Joseph Schaefer arrived in Canada from Poland in the 1930s and built his career in Montreal’s garment district at a time when the industry ran on instinct, relationships, and trust. He had an eye for fashion, a gift for reading people, and a way of doing business that set him apart early.
In this episode of Big Shot, Joseph joins hosts Harley and David to reflect on how he found his way into the garment trade and helped shape what Chabanel would become. He shares how he built partnerships that lasted decades, why he never lost a partner, and how he gave others ownership long before equity was common practice.
This is a story about a different era of entrepreneurship—one where deals were built on reputation, capital came through relationships, and success depended on understanding both the product and the people behind it. Joseph also reflects on what’s changed, why that kind of success is harder to replicate today, and the role his values and faith played in how he built his life and business.
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In This Episode We Cover:
(00:00) Intro
(01:06) Early days after immigrating to Canada
(03:10) How Joseph got his start in entrepreneurship
(07:38) Learning the craft with help from his sister
(09:55) When he brought on salespeople
(11:27) How he built Chabanel
(14:20) Joseph’s approach to capital and equity
(18:16) How Joseph won over banks
(22:24) Why Joseph’s success wouldn’t be repeatable in today’s market
(25:45) How Joseph managed partnerships
(29:00) Joseph’s legacy
(31:52) Joseph’s advice for young entrepreneurs
(32:50) His relationship with the Bronfmans
(35:20) The role of faith in his life
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Where To Find Big Shot:
• Website: https://www.bigshot.show/
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• Harley Finkelstein: https://twitter.com/harleyf
• David Segal: https://twitter.com/tea_maverick
• Production and Marketing: https://penname.co
