Millennial generation entrepreneurs are showing a higher than average interest in starting new companies. This generation is key to economic success in Canada since the millennial generation comprises roughly 25% of the Canadian population. Mentors may make the difference between success and failure of these new ventures. This multiple case study explored 6 millennial generation small business owners participating in the Futurpreneur Canada mentoring program. Data included semistructured interviews with participants of the Futurpreneur mentoring program, experience profiles of these participants, and public information about the Futurpreneur program. The analysis of the data demonstrated that mentors provided career support by serving in the following roles: (a) advisor for entering new markets, (b) connector to experts, and (c) advisor on a business function. Insights from this study may help program designers, entrepreneurs, and mentors work together to enable entrepreneurs to develop their organizations and set them on the path to success.