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Fintech’s Most Ambitious Startup – Constantinople.

March 16, 2025 · Hosted by Dexter Cousins

In this episode of Fintech Chatter, host Dexter Cousins speaks with Di Challenor and Macgregor Duncan, co-founders of Constantinople, about their journey in building the Operating System for banks. 

About Constantinople

Constantinople is the most ambitious startup in Fintech, tackling the most complex problem in Fintech, rethinking how banks become fully digital. Constantinople is a banking operating system, the AWS for banking, managing all infrastructure and operational aspects of a bank: from Customer experience, Banking products to Features, Risks etc.

How Do You Build A World Class Fintech From Sydney?

Tune in as Mac and Di discuss the challenges of building a global fintech from Sydney. They share their secrets to winning banking clients, the importance of establishing trust, and the strategies behind their successful capital raising efforts. 

We revisit our first interview in 2023 and talk through the challenges and learnings of the past two years.  As they look to the future, they share their vision for Constantinople and the endless quest for excellence.

Chapters

00:00 Introduction to Constantinople
04:09 The Evolution of Banking Technology
07:17 Challenges in Client Acquisition
10:10 Building Trust and Credibility
12:53 Creating a New Category in Banking
16:04 Navigating Capital Raising
19:03 The Importance of Execution
25:02 Scaling the Business
34:08 The Importance of Documentation in Scaling
36:49 Driving Excellence in Early Stage Companies
42:45 Commitment to Excellence: Attracting the Right Talent
49:07 Identifying and Filling Skill Gaps
53:15 Future Vision: Building a Multi-Tenanted Banking Platform

Links from this episode.

Di and Mac on Fintech Chatter.

Mentioned in this episode.

Full transcript.

Lightly edited for readability — filler words removed, wording otherwise unchanged.

Dexter Cousins
What happens to a fintech after it raises a record seed round? I find out in today’s episode of Fintech Chatter. Today’s guests are the co-founders of Constantinople, Di Challenor and Macgregor Duncan. I’m your host Dexter Cousins, founder of Tier One People, the executive search and recruitment firm that helps high-growth fintech ventures attract and hire exceptional talent.

Constantinople last featured on the show in June 2023, barely a year old, coming out of stealth mode and announcing a record A$30 million seed round. At the time I put my reputation on the line saying Constantinople would become an Aussie tech giant. For me it was simple: they had tier one founders, tier one investors and tier one people. For listeners who want to hear that first show, I’ll put a link in the comments. Today we’re talking about what’s happened in the last two years — the journey of fintech founders three years in, what they’ve learned, what they got right, and what they wish they could try all over again.

Without doubt, Constantinople is one of the most ambitious projects in fintech globally, if not the most. Di, Mac, welcome to the show. Mac, you’re coming back, but Di, it’s your debut on Fintech Chatter. For those who didn’t listen to the episode from a couple of years back, tell listeners a little about Constantinople.

Di Challenor
Constantinople is a complete banking platform. What we’ve decided to do is help banks with what’s under the surface — building a banking platform that covers the totality of what a bank needs to run, from channels all the way through the product systems, operations and all the components.

We really want to see bankers get into the business of meeting their customer and member needs. Often as bankers we get dragged into things that are probably important but really don’t change the customer experience. So we’re looking to enable our bank clients to have market-leading experiences — the best banking capabilities they can have — and, at the start of our journey, to enable a number of smaller players to compete across the market and satisfy what customers need from a banking perspective.

Dexter Cousins
We’ve seen complete operating systems for so many other industries over the decades. Why hasn’t there been one for banking?

Macgregor Duncan
To pull it up a bit, there was a great article Matt Levine wrote in Bloomberg a couple of years ago. He’s widely considered the world’s leading commentator on banking and financial services — perhaps with the exception of Dexter.

What Matt said is that for various historical reasons, every bank today is vertically integrated. It runs the business of being a bank, but it also runs all the tech and ops. And he said that if you were redesigning banking today, in 2025, there’s no way you’d design it like that. You’d have banks focus on what they’re good at — the business of being a bank: enabling their mission, serving customers, managing the balance sheet, funding themselves, managing regulatory obligations. And you’d have large, well-run tech companies manage all the commoditised or undifferentiated aspects of being a bank.

