Why did you become a lawyer?

It just sort of happened. I did a law degree, which I enjoyed, but I had no idea what solicitors actually did. I thought I might as well do my articles as, even if I didn't like it, it would be a useful qualification to have – and here I am, still loving it.

Who has been the biggest influence on your career?

Going back to my Frere Cholmeley days, I would say Steven Sugar, who taught me the benefits of intellectual rigour and precise drafting.

What's your proudest professional moment?

Probably concluding the original Attheraces deal (where the Attheraces joint venture acquired the media rights to British horse racing). It was an incredibly complex and challenging transaction.

…and worst day on the job?

During my articles, I was asked to prepare a lease for one of the firm's many aristocratic clients. I was called up by the client partner who said: "David, thank you so much for the draft. I am afraid you have made one monumental error, which I hope you never repeat in the rest of your career at Frere Cholmeley. It is the Honourable Hugo…" I think he was actually teasing, but I was worried.

Aside from your own firm, which lawyer do you most admire and why?

I'm a big fan of James Conyers, the general counsel at BSkyB. He manages to combine a thorough grasp of the detail while only concentrating on the points in a deal that really matter. He is also a pleasure to deal with and a big horse racing fan.

What's your strongest characteristic?

I do not get stressed (other than by my children) and I'm good at delegation (see below).

…and worst trait?

Nagging the solicitors to whom I have delegated.

How do you think assistants in your team view you?

I forwarded this to one of the solicitors who works a lot with me and she replied: "Annoying, like my dad, bit of a mover and shaker (but only on the dancefloor at the Christmas party), particularly good at delegating everything (even this question), so free to watch racing all day and then go home." I think she missed out the bit about inspirational role model.

What advice would you give to young commercial lawyers starting out?

First, there is no substitute for knowing the law. Then, the best way to learn is through experience of working on deals. After a while, you will realise that negotiation is not about having to win every point and that you have to understand your client's business and commercial objectives.

What's the best part of your job?

The people I work with at Olswang and my clients.

What most annoys you about the legal profession?

Lawyers who point-score and forget about what their client is trying to achieve.

What will be the most significant market trend in terms of your practice area over the next 12 months?

The continued progression to real convergence and more consolidation in the media market generally. As regards broadcasting, BSkyB has been taking very aggressive positions in the past few months and it will be interesting to see how that pans out both with the regulators and its competitors.

What is the most common misconception trainees have about Olswang before they arrive?

That we are all terribly cool and they will spend all their time going to luvvie events.

How cool is Olswang?

See answer to previous question.

Hobbies?

Horse racing.

What would you do if you weren't a lawyer?

Be a bookmaker.

Where do you see yourself in 10 years' time?

Assuming this is published in a couple of weeks, leading in the winner of the Cheltenham Gold Cup (as the owner, not the stable lad).

What is your favourite joke?

What's the difference between an Australian and a yoghurt? Culture. (I don't have anything against Australians; some of my best partners are Australian.)

What's your favourite cheese?

Cashel Blue.

Dealmaker returns in two weeks.