Richard Robinson of Robin AI On Discipline, Modern Leadership, And Debunking Conventional Startup Wisdom

In the space of a 2-hour Zoom call, I had the privilege of stepping into the mind of Richard Robinson. Quite frankly, I didn’t want to leave.

Richard has an uncanny ability to take a contrarian idea, and in very few words, convince you of its truth in a blasé and matter-of-fact way. His rigorous training in law and 5 years of debating no doubt have something to do with it.

Before entering the world of entrepreneurship, Richard spent 5 years at Clifford Chance and Boies Schiller Flexner, two of the most prestigious law firms in the US and UK. On top of this, he was a member of the British debate team and coached the England one.

Richard founded Robin AI back in 2019, driven by a compulsion to seek out the hardest problems he can find, and a desire to prepare himself for a life of leadership. Armed with a team of paralegals, PhD-level AI engineers, and a cash injection from Forward, Richard has hit the ground running with his plan to use AI to automate low-complexity legal work.

In a long-form interview, Richard shares all about his path to building a venture-backed business. Witnessing the risky nature of entrepreneurship as a child, starting a sneaker hedge fund that delivered 20% returns, reading the entire works of Shakespeare on weekends, and going from a mediocre student to a first-class law graduate, are just some of the delightfully complex components of Richard’s journey.

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Talk to me about your journey to becoming a founder. Were there any early influences in your life that led you down this path?

My dad was an accidental entrepreneur - a fishmonger. He lost his job and was compelled to become his own boss. Though he knew absolutely nothing about fish, after responding to an advert in a newspaper, he became a fishmonger.

I've seen studies that show that if your parents were entrepreneurs then you're more likely to become one. I always thought the opposite was going to be true for me, because entrepreneurship is so uncertain. My parents wanted me to have a stable profession. To become a lawyer or a doctor - like most immigrant parents - and to avoid the ups and downs that come with entrepreneurship. And, largely I agreed with them.

But always had a little bit of ‘entrepreneur’ in me. My parents always taught me to work really hard. To find ways to be creative. For instance, my dad used to buy the latest trainers from New York and sell them at a premium at home, in Birmingham.

So there was always this edge. And I took that with me to University to study law.

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Why did you choose to study law? And where did it lead you?

Well, I thought it was a really hard degree. And my dad always used to say “Law is a hard degree. If you can do well in that, and get a first, then your future is set.” So that’s exactly what I dedicated myself to doing, and it worked out. I eventually joined one of the best law firms in the country - Clifford Chance.

It was intense. Remember, this is an industry where people count hours, and I always made sure to hit my hours. It brought out the competitive part of me.

During this period, I still found the time to work on a few side projects. First was a nightclub app that I started with a friend. But it didn’t really work out. My next idea was buying and selling rare trainers for a premium. Eventually, I had the thought - what if I did this for other people? So I created a hedge fund of sorts with 10k investment from friends and would buy and sell trainers for profit. I didn’t realise it was illegal at the time… and they got a 20% return in the first year!

This was about the time that I left Clifford Chance and went to a much smaller law firm.

Did you grow tired of a large corporate?

Don’t get me wrong, Clifford Chance is amazing. There are 3000 lawyers, 36 offices across 23 countries. They have some of the most outstanding lawyers in the world. But I wanted to have a hands-on impact - and being a small part of a large corporate didn’t allow for that.

I was hungry to specialise, and get stuck in. Most importantly, I wanted to learn, and I had the niggling feeling that people at smaller law firms were learning more than me. And I couldn’t tolerate that once it was in my mind. Like inception. I just couldn’t get that idea out of my head.

It’s as if I was at Man United but I was sitting on the bench, week-in, week-out. Others were playing for less well-known teams. But they were in the same league.

I wanted to get off the bench. So I moved to Boies Schiller Flexner. They were small, new to the UK, but well-established in the US. For better or for worse, they represented Theranos - the controversial blood-testing startup - and also led a few other high-profile cases.

It felt like joining a startup because there were only 13 people in the UK company. Before I joined, my boss Natasha said “Richard, I can’t afford for you to do the kind of work you’ve been doing, as I don’t have 100 people here. You’re going to have to do stuff that’s harder than you’re ready to do.” After that, I was sold.

