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by Big Shot
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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- Apr 30, 20261h 21m
The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff
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 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.—In This Episode We Cover: Intro Lew’s early years growing up in the Midwest How his father’s death changed his path Growing up Jewish in St. Louis His first job and move to Los Angeles Starting his own firm and selling to Booz Allen His work with 20th Century Fox Balancing the San Jose development with his work at Fox How his studio office helped attract clients How Bud Selig led him to buy a stake in the Oakland A’s Lew’s philosophy on partnerships and how to choose them Buying and selling his stake in the Golden State Warriors The kind of work he enjoys and what he credits for his success The story behind Moneyball Why he stays focused on the future Why he prioritizes relationships over profit How he handled negative press as owner of the A’s How the Giants blocked the A’s from building a new stadium How he learned to let things go Lew and Bud’s attempt to integrate their fraternity His thoughts on Jewish entrepreneurship What he’s most proud of—Where To Find Lew Wolff:• Website: https://www.wolffurban.com/ Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Apr 9, 202637 min
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 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.—In This Episode We Cover: Intro Early days after immigrating to Canada How Joseph got his start in entrepreneurship Learning the craft with help from his sister When he brought on salespeople How he built Chabanel Joseph’s approach to capital and equity How Joseph won over banks Why Joseph’s success wouldn’t be repeatable in today’s market How Joseph managed partnerships Joseph’s legacy Joseph’s advice for young entrepreneurs His relationship with the Bronfmans The role of faith in his life—Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Mar 19, 20261h 14m
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 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.—In This Episode We Cover: Intro Lessons from his father and Kirk Douglas Volunteering for NYC mayor John Lindsay Growing up with dyslexia The philosophy of exceeding expectations Jeffrey’s role in revitalizing Disney animation Storytelling lessons from Walt Disney Building DreamWorks as its own brand Getting fired from Disney and forming the Dreamworks team Movie studio economics Venture capital vs. filmmaking A story about Jeffrey’s father and the drive of Jewish parents Dealing with failure —Where To Find Jeffrey Katzenberg:• LinkedIn: https://www.linkedin.com/in/jeffrey-katzenberg-4b3b47123• Facebook: https://www.facebook.com/jeffrey.katzenberg• Website: https://www.wndrco.com Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Dec 25, 20251h 48m
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 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.—In This Episode We Cover: Intro Lloyd’s early days How Lloyd graduated early How Lloyd ended up at Harvard at 16 A glimpse at just how humble his beginnings truly were What it was like arriving at Harvard with no roadmap Why top public-university talent can match (and sometimes surpass) the Ivies What it was like moving between worlds Why it took a long time to adjust to the burden of great wealth What led Lloyd to law school Lloyd’s approach of thinking one step ahead Why Lloyd quit practicing law Lloyd’s pivot to finance and initial rejection from Goldman Sachs The J. Aron role that pulled Lloyd into Goldman Inside the meritocracy of Goldman Sachs How Lloyd ended up making partner at Goldman Sachs unexpectedly Building trust across cultures What changed after making partner What sparked Lloyd’s retirement and renewed focus on learning How the 1994 crisis set the stage for Lloyd to become CEO Steering the firm through the 2008 financial crisis The deal with Warren Buffett Risk-taking vs. risk management How anxiety fuels Lloyd’s risk management style Lloyd’s biggest accomplishment at Goldman Sachs A case for self-acceptance —Where To Find Lloyd Blankfein: • X: https://x.com/lloydblankfeinWhere To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Dec 11, 20251h 22m
