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 For over 25 years, Raymond James has been helping Canadians achieve their financial goals. Visit raymondjames.ca today to discover how you can live a life well planned. With $62 billion in assets, ATB Financial is powering possibilities for more than 820,000 financial services clients in Alberta and beyond. Visit ATB.com/inthemoney for more information Over the last 45 years, Middlefield has helped Canadians build and preserve wealth through active management. Ask your financial advisor about Middlefield or learn more at middlefield.com today. Discover how The Murray Wealth Group can work for you by visiting MurrayWealthGroup.com . World Class Investing. Wealth built together. Links https://inthemoneypod.com/ https://instagram.com/inthemoneypod https://facebook.com/profile.php?id=61569721774740 https://twitter.com/inthemoneypod https://tiktok.com/@inthemoneypod
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