Big Shot
Harley Finkelstein (Shopify) and David Segal (DAVIDsTEA) interview Jewish entrepreneurs and cultural icons, preserving their behind-the-scenes stories, mishaps, and wins. The podcast explores the wisdom and laughs that would emanate from the walls of Kosher delis, celebrating the people who shaped an entire generation.
Episodes
How a 17-Year-Old From Tehran Turned $750 Into a Toy Empire | Isaac Larian
Isaac Larian is the founder and CEO of MGA Entertainment, the company behind Bratz, L.O.L. Surprise!, Little Tikes, and dozens of other iconic toy brands. But long before he built one of the largest private toy companies in the world, Isaac was a Jewish kid growing up in Tehran, where he faced antisemitism, bullying, and poverty. After arriving in America alone at 17 with just $753 in his pocket,
The Coney Island Kid Who Made Rocky, Goodfellas, and Raging Bull | Irwin Winkler
Irwin Winkler has spent more than six decades in Hollywood, producing films that have earned 52 Academy Award nominations and helped define generations of moviegoers. His credits include Rocky, Raging Bull, Goodfellas, The Right Stuff, and The Irishman, but the path that led to those films was anything but predictable.In this episode of Big Shot, hosts Harley Finkelstein and David Segal sit down w
From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After Another
Barry Diller started in the mailroom at the William Morris Agency, but he had no interest in becoming an agent. He didn’t hustle the way others did. Instead, he spent his time in the file room, reading everything he could and learning how the business actually worked. By his own account, he likely would have been fired if not for one thing: his connection to Danny Thomas.In this episode of Big Sho
The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff
Lew Wolff didn’t set out to become a successful developer or a professional sports team owner. He didn’t grow up around business, and by his own account, he stumbled into real estate almost by accident. But over the course of a decades-long career, he would go on to reshape downtown San Jose, partner with 20th Century Fox, and take ownership stakes in teams like the Oakland Athletics and Golden St
The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph Schaffer
Joseph Schaefer arrived in Canada from Poland in the 1930s and built his career in Montreal’s garment district at a time when the industry ran on instinct, relationships, and trust. He had an eye for fashion, a gift for reading people, and a way of doing business that set him apart early.In this episode of Big Shot, Joseph joins hosts Harley and David to reflect on how he found his way into the ga
Disney Fired Him. He Built DreamWorks, Shrek, and a $3.8B Empire | Jeffrey Katzenberg
Jeffrey Katzenberg was one of the youngest studio heads in Hollywood when he was named president of Paramount Pictures at just 31. Over the decades that followed, he would help shape modern animation and co-found DreamWorks alongside Steven Spielberg and David Geffen.In this episode of Big Shot, Harley and David sit down with Jeffrey to explore the experiences that shaped his career and leadership
Goldman Sachs Rejected Him. Years Later, He Ran the Place | Lloyd Blankfein
Lloyd Blankfein never chased a master plan. He focused on whatever was right in front of him, and those small decisions carried him from a Brooklyn housing project to leading Goldman Sachs through the worst financial crisis since the Great Depression.In this episode of Big Shot, Harley and David sit down with Lloyd to explore how that path unfolded. He talks about growing up in public housing and
She Escaped Communism, Reinvented Nail Polish, and Sold for a Billion Dollars
Before OPI, nail color was just another product on the shelf. Suzi Weiss-Fischmann gave it personality and built a global brand in the process.Suzi believed nail color could be personal, playful, and expressive. She pushed the entire industry forward with smarter formulas, bold branding, and shade names that became pop culture, from “I’m Not Really a Waitress” to “Lincoln Park After Dark.” In just
How a Blue-Collar Kid Built the Most Powerful Agency in Hollywood | Michael Ovitz
