote teams, um, and like learning to compensate for the disadvantages of being in remote teams. So I'd say basically going from the basic functionality to actually doing it properly, it's a pretty big step. And it's something that we still struggle with now where, you know, a lot of our work is just sort of figuring out how to compensate for miscommunications from being a mostly remote team.

[21:22] Paul: Yeah, that's— yeah, I think a lot of people take that for granted, right? We think we can just operate like we do when we have colleagues that just work from home for the day, right? And people kind of underestimate all those in-person interactions that kind of make people feel comfortable with each other or just level out those miscommunications.

[21:43] Chris Kirkland: Yeah, it's huge. I mean, we're social animals and remote work is just not what we were designed for. So you really have to understand that you're kind of pushing against human nature and take steps to kind of counteract that.

[22:00] Paul: You've recently launched HongKongCheapo.com, which personally I definitely need to tap into next time I go there. That place is quite expensive, but definitely going to check that out. I also saw, I mean, if you go to your HighLevel page, you have every part of the continent and potential areas of the world listed out. What's the vision for this? Are you guys thinking cheapo for the 100 biggest cities in the world? How are you thinking about it?

[22:34] Chris Kirkland: Yeah. Potentially. I think it's a model, um, so far it's going well. We've got 3 cities now: Tokyo, London, Hong Kong. Um, and I don't see why it wouldn't continue to work as we expand to other cities. So yeah, definitely our vision is a global cheaper network.

[22:52] Paul: And has your mindset around that shifted to almost building the operating system for how you kind of launch this in different areas? Or is that kind of still evolving and molding?

[23:04] Chris Kirkland: Yeah, we're still fairly early on. I think, um, doing 3 cities is going to be quite a different operation to doing 30 and then more. Um, so we're, we're basically at that stage where we're thinking about the next steps now. You know, what's the, what's the operating system of that kind of, uh, company? What's the different moving parts? How do they coordinate?

We've got a certain amount of learning from coming this far, but I think, you know, there's probably quite a few lessons that still lie ahead of us.

[23:37] Paul: So I'd love to shift gears here and just— you put down to ask you about burnout and extreme dietary experiments. You said these are somewhat related, but I'd love to just offer that as a starting point. Um, to hear about when did you face burnout? When did this emerge and how are you thinking about kind of what that process was like?

[24:04] Chris Kirkland: So, uh, yeah, I, this, this could be quite a long topic. I'll, uh, try and kind of, uh, do a macro overview and we can decide what to zoom in.

[24:13] Paul: Yeah, we can dive in.

[24:16] Chris Kirkland: Uh, so the extreme diet leads into the burnout. So fairly early on in my life, I was already— I'd started doing martial arts, I'd done meditation, I tried fasting, tried like kind of sleep experiments. So I had— I've kind of always been quite experimental and always happy to sort of try doing extreme things. Um, fairly early in my life, I had quite an influential figure in my life. I had a— I met, um, I met somebody when I was 19, very kind of talented, um, uh, interesting creative person, and we became good friends. And he was a bit older, so he was kind of like a mentor to me.

And, um, you know, he was maybe crazier than I was, so But I loved it, you know. I've been kind of learning all these things, learning martial arts, and sort of— it was really, really kind of interesting ride. Anyway, to cut a long story short, is this rather strange woman called Yasmeen came to our city to talk about being a breatharian. And I thought, well, that sounds a bit silly, like just living off breath, and food's quite nice. Anyway, we went to see this talk and I thought it was a bit sort of, um, you know, a bit too new age. However, my friend was really taken by this and the next day announced that he was going to follow this woman's process and become a breatharian.

And I was like, oh well, I'd better do it as well then, you know, because this— he was very influential, he was like a sort of mentor to me. And I was also very competitive, so I didn't like the idea of him doing this thing me not doing. Um, yeah, I, you know, I was quite young and I was a little bit more naive then. So it's obviously a mental idea, it makes no sense and it's kind of nonsense.

[26:15] Paul: So maybe we can define what a breatharian is.

