Cynthia Hastings-James was born in Halifax, spent summers in PEI before moving to England when she was three. She viewed herself as a Tomboy as she was growing up. Her father worked for an oil company and the family moved to Calgary where as a soccer player she met Wayne Gretzky and his father. Then the family moved to Toronto where she went to high school and received a BA from Western.

She had a quest to be independent and successful and in her first full time job dabbled in online work with a news organization. From there to Bell, health care and digital marketing. She was recruited into MD Briefcase to offer certification courses and started a similar program for pharmacists. 
Using the skills she was learning she started a rewards program and then started a patient rewards program in 2011 and enjoyed three years of success.
She was invited to the Cayman Islands to give a talk on health behaviour change and was invited to start a rewards program there. That lead back to Canada and the Canadian Insurance Industry where her company (she had a partner) was bought out by Goldman Sachs in 2021.