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:

(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

(43:58) Lessons from William Morris’s shortcomings that shaped CAA’s DNA

(48:25) How Michael signed every member of Saturday Night Live 

(50:45) The story of Michael’s first client and first big stars

(59:55) The story behind Janklow and Nesbit and what Michael likes about Silicon Valley

(1:02:28) Michael’s true talent 

(1:06:40) How Michael and Andy Grove envisioned streaming before Hollywood was ready

(1:10:20) The ripple effects of streaming across entertainment

(1:17:02) 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

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:

(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

—

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

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:

(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

(05:01) Why Don trusted his intuition and took a chance on developing swampland in Florida

(09:04) How Don got the governor of Florida on board to green light his project

(11:00) Early influencers: How Don leveraged the power of celebrities 

(14:25) Building Aventura Mall

(19:27) Don’s common-sense approach 

(21:52) Don’s relationship with his father 

(24:00) Why Don says it’s terrible to run a family business

(25:11) Don’s current roles and how he set his kids up 

(27:01) Don’s explanation for the success of the Jewish people 

(29:37) A dinner with Frank Sinatra 

(31:44) Advice for young Jewish entrepreneurs 

(33:37) Where Don got his confidence and conviction 

(35:06) How Don saved the Pittsburgh Mall after the excavator destroyed private property 

(37:50) Don’s thoughts on when to sell and when not to

(40:05) Don’s friendship with Tony Bennett 

(41:21) How to cultivate strong business relationships

(43:49) Don’s advice to future generations of Soffers 

(45:52) Why Don still thinks Florida is a good place to develop 

(46:42) 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

Bobby Kotick built a $69 billion empire from scratch—and the story is even crazier than it sounds.

In this episode of The Big Shot, we sit down with gaming’s ultimate entrepreneur. Bobby takes us from hustling snacks at baseball games to building one of the most iconic tech companies in the world: Activision Blizzard. Hear how he cold-called Nintendo, got investment from Steve Wynn on a private jet, took over a bankrupt video game company, and turned it into an empire that Microsoft bought for $69 billion.

In this episode, you’ll hear about:

• Bobby’s early hustles: selling ashtrays, snacks, and party access in NYC

• Dropping out of college after Steve Jobs told him to

• Starting a dorm room company with Howard Marks

• Convincing Steve Wynn to invest $300K after a chance meeting

• Reviving Activision from bankruptcy using old IP and grit

• Why Pitfall and River Raid were billion-dollar blueprints

• How Activision became the first American Nintendo licensee

• The Apple boardroom showdown with John Sculley

• Turning Activision into a media empire: Call of Duty, Candy Crush, and Guitar Hero

• What it felt like selling the company to Microsoft for $69 billion

• His philosophy on leadership, loyalty, and building an enduring business

—

In This Episode We Cover:

(00:00) Intro

(03:19) Selling ashtrays at playdates: Bobby’s first hustles

(06:39) Shadowing NYC real estate legends like Larry Silverstein

(09:59) Dorm room hardware startup with Howard Marks

(13:18) Inventing a typewriter-printer hack and launching via Byte magazine

(16:38) Meeting Steve Jobs

(19:58) Why Steve Jobs tells Bobby to drop out of school

(23:17) Getting featured in Forbes and making his parents panic

(26:37) The wild story of meeting Steve Wynn at a Texas cowboy gala

(29:57) The legendary $300K check in the basement of a casino

(33:16) Trying to sell to Apple (and the cigar moment with Sculley)

(36:36) Licensing games for EA and learning to be scrappy

(39:56) Black Monday, the Amiga, and a failed bid for Commodore

(43:15) Buying 20% of Nintendo’s U.S. licensing agent

(46:35) Discovering Activision buried inside a bankrupt company

(49:55) Why Bobby wanted to bring Pitfall and River Raid back to life

(53:14) The $400K move that changed gaming history

(56:34) A childhood connection saves the Activision bankruptcy deal

(59:54) Turning a bankrupt company into a profitable one in months

(01:03:13) Raising $40M and going on an acquisition spree

(01:06:33) How Bobby became the longest-serving tech CEO

(01:09:53) The Toy Story game meeting that cemented Bobby’s role

(01:13:12) Why Bobby never wanted to run a business that lost money

(01:15:32) Reflecting on the Microsoft acquisition and legacy

—

Where To Find Bobby Kotick:

• X: https://x.com/bobbykotick 

• LinkedIn: https://www.linkedin.com/in/bobbykotick/

—

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

In today’s episode of Big Shot, we sit down with Mike Milken—legendary financier, philanthropist, and chairman of the Milken Institute.

Mike has been a driving force in medical research, public health, and education for over five decades. Fortune called him “The Man Who Changed Medicine,” and Forbes listed him among “Visionaries Reimagining Our Children’s Future.” 

