KC Daya is the CEO and founder of Clifton Blake, a vertically integrated builder, lender, and operator of Multi-Family assets. We discuss the impact of his immigrant entrepreneurial parents and how this spills over into his parenting. We discuss how his first fund failed and the valuable lessons this taught him. As well, we discuss the transformational mergers that have made his business vertically integrated.

Jeffrey McCain is the 3rd generation of the McCain family and the President of Woodword Capital. In this episode, we discuss working outside the business on Wall Street and his motivations for returning to work with his family. Jeffrey shares his latest investment strategy and how family offices stand apart from traditional private equity. We discuss how his family onboards new family members and the role they are expected to play. Lastly, he shares salient advice from his grandfather, Wallace McCain, on charitable giving.

Ian Wilson is the 8th-generation President and co-owner of Wilsons. They are an Atlantic Canadian family with investments in the fuel industry, home security, and quick-serve restaurants. Ian shares the incredible history of their family business and how his own journey wove into the family story. As well, we dive into the sales of their retail fuel business and the motivation behind it. Lastly, we discuss what is next for the Wilson family as they chart a new direction.