Pushing Remote Working to its Absolute Limit

“I think it’s adventure that drives me. So it’s adventure that is at the heart of all of this. I didn’t really enjoy school. I wasn’t particularly good at school. I was diagnosed, you know, either dyslexic or dyspraxic or, you know, suffered from a bang on the head. But that wasn’t until university. So school was kind of a constant experience of being told that I was smart but lazy, and it just didn’t make sense to me. I wasn’t very good at it. But then I worked. My first kind of career was in advertising, and I was very lucky, I think, to find places that valued people that thought differently.”
Ben Mason

Ben Mason shares his journey of living and working remotely on a sailboat, discussing his background in strategy work and entrepreneurship, including his appearance on Dragon’s Den. He describes the challenges of maintaining a balance between freelance work and boat life, his struggles with dyslexia and dyspraxia during school, and his innovative ventures like starting a pizza delivery social enterprise during COVID-19. He also talks about his current location in the Bahamas and plans to sail further.

Dive deeper into his adventures and learn how to embrace a lifestyle of remote work and adventure by listening to this episode, be inspired by his journey and embark on your own path to freedom and innovation today!

In this episode you’ll hear about

• Ben Mason’s background in strategy work, entrepreneurship, and appearance on Dragon’s Den
• The challenges of living and working remotely on a sailboat
• Struggles with school due to dyslexia and dyspraxia
• Balancing freelance work with boat maintenance
• The feasibility and challenges of remote working, balancing client expectations with the realities of boat life
• Future plans without limits

Key links

Ben Mason LinkedIn
Ben Mason Twitter
Fortnum & Mason 
Dragon’s Den

About our guest

Currently a freelance CSO providing marketing consultancy including brand strategy, product innovation, naming and creative ideas, Ben works remotely from his sailboat.

Previously Co-Founder at Love Triangle, a pizza delivery social enterprise launched summer 2020 during Covid lockdown. In the midst of lockdown they raised many thousands for a foodbank, met the King and employed over 100 people from the hard-hi hospitality industry.

Previously Ben founded a baked beans startup that Richard Branson described as ‘a pioneering business idea’ and The Daily Mail described it as, ‘twice as good as Heinz and 10 times tastier than Waitrose’. Check out Ben’s appearance on Dragons’ Den!

Transcript

Chris Hudson: 0:05
Howdy everyone. And maybe I should say ahoy, I don’t know, but anyway, pushing past the cryptic maritime clue in this intro, I wanted to bring you another unexpected episode of the company road podcast. So I was scrolling through my LinkedIn over breakfast one day and kids noises everywhere. And you can imagine the scene. A lot of people are in the situation. It’s basically industry news campaign. New campaign, new products, new tech, there’s a rant, there’s some AI, there’s infographic, there’s another rant, there’s a survey, there’s maybe some more AI kind of posts, and people are posting about the same sort of stuff, basically. And I saw this post and I might actually read a bit of it out, which is, totally unexpected for me. So like reading through this thing, anyway, post reads, day two, we got struck by lightning. It happens to sailboats, but it’s rare. Something to worry about, not something to expect. Day two in the Bahamas, our prize after six months of toil, six months replacing all the electronics after the last lightning strike. Yep. This boat has been struck twice, an insurance write off we rescued last November. And then it goes on, and, there’s some interesting things in the post which you should see, and, definitely link to it in the show notes. But yeah, the end of it is, so this is me now, I live in a sailboat, pushing a remote working to its logical conclusion. I’ve been meaning to write one of these for months, partly so my mum knows we’re still floating. Perhaps it’s therapy and definitely as a reminder that I’m in the market for freelance work because this boat won’t fix itself break out another thousand as they say, so it really jumped off the page. And after that, I thought, well, life on the sea, traveling the world, pushing remote working to its logical conclusion, I need to get this guy on the show. So basically here he is, and this is like. Maybe a day or two after I saw the post and Ben, you’ve been super kind in coming onto the show and this wonderful person, Ben Mason, we actually connected like many years ago, back in London, we were interviewing Ben for one of the roles where we’re working in innovation consultancy back then, and Ben, you’ve tried many things in your life, beyond boating, you do a lot of strategy work as a strategy officer and, lots of things in between you’ve like back in the day, you’re quite an entrepreneur back in the day, you were. On Dragon’s Den, even, and you are selling luxury baked beans to Duncan Bannatyne and the crew. And, So like reading through this thing, anyway, post reads, day two, we got struck by lightning. It happens to sailboats, but it’s rare. Something to worry about, not something to expect. Day two in the Bahamas, our prize after six months of toil, six months replacing all the electronics after the last lightning strike. Yep. This boat has been struck twice, an insurance write off we rescued last November. And then it goes on, and, there’s some interesting things in the post which you should see, and, definitely link to it in the show notes. But yeah, the end of it is, so this is me now, I live in a sailboat, pushing a remote working to its logical conclusion. I’ve been meaning to write one of these for months, partly so my mum knows we’re still floating. Perhaps it’s therapy and definitely as a reminder that I’m in the market for freelance work because this boat won’t fix itself break out another thousand as they say, so it really jumped off the page. And after that, I thought, well, life on the sea, traveling the world, pushing remote working to its logical conclusion, I need to get this guy on the show. So basically here he is, and this is like. Maybe a day or two after I saw the post and Ben, you’ve been super kind in coming onto the show and this wonderful person, Ben Mason, we actually connected like many years ago, back in London, we were interviewing Ben for one of the roles where we’re working in innovation consultancy back then, and Ben, you’ve tried many things in your life, beyond boating, you do a lot of strategy work as a strategy officer and, lots of things in between you’ve like back in the day, you’re quite an entrepreneur back in the day, you were. On Dragon’s Den even, and you are selling luxury baked beans to Duncan Bannatyne and the crew. And, going up against a number of people and getting your beans into Fortnum Mason, you’ve tried a number of other things, but yeah, what is this got to do with intrapreneurs and the world of work? You might ask? Okay, so we’ve got the boats, we’ve got the beans, we’ve got to put this all together. I think we want to talk a bit about, how far you can push remote working, how far you can, how far you can No, basically take your passion and focus on that and then bring more of yourself back into work. Probably as a result is probably the way we’ll get to Ben. Thanks so much for coming on the show. Welcome. The pleasure. I don’t know what kind of introduction was that and how would you describe where you’re at? Like actually, where are you right now? Yeah,

