How did you get involved in racing and breeding?

My family have had horses with the O’Briens going back 45 years. My father had horses in training with Frank, David’s father, and with David himself. I’ve had horses with David going back 20 years, maybe even a little bit more. My grandfather was interested in racing and my parents had a family business, so the only holidays they ever took were to escape to the races. I’ve been going racing since I was knee-high.

My dad started breeding later on, when I was younger, he mainly just had horses in training, and then he started to get into breeding.

David selected Mic Drop’s dam Is Herself About for me at the Derby Sale in 2010. She picked up a few races over hurdles and fences and I started breeding off her then after she retired.

It’s great to carry on the family tradition and it’s nice to support David with the family connection we have. He treats his horses very well. He has a limited number of loyal owners and he really deserves a lot more support. It’s a tough business out there, both for owners and trainers!

Were you at Wexford for Mic Drop’s win on Tuesday?

I’m on holiday in Columbia, so I was watching it early in the morning here, but it was worth it. He’s a big horse and he’s taken a bit of time. He won his point-to-point and his bumper, but the yard had a few problems over the winter period, so we had to be a bit patient and wait for them to come right again. David is good at taking his time with horses and letting them develop as they need to.

Were you confident going into the run?

No, actually, I’ve been a lot more confident going racing on days when things haven’t worked out! I think he looked impressive, but he was probably a little bit flat with how the race panned out. The race kind of fell apart with the fast pace. He had such a light weight and, with the extra allowance from Josh (Williamson, jockey), it really played into his hands.

He can be a little bit keen, so the pace forced him to settle, so he got a bit of an education as well as everything else. There were a couple of other horses that I thought would definitely beat him, so it was a very pleasant surprise. We’ll have to see what the handicapper does now, but given how it looked he’s not going to be too kind, particularly with him bouncing off a previous win.

There’s a nice handicap chase in Killarney that we might look at. I’d love to have a winner at the Galway Festival, but I don’t think there’s a race there to suit him.

You mentioned earlier that it’s a tough business, what hardships have you been through, and how did you deal with them?

We had a nice Milan colt foal out of Is Herself About and he had a bad reaction to an injection, and we lost him at about three years of age before he ever got to run, and then we lost another offspring out of the dam as well.

You put a lot of time and money and effort and love into it, and the rewards can be few and far between. Racing has got so competitive with the bigger owners, it’s tough.

Particularly because I travel a bit, it’s really about keeping tradition going for my father, who passed away a few years ago, more than anything at this stage. I bought two horses at the Derby Sale in 2010 and we named them Is Herself About and Is Himself About. The much more expensive one was the gelding and he ended up clipping heels in his second bumper and having to be put down.

That was a huge blow, but you have to take the rough with the smooth. I suppose the whole thing is the impossible dream of one day leading up a winner in Cheltenham.

That’s what keeps a lot of people in it. I’d love to do that for Dad, I’d love to have a proper horse one day and for him to be looking down and smiling.

I remember when I was a young kid, and Frank telling me, ‘What you need to do now is buy a broodmare and breed off it, and that way you’ll get to dream for a number of years before you get disappointed’. And it’s true I suppose, it’s all about the dream, and the longer you can keep that dream going, the better it is.

What’s been a highlight for you?

Mic Drop winning his bumper was probably a highlight for me. We’ve had very few bumper winners over the years, so that was something special.

Particularly when you get a winner early on like that, with a horse that’s won his point-to-point and his bumper, you start to dream that maybe you’ll have a proper horse.

Do you always race the horses you breed?

Is Herself About has been difficult to get into foal the last few years, so this is probably her last chance.

When Bossing It retires, I’ll probably continue to breed off her and hopefully we can get a few more wins into her before she goes to become a broodmare. When I started breeding, I hoped to get an early win with her offspring on the track and then go to the sales, but it just didn’t work out like that.

I’ve ended up running all of them so far, rather than selling them. It’s also nice to sell them and see them win for someone else, and to lodge a cheque every now and again! I’m not specifically breeding them to run or to sell, it’s just the roll of the dice. There’s a lot of superstition involved in racing, and you believe things happen for a reason, and it’s the only way you can keep yourself sane.

How do you go about making decisions such as covering mares or race planning?

It’s really tricky. I find that covering the mares is the most difficult part for me. You’re looking for a little bit of cross-breeding, but not too much, and now the trend seems to be no cross-breeding at all. That side of things is really tricky for me. When they ring me every year, telling me I need to start thinking about who I want to get her covered with, it’s always a panic. It’s really intricate. The piece I enjoy is the race planning. I really like going through the agenda and trying to find niche races for horses that give them a chance.

Has your background in accountancy made your experience as an owner easier when it comes to planning finances?

I don’t think there’s any part of my life that I treat in the same way financially as I treat horses. You have to be realistic and you have to accept that any money you invest is likely to be lost.

Having a deep family background in horses, I didn’t come from a place where my friend bought a horse and got lucky and made a load of money and had an unrealistic expectation of things.

A little bit of financial planning is needed, because you have to understand what can go wrong, what’s the worst-case scenario, and you have to make sure it’s not impacting other parts of your life.

I think it’s helpful that I’ve always been good with numbers, so I haven’t got myself into trouble with horses. It’s an advantage, but I never look at it as an investment, I look at it as a sport or a hobby.