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Big Shot

Big Shot

By: Big Shot
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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.Big Shot Economics Leadership Management & Leadership
Episodes
  • From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After Another

    From Paramount to Fox to Expedia: How Barry Diller Built One Massive Business After Another
    May 21 2026

    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.

    —

    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

    (28:20) Why he still feels like he hasn’t made it

    (30:00) Building the Fox network and bringing Rupert Murdoch on board

    (34:06) How he took control of IAC

    (38:07) The story behind buying Expedia

    (40:47) Barry’s leadership philosophy

    (41:37) M&A strategy at IAC

    (44:43) How Eastern European Jews built Hollywood

    (47:36) Barry’s relationship to Jewish culture

    —

    Where To Find Barry Diller:

    • Website: https://www.iac.com/leadership/barry-diller

    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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    49 mins
  • The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff

    The Quiet Dealmaker Who Bought the Warriors and A’s | Lew Wolff
    Apr 30 2026
    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.—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 (42:54) Buying and selling his stake in the Golden State Warriors(45:46) The kind of work he enjoys and what he credits for his success(50:42) The story behind Moneyball(54:19) Why he stays focused on the future(55:20) Why he prioritizes relationships over profit(58:57) How he handled negative press as owner of the A’s(1:03:48) How the Giants blocked the A’s from building a new stadium(1:08:59) How he learned to let things go(1:12:51) Lew and Bud’s attempt to integrate their fraternity(1:15:07) His thoughts on Jewish entrepreneurship(1:18:38) 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
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    1 hr and 21 mins
  • The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph Schaffer

    The 104-Year-Old Godfather of the Shmatta Industry Who Turned $1,800 Into Billions | Joseph Schaffer
    Apr 9 2026

    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:

    (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

    (35:20) 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
    Show More Show Less
    37 mins
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