E62: Role Reversal: Ira Gluskin Interviews Brian Ginsler

In a special role-reversal episode of The Unlimited Podcast, legendary Canadian investor Ira Gluskin returns—this time as interviewer. Ira (co-founder and former CIO of Gluskin Sheff) sits down with Brian Ginsler to unpack Brian’s personal path through investment banking and family office work, the lessons that shaped Ginsler Wealth, and why a truly holistic “personal CFO” model matters for successful families.

Full VIDEO of this podcast can also be found here (   • Role Reversal: Ira Gluskin Interviews Bria...  ) or go to Ginsler Wealth's YouTube channel:    / @ginslerwealth  

Brian explains how Ginsler Wealth seeks to deliver smoother long-term outcomes through deep diversification beyond traditional stocks and bonds, why aligning fees with clients is core to the firm’s philosophy, and how the family office service removes complexity from taxes, estate planning, cash-flow logistics, and life’s curveballs. Ira also pushes Brian on business building, pricing, and the future impact of AI—leading to a great behind-the-scenes look at how the firm operates and where it’s going.

If you’ve ever wondered what Ginsler Wealth really does, how a multi-family office differs from a traditional wealth manager, or why Brian built the firm the way he did, this is the episode.

Timestamps:
0:00 Disclaimer & intro
0:40 The twist: Ira interviews Brian
1:35 Why Brian avoids talking about himself (and why Ira insisted)
4:17 Brian’s early life in Toronto; schooling and career direction
5:04 Discovering finance at Ivey; first exposure to markets
5:56 First Marathon / National Bank investment banking years
6:29 Harvard Business School and early career reflections
7:10 Fintech summer role; deciding to return to Canada
8:30 Post-HBS job market; back to banking, then pivot to family office
9:25 What a multi-family office really is
12:10 Joining Gluskin Sheff; working with Ira, Gerry, and Jeremy
14:00 Becoming COO; leadership lessons from early responsibility
15:50 The limitations of captive “in-house product” models
17:11 Founding Ginsler Wealth: the origin story and mission
20:18 Building portfolios beyond stocks/bonds; multi-layer diversification
23:17 Defining volatility and why clients care more than theory suggests
27:12 The second business: the family office / “Personal CFO” model
29:00 How GW works alongside other managers
30:10 Fees: asset-based, performance elements, and retainers
32:19 Why GW avoids hourly billing (and what clients gain)
35:05 How the firm grows: referrals and professional networks
38:40 Family office value during life transitions and estate realities
43:10 Choosing mid-market specialists vs giant Bay Street firms
44:10 The rise of family offices in Canada
47:07 GW’s team structure: boutique, specialized, growing
48:03 AI in wealth management: what GW is doing today
49:47 Tangible AI example: will comparisons and risk reduction
51:20 Banks: custody, product selection, and logistics support
54:28 Marketing and why GW doesn’t advertise traditionally
56:43 Wrap-up and closing thoughts

If you like what you hear, please don’t hesitate to rate us kindly. And if there are particular topics you’d like covered, please let us know.