Just after I was sent on secondment to one of our firm’s clients, we found out that we were pregnant. At this moment, I realised it was now or never for entrepreneurship. I couldn’t wait any longer.

My wife 100% supported me, but gave me an experimentation budget, and said I had to focus on 1 idea, and 1 idea only.

Before we get onto Robin, I’m seeing a pattern with you picking hard problems. You studied Law because your Dad told you it’s the hardest degree you can do. Equally, you joined Boies Schiller Flexner because Natasha told you it was going to be a struggle. Why do you keep doing that?

Hard problems are the ones you learn from. I went to a comprehensive school in Birmingham, that was in special measures. It didn't have a lot of resources. I managed to get into a great sixth form, but as soon as I walked through that door, I realised that I’d missed five years of education. There are things they know that I simply don't know. There are things that I was never taught.

When I realized that, it invoked a real hunger, partly competitive, that I would never waste any beautiful opportunities to learn again.

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Also, you debate. Did this shape your worldview as well?

The truth is, being introduced to the debate team fundamentally transformed my academic performance.

For whatever reason, before that, I was a mediocre student. But once I learnt the principles of how to construct an argument, my grades went from mediocre to very very good. I went onto debate at sixth form and university, joined the British debate team, and travelled across the US. I’ve also coached the England debate team for the past 3 years. It’s been a real honour.

And it’s not just a game. It changed the way I saw the world. It also taught me a tremendous amount of discipline. Once, I was in a debate competition about Shakespeare, and to prep, you had to read all of the works of Shakespeare. No shortcuts. It took countless weekends. But you just had to get it done.

Now, back to startup life. Your wife gave you a budget and her blessing. What happened next?

I built a simple chatbot - called geek mate - that helped tenants get their deposits back, by constructing a legal letter that they could send to their landlord. I spent all my budget on the build, so launched on Facebook with no advertising. By the 3rd month, 300 people had used it, and I was getting an influx of positive testimonials and people sending me beer!

Through launching this I proved that:

  1. People would trust technology to do things they might have otherwise asked a lawyer to do, and
  2. A lawyer can be taken out of the equation if we can capture all of the required legal knowledge upfront.

And that’s what I approached Forward with - a chatbot and a pitch about using technology to automate low-complexity legal tasks.

I considered other venture builders, but they wanted to take 50% of the business. Traditional VC’s wanted me to have a technical co-founder - which I didn’t have, and it wasn’t a decision I wanted to rush. There was also very little clarity on the product at that point - so to expect someone else to join at that stage, would be an unreasonable ask.

OK, you’ve got the cash. What’s next?

Step one is research. The studio team drilled the importance of customer research into me, and thank goodness they did, as we landed on a fundamental insight that shaped our initial product. We interviewed a lot of lawyers, and managed to elicit the insight that lawyers hate reviewing contracts. A lot of them are highly repetitive, but despite this, they have to read through them, line by line, in case there’s something new. Or unexpected. They then have to edit, send it back, and manage the back and forth. It’s a real pain.

In building it with my CTO James, we discovered that AI isn’t going to completely replace the need for humans. But it is going to make that person 10x faster, and reduce the required seniority. Someone with 2 years of paralegal experience, would be able to get the job done.

With this insight, we landed on the idea of AI+. Combining powerful AI with humans to produce a high quality work product.

We’re now a team of 6. We have 1 paralegal, 2 PhD-level AI specialists - which is a source of great pride - my technical co-founder, and I.

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What’s the hardest part of being a founder? Is it very different from your past life?

You have to do 100 jobs. Sales, marketing, website design, cleaning, leading the team. There’s so much you have to do, and be good at. And you have to be comfortable with not always producing your best work.

Also, being a leader at a time like this is very hard. Not least because I feel a tremendous amount of responsibility for everyone who is on my team. I’m telling them “I can’t guarantee success, but if you trust me, I won’t let you down.” That’s a tremendous amount of responsibility. During COVID that was only heightened.

Would you say you’re a good leader?

I’m definitely learning. I’ve exposed myself to extreme experiences that will improve my skills as a leader. I think and believe that I'm doing well at that job. Especially when I compare myself to leaders of the previous generation.

