Justin O'Brien was born and raised in Thunder Bay, Ontario. Being the first grandson of Pasquale and Sisina DiPaolo, he was introduced to the Italian culture at a young age and soon learned the importance of family, faith, and food.

In 2013, Justin graduated from Lakehead University with a Master's Degree in History. He had written an essay for a Northern Ontario History course that examined local Italians before and during the Second World War. This paper would inspire Justin to continue his research in the years that followed and utilize various sources such as interviews, memoirs, and newspapers. Justin shared what he had learned with the general public in April 2019 when he delivered a Speaker Series titled "Good Sons of Italy, Good Citizens of Canada: Early Italian Settlement at the Lakehead" on behalf of the Institute of Italian Studies. One month later, he officially joined the institute's board of directors. Though he now resides in the Ontario township of Selwyn, Justin remains a steadfast member of the board and continues to think of new and innovative ways to promote Italian culture in Thunder Bay.