Joseph Oleskiw was born in the village of Nova Skvariava (Nowa Skwarzawa), near Zhovkva, in the Austro-Hungarian province of Galicia (now western Ukraine).

[2] Ukrainian immigrants who had travelled to Brazil and Argentina, enticed by the free transportation they had received, sent back word that conditions there were worse than in their homeland.

This led to Oleskiw writing two pamphlets in Ukrainian – "On Free Lands" (Pro Vilni Zemli,[1][3] spring 1895), and "On Emigration" (O emigratsiy,[4] December 1895) – and one in Polish.

[6] Because of Oleskiw's efforts, on the one hand, and the Canadian government's direct involvement, on the other, the flow of Ukrainians to Canada was much more targeted and organized than that to the United States.

[5] Oleskiw was particularly interested in the area of Stony Plain, District of Alberta, due west of Edmonton, where a number of German settlements had been started.

His first group of settlers were thirty hand-picked families, led by his brother Vladymir (Volodymyr), who arrived in Canada in Quebec City on April 30, 1896.

[9] Genik preferred Stuartburn, a district not recommended by Oleskiw; as it was close to the large Mennonite settlement near Gretna, and commercial farms in North Dakota and Minnesota, where those Ukrainians who needed cash might earn some extra money.

Second, in attempting to regulate the number of peasants leaving Western Ukraine in any given year, he tried to prevent Galician land prices from falling drastically; though in this he was only partially successful.