Ben Mason: 4:26
emotionally or geographically. So geographically. Anyway. Yeah. In Bahamas. Yeah. We bought the boat in Florida. Spent six months fixing it and sailed to the Bahamas two weeks ago, and then promptly got struck by lightning again. So we’re currently stuck here fixing the boat again, which has seems to be What happens when you get struck by lightning? Because I’m sure people are curious. It can vary hugely. It can be really, really serious. Mostly humans don’t get struck because boats have big, it’s a sailboat, there’s a big metal pole sticking out the top. But the most serious is it can blow a hole in the bottom of the boat. That’s very, very unlikely. The most recent strike was a very mild one. Killed a bunch of our electronics, two fridges, the autopilot, expensive but could have been much much worse the one the bow was struck by lightning before we bought it and it Destroyed every single piece of electronics on board.

Chris Hudson: 5:14
Oh, wow. Yeah, that’s gonna hurt So for a remote worker, it could have started better.

Ben Mason: 5:20
It’s probably well I’m really glad the starling was infected because I realised I like I’m totally reliant on Internet here and I, brazenly said, yeah, I can work from anywhere in the world, but I only have one way of connecting on the badminton. It’s been a bit of a lesson is I probably need some backups.

Chris Hudson: 5:35
Yeah, great. This is where you’ve ended up. You’re in the Bahamas. You’re on a boat. You’re in a cabin there?

Ben Mason: 5:39
Yeah. I’m in what they call the saloon. It’s like the living room, living room and kitchen in the middle of the boat. I’ve planned to turn the cabin into an office at some point. The ideal would be to have air conditioning in there because it gets pretty toasty at times and have my screen and all that stuff, but we’re not quite there yet. We do have running water and electricity and internet, which is much better than where we were six months ago, so.

Chris Hudson: 6:03
So you can get your internet from anywhere in the world with the satellite connection, is that how it works?

Ben Mason: 6:07
Yeah. It’s super fast from absolutely anywhere. So it’s, that’s a game changer really, because I do freelance advertising strategy as my bread and butter and that just enabled me to do that from anywhere really.

Chris Hudson: 6:18
Yeah. So we’re putting these things together. So you’re on a boat, you’re doing this strategy work. You’ve obviously did the beans back in the day, you’ve done a few other things along the way. So maybe if you could just describe, I guess the, the journey and I don’t know how far back you want to go. You could even start with the young Ben if you wanted to, and what characterised your outlook on life. How do these new things come about for you?

Ben Mason: 6:36
I think it’s adventure that drives me. So it’s adventure that is at heart of all of this. So I didn’t really enjoy school. I wasn’t particularly good at school. I was diagnosed, either dyslexic or dyspraxic or suffering from a bang on the head, but that wasn’t until university. So school was your constant experience of being told that I was smart but lazy. It just didn’t make sense to me. I wasn’t very good at it. But then. First kind of career was in advertising and I was very lucky, I think, to find places that they valued people that thought differently. And I think that I’d always struggled at school because I was trying to do things differently. I remember when, a dyslexic tutor at school, at university, taught me how to write an essay and I’d got all the way to the end of my third year at university without understanding how to write an essay because nobody ever explained it. To me in a way that made sense. And when she explained it, I was just like, is it really that simple? I’ve been trying to write original thought, but the whole career and was useless at it. And then I fell into advertising. Well, I didn’t fall into advertising. It’s quite hard to get in there, but I found a place where they value people that approach things differently. And. I didn’t think I’d stay in advertising very long because I’ve always just wanted to start companies. That’s what’s always driven me right from my childhood. I just wanted to, they call it a founder now called an entrepreneur. Then I, who knows, that’s what I wanted to do. And I think that was driven from. A feeling of not fitting in organisations. School just felt like an anathema. I had friends and I liked their side of it, but I just didn’t understand what they wanted me to, on the paper. Just didn’t, whatever I did just seemed wrong. So I never thought that I would work in a big organisation. I thought I would have to create my own. So I just, yes, I was lucky that advertising agencies and the one I ended up working at for seven years was a startup and felt like building a business. So I think it satisfied my, my needs. Entrepreneurial gene, I suppose, as you’d say, but then I left that and I started the posh baked beans business. And that was in, a few supermarkets and dragon’s den and ran that for two years that eventually you just couldn’t get traction in the big supermarkets. It was a fresh product, so it wouldn’t ever survive without the likes of Tesco and has to run board. So. That was two years, just couldn’t quite find product market fit, but learned a huge amount. Then I went traveling and sailing for a bit, funnily enough, actually. And then I I was on the verge of moving to the U. S. when the pandemic hit. My visa arrived in April 2020 after four years of applying for it. So I didn’t go to the U. S. and that sort of frustration turned into starting a pizza delivery social enterprise. I built for COVID really food delivery was booming and so was poverty. So we started a pizza delivery business called Love Triangle, which gave a pizza to a local food bank for, uh, give donated a meal to a local food bank for every pizza we sold. So that was actually really fun and rewarding and amazing first year. And then year two, we just, Got hit by crazy inflation with Brexit and COVID and Ukraine and all these crazy things happening. And that tanked the business at the end of year two. And that was the moment I decided I didn’t want to be running a business that tied me to a single postcode in South London at the very moment that it suddenly become like culturally acceptable to work from anywhere really. I think that was a big cultural change in the pandemic. And so I thought I’ll fast forward my Dream of living and working or living on a boat because I think I can work from it now. So that’s the whistle stop tour of how I ended up here.