[26:18] Chris Kirkland: So, um, firstly, disclaimer, don't do this, it's a very bad idea, you will die if you don't eat food. Um, but the idea of being a breatharian is, you know, there's some some kind of mystic ability to be able to live off your breath alone, not to need to consume food anymore. And this is different from fasting. You know, I'm a very— I'm a fan and an advocate for, um, you know, carefully controlled fasting. That is a healthy activity. But just stopping eating altogether does end in you dying because, you know, the human body, the animal body requires food.

Anyway, that's the definition of breatharian. So specifically, she had this sort of 30-day process— uh, oh sorry, 21-day process. It's like a sort of 3-week process that you go through, which is basically eating nothing for 3 weeks, and then you're meant to be converted to being a breatharian. Um, anyway, um, it's difficult to kind of tell this story short, but you get the background. I was kind of young and impressionable, and I was sort of following my mentor down down this crazy journey. And, um, I was quite open to crazy ideas.

And, um, we, you know, we went through this 3-week process which was quite difficult, um, quite dangerous, because the first 7 days, um, you're not meant to drink anything. So it's actually no food or water for 7 days, which is very dangerous. Yeah, you know, but generally the human body shouldn't be able to survive that long. I think in our case we were just like at home and we were very relaxed and committed to this process. We weren't like kind of stranded after an aircraft crash or something. So maybe that, um, you know, it's not something I would suggest anybody test, but we, we seem to have emerged, you know, without, um, harm after that 7-day period.

Anyway, at the end of this period, I basically kind of I was believing in this process and I thought, okay, great, I'm a breatharian now. I can just wander around the world. I don't need to worry about eating anymore. But trying to keep this story fairly short, we returned to kind of snacking and eating little things because one of the things she said in this book is breatharian doesn't need food, but you can eat things just for entertainment. If you want to.

[28:42] Paul: So that's a good safety valve.

[28:44] Chris Kirkland: Yeah. So, so basically, uh, you know, we returned to kind of eating sort of snacky type things, you know. I had a very unhealthy diet for a few years following that, but I gradually sort of faded back into more normal eating but never really eating that much. So I kind of had this really weird diet where I sort of still kind of believed that I didn't need to eat but was eating And, um, yeah, that was probably one of the main causes of my burnout, like this kind of extended period of probably about 8 years where I wasn't really eating a very healthy diet. Um, and then coupled with, um, I got into trying to kind of, uh, sleep less, like this polyphasic sleep stuff.

[29:33] Paul: Yeah, that's where you sleep like half an hour at a time or an hour at a time. Something like that.

[29:38] Chris Kirkland: It just— don't do it. It's a really bad idea. And like, I kind of did get— you do kind of get this sort of buzz, and I had this, uh, incredible energy, but it was like this sort of wired energy. It just, uh— now I know my body better, I know like it was giving me warning signs. But, um, I was just in this, this phase where I kind of believed I was invincible. I believed I didn't need to eat, I didn't need to sleep much, I could kind of achieve anything.

And then sure enough, like, reality caught up with me and I got this throat infection and it kind of didn't go away and I was ill for about a month. And basically I ended up in this situation with what they call chronic fatigue, which is basically you're kind of tired and they don't really know why. And so I went from this kind of high-energy, sort of super-wired, enthusiastic state to basically being in a position where I, I couldn't really work. I had just such low energy. And, um, uh, yeah, it was a real kind of struggle for several years. And, um, uh, perhaps I should talk a little bit about my recovery from that process.

[30:49] Paul: Yeah, it'd be interesting to hear about the recovery. I think also it's fascinating. I know, I mean, I was reading about a lot of this stuff as it was happening, too. It seems like there's been a huge evolution just in terms of like the knowledge that's out there, either through podcasts or different kind of professionals now even sharing knowledge. That's, it's actually kind of come a long way just in terms of all these kind of personal development things, right? Now you see like really good sleep insights you can learn from online.

Whereas maybe 10, 15 years ago it was more of these, uh, edge cases.

[31:29] Chris Kirkland: Yes. Yeah, I mean, this is the thing, is like the human body can do extreme things, um, but it does have its limits. And it certainly have— it does, you know, if something gets chronic, then it's a real problem. So maybe you can do these peak experiences for brief bursts, but in the long term you can't get away from that basic healthy lifestyle, which is like good food, good sleep, good social life, enough exercise. Um, so basically my, my recovery process was just discovering that the hard way, just like trying all kinds of things to get healthy again. Um, at first I was trying to get healthy by doing things because, you know, I was always a doer.

