Investing in a race horse for the first time is a daunting endeavor indeed. We visited Saratoga Race Course and spoke with BSW/Crow founder Bradley Weisbord to learn what it takes to win.

Bradley Weisbord at Saratoga Race Course with celebrity chef and horse owner and breeder Bobby Flay

What exactly does BSW/Crow do in terms of the sport?

We are a company that consults in terms of buying, selling and managing horses to help our clients win. The goal of all owners is to buy a champion thoroughbred, and we are fortunate to work with clients who have had eight champions since we started in 2014. As an example, we purchased champion Monomoy Girl in 2016 as a 1-year-old horse (yearling) for $100,000; she went on to win the Kentucky Oaks and Breeders’ Cup Distaff twice before selling at public auction in November of 2020 for $9.5 million. Year after year our goal is to win the biggest races in the sport. We have won the Kentucky Derby twice as well as the Preakness and Belmont Stakes.

Our company is unique in that my partner Liz Crow is an expert in finding these horses at a young age—whether that’s weanling, yearling or 2-year-old. And my focus is to work with our clients to find horses when they start to run as was the case with Justify, who won the Triple Crown; Creator, who won the Belmont Stakes; and Exaggerator, who won the Preakness. On top of this buying and selling, we also manage many stables. We have 35 active clients that we manage, which includes 500 horses.

Weisbord discussing race strategy with leading jockeys Irad Ortiz Jr. and Jose Ortiz

Paddock access courtesy of Alysse Jacobs and Harper Gray, Horsemen’s Relations at The New York Racing Association

What advice do you give to people who are thinking about entering the sport for the first time?

I think it’s very important to start small. You need a great adviser to answer all of your questions, explain to you how the sport works and help you understand the benefits of joining a partnership. When you join a partnership it’s the best way to learn, and that way you can get an interest in a couple of horses. You have to buy a number of horses to increase the probability of success. It’s very unlikely that your first horse is going to be a stakes winner or even a maiden winner at one of the top-tier racetracks. You want to take a little piece of a horse and buy a couple of them, and that way if you buy five or six horses, you’re going to get one that wins. It gives you a little taste of, ‘This could be something.’ Then you’ll be down the path to potential success.

Start to ask the right questions. What’s a horse worth? If it wins this race, what’s the next step for the horse? Who are the trainers that would train the horses? Do we use multiple trainers? You start to meet the trainers and decide which personalities mesh with yours. There are a lot of different personalities. I would encourage you to meet the trainers.

I like to meet with my clients before they get into the business and try to understand what the client is looking for. If the client is looking to make money, I always tell them to go buy bonds because you should never get into the horse business to strictly make money. The worst thing you can do is enter the thoroughbred horse business to make money. Of course you can make money—I can give you a hundred different examples of home runs that we’ve hit in the thoroughbred horse business. Don’t get into the business to necessarily make money; get into it for the camaraderie, for the love of the animal and for the weekends and the days at the racetrack and the training centers. Much like golfing, yachting or fishing, you find a hobby and you want to spend the time at the track. I call it sport, not business. There is a financial relationship with this business, but that’s not why you get involved.

Before you invest, you have to go and spend time at the races. And there are resources in daily journals like TDN, the Thoroughbred Daily News, which is the Wall Street Journal of the horse business.

Think of it as a portfolio. My best advice is to get an adviser and to buy a piece of a basket. Instead of buying into one, buy into a couple, like stocks. Buy one share of Apple, one share of Tesla, one share of Microsoft and one share of Netflix. That’s going to give you your best success because that way, you have enough money to spend the second year. You need to give yourself the best chance to get to that winner’s circle because that winner’s circle... it’s contagious.

Champion trainer Chad Brown clocking a thoroughbred’s weekly breeze

In the paddock prior to the race with expert handicapper Jonathon Kinchen

When You Become A Horseman, Enjoy Après Racing

When speaking to a “horseman,” the term most frequently used to classify a man or woman who has an ownership stake in a thoroughbred, the conversation tends to revolve around three questions at the big tracks, like Saratoga. First, “Do you have a horse racing this week?” Second, “What horses do you like today?” (to wager on). And lastly, “Where are you going for drinks and dinner tonight?”

The ritual of a day at the track followed by “après racing” and then dinner seems to take on a life of its own for the horseman. You’ll find them enjoying an ice-cold martini with perfect olives at Siros shaken by Woody or Brianna, admiring the aroma of a char-seared pork chop with peppers that might be the best thing you’ve ever tasted at Osteria Danny, surveying a dish of broccoli rabe and sausage that begs one to dunk crusty bread into the aglio e olio sauce at Taverna Nova, or perhaps they are among the luckiest who walk around the corner and are invited by a member to close out the evening with a cigar and drinks after dinner on the patio of the “buzzer-entrance-only” 100-plus-year-old Principessa Elena Society social club.