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Podcast · 10 episodes

Big Shot

by Big Shot · English

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.

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How a 17-Year-Old From Tehran Turned $750 Into a Toy Empire | Isaac LarianIsaac Larian’s rise from a bullied Jewish boy in Tehran to building major toy and electronics brands, including Nintendo handhelds and MGA Entertainment’s Bratz and LOL Surprise.25 Jun 2026 · 1 h 22 min · 33 chapters
The Coney Island Kid Who Made Rocky, Goodfellas, and Raging Bull | Irwin WinklerIrwin Winkler’s rise from Coney Island hustler to Hollywood “invisible architect,” detailing how he helped greenlight and produce major films (Rocky, Goodfellas, Raging Bull, The Wolf of Wall Street)…11 Jun 2026 · 1 h 18 min · 37 chapters
From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After AnotherBarry Diller’s career arc from Paramount to Fox to IAC/Expedia, emphasizing serendipity, “walking through doors,” and building scalable media formats (ABC Movie of the Week, miniseries) without a…21 May 2026 · 49 min · 21 chapters
The Quiet Dealmaker Who Bought the Warriors and A’s | Lew WolffLew Wolff (Lou Wolf) discusses his “quiet” approach to entrepreneurship and sports ownership—tempered ambition, partnership, and not being attached to outcomes—while recounting how he became a…30 Apr 2026 · 1 h 21 min · 36 chapters
The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph SchafferJoseph Schaffer, a 104-year-old Montreal garment-industry entrepreneur, recounts building Chabanel’s “shmatta” ecosystem, starting with $1,800 and turning it into massive wealth, while arguing for…9 Apr 2026 · 37 min · 20 chapters
Disney Fired Him. He Built DreamWorks, Shrek, and a $3.8B Empire | Jeffrey KatzenbergIn this episode titled "Disney Fired Him. He Built DreamWorks, Shrek, and a $3.8B Empire", Harley Finkelstein and David Segal interview Jeffrey Katzenberg, a prominent figure in Hollywood known for…19 Mar 2026 · 1 h 14 min · 29 chapters
Goldman Sachs Rejected Him. Years Later, He Ran the Place | Lloyd BlankfeinHarley Finkelstein and David Segal25 Dec 2025 · 1 h 49 min
She Escaped Communism, Reinvented Nail Polish, and Sold for a Billion DollarsHarley Finkelstein and David Segal11 Dec 2025 · 1 h 23 min
How a Blue-Collar Kid Built the Most Powerful Agency in Hollywood | Michael OvitzIn this episode of Big Shot, hosts Harley Finkelstein and David Segal interview Michael Ovitz, the legendary founder of the Creative Artists Agency (CAA) who redefined the landscape of Hollywood and…11 Nov 2025 · 1 h 23 min
Borrowed Ten Grand, Turned Down Ten Billion | Stephen RossSteve Ross, founder of Related Companies, recounts how he built a real-estate empire by combining government-subsidized affordable housing with tax-shelter financing, then scaling into mixed-use…17 Jul 2025 · 1 h 42 min · 38 chapters