In this episode, Lee Bragg, Vice Chair of Eastlink and member of the Bragg Business Family, shares how a Nova Scotian family business grew from its rural roots into a diversified enterprise spanning telecom, frozen foods, and airport services. Lee explains the group’s disciplined approach to risk, return, and diversification—and why capital allocation, not just entrepreneurship, sits at the heart of their long-term success. He also discusses why the Braggs prioritize meritocracy over nepotism, and how strong governance and clear expectations help protect both the family and the business across generations.

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Ben Hertzman is the 2nd Gen President of Progress Luv2Pak and Gather Packaging. They specialise in premium retail packaging for customers across North America. We discuss Ben’s offshore supply chain and how he has become an expert in navigating tariffs. He also shares how his team has recently reshored part of their manufacturing to Toronto. We discuss the ingredients that have made his succession work for him and his father. As well, we delve into the history of his family business and how his Dad’s first big break was producing the boxes for Trivial Pursuit in the 1980s.

Pierre Somers is the founder of Montreal-based Walter Group and the third generation of his entrepreneurial family. Their story begins in Germany in the early 1900s with the building of locomotives. We delve into the complex journey of his family and how they had to reinvent themselves many times. We discuss the Walter Group’s investment strategy and how Pierre has attracted top talent. Lastly, we discuss his children and their unique paths.

Derrick Hunter is the 2nd-generation CEO of Calgary-based Bluesky Equities. In this episode, we discuss how Derrick pivoted his family business from a concentrated to a diversified model. Starting in the Alberta oil patch, the business has now become a diversified portfolio of alternative investments, including private equity and venture capital.

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.

Adrian Rocca is the CEO and founder of Fitzrovia. In this interview, he shares how being fired from Tricon set him on a path to build Canada’s largest purpose built rental business. Adrian delves into the latest innovations of his portfolio and how to develop affordable housing in Canada.