No disrespect, but if you go into any bank in the world, no one walks into tech and ops and says, that looks like AWS or Stripe. A bank’s DNA is mostly around how they manage risk, how they fund themselves, how they manage the balance sheet, how they price, and particularly how they serve their customers. It’s not around tech and ops. That was the opportunity we saw — to step in and manage all of that on their behalf.

As to why it hadn’t been done before, there are a handful of reasons. A business like ours is completely enabled by public cloud; you can’t run the breadth of our service other than on cloud, and we’re probably five to seven years into banks being really comfortable running a lot of their applications there. And we’re moving into an AI world where a lot of the operational services that have historically been done manually can now be done through software, and in particular through LLMs. That’s a massive shift in how banking will be done.

So people have long thought there’s a big opportunity here. Practically speaking, I don’t think you could actually execute it until more recently.

Dexter Cousins
When I was last here you were 12 months into the business, and it coincided with a big announcement: a record Australian seed round. You’d been in stealth for 12 months and I think you were about 50 people. Where’s Constantinople now, in March 2025?

Di Challenor
In March 2025 we have four clients. Great Southern Bank was our foundational client, and we’ve been really fortunate to sign three other clients on the platform. We’ve gone into multiple geographies — we’re operating in Australia, New Zealand, Singapore and India — and we’ve taken the workforce from 50 people to 150. So it’s been a significant growth phase.

Dexter Cousins
Four clients, four geographies and 150 people. What have been the big challenges since I was last here? Getting three clients, for a business of this nature and with the sales cycle involved, can’t have been easy.

Macgregor Duncan
Before Di answers that — the really key thing is that these are not standard enterprise clients. As Di said at the outset, we are running these banks end to end: channels, so mobile and web; product; ledger; all operations; customer service; compliance. We manage all of that on behalf of our clients. It’s a daunting exercise to do that for a single bank, and now we’re scaling it across four — and of course we’re in advanced discussions with a number of others. The platform we’re running is really complex.

Dexter Cousins
To double-click on that: the typical sales cycle for something much lower down the scale is still 12 to 18 months of wining and dining before a contract gets signed. You’re now in implementation with these businesses. How have you accelerated that sales cycle? It’s the biggest frustration every one of my clients has, and it’s probably the hardest role for me to fill when I’m recruiting.

Di Challenor
As an aside, it’s actually a really enjoyable process to meet bank executives, understand their challenges, and hopefully give them a pathway. So yes, it’s a significant undertaking, but we look at it as: how can we add value?

Our approach has been twofold. One is to constantly provide proof points around our progress. We’re a three-year-old company, and as Mac articulated, we’re asking a bank to move their entire bank to us. To do that we’ve got to build trust and credibility, and the best way is to do what we say we’ll do, and be really transparent about how and when we did it.

We got Great Southern Bank into market when we said we would. We delivered our mortgage capability when we said we would. We’re now making enhancements to the platform when we said we would. What’s really important with our clients is that we keep delivering, and that’s what’s enabled us. I wouldn’t say we’ve shortened the sales cycle — I guess that’s the outcome — but proof points are something a CEO and a board can get really comfortable with.

Macgregor Duncan
We’re not a marketing-led company. We have possibly the shittest website anyone’s ever seen —

Dexter Cousins
I think I’ve done the most marketing for you.

Macgregor Duncan
With a business model like ours, execution is paramount. As Di said, you have to stand behind what you tell people you can do. It’s not about a sexy website or amazing social marketing — those things can create some froth. But when you’re selling to bank executives and boards, and asking them to make the biggest decision in the history of their bank — moving their entire customer base and operations onto our platform — there’s only one thing they’re looking for, and that’s confidence in our ability to execute and deliver.

Di Challenor
And we treat it as a partnership. This isn’t us selling a capability; it’s a deep partnership. That’s really important to us, because we’ve been on the other side. We’ve been bank executives who’ve been let down, trying to explain that inside the organisation. We don’t want any of our clients to have that pressure. Running a bank, being on a bank’s executive team, working in a bank’s operations — these roles are complex. Banking is hard. So we look at this as a partnership, and we do what we say we’re going to do.

Dexter Cousins
One of the biggest distinctions I’ve noticed between the culture of a fintech and a bank is that in a bank, if you make that kind of mistake, it’s career over. In a fintech, as long as you’re accountable and you fix it, it’s treated as a learning experience.

