Globally, the last year has been rife with headlines of major companies demanding employees return to offices full time. Europe, on the other hand, has been a bit slower to adopt the trend. Across the EU, hybrid work remains the most common arrangement for employees whose roles can be performed remotely.
Naturally, wide variations exist between the countries. For example, while the Netherlands boasts nearly 78% of employees working in hybrid or fully-remote roles, less than a quarter of those in Cyprus can say the same. Collectively, fully-remote roles in the EU declined from 24% to 14% between 2022 and 2024.
But amid this power struggle, a new wave of founders is rejecting the idea that productivity and innovation require physical presence, and leaning into the new normal of Digital Nomads. Sam Oliver, a serial entrepreneur currently building his third startup, is one of them.
In the inaugural episode of the 150sec: Beyond the Bubble podcast, Oliver shared how his approach to remote work has evolved, and why he’s not asking his team to clock in at a corporate HQ.
Having founded startups in both Edinburgh and London, Oliver is now leading his latest venture fully remotely, backed by an equally remote team. Proof that building a startup outside of a major tech hub, though not without its own challenges, is entirely possible.
That said, Oliver doesn’t romanticize the digital nomad lifestyle. After taking 52 flights in a single year, he realized constant travel hindered his ability to build reliable enterprise-grade software. “Remote is great,” he told us, “but I think people with a stable base have more output than those constantly moving.”
As his company transitioned from prototype to enterprise-ready product, Oliver saw the value in establishing more consistency, but his team remains remote, with in-person meetups seen as valuable but not essential. “It’s a luxury, not a requirement,” he noted.
In an era when more European CEOs are demanding bums in seats, Sam Oliver offers a compelling counter-narrative: that high-performance, enterprise-grade companies can still be built remotely: a welcome message for other founders building outside major tech hubs.
*As a note, since recording OpenFi has rebranded to Zeus AI.
Transcript:
Brittany Evansen
Okay, so here we are, welcome to the 150Sec: Beyond the Bubble Podcast. This podcast shares the stories of underdog entrepreneurs and innovators who are forging their own paths in emerging European markets and beyond. I’m your host, Brittany Evansen, and I’m here today with Sam Oliver.
Sam is a multiple tech entrepreneur. He’s a property investor, he’s an author, and he launched his first startup at just 20 years old. And we’re going to talk today about his latest venture, OpenFi, but also just about his journey of starting a startup and building remotely, since in emerging markets – you know, our focus is talking about people who are building in places where they’re not working with the kind of networking advantages of tech hubs like San Francisco, Madrid, London, [New] York, et cetera. So you built your first startup, as I understand it, in Edinburgh, and your second in London, and now you’re building entirely remotely. So what inspired you to take this leap to and build a new startup when you’re like not even settled in one place at a time, you’ve been doing a digital nomad life lately, and were there any specific changes that made this kind of decision possible?
Sam Oliver
I definitely think COVID was a huge impact in accelerating remote work. We already, before COVID happened, we had a London office, but we already worked with developers that were remote. So we had a lot of experience working with remote team members. We had an amazing operations director in Venezuela. We had developers in Serbia. We had other team members in Croatia. So hybrid was more what we were accustomed to however, post-COVID it really kind of showed that nearly all roles could quite comfortably be delivered remote. So that was kind of the instigator of being able to have a more remote culture.
Brittany Evansen
And you’ve been in several places over the last year, so you want to tell us about some of those places that you’ve been just quickly, because now you are in South Africa, right?
Sam Oliver
So I really packed up my bags and moved out of the UK in December 2022 and that was when, like formally with HMRC Revenue and Customs, I said, you know, I’m no longer going to be a UK tax resident – I’m leaving the UK. And my first stint was a year in Bucharest.
I chose Romania because we had built a technical team there. So aside from the UK, which country I had visited the most often in my life, so I was familiar with it. There were highlights and low lights. Personally, a lot of things that I like about a city, Bucharest, didn’t have – so it didn’t have good access to nature. It didn’t really have a good expat ecosystem. However, for exploring around Europe, it was pretty conveniently centered to do lots of travel, which I enjoy. And we did build our first version of the software with the team there. So it was also good for work.