Every dealmaker in Hollywood has a story. Michael Ovitz has all of them.From Ghostbusters to Goodfellas, he packaged the films, brokered the talent, and rewrote the rules of power. What started as a rebellion inside William Morris became a $2 billion empire called CAA, and a playbook Silicon Valley still follows.In this episode of Big Shot, Harley and David sit down with Michael Ovitz, the legenda
Borrowed Ten Grand, Turned Down Ten Billion | Stephen Ross
In this episode of Big Shot, Harley and David sit down with Stephen Ross—real estate titan, Miami Dolphins owner, and the visionary behind Hudson Yards, CityPlace, and more—for a rare look inside his extraordinary life.From growing up in a two-family house in Detroit to transforming New York’s Hudson Yards and Miami’s CityPlace, Stephen’s story is deeply shaped by the Jewish entrepreneurial legacy
He turned a Florida swamp into one of America’s richest cities | Don Soffer
What kind of man looks at 800 acres of mosquito-infested swampland and sees high-end apartments, a golf course, and a luxury shopping mall? In 1967, Don Soffer made the biggest bet of his life: transforming undeveloped wetlands into what would become Aventura, one of Florida’s most iconic and extravagant communities. In this episode of Big Shot, Harley and David sit down with the 92-year-old visio
The King of Gaming: How Bobby Kotick Built and Sold Activision Blizzard for $69B
Bobby Kotick built a $69 billion empire from scratch—and the story is even crazier than it sounds.In this episode of The Big Shot, we sit down with gaming’s ultimate entrepreneur. Bobby takes us from hustling snacks at baseball games to building one of the most iconic tech companies in the world: Activision Blizzard. Hear how he cold-called Nintendo, got investment from Steve Wynn on a private jet
The Prosperity Formula: The Man Who Predicted—and Changed—the Future of Finance, Medicine, Education and Philanthropy | Mike Milken
In today’s episode of Big Shot, we sit down with Mike Milken—legendary financier, philanthropist, and chairman of the Milken Institute. Mike has been a driving force in medical research, public health, and education for over five decades. Fortune called him “The Man Who Changed Medicine,” and Forbes listed him among “Visionaries Reimagining Our Children’s Future.” Mike’s financial innovations help
The Queen of Branding: Lynda Resnick’s $6 Billion Empire of FIJI Water, POM, & Wonderful Pistachios
In this episode of Big Shot, we’re thrilled to welcome the legendary marketing visionary Lynda Resnick. As the co-owner of The Wonderful Company, Lynda has shaped iconic brands like POM Wonderful, Wonderful Pistachios, and FIJI Water into household names.
With her husband, Stewart, Lynda also turned The Franklin Mint into a cultural sensation and brought fresh ideas to the floral industry with Tel
How The Founder of Waze Went From Getting Fired To Building a Billion-Dollar Business | Uri Levine
In this special episode of Big Shot, recorded live at the iconic Kennedy Center in Washington, D.C., we’re joined by Uri Levine, the co-founder of Waze. Uri is a visionary entrepreneur whose journey includes building Waze, the world’s largest community-based traffic and navigation app, which Google acquired for over $1 billion. Beyond Waze, Uri has co-founded several impactful startups like Moovit
From College Dropout to Running Polo, Nike, Weight Watchers, and HSN | Mindy Grossman
In today’s episode of Big Shot, we’re joined by Mindy Grossman, former CEO of Weight Watchers, who led the company’s transformation into a global wellness brand. Like many of our past guests, Mindy’s journey involves perseverance, bold decisions, and calculated risk-taking.
Mindy’s remarkable career began with a surprising choice—dropping out of college. She then worked up to executive roles at Po
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 $400 million to $14 billion in revenue, revolutionizing casual wear and spotting a new retail opportunity that led to the creation of Old Navy.
His influence extends far beyond
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 learning to code to support her children.
Fueled by grit, a bit of luck, and a talent for connecting with extraordinary people, Heather built Indigo into Canada’s large
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 leading magazines, including Cosmopolitan, Allure, Mademoiselle, and Teen. She’s the author of nine beauty books, with five achieving bestseller status.
