Dave Michaels served as editor at Canadian Family Offices from its launch in June 2021 to his retirement on June 30, 2026. Previously, he was an assigning editor for the Report on Business section at The Globe and Mail and an assistant features editor at The Arizona Republic in Phoenix.
How do you say goodbye to something you fed, nurtured and watched mature into an industry-leading publication?
Five years ago last week, Canadian Family Offices threw open its virtual doors and hoped readers would find their way in.
We started with 32 articles on the site. But we knew that would cover only a sliver of the vast financial world of Canada’s most wealthy people and their advisory offices, including such topics as investment, estate planning, philanthropy, family business and, of course, how family offices operate and serve their clients or owners.

Our goal was to become a must-read among people with millions (or billions) in wealth and their advisory staffs. But how do you come up with content that reflects and perhaps illuminates their worlds if you don’t exactly know what goes on in them? It’s not like you can search Google (though AI is doing better these days).
This is a challenging field to start a publication in. The family office business is pretty opaque, and rightly so. How could we learn more about this space?
The answer to that question led to one of the most rewarding parts of the job—the part that I will miss most as I retire from the position of Canadian Family Offices editor this week.
At the beginning, I wasn’t sure why FO executives would want to speak with us, given the level of privacy they must maintain. But they did, thank goodness. We did not speak about particular clients, of course, but they answered my questions about the sector, their pain points and what they loved about their jobs.
Chatting remotely with people in the industry (COVID-19 was still a thing) turned out to be a catalyst for me. I couldn’t have predicted how gracious and down-to-earth nearly everyone would be. And helpful! They saw that we wanted to be an industry bulletin board of sorts, a reflection of the business and a place for voices, ideas and news.
Dave’s five in five
To mark my departure from CFO—and to welcome Ashley Redmond to the role—my boss asked me to note some of the articles that stand out in my mind, even to this day.
Time to set fire to ‘shirtsleeves’ adage about family wealth, March 1, 2022, by Matthew Halliday: Among the most familiar truisms in the family office world is “shirtsleeves to shirtsleeves in three generations,” a pithy way of saying that what one generation builds, the next enjoys and the third squanders. But is it true? Being a newbie, I assumed it was. But you know what they say about assuming. Thank you to Carolyn Cole, of Cole & Associates, for setting me straight. And it made for a great article. I still see references to it today.
Wealth report: Old and new money flourish side-by-side in booming Quebec, May 18, 2022, by Anna Sharratt: This article noted that Quebec’s economy was on fire, and in a very good way. A surge in the tech sector was complementing the province’s classic economic engines of manufacturing, real estate and health care. Family offices found themselves serving two distinct groups. On one hand, advisors counselled the older generation about wealth and succession planning. On the other, they were educating young, newly wealthy tech entrepreneurs who wanted a more holistic approach to wealth management. It was one of the first times I thought we finally had our finger on the pulse of something.
Married into wealth: Reflections on a life made ‘easier, not necessarily happier’, Sept. 7, 2022, by Kerry Gold: As the chief marketing officer of a Toronto wealth management firm, Kelly Willis Green already knew a lot about money. But when she married a successful real estate developer about a decade ago, her role in the world of wealth stewardship became more personal. Today, she is known in the family office industry as a “married in,” someone who joins a wealthy family by marriage. And she didn’t mind talking about it and sharing with Canadian Family Offices readers (being introduced to her was a “pinch me” moment in journalism). We became friends, and today she is a wealth coach, speaker and podcaster who contributes articles to Canadian Family Offices. Thank you, Kelly.
The List: 81 multi-family offices in Canada, Nov. 26, 2023, compiled by Sarah B. Hood: When I started this job, I was amazed that there really were no lists of multi-family offices (or their cousins, single-family offices) in Canada. Why not? How difficult would it be to create one? Because our site was young, we didn’t want to step on toes and end up with firms asking to be removed, so we asked permission first. We also decided that if a firm called itself a family office, we would consider it a family office. Our list quickly became the most-clicked article on the site. But since then, we have faced one of the most controversial issues of this sector: What, indeed, is a family office? What is a multi-family office? Are all the firms on our list family offices? Probably not, depending on who is doing the defining.
It can be lonely at the top, say family office executives, Nov. 12, 2024, by Sarah B. Hood: The origins of this article came from a discussion with a family office executive. He said he loved his work, but that it was a pretty solitary job. He worked from home and had a very small staff. Because of the sensitive nature of his work, he couldn’t discuss it with anyone, and family office events were few and far between. A few months later, another executive brought up the same thing. Bingo, story.
At this point, I should thank a few people whom I call “CFO superfans,” who understood what we were doing and supported us and offered article ideas pretty much right from the start. Among them are Carolyn Cole, Kelly Willis Green, James Dunne, Eric Lapointe, Elke Rubach, Steve Legler, Danielle Saputo, Jim Grubman, Dan Riverso, Tina di Vito, Nancy Marshall, Ralph Awrey, Mark Barnicutt, Mindy Mayman, Barbara Stewart, Jeff Noble and Chris Foster. To them and the many others who have advised me, thanks to you all.
And so, I bid adieu, off to join other retirees puttering in the garden and looking forward to the next trip. It was lots of fun peeking into a world that will never divulge all of its secrets.
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