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.
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The Coney Island Kid Who Made Rocky, Goodfellas, and Raging Bull | Irwin Winkler
Thursday, June 11, 2026 • Duration 01:17:33
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 shaped his remarkable career. From the William Morris mailroom to launching an agency with Robert Chartoff, from representing Julie Christie to hearing Sylvester Stallone pitch Rocky, Irwin shares the stories behind a life spent at the center of the movie business.
Along the way, he reflects on the people who changed his life, the opportunities he almost missed, and the unexpected chain of events that led from a kid growing up in Brooklyn to one of the most successful producers in Hollywood history.
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In This Episode We Cover:
(00:00) Intro
(03:13) Growing up in Williamsburg, Brooklyn
(07:11) Moving to the Sea Gate in Coney Island
(08:26) Irwin's first attempt at NYU
(10:22) Why he enlisted in the Army
(10:55) Back to NYU after the Army
(12:00) How he got interested in working for a talent agency
(14:20) From summer mailroom gig at William Morris to full-time job
(18:45) Climbing the ranks at William Morris
(23:18) Leaving William Morris to work with Bob Chartoff
(29:14) How Julie Christie helped launch his producing career
(39:47) Meeting Sylvester Stallone and hearing the Rocky pitch
(48:53) Rocky's reception and the reshoot that saved the film
(51:48) How he started working with Martin Scorsese
(53:54) Managing productions and safeguarding creatives
(57:01) How Rocky II helped get Raging Bull made
(59:45) Funding movies then vs. now
(1:01:47) Irwin’s thoughts on AI and CGI
(1:03:14) The role of luck, hard work, and partnerships in his success
(1:07:12) The story of meeting Jack Warner and the Six-Day War
(1:10:21) Irwin's perspective on Jewish success in business and entertainment
From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After Another
Thursday, May 21, 2026 • Duration 49:12
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 to running studios, building networks, and shaping modern media. He shares how his ambition came later, not as something he chased but something he discovered, and how his career was shaped as much by timing and luck as by intention.
Along the way, Barry walks through the decisions that defined his career, from rising quickly through ABC and becoming chairman of Paramount at 32, to building the Fox network alongside Rupert Murdoch, and later taking control of IAC and acquiring companies like Expedia.
This is a conversation about instinct, timing, and the willingness to walk through the door when it opens.
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In This Episode We Cover:
(00:00) Intro
(03:32) Barry’s early heroes and influences
(05:16) Where his ambition came from
(06:50) Getting his start in the mailroom at the William Morris Agency
(08:53) What he learned from reading client files at William Morris
(12:10) Working as an assistant at William Morris
(14:00) How he got a job at ABC
(16:32) Barry’s thoughts on serendipity
(19:20) Developing The Movie of the Week and miniseries at ABC
(22:32) Becoming chairman of Paramount at 32
(26:44) Working with Charles Bluhdorn
The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff
Thursday, April 30, 2026 • Duration 01:21:07
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 State Warriors.
In this episode of Big Shot, Lew sits down with Harley and David to reflect on the unconventional path that led him there. He shares how the sudden death of his father forced him to grow up quickly, how a chance decision in college set him on a career in real estate, and how one unexpected opportunity led to a role at Fox and a headline that would change everything overnight.
Along the way, Lew explains why he built his career around partnerships, how he thinks about choosing the right people to work with, and why he has always prioritized relationships over short-term profit. He also reflects on his time in professional sports, including the story behind Moneyball, the challenges of public scrutiny, and the behind-the-scenes dynamics that shaped the future of the A’s.
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In This Episode We Cover:
(00:00) Intro
(02:25) Lew’s early years growing up in the Midwest
(05:54) How his father’s death changed his path
(10:28) Growing up Jewish in St. Louis
(11:43) His first job and move to Los Angeles
(14:34) Starting his own firm and selling to Booz Allen
(17:18) His work with 20th Century Fox
(24:39) Balancing the San Jose development with his work at Fox
(27:20) How his studio office helped attract clients
(29:21) How Bud Selig led him to buy a stake in the Oakland A’s
(38:18) Lew’s philosophy on partnerships and how to choose them
The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph Schaffer
Thursday, April 9, 2026 • Duration 37:11
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 that lasted decades, why he never lost a partner, and how he gave others ownership long before equity was common practice.
