Todd Sherman is a pioneering owner-operator who believes the true essence of hospitality cannot be stripped down to a spreadsheet. As Partner and CEO of Urban Dining Group, a premier multi-branded restaurant company in Toronto, Todd has spent nearly four decades shaping the Canadian dining landscape. What began as a family venture remains one to this day: Todd now oversees the business in partnership with his parents, Grant and Judy, who started the company in 1989, and that family-company ethos still anchors everything the group does. Under his leadership, Urban Dining Group has developed and operated iconic spaces ranging from the beloved neighbourhood staple Gabby’s to massive waterfront destinations like the Amsterdam Brewhouse and Barrelhouse (a former partnership with Amsterdam), the only NBA Courtside Restaurant in the world, and the iconic Hey Lucy’s Italian on King West in Toronto. Despite managing a portfolio of this scale, Todd remains intimately involved in the physical design and build of every single location, driven by an obsession with detail and human connection for spaces.
Todd’s hospitality journey began at just 15 years old, working at a local sandwich shop in Richmond Hill. Mentored by an older owner who meticulously placed every ingredient and treated each guest like family, Todd learned early that people don’t just come for the food, they come for the people. By 17, he was the youngest manager in the region. In 1989, his parents put everything on the line, mortgaging their home to open the very first Gabby’s at Yonge and Lawrence, and bringing Todd into the new family business. Still in high school and too young to legally drink, Todd cut chicken wings, cleaned floors, and helped build what would become a North Toronto institution, a place he fondly calls the “original social media,” where neighbours actually connected face to face.
Today, Todd fundamentally rejects the short-term, “two-to-five-year mandate” mindset of corporate CEOs. Instead, he operates on decade-long roadmaps, creating spaces designed specifically to foster belonging, even intentionally using narrower dining tables to bring people closer together. Fiercely protective of his team and his franchisees, and proud of the family company that now also employs two of his brothers and his oldest son, Ryan, Todd’s goal is to build a legacy brand that prioritizes the guest experience over immediate margins, proving that in an increasingly digital world, human connection is the ultimate competitive advantage.
