

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

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.

18 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.

36 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.

7 snips
Jun 12, 2025 • 50min
He turned a Florida swamp into one of America’s richest cities | Don Soffer
Don Soffer, a trailblazing real estate developer, recounts his audacious transformation of 800 acres of swampland into the luxurious Aventura, Florida. He shares the thrilling story of securing state support for his project by charming the governor with a surprise flight to Tallahassee. Discover how he leveraged star power long before influencer marketing became a trend, attracting celebrities to Aventura. Don also reflects on the significance of Jewish entrepreneurship and offers valuable advice for future generations tackling tough challenges.

6 snips
Apr 10, 2025 • 1h 23min
The King of Gaming: How Bobby Kotick Built and Sold Activision Blizzard for $69B
Bobby Kotick, the mastermind behind Activision Blizzard, recounts his journey from hustling snacks in NYC to leading a $69 billion company. He shares wild anecdotes, like cold-calling Nintendo and charming Steve Wynn into an investment on a private jet. Discover how he revived a bankrupt Activision, leveraging classic games as billion-dollar blueprints. Bobby also reflects on leadership philosophies and the emotional rollercoaster of selling to Microsoft, revealing the blend of grit and innovation that fueled his success in the gaming industry.

26 snips
Mar 6, 2025 • 1h 32min
The Prosperity Formula: The Man Who Predicted—and Changed—the Future of Finance, Medicine, Education and Philanthropy | Mike Milken
Mike Milken, a legendary financier and philanthropist, shares his lifelong commitment to innovation and equity. He discusses how childhood experiences shaped his empathetic approach to philanthropy and entrepreneurship. Milken reflects on the impact of the Watts riots and market crashes, revealing how they created new opportunities. He emphasizes the power of financial technology in advancing health and education, while sharing insights on resilience and the transformative role of private industry in tackling global challenges. A captivating glimpse into the mind of a visionary!

Jan 30, 2025 • 1h 12min
The Queen of Branding: Lynda Resnick’s $6 Billion Empire of FIJI Water, POM, & Wonderful Pistachios
Lynda Resnick, co-owner of The Wonderful Company, is a branding powerhouse behind FIJI Water, POM Wonderful, and Wonderful Pistachios. She shares her journey from child actor to marketing mogul, detailing her success in turning basic products into billion-dollar brands. Lynda reveals her unique approach to self-funding philanthropy and how her Jewish heritage shapes her values. Listeners will be inspired by her commitment to community health and her reflections on balancing creativity with business success.

Dec 12, 2024 • 19min
How The Founder of Waze Went From Getting Fired To Building a Billion-Dollar Business | Uri Levine
Uri Levine, co-founder of Waze and author of "Fall in Love with the Problem, Not the Solution," shares his remarkable entrepreneurial journey from failure to success. He reflects on critical lessons learned from his father about embracing failure and prioritization. Uri recounts a clever fundraising hack involving mapping investors' homes to showcase Waze's potential. He also highlights the cultural drive within the Jewish community to foster innovation and positive change, and discusses the financial impact of Waze's acquisition that created many millionaires.

Nov 21, 2024 • 1h 23min
From College Dropout to Running Polo, Nike, Weight Watchers, and HSN | Mindy Grossman
Mindy Grossman, former CEO of Weight Watchers and a veteran leader with a rich background at Nike and Polo Ralph Lauren, shares her incredible journey from college dropout to industry titan. She delves into the importance of calculated risk-taking and her mantra of 'passion, purpose, and impact.' Mindy reveals how she transformed toxic workplaces, notably revitalizing the culture at HSN. She also discusses her impactful collaboration with Oprah and insights into embracing Jewish identity as a driver for success. Get ready for a dose of inspiration!

Oct 24, 2024 • 1h 25min
The Merchant Prince: The Man Behind The Gap, Old Navy, and J. Crew | Mickey Drexler
Mickey Drexler, a retail legend, transformed brands like The Gap and Old Navy. He shares insights from his humble Bronx beginnings and emphasizes the importance of people skills in hiring. Mickey discusses his unique decision-making style, valuing urgency over indecision, and reflects on his friendship with Steve Jobs. Listeners learn about the emotional aspects of fashion and Mickey's innovative approach to market research. His journey highlights resilience, the impact of mentorship, and a deep passion for retail.


