Blackwood was born in Alberta, Canada, and grew up in Prince Edward Island as the eldest of ten children.

[3][4] Blackwood lectures and writes on the intellectual and cultural development of the West, and specializes in the history of philosophy,[5] especially Boethius.

[9][10] Blackwood was a founding executive director of St George's YouthNet,[11][12] an educational mentoring program for inner-city youth in the North End district of Halifax, Nova Scotia.

[18] His op-ed[19] in the Wall Street Journal about his mother's loss of her cancer coverage as a consequence of the Affordable Care Act was read on the floor of the US Senate and entered into the Congressional Record.

[20][21][22] Blackwood was the host and moderator of a conversation between Jordan Peterson and Sir Roger Scruton at Cambridge University on November 2, 2018.