The brothers, William, Frank and Ted followed their father into the boat-building business. The business, now named "Dey Brothers" had a boat works on the Rideau Canal at Theodore Street (today's Laurier Avenue), where they built small boats and canoes for racing. The Dey brothers built their first indoor skating rink next to the boat works in 1884. The brothers would also become involved in the new sport of ice hockey at their rink. Ted Dey himself played games for the Ottawa Hockey Club (as the Senators were then known) in 1887, 1889 and 1890. The rink would also become home to its own team the 'Dey's Rink Pirates', founding members of the Ottawa City Hockey League in 1890.
The building of the Canada Atlantic Railway tracks along the Rideau Canal as far north as Rideau Street meant the demolition of the boat works in 1895. The brothers built a new boat works at Patterson Creek and Bank Street, and a new skating rink at Bay Street and Gladstone Avenue. The Dey's Skating Rink was the location of the first Stanley Cup win for the Ottawa Hockey Club. A third arena was built near the original skating rink, on the opposite bank of the Rideau Canal, and was known as The Arena, opening in 1907. The second skating rink was eventually demolished in 1920 after a fire, and the third rink in 1927 after its lease for the land expired.
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