UK markets closed
  • FTSE 100

    +71.78 (+0.91%)
  • FTSE 250

    -65.63 (-0.33%)
  • AIM

    -2.92 (-0.38%)

    -0.0007 (-0.06%)

    -0.0104 (-0.83%)
  • Bitcoin GBP

    -2,769.33 (-4.87%)
  • CMC Crypto 200

    0.00 (0.00%)
  • S&P 500

    -75.65 (-1.46%)
  • DOW

    -475.84 (-1.24%)

    +0.43 (+0.51%)

    -12.50 (-0.53%)
  • NIKKEI 225

    +80.92 (+0.21%)

    -373.34 (-2.18%)
  • DAX

    -24.16 (-0.13%)
  • CAC 40

    -12.91 (-0.16%)

My first boss: Harry Herbert, founder of Highclere Thoroughbred Racing

yahoo finance uk
Horse Racing - Royal Ascot - Ascot Racecourse - 19/6/08 
Manager of Highclere Thoroughbread Racing , Harry Herbert celebrates after his horse Collection won the 4.55 Hampton Court Stakes   
Mandatory Credit: Action Images / Scott Heavey
Harry Herbert's career in racing was forged in Kentucky by businessman Barry Weisbord. Photo: Action Images/Scott Heavey (AI Project / reuters)

Harry Herbert is the founder, chairman and managing director of Newbury-based Highclere Thoroughbred Racing (HTR), Europe's leading racehorse ownership company.

Since launching HTR in 1992, the company has spent £45m on bloodstock, with total sale proceeds at £44m and prize money of over £10m. Notably, 21% of Highclere’s syndicate shares produce ‘black type’ horses capable of running in the top races in the sport. Born at Highclere Castle, Herbert is the Queen’s godson and is married to Irish chef and TV cook Clodagh McKenna.

Before Barry Weisbord changed my life, I was like a dormant gene ready to wake up.


Racing was ensconced in my family, it was spoken about at every meal but this put me off and I had no interest in the sport.

I had aspired to be an actor but that was never going to happen and so I licked stamps in the City for stockbrokers’ Rowe and Pitman for a few years. I used to go to the bookmakers at lunch and bantered on the floor of the Exchange about horses and I began to get hooked on the sport.

My father was well known in every part of racing, looking after the Queen’s horses for many years, and so I felt like I had to head to the United States.

Read more: My first boss: Anne Boden, CEO and founder of Starling Bank

I initially got a job with computer firm Bloodstock Research, which specialised in pedigrees. I was soon hired away by Barry, who was so gobsmacked by a letter I had written him after his mares were sent to be put through the computer.

I wasn’t very academically minded at school but the one thing I was told at Eton by my housemaster as I left was, ‘If nothing else, Mr Herbert, what we have taught you here is how to write a letter.’

Barry had set up a company in Kentucky called Matchmaker trading shares and nominations, which are the annual breeding rights to a stallion. No one had ever done this before in the industry.

Sir Alex Ferguson and Managing Director of Highclere Racing Harry Herbert (left) at Ascot Racecourse.
Sir Alex Ferguson and Highclere Racing's Harry Herbert share a joke at Ascot Racecourse. Photo: PA (PA)

Being lured away to work with Barry was the most fantastic moment of my life. He is still the most remarkable man and he gave me such confidence, never put anyone down and any idea was welcome.

He had also identified a lack of opportunity for those who really wanted to get involved in buying horses. He wanted to open it up and created a simple electronic ‘bid and ask’ market of what the real value of stallions was. We were dealing with anything from a couple of thousand dollars to several million. It took a lot of stick for something so new in the market but it played a huge part in the sport. Barry also recognised that racecourses should be putting on more turf festivals and more international racing.

There was never a dull moment working under him. A quick brain, he acquired a good portfolio of stallion shares, while he also branched out and started Thoroughbred Daily News. Way before email, where fax had just started rolling, he delivered a daily electronic news service for owners and breeders of racehorses. It was before its time with loads of reports coming in, but is now the leading global flow of information in racing.

Matchmaker got into an array of dynamic areas, from racecourse management to finance and bloodstock insurance market in London, and the variety opened my eyes to what was achievable in the sport.

LOUISVILLE, KY - NOVEMBER 03:  Barry Weisbord attends
Barry Weisbord pictured at Louisville Executive Aviation Hangar in 2011 in Louisville, Kentucky. Photo: Stephen Cohen/Getty (Stephen Cohen via Getty Images)

We never had a bad word against each other and, as a boss, Barry taught me that instilling confidence is so important in business and it helped me set up Matchmaker UK three years later when I moved back to the UK in the mid 1980s.

I soon started a syndicate company which I thought was the way forward for racing. Bankrolled by two investors, it was successful for four years until recession kicked in. And so I went it alone and Highclere Thoroughbred Racing was started in 1992. Thirty years later, we are still leading the way in the multiple ownership field.

It’s all about making racehorse ownership cost effective. Highclere gives owners the opportunity to take small groups of people to share in a number of horses and know exactly what they are putting in, at a fraction of what it costs in training shares.

Owner Harry Herbert celebrates with the trophy after Cachet ridden by jockey James Doyle wins the Qipco 1000 Guineas Stakes on day three of the QIPCO Guineas Festival at Newmarket Racecourse, Newmarket. Picture date: Sunday May 1, 2022.
Harry Herbert celebrates with the trophy after Cachet wins the Qipco 1000 Guineas Stakes at Newmarket Racecourse in May. Photo: PA (PA)

We’ve always believed that a personal service is also essential to make every owner feel they are the only owner of the horse. We effectively act as racing manager to every one of our share owners. The Highclere-owned Cachet won the 1,000 Guineas this year, which was our first domestic Classic winner. We’ve run seven European champions and Royal Ascot winners and so it’s about giving prospective owners a realistic chance of winning.

Read more: My first boss: Ugo Monye, former England rugby star

No one comes into this as a money-making venture; it’s purely for the fun. But from our perspective, managing the horses, good or bad, is key to making sure we sell at the right point and to give as much as possible back to the syndicate.

Do I still write letters today? Well, not as much, but in my business with selling shares in racehorses, it’s about how you sell that horse and how you portray the story behind the purchase of the animal, the pedigree, looks and movement. It’s a key part if it’s well written, even if it’s in email form today.

I have remained the best of friends with Barry to this day and he is the man I look back to who made it all happen for me.

Highclere Thoroughbred Racing race around 50 horses each year. Currently in yearling buying season, HTR will parade its horses at Highclere Stud in mid-October.

Watch: Why do we still have a gender pay gap?