That's kind of what led me to that extreme experimental life. But in the end, I realized I just needed to sleep more. I just needed to chill out and kind of allow my body to recover. And yeah, you know, after some years and sort of slowly coming around to realizing the truth, I'm, you know, back in top form again now.

[32:32] Paul: That's fantastic. I, I think that resonates as well. I went through somewhat of a health challenge, not as long as— it doesn't sound as intense as you did, but It was often frustrating, kind of the pace of recovery. Um, it probably, like, just recovering and trying to let my body, like, heal itself was such a painfully slow, uh, process, but one you kind of just have to trust intuitively. Um, and it's very hard, right? If you're used to analytically assessing things and trying to take action and And I know that was kind of a real big shift for me, and it sounds like you kind of had that shift too.

And now you're thinking a lot more about how can I sustain this life in a healthy way.

[33:21] Chris Kirkland: It's the rabbit and the hare, really. Sorry, the tortoise and the hare, or the rabbit and the tortoise. I forget the exact story, but slow and steady, that's how you win the race. Like listening to your body, getting good sleep. In the long term, this really pays dividends. Like, don't get distracted by the kind of fast-paced, um, burst-like things.

That's— that can only last for a moment. It's like the kind of— be like the tortoise, slow and steady, just constantly, um, you know, over the long term, doing things kind of slowly and carefully and doing it well.

[34:00] Paul: Yeah, I love that. I also just want to pause here and say that the podcast does not endorse breatharian techniques and consult your physician before going down these roads. But I also think like it's challenging, right? I'm sure with the fasting from the breatharian experiment, you probably experienced some sort of like uptick from like entering a ketosis state. Yeah, and it's easy to kind of be like, oh wow, there's actually something here.

[34:33] Chris Kirkland: Yeah, I mean, it's great. I still do at least one 7-day fast a year and it's so good, you just feel amazing. But it's not something that can last forever. That ketosis state is something you should use with care. And I don't know, some people do it long-term, but I'm I like the principle of you kind of fast every now and then as a purge, and I think there's a lot of scientific confirmation of that now, that that's a good regimen.

[35:06] Paul: Yeah, definitely. I've been digging into that as well. I can link up to a couple things in the show notes if people are interested. I'd love to go back to the beginning of your story and talk about you losing your first $50,000. I'd first just love to note, like, you list kind of your year-by-year, decade-by-decade achievements. I'm wondering, like, what in that year makes you list that as the descriptor of what happened?

[35:40] Chris Kirkland: Well, I always think you're not really an entrepreneur until you've had, like, some massive failure.

[35:46] Paul: Right.

[35:47] Chris Kirkland: I, I think it's— some people get there without making big mistakes, but they're the exception that proves the rule. Like, um, I do know some people who've kind of got lucky and first time they were successful, but then they go on to lose it because they, you know, they're disillusioned. They, they think it was easy and they can do it again, but they were just lucky. I, I think it's a good thing to, um sort of advocate for going through a failure. And it's, it's not something that's like that bad as long as you, your limits, you limit the downsides. And, you know, you don't want to kind of go lose everything like later in your career.

You know, if you can do it early on, then it's great, or even halfway through. So, um, that's kind of why I made it as an achievement. Um, The actual story, um, it actually ties into the breatharian story. It was through the same mentor. Um, we actually, um, we were doing all kinds of projects together and we started a business, using air quotes, kind of business in quotes. Um, and it was this sort of harebrained idea of making some sort of creative center or music studio, um, you know all the kind of classic bad business ideas rolled up into one, basically.

And what it manifests as was, uh, I had IT skills and I was actually bringing some money in by doing things like, um, web design, IT training. And I was, you know, a little bit of money was coming in, so it kind of looked like a business. Meanwhile, meanwhile, my partner was spending the money I was spending at twice the velocity we were making the money and kind of buying studio equipment. And, um, the problem was he was kind of the older, wiser person, so I just sort of had faith in what he was doing. And, you know, I was just watching our bank balance go down and down and down, but I thought, well, obviously he's got a plan. Um, and of course, you know, you can imagine how the story turns out.

