

Big Shot
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.
Episodes
Mentioned books

Nov 30, 2023 • 32min
Jewish Titans and Untold Triumphs: Predicting the 2008 Crash, The Architect of Canadian Pride, and More Hidden Stories You've Never Heard!
When you sit down with iconic entrepreneurs for two to three hours, it's hard to include every story in an episode. But that doesn't mean every story isn't worth telling. On this episode of Big Shot shorts, you'll hear some wild tales that didn't make it into individual episodes of season 1. You'll learn how Ed Sonshine anticipated the 2008 crash, what Aldo Bensadoun did to break into America when so many others failed, how Charles Bronfman shaped Canadian pride, and Jonathan Wener's wild story about acquiring a massive art collection. These are the stories that, once you hear them, you'll want to retell to others.
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In This Episode, We Cover:
(00:20) Harley and David have an epiphany about their Canadian upbringing
(01:50) Every Canadian retailer fails, except for one
(02:10) Why this bonus episode was necessary
(03:10) Jonathan Wener's family collection of 140 paintings
(05:55) How Ed Sonshine anticipated the 2008 housing crash
(10:00) How passing up on a round of golf was one of Ed Sonshine's best decisions
(17:45) How Charles Bronfman was behind Drake's start
(18:30) Why Charles Bronfman created Heritage Minutes
(22:25) How Aldo Bensadoun succeed in America when so many others failed
(28:25)The only lawsuit Jonathan Wener faced in 52 years
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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

Nov 2, 2023 • 29min
Why Billionaires Believe Work-Life Balance Is A Myth
One of the hardest parts of being an entrepreneur is the stress and anxiety of never having enough time. When ambition flows through your veins, it’s difficult to balance your desire to build something great with your love for your family, friends, and other interests. Being an entrepreneur requires sacrifice — but how do you do that without giving up what matters most? On this episode of Big Shot Shorts, Issy Sharp, Charles Bronfman, and Ed Sonshine reveal their regrets, rules, and recommendations for creating happiness and harmony in work and life.
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In This Episode, We Cover:
(01:00) Work-life balance is not a 50-50 equation
(02:00) Why entrepreneurs struggle so much with finding time for everything
(02:48) How consistency can help reduce stress and anxiety
(03:30) David Segal’s family ritual
(06:00) The most important source of support for entrepreneurs
(08:00) Issy Sharp’s lessons from decades of a happy marriage
(09:25) Issy Sharp’s regrets about building the Four Seasons
(13:05) Charles Bronfman’s lessons on raising a family with ambition and purpose
(19:00) Why it’s important to “never look back”
(22:00) Ed Sonshine’s 3 rules for family happiness
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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

Oct 19, 2023 • 21min
Why Jews Are Entrepreneurs By Necessity
Did you know that less than .2 percent of the world is Jewish? And yet, more than 20 percent of all Noble Prize winners are Jewish. What explains the high likelihood of success? On this episode of Big Shot shorts, Harley Finkelstein and David Segal explore the history of Jewish entrepreneurship with legends Charles Bronfman, Aldo Bensadoun, and Ed Sonshine. Their competitive advantage? They had everything to lose, giving them no choice but to find a way to win.
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In This Episode, We Cover:
(00:25) The tidal wave analogy
(03:30) Why are so many Jews successful?
(05:15) Entrepreneurs by necessity
(06:55) The curious relationship between anti-semitism and Jewish entrepreneurship
(10:00) The surprisingly small number of Jews in the world
(11:35) The Jewish career path
(16:50) Why Ed Sonshine is worried for future entrepreneurs
(18:40) It’s tough to make diamonds without pressure
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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

Sep 28, 2023 • 26min
Integrity Is More Than A Principle -- It's The Secret To Entrepreneurial Success
Some of the best stories in business are the ones you never hear about. They are the deals that fell through, the partnerships that never happened, and the employees who didn’t make it. Behind those moments are decisions that shape some of the best businesses. And, when you speak with some of the world’s greatest entrepreneurs, you realize that those moments are shaped by strong values. In particular, the best entrepreneurs lean into integrity to turn risks into rewards. On this episode of Big Shot Shorts, you’ll learn how Jonathan Wener, Aldo Bensadoun, and Issy Sharp all took the hard road by trusting in integrity, doing the right thing, and making life-changing decisions that defined their businesses and led to undeniable success.
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In This Episode, We Cover:
(00:00) The variable not discussed enough in business
(01:35) A crazy story about Starbucks and Spotify
(04:35) Why Jonathan Wener left $10 million on the table
(07:20) How to build great relationships and develop trust
(11:45) “You’re going to outgrow us before we outgrow you.”
(12:40) How Aldo’s billion-dollar business was born out of integrity
(14:15) It’s possible to be a capitalist and be fair
(16:20) The Four Seasons’s “sustainable competitive advantage”
(19:30) How McDonald’s influenced the Four Seasons
(24:40) Instilling a winning culture at all costs
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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

Sep 14, 2023 • 22min
How Business Legends Build The Best Teams
Learn how successful entrepreneurs build world-class teams, emphasizing the value of good partners and helping employees reach their full potential. Topics include partnership formulas, the importance of chemistry, making the first hire, building a brand, employee perks, integrity in hiring, making employees wealthy, and building a culture.

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.


