

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

12 snips
Jun 25, 2026 • 1h 22min
How a 17-Year-Old From Tehran Turned $750 Into a Toy Empire | Isaac Larian
Isaac Larian, founder and CEO of MGA Entertainment and creator of Bratz and L.O.L. Surprise!, recounts his journey from Tehran to building a toy empire. He discusses arriving in America with $753, pivoting from electronics to toys, the creation and risky launch of Bratz, and the long legal battle with a major rival. Tough beginnings, bold bets, and relentless persistence drive the conversation.

11 snips
Jun 11, 2026 • 1h 18min
The Coney Island Kid Who Made Rocky, Goodfellas, and Raging Bull | Irwin Winkler
Irwin Winkler, veteran Hollywood producer behind Rocky, Raging Bull, Goodfellas and more, shares stories from a six-decade film career. He recalls moving from the William Morris mailroom to producing, discovering Sylvester Stallone, reshooting Rocky’s ending, launching collaborations with Scorsese, and navigating financing, VFX, AI, and studio relationships.

May 21, 2026 • 49min
From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After Another
Barry Diller, longtime media executive who built Paramount, launched Fox, and led IAC, appears with a brisk mini bio. He recounts starting in a mailroom, learning from files, and the serendipity that shaped his rise. He discusses creating TV innovations, persuading Rupert Murdoch to back Fox, and strategic acquisitions like Expedia. He reflects on leadership, M&A instincts, and finding the right door when opportunity knocks.

Apr 30, 2026 • 1h 21min
The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff
Lew Wolff, longtime real estate developer and former owner of the A’s and Warriors, reflects on an accidental path into big projects and pro sports. He discusses reshaping downtown San Jose, partnering with studios and investors, the stories behind Moneyball and stadium fights, and his partnership-first philosophy. Short, reflective tales reveal how temperament and relationships guided his decisions.

10 snips
Apr 9, 2026 • 37min
The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph Schaffer
Joseph Schaefer, a Polish-born Canadian who built Montreal’s Algo dress business and helped shape Chabanel, reflects on starting with $1,800 and growing long-term partnerships. He discusses building manufacturing, winning bank trust, giving partners equity, and how scale and overseas production transformed the industry. He also touches on philanthropy, loyalty, and values that guided his career.

21 snips
Mar 19, 2026 • 1h 14min
Disney Fired Him. He Built DreamWorks, Shrek, and a $3.8B Empire | Jeffrey Katzenberg
Jeffrey Katzenberg, famed filmmaker who helped revive Disney animation and co-founded DreamWorks, shares tales from Hollywood. He talks about growing up with dyslexia, lessons from his father and Kirk Douglas, and the mindset of exceeding expectations. He recounts revitalizing Disney, being fired, building DreamWorks with Spielberg and Geffen, and the highs and lows of studio life.

12 snips
Dec 25, 2025 • 1h 49min
Goldman Sachs Rejected Him. Years Later, He Ran the Place | Lloyd Blankfein
Lloyd Blankfein, the former CEO and Chairman of Goldman Sachs, reflects on his unconventional rise from Brooklyn projects to the pinnacle of finance. He shares insights from his early days, including navigating the culture shock of Harvard at 16. Lloyd discusses pivotal moments, like his rejection from Goldman leading him to J. Aron, and the lessons learned during the 2008 financial collapse, highlighting how Warren Buffett's support shaped his leadership. His journey is a testament to resilience, decision-making, and the power of chance.

11 snips
Dec 11, 2025 • 1h 23min
She Escaped Communism, Reinvented Nail Polish, and Sold for a Billion Dollars
Suzi Weiss-Fischmann, co-founder of OPI and a transformative figure in the nail polish industry, shares her incredible journey from escaping communist Hungary to creating a billion-dollar brand. She discusses how her family's Holocaust legacy shaped her work ethic and values. The conversation explores the art of naming nail polishes, embracing competition, and the emotional connections formed through storytelling. Suzi reflects on the ups and downs of her business, including a major lipstick setback, and emphasizes the importance of community and resilience.

41 snips
Nov 11, 2025 • 1h 23min
How a Blue-Collar Kid Built the Most Powerful Agency in Hollywood | Michael Ovitz
Michael Ovitz, the legendary Hollywood agent and founder of CAA, reflects on his journey from a blue-collar upbringing to reshaping the entertainment industry. He shares behind-the-scenes stories of iconic films like Jurassic Park and discusses the importance of trust over contracts in business. Ovitz reveals insights from his time in Silicon Valley and his foresight about streaming's disruption of traditional models. His drive for innovation, loyalty to friends, and strategic partnership-building are key takeaways in this fascinating conversation.

40 snips
Jul 17, 2025 • 1h 42min
Borrowed Ten Grand, Turned Down Ten Billion | Stephen Ross
In this engaging conversation, Stephen Ross, a real estate titan and owner of the Miami Dolphins, shares his incredible journey from a two-family house in Detroit to transforming major urban landscapes like Hudson Yards. He reveals how getting fired fueled his entrepreneurial spirit and discusses his vision for building a Silicon Valley in South Florida. Ross also recounts the intriguing story behind owning the Dolphins and reflects on the importance of community and long-term thinking in both business and philanthropy.


