
Big Shot
If the walls of Kosher delis could speak, they would (schm)ooze invaluable wisdom and endless laughs. Harley Finkelstein (Shopify) and David Segal (DAVIDsTEA) are Jewish entrepreneurs influenced by the greats who came before them. But, they realized no one was archiving the best behind-the-scenes stories ever told. Before time was up, they set out on a passion project to preserve the memories, mishaps, and wins of the people who have seen it all. Big Shot tells the stories of the people that shaped an entire generation.
Latest episodes

Aug 31, 2023 • 24min
Legacy Lessons: The Enduring Wisdom of Our Grandparents for Success Today
In today’s episode, we explore stories from our guests on how their parents and the previous generation profoundly impacted their lives. You’ll hear from Ed Sonshine, Jonathan Wener, Issy Sharp, Charles Bronfman, and Aldo Bensadoun about how they learned their relentless work ethic from their parents and the power of learning by example. It’s a great example of how each generation stands on the shoulders of the giants that came before them.
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In This Episode, We Cover:
(00:00) Welcome to Big Shot Shorts
(00:58) The power of the past generation
(04:22) Ed Sonshine on the two things his father taught him
(07:49) How Jonathan Wener learned his work ethic
(10:37) Issy Sharp on learning by example
(16:15) Charles Bronfman on learning to give back
(20:04) Aldo Bensadoun on treating others with love, respect, and integrity
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Where To Find Big Shot:
Website: https://www.bigshot.show/
YouTube: https://www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
Instagram: https://www.instagram.com/bigshotshow/
Harley Finkelstein: https://twitter.com/harleyf
David Segal: https://twitter.com/tea_maverick
Production and Marketing: https://penname.co

Aug 17, 2023 • 26min
How To Live A Rich Life Through Giving Back
Issy Sharp, founder of Four Seasons, discusses raising $1 billion for the Terry Fox Run. Jonathan Wener believes the best way to live a rich life is by giving back. They explore the importance of giving to the next generation and why we are put in this world to make it better. Topics include philanthropy, tikun olam, and the impact of the Terry Fox Run.

Aug 3, 2023 • 26min
Winning Big with Chutzpah: Lessons from the Titans of Entrepreneurship
Looking for a masterclass on taking chances and winning big? This episode of Big Shot looks at the one trait shared by all the successful entrepreneurs and billionaires on the podcast -- chutzpah. It's one thing to say you can't fear failure. And it's something completely different to act in ways that seem crazy at the moment but turn out to be the perfect move. This episode shares the combined wisdom of Ed Sonshine, Charles Bronfman, Aldo Bensadoun, Jonathan Wener, Issy Sharp, and hosts Harley Finkelstein and David Segal. You'll learn how the best entrepreneurs approach risk differently than the rest, and that's a big reason why they succeed in ways others can't imagine.
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In This Episode, We Cover:
(00:00) Wow, what a first season of Big Shot
(04:02) Pitching Season 2
(05:15) Ed Sonshine on what chutzpah means to him
(06:19) Charles Bronfman on chutzpah
(07:05) Aldo Bensadoun shares his take
(12:02) Jonathan Wener on not taking no for an answer
(17:33) Issy Sharp on giving your best
(20:57) Harley and David on what chutzpah means to them
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Where To Find Big Shot:
Website: https://www.bigshot.show/
YouTube: https://www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
Instagram: https://www.instagram.com/bigshotshow/
Harley Finkelstein: https://twitter.com/harleyf
David Segal: https://twitter.com/tea_maverick
Production and Marketing: https://penname.co

14 snips
Jun 29, 2023 • 1h 1min
An Unfiltered Conversation With The Founder of The Four Seasons: Issy Sharp (Part 2)
In this episode, Issy Sharp, founder of The Four Seasons Hotels and Resorts, reveals how McDonald's influenced their approach to hospitality, why they don't own any real estate, and how the death of his son inspired him to support the Terry Fox run. He also shares a surprising bomb at the end. They discuss the power of service and attitude, the importance of work-life harmony, and their philanthropic efforts. They emphasize belief in oneself and the influence of their Jewish heritage on their 'can do' attitude.

18 snips
Jun 15, 2023 • 1h 3min
How Issy Sharp Built The Four Seasons and Transformed The Hospitality Industry Forever (Part 1)
"Big Shot" welcomes Isadore (Issy) Sharp, the founder of The Four Seasons. In this episode, Issy shares his incredible journey, from growing up in construction to meeting his wife over 70 years ago. Learn about the concepts that made The Four Seasons successful, his fearlessness, and the best investment of all time.

