The Merchant Prince: The Man Behind The Gap, Old Navy, and J. Crew

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.

Recent Episodes

Oct. 24, 2024

The Merchant Prince: The Man Behind The Gap, Old Navy, and J. Crew | Mickey Drexler

In today’s episode of Big Shot , we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion. Over his 18-year tenure at The Gap, Mickey took the company from $…
Sept. 19, 2024

From Single Mom to Billion Dollar Book Business | Heather Reisman (Founder & CEO, Indigo)

In this special live episode of Big Shot , recorded at StartupFest, we are excited to welcome Heather Reisman, the trailblazing entrepreneur behind Indigo Books & Music. Heather's remarkable journey began as a single mother …
Sept. 5, 2024

Bobbi Brown's Billion Dollar Beauty Legacy

Harley Finkelstein and David Segal are back with Season 3 of Big Shot ! Today, we chat with beauty industry icon Bobbi Brown. Known for her work as a makeup artist, Bobbi’s expertise has been showcased on the covers of leadi…

About the Hosts

Harley Finkelstein Profile Photo

Harley Finkelstein

Shopify President

David Segal Profile Photo

David Segal

Co-Founder of Firebelly Tea - previously the “David” of DAVIDsTEA.