Mike’s financial innovations helped launch industries like cable TV, homebuilding, and cellular technology. Beyond finance, he has led major philanthropic efforts, including the Prostate Cancer Foundation, FasterCures, and the Milken Center for Advancing the American Dream, set to open this year. A signatory of the Giving Pledge, he has committed much of his wealth to driving global impact.

In our conversation today, we talk about: 

• The childhood moments that shaped Mike’s curiosity and deep empathy

• How Mike mastered mental math through Holocaust survivor, Jakow Trachtenberg's technique

• How speech and debate sharpened Mike’s ability to communicate big ideas

• The impact of the Watts riots on Mike’s career path 

• How market crashes in 1974 and 1987 provided opportunities for significant gains

• Mike’s take on regulations and why he remains relentlessly optimistic about the free market

• A glimpse into Mike’s philanthropic work in medicine and education

• And much more!

If you'd like to apply to be an executive producer, please complete the form here https://shorturl.at/xLQUW

—

In This Episode We Cover:

(00:00) Intro

(02:25) Why Mike has been involved in philanthropy from such a young age

(09:57) Early experiences that shaped Mike’s radical empathy 

(19:03) How Mike learned mental math by using the Trachtenberg system 

(20:25) Mike’s journey to Berkeley and interest in the space program

(28:40) How the Watts riots impacted Mike

(33:40) The value of doing research, and what Mike learned about credit

(38:10) Mike’s first investment bank job 

(44:50) How Mike was able to fund MCI at a time when AT&T had a monopoly 

(50:22) How the 1974 stock market crash impacted investment banking 

(57:50) The culture of outsiders dominating Hollywood—many of them Jewish

(1:00:59) The stock market crash of 1987

(1:03:58) Why the best investors are social scientists

(1:06:15) The cultural shift that brought down big tobacco 

(1:09:20) Takeaways from Mike’s interview with Elon Musk

(1:11:00) The JPL Mars Rover landing simulation and how free enterprise drives innovation

(1:14:09) Milken Community School, and Mike’s emphasis on health and medical research

(1:16:22) How views on nutrition and the microbiome have evolved

(1:19:48) Mike’s advice: prioritize great people and be flexible 

(1:24:30) Private equity’s impact on business and the downside of family businesses

(1:28:40) The Miken Center for Advancing the American Dream

—

Where To Find Mike Milken:

• X: https://x.com/MilkenInstitute

• Instagram: https://www.instagram.com/milkeninstitute/

• Facebook: https://www.facebook.com/milkeninstitute/

• Website: https://www.mikemilken.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

In this episode of Big Shot, we’re thrilled to welcome the legendary marketing visionary Lynda Resnick. As the co-owner of The Wonderful Company, Lynda has shaped iconic brands like POM Wonderful, Wonderful Pistachios, and FIJI Water into household names.

With her husband, Stewart, Lynda also turned The Franklin Mint into a cultural sensation and brought fresh ideas to the floral industry with Teleflora’s innovative, long-lasting gifts.

Join us as Lynda takes us on a journey through her extraordinary life—from her early days as a child actor to her recent retirement and her hands-on efforts to make communities healthier and stronger through impactful philanthropic initiatives.

• How Lynda built a successful business at the age of 19

• Turning The Franklin Mint into a cultural icon and making millions with a deluxe Monopoly game

• The incredible story of branding POM Wonderful and FIJI Water

• How she sold $150 million worth of Monopoly 

• Lynda’s commitment to quality 

• Why she’s never raised any outside capital 

• The childhood experience that shaped Lynda’s decision to always self-fund her philanthropy

• A life-changing epiphany inspired by philosopher Michael Sandel

• Lynda’s philanthropic work building healthier, safer communities for her workers

• The role Judaism plays in her life, her marriage, and advice for young people

• And more!

—

In This Episode We Cover:

(00:00) Intro

(02:35) Lynda’s early years in Pennsylvania

(05:14) Lynda Limited, the company Lynda founded at the age of 19

(08:37) Lynda’s activism and her involvement with the Pentagon Papers

(13:06) Thinking inside the box

(15:35) How Lynda reinvented the floral business with Teleflora

(19:00) Taking The Franklin Mint beyond coins 

(24:00) The story of buying Jackie O’s pearls and making reproductions

(25:30) Why Lynda and her husband Stewart bought land in the Joaquin Valley

(28:58) How Lynda discovered the benefits of pomegranate 

(30:20) Building the Pom Wonderful brand, including the packaging

(32:18) Early obstacles Pom Wonderful faced, including the court battle 

(34:00) Why Lynda insisted on 100% pure pomegranate juice

(35:25) How Lynda was able to build brands around commodities

(39:11) The story about acquiring Fiji 

(43:27) Lynda’s philanthropic philosophy 

(45:10) Lynda’s epiphany inspired by Michael Sandel

(49:10) Lynda’s philanthropic work building better communities for her workers 

(52:50) Lynda’s experiences with antisemitism, including rejection from The Campfire Girls

