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/

In the true spirit of The Unlimited Podcast, this episode in our “lessons with legends” series focuses on the importance of investing in your passions with Canadian entrepreneur, Miles Nadal. Brian and Miles discuss his journey of success, Warren Buffett’s investing secret, and his biggest life lessons.

Miles is a Canadian-born entrepreneur, philanthropist, and world-renowned collector whose inspiring journey began with humble roots in Toronto. He is the founder of Peerage Capital, a leading North American private investment firm with a diverse portfolio spanning real estate, wealth management, and self-storage. Peerage Capital’s affiliated brands include prestigious names like Sotheby’s International Realty Canada, Century 21, Chestnut Park, Echelon Wealth Partners, and Ourboro, among others.

Beyond his success in business, Miles is known for living life with passion and purpose. His famous “Dare to Dream” collection—featuring rare and exotic cars, along with one of the world’s most impressive sneaker collections—was recently auctioned for charity, reflecting his deep commitment to giving back.

A dedicated philanthropist, Miles has made transformational contributions to countless institutions in education, healthcare, and community development. His achievements have earned him accolades including Canada’s Top 40 Under 40 and Ernst & Young’s Entrepreneur of the Year Award, along with many others.

One message consistently emerges in any research on Miles Nadal: “Invest in Passion.” It’s a guiding principle he brings to every aspect of his life—from business ventures to personal pursuits and philanthropic impact.

Timestamps

0:00 Disclaimer & Intro

3:44 Miles' upbringing in Toronto

8:11 Seeing opportunity at an early age

10:02 Taking a start up to a public company

15:05 What is Peerage?

27:22 Principles of finding partners

30:55 The Dare to Dream collection

38:12 Miles' lessons from great people

43:01 Miles' thoughts on Trump's tariffs

48:23 How is Miles using AI?

50:55 What advice would Miles give to his younger self?

56:41 Outro

Two years after his first appearance on The Unlimited Podcast, Jordan Jacobs, Managing Partner & Co-Founder of Radical Ventures, is back to discuss how AI has evolved, and how it will change the future.

Brian and Jordan discuss "agentic" AI and its implications, the impact AI is having and will continue to have on jobs, AI regulation around the world, Jordan's favourite AI tools, and more!

This episode is a "must-listen" for those looking to understand how far AI has come, what lies ahead, and how to navigate the opportunities and risks of this transformative technology.

Plus stick around to the very end to hear "real" Brian speak with "AI" Brian about this episode.

Radical Ventures is a global AI-focused venture capital firm investing exclusively in artificial intelligence, with a presence in Toronto, San Francisco, and London and a mission to back founders building transformative AI companies. Radical's portfolio features category-defining AI leaders such as Cohere, Waabi, Untether AI, and Xanadu. Founders also gain hands-on help from Radical’s “Velocity” services team across recruiting, chip partnerships, go-to-market, policy, governance, and finance.

Jordan Jacobs is the Managing Partner and cofounder of Radical Ventures. He previously co-founded Layer 6 AI (acquired by TD Bank in 2018) and helped launch Toronto’s Vector Institute for Artificial Intelligence. He also serves on the board of the Canadian Institute for Advanced Research (CIFAR) and has helped shape Canada’s national AI strategy, bringing a policy lens to his work with founders. Jordan is also a member of the University of Waterloo President’s International Advisory Board, a Director of Tennis Canada, and has been selected as one of Toronto’s 50 Most Influential People.

Timestamps:

0:00 Episode 16 Recap

1:00 Intro & Disclaimer

4:06 What is AI?

6:30 How has AI evolved in the last 2 years?

11:20 What is Agentic AI

17:37 What does Agentic AI mean for jobs?

21:56 Government sentiment on AI

25:46 Jordan's message to the Minister of AI

37:25 Jordan's advice to businesses NOT using AI

43:35 Where is Radical investing?

51:41 What AI tools is Jordan using personally?

53:31 Outro

54:57 Ginsler.ai

From Brian Ginsler, Ginsler Wealth CEO:

"In mid-2018, while I was at a previous investment firm, I met with a prospective client. For context, the markets (S&P 500) had staged a dramatic recovery since the Global Financial Crisis. From its folkloric low of 666 in March 2009, the index had climbed to around 2,700 by mid-2018—an increase of more than 300%.

After I explained why it was a good time to invest with us, I will never forget his response: “I’m waiting until there is blood in the streets.”

I think about him often and wonder if he is...still waiting..."

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

On this episode of The Unlimited Podcast, Brian speaks with Michael Hyatt, one of Canada’s most successful tech entrepreneurs and now a leading investor and family office principal.

You may know Michael as the co-founder of BlueCat Networks, a global network infrastructure firm that was acquired by private equity in one of Canada’s most notable tech exits, a commentator on the CBC News, or as a former guest Dragon on CBC’s Dragon’s Den. Before BlueCat, Michael co-founded and sold Dyadem, an engineering software company. He is currently Executive Chairman of cybersecurity business Datastealth and also chairs the Hyatt Family Foundation, where they focus on supporting many causes around girls' and women's health, education, and underprivileged communities. But as you’ll hear in this conversation, Michael’s story extends far beyond his startup wins.

Brian and Michael dive deep into entrepreneurial resilience, how to scale and exit a company, and the evolution from founder to investor. Michael shares hard-won insights from building not one but two highly successful tech companies, his philosophy on hiring, and why letting go as a founder is often the smartest move you can make. They also explore how he built the Hyatt Family Office, the disciplines behind capital deployment, and his role as Senior Advisor at Northleaf Capital Partners.

The discussion takes a sharp and candid turn into Canadian policy and innovation, where Michael pulls no punches on what’s holding the country back—and what leaders like Mark Carney must do to turn it around. Plus: as the first episode in a series focused on AI, Michael provides his thoughts on the future of AI, what he’s seeing as a Fellow at the Creative Destruction Lab, and how he's using AI tools today to vet investments and manage complexity at scale.

Michael Hyatt is a tech entrepreneur, investor, and advisor. He co-founded BlueCat Networks (acquired by Madison Dearborn Partners) and Dyadem (acquired by IHS, now part of S&P Global). He is currently Executive Chairman of cybersecurity business Datastealth, leads the Hyatt Family Office, serves as Senior Advisor to Northleaf Capital, and mentors science-based startups through the Creative Destruction Lab. Michael has been named one of Canada’s Top 40 Under 40, has appeared on Dragon’s Den and The Pitch, and is widely regarded as a leading voice on business growth, innovation, and capital allocation in Canada.

Timestamps:

0:00 Disclaimer & Intro

5:32 Michael's entrepreneurial beginnings

11:57 Bringing in new leadership & building tech companies

21:25 Working with family

25:00 Michael's views on investing

30:45 How does bitcoin fit into Michael's portfolio?

35:02 Canada as a business environment

42:27 The creative destruction lab & AI

51:51 Michael's time on Dragon's Den

53:43 How is Michael using AI?

56:46 Outro