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 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.—In This Episode We Cover: Intro Growing up in communist Hungary with two Holocaust-survivor parents How honoring faith brought Suzi’s mom back to Auschwitz Why Suzi’s family fled Hungary Suzi’s family’s transitional time in Israel Where Suzi’s work ethic came from Suzi’s adolescence in New York Suzi’s move to Los Angeles How a dental-supply store ended up experimenting with acrylic nails OPI’s first trade show Why competition is good How Starbucks inspired Suzi to personalize nail polish Why OPI named polishes after food and places and how the naming process worked The time Suzi presented to Barbara Broccoli The perks and bonuses OPI gave to their employees How OPI fixed its lipstick mistake How success affected Suzi Entering Walmart and growing beyond the professional market How Suzi’s divorce impacted the family business The emotional impact of selling OPI The Jewish work ethic How to raise resilient, hardworking children—Where to find Suzi Weiss-Fischmann: • Instagram: https://www.instagram.com/1stladyofcolors• Facebook: https://www.facebook.com/1stladyofcolors• Website: https://1stladyofcolors.comWhere To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Nov 11, 20251h 22m
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 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/—In This Episode We Cover: Intro Michael’s early years How Jewish mothers blend boundless belief with practical ambition Michael’s advice to a failed businessman How Marc Andreessen pulled Michael into Silicon Valley How early anti-semitism made Eisner’s betrayal cut deeper The Yahoo deal Eisner blocked The story behind the Jurassic Park pitch and Spielberg’s involvement The hit-to-miss ratio in Hollywood, and how Michael’s movies were almost always hits How stagnation at William Morris drove Michael to build something new Lessons from William Morris’s shortcomings that shaped CAA’s DNA How Michael signed every member of Saturday Night Live The story of Michael’s first client and first big stars The story behind Janklow and Nesbit and what Michael likes about Silicon Valley Michael’s true talent How Michael and Andy Grove envisioned streaming before Hollywood was ready The ripple effects of streaming across entertainment Michael’s thesis about the success of Jews and Catholics—Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Jul 17, 20251h 42m
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. 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 • And much more!—In This Episode We Cover: Intro Stephen’s childhood in Detroit Lessons and inspiration from his grandfather and uncle Stephen’s rocky start in Florida and struggles in school How Stephen got into the University of Michigan and became a good student How getting fired sparked his first business Early business goals and the fundraising hurdles that led to bootstrapping Stephen’s diversification strategy How Stephen found great people to work with What Stephen loves about the real estate business Why the 90s market wasn’t ready for CityPlace The story behind Hudson Yards and the Olympic stadium that fell through Why Stephen says his latest project will be the most impactful How to maintain momentum while building large projects What it was like buying the Miami Dolphins Why he brought F1 to Miami Stephen’s philanthropy and why giving back is important What drives Jewish excellence in business and giving How he built and maintained a relationship with his daughters How he survived a tough time in the 90s AI's impact on the future Advice for young entrepreneurs and how he values relationships—Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
- Jun 12, 202549 min
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 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! —In This Episode We Cover: Intro How Don accidentally swallowed his dad’s glass eye Don’s early work building shopping malls with his father Why Don trusted his intuition and took a chance on developing swampland in Florida How Don got the governor of Florida on board to green light his project Early influencers: How Don leveraged the power of celebrities Building Aventura Mall Don’s common-sense approach Don’s relationship with his father Why Don says it’s terrible to run a family business Don’s current roles and how he set his kids up Don’s explanation for the success of the Jewish people A dinner with Frank Sinatra Advice for young Jewish entrepreneurs Where Don got his confidence and conviction How Don saved the Pittsburgh Mall after the excavator destroyed private property Don’s thoughts on when to sell and when not to Don’s friendship with Tony Bennett How to cultivate strong business relationships Don’s advice to future generations of Soffers Why Don still thinks Florida is a good place to develop Closing —Where To Find Big Shot: • Website: https://www.bigshot.show/• YouTube: https://www.youtube.com/@bigshotpodcast • TikTok: https://www.tiktok.com/@bigshotshow• Instagram: https://www.instagram.com/bigshotshow/ • Harley Finkelstein: https://twitter.com/harleyf • David Segal: https://twitter.com/tea_maverick• Production and Marketing: https://penname.co
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About Big Shot
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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