Which leads to what I wanted to ask next. We’ve had a decade of failed experiments, froth, broken promises and hype from the fintech industry — a few successes, but a lot of oversold promises. How hard has it been to convince potential customers that this is the real deal?

Macgregor Duncan
The first thing is that we’re creating an entirely new category. No one else globally has done what we’re trying to do — a fully managed service across all tech, all infrastructure and all operational activities. So the first thing we’ve needed to do is explain to the market that our offering is completely different. We’re not your regular tech vendor. We’re a platform for long-term partnership. That’s taken a while.

What we typically hear from bank executives is that conceptually, what we’re offering makes all the sense in the world. Sometimes we hear that it’s inevitable that in a decade the industry will be structured along the lines we’re outlining: banks focus on the business of being a bank, and large, well-run tech companies manage the commoditised and undifferentiated — much as AWS manages the commoditised and undifferentiated parts of storage, compute and security.

So we don’t have much difficulty convincing banks that Constantinople is the future. But as one bank CEO jokingly said to us: I’m in a desperate race to be fourth or fifth onto your platform. I don’t want to be the sandpit. I don’t want to be the first to migrate my entire bank onto Constantinople. I want to see one or two others go first, and then I’ll have the confidence to move.

The position we’re now in, as Di said, is that we’ve established proof points with four clients. We can go to banks that have long expressed interest and say: you’re not first. Great Southern Bank is live and in market, and we have three other clients. So we can methodically de-risk what a migration onto Constantinople looks like from a bank’s perspective. If you’re a bank CEO or board, it’s easy to get excited about what Constantinople offers, but you’ve also got to mind all the risks. Methodically de-risking that has been critical for us over the last 12 to 18 months.

Dexter Cousins
I want to talk about the other side of the equation. I say this with a lot of respect for people trying to tackle this problem — three or four people in a shared office in Bondi going into a bank CEO and saying, we’re going to fix all your problems. A lot of people have tried that approach, and they get laughed out of the room.

One of the claims where I put my reputation on the line after our first podcast, Mac, was that if you’re going to raise serious capital you’ve got to be solving really big, bold, complex problems — and you can’t do that with a couple of people in a WeWork. You raised just before the market tanked and capital dried up. But what I came away with was: the capital is there, but it’s only going into big, bold global problems with a huge TAM. We’ve since seen aggregate capital numbers increase, but concentrated on a smaller group of businesses tackling big global problems. Tell us about the recent raise and how it came about.

Macgregor Duncan
I’m going to let you do it, Di, because I got the last one.

Di Challenor
No — that’s what he’s just so good at.

I come from a banking background, so going in and talking about where you’re taking your business, the capital you need and the boldness of the idea is, I think, compelling. But because we’ve gone from seed to our Series A, my view is that we were able to demonstrate what we’d delivered. I don’t think we would have raised that money if we hadn’t met the milestones we’d set ourselves.

It comes back to clients. When you’re running a banking platform, it’s so important for our clients that we understand the regulatory perimeter they operate in. And for our investors, we’re able to show that we can meet what the market needs, that we understand the market, and that we know how to position ourselves and what it takes to build the company we’ve built and where we see the future. So we could say to existing investors, and to the new investors who joined our cap table, that we have delivered. That puts you in a really good position as you move through the stages of capital raising.

Dexter Cousins
I know it sounds a little trite, but this is just what you do in business. When I was starting out in my career, you’d put on a suit and ask your bank manager for a loan to get a business off the ground. What you fundamentally needed was a business plan and milestones. Why do you think that’s got a little lost among people going out to engage with investors?

Macgregor Duncan
A couple of things. Firstly, we’ve never seen capital raising as an output in itself. Sometimes you see early-stage companies think that’s the game they’re in.

Dexter Cousins
Nobody ever announced a bank loan on LinkedIn.

Macgregor Duncan
But that’s not the game. The game is building a business. Capital is just an input that lets you do something. So we’ve never wanted to be known as a company that’s really good at raising capital.

Dexter Cousins
It’s quite a paradox, given you’ve raised more than anyone else in the last couple of years.

Macgregor Duncan
But investors are looking for substance — for execution, and the proof points Di mentioned.

The other thing that may have set us apart is that we never ran an active process. We were really deliberate about who we wanted to work with. We spoke to Paul Bassat, we spoke to James Cameron, we got on extremely well with Sachin from Prosus. We were much more deliberate about finding the people we wanted to partner with for a decade to build a company together.

