Episodes

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, Isaac worked the graveyard shift washing dishes while putting himself through college. He later b...

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 with Irwin to look back on the twists, turns, relationships, and moments of good fortune that sha...

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 Shot, Barry sits down with Harley and David to reflect on the path that took him from that mailroom...

Lew Wolff didn’t set out to become a billionaire 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 State Warriors.


In this episode of Big Shot, Lew sits down with Harley and David to reflect on the...

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 garment trade and helped shape what Chabanel would become. He shares how he built partnerships tha...

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 approach. He reflects on lessons from his father, whose generosity left a lasting impression, a...

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 sharing a room with his grandmother, then suddenly finding himself at Harvard at 16, arriving in...

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 six years after its founding, OPI became the number one professional nail brand in America.


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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 legendary founder of Creative Artists Agency and the man who redefined power in Hollywood.


From ...

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. Inspired by his grandfather, a Russian immigrant who built the largest independent oil refiner...

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 visionary to hear how it all happened—straight from the source.


From convincing the Florida governo...

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, took over a bankrupt video game company, and turned it into an empire that Microsoft bought fo...

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 helped launch industries like cable TV, homebuilding, and cellular technology. Beyond finance, he ...

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 Teleflora’s innovative, long-lasting gifts.


Join us as Lynda takes us on a journey through her ex...

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 (acquired by Intel), FeeX, and Engie. He’s also the author of Fall in Love with the Problem, Not th...

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 Polo Ralph Lauren, Nike, the Home Shopping Network, and Weight Watchers. In our conversation today,...

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 The Gap—he also founded Madewell, served on Apple’s board for over a decade, and now works alon...

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 largest bookseller. However, Heather's ambitions extend beyond her role as founder and CEO. She is also a devot...

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 Brown Cosmetics, which Estée Lauder acquired for $74.5 million four years later. Bobbi had a 25-y...

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 from a small women's leather outerwear business into a global fashion powerhouse, managing brands like...

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 nonprofit convenience store to his pivotal decision to create Panera Bread. Ron is a master at finding the trends others...

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 still changing his own lightbulbs.


In this fascinating conversation, he shares insights on achie...

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 and built a business that today is valued at over $10 billion. As with many successful Jewish entrepre...

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 and pioneered innovative funding strategies, revitalizing numerous struggling businesses. They eventuall...

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 pivoted into private equity. Learn why he's dedicated to giving back through initiatives like the Giving Pledge...

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 with us stories from her journey, including breaking into Broadway at the age of 50 and producing Othello wit...

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 break into America when so many others failed, how Charles Bronfman shaped Canadian pride, and Jonathan Wener's wild story ...

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 Shorts, Issy Sharp, Charles Bronfman, and Ed Sonshine reveal their regrets, rules, and recommendati...

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 everything to lose, giving them no choice but to find a way to win.




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In This Episode, We Cov...

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 particular, the best entrepreneurs lean into integrity to turn risks into rewards. On this episode of Big S...

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 who understands the value of a team, then the opportunity and upside can be unlimited. In this episode, you'll...

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 shoulders of the giants that came before them.


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In This Episode, We Cover:
(00:00) Welcome to B...

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 that the best way to live a rich life is by giving back. We explore the importance of giving to the ...

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 combined wisdom of Ed Sonshine, Charles Bronfman, Aldo Bensadoun, Jonathan Wener, Issy Sharp, and hosts Harley ...

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’t own any real estate, and how the death of his son helped inspire him to help the Terry Fox run to become t...

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 learn what Issy’s upbringing was like, why Issy has never felt fear, the most important concepts that m...

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 this recording, RioCan operates 193 properties, has over 33 million in leasable square feet, and an e...

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 opportunity, and how he approached objections and adversity in his career. —


Where To Find Big Shot:


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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 if it wasn't for one life-changing decision that turned a loyal employee into a trailblazing founder who stil...

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 Seagram’s to bringing the Expos to Canada and founding Birthright Israel. Bronfman left a legacy in business, charity...

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.show
YouTube: https://www.youtube.com/@bigshotpodcast
TikTok: https://www.tiktok.com/@bigshotshow
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