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!

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In This Episode We Cover:

(00:00) Intro

(02:47) Stephen’s childhood in Detroit

(05:15) Lessons and inspiration from his grandfather and uncle

(17:00) Stephen’s rocky start in Florida and struggles in school

(22:35) How Stephen got into the University of Michigan and became a good student

(27:13) How getting fired sparked his first business

(34:40) Early business goals and the fundraising hurdles that led to bootstrapping

(41:10) Stephen’s diversification strategy

(44:01) How Stephen found great people to work with

(47:30) What Stephen loves about the real estate business

(49:12) Why the 90s market wasn’t ready for CityPlace

(54:12) The story behind Hudson Yards and the Olympic stadium that fell through

(57:50) Why Stephen says his latest project will be the most impactful

(1:04:15) How to maintain momentum while building large projects

(1:08:32) What it was like buying the Miami Dolphins

(1:17:05) Why he brought F1 to Miami

(1:19:25) Stephen’s philanthropy and why giving back is important

(1:23:40) What drives Jewish excellence in business and giving(1:26:00) How he built and maintained a relationship with his daughters

(1:34:00) How he survived a tough time in the 90s

(1:35:37) AI's impact on the future

(1:37:10) Advice for young entrepreneurs and how he values relationships

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• David Segal: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://twitter.com/tea_maverick⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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