In 1991, Bobbi founded Bobbi
Billion-Dollar Threads: How Morris Goldfarb Stitched Together a Fashion Empire
In this episode of Big Shot, we sit down with the Chairman of the Board and Chief Executive Officer of G-III Apparel Group, Morris Goldfarb. Morris took over running his father’s company at the age of 24. His journey is deeply rooted in the inspiring legacy of his father, Aron Goldfarb, a Holocaust survivor who immigrated to the U.S. and founded G-III in 1956. Morris has transformed the company fr
The Godfather Of Fast Casual | Ron Shaich (Panera, CAVA)
When you think about a "convenience store manager," you probably don't imagine a future billionaire. But that's exactly the path Ron Shaich took from humble beginners selling Tollhouse cookies to a $7.5 billion restaurant empire. In this episode of Big Shot, Harley Finkelstein and David Segal welcome Shaich, the founder of Panera Bread, who shares his incredible journey from a no
He Inspired Warren Buffett, Became A Wall Street Legend, And Made Billions | Leon Cooperman
In this episode of Big Shot, we sit down with Wall Street titan Leon Cooperman. The son of working-class Polish immigrants and a first-generation college graduate, Leon founded Omega Advisors after a successful 25-year career at Goldman Sachs, where he rose to become Chairman and CEO of Goldman Sachs Asset Management.
Despite being one of the richest men on the planet, Leon lives modestly, even s
The Man Who Built New York City With No Money | Larry Silverstein
In this episode of Big Shot, we sit down with another legendary real estate developer, Larry Silverstein. Best known for the 99-year lease he signed for the World Trade Center, just six weeks before 9/11, Larry’s story is one of persistence and strategic partnerships—and a whole lot of chutzpah. He shares with us today how he leveraged partnerships, refurbished properties on a shoestring budget an
It's Better To Be Rich Than Right: Peter May
In this episode of Big Shot, we're honored to host business mogul Peter May. But his path to managing more than $7 billion is not what you might expect. What started as a career as an accountant at the prestigious KPMG quickly became something much different once Peter crossed paths with Nelson Peltz, igniting a dynamic partnership that spanned decades. Together, they founded Triarc Companies
From The Son Of A Postman To The $400 Billion Man: David Rubenstein
In this episode of Big Shot, we're thrilled to welcome the incredible David Rubenstein! As a co-founder of The Carlyle Group, one of the globe's top private equity firms, David's journey from a Baltimore kid with big dreams to a presidential advisor and business mogul is truly inspiring. Join us, as David reveals how he overcame rejection after President Carter lost his re-election and
From No-Name Producer To The Queen of Broadway: Fran Weissler
We’re back with Season 2 of Big Shot! In this episode of Big Shot, we're joined by Fran Weissler, a seven-time Tony award-winning producer and one-half of the dynamic duo behind Chicago, the longest-running American musical. Fran's journey epitomizes Jewish chutzpah, marked by bold choices—from leaving her first marriage to making decisive moves in her Broadway career. Today, Fran shares w
Jewish Titans and Untold Triumphs: Predicting the 2008 Crash, The Architect of Canadian Pride, and More Hidden Stories You've Never Heard!
When you sit down with iconic entrepreneurs for two to three hours, it's hard to include every story in an episode. But that doesn't mean every story isn't worth telling. On this episode of Big Shot shorts, you'll hear some wild tales that didn't make it into individual episodes of season 1. You'll learn how Ed Sonshine anticipated the 2008 crash, what Aldo Bensadoun did to
Why Billionaires Believe Work-Life Balance Is A Myth
One of the hardest parts of being an entrepreneur is the stress and anxiety of never having enough time. When ambition flows through your veins, it’s difficult to balance your desire to build something great with your love for your family, friends, and other interests. Being an entrepreneur requires sacrifice — but how do you do that without giving up what matters most? On this episode of Big Shot
Why Jews Are Entrepreneurs By Necessity
Did you know that less than .2 percent of the world is Jewish? And yet, more than 20 percent of all Noble Prize winners are Jewish. What explains the high likelihood of success? On this episode of Big Shot shorts, Harley Finkelstein and David Segal explore the history of Jewish entrepreneurship with legends Charles Bronfman, Aldo Bensadoun, and Ed Sonshine. Their competitive advantage? They had ev
Integrity Is More Than A Principle -- It's The Secret To Entrepreneurial Success
Some of the best stories in business are the ones you never hear about. They are the deals that fell through, the partnerships that never happened, and the employees who didn’t make it. Behind those moments are decisions that shape some of the best businesses. And, when you speak with some of the world’s greatest entrepreneurs, you realize that those moments are shaped by strong values. In particu
