Born in Farmington, Connecticut, he moved to Chippawa, Upper Canada, after his father was murdered.
In Chippawa he lived with his uncle, Samuel Street, who introduced him to the local business community.
His most prominent partnership was with Thomas Clark, and together they used the profits from the mills to lend money (and charge interest) to various people in Upper Canada, further increasing their wealth.
He died in Port Robinson, Upper Canada, and his estate was given to his son, Thomas Clark Street, and four daughters.
In October 1796, Street Jr was granted 600 acres by the British government because he was the son of a loyalist.
This caused a lengthy legal battle over the status of the property and Randal highlighted this event in his opposition to the Niagara region's elite, which included Street.
[2] He was well connected with local officials in various regions and lent them money for public work projects in exchange for preferential treatment on purchasing property.
Local officials would also notify him when land was to be sold at cheaper rates due to a sheriff's sale.
[1] In the 1830s Street and Clark build a wooden walkway around their property at The Burning Springs in the Niagara region.
[1] In 1841, Street purchased shares in the Welland Canal Company, which were exchanged for debentures issued by the Upper Canadian government.
Merritt also informed Street of a bill in the Upper Canadian legislature that, if passed, would further increase the value of the canal's stocks.
His estate and land holdings were given to his son, and his four living daughters, and totalled 15,680 acres in Upper Canada.
[1] Upon his death, Street was negatively described in a local newspaper called the St. Catharines Journal as a businessman who ensured he received the total amount owed to him in interest when he lent money to others.