But the 51-year-old's Toronto-based business — Freedman's — isn't exactly a household name in Canada.
"I think you're least recognized at home," said Freedman, the sixth generation in a business that began in Poland in 1802.
"I think that's one of the reasons why we're such big exporters. That's not saying something about Canadians as a people, I think our country is just so vast in comparison to a country like the States and it's just harder to get across and do business different places."
While the average Canadian may have yet to learn about Freedman's reach, his business has made its mark in international circles.
"Our name is synonymous with quality," said Freedman. "We have a global reputation that we've built over the years that we keep. We keep it by visiting horse shows around the world, visiting with clients and serving our clients."
Those clients have come to include Martha Stewart — who featured a Freedman's bridle on the cover of her magazine a few years ago — various royal families, and beermakers Budweiser and Carlsberg.
The products that go out to Freedman's approximately 3,500 international clients are crafted in a workshop on a quiet street in north Toronto.
"Everything is handmade," said Freedman, walking past artisans hammering away at horse collars and painstakingly sewing parts of a harness together. "We try and deliver the best possible quality in the world."
But it's been a long journey to the top.
The business came to Canada in 1910, when Freedman's grandfather opened a harness shop in Toronto's Kensington Market. Freedman's father joined the business at the age of ten, choosing harness-making over school and going on to work his way through the Second World War.
Things got tough as horses made way for automobiles, but a breakthrough in standardbred racing sustained the business. Freedman's then took advantage of the "carriage revival" in the mid-70s and '80s, when people started restoring antique carriages for personal use.
"There wasn't a lot of harness from days gone by — it had rotted away or burned up in fires — and it needed to be all then either restored or recreated and my father was one of the only people around who could do that type of work on the continent," said Freedman.
The business's international clientele continued to grow in the 1960s, when some Canadian patrons began using the Freedman's equipment in England, Germany, France and Amsterdam.
For his part, Freedman decided to get involved in the family business full-time at the age of 18.
"I think you have to be a little bit unconscious about being second, third, fourth, fifth — in my case sixth — generation doing the same thing in your family," he said with a laugh. "If you think about it too much you probably wouldn't be able to carry this on because it's a pretty daunting task."
There was a time in 1991, just after his father died, that Freedman found himself questioning the direction of his business, which had grown to include leather bags and belts.
"The core competency of the business in carriage driving was sort of dwindling away. We were known as building the best product, but you really couldn't find it because we weren't really building that much of it," he said.
"I guess I had an awakening where I was like, 'I really don't want this bag and belt business anymore. I want to go back to doing what we do best and what the company does best and what the company is famous for.' So I embarked on a journey to recreate the past of high-end harness making."
After years of focusing on that goal, Freedman, ironically, made a return to including bags, belts and other leather goods in his business in the mid-2000s after requests from clients, and now even has a retail store in Kentucky.
"Our clients are demanding the best that they can buy anywhere. That sort of defines the work," he said. "Someone once said to me, 'Gee, you're really smart coming up with all these ideas.' I said, 'I haven't come up with any ideas, I've only developed them. They've come from my clients.'"