We have friends running companies who say their favourite investor is, I don’t know, Tiger — they gave us 100 million and we’ve never heard from them since. That’s not our mindset. When we partner with people, we want a real partnership. We’re on the phone with Paul and James and Sachin all the time. They’re actively involved in building our business — in our sales process, meeting chairs and CEOs. They’re not just providers of capital. So it’s not a transactional relationship, and I think most investors are looking for that too.

Dexter Cousins
It’s interesting you mention that, because there’s so much out there about how terrible VCs are. It’s like recruitment: you’ll always find bad recruiters. But what you’ve just touched on, Mac, never gets talked about — the congruence not just between the investors and the money, but what you’re going to do with it, what the plan is, what it’s for and what the milestones are. What we keep seeing is money raised and then spent on hiring people, and I think that fed a VC model of how do we keep deploying capital to earn management fees, rather than how do we return money to investors and create value.

Macgregor Duncan
Just on that, one thing people misunderstand is that within a venture firm, everyone talks about portfolio diversification. The firm makes lots of bets looking for the outsized power-law return. But that’s not what it looks like for an individual partner. Paul or James or Sachin are probably making one new investment a year, so that investment is very meaningful for their career. It might not be meaningful for the fund, but for that partner it’s extremely meaningful.

So it’s unrealistic for a lot of early-stage founders to think it’s easy. You need to convince that partner that you’re the one company they back. They might talk to 300 or 500 companies a year — why are you the one? That’s a very high hurdle. When people see it that way, it’s easier to understand why it’s hard.

Dexter Cousins
The VC industry is a lot like recruitment in that it doesn’t do itself any favours. I don’t advertise, because I don’t want to reject 999 people — telling 999 applicants to get lost isn’t good for a brand. And the “give us your pitch, let’s do a pitch night” approach needs a lot more discernment at the top of the funnel. Dispense with the pitch nights, and get really discerning about who qualifies for a conversation.

Macgregor Duncan
If you look at the bigger fintechs — Square Peg has Airwallex, Zeller, Athena and Constantinople; AirTree has us too, and Zepto — every one of these companies was founded by people who came out of banks. It goes to what Di said earlier: it’s really hard to operate a business inside the regulatory perimeter, and you need to know what you’re doing. So fintech may be quite different from other early-stage sectors. In Australia, the big fintechs are typically founded by people with 10 or 15 years’ experience, and I think that’s critical.

Dexter Cousins
You named all those companies, and I know the founders. After my first meeting with each of them I walked away instantly impressed — not necessarily because of what they’d done, but the whole package: how they conduct themselves, how they communicate, their work ethic, their values and principles. They ooze talent. My clients say, you’ve got to meet this person. That gets talked about a lot but isn’t executed well: how do you actually assess the individuals you’re investing in, beyond the gut feel of “they went to Harvard”? Their principles, values, work ethic, their views on leadership and how you build businesses.

It’s also becoming clear there’s a movement away from working from home, particularly for businesses in growth and creation phase. More and more data says that if you want to build a business, you need people in the same building. How have you found the growth from 50 to 150? When I was here the office was packed and buzzing. There are still a lot of people here, but now there are 150, and the growing pains typically start around 50 to 70 — we thought this was easy, maybe it isn’t.

Di Challenor
Scaling a business is probably one of the most challenging things for a founder. As I said, we’ve gone from Australia to four geographies. So for us it’s the ability to communicate our vision, and how it translates to what individuals do every day. We communicate, communicate, communicate. We’ve got so familiar with our own words — we say the same thing 15 times, because people hear it differently, and it has to be repeated before it becomes part of how they think. Communication has been key.

The other part is good documentation. We’ve definitely got better at it and need to keep improving, because if you’re running a workforce across four locations, everyone has to understand what things mean in detail. On a Teams call people have maybe 15 minutes of attention, so you have to back it up with minutes and documentation.

Going from 50 to 150 has been an interesting challenge. Have we got it completely right? Probably not, but we’re doing much better than we expected. We’re lucky to have strong managers in each location — teams in Singapore, India and New Zealand. One-on-ones are really important in our company. So is performance management — not just to give feedback, but to ask how people are going and how they’re feeling. Two-way feedback. There are things around the edges we’ve put in place to move the company in the right direction.

