My Business Life: Paul McCarthy-Brain, Flip-Pay

Flip-Pay CEO Paul McCarthy-Brain shares lessons on entrepreneurship, AI, scaling globally, digital subscriptions and building technology businesses.

Few entrepreneurs can say they have helped build both a betting exchange and a media revenue platform, but that unusual journey is central to the story of Paul McCarthy-Brain, CEO of Dublin-based Flip-Pay.

Over the course of his career, he has moved from the fast-paced world of real-time trading infrastructure to helping publishers tackle one of the biggest challenges facing modern journalism: generating sustainable reader revenue.

Before leading Flip-Pay, McCarthy-Brain spent more than a decade developing technology for the betting industry, including serving as CTO of Racecourse Data Technologies and working on BETDAQ, the betting exchange that was later acquired by Ladbrokes. The experience gave him a deep understanding of customer behaviour, transactions and digital business models.

For the past 11 years, he has led Flip-Pay, building subscription and reader revenue systems used by publishers including The Huffington Post and The Salt Lake Tribune. The company was founded to solve a problem many publishers struggled to address themselves: how to convert loyal readers into paying supporters without relying solely on traditional paywalls.

Tell us about your background, what journey did you take to arrive at where you are?

My great uncle Wilfred, ex-RAF, taught me basic electronics when I was little and it was like all the lightbulbs went off in my head. The first thing we built was a crystal radio set and then I built my first computer at the age of 11 – it was an Acorn Atom. This led me to studying Electronic Engineering in University and on to a career in electronics and computing.

I worked in the UK, Belgium and Israel, then moved to Ireland where I started working for Dermot Desmond in 2001, as part of the team that launched the betting exchange company Betdaq. Then we launched Race Data Technologies, Flip-Pay and KitchTech. I serve as CEO of Flip-Pay, the subscription management company and Technical Director of KitchTech, which is a digital food safety compliance company.

Why are you doing what you are doing? What need are you meeting? What’s your USP?

First of all, I’m a serial starter-upper and likely unemployable in a multinational. I enjoy the struggle of getting projects off the ground and to market. It’s what I know how to do and I don’t work well with constraints.

Flip-Pay was born out of an R&D project looking at the viability of micropayments in the digital media industry and the impending digital currency evolution. It has evolved into a disrupter of content monetisation technology and is grabbing significant market share in Europe and the USA.

Publishers typically require five or more different products to do what Flip-Pay does on one platform – we simplify deployment and use, while offering the most powerful and extensible solutions to the market.

How did you fund and start the business and what are your growth plans?

Flip-Pay is owned and privately funded by Dermot Desmond. We’ve been experiencing explosive growth for the last two years, especially in the USA where there is great interest in our technology. We have staff in Ireland, the Netherlands, Slovakia, the USA, Columbia and India, but we’re currently focused on growing the headcount in our new IFSC offices in Dublin to cope with the demand for the business.

One of our most important clients is Mediahuis Ireland – we built the paywalls for the Irish Independent and the Belfast Telegraph 5 years ago when they were just starting to work out how to monetise their readers online, and we’ve seen them grow to more than 100k paying subscribers in that time. We’ve also just started working with Irish Farmers Journal, modernising the subscriptions technology across their group of newspapers and magazines.

Next up we’re launching new AI verticals in September, something completely outside of subscriptions and monetisation, which will be a whole new sales channel for us. We are also expanding well in LATAM and will be focused back on EU growth in 2027.

What are the key skills and qualities that set you apart?

I can digest a huge amount of information quickly, look at everything as a possibility and when I’m not running Flip-Pay or keeping an eye on the day to day of KitchTech, I’m building new technology in my spare time. I’m fascinated by the space and that makes it really enjoyable.

What (or whom) has helped you most along the way? Who was your greatest mentor/inspiration?

There are three people that made an impact on the man I am today.

Beni Fish, from Scitex UK, showed me how to lead. He was a great communicator, led from the front and by example, and explained why we were moving in a specific direction, so everyone knew their part.

Donal Plunkett, from Betdaq/ GBet taught me how to prioritise, filter out the noise and deliver quickly. He is an expert in project delivery and management.

Dermot Desmond – I’ve worked from Mr Desmond since 2001 through various companies and projects. I learned focus, urgency, clarity and how to compartmentalise. He’s been brilliant to work for and I am extremely loyal to him. 

What was the greatest piece of business advice you ever received?

This was from Brian O’Sullivan, one of our directors. I asked how he dealt with the onslaught of daily email and attempting to engage with all demands on your time. His answer was to focus on the important stuff and if someone really needs you urgently, they will find a way of getting in touch. This is a very liberating methodology. I have all notifications on my phone turned off (SMS, WhatsApp, calls, email, app notifications) and I look at it on my terms.

What circumstances/qualities/events can mark the difference between success or failure in life or business?

One of my mantras is “Work harder, not smarter”. It’s a deliberate inversion of the old saying “Work smarter, not harder”. What I mean by it is that there’s sometimes a tendency to believe that being clever, finding the right tool or coming up with the perfect strategy can substitute for simply putting the work in. It can’t.