(54:43) The role Jewish culture plays in Lynda’s life 

(56:07) Lynda’s time as a child actor—and an early lesson on always being prepared

(58:23) Lynda’s advice on staying true to your values

(59:10) How Lynda and Stewart have maintained their strong marriage and partnership

(1:02:40) Lynda’s thoughts on building lasting brands

(1:03:55) AI’s answer to what Lynda’s superpower is

(1:06:00) How “America’s Favorite Mom” got overshadowed by a golf game

(1:09:04) Why Lynda doesn’t have regrets

—

Where To Find Lynda Resnick:

• Website: https://www.wonderful.com/

• LinkedIn: https://www.linkedin.com/in/lynda-resnick-04103a101/

—

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

In this special episode of Big Shot, recorded live at the iconic Kennedy Center in Washington, D.C., we’re joined by Uri Levine, the co-founder of Waze. Uri is a visionary entrepreneur whose journey includes building Waze, the world’s largest community-based traffic and navigation app, which Google acquired for over $1 billion. Beyond Waze, Uri has co-founded several impactful startups like Moovit (acquired by Intel), FeeX, and Engie. He’s also the author of Fall in Love with the Problem, Not the Solution, a must-read guide for entrepreneurs.

In our conversation today, we cover: 

• Lessons on failure and prioritization from Uri’s father

• A clever hack he used to pitch Waze with an incomplete product

• The cultural drive behind the Jewish ambition to create positive change

• The story of the many millionaires created by Waze’s acquisition

• And so much more!

A special thank you to ADL In Concert Against Hate. You can learn more here https://www.adl.org/adl-concert-against-hate-shines-light-heroes

—

In This Episode We Cover:

(00:00) Intro

(01:40) How Uri’s father taught him the importance of failure

(04:55) A story about prioritization

(06:59) Uri’s solution for fundraising with an incomplete product

(09:00) The ups and downs of the start-up journey

(11:04) Why Jewish people are drawn to entrepreneurship and making a positive impact

(12:58) The connection between the kibbutz community and entrepreneurship

(13:25) The Google acquisition of Waze 

(13:58) The importance of keeping the main thing the main thing 

(15:11) How tikkun olam inspires Uri’s entrepreneurial ventures 

(16:48) Chutzpah and the Israeli experience 

(17:40) How Uri continues to be inspired by his father

—

Where To Find Uri Levine:

• LinkedIn: https://www.linkedin.com/in/uri-levine/

• X: https://x.com/urilevine1

—

Where to Find ADL:

• Website: https://www.adl.org/

—

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

In today’s episode of Big Shot, we’re joined by Mindy Grossman, former CEO of Weight Watchers, who led the company’s transformation into a global wellness brand. Like many of our past guests, Mindy’s journey involves perseverance, bold decisions, and calculated risk-taking.

Mindy’s remarkable career began with a surprising choice—dropping out of college. She then worked up to executive roles at Polo Ralph Lauren, Nike, the Home Shopping Network, and Weight Watchers. In our conversation today, we cover: 

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In This Episode We Cover:

(00:00) Intro

(02:33) Mindy’s early years as an adopted child of working-class Jewish parents

(06:00) Why Mindy quit school and moved to New York 

(09:00) Mindy’s first job as an Executive Assistant 

(11:40) Mindy’s mantra, “passion, purpose, and impact”

(12:42) How Mindy landed her first sales role

(15:06) Bashert vs. self-determination

(15:44) The importance of calculated risk-taking

(17:26) Why Mindy left Tommy Hilfiger for Ralph Lauren

(20:40) The success of Mindy’s new category, main floor

(24:00) Why Mindy resigned from Ralph Lauren

(25:10) How Ralph Lauren retained Mindy by creating a new role for her

(26:50) Mindy’s time as CEO of Polo Jeans 

(28:44) “Intrapreneurship” and the excitement of working with visionaries

(31:30) Founders and boards Mindy works with 

(32:40) Mindy’s time at Nike and why she left Polo Jeans

(37:05) Mindy’s pitch to Barry Diller and her position at Home Shopping Network

(45:31) Reviving the culture at HSN

(50:10) The huge impact Mindy made on employee morale by buying new chairs

(52:18) The “There’s no place like HSN” campaign 

(54:40) The magic moment that affects human behavior to get a sale 

(57:11) Taking HSN public

(1:04:39) Meeting Oprah and joining Weight Watchers

(1:08:19) Mindy and Oprah’s arena tour 

(1:09:10) How Mindy kept Weight Watchers customers connected during the pandemic

(1:12:25) Mindy’s shift to private equity and advising

(1:18:30) Mindy’s thoughts on Jewish success 

(1:21:00) The death of her parents and the legacy of belief Mindy passes down 

—

Where To Find Mindy Grossman:

• X: https://x.com/mindygrossman

• Instagram: https://www.instagram.com/mindygrossman

• LinkedIn: https://www.linkedin.com/in/mindy-grossman

—

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

In today’s episode of Big Shot, we’re joined by retail legend Mickey Drexler, whose transformative leadership reshaped some of the biggest names in fashion.