We plan every quarter, getting the whole company together. We write a five-to-ten-page memo about what the company needs to achieve that quarter. It takes time, but my gosh — everyone can go back to that document and say, that’s what Mac and Di said we need to do, these are my key objectives, am I tracking?

And every week, a very small thing: we send a message to the whole company every Sunday. It’s not an email — sorry, I always say email. It’s a Slack message. I’m still a banker at heart. It shares our priorities as CEOs and gives people themes: what we’re thinking about, what’s happening in the market, how clients are feeling. People look forward to it, because it helps them check they’re aligned with what the company needs.

We’re fortunate to have run large teams across multiple geographies in our careers. But it’s so hard to describe going from just the two of us to 150. It’s so many little things, Dexter.

Dexter Cousins
This might sound odd, and you might wonder why I’m making such a big deal of it, but you mentioned documentation. This is our 210th founder interview. On Friday I had coffee with an old client who was episode three — five years to the day — and he’s just successfully exited his business. He said something at the time that struck me as much as what you just said about documentation, and that you’ve also reflected on: we don’t have a one-year or five-year strategy. We have a 90-day plan and a ten-year vision.

And on documentation: in 210 interviews, not one person has said they had to document everything in order to scale.

Di Challenor
Our team is amazing. Every Jira ticket is clearly documented, so Mac and I can go in and review them — what the product managers have given the engineers, what the status is. That takes a lot of effort, but the payoff is a better-quality outcome, with no second-guessing and no “did I hear that right?” It’s so critical. We can get better and better at it, but it helps a company move forward. There’s nothing like having it written down. And as the writer of some of that communication, it forces you to think. A PowerPoint or a Confluence page is fine, but you really have to think it through, and that creates a lot of consideration — a lot of excellence — in the company when you put real thought into what you need people to do.

Dexter Cousins
We’re going off on a massive tangent, but this is a really important point, Di. Back in 2010 I was working with one of the top 20 ASX-listed companies, and they had a huge issue, as everybody did, with Gen Y — why they were leaving after three or six months, and why they couldn’t solve problems they didn’t even recognise as problems. They commissioned a heap of research, and what they found was that Gen Y was the first generation to have the internet at school.

When we were at school and got an assignment, you had to go to the library, get the books, read, synthesise, write it down, scribble it out, write it again, and get it back with red pen all over it. That whole process built critical thinking. Then it became: here’s an assignment, I’ll Google it, put it in a deck, copy and paste. It looks fantastic, reads great, you get top marks — but you’ve done none of the mental muscle-building.

Fast forward to now, with AI and ChatGPT, and businesses are finding critical thinking just isn’t there, because people are ChatGPT-ing everything. So documentation sounds banal, like something that won’t move the needle, but it’s one of those things that never gets discussed, and it’s critical to a business’s success.

Macgregor Duncan
One other thing I’d add. When you look at the high-level markers of us as a company, it all looks like a romantic journey. It’s much, much harder than it looks.

The way I’d describe it: people, and companies, naturally want to operate at room temperature. Everything wants to find its natural level. But in an early-stage company, if all you’re doing is operating at room temperature, you’re no different from any other company. Early-stage companies need a massive injection of energy and heat to amp things up and deliver at a velocity that’s really abnormal. That’s the secret of early-stage companies.

But it takes an enormous commitment from everyone — the energy and heat to demand excellence of people when the natural inclination is to revert to the mean and do just enough. That’s the really taxing part. In every meeting and every engagement, you have to seek out confrontation. I don’t mean aggressive confrontation. I mean pushing people to do what they don’t want to do: that’s not good enough; you said you’d do X, I want you to do Y. Pushing the company relentlessly, every day, is what it takes to build something different from what’s already out there.

Dexter Cousins
I think that’s why there’s such a heated debate about working from home. I’m a big proponent of behavioural economics, and taking all the study I’ve done and applying it to 25 years in recruitment — assessing leadership, seeing the cultures that work — the reality is that people with that drive and commitment to excellence are maybe 10% of the workforce. The other 90% aren’t lazy, and yes, you can trust them. But as you said, they go to the baseline, and the baseline is: what is everybody else getting away with? That’s not casting aspersions. It’s how groups behave, and companies are groups. Every great leader works by the mantra that the behaviour you walk past is the behaviour you accept. People have to be honest with themselves: am I committed to excellence, or do I just want to pay the mortgage? If it’s the mortgage, that’s fine — there are plenty of places for that.

