My cousin Colin Michael MacDonald is the COO of his family business, Micco Group of Companies. Much like my family business, they are invested in private businesses, real estate and marketable securities. Today we debate the pros and cons of our two distinct approaches to an investment company. Micco is much more hands on with their operations, whereas my business uses distributed leadership.

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Chris Ritchie is the former President of SilverCrest, a mining firm that sold for $2.5B CAD in 2024. In today’s episode, we discuss the fundamentals of the precious metals market. Chris explains the major differences between investing in a mining business and precious metals. He shares tips on how to buy gold or silver. Lastly, we discuss the outlook for precious metals given the recent market correction.

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In this episode, I provide a clear, plain-English summary of J.P. Morgan’s 2026 Outlook—“Promise and Pressure.” We walk through the major themes shaping markets, including AI’s investment boom, global fragmentation, and a shifting inflation regime. Along the way, I add my own commentary throughout from a family office perspective, focusing on what these trends could mean in real-world decision-making. This conversation is for educational purposes only and reflects my personal views. It is not investment advice, and nothing discussed should be considered a recommendation to buy or sell any security.

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What does it really take for the next generation to find their own voice in a family business?

In this episode, I speak with Danielle Saputo, third generation of the Saputo family and author of I Am Enough, about identity, expectations, and engagement across generations. We discuss why some next-gen family members choose a different path, how families can better support those decisions, and the lessons Danielle has learned as an advisor, mother, and sister working with family enterprises.

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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.