It was great. I had an apartment there for a year. It was a little bit tricky with visas, so I had to spend a lot of time applying for the visa there because of good old Brexit making life difficult, which was a bit of a distraction, really, because I think it’s easy to underestimate the amount of visa paperwork. Like there’s a lot of paperwork to have a visa, to stay somewhere.
Brittany Evansen
As an immigrant living abroad – yes, it is no small thing.
Sam Oliver
You know, a lot of queuing in lines at visa offices for exceptionally long amount of time. Eventually, I settled on the fact that Bucharest wasn’t the long term base for me in Europe, and I continued traveling. Even when I was there, I did do a lot of traveling purely because it’s a passion and it’s a hobby, and one of the joys of working online is there is a level of flexibility as long as you’re roughly in time zone and I’ve got good stable Wi Fi, and can meet your outcome commitments, then I think it’s pretty easy to travel.
After Bucharest, I tried a few different places. My objective was to find a long term European base. And when I say long term, I’m thinking with like a five year time horizon. So I have a big spreadsheet with many variables – from lifestyle choices to tax choices to infrastructure choices – to help me pick, and what I spent the summer doing was trying different places. So I drove from Bucharest through Greece and spent six weeks in Greece, and then drove up to Croatia and spent six weeks in Croatia.
I would say that working on a startup while traveling is difficult. It is a bit of a headache. If you’re doing a few weeks at a time and a place and traveling, there is an energy cost to that, and the opportunity cost of that energy is other aspects of your life. It doesn’t have to be work. And if it’s not work, it’s your social life or it’s your health. You know, there’s only so many hours in the day, and there’s only so much energy for output. And if you’re doing a lot of getting on planes and traveling and planning travels and trips and logistics, there’s a cost to that. I realized with both of those places that they weren’t good, long term fits for me – I think probably the biggest thing is community, in terms of like expat community, digital community.
Athens was stronger. Split was very small, very small, not really an expat community there. But I love Greece, but I kind of felt that Greece was fantastic place for a holiday, but it wasn’t where I could see myself building a long term base. And then it came to Cape Town for three months, and Cape Town was a location that was my fourth time visiting, so I know it fairly well, and the digital nomad community here – amazing – I’d say it’s one of the most vibrant in the world. There’s a lot of people that come here to work, particularly during the Northern hemisphere winter. My three month trip was extended to six months, and my sort of ongoing plan is to build a team here, because I think that there is a really good cost arbitrage, and there’s a lot of really skilled, very talented people here. I plan to spend six months of the year in Cape Town and then six months back in Europe.
Brittany Evansen
Oh, wow. So Cape Town feels like it’s the place – you’ve settled on your place, as far as being outside of the UK?
Sam Oliver
I’d say for for a southern hemisphere base, definitely Cape Town. But then when it comes to switching seasons, I haven’t found where, I suspect probably Zurich, maybe, maybe Barcelona, so there’s, I still need to research that. But one of the decisions I took was I decided to pause on the hunting for a European base to really just focus on work. And that was one of the reasons for extending the stay here, was there are inflection points in startups where that little part of the journey is really, really important to get right. And I could tell that we were at one of those with this company, and it was just so important to stay, have a base and focus, and be really focused on delivering the work. So that was part of the decision there.
Brittany Evansen
That’s a great segue, actually. Let’s dig into that a bit more, if you don’t mind, because I think that that’s a really important piece to this conversation, that it is obviously possible to build an online company, to build a startup in a digital nomad lifestyle kind of way, where you don’t necessarily need to have a home base, but it sounds like you’ve actually found a there’s a you’ve hit a point where you kind of needed to have a home base and to be more settled in a particular physical location.
So what was that inflection point? Can you talk a bit more about what that was and why it kind of requires more of a home base and knowing that you have a team that’s also remote. How has that affected, kind of the way you’re thinking about your team and where they’re located now?
Sam Oliver
Lots of good questions. I have no concerns about team being based in other places. I would have concerns about someone being able to be effective and do the amount of travel that I was doing last year. I took 52 flights, so it was a lot of traveling, and it was mostly fun. Not I wasn’t flying around for meetings all the time. I was flying around because I enjoyed traveling, and so no problem with remote. But I think that people who are remote, who have a stable base, even more our output than people who are nomadic and who are dotting around. I think that is more difficult.