Macgregor Duncan
The secret to success is no secret. The more things change, the more they stay the same. That’s why management books from the early 20th century are still deeply relevant — it’s human psychology. However the tools change, however companies organise themselves, whatever the ways of working — everyone delivers in an agile way now — the psychology stays the same. And that’s the part that takes an enormous amount of effort.

Dexter Cousins
You see that in India. The hunger, the capability. I was in Bengaluru in October for the first time in about 11 years, and I was blown away that anyone with a smartphone had a business. At a restaurant, our waiter handed us a QR code and said, can you leave me a review — not the restaurant, me. It was prophetic. I said to my kids, this is what you’re up against. You’re not competing with the kids at your school; you’re competing with everyone in the world for a job.

That’s what’s incredible about building a business outside your home market — how the culture evolves, and gets enhanced, for better or worse, by the countries you start operating in.

Di Challenor
For us it’s been enhanced, because we have a workforce that’s really dedicated to what we’re trying to do, with a strong face-to-face culture here in Sydney and in our other locations. Our New Zealand team works super hard — they’re passionate and excited about the opportunity. Singapore and India are more our development centres at this stage, with leadership in each, and they’ve really started to lift the company. We get great engagement at our Friday afternoon all-hands, where the whole company dials in, and we’re starting to share parts of the local cultures across the company.

It’s so exciting to sit here in Sydney building a global company. It’s incredibly fulfilling. One of my personal dreams, and I’m sure Mac’s, is to show the world you can build great companies from Australia. But we also recognise we’re not the place for everyone, because we’re trying to do something really bold and ambitious, and we’re not apologetic about that. We want to build a really big company, and to do that, as Mac said, you can’t operate at room temperature.

Dexter Cousins
You touched on this earlier, Mac, with the AWS-for-banking idea. Look at the banks and one of their biggest competitors, Revolut — a business I’ve worked closely with over the last five years. They’re unapologetic about their commitment to excellence and what it’s like to work there. You’re either up for it or you’re not, and if you’re not, don’t go. If you are, it could be the best two years of your life — and it turns out the people I’ve placed there have stayed five years —

Macgregor Duncan
Startup years are dog years. One year is seven. That’s exactly right.

We interview a lot of people, and we’re really honest with them before they join: it’s hard, we have very high standards, we expect excellence. Our internal mantra is that we aim to be first class in everything we do, and that’s an exacting standard. People often say, I’m just not up for that — or not at this point in my life — and we’re super respectful of that. Sometimes we think that person is probably more psychologically balanced than we are. But if you’re committed to doing something outstanding, it comes with certain requirements, so we try to attract people like that.

Dexter Cousins
So, the billion-dollar question — I have to stop saying million, billion’s more relevant here. You’re drawing on a talent pool that’s maybe 10% of the workforce in attitude and mindset for this kind of environment. Then you want excellence, so you’re talking about the top 1%. Then there’s the right skill set, and the competition for that person. How do you actually hire people who’ll move the needle?

Di Challenor
It’s an art, not a science. We have a pretty rigorous interview process, and candidates meet a lot of people across the company. We’re really looking at the company hiring the individual, not the manager, because in our company the people you work with are the key to your success. If you come in and that group isn’t going to put their arms around you and get you through the first couple of months, it can be really hard.

So it’s not ten interviews, but at least three or four people involved, to test whether there’s a cultural fit and a technical fit. Both matter a lot to us. We do a lot of technical testing — a take-home assignment, then you come back in and review it with our key engineers. It’s a strong process.

Then when people join, a lot of us meet them every week: how are you going, how can we help, what roadblocks have you got? And we give them context — why this matters, why excellence matters — and keep reinforcing it. You can hire people, give them a desk and a laptop and let them go. But at Constantinople, we’ve had more success by investing in people when they arrive.

Macgregor Duncan
Just really quickly — 99.9% of our hiring is referral. It’s friends of our people, or people they’ve worked with before, and that’s a very good first filter. If someone who’s been successful at Constantinople says, I worked with this person at Revolut, or Airwallex, or Canva — which tend to be where we hire from — there’s a good chance they’ll work well here too.