Chris Hudson: 10:11
Yeah, I want to go back to some of those stuff with a sort of high level view But yeah, I mean thinking back to you and how you were in some of those more organisational And maybe constrained environments in some sort of way. So, yeah, maybe talking us through, some of the things that you noticed about either the experience or yourself that made you feel this isn’t quite right or, how are you responding to that? And how, as an entrepreneur, I guess, with that hat on, you were able to. to still manoeuvre in some way. So how did you go about that?

Ben Mason: 10:40
So how, the question is how did I deal with the sort of challenges of organisations? It’s funny really, it always takes me back to school and university where I just felt like I was in organisations that didn’t fit, that wouldn’t value what I did, and it’s very difficult at that age to realise that, but I just Didn’t feel that when I did stuff that I thought they wanted, they didn’t want it. And then it was just very rewarding to find advertising agencies where they, they wanted the opposite. They wanted people to do, were doing things differently and thinking in different ways. I guess I learned a lot. In this sort of advertising world and agency world, because I learned how to write there, actually, I suppose I wasn’t allowed to do English GCSE. So I wasn’t allowed to do English A level because I couldn’t write well enough and now I get paid to write. And so it’s funny how educational organisations didn’t work for me at all, but employment setting of the advertising agency managed to universally teach me how to write. And now I really enjoy writing and get paid for it and it’s something. Yeah, I’m proud of. So I don’t know what, I don’t know if I did much different. I tried really hard to be honest, and I deliberately didn’t try at school because I learned early on that it was better to be seen as smart and lazy than trying hard and stupid. By the time I got into advertising, I think I was just full of energy and it was, it was exciting and fun. And I tried really hard.

Chris Hudson: 12:10
Yeah. I think the thinking differently is interesting. I was also in that situation and thinking differently when everyone else is also thinking differently, it can feel quite hard at times and I don’t know, from a standing out point of view, from a differentiation point of view, whether you felt that in a competitive sense, do you feel like there was always like, Somebody else that was trying to out weird somebody else because it was, I’m going to take that totally different direction, but it, it was, I don’t know, it felt like an incremental process a little bit. So somebody suggests this, I would suggest this and it gets more and more left field to the extent that it’s out there. And then, then you converge on something that’s a little bit. Bit more agreed upon, but I don’t know, a lot of egos flying around. What was your experience? Yeah, it

Ben Mason: 12:50
can be and I really have never had much time for that. It seems counterproductive to be honest. We’re social creatures. I guess that’s where the egos come from. But working with fun, smart people is really fun and I just enjoy everyone’s input.

Chris Hudson: 13:05
So I guess there’s a pretty big change, from obviously working in some of those environments to then, working in an environment where you now control absolutely everything about. Your work and how you set things up and what’s been the process for that in setting up in a way that you think works so far on the boat? Don’t know if it’s working yet. Yeah.

Ben Mason: 13:22
I guess I’ve been working freelance for over a decade now, 11 years, I think, and in that time I’ve started two, businesses. So I think the process of Learning to work for myself in a really true sense has been very gradual over that time. And I think I’ve learned stuff about myself. I think a huge one about productivity, I think, is that learning, and this is, I think, organisations tend to be terrible at is nobody does eight hours work in a day and. I might do eight hours work, really busy day with the deadline. You might do 10, 12, 16 hours, but you’ll be absolutely destroyed for three days afterwards. I’ve learned to be very comfortable with the fact that most of the time, let’s say I’m just putting around, but say there’s four good hours work in a day. I’m learning to do that when I’m feeling ready to work and productive, and I’ll get more done in three productive hours than I will eight hours. So I think learning to work when the work flows has been a big thing for me over the time. That’s something that doesn’t fit well in organisations. There were definitely some models, advertising agency models, which are built for freelancers, which are tackling that. One of my clients has been there, done that, and they’re very, they’re designed for freelancers and they systemise everything. So it doesn’t really, there’s meetings and workshops to attend to, but the whole thing is structured for freelancers. This type of working, no matter when you do the work, and it’s very formatted rather than the more traditional way of sitting, in an agency in London for eight hours a day. So I think it’s definitely been a journey of trying to figure out. When I work and how I work then you put that put that into a boat and it becomes more complicated because you have to deal with weather and maintenance and other Complications

Chris Hudson: 15:18
tying knots. So what the hell the things that you have

Ben Mason: 15:20
to know exactly

Chris Hudson: 15:21
tying knots and pirate things All of that all that Climbing up the top, do you have to climb up crow’s nest and, have a look and, I don’t know.

Ben Mason: 15:29
We don’t have a crow’s nest, but I will have to go up the mast at some point, probably this week. I haven’t been yet. Yeah, right. How far is that? Is that a bit of a climb? You’re not afraid of heights? 62 feet, which is 20 odd meters. Yeah, that’s a good distance. We dragged anchor in Hare Bridge at six o’clock in the morning and broke some stuff off the top of the mast, so I need to get up there and reattach it. Oh, good.

Chris Hudson: 15:54
Well, if you, if you know about your flow and how you can work on, the work that pays in a more efficient way, then obviously that’s going to help. You could say, I’ve got this time, spent time doing the masks and things, and then you’re going to come back to your work. I don’t know. It’s like a productive form of procrastination in a way. True. I like that. You’ve got things to do before you get around to it.