In terms of the inflection point, sort of enterprise entrepreneur business, there’s so many variables of what that can mean, and specifically what I’m interested in is building technology. So kind of business that I’m in is not running an online coaching business or running an agency or reselling someone else’s software, or scaling drop shipping – all which can be wildly profitable and successful businesses – but I’m specifically in technology which can then scale.
I think that SaaS has got a lot of difficulties in that building technology is very expensive, it takes a lot of time, and it’s very hard, and the difficult part is to tie up the feedback loop of what the customer wants to buy with what you can build and deliver to get that product market fit. Maybe the analogy would be it’s kind of like you want to sell a house, but to build the house is really, really expensive, and it’s going to take a lot of time, so you have to try and get one room built and sell sell that to a few customers, and then figure out what they want the rest of the house to look like. It’s complicated and it’s hard, and it’s why the failure rate is so high. It’s also why most SaaS companies do require to raise funding, because it’s going to take 6 to12, months to build a product to an enterprise level where customers can really buy. And yes, I love high fidelity mock ups. I love the Google Design Sprint, I love the Lean Startup, and I love all the concepts of being able to do rapid iteration of learning, but when it comes to an enterprise customer taking on a product and actually putting it live on their website, they need a reliable product. It has to have gone through compliance, and you have to have actually built it.
I think the Silicon Valley “fake it till you make it” has real limitations. And the reality is, you have to build something to be able to sell it in the software space. And yes, you can do a lot of research to make sure you’re building the right thing and getting customer feedback, but the rubber only meets the road when you’ve actually got a working tool, and by that point you’ve already spent a lot of money building and developing it.
The inflection point for us was really getting to a stage where we’d got out of that feasibility and analysis. We were building an enterprise-ready production tool. We had a really big PLC customer, and I just knew that to be able to onboard that customer, deliver the service, and get it really live, just needed, like, reliability, consistency and focus. And if you’re speaking to the chief technology officer of a company that turns over half a billion pounds a year, you can’t be in a cafe somewhere with dodgy Wi Fi and people walking around in the background, you know you need to be somewhere like serious where you can hear them, and they can hear you, and it’s reliable. So it just had to be that sort of commitment.
Brittany Evansen
You talked a lot about how expensive it is to build SaaS and like reliable enterprise ready SaaS. So, how was fundraising when you were in the midst of traveling? Do you feel like – you obviously have a background where this is your third startup, you sold your second startup, like you have a successful background where I imagine that investors a) if you, if you already knew them, right, you already have a great relationship, or if it’s a new investor, you kind of have this great background that you can point to this success metrics. But for a first time founder, do you feel that being remote and kind of being in this digital nomad lifestyle? Do you think that fundraising could be a difficult experience for a first time founder, versus, you know, someone in your position?
Sam Oliver
When I think about all of my investors, I haven’t actually met all of my investors in person, but nearly all of them I’ve met in person, and I think that meeting in person multiple times is often what is needed to build that credibility. I love the expression “you can’t email a handshake.” You know that sort of if someone is trusting you with 200,000 pounds, I think doing that fully remotely might be difficult. It’s not to say that you can’t maybe close it remotely, or you can’t progress it remotely, or start it remotely, but in terms of really standing out and proving that you’re an actual physical human being, and you’re real, and you’re not going to disappear off with the money. I think that’s important
Also people, in my experiences, most investors have got their geographies that they’re comfortable in. Like, if you’re an angel investor in Singapore, you’re going to be comfortable investing in Singaporean-based startups. If you’re a London angel investor, you want to invest in a UK Limited business. So there’s exceptions to the rules, and the bigger you are, the more capital you can get from other places, but I think for early stage, it’s going to be difficult to fundraise outside of your geography.
Brittany Evansen
We’ve kind of been talking a lot like around OpenFi and your experience of building OpenFi, but tell me a bit more about OpenFi, like, let’s talk OpenFi – talk about the business, how it’s going, and why you decided to pursue this project after successfully selling your last enterprise.
