An interview with Toby Esser, group chief executive officer of Cooper Gay

Choose four adjectives to describe yourself.

Driven, demanding, competitive and calm.

What qualities do you most admire in other people?

Much the same as the adjectives I have just given, but also ambition and loyalty. Loyalty is a massive thing for Cooper Gay and means a lot to me in both my personal and business life. There are so many people here who have literally been with this company forever. Their loyalty is enormous, but this is also a quality that you will see in their personal lives as well.

I also think it is important that those who have achieved a great degree of success also retain a certain level of humility. Having said that, most successful people have a certain degree of arrogance, but there should be an element of humility as well.

What qualities do you most dislike in other people?

I don’t like lazy people, those who lack any ambition or desire. I dislike those who will not make the effort to better themselves in whatever way that might be, but would rather sit back and accept their lot in life.

You should always strive to achieve something, whatever that is. I also dislike tardiness and general slovenliness.

What do you know now that you wish you had known when you started in this industry?

I can’t really think of a lot of things. Rather it would have been interesting if somebody had told me 20 years ago that we still wouldn’t have contract certainty 20 years later and that we still wouldn’t have electronic processing.

I would have liked to have known that the market was going to change in the way that it has, because when I joined it was in the dark ages.

We still had information being kept by the Lloyd’s underwriters on little cards. It was also very much an “old school tie” industry - people came here not because they wanted to or were qualified to, but rather because they had a family connection in the market. I almost left the industry because of this level of unprofessionalism.

What was the last thing that completely surprised you?

Chelsea losing 1-0 to Real Betis in the European Champions League - that was a complete shock.

I can’t think of one in the insurance industry. For example, you couldn’t say that Katrina was a surprise. Maybe the size was a surprise, but the fact that an enormous loss like this has come along had to be expected. This is the nature of the industry we are in.

What motivates you on a Monday morning?

I’m very lucky because I love my job and so do not suffer the Sunday evening blues. I do this for fun, which is a real privilege. But I think that is true for the majority of people here, which I am incredibly proud of.

Whose job would you most like to have and why?

I would like to have Roger Federer’s job (at time of press ranked world Number 1 by the Association of Tennis Professionals). But I have to be allowed to have his talent as well!

What is your biggest regret?

I have no regrets and I don’t believe in looking backwards. I would say that I am very lucky in what I do and how I have done it.

What are you most proud of having achieved?

I mentioned before my pride in the people that work here. I am proud of the success that we have achieved and the size that the company has reached while still maintaining its private independent nature. There are not too many companies out there that you could say have got to this stage while maintaining that independence.

What factors have enabled you to get where you are today?

Luck is always a factor, but I would say the main one is my desire to achieve. I was extremely competitive from a very young age and always had a clear vision of what I wanted to do. At the age of 19, I told the directors here that I wanted to run this company, and while I remember one director laughing, the majority of them seemed to like my ambition and aggression. I certainly like it when young guys tell me that they want my job - I want that kind of person in this company.