Big Shot is a celebration of chutzpah and entrepreneurship

New podcast tells the stories of  Jews who succeeded against all odds, out of necessity, out of chutzpah, and out of purpose

Imagine if the walls of kosher delis could speak, what kinds of stories would they tell us? This is the imagination behind the new podcast, Big Shot, launched by Jewish entrepreneurs Harley Finkelstein of Shopify and David Segal of DavidsTEA.  Theirs is a passion project that aims to tell the histories and behind-the-scenes machinations of the great Jewish entrepreneurs who inspired them on their own successes.  

“We did not want to just create another podcast,” explains Finkelstein in the opening episode, “We wanted to do something different and cover people who are not normally on the podcast circuit but belonged there - arguably more than anyone else. … Jews who succeeded against all odds, out of necessity out of chutzpah, and out of purpose.” 

There is a wonderful sense of energy and charisma that is captured in the interviews with both Finkelstein and Segal sharing a warm enthusiasm for their subjects - imagine one very famous billionaire telling Segal how he has enjoyed his tea. While geared toward business, the podcast will also appeal to those interested in Jewish values, history, and tikkun olam.  

Inspired in part by “Distilled: A Memoir of Family, Seagram, Baseball, and Philanthropy,” by Charles Bronfman, Finkelstein and Segal decided to create Big Shot, an archive of the stories, lessons, and wisdom of Jewish entrepreneurs who took risks, overcame the odds, and created legendary businesses. 

Big Shot went live at the end of March and came out swinging with the first episode featuring - surprise - none other than influential businessman and philanthropist Bronfman himself. (As Finkelstein says: “Charles ‘freakin’ Bronfman.”)  

During the interview, Bronfman spoke candidly about purchasing the Montreal Expos in 1968 sharing that “the reason I brought baseball to Canada, is that I wanted to prove to everyone, including my father, that I am an entrepreneur on my own.”   

He also discussed the role of philanthropy in his life, particularly the establishment of Birthright Israel, which has provided free trips to Israel for more than 750,000 young Jewish adults – including Finkelstein who shared how the trip impacted him.  

A recurring element in Big Shots is the question of how chutzpah married to philanthropy plus purpose may be the secret ingredients behind the success of Jews in business. 

Bronfman himself says it: “Chutzpah in business is damn good. If you don’t have it, you won’t get far.” This came up again in the second episode of Big Shot, “Building a Billion-Dollar Shoe Brand from Scratch,” featuring Aldo Bensadoun, who says “chutzpah is courage. There are key moments in life when you make decisions that could go one way or another” and a successful entrepreneur has to have the courage to make these tough decisions. 

“You typically associate chutzpah with aggression, this winner-takes-it-all, dog-eat-dog sort of thing but what Aldo Bensadoun proves is that you can be kind and have high integrity and you can also win,” said Segal.  

 “The more kind you are, the more you win, and the more you win, the more you can build, and the more you can build, the more impact you can have  - it’s a cycle of reciprocity,” says Finkelstein. 

As Bensadoun says: “We are put on earth to fix the world and each one of us should make sure that [we try to do] whatever we can to make the world a better place … even if it’s a black day, you still get up in the morning and ask yourself, how can I do it better?” 

Want to get inspired? You can watch Big Shot here or tune in on Spotify or Apple.