David Kassie is a legend on Bay Street. From building CIBC World Markets into a dominant force, to founding Genuity and transforming it into Canaccord Genuity, his fingerprints are on some of the most influential deals and institutions in Canadian finance. But in this episode of In the Money with Amber Kanwar, Kassie goes beyond the deals to talk candidly about the state of Canada’s capital markets and what needs to change.

This wide-ranging conversation covers everything from the art of the deal and what really drives great negotiation, to why Canada’s funding system is failing entrepreneurs and independent companies. Kassie shares stories from the early days of Genuity, including a billion-dollar build from zero and tells an insider story about how he knew Lehman Brothers was heading for collapse. He also explains why he believes the rise of private credit could be the next financial accident waiting to happen.

We dive into why Canada’s banking consolidation is choking liquidity, why independent dealers are disappearing, and how regulatory inaction has hurt innovation. He’s breaking new ground with his latest venture, Outcome Metric Asset Management, where the firm’s Canadian Equity Income Fund has earned the #1 Morningstar ranking in its category—out of several hundred funds—on a year-to-date basis over the past 12 months.

 Kassie pulls from decades of experience in investment banking, merchant banking, and startup investing to share hard-earned lessons on culture, strategy, and the difference between winning fast and winning smart.

If you care about Bay Street, capital markets, private credit, or the future of innovation in Canada, this is a must-watch conversation with one of the most seasoned voices in Canadian finance.

Timestamps
00:00 Show intro
02:30 How David Kassie became one of Canada’s most legendary deal makers
04:50 What drives his entrepreneurial spirit? 

07:15 The art of David Kassie’s deal
11:00 Break
11:40 What was David’s biggest win? The story behind Genuity
15:25 What was it like during the 2008 financial crisis?
17:00 The big problems with Canada’s funding environment
22:50 Break
23:20 How do you fight for space in the market?
25:30 There is not enough capital in Canadian markets to support entrepreneurs
27:30 What David has learned from his biggest mistakes
31:30 How David knew the financial crisis was coming (hint: it involves Lehman Brothers)
40:00 Why David thinks the next crisis could involve private credit
43:05 David’s new fund at Outcome Metric Asset Management and why he’s so proud of it
45:45 David’s view on what’s best for Canada’s future 

Sponsors

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DISCLAIMERS 

The information provided in this podcast is for informational purposes only and does not constitute financial, investment, or professional advice.The views expressed by the host and guests are their own and do not necessarily reflect the opinions of any organization or company. The host and guests may maintain positions in any securities discussed on the podcast. Always consult with a qualified financial advisor or professional before making any investment decisions.

In the Money delivers expert stock picks, actionable ideas, and timely money management tips. Hosted by business journalist Amber Kanwar, each episode features interviews with top portfolio managers who suggest ways to achieve good returns. Covering everything from ETFs and Canadian stocks to global investing trends, dividend strategies, and risk management, this show is made for DIY investors, stock market enthusiasts, and anyone looking to sharpen their financial strategy.

Contact: questions@inthemoneypod.com

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