Basically we ended up, um, uh, falling out in a major way. And we hadn't set up an LLC, it was a partnership, so I was on hook for all of the money. Um, you know, we both were. And, um, yeah, basically, uh, we burnt through, uh, I think it was about £30,000, which is at the time it was about $50,000. And, uh, yeah, I, you know, I had to I had to pay off about 10 grand of debt. So yeah, it was quite a lesson, quite a life lesson.

But I bounced back pretty quickly once I was back doing stuff on my own and I didn't have a partner who was spending money twice as fast as I could make it. I soon, you know, I managed to write a check about a year later to just pay the debt off in one go.

[38:43] Paul: Yeah, very Very sensible business entrepreneurship advice. Avoid partners who are mostly just spending money. But easier said than done, right? I think a lot of these things are hard as you're doing it to kind of step back and realize what you're doing.

[39:05] Chris Kirkland: Yeah, I mean, business partnership, it's like choosing a wife or a husband and you don't want to jump straight into it. You want to kind of move into it slowly and get to know each other and get a sense of what they're going to be like with kids or with the access to your bank account.

[39:24] Paul: So you've settled into more, I guess I would say, stable. You're still traveling to a few different locations throughout the year, but how do you think about just focusing your energy on a day? Like you waking up today, how do you think about how you're spending your time and um, what you're working on?

[39:47] Chris Kirkland: That's the million-dollar question. I think it's really important to, um, just kind of focus on your daily routines because that's ultimately what makes the difference. You know, the wind moves mountains over time, so over time. So how you kind of spend your individual days really counts. Um, I guess in my case My particular routines, I always like to start with a nice slow morning routine, doing some sort of exercise, listening to podcasts. So I kind of have this, you know, my body's always in a good state by the time I start working.

I tend to try and do most of my kind of deep work, you know, the high priority, or sorry, the important stuff, not necessarily high priority, but the important stuff early in the day, I'm usually a morning person, and then like in the afternoons I reserve those more for like meetings and conversations and just sort of less taxing tasks, you know, like if I just need to sort of enter stuff into a spreadsheet. But, you know, running a kind of growing business, like every day is different. There's always fires to put out, there's always new things It's, uh, yeah, I try and, I try and kind of practice mindfulness. That's a key, um, story that's always been there for me. I try and kind of be mindful, but it is difficult, you know, with like all kinds of things pulling for my attention. Um, I'm often, you know, a miserable failure at being mindful.

[41:26] Paul: Yeah, well, I, I think a lot of your writing too, you're pretty honest about the process and, uh, your intention too, especially as a leader in a remote company, trying to be pretty people-centric and just kind of cut out the BS and complexity of what a lot of people default to in running a business. How did you come to that mindset? Has that just always been how you're kind of wired?

[41:54] Chris Kirkland: I think so. Yeah. I think I've I've never been afraid to do things differently, or certainly that's how I started my adult life. So maybe it's a lot to do with the early days when I was more focused around making music and creating things, which is a very— that's a very sort of— you're communicating to people. Ultimately being an artist, you're communicating something very personal. I was always kind of quite used to being very direct about and very honest about feelings.

So for me, it just seems quite natural to sort of try and be empathetic, try and understand people. So I think maybe partly to do with music, maybe partly to do with just I was kind of born that way.

[42:49] Paul: Fantastic. Any reading or kind of— but you said you listen to podcasts every morning. What's kind of inspiring you these days or things you keep coming back to to learn from?

[43:05] Chris Kirkland: So for podcasts, I kind of bounce around quite a lot of different podcasts. I got sucked into the intellectual dark web completely by accident. I started listening to a Sam Harris podcast because he's a really good meditation teacher, but he also, um, you know, gets embroiled in politics. And I found it quite interesting. And like a year later, I'd kind of bounced around all of these, um, IDW podcasts and suddenly realized that I'd spent a year learning about identity politics and all these things, which, um, I, you know, it's interesting but I'd much rather spend my podcast time on things like listening to startup stories and, you know, maybe like historical things or, uh, or even just fiction. So nowadays I, I try and kind of, um, I try and find more business podcasts.