Ben Mason: 16:13
Yeah. Yeah. I remember somebody saying to me, and this was a reference to advertisers, but you never get any better. You just get faster as you get more experienced. I kind of like, it’s obviously not entirely true, but you definitely, learn how to do the same stuff a lot quicker.

Chris Hudson: 16:27
Oh yeah. You can go fast, slow down in a way, so you can, you can basically condense the time that you have to spend on something that’ll then free up time outside of it. Yeah, as you were saying, it must be quite cathartic in a way and just relaxing, doing some of that, some of those tasks that, either you have to fix something or you have to plan a little bit, just the, just the routine schedule of how you’re getting around, where you’re going and that sort of constant It’s good. I don’t know if it’s the same as a creative team playing pool all day to come up with an idea in an office somewhere in Soho, but it’s like you’re doing something to take your mind off what’s, that maybe you’re thinking about things as well at the same time.

Ben Mason: 17:05
I’ve not seen it like that. And. It might well do. It hasn’t felt like that for the first six months because it’s been really overwhelmed. So in a way, it’s felt more like, more like a startup, to be honest. So I think as an entrepreneur, you end up doing loads of things that you don’t know how to do. Because at the beginning, you’re doing all the jobs in the business and, you don’t know how to do most of them. And it felt like a really extreme version of that because I’m not a mechanical person at all. I’m not handy I could do computer stuff. Just, the idea of taking an engine apart just seemed like something I would never do, but it’s something you have to do. So I’ve been painfully dragging myself up that hill for the last six months, and it felt really overwhelming at times. So trying to balance the job around that, paid work around that, was tough. I take your point. I really hope there’ll be a time when I can do the oil change on the dinghy engine and well, cracking it for a client in the back of my head. That sounds great.

Chris Hudson: 18:02
Yeah. Asynchronous or subconscious, something will be happening in the background. Of course, which is hugely important. That’s the dream and then it’s even more efficient because you’re, you’re basically, you are, you are doing two things at once. I can be drinking cocktails on the back of the boat while working. That’s it. But I suppose this whole process has probably tuned you into that a little bit. Do you find yourself in your thoughts maybe a little bit more than you would have been otherwise in a more fixed routine before?

Ben Mason: 18:27
I don’t know, to be honest. I feel like now I’m feeling more comfortable with the maintenance side of the boat and it’s just we’ve got the electrics working and like it’s a comfortable place to live which it wasn’t when we first moved on board so i’m starting to relax more and it’s only you know since coming to the Bahamas last two weeks like really enjoying the environment it was quite stressful in Florida whether it’s hitting bridges or bumping into other boats it was quite intense period. So yes, I think it’s really stunning where we are now, like go out and you can see water’s the most beautiful transparent water I’ve ever seen. And so there’s definite advantage to that of sort of like refreshing the brain and you get sucked into a stressful situation with work and then you can look around here and go, actually, life’s good. It must be stunning.

Chris Hudson: 19:17
Uh, I can only imagine. Yeah. Just to have that available, I think to you as a full back and as a situation really. It must be hard though. It must be hard. It’s a bit like, when you think, take things out of context and you’re talking about working as a freelancer and strategy work, and you might be working on, I don’t know, a nappy brand or somebody that I don’t know who it would be, you’re, you’re working on a brief. And yeah, you’re in the Bahamas and there’s clear water and like there’s something it doesn’t sit in that environment naturally. So how do you feel about that when it happens?

Ben Mason: 19:47
In a sense, I think that’s the art of advertising really because the process is putting yourself into other people’s heads and how they think and understanding them and, and you’re often selling things that you don’t buy or So, that hasn’t been difficult, I don’t think. I think balancing, juggling many things has been more challenging. Just the kind of like, juggling boat maintenance. Daily tasks are just harder on a boat, right? Making sure we have enough water. We make all our own electricity via solar, or we run the generator if that So, it’s like you have to do everything, you have to do many of the things that a city does for you. Using, all our own sanitation, all that kind of stuff. So like juggling all of that with a freelance career, with boat maintenance. So that’s been the challenge I think is, is knowing when, switching mode,

Chris Hudson: 20:41
I think. I think that’s always the freelancer’s challenge in a way, and actually context switching is harder, it’s hard for a lot of people in general, but yeah, switching around, but also knowing when to stop with which part, how much time you’re dedicating with which part, because, if you’re in your, relaxing state and your feet are in the water in the Bahamas, that’s great. But part of you must be thinking, okay, what else do I have to do now on the boat? It’s a bit like when you go camping, there’s always something to do. Or in life, you just sit around the house, that you’re just walking around some of the rooms and you just see things that have to be done and then say, but work, how do you settle that in your mind? Is it like you’re fixing times of the day to do certain things or are you. You’re a bit more free and flowing with it.

Ben Mason: 21:20
I’m still working with mostly European clients. So the time zone means that, and on a boat, you fall asleep early and wake up early because it’s gets really dark around here. So I tend to wake up early and then be online working pretty early with five hours ahead of me. So there’s a definite rhythm to the day where it’s like paid work comes first and then both stuff comes later. It doesn’t leave time for exercise, sadly, because I used to like to exercise in the morning. Yeah, I guess you have to make, make adjustments. Talking about rhythm, weather is a big thing on boats. Like, we are so subject to the weather, and I see the lightning strike story that I told you was an extreme version, but the potential of that can happen where you get thunder and lightning storms every few days at the moment around here. And that’s what we’re doing. With that comes really intense wind, which means you immediately have to be keeping an eye on whether the boat’s moving, when it shouldn’t be moving, is the anchor dragging. So we live by the rhythm of the weather in a really like, powerful, fundamental way. And so it’s quite hard to balance that with the expectations of the client, for instance, because there was supposed to be a thunderstorm at the moment that we were going to record this. And I almost emailed you this morning going, it might be possible, it might not, because it could be like howling out here and you won’t be able to hear a word I say, and I’ll just look really stressed. But, I’ve been watching the radar over the day and, and it’s The radar predicts where the, the actual rainstorm is going to move and it’s been dissipating. So I think we’re going to be fine. And it’s. It’s completely calm now and we can hear each other. So the weather is our overlord, if you like.

