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 or go to Ginsler Wealth's YouTube channel: https://www.youtube.com/@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.

If you want to learn how to invest, this episode of the Unlimited Podcast isn’t for you. Brian sits down with renowned investor Barry Ritholtz to talk about his new book How Not to Invest. They explore Barry’s irreverent communication style, the creation of Ritholtz Wealth Management, his belief that “nobody knows anything,” and much more.

Barry Ritholtz is one of the most influential voices in modern finance known for blending behavioural insight with data-driven analysis. As co-founder, chairman, and CIO of Ritholtz Wealth Management (founded in 2013), he oversees a multibillion-dollar advisory firm built on transparency, fiduciary duty, and client alignment.

He’s also a celebrated writer and media figure. Barry created the award-winning blog The Big Picture (founded in 1998, relaunched on TypePad in 2003), which has drawn tens of millions of readers and remains one of the most respected financial blogs online. His commentary has appeared in Bloomberg Opinion, The Washington Post, and across major financial media outlets, including Bloomberg Television.

Barry authored the bestseller Bailout Nation (2009), a sharp critique of the 2008 financial crisis, and his latest book How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth and How to Avoid Them (March 2025) continues his mission to help investors avoid costly mistakes.

He also hosts Bloomberg Radio’s Masters in Business podcast, featuring long-form interviews with leading investors, economists, and business thinkers.

Barry holds a B.A. in Political Science (with a Philosophy minor) from Stony Brook University and a J.D. (cum laude) from Benjamin N. Cardozo School of Law. He lives on Long Island, New York, with his wife and two dogs.

Timestamps

0:00 Disclaimer & Intro

7:11 What inspired Barry's career?

11:01 Barry's "Day Job" at Ritholtz Wealth Management

15:22 Humour & Professionalism

19:12 What inspired How NOT to Invest?

23:19 Learning from the two Charlies

30:50 Nobody knows anything

38:06 What might investors be blind to?

42:40 The power of saying "I don't know"

48:01 If Barry could do anything, what would it be?

50:17 Outro

From Brian Ginsler, Ginsler Wealth CEO:

"No, this letter won’t focus on the Coldplay “affair” controversy that was all over social media this summer. But I did attend the Coldplay concert in Toronto with my actual wife, and I have pictures to prove it.

In addition to putting on a fantastic show, Coldplay's lead singer, Chris Martin, showed me just how he does his job each night, which got me thinking about how we do our job for our clients."

Listen to this episode to find out...

For the original transcript of this letter and to see weblinks and other media, please visit https://ginslerwealth.com/ginsler-wealth-third-quarter-2025-client-letter-the-coldplay-edition/