Dexter Cousins
I wanted to ask about what you described, Di, because that process isn’t what you’d expect from people coming out of big banks. My observation, and the data backs it up, is that it’s very hard for executives from large banks to make the leap into a startup. They’re used to doing one thing with a lot of support around them. In a bank, how many people would run that process for you, while you go to meetings and check in once a quarter for a performance review? How did you first recognise the gaps — the skills you’d developed in that environment, versus the areas where you were suddenly well short — then prioritise them, and then fill them?

Di Challenor
After leaving banking and moving into software engineering and building platforms for banks, someone described us as — I’ll try to get this right — intrapreneurs. Entrepreneurs inside a bank. When I reflected on my own skills, in banking I was the one pushing the envelope — I’m sure some of your listeners would agree — doing things differently. I’ve never been a straight-line person. So the ability to get inside a large system and make change was one thing I thought would help in setting up the business with Mac.

We’d had a bit of a trial run, having worked together before, so we knew what we’re each good at. I won’t speak for Mac, but I’m more competitive about the outcome than about what I personally do. I just want a great outcome, so I don’t mind if someone else is better at something. If I’m not good at it, why spend time getting good at it when I’m good at 15 other things? There was a natural alignment between my background and Mac’s. If you ask people at Constantinople what it’s like having co-CEOs, they say it’s really simple — we know what Di does and we know what Mac does. It works well.

Dexter Cousins
And from your side, Mac — what do you feel you bring to the partnership?

Macgregor Duncan
That’s harder for me to talk about. I agree with Di that we have complementary skill sets and work extremely well together —

Dexter Cousins
You’re being too modest. The best people are super self-aware.

Macgregor Duncan
All I’d say is that one thing we’ve done well is having an insatiable appetite for learning and improvement. We really don’t hold fixed views on anything. We’re constantly self-critical, trying to work out what we got wrong. We’re constantly reading, listening, trying new things. You make small changes every day, and they can be imperceptible, but after two or three years you look back at the compounding returns and think, we are very different executives today.

Dexter Cousins
That’s one of the beauties of the podcast — bringing people back and looking at the journey. Some have failed: what did they do wrong? Some have succeeded: what did they do right? Which is a nice segue. We did the first podcast almost two years ago. Looking two years ahead, where do you expect Constantinople to be, and is there any news you can share?

Macgregor Duncan
We’re building a single, multi-tenanted platform that can run tens, if not hundreds, of banks around the world. We’ve made a really strong start, but this is a decades-long business. Internally we describe it as building a factory that can mass-produce banks. We have our initial proof points, and now we need to keep executing. We’d like to move into another market later this year or early next year. Two years out, I’d like to see ten-plus banks operating on the platform.

Dexter Cousins
Let’s go for 20.

Macgregor Duncan
Twenty banks. Five x is the new ten x.

Di Challenor
If you’d asked us three years ago where we’d be today, we’d be so pleased with where we are. If we keep operating at this level of capability and intensity, and keep delivering for our clients, we’ve got a really bright future. That’s what matters most. We must deliver for the clients we have today, because that’s what will make us a successful company — and that’s our right to play in the global marketplace.

Macgregor Duncan
One thing we often say inside the company is that our most valuable asset — our reputation for delivery — doesn’t sit on our balance sheet. That’s the asset we most need to protect and build.

I couldn’t agree more with Di. Building a company is getting all the pieces in place; there’s no silver bullet. The pieces build on each other to get you to an outcome, and you just keep at it. You have great days, and days where you think, wow, this is hard, and you keep going. It’s not a glamorous job. You’re talking to Nathan and Michael from Athena next, and you spoke to Ben from Zeller — most of these people will tell you they’re not sure they’d do it again. It’s much harder than people think. But on the flip side, none of them would have it any other way. The experience is incredibly valuable and enjoyable, but it’s hard work.

Dexter Cousins
We’re coming to a wrap. We get amazing talent listening to this show — if anyone’s interested in careers at Constantinople, where should they go?

Di Challenor
Go to LinkedIn and send us a direct message. We’d be happy to respond.

Dexter Cousins
Awesome. Di, Mac, thanks so much for joining me. We’re locking in the calendar for two years’ time for the third instalment of the Constantinople journey. It’s been fantastic to chat, and amazing to see your progress.

Di Challenor
Thank you, it’s been great to be here.

Macgregor Duncan
Thanks very much.

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