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May 22, 2025 66 mins

What happens when a Bay Street dealmaker trades spreadsheets for seed rounds—and turns Canada’s next wave of startups into a global force?


Alex Norman, co-founder of N49P and Canadian partner of TechTO, went from investment banking and private equity to becoming one of the country’s most connected early-stage investors and ecosystem builders. Through N49P, he’s backing founders who are flipping the script on what Canadian innovation looks like—scaling globally from day one, with grit, ambition, and world-class execution.


In this episode, we explore Alex’s transition from finance to founder whisperer, the strategic gaps he sees in Canada’s startup support system, and why being “nice” isn’t enough to build breakout companies.


Key themes we cover:

🔹 What Canadian founders can learn from Silicon Valley—without moving there

🔹 How to identify signals of conviction and coachability in early-stage teams

🔹 The difference between product obsession and market delusion

🔹 Why geographic humility is a superpower in global market expansion

🔹 Lessons from building a founder community that actually pays off


From crunching numbers in corner offices to catalyzing startups on café napkins, Alex’s journey proves that the sharpest instincts sometimes emerge when you trade the suit for the hoodie.


Chapters:

Welcome & Alex Norman Introduction (00:01 – 01:20)

From Bay Street to Startups: Alex’s Career Shift (01:21 – 06:10)

The Origin of N49P and Its Mission (06:11 – 11:00)

Why Canada Needed a Different Kind of Investor (11:01 – 16:35)

The Gaps in Canada's Startup Ecosystem (16:36 – 22:10)

What Makes a Founding Team Stand Out (22:11 – 27:50)

Lessons from TechTO and Building Founder Communities (27:51 – 33:40)

Going Global: Why Canadian Startups Should Think Bigger (33:41 – 39:25)

The Role of Coachability and Conviction in Founders (39:26 – 45:05)

How Alex Evaluates Startups and Markets (45:06 – 50:40)

What Founders Get Wrong About Pitching and Scaling (50:41 – 57:15)

Final Thoughts and Advice for Canadian Founders (57:16 – 01:06:58)


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