This is a story about a different era of entrepreneurship—one where deals were built on reputation, capital came through relationships, and success depended on understanding both the product and the people behind it. Joseph also reflects on what’s changed, why that kind of success is harder to replicate today, and the role his values and faith played in how he built his life and business.
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In This Episode We Cover:
(00:00) Intro
(01:06) Early days after immigrating to Canada
(03:10) How Joseph got his start in entrepreneurship
(07:38) Learning the craft with help from his sister
(09:55) When he brought on salespeople
(11:27) How he built Chabanel
(14:20) Joseph’s approach to capital and equity
(18:16) How Joseph won over banks
(22:24) Why Joseph’s success wouldn’t be repeatable in today’s market
(25:45) How Joseph managed partnerships
(29:00) Joseph’s legacy
(31:52) Joseph’s advice for young entrepreneurs
(32:50) His relationship with the Bronfmans
Disney Fired Him. He Built DreamWorks, Shrek, and a $3.8B Empire | Jeffrey Katzenberg
Thursday, March 19, 2026 • Duration 01:14:05
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 alongsideSteven 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, and on a moment with Kirk Douglas that reinforced the idea that you have not truly learned how to live until you have learned how to give.
Jeffrey traces his path through Hollywood, from working with Barry Diller to helping lead Disney during a pivotal era for animation, and how being fired from Disney led him to build DreamWorks.
Along the way, Jeffrey reflects on failure, success, and the mindset that has guided him through decades in Hollywood, and shares why he never rests on past success, keeping his eyes on what’s next.
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In This Episode We Cover:
(00:00) Intro
(02:40) Lessons from his father and Kirk Douglas
(12:01) Volunteering for NYC mayor John Lindsay
(12:40) Growing up with dyslexia
(16:44) The philosophy of exceeding expectations
(25:24) Jeffrey’s role in revitalizing Disney animation
(33:32) Storytelling lessons from Walt Disney
(37:16) Building DreamWorks as its own brand
(43:29) Getting fired from Disney and forming the Dreamworks team
(57:04) Movie studio economics
(59:32) Venture capital vs. filmmaking
(1:05:26) A story about Jeffrey’s father and the drive of Jewish parents
Goldman Sachs Rejected Him. Years Later, He Ran the Place | Lloyd Blankfein
Thursday, December 25, 2025 • Duration 01:48:58
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 a suit because he had no idea what college culture looked like. He reflects on the dislocation of moving between the projects and the Ivy League and how he learned to navigate both worlds without ever feeling fully at home in either.
Lloyd traces his shift from law to commodities, what he absorbed inside J. Aron, and how a crisis inside Goldman in the 1980s reshaped the firm and opened unexpected doors. He also shares what it was like to lead Goldman Sachs through 2008, why Warren Buffett’s support mattered at a defining moment, and what it took to keep the firm intact while the global financial system was breaking apart.
It is a conversation about chance, focus, resilience, and the surprising places a life can go when you simply take the next step.
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In This Episode We Cover:
(00:00) Intro
(05:15) Lloyd’s early days
(07:05) How Lloyd graduated early
(08:53) How Lloyd ended up at Harvard at 16
(10:56) A glimpse at just how humble his beginnings truly were
(13:42) What it was like arriving at Harvard with no roadmap
(19:37) Why top public-university talent can match (and sometimes surpass) the Ivies
(20:27) What it was like moving between worlds
(25:05) Why it took a long time to adjust to the burden of great wealth
(27:11) What led Lloyd to law school
She Escaped Communism, Reinvented Nail Polish, and Sold for a Billion Dollars
Thursday, December 11, 2025 • Duration 01:22:34
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.
In this episode of Big Shot, Harley and David sit down with Suzi to explore the instincts that fueled that rise. She talks about welcoming competition, using storytelling to make an emotional connection with customers, and expanding from salons into Walmart without losing trust or quality. Suzi also shares how her Jewish upbringing influenced her approach to business, from the drive that comes from starting with very little to the values of community and responsibility that guided every big decision.