How Business Legends Build The Best Teams
It's cliché to say that you can see further when standing on the shoulders of giants. But it's also a mentality that has served some of the most successful entrepreneurs. No matter how brilliant the individual, great leaders know that building a world-class team can take a company from being a good idea to becoming a household name. And wise employees know that if they can find a leader wh
Legacy Lessons: The Enduring Wisdom of Our Grandparents for Success Today
In today’s episode, we explore stories from our guests on how their parents and the previous generation profoundly impacted their lives. You’ll hear from Ed Sonshine, Jonathan Wener, Issy Sharp, Charles Bronfman, and Aldo Bensadoun about how they learned their relentless work ethic from their parents and the power of learning by example. It’s a great example of how each generation stands on the sh
How To Live A Rich Life Through Giving Back
In today’s episode, we dive into the concept of philanthropy and its importance for each of our season 1 guests. Tikkun Olam is a concept in Judaism that refers to various forms of action intended to repair and improve the world. You’ll hear this theme from each of today’s guests. Whether it is Issy Sharp explaining why he has helped raise $1 billion for the Terry Fox Run or Jonathan Wener saying
Winning Big with Chutzpah: Lessons from the Titans of Entrepreneurship
Looking for a masterclass on taking chances and winning big? This episode of Big Shot looks at the one trait shared by all the successful entrepreneurs and billionaires on the podcast -- chutzpah. It's one thing to say you can't fear failure. And it's something completely different to act in ways that seem crazy at the moment but turn out to be the perfect move. This episode shares the
An Unfiltered Conversation With The Founder of The Four Seasons: Issy Sharp (Part 2)
We’re back today for part two with The Four Seasons Hotels and Resorts founder, Issy Sharp. If you didn’t check out part 1, be sure to watch or listen. In this episode, we explore how Mcdonald's surprisingly had the biggest impact on the Four Seasons' approach to hospitality and led to Issy firing most of his executive team, why the Four Seasons changed their entire business model and don’
How Issy Sharp Built The Four Seasons and Transformed The Hospitality Industry Forever (Part 1)
Today we’re joined by none other than Isadore (Issy) Sharp, the founder of The Four Seasons. We’re talking about one, if not the most iconic luxury hotel brands in the world. His story is incredible. From growing up and working in construction. To how he met his wife that’s he’s still with over 70 years later. This episode was so damn good we had to split it into two parts. In part one, you’ll lea
Ed Sonshine: From Displaced Persons Camp To a Multi-Billion Dollar Real Estate Empire
Ed Sonshine is one of those people you could speak with for hours and barely scratch the surface of his life. Born in Bergen-Belsen Displaced Persons Camp after World War II to two Holocaust survivors, he immigrated to Canada as a young child. After already becoming a very successful lawyer, he founded RioCan, which, at the time, was the first REIT (Real Estate Investment Trust) in Canada. As of t
The Power Of Kindness: How Jonathan Wener Turned A $10k Loan Into A $15 Billion Empire
Jonathan Wener is proof that nice guys don't finish last. The founder of Canderel, which has developed over 80 million square feet throughout Canada, has a reputation for being one of the nicest people you'll ever meet. In this episode of Big Shot, you'll discover how his bold decisions at 25 turned a $10,000 loan into more than $15 billion, how he always used kindness to create opport
Building A Billion-Dollar Shoe Brand From Scratch: Aldo Bensadoun
If you have ever wondered if you have what it takes to become an entrepreneur, then listening to Aldo Bensadoun's story could be a life-changing experience. Entrepreneurship is a natural calling for some. For others, it's a destiny that seems to find them. In this episode, Aldo takes us on a journey from his humble beginnings to building a billion-dollar brand that may have never existed i
The Man Who Brought Baseball to Canada and Founded Birthright: Charles Bronfman
Some entrepreneurs don't just build businesses, they take bold risks that can shape a country or revitalize a religion. That's Charles Bronfman. On the first episode of Big Shot, hosted by Harley Finkelstein and David Segal, you'll learn about Bronfman’s incredible upbringing, lessons, and experiences that inspired many transformational initiatives. From watching his father build Seagr
Welcome to Big Shot
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.
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Where To Find Big Shot
Website: bigshot.s
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