Chris Hudson: 22:58
People talk about this in nature. You feel part of something bigger and connected to something bigger. It puts things into perspective quite neatly. And I certainly found this when I

Ben Mason: 23:08
Fear does as well. Fear puts things into perspective really neatly. Like you get quite scared sometimes on a boat because 30 mile an hour winds on when you’re in a house in the city, you wouldn’t even really notice. For us, that’s intense. 40 mile an hour is dangerous. That would be a windy day on land. So it’s, you just have a different relationship with your environment. And that, so I guess there’s two sides to it. There’s the beauty of going out there and looking at this incredible water and feeling so lucky. And that can refresh you creatively. And then there’s the like abject terror of other times, which is nature’s way of making you pay for it.

Chris Hudson: 23:43
You were saying earlier that you identify as a bit of an adventurer. So, so maybe you could tell us a bit about your, I guess your appetite, or craving for risk, or fear, or something that’s terrifying, adrenaline, I don’t know, when did that all start for you?

Ben Mason: 23:57
I think I’m quite a risk tolerant person. So, my sister talks about type 1 and type 2 fun, and type 1 fun is like when you’re having fun, and in the moment you’re like, yeah, this is really fun, and type 2 fun is when you’re like, having a real intense bundle of emotions, then afterwards you’re like, ah, that was really fun, but in the moment you’re probably feeling terror, fear, and so I think there’s a type 2 fun thing going on. Like, I just like to try things as well, I think that’s probably where a lot of this stuff came from and has driven some of my entrepreneurial stuff, sometimes to a fault really, I think I will do another startup and I’m really hoping to do something that I have more experience doing because I’m very drawn to new things and new things are difficult because you don’t know how to do it. I like learning and I think that’s driven a lot of this stuff with the boat, I’m learning a huge amount. So figuring out systems, I think that’s the, the strategist in me, the advertising strategy in me is like figuring out how things work and how they could be done better. That’s a big part of managing a boat, whether it’s the sailing or the systems or, I like researching stuff and I like figuring stuff out. So I don’t really know when happened. I think it’s quite a fundamental personality thing. Maybe the figuring things out has come from. My career, yeah, I think there’s just a, could this be done better drive going on and just like wanting to try stuff. I remember somebody I worked with who’s very insightful human described me as an experienced junkie, which I thought was quite. When, when in your career was that? Was that after

Chris Hudson: 25:30
you’d done the beans and everything else or was it? Before beans. That was in, in half times and downs. Yeah. Yeah. Okay. So it probably spurred you on, did it? Made you do more. It’s like, Hmm. Yeah, that seems about right. Got a reputation. So uphold now and, uh, yeah, you’ve taken it. You’re taking it to the extreme, obviously, as you point out with the freelance work and the boating and the remote working. overall, you think remote working in this way is, is okay. Obviously people are struggling with a regular Teams meeting, from the kitchen or the lounge. You’re doing it in the way that you are. How have you found the experience of doing it?

Ben Mason: 26:01
It’s a really, I think we could do a whole. Podcast just on that topic, really, I think remote working is very interesting. And I think it feels like it’s like many things COVID pulled it forward 15, 20 years, and then there was a backlash. You saw all the sort of Silicon Valley firms that hit the news, demanding their employees come back in and, seen this battle happening everywhere. I feel like it’s really possible. And there is a definite overhead. There’s like a an emotional and cognitive overhead of me living on this boat. It takes more effort and uses more of my energy and my brain to figure out living on a boat. Now it should get a lot easier over time but you know if I’m being really honest and you know perhaps shouldn’t be saying this publicly but no there’s definitely an overhead there but there’s a huge overhead in commuting. Uh, cognitive and emotional overhead in commuting, so I don’t think it’s necessarily negative. I think it can totally work. Like anything new, it’s really stressful at times and figuring out how to do it. And I really wish I had like a place to sit and work. Did my flat in London, I had my place set up and I, had my second screen and I think that stuff’s quite important and I don’t have that yet. So systems and processes and things can reduce that, like cognitive overload or cognitive overhead, if you like. Yeah, there’s actually quite a lot of people doing what I’m doing, but I think it’s just a subculture that you don’t hear about so much unless you’re in it. There are a lot of people running businesses. There’s a lot of, it used to be like retirees and vagabonds doing this basically. And now there’s families, there’s remote workers, there’s people running little businesses and big businesses probably from boats. And then of course there’s all the YouTubers as well, which I think have made it pretty famous.

Chris Hudson: 27:56
So, can you spot them? They’re just doing something that, I guess like you’re on your boat and you probably see it. And you can see things from a distance. You get a bit closer, you can start to see what’s going on a little bit. Yeah. You must’ve met some interesting people in that respect. So from some of the ones that you’re describing.

Ben Mason: 28:10
Yeah. And community is really important in this lifestyle because you can’t do a lot of things on your own, on a boat, and I don’t know how to do so many things. And I meet a lot of really experienced people who. Helping me. There’s a guy flying out tomorrow to come and stay on our boat for a week and work as an engineer for five days. Helping us fix the boat and fixing the boat and I met him that morning that we dragged anchor and hit the bridge Because we found some damage to our rudder it turned out to be old damage But he he was our neighbour and he said oh well look I’ll swim down and have a look at it And he swam down and fixed it there, and then he brought some like waterproof Epoxy and so he swam down and fixed it and that was how we met and now he’s Saving us from this lightning strike. So community is hugely important and necessary. And I think that drives the community out here on the water.

