Sheila Rosenblum doesn’t like to take no for an answer. “It may be the death of me in the end,” the Manhattan social fixture says. “Life should be about calculated risks, and not all of mine have come with calculation.”
As the founder of Lady Sheila Stable Two, an all-female horse-racing group based on Long Island, she’s had to not only embrace but also learn to revel in the reality of risk. It’s something the former ballet dancer and Ford model has taken to wholeheartedly.
Rosenblum had flirted with the erudite equestrian pastimes of jumping and dressage for years, but in 2010, when her then husband, Daniel, offered to buy her a world-class dressage horse, she decided she’d take a racehorse instead. Admittedly, her first few years in the horse-racing business were a string of missteps—“I’ve made mistakes, some really expensive mistakes,” she says—and industry types seemed to think she was a deep-pocketed, flash-in-the-pan investor who would leave the field as quickly as she entered it. In one early snafu, she was sold a horse that wasn’t technically for sale, an ordeal that ultimately required the involvement of the FBI and Hillary Clinton.
Rosenblum’s luck changed, however, when she met Linda Rice, a horse trainer based on Long Island. “I didn’t seek out a female trainer, but she just blew me away,” says Rosenblum. “I wanted a New York trainer because I wanted to touch my horses and feed them, to watch them train in zero degrees and 100 degrees. I wanted a trainer who would take the time to answer questions because I wanted to learn. I didn’t just want to write a check and say, ‘Hey, go do what you want.’ ”
Still, it is a business, and that’s why Rosenblum has rounded up a cabal of eager investors—what’s known as a syndicate in the equestrian world—to co-own a literal stable of horses. “I surrounded myself with an incredible team,” she says. Some were old friends, some she knew only socially, but they each had a zeal for investing their money in a new endeavor. “We were all looking for something just a little different, something outside of our sense of security,” she says.
First to sign on was Rosenblum’s longtime friend Jill Zarin, best known for her stint on The Real Housewives of New York City, who in turn brought in Dottie Herman, the CEO of Douglas Elliman. Donna Bernstein, the celebrated horse painter, also asked to meet with Rosenblum—“I thought she was trying to sell me art,” Rosenblum says—and philanthropist Iris Smith soon joined the group as well. “It’s all bright, hardworking women. We weren’t necessarily friends from the start, but we’ve become that,” Rosenblum says. “I have a lot of girlfriends who want to be involved and I say, you can’t. It’s very expensive, it’s very slow, it’s not for the weak of heart, and it’s not an area to go into if one can’t lose the money she’s investing.”
So, what gives Rosenblum the moxie to carry out such a risky endeavor? Having spent her adolescence training at the strict Royal Ballet School in London and later the School of American Ballet, Rosenblum grew up avoiding any and all hazardous behavior. With her dancing days behind her, however, she’s now able to dabble in more daring affairs. “I’ve been making up for everything since my twenties!” she says with a hearty laugh.
But racing is anything but a heartless undertaking. Of her star sprinter, La Verdad, who is a favorite to win this year’s New York–Bred Divisional Championship, Rosenblum says, “I’m emotionally involved. I was advised by two vets not to buy this horse, and yet I did.” Though the eight investors—also included are Diane Davis and Jessie Laiken—are rarely in the same city at the same time, they all came together this April to root on La Verdad at a race in Saratoga, where they also had an official shareholders’ dinner and celebration at the Saratoga National Golf Club. Rosenblum might have once been known for her Upper East Side soirées, but these are the sorts of places she’s logging time in now.
Indeed, if you find yourself at Belmont or at Saratoga, Lady Sheila Stable Two horses—there are three in total—aren’t hard to spot.
“I chose the tackiest combination of colors that I could humanly find, which is bubblegum pink and neon blue,” Rosenblum says.
“I wanted to pick something that I could see from really far away when I get older.” And just like that Rosenblum demonstrates that even from the beginning, when everyone doubted her longevity, she was always thinking long-term. “My kids told me that I promised everyone I’d quit if my second trainer didn’t work out,” she remembers. (Rice is her third.) “But I have the luxury of changing my mind.”