Square Mile and Me: Robin AI CEO Richard Robinson on making it in the startup world

Each week we ask a City figure to take a trip down memory lane. Today, Richard Robinson, CEO and founder of legal AI startup Robin AI, tells us how he got there

What was your first job? (Saturday job, bar work, that sort of thing)

Working as a fishmonger with my father during the school summer holidays. 

What was your first role in business/law?

I was a trainee lawyer for the Magic Circle law firm, Clifford Chance. 

When did you know you wanted to build a career in the legal sector?

My uncle was in a famous band from the 80s called Musical Youth who had the hit single, ‘Pass the Dutchie’. Despite their global success, they were let down by bad legal advice and ended up missing out on royalties. This showed me how important access to good legal advice is and motivated me to pursue a career in law. 

What’s one thing you love about the industry?

I loved the teamwork in my legal career. As a litigation lawyer, we used to work on multi million-pound deals, and every case we worked on was a team effort. There was a sense of complete camaraderie, which made us more productive and made the work more enjoyable. 

And one thing you would change? 

Legal services are too expensive. The majority of the British public cannot afford to access essential legal services. This is Robin AI’s goal – to bring down the costs of legal services and make them much more accessible for everyone. 

What’s been the biggest adjustment to transitioning to the startup world?

Taking risks. As a lawyer, my job was to minimise risk and work alongside guidelines and from a rulebook. In the startup world, everything is completely new. I’ve had to learn how to embrace uncertainty and make the most out of the unknown. 

What’s your most memorable lunch?

I was lucky enough to have lunch with Matthew Layton, the former global managing partner of Clifford Chance. As a trainee lawyer at the time, it was an incredible opportunity to have access to one of the most powerful and influential people in the industry. 

And any City faux pas? 

There’s nothing worse than turning up to your first day of work wearing a black suit with brown shoes… a mistake I did unfortunately make. 

What’s been your proudest moment?

I am incredibly proud of my team. During Covid, Robin AI was advised to let go of our entire team due to costs. However, we stood strong and didn’t let go of anyone. This group of people led us to our seed round and all bar one still work at the company. Also, at our offsite in January, we identified that 50 per cent of our staff are women and 33 per cent are from ethnic minorities. We are one of the most diverse tech companies in Europe. 

On a separate note, back in 2018, I coached the England debate team, which ended up coming third at the World Debating Championships. This was the most diverse English debate team ever – with the team being majority female. Coaching and leading the team prepared me for my role as CEO today. 

And who do you look up to?

Professionally, Matthew Layton, the former managing partner at Clifford Chance and former US President, Barack Obama. 

Outside of entrepreneurialism, it has to be Christopher Nolan. He is a huge source of motivation for me with a distinctive style and outstanding execution. 

Are you optimistic for the year ahead?

Of course! This year is set to be the best in our company’s history – a belief that as a co-founder and CEO I maintain with each new year. Over the past 18 months, AI has captured everyone’s imagination. The next 12 months will see this exciting technology delivering tangible benefits for businesses, proving that this is not just hype.

We’re going for lunch, and you’re picking – where are we going?

Brigadiers in London

And if we’re grabbing a drink after work?

The pub next to our London office: The Magpie 

Where’s home during the week?

I’ve just moved to New York City as our company is rapidly expanding into the US. But for the last 10 years, I was based in Canning Town in East London. 

And where might we find you at the weekend?

Now, I’ll be in and around New York City!

You’ve got a well-deserved two weeks off. Where are you going?

There’s only one answer: Cancún in Mexico. Beach, tequila and tacos – what more could anyone ask for?

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