Chris Hudson: 29:02
Yeah. Oh, that’s incredible. Just, yeah, you find people with skill and willing to be able to help you out in one way or another.

Ben Mason: 29:08
Yeah. And people want to, cause then it’s difficult. It’s interesting with the organisational thing, really, because it’s, I guess, it’s the loosest form of organisation, really, the sort of boasting community in Anchorage. It’s very informal, but it’s really necessary.

Chris Hudson: 29:25
No, I really like that. I think that there are definitely parallels to the working world and how people present those confidence and I guess, threat or fear, within a business context, sometimes I feel like, the signals that you put out there can be really important in terms of how, what happens next, what are you laying down as the next step? What’s the next natural step and how should people respond to you? So if you’re in a room and you’re visibly distressed, then it might encourage people to respond negatively and in a hostile way or competitively, but it could also be incredibly. Opening, for the conversation, the situation, like people might want to come in and help you like you’ve described by swimming, dance out, fix your boat. That’s really cool.

Ben Mason: 30:05
Yeah. Necessity drives a lot of stuff.

Chris Hudson: 30:07
Yeah. And in terms of positioning yourself, have you found people have received you, working in this way in the working world where then. Like I said, they’re stuck in a tiny meeting room somewhere in East London and trying to brief you on this thing. How does that go, Dan? You got your glowing tan, your feet are in the water in the Bahamas, cocktail on the side.

Ben Mason: 30:28
It drives a lot of conversation, put it that way. And There’s certain meetings, where having a meeting with someone the other day, there was a more sensitive meeting, we say, someone I didn’t know, and the person, my co founder, I suppose, that had set the meeting up was like, can you just blur your background? Because people always see the kind of, Oak paneling all around me and they’re like, you want a boat? And then you lose the first 10, 15 minutes of the call talking about that. So I think there’s a practicality of like, we need to get some stuff done. So let’s not talk about the boat, but obviously that I really appreciate that because it’s nice to be doing something interesting that the people remark on and want to talk about. So, yeah, I was definitely careful when having calls with people in London in the beginning of the year where it was beautiful weather here. And we all know what. London’s like in January. So I did a lot of like calls from small rooms rather than out with beautiful blue water, but mostly people are accepting on it. I think people find it interesting and exciting and they want to talk about it. I haven’t had. a negative reaction to it yet. We’ll see if, I don’t know, talking to more formal, lawyers, investors, that type of thing, would it be an issue? I don’t know. Perhaps, perhaps there’s a balance.

Chris Hudson: 31:48
Yeah. There’s obviously. There’s ways to handle it. If it happens, you can always change your background, you can get your Meteorium in Slough background to bring up. That’s what I need, isn’t it? I need to find a corporate background. Somebody would happily provide it to you, I’m sure, just to the, the pressing meeting space somewhere. But, yeah, it’s considerate of you to take the meetings in a In an indoor environment rather than outdoors sometimes, so you could be anywhere in the world. But yeah, maybe part of that, maybe that’s part of your kind of refurb, you’ll, you’ll think about how to. A range like, the YouTubers and so on. I’ll get a green screen. Yeah, exactly. Yeah. You could be anywhere though. One of the things we’re talking about in this stage of the podcast is around growth and, and strategies for growth and personal growth and, I guess organisational growth ultimately, but, but for people being able to almost spot what needs to be done for themselves and to move in. And move forward with that and take a step. So from that point of view, I mean, obviously you’ve tried a lot of things and you do start up, you’re starting up ventures a lot. And, you’ve obviously done this on the boat. So, from the point of view of, I guess, sharing some of your spirit and your mindset with people that are maybe thinking about, okay, making a move or how to grow in themselves a little bit more. Have you got any, any thoughts, perspectives on that?

Ben Mason: 33:05
Yeah, I think the biggest thing I’ve learned is just to get on with it. That sounds a little facetious, but I think there’s a really powerful truth underneath it, is that it’s really hard to get anything done, whether you’re working for yourself or in your big organisation, like, inertia is your biggest enemy. And so just getting anything done, I wasn’t a productive person for most of my life, and I feel like I thought maybe I actually am a productive person now, some of the time, and I think just getting small things done, making some progress. And I think there’s a decision making thing there as well is especially on your own. I think it’s really hard to make decisions sometimes. I found as a solo founder, really difficult. I got one, I got my first employee and she was amazing because she just would take me out of this sort of mental fog. Of indecision, which I think is really easy to get stuck in. And I think making fast decisions and then seeing how they feel is, is another good way to just keep, keep things moving. And I think that’s everything really is, is actually moving. Everything we do has been done before in a way, really, in some form. Like we might be starting a really innovative business, but someone started a business like in the past or a charity or whatever it is, like everything’s been done in some way before. So, if you can find the people that have done something pretty close and help them help you do it fast, I think that’s the biggest thing I’ve learned over the years because it’s so easy to get stuck.

Chris Hudson: 34:40
Have you found the process of identifying some of those people or influences that you think would help in that situation? Has it been, again, a bit of a trial and error, going to try a few people out and see what works or have you found yourself gravitating soon? There’s a lot of talk around bias, basically, and you. You look for people that mirror, your own attributes in some sort of way. But do you find the people that point out, the blind spots in a way are the most useful or vice versa?

