Robert is from Red Pheasant Cree Nation, located 30 minutes south of Battleford Saskatchewan and was raised in Calgary.
His father Jimmy, a survivor of the Canadian Indian residential school’s system, is mixed Cree & Métis and from the Red Pheasant First Nation.
Robert was raised primarily by his mother Sharon, who was born in Tottenham, North London and moved from England to Canada in 1974. Robert’s namesake is his uncle, Robert-Falcon Green, who died in 1961 at age 9.
Robert grew up in poor conditions and determined to change her son's future, his mother insisted that he take the admissions test for the Strathcona-Tweedsmuir School, a private school in Calgary. After he was admitted, his mother paid for his tuition by taking out a loan she could not afford to pay back.
Robert earned a Bachelor of Arts in music from the University of Calgary in 2001. In 2004 and 2007 he earned a Master's in Music and a Master's in Education from Laval University in Quebec City. In 2011 he completed his PhD in anthropology, also from Laval University. He was only the 2nd indigenous person in the 350-year history of Laval University to earn a PhD.
While attending university in Quebec City he also worked full time in the Canadian Army, which required him to complete his course material at night or occasionally in the field. After having been posted to the Royal 22e Regiment, a French-Canadian military unit, he learned to fluently speak, write and read French,
From 2007 to 2010 he was appointed a Company Commander in the 5e ambulance du campagne or 5th Field Ambulance (the medical service) where he was responsible for helping run the base hospital. He retired from the Royal Canadian Navy after nearly two decades of service with the rank of Petty Officer 1st class and remains as part of the Primary Reserves in the Royal Winnipeg Rifles as a Warrant Officer.
In 2011 Robert moved from Quebec City to Winnipeg after he was appointed as director of the Aboriginal Focus Program at the University of Manitoba.
As Member of Parliament for the riding of Winnipeg Centre from 2015 to 2019, he also concurrently served as a non-commissioned member of the Canadian Armed Forces.