How did you first get involved in horse racing?

My older brother, Oliver, got into racing before I did. He initially went to work for Arthur Moore in Ireland before moving to Fred Winter in Lambourn, one of the most famous trainers of all time. He then became an amateur jockey.

At that point, I was always known as “Oliver’s brother”, which, as you can imagine, used to irk me from time to time. I was much smaller than Oliver and wanted to become a Flat jockey. I was offered an apprenticeship with either Ben Hanbury or Robert Armstrong.

Unfortunately for me, I suddenly grew at the age of 16, so becoming a Flat jockey was no longer a realistic option. I decided to attend the Royal Agricultural College, where I completed a three-year diploma.

After finishing college, I thought, “Right, let’s give being a jockey another go.” I started out in point-to-point racing and was very fortunate to become associated with Libby Lees, who was based around Newmarket. She was really the catalyst that helped get me going.

There was a Hunter Chase meeting at Cheltenham in May where my first two rides under Rules were for Libby. Fortunately, both horses won, which generated a fair amount of publicity for me.

At that stage, I really caught the bug. I was riding good horses and enjoying some success, although in the background the plan was always to return home and start farming. Thankfully, my father took the view of “get it out of your system and give it a go.”

I was lucky enough to become Champion Amateur Jockey while working for Gavin Pritchard Gordon in Newmarket. Around the same time, Oliver started training in Lambourn, so I moved there and became the stable’s amateur jockey. I was fortunate enough to become champion again, and that’s when everything really escalated.

Who was your first winner?

My first winner in a point-to-point was a lovely horse called Icy Affair. It was at a local meeting held on our family farm in Essex. The horse was owned, trained and bred by my father, so he was understandably very proud. In fact, both the horse and the jockey had been bred on the farm!

My first winner under Rules was a horse called Lakin, trained by Libby Lees, at Fakenham.

What was your most memorable victory?

From a publicity point of view, it has to be the 1989 Cheltenham Gold Cup. It’s the ultimate race.

It wasn’t necessarily the most enjoyable race I ever rode in, but it was certainly the most significant. The Racing Post later voted it one of the most popular races of the previous 50 years.

For that reason, the 1989 Gold Cup has to be at the top of the list.

What was the most challenging course you ever rode?

I would probably say the original Aintree course, particularly the old Grand National course.

It’s changed significantly over the years, understandably due to welfare improvements. I first rode there around 1984 and the fences were enormous.

The challenge wasn’t just the fences themselves; it was also the fact that there were 40 runners charging towards them. The Grand National was a huge test for both horse and jockey.

I was fortunate enough to finish third in the Grand National one year on a horse called The Thinker, and simply getting around that course felt like a major achievement.

I was also lucky enough to win the Topham Chase around Aintree on a horse called Villierstown for Arthur Stephenson. We lead all the way and never saw another horse in the race. A thrill.

What was the most pressure you ever felt before a race?

Without doubt, the 1989 Gold Cup.

We had won seven or eight major races leading up to it and were very much the hot favourites. I genuinely felt I had the best horse in the race Desert Orchid.

The concern was that he preferred racing right-handed and had never really produced his very best form at Cheltenham. Had the race been at Ascot or Kempton, I would have felt we were absolute certainties, but Cheltenham was always a question mark.

Because he was such a popular horse and had such a huge following, there was a lot of pressure attached to the occasion.

Everything went perfectly in the build-up, but the weather on the day was dreadful, which added another challenge. The media attention surrounding Cheltenham is enormous and the pressure builds steadily as race time approaches. Looking back, that was certainly the most pressure I ever felt before a race.

Who was the funniest or best character in the weighing room?

My best mate in the weighing room was Steve Smith Eccles.

When I first entered racing, it could be a very serious and all-consuming environment. If you had a bad day, especially if a couple of fancied horses had been beaten, you could leave the racecourse dwelling on everything that had gone wrong.

Steve had an incredible ability to put things into perspective. He would always remind you that you were healthy, in one piece and that there was always another day tomorrow.

From that perspective, Steve was a real friend, and I will always be eternally grateful to him for being such a good guy.

What makes a track like Ludlow unique, and what does racing mean to communities like Ludlow?

Ludlow is a wonderfully quirky racecourse. It’s a very fast track and features road crossings, which makes it quite a challenging place for jockeys to ride.

The ground can also present its own challenges due to the gravel base and the varying weather conditions throughout the season.

What really makes Ludlow special is that it retains a friendly, personal atmosphere. We aren’t overly corporate. We like to speak directly to our members and customers, whether that’s face-to-face or over the phone.

The feedback we receive from owners, trainers, members and racegoers is consistently that they’ve enjoyed a warm and engaging day out.

That’s something we must always protect. It isn’t something that can be created overnight. It’s been built over many years by previous staff and our excellent front-of-house team. It’s something we’re very proud of and keen to preserve.

How can racing attract younger and wider audiences?

It’s certainly a challenge, particularly at Ludlow where most of our fixtures take place during the week when many people are working.

The welfare of our horses must remain at the heart of everything we do. Racing needs to be accountable at all times and we must continue to ensure that every possible measure is taken to safeguard both horses and riders.

Many racecourses are doing an excellent job engaging younger audiences. Universities are becoming increasingly involved and if you look at Cheltenham now, the crowd is noticeably younger than it once was.

My hope is that people come not only for a great day out, but also develop a genuine interest and passion for the sport itself. That’s what creates long-term supporters.

At Ludlow, fixtures such as our Christmas Meeting and Sunday meetings help attract a younger audience. I want racing to feel welcoming and inclusive for everyone. It should never be an “us and them” environment. We want everyone who visits Ludlow to have a fun and memorable day.

Two fun ones – favourite food of all time?

I’m very traditional. I love a good steak and chips, cooked medium-rare.

I also have a serious weakness for puddings. Anything with custard on it is hard to beat. It’s probably not great for the waistline, but who cares?

Dream dinner guest?

First of all, someone like Nelson Mandela. He seemed such a humble and inspirational person, and I think he’d make most people’s list.

From the sporting world, I’d choose Jimmy Greaves. He was a hero of mine and a Tottenham Hotspur legend. I met him briefly once and he was incredibly funny and entertaining.

I’d also happily spend an evening talking to John Francome. He’s always engaging, knowledgeable and great company.

More generally, I love talking to people who have excelled in sport. Someone like Jonny Wilkinson would be fascinating. He might be a little serious at times, but the opportunity to learn from someone who achieved so much at the highest level would be brilliant.

Your favourite racehorse, past or present?

I could give the obvious answer and say Desert Orchid, because he was undoubtedly one of my all-time favourites.

However, I think Frankel was simply extraordinary.

What made Frankel’s story even more special was the timing. He arrived when Sir Henry Cecil was facing serious health challenges and almost felt like a gift from above. Frankel allowed Henry to once again showcase his brilliance to the wider public and receive the recognition he so thoroughly deserved as one of racing’s greatest trainers.