8 snips
May 25, 2023 • 1h 7min
Ed Sonshine: From Displaced Persons Camp To a Multi-Billion Dollar Real Estate Empire
Ed Sonshine is one of those people you could speak with for hours and barely scratch the surface of his life. Born in Bergen-Belsen Displaced Persons Camp after World War II to two Holocaust survivors, he immigrated to Canada as a young child. After already becoming a very successful lawyer, he founded RioCan, which, at the time, was the first REIT (Real Estate Investment Trust) in Canada. As of this recording, RioCan operates 193 properties, has over 33 million in leasable square feet, and an evaluation of $15 billion. In this episode of Big Shot, you’ll learn what it was like being born in Germany after the war, how Ed built a real estate empire while still being a family man, why he thinks the Jewish community is extremely self-reliant, and much more.
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Where To Find Big Shot:
Website: bigshot.show
YouTube: https://www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
Instagram: https://www.instagram.com/bigshotshow/
Harley Finkelstein: https://twitter.com/harleyf
David Segal: https://twitter.com/tea_maverick
Production and Marketing: https://penname.co
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In This Episode, We Cover:
(00:00) Welcome to Big Shot and meet our guest Ed Sunshine
(05:40) The early days of Ed’s life and being born in a displaced person’s camp
(10:18) Why Ed’s father was a smuggler after the war and never complained
(14:55) What made Ed want to be successful and change career paths
(19:12) When Ed got the idea to bring the first REIT to Canada
(24:38) What he learned from his father that had a profound impact on him
(27:20) How Ed built a business empire while being a family man
(31:20) Why Ed finally got a cottage
(36:40) How Ed defines success, financial security, and purpose
(42:15) Why the Jewish community is self-reliant
(50:51) How Ed defines chutzpah
(52:32) A story you need to hear about Ed’s father
(58:36) What worries Ed about the future
(1:04:40) Ed’s biggest piece of advice to younger generations
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Referenced:
RioCan: https://www.riocan.com/
Bergen-Belsen Displaced Persons Camp: https://encyclopedia.ushmm.org/content/en/article/bergen-belsen-displaced-persons-camp
An Empire Of Their Own: How the Jews Invented Hollywood: https://www.amazon.com/Empire-Their-Own-Invented-Hollywood/dp/0385265573

Apr 27, 2023 • 59min
The Power Of Kindness: How Jonathan Wener Turned A $10k Loan Into A $15 Billion Empire
Jonathan Wener shares how he turned a $10k loan into a $15 billion empire by prioritizing kindness, integrity, and hard work. He reveals stories of bold decisions, building strong relationships, and the importance of giving back. Learn how his journey from laborer to millionaire shaped his remarkable success in real estate.

16 snips
Apr 13, 2023 • 46min
Building A Billion-Dollar Shoe Brand From Scratch: Aldo Bensadoun
Aldo Bensadoun shares his inspiring journey of building a successful shoe brand, emphasizing the importance of kindness and making decisions based on values. Exploring entrepreneurship by necessity and their initial reservations about retail. How Aldo sold encyclopedias door-to-door. The unexpected journey into the shoe business and their departure from a shoe company due to a disagreement with their boss. Building Skechers and embracing integrity. Cause marketing and the power of Jewish entrepreneurs.

Mar 30, 2023 • 29min
The Man Who Brought Baseball to Canada and Founded Birthright: Charles Bronfman
Some entrepreneurs don't just build businesses, they take bold risks that can shape a country or revitalize a religion. That's Charles Bronfman. On the first episode of Big Shot, hosted by Harley Finkelstein and David Segal, you'll learn about Bronfman’s incredible upbringing, lessons, and experiences that inspired many transformational initiatives. From watching his father build Seagram’s to bringing the Expos to Canada and founding Birthright Israel. Bronfman left a legacy in business, charity, and family with endless lessons for all.
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Where To Find Big Shot:
Website: bigshot.show
YouTube: https://www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
Instagram: https://www.instagram.com/bigshotshow/
Harley Finkelstein: https://twitter.com/harleyf
David Segal: https://twitter.com/tea_maverick
Production and Marketing: https://penname.co/
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In This Episode, We Cover:
(00:00) Welcome to Big Shot. More about our first guest
(02:15) The catalyst behind Big Shot
(04:05) What is the meaning of chutzpah
(05:38) How Charles brought Major League Baseball to Canada
(10:02) The story of Charles telling his father, Sam, about bringing baseball to Canada
(15:00) The incredible story of building Birthright Israel
(20:18) What makes Jews so unique when it comes to business and entrepreneurship
(26:31) Charles Bronfman’s three biggest things to consider in your life
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Referenced:
Distilled: Distilled A Memoir of Family, Seagram, Baseball, and Philanthropy: https://www.amazon.com/Distilled-Memoir-Seagram-Baseball-Philanthropy/dp/144345396X
Sam Bronfman: https://en.wikipedia.org/wiki/Samuel_Bronfman
Birthright Israel: https://www.birthrightisrael.com/
Seagram’s: https://www.seagramsescapes.com/

Mar 22, 2023 • 2min
Welcome to Big Shot
Many of the greatest stories of entrepreneurship have never been told. It’s time to change that. Big Shot is an archive and celebration of Jewish entrepreneurs who took risks, overcame the odds, and created legendary businesses that changed the game. Each episode documents the memories, culture, hardship, and chutzpah it takes to become a big shot.
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Where To Find Big Shot
Website: bigshot.show
YouTube: https:/www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
Instagram: https://www.instagram.com/bigshotshow/
Harley Finkelstein: https://twitter.com/harleyf
David Segal: https://twitter.com/tea_maverick
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Production and marketing by https://penname.co/
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