Ben Mason: 35:06
Yeah, I really like working with people that challenge me and, and think differently to me. And I find that really rewarding. I’m sure there’s a whole load of bias going on. I think also though, and this really applies to, to your entrepreneurs idea is when you put yourself out there, people gravitate towards you and that’s another reason to just get something done because we’ve always had, you have a lot of people go, I’ve got an idea for a business and people project these ideas. They don’t want to tell anyone because it’s such a good idea. That they can’t bear to tell me or I copy it. And I’ve always just thought the more you talk about something, the more likely it is to happen, the most likely thing is that it never happened. So I think going back to your question about attracting people or, or finding the right people, when you do interesting stuff, people gravitate towards it and they see the, you put yourself out there, I’m sure you found when you started company road, he started it. People were drawn to it and wanted to be a part of it because you’d gone out there and started it. And I just think that, like the, it’s the same with this boat, by actually getting out here and doing it. One, boat people happen to help me because they know how hard it was to get it done. And then, I’m hoping that people will give me more freelance advertising work because they go, Oh, that’s interesting getting stuff done and getting out there.

Chris Hudson: 36:24
Yeah, I think that’s great advice. Definitely relate to that from the point of view. Starting this podcast almost a year ago and just seeing, with a bit of a punt where it might go. And obviously, I’m able to have like amazing conversations with people all the time. And, and this one today is awesome as well. But it’s like, you wouldn’t have expected it. You would have anticipated it. You couldn’t have planned for it, but you’re basically just there. You’re laying the roads and you’re walking down it and you’re seeing where it goes. And

Ben Mason: 36:47
there’s a mindset thing there isn’t there that I think is really interesting because I’m sure we all feel this sort of imposter syndrome is too strong a term for what I mean, but we all feel like we don’t know what we’re doing when we start something and but you came to me and you’re like, I’ve got a podcast. Do you want to be on it? I’m like, Awesome. He’s a podcaster. Of course, I want to be on it. Whereas I’m sure when you were starting, you didn’t feel like a podcaster a year ago. Just as I didn’t have any idea what I was doing on a boat. But once you put yourself out there, you’re learning really fast and other people are going, Oh yeah, they are that person and they’re really good at it. It’s sort of a, a self validating cycle.

Chris Hudson: 37:20
It’s funny. It’s now all people ask me about, which is like a really weird thing because I am consulting and doing other things on the side. Various other projects, recording a music album at the minute as well. But it’s like, yeah, about the podcast, you can go back to that in the chat. It’s like, yeah, people just want to talk about it, which is great. It’s a connection point, isn’t it? You, you find commonality through those things. And I think the more creation that you do and put out into the world, obviously the more people, I guess the greater chance for connection is, there, there’d be, more coverage, in a way. If people wouldn’t spend that amount of time with me. On any other day, they can tune into that and, and probably get more from me than they would if they met me for coffee for 20 minutes, I don’t know, it’s an interesting one. I like it. I think it’s cool. And, I think, we’ve talked about creativity, talked a bit about influences. One of the things is maybe around choice and maybe, the illusion of choice, because, you and I, in our situations can choose what we want to work on most days. I think that process itself is a little bit alien, a little bit foreign to a lot of people. From the point of view of choosing what to spend time doing, how do you, yeah, how do you tackle that? How do you go about it?

Ben Mason: 38:30
There’s a sort of more philosophical level to that, which is, I think, I really value my own time now. I don’t mean that financially, like, how many years have I got left and what do I want to do in that time? And that drives a lot. And there was a kind of like realisation of, why do I want to wait 10 years to live on a boat? I wanna do it now. And I think that saying, that sort of falls right down to day-to-day stuff. Like I wanna enjoy today and I’m value today and choose what I want to do today. I couldn’t imagine going back to not being in control of my every day, really, I really value that. It comes with a lot of stress, financial insecurity, not knowing what you’re going to be doing next week, never really getting a day off because you have to work when the work comes. So there’s a cost to it. But I really value, I love slow mornings. I love doing that. Going like, you know what, I’m just going to sit and have my coffee and, sit for an hour before starting work. I did, I love that sense of freedom it, but you know, it comes with stress and insecurity.

Chris Hudson: 39:48
Yeah, I think the balance is a really important point because, the grass is always greener as a concept. You move, you take a step into these worlds. So you think, okay, I’m living on a tropical desert island. I’m doing this on the boat. What? I dream about a monthly salary sometimes. Yeah, just something, just to know that the money’s coming in then. But I also know I wouldn’t ask not. Well, you’ve got to put it out there like they say, put it out into the universe, see what comes back. Yeah, monthly salaries, what would you love to be doing? On a monthly basis in a dream world. it’s not just like you need the money to pay the bills, but if it’s that kind of thing, you were talking about another startup idea, whether it’s freelance work or something else, how are you forming that in your mind? And you, are you working actively to try and push towards that dream next?

Ben Mason: 40:34
There will hopefully be another startup quite soon. I’m working on something with a couple of people, came sooner than I expected. I was really burnt out after the last one, after the P2 on a COVID because I ended up working office hours in advertising. Stuff and then evenings and weekends on the pizza business. And we had 65 employees. So it was like it was intense and it took some time to recover from that. And I guess the boat became the new startup as in. It was challenging and all consuming and risky and, it was ticking the same boxes and, set a lot of the same feelings, but I just still have that sort of ticking inside me. And yeah, still have that drive. it probably will affect if it goes well, it’ll affect our sailing plans. I’ll need to be on the right time zone. I need to be more available, but you know, can I build from this, we’ll build a remote business and we, Everyone will be remote. It’s very different. It’s one thing turning up as like the creative freelancer. Yeah, I live on a boat and it makes me interesting and perhaps more hireable to like, can I manage a team of people that are living on a boat and motivate them? And it’d be cool. Don’t know, but I hope so. And I believe so.