Um, lately I've quite enjoyed the Financial Times Startup Stories series. They're, um, fairly short. And very varied interviews with different company founders. I quite like it because it's a British production, so I quite enjoy hearing the British accent because so many podcasts are American.

[44:27] Paul: We have unbridled enthusiasm for podcast creation.

[44:31] Chris Kirkland: Indeed. And many of them are great, but it's just personal. I just enjoy hearing a British accent every now and then. So yeah, that's, uh, Startup Stories by the FT. I've quite enjoyed them.

[44:44] Paul: So I'd love to close with your headstands, which I thought was really fun and just kind of an expression of who you are. Um, for people who are listening, of course, this is a sight of you just in headstands around the world, and I think you can buy the pictures, which I thought was pretty cool. Um, but how did that start?

[45:07] Chris Kirkland: Well, it was very simple. I was in, um, Berlin visiting my good friend Thomas Schelp, who's an excellent photographer. He said, okay, Chris, let's go out and take some photos. So we went into town with his camera, and, um, I think it was the middle of the winter, so there's snow everywhere. And anyway, he said, Chris, do something interesting. So I started doing some handstands and trying, you know, different poses.

And then at one point I just did a headstand, and as he was kind of taking lots of photos, I just suddenly pulled my hands to my side and he took the photo in the split second. It looked like I was just on my head doing a headstand with no hands. And, uh, we were like, oh, that was cool. And then so we spent the rest of the afternoon wandering around Berlin doing more of these photos of me on my head. And basically that's how it started. And, uh, Since then, I've— where have I done?

Kuala Lumpur, Tokyo, Thailand, London, Buckingham Palace, Tate Gallery. You know, every now and then I'll just kind of get into position, do a headstand, whip up my hands, and split second I look like I'm balancing on my head with no hands. My repository of everything I do is on MrKirkland.com. That's probably like the sort of central place if anyone's curious to seeing my various creative outlets and business projects.

[46:34] Paul: I actually know a couple of people who listen to the podcast who are probably going to visit Tokyo. Maybe you could give us some interesting recommendations for Tokyo based on things you write or have discovered over the last several years.

[46:50] Chris Kirkland: Well, I could fill a whole podcast series.

[46:53] Paul: Go to tokyochibo.com, right? Yeah.

[46:55] Chris Kirkland: Well, the, um, I think the, the basics are if you've never been here before, then don't worry too much. Just like, just turning up is already interesting. Like going to a convenience store and seeing how the staff serve you. Um, you know, just riding on a subway. All the basic experiences are quite interesting. So I wouldn't say you've got to kind of have this sort of must-do list.

Like just being in Tokyo is already quite an experience. What else? I have so many tips really. If you're coming in the spring or the autumn, that's the peak season, so make sure you book accommodation well in advance. It's quite nice to be based in the sort of Shibuya general area, maybe not Shibuya itself, but within like a sort of 30 to 40 minute walk. That's like where most of the interesting nightlife is.

And because it's such a big city and the trains stop fairly early, it can be quite inconvenient if, you know, you're having to kind of check your watch to make sure you don't miss the last train at 11:20 PM. But if you stay in the Shibuya area, then, you know, worst case scenario is you're kind of not too expensive taxi drive back to your hotel or apartment.

[48:14] Paul: And is there like great cheap food tip you'd leave people with?

[48:20] Chris Kirkland: Yep, Japanese food, standing sushi, standing soba noodles in stations. So basically if they're saving on floor space by having no seats, you know you're getting maximum sort of cost performance. You know the food is going to be the best sort of cost performance in those places. So yeah, the standing sushi, the conveyor belt sushi, the ramen noodles, soba noodles, those kind of classic local Japanese eateries are the cheapest and always very good quality.

[48:51] Paul: Any last advice you might want to leave to people? I think a lot of people that listen to my podcast are either thinking about carving new paths or are freelancers or self-employed already. What can they learn from your journey over the past 13+ years?

[49:08] Chris Kirkland: So I think, um, it's good to take risks, but don't push it too far like I did.

[49:14] Paul: So, uh, right, yeah, headstands, not breath.

[49:19] Chris Kirkland: Yes, exactly. So yeah, take, take well-calculated risks. I think that's, um, the art of being an entrepreneur is it's not like going into a casino where you're just gambling. You know, take well-calculated risks.