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In This Episode We Cover:
(00:00) Intro
(03:23) Growing up in communist Hungary with two Holocaust-survivor parents
(05:54) How honoring faith brought Suzi’s mom back to Auschwitz
(07:32) Why Suzi’s family fled Hungary
(12:40) Suzi’s family’s transitional time in Israel
(15:50) Where Suzi’s work ethic came from
(18:53) Suzi’s adolescence in New York
(23:27) Suzi’s move to Los Angeles
(24:52) How a dental-supply store ended up experimenting with acrylic nails
(29:37) OPI’s first trade show
(32:36) Why competition is good
(33:58) How Starbucks inspired Suzi to personalize nail polish
(36:44) Why OPI named polishes after food and places and how the naming process worked
How a Blue-Collar Kid Built the Most Powerful Agency in Hollywood | Michael Ovitz
Tuesday, November 11, 2025 • Duration 01:22:42
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 a working-class childhood to representing the world's biggest stars, Michael’s story is one of obsession, reinvention, and relentless ambition. He helped shape more than 300 films, including Jurassic Park, Ghostbusters, Tootsie, Stand by Me, and Goodfellas, while transforming how deals, talent, and ideas move through the entertainment industry.
This episode is brought to you by Firebelly Tea. Use code bigshot15 for 15% off your order https://www.firebellytea.com/
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In This Episode We Cover:
(00:00) Intro
(01:39) Michael’s early years
(02:53) How Jewish mothers blend boundless belief with practical ambition
(06:15) Michael’s advice to a failed businessman
(15:44) How Marc Andreessen pulled Michael into Silicon Valley
(21:00) How early anti-semitism made Eisner’s betrayal cut deeper
(25:37) The Yahoo deal Eisner blocked
(30:25) The story behind the Jurassic Park pitch and Spielberg’s involvement
(34:11) The hit-to-miss ratio in Hollywood, and how Michael’s movies were almost always hits
(36:15) How stagnation at William Morris drove Michael to build something new
Borrowed Ten Grand, Turned Down Ten Billion | Stephen Ross
Thursday, July 17, 2025 • Duration 01:42:13
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 refinery in the Midwest, and his uncle Max Fisher, a renowned businessman and philanthropist, Stephen saw early what was possible through grit, vision, and belief.
He shares how getting fired set him on the path to starting his own business, why he’s now building infrastructure in Palm Beach County to create South Florida’s next “Silicon Valley,” and the stories behind owning the Miami Dolphins and bringing Formula 1 racing to Miami.
We discuss the following:
• How his grandfather built the largest independent oil refinery in the Midwest
• Why getting fired was the best thing that ever happened to him
• Why he believes New York is still the best place to start anything
• Why he held onto CityPlace through years of losses—and how it finally paid off
• His $1.5B asset sale before the 2008 crash
• The infrastructure he’s bringing to Palm Beach County to build a new “Silicon Valley”
• Why he sold 1.5 billion worth of assets before the financial crisis of 2008
• The story behind purchasing the Miami Dolphins
• Why he turned down a $10B offer for the Dolphins, Hard Rock Stadium, and F1
• How daily school drop-offs helped Stephen build a lasting bond with his daughters
• His perspective on Jewish excellence in entrepreneurship and philanthropy
• His advice for young entrepreneurs
He turned a Florida swamp into one of America’s richest cities | Don Soffer
Thursday, June 12, 2025 • Duration 49:30
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 governor to back his development plan (after a well-timed flight to Tallahassee) to bringing in golf legend Robert Trent Jones to design a course, Don sold a dream that turned into a $4 billion reality. He built Turnberry resort, launched Aventura Mall, and packed them with celebrities—from Elton John to Madonna and John McEnroe.
Decades before “influencer marketing” was a thing, Don was using star power to shape a city.
In this episode, you’ll hear about:
• The environmental pushback Don faced after buying swampland—and how he got the green light from the governor of Florida after chartering a jet and flying to Tallahassee
• Don’s celebrity-packed playbook: how he used influencers before we even had a word for it
• Don’s take on why Jewish people have become such successful entrepreneurs
• Don’s definition of common sense—and approach to solving complex problems with simplicity
• Why he says it’s a privilege to have a hard problem to solve
• His advice for the next generation of Jewish entrepreneurs
• And much more!
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In This Episode We Cover:
(00:00) Intro
(02:07) How Don accidentally swallowed his dad’s glass eye
(03:03) Don’s early work building shopping malls with his father
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