Chris Hudson: 41:52
Well, they made the radio station on the boat, didn’t they? So you might be able to get some other people who also live on boats to converge in this and in a great space at a great time. And there could be a sort of Armada flotilla scenario.

Ben Mason: 42:08
Well, I remember listening to a podcast with the founder of 37 signals who make base cap and other things. He’s big on remote working. And he said. You either need a majority site based company or you need a majority remote company. You can’t blend the two, it’s too difficult. Whatever money you save on that office downtown, spend it on travel to bring people together. And core teams meet once a month, departments meet once a quarter, and the whole company gets together once a year. I thought that was really insightful. And who doesn’t want to work for a company that’s going to Fly them to cool places and spend money on that rather than a really expensive office in the middle of London, baby

Chris Hudson: 42:49
Yeah, exactly. Yeah. I mean I think reinvesting against your P& L It’s you can see it in your new like honey It’s like if that frees up this money then you know, what could we do with it? How imaginative should you be with it?

Ben Mason: 43:00
Yeah. And I think company culture flows down, right from away from the top, whether it’s a, a big established corporate or it’s a startup, you often see the way everybody behaves is influenced by whether it’s the personalities of the founders or the environment or something. But I guess hopefully maybe can build an organisation which is motivated by the same things that motivate me. I don’t know. It’s going to motivate me and my co founders. I’m not sure. But that would be really, really cool to take the same sort of sense of adventure and like it’s possible and see how that thrives in an organisational setting.

Chris Hudson: 43:39
And I think, tying that to the point that we’re making before around putting yourself out there and creating, obviously, I feel that kind of expression, it starts the conversation already, around what people need, what they value, what they expect, where they sit. Where they want to be, what are their dreams, all of that sort of thing can be a bit forced in a usual kind of, let’s sit down and discuss your personal objectives and your personal development plan, in that kind of setting, it can be a bit like, oh, we’ll just talk about the work, but if you’re trying to get to a deeper level and actually engage your employees and trying to build out something that’s Motivating on a higher plane than I think some of the things that we talk about probably help with that,

Ben Mason: 44:13
and I think it comes back to your intrapreneur thought, which is I’ve always preferred laissez faire management styles, entrepreneurial environments where I’m just giving a problem solve and get on with it. And that’s suited my personality and I hate it. Being told specifically how to do something and follow the tasks is to sue me. But I found as a manager, I do the same thing. I give people huge rain and I’m there to support them and they need it. But I really, I get them to drop them and give them as much space as they want to solve it. So I guess that’s organisation that I would like to build because it’s the one I’d like to work in. The one that has entrepreneur spirit at its core of its culture.

Chris Hudson: 44:52
Uh, that’s interesting because like some people don’t always react as well to kind of the open, the open challenge, the open brief, I think, giving people that right as for the right character, it’s a good thing, obviously incredibly motivating. Other people want a bit more direction. So have you found yourself having to manage that a little bit?

Ben Mason: 45:09
I’ve definitely had moments where people have been a bit like, can you just help me a bit more? Can you tell me how to do it? Give me something. Yeah. I remember when we were, We were talking about seating, flexible seating, one of those small things that becomes really important in an office and there was a real hard divide between the people that didn’t mind coming in in the morning and we’re at this time when the agency was growing so fast we actually ran out of seats so you had to get in early if you wanted a seat because there weren’t enough for everyone. Some people found that really stressful and I also thought it was the same people that liked a lot of structure, they liked their seat, they liked their files organised, whereas the other, there was a certain type of person that came in, opened the laptop, didn’t really care where they were perched. Definitely a sort of hard cultural dividing line.

Chris Hudson: 45:53
Difference. Differences. I think you just gotta, yeah, you just gotta be aware of those, those, differences and what people want. That all sounds really cool. I think, There’s probably a point to wrap on here which is, probably just around where, where you are now, where are you going next, what are you going to do, where are your travels going to take you, what kind of work do you want to be doing, anything like that.

Ben Mason: 46:12
So the dream, the dream is get freelance work flowing in steadily to get this boat fixed, spend the next few months sailing around the Bahamas. Probably till the winter, Bahamas, maybe across to Mexico. I’d like to sail across the Atlantic next summer and next spring and come back to Europe and then be based in Europe for, I don’t know, a few years, depending on what happens with work and start ups and stuff. Just cruising around the Med, more seasonal over there, so find somewhere warm and cheaper for the winter. To winter the boat and then spend the summers cruising around the med. And then who knows the long plan is to sail all the way around the world over the next decade. I have no idea how I’ll balance that with work because I may have internet connection in the middle of the Pacific, but I’ll be on a completely different time zone to the entire rest of the planet. Maybe you can help me from Australia. Yeah. Swing by, definitely.

Chris Hudson: 47:05
Yeah. We’ll sort it out. Can’t help you with any boat skills, but I’ll give you something else that might be helpful. But yeah, that’s sailing and building businesses. Never thought I’d heard those two things in the same sentence and in with for my working and all the things you described. Yeah, I just really appreciate the chat, And coming on with such an open spirit and, just an open mind to this kind of random conversation. But I think a really helpful one from the point of view of perspective, because we’re all stuck at work. You’re out in an amazing place. I think perspective is really important

Ben Mason: 47:37
sometimes. Stuck at work. Yeah, you’re

Chris Hudson: 47:40
at work. You’re at work. We’ll convince ourselves of that,

Ben Mason: 47:43
but I think I can’t even raise my anchor at the moment because of the lightning strike. So I’m genuinely

Chris Hudson: 47:48
stuck here. But yeah, thanks so much, Ben. And yeah, if you do meet any other interesting people on your travels, pirates or anybody else that you think we should talk to on the show, then definitely let me know. I’ll pass them on. Thanks so much, Ben. Thanks, Chris. Really good talking to you.

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