Sam Oliver
I think the first part is there’s a real joy to building. iI’s very creative, and you do a lot of problem solving, so there’s just intrinsic satisfaction from working on something that is interesting and complicated and rewarding. It’s very fun to be working on the most cutting edge, newest technology that’s really interesting. And I think that for me, the big motivator was seeing the technology overhang, and what I mean by that is about 98% of the websites on the internet have a contact us form, and then where an email goes into an inbox, which may or may not get a reply at some point in time, if you can get past the spam capture code. That is the customer experience there and then at the far end, you have got these very, very good quality AIs that can answer all sorts of questions and help customers in all sorts of ways. And I think that overhang is where operators like myself and startups and incumbents as well, but they’re looking at, how can we take that customer experience and leverage that new technology to make it so so much better?
And Mark Zuckerberg talks about this. He says that in 10 years, every website will have an AI on it, and you’ll probably have your own AI. You’ll have all your data in a solid wallet which can securely communicate from your AI to the other company’s AI to make whatever you want to happen happen. And I think that will be 100% what happens. Experience is going to be not 10x better, 100x better. I think the friction is going to be lower. I think the trust is going to be higher. But these complicated systems don’t just happen. They have to be iterated and delivered.
So what we are really looking at is the very top of the funnel. So AI live chat on a website – how can we, and there’s two really core components to this, the first is customer experience. How can we make sure that your customer has an amazing experience with your brand? They come onto your website and they’re heard, they get answers. The answers are intelligent. They don’t get frustrated. They’re able to do what they want to do. And the second component is really about the commercials, and it’s totally tied to the first if you are treating those customers well, you’re making it easy for them to do business with you. Well, your balance rates go down, your conversion rates go up, all of your commercial metrics are improved, and they’re done efficiently because you’re scaling a technology rather than scaling a team of people to deliver that results. So it’s super high margin change, and that’s exactly what we are focused on.
Brittany Evansen
And for the listeners who don’t know what’s the elevator pitch of OpenFi, can you describe just in a few sentences what you all are doing and the service you’re providing?
Sam Oliver
So we work with service providers and product companies, and we provide an AI live chat agent. What we do is we create a custom knowledge base so it knows all of your company information, and then we create a sales script so it understands how to pre-qualify customers. And our objective is to provide a higher customer experience and book in more calls for pre qualified leads to your CRM.
Brittany Evansen
And when you were starting off, how did you recruit your team? So you have a really strong team. Obviously, you’ve built this, this technology, and they have been working in different places, right? They live in different countries. So how did you go about recruiting, recruitment at the start?
Sam Oliver
So in this business and the last business, we actually started working with a dev agency, and this has pros, and it’s got cons. On the one side, it is fast. You don’t need to go and hire a CTO and work on equity agreements, you know, make sure that you’ve got enough money to pay their salary for a year, so they’re comfortable leaving their job to join you. It gets rid of a lot of boundaries and barriers.
The other thing that is, when you’re building a technology product, one person can’t do it all. It’s a team sport, so you know, you have to have someone who’s reviewing the code and testing the code, and one person can’t do it. And one of the good things about working with agencies is they’re teams, and they’ve got the infrastructure to have specialists on front end, back end testing Q and A. So for initial ideation, I think working with an agency worked really well for us. It helped us get proof of concept that proof of concept helped us close funding. It was faster.
The difficulties are both times with us when we then had proof of concept and we’d raised funding and we had initial customers and hired a technical team internally full time, you then kind of start from scratch. So you – in our use case, we basically rewrote everything again in slightly different technologies.
And you’ve got a leg up because you’ve got the learning of what went wrong with the like alpha version that you built. But you are then spending money again, kind of end up rebuilding what you’ve already got, but you’re doing it in a way that’s more scalable and more reliable under an internal team where you really own all the IP.
Hiring technical people is actually very, very difficult. There’s definitely an advantage to being a serial founder, because you know those people, and they know you, and they’ve got credibility, and people will come and join you, and I’ve worked before. But other than that, we have had success working on platforms like Upwork. A lot of the team members I’ve now worked with for five years plus, I originally met on Upwork. Working with agencies, yes, it is more expensive, but you can meet great people. I don’t think there’s a silver bullet. I think in general, recruitment is really hard.
Brittany Evansen
And you obviously bring that team together from time to time, since you’re all located remotely to be in the same space. So how do you go about planning those – when you meet and how often you meet? Do you feel that there are particular times, for example, you previously mentioned this inflection point, when do you find that you kind of plan these gatherings to make sure everyone can be together in person, face to face?