Listen to the feedback early on. When I was building out KitchTech, I spent nearly every evening and weekend for about six months getting the product ready for beta testing. No funding, no staff. After some iteration with Dery Desmond and Jules Mak, we showed it to some chefs and business owners in the hospital industry, when the first question coming back to us was “How much”, we knew we had a business right there. Get feedback, get it often, then when you launch, keep taking your customers feedback as they will give you the features that will make it easier to get bigger, more enterprise clients.

What was the most challenging aspect of either starting or growing the business?

Not sleeping, the 4am demons telling you every reason why you’re failing and everything is going to go wrong. Then when you get past that stage, how you grow the business without losing your existing clients and coping with the new workload and expanding staff to cope with the new clients – this also keeps you awake at 4am. Nothing good comes from listening to your mind at 4am, but a cup of tea and making a list at 7am and you have a plan for the day.

How did you navigate your business through the pandemic and what lessons did you learn?

As a business, we already had staff in different locations so were adept at video calls and remote management. The hardest part was dealing with customers and doing all integrations remotely, with their staff all remote, which is now standard, but at the time, we and our customers were finding our way in the new reality. Sales calls were also a challenge, and we had to learn a whole new way to convey our message clearly.

It also didn’t help that a lot of new potential business was put on hold as publishers were hesitant to embark on large projects with their teams so spread out. However, we worked hard and we used the time to have a constant stream of new titles to deploy and further develop the platform. I should also mention that we had fantastic support from our investor throughout.

How has digital transformation been a factor in your scaling journey and do you believe Irish firms are utilising digital technologies sufficiently?

Well, we are a digital-first company, filled with some of the smartest engineers, so, we’re the ones helping other companies perform digital transformation. However, in 2022/23 we decided that, as we grew, it was time to get officially certified and we went through ISO 27001 / SOC-II / NIST CSF and got formal accreditation for GDPR, PCI etc – this radically changed the way we operated the business and continued to improve. The certifications then helped us get bigger clients and faster, but the real win was the policies and procedures that were put in place to move the company from startup to ‘real/grown up’ company.

The next element in terms of scaling the business has been the adoption of AI. We are a very high-tech company to start with and had been working with machine learning models for some time. But with the advent of LLMs and specifically enterprise-class AI tools, where we can protect our IP and customer data, we have now transformed our business once again and empowered all elements of the business, but especially engineering to 10x the output. We can now iterate in a fraction of the time it would have taken before.

If you were to do it all over again, what would you do differently?

There’s lots. I’ve wasted time and money listening to and accepting bad advice. Some things I’ve persisted with far too long and should have cut off earlier. If I could go back and start again, I’d have hired the dedicated sales team almost immediately, rather than trying to do it all myself. That just didn’t work. You’ve not got a business without sales and building up the pipeline takes time, more time than you think it does.

Who inspires you in business today?  

That’s an easy one, Dermot Desmond for the reasons above and the fact he’s still 20 steps further ahead in his thinking than anyone else I’ve ever met.

What advice/guidance do you give new hires and how do you nurture talent in your organisation?

You’ll make mistakes, own them, learn from them, share with others. You have the tools at your disposal to overcome any challenge, use those tools and your peers to achieve your objectives.

What business books do you read or would recommend?

The books I read would be mostly focused on the stuff I do badly, like sales and marketing. I enjoy the likes of April Dunford, who details how to create your brand messaging and use that to sell. Also, since he appeared everywhere, Rory Sutherland, with books on objective rationalism, like Alchemy.

The best book I ever read was written in 1916 by Robert R. Updegraff and called Obvious Adams – the story of a successful businessman. It’s really more of a short story than a book but I’d encourage anyone starting out to read it.

What technologies/tools do you use personally to keep you on track?

Morning – paper list of priority objectives for the day and anything urgent.

Apple Notes – I document everything here, notes, ideas, everything, and it’s available on my phone, iPad, desktop, laptop, browser – honestly, it’s the best tool Apple makes and the most underrated.

AI – I now have an enterprise AI agent trained on me and my daily life, so it understands the context of what I’m doing in relation to the past, and my future objectives and projects.

Beyond that my days are run by Slack and Google Workspace. 

What social media platforms do you prefer and why?

Threads – it’s sort of like Twitter/X used to be but now without the hate and nonsense. LinkedIn sparingly for business stuff and when our PR head tells me to post something.

But I’m not a big social media person. I know I should do more thought pieces and have a higher visibility than I do as company CEO, but my days are filled with actual work, and the sooner I can hire someone to look after the public side of the business the better.

What are your thoughts on where technology overall is heading and how it will apply to business generally and your business particularly?                        

Some see AI as the great destroyer, the harbinger of doom etc, I see it as a productivity tool and a means to achieve more, faster, more accurately with objective decision making and engineering.

I feel lucky to have witnessed the start of the home computer revolution, the introduction of business computing, the birth of the early internet, e-commerce and arrive at a point where a handheld device has an insane amount of processing power and access to the entirety of human knowledge, with the ability to create new technologies powered by voice.
I cannot tell you where we’ll be in a decade from now, or even five years, but this is the greatest time to be an engineer, to be involved in business and have these capabilities at our disposal.

Finally, if you had advice for your 21-year-old self – knowing what you know now – what would it be?

In 2010, buy a couple of the best GPUs you can afford and start mining Bitcoin, do not sell until September 2025, oh, and when you set up your subscription management company, hire salespeople early on.