As a young man, Reid spent a few years in Australia mining gold.

[1] In 1898, he further contracted to work all the railways in Newfoundland for fifty years on condition that at the end of this time they should become his property.

Public opinion was aroused against the deal, and at first the governor, Sir Herbert Murray, refused to ratify it.

[1] After the premier, James Spearman Winter, had been replaced by Robert Bond, the terms of the contract were revised, being made more favourable to Newfoundland, and Reid's interests were transferred to a company, the Reid Newfoundland Company, of which he was the first president.

The Reid Newfoundland Company owned and operated the Whitbourne to Port aux Basques railway for 33 years and also ran the coastal boat and telegraph services on the island.