Sam Oliver
In my previous business, I had a software engineer that I worked with for seven years, and I never met. Like I don’t necessarily think you have to. I think it’s maybe more of a privilege and a luxury than a requirement. But I think for creative and strategy and planning work, it is lovely to get together as a team and just as social humans, it’s nice to get together as a team, but I don’t actually think it’s mandatory.
I think for us, the objective is at least once a year, ideally twice a year. The difficulty is it just is very expensive. If you’re flying five people to a location and paying for accommodation, food – it adds up, and as an early stage startup, you have to be so cost conscious. So, yes, it’s nice to do, but I don’t think it’s a must.
Brittany Evansen
Fair. Well, you are the CEO, the founder. You know, it can be lonely at the top to be the person in charge, and it can be hard, you know, like this business is very different from your last business. So who do you turn to? You know, what kind of communities – you mentioned before that community was one of the most important things when you were looking for a place to kind of settle down for a more extended period of time than just a couple of weeks – so who are the people that you know, if there are individuals or maybe organizations or groups that you want to shout out and, you know, kind of tell us about that have really helped you as you’ve kind of navigated this latest endeavor?
Sam Oliver
That’s a good question. One community that I’m part of is the ICE group in London, the International Conclave of Entrepreneurs. And I think, for London-based founders, they also have a chapter in Lisbon. It’s a fantastic community. It’s just tech founders, and there’s a lot of amazing people, really good advice.
And one of the great things is – I think that advice has a limited shelf life. If you are speaking to a CEO who founded a company 15 years ago, their advice is going to be much less relevant than someone who did it eighteen months ago or three years ago. That time period has a huge impact. And I think it’s very easy to, particularly on social media, see all of these, you know, CEOs of companies that are massive, and they’re giving all this advice, which you think you have to follow, but actually things change so quickly that the advice that they’re giving worked 15 years ago, but it could be totally wrong today. And I think the ICE network has a lot of founders who are in the startup and scale up stage so that they experience their selling, their sharing, and the tools that they recommend are really like the cutting edge ones. I think that makes a big difference.
Brittany Evansen
And how have you navigated finding community and these new places that you know, maybe, maybe you’ve visited before, but like, when you’re spending an extended amount of time there, it’s very different experience. Do you have any advice for a founder who’s maybe in a smaller, you know, not outside of a tech hub, who’s looking to find that community? Like, how? How do you go about finding community when you don’t have community when you don’t have one that’s kind of naturally built in?
Sam Oliver
Yeah, that is difficult. I think that there are more co-working spaces now than ever before, and a lot of them do a really good job of bringing that community aspect together. I would imagine that in most, even smaller cities have some kind of a co-working space, and you just go there and you’ll meet people, and you can chat with coffee.
There are also some places that have got really good WhatsApp groups, and it’s a little bit hard to find. You have to do a bit of research online. But once you get introduced to one, there’s a myriad of social WhatsApp groups, and they can be really good for finding out events, what’s on, joining meetups. It’s can be a bit of a double edged sword, though, because I think a lot of the times you have limited capacity to do all these nice things, you know, like, especially if you’re in a really busy stage, you’re not going to go to five different meetups a week. You might not even do one a month, because you’re busy head down, focusing. So yeah.
Brittany Evansen
True. And to finish up, a little lightning round question – two questions. So you’ve mentioned that you enjoy reading sci fi book that you recommend that other people read a sci fi book that everyone should read, I’m putting you on the spot, so no pressure.
Sam Oliver
That’s a good question. I…The MurderBot series by Martha Wells was one that I really enjoyed.
Brittany Evansen
All right. And as someone who has been living outside of your home town for many, many years, is there one dish or thing that you miss that you you know that’s like the home if it tastes and feels like home.
Sam Oliver
I think that in Edinburgh, we do a very good cooked breakfast with haggis and black pudding and tatty scones, and we can’t really get that outside of the UK, so definitely not healthy, but I miss that.
Brittany Evansen
Fair enough. Thank you so much for your time this morning. I really appreciate it. I think this has been a really helpful conversation for other founders who are trying to navigate remote team building and work and also you know building the plane as they fly, I think is the idiom. But anyway, thanks so much, and appreciate your time.
Sam Oliver
Pleasure, thanks for having me, Brittany.
