Matt is founder and CEO of Nested.com, an estate agent to buy and sell at the same time. Previously, he founded GoCardless, a global bank debit network processing over Β£13bn in payments annually for more than 50,000 organizations. His very first company, whilst still at school, was Sharp Service Waiters, training and supplying waiters and bar staff to private events.


On balancing personal strengths and weaknesses.
The day you stop learning is the day you die. In Greek literature, there’s this concept called Hamartia. It’s the tragic flaw of a protagonist or hero that typically leads to their downfall. I think a lot about it. Someone’s biggest strength is often their biggest weakness. I have a strong, forthright character with good conviction. When I was starting out as a founder, I was weighing in on way too many topics. I was too hands-on. I pity the designers that had to work with me then.

On a framework to decide involvement as CEO
Over the years, I evolved my thinking to be more open-minded and collaborative. There are clear improvements in letting great people have a go. But there’s a danger in not sharing your thoughts with enough clarity. I use this two by two matrix. How important is a decision? Low or high? How certain am I of being right? Low or high? If the answer is not two β€œhigh”, I try to stand down. The upside: happier people that create fun things. The downside: more decision-makers means less consistency. Achieving the right one for each stage is one of the most important balances any business can strike.

On lessons learned from his family
My family taught me to always try and do the right thing. To treat others the way we want to be treated. About integrity and looking after one another. Often, we act like companies are different than us. But companies are collections of people. Hence they should treat people as if they themselves were people.

On applying this principle to his companies
Years ago, one of our GoCardless analysts had made a discovery: for eighteen months, we had been overcharging one of our customers. We’d fix their fees going forward, and it was so complex that they’d never find out on their own. The analyst had a dilemma: be silent and keep the money, or explain and risk upsetting our relationship. For me, there was only one choice: it was their money and we would return it. We apologized to the client. They could not believe we were returning something they had no way to discover was missing in the first place. They said: we’ll never leave you, now we know we can truly trust you. Doing the right things leads to better outcomes over time.

On the role of CEO
Whilst at school, I built a company training local youths and supplying them as waiters and bar staff to corporate and private events. Occasionally, there was somebody that would not turn up, last minute. So I would turn up myself to do fill in. It’s a really good lesson for anyone wanting to be CEO. You want to do the fun, great stuff. Ultimately, you have to look at what your business does and appreciate that it’s where the value is. Sometimes you just got to roll your sleeves up and get it done. During the lockdowns, everything was a bit all over the place. On Saturdays, the Nested team was so busy that I would also do customer support.

On the hardest company stage
It never gets easier. Existential threats are at every stage, no matter how big you get. You have a series of product-market fits. Something might get broken at any point, and it might undermine all the work you had done to get to that stage. The frustrating part is the bit between identifying the problem and seeing the result. In a B2B sales cycle, it means it can take 12-18 months before you see the fruits of your labor.

On company culture
Values are a bit like an org chart, right? Either you design it, or it designs itself. Β Investing in our values from the start was something I invested a lot of time in, at Nested. They are part of the interview process, they are on the walls at the office. People live and breathe them and they change over time. We look at them every six months and tweak them slightly, or adapt them to the stage the company is in.

On his productivity hack
I very strongly believe in having an operating system. As a CEO or Founder, it’s critical that you do what you said you were going to do. Every time, in a meeting or elsewhere, I say I am going to do something, I immediately email it to myself. My day often ends with me going back to my inbox and powering through. This way it’s impossible I forget my ToDo.

On protecting family and health
There are two things that I have tried to change over time. One: spend more time with my family: I timebox it, to make sure I do not miss out on it. Two: try to sleep better. I used to sleep so little. I’d work all the way to 3 AM and start again at 7 AM. Then I read, anecdotally, how Margaret Thatcher and Ronald Reagan would talk about how they could survive on four hours of sleep per night. They both went on to get Alzheimer's. It scared me: my brain is the one thing I’ve got and I don't want to lose it.

On books every founder should read
The Little Kingdom: The Private Story of Apple by Mike Moritz. Most media about the company focus on how much of a genius Jobs was, or present this deterministic view on how they were always set to be successful. Then you have this book where the author interacts with the employees on the frontlines and they tell you how screwed and broken everything was. How nobody trusted Jobs. How much he didn’t know what he was doing. How close they were to running out out of cash. How everything could have gone wrong at any moment. Every company always feels this way, no matter how successful they get. They just never put it in the press releases. So you end up thinking it’s just you, and everyone else is fine. Let’s just take a breath and think: okay, it’s not just us.

On his motivation for angel investing
I love building businesses. I have been fortunate to build a couple. My goal is to keep doing this as long as I can, building one per decade. If I built six, seven, maybe eight businesses, that's fantastic. However, there would still be a ton of amazing people I didn't get to work with. A load of really interesting problems I never got to think about it, things I never got to learn. That's where angel investing comes in. I approach it mathematically and portfolio construction is key, however, I get a lot from it other than seeking financial success.

On his investing approach
A company is only as good as its cash flow so I always look for strong cash flow profile. Β Then I approach it with the mindset of the hiring process. There are a hundred reasons why someone is not the right fit for a job, but reasons that ultimately don’t matter. You must search for the one strong reason that makes them the right person. You are not looking for the perfect background, for someone that went to a certain university or worked at a specific place. You are looking for the one thing Β that will make them successful. For me that’s either a founder, a product or traction that gets me truly excited and believing that they just might make it.

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