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.
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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
(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
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*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