I’ve given it a lot of thought. I’m considerate of work-life balance, communication, diversity and inclusion. These are things that are at the top of my agenda for how I want to lead. I came into this process with wanting to test these. Almost like an experiment.

Can you build a diverse, successful startup that respects people's desire to be pushed professionally with tremendous autonomy, without requiring them to work weekends or late nights? Can you do that? I'd always believed that you could.

And so this is one big experiment for me. And so far, it's working.

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An article in The Telegraph, penned by Richard

Why are you doing this Richard? Does it come back to leadership?

This opportunity is, without doubt, the best opportunity for me to learn and prepare myself to continue to lead. I’m not just trying to run a business. I’m not trying to make money. To be honest, I had more than I needed as a lawyer. This isn’t about status, or being in the press either. I don’t even tweet!

I'm trying to test a theory about leadership that I truly believe.

I’m challenging conventional business wisdom. People say “Forget diversity, pick the best person for the team”. They say “To beat your opponents, you have to work harder than them (which means longer hours)”.

And, I just don’t believe you have to adhere to these things to build a successful, diverse company. Or to be a strong leader. This is an opportunity to put it to the test.

And, what do you love the most about company building and what frustrates you the most?

There’s something so exhilarating about sales. Selling a product or vision. It’ll never be lost on me. Second to that, I love the process of constructing teams. As mentioned before, I reject the idea of “hiring the best person for the job”. You should hire the best person for the team. You’re adding someone into an existing dynamic - so using competence as an objective metric, is just wrong. You need to look at the gap in perspectives in your team, and fill that position accordingly.

Also, the fundraising environment is frustrating. I don’t intend to attack VC’s, but I’m not convinced venture is set up to back truly bold businesses. Venture is meant to be about investing in risk, but in my experience, most of the funding goes to companies that fit a certain narrow pattern.

And that’s fine. It’s not at all...bad. But the world would be a better place if there was a funding option for people with truly risky and innovative ideas. That doesn’t exist here in Europe.

We’re trying to do something quite difficult and quite ambitious and quite different. It doesn’t match the patterns of the last 20 years. In lots of conversations I’m having, investors are trying to fit us into an understood box. And there isn’t one that exists.

What is one misconception people have about company building that irritates you?

The idea that people have to work all day and all night. A culture of relentless ‘hard’ work, as opposed to smart work.

It’s incredibly unfair. Especially when you impose that on your employee’s. As a founder - it’s different. You have significant equity and a reputation at risk. But your employee’s often don’t.

A test of good leadership is when people volunteer to work hard, only when it’s appropriate.

If you have to force people to work hard when it’s required, then you’re not doing very well. Equally, if people are constantly volunteering to work hard when it’s not required, then you’re also not doing very well.

Can you get people to know when it's needed? And to do it themselves?

The second one is to hire fast fire fast. I just really hate it. One of the worst characteristics of tech businesses is this idea that we're purely growth machines. That we’re going to move fast and break things. Those things being regulations, people, governments, livelihoods, inclusivity whatever it might be.

It’s immature.

A sign of a good leader is one who leaves things better than when they came. And thinking about my team - I cannot guarantee that they’ll have a job. I cannot guarantee that they will always be in our plans. But I can absolutely guarantee that I will not fire them quickly or do it hastily.

I won't have a disregard for their family, their personal situation and the trust that they put in me. I will always be slow and hesitant to let you go. It’s the least they deserve.

Lastly, what is the one skill or the one thing that you think is going to be most necessary for Robin to be successful?

Communication, communication, communication. We have to change people's behaviour. We have to be able to make an argument that helps people change their minds. On all fronts. We have to be able to tell potential customers that there is a different way of doing things that will help you enjoy your work life a lot more. We have to be able to convince our potential employees, who need to be some of the best people in the world, that what we're doing is truly game-changing.

And we have to convince investors that our proposition, despite not matching patterns of the past, is still worthy of their time and money.

Shope is a marketer, writer and headshot photographer. As Brand and Content Manager at Forward Partners, Shope executes on our content strategy and works to build our awareness with early-stage founders. Prior to joining Forward Partners she worked at e-commerce and marketplace startups, initially as a content creator at ASOS, before moving onto support Drover and Common Objective with their communications and content. She has a strong interest in consumer brands and sustainability.

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