Over his 18-year tenure at The Gap, Mickey took the company from $400 million to $14 billion in revenue, revolutionizing casual wear and spotting a new retail opportunity that led to the creation of Old Navy.

His influence extends far beyond The Gap—he also founded Madewell, served on Apple’s board for over a decade, and now works alongside his son Alex on the growing success of Alex Mill. In our conversation today, we cover: 

—

In This Episode We Cover:

(02:53) Welcome Mickey Drexler

(03:29) Mickey’s childhood in the Bronx

(12:40) The traits Mickey looks for in people he’s hiring

(14:56) Why Mickey values kindness and treating others fairly, regardless of their status 

(16:40) Why the best training is doing the job

(18:40) Mickey’s high standards, obsession with data, and the importance of instinct 

(28:39) How Steve Jobs persuaded Mickey to join Apple’s board

(32:33) What Mickey admired about Steve Jobs

(34:20) Why a bad decision is better than indecision

(36:34) What makes a great website

(39:43) Mickey’s process for helping The Gap standout

(46:32) Why Mickey calls the fashion business a commodity business

(47:20) How Dayton Hudson’s Target stores inspired Mickey to build Old Navy

(54:15) How Mickey got the name for Old Navy

(57:42) The challenges Mickey faced opening Old Navy 

(1:00:20) How the meaning of value depends on the individual customer

(1:05:29) The call from Steve Jobs that marked an end to Mickey’s time at The Gap

(1:11:20) Mickey’s wife, Peggy’s background

(1:13:22) Mickey’s experience taking J. Crew private

(1:18:17) How Mickey balances work and family 

(1:20:03) Mickey’s thoughts on Jewish entrepreneurship, especially in the fashion industry

(1:21:52) Mickey’s parting advice on learning entrepreneurship thoughts on school

(1:23:37) What David learned at school, and Harley’s learnings from Mickey

Where To Find Mickey Drexler

• X: https://twitter.com/millarddrexler

• Instagram: https://www.instagram.com/mickeydrexler

• LinkedIn: https://www.linkedin.com/in/millard-mickey-drexler-1b00a9269/

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

In this special live episode of Big Shot, recorded at StartupFest, we are excited to welcome Heather Reisman, the trailblazing entrepreneur behind Indigo Books & Music. Heather's remarkable journey began as a single mother learning to code to support her children.

Fueled by grit, a bit of luck, and a talent for connecting with extraordinary people, Heather built Indigo into Canada’s largest bookseller. However, Heather's ambitions extend beyond her role as founder and CEO. She is also a devoted wife, mother, grandmother, and philanthropist, having contributed $100 million to the University of Toronto and supported various causes through her foundation, HSEG, which aids the education of lone soldiers after their service in the IDF. In today’s conversation, we talk about: 

—

In This Episode We Cover:

(05:08) Welcome Heather Reisman

(05:35) What it was like growing up in the Reisman household

(10:26) Heather’s experience working at her mother’s retail store

(11:15) Heather’s early passion for books

(12:44) Why Curiosity is the key to everything

(14:00) Heather’s coding journey as a single mom

(16:00) Why Heather quit her job after an undeserved demotion 

(17:00) Heather’s time working at a consulting firm

(19:00) Co-founding Paradigm 

(19:56) Heather’s thoughts on change and why she left consulting

(24:29) Why Heather left Cott 

(26:55) Heather’s depression and the book that kickstarted the next chapter of her life

(20:24) The Borders deal that never worked out

(33:00) Raising $25 million and founding Indigo 

(37:19) The story of acquiring Chapters 

(39:45) Integrating Chapters

(42:13) How the ‘New Coke” failure inspired Heather to keep Chapters and Indigo separate 

(43:20) Why Heather founded an e-reader company called Kobo

(48:47) Selling Kobo to Rakuten for $315 million 

(50:19) The power of Heather’s Picks

(52:13) Taking Indigo private

(53:00) Heather’s literacy goals and the importance of curation

(57:00) How Heather balances work and family life

Where To Find Heather Reisman:

X: https://x.com/heatherreisman

Instagram: https://www.instagram.com/heatherreisman

Facebook: https://www.facebook.com/hreisman

LinkedIn: https://www.linkedin.com/in/heather-reisman-3bab2319

TikTok: https://www.tiktok.com/discover/heather-reisman-indigo

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