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: 

—

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

Harley Finkelstein and David Segal are back with Season 3 of Big Shot! Today, we chat with beauty industry icon Bobbi Brown. Known for her work as a makeup artist, Bobbi’s expertise has been showcased on the covers of leading magazines, including Cosmopolitan, Allure, Mademoiselle, and Teen. She’s the author of nine beauty books, with five achieving bestseller status.

In 1991, Bobbi founded Bobbi Brown Cosmetics, which Estée Lauder acquired for $74.5 million four years later. Bobbi had a 25-year non-compete with Estée Lauder, and as soon as that expired, she launched her latest company, a clean beauty brand called Jones Road.

In our conversation, we discuss the following: 

—

In This Episode We Cover: 

(04:28) How Bobbi got started by cold-calling models and agencies 

(10:30) How Bobbi learned entrepreneurship skills at Emerson 

(12:52) Bobbi’s first lipstick and the beginnings of her makeup empire

(17:39) The Bergdorf Goodman deal that almost fell apart

(21:30) A chance encounter in an elevator that led Bobbi to her second chemist

(22:10) Meeting Jeff Zucker’s grandmother and landing a regular spot on The Today Show

(26:15) Trailblazing the natural makeup movement 

(34:10) Bobbi’s meeting with Leonard Lauder of Estée Lauder

(35:59) How Bobbi was able to prioritize her kids 

(39:20) The sale to Estée Lauder 

(42:54) How Bobbi celebrated and shared her wealth with her family 

(43:45) The first freestanding store, and how Leonard Lauder supported Bobbi

(47:00) The decline of Bobbi’s relationship with Estée Lauder that led to her leaving 

(51:30) The Just Bobbi curated collection at Lord and Taylor 

(53:30) How Bobbi moved on from the drama at Estée Lauder 

(1:00:01) Launching Jones Road

(1:08:55) Miracle Balm’s instant popularity

(1:10:20) Bobbi’s response to a TikTok influencer trashing her foundation 

(1:13:43) Bobbi’s thoughts on selling her new company 

(1:14:45) Bobbi’s partnership with her son, Cody

(1:17:03) New learnings at Jones Road

(1:18:28) Bobbi’s thoughts on chutzpah

(1:19:25) Bobbi’s perspective on health and longevity

(1:20:36) What being Jewish means to Bobbi 

(1:23:15) The secret to Bobbi’s successful marriage and partnership

—

Where to find Bobbi Brown:

X: https://x.com/justbobbibrown

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

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

TikTok: https://www.tiktok.com/@justbobbibrown

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 sit down with the Chairman of the Board and Chief Executive Officer of G-III Apparel Group, Morris Goldfarb. Morris took over running his father’s company at the age of 24. His journey is deeply rooted in the inspiring legacy of his father, Aron Goldfarb, a Holocaust survivor who immigrated to the U.S. and founded G-III in 1956. Morris has transformed the company from a small women's leather outerwear business into a global fashion powerhouse, managing brands like DKNY, Calvin Klein, and Tommy Hilfiger. In our conversation today, talk about:

—

In This Episode We Cover: 

(01:50) Morris’s childhood in Israel and New York 

(04:42) Morris’s dad, Aron Goldfarb’s memoir about the Holocaust, Maybe You Will Survive

(08:54) How Morris was affected by the Holocaust survival stories of his family and friends

(10:20) Aron Goldfarb’s clothing business and why he wanted Morris to get a city job

(12:36) How Morris took over the family business at the age of 24

(14:30) Morris’s ambition and early years expanding G&N Sportswear

(16:05) Morris’s consulting and building factories in South Korea

(19:59) G-III’s journey to going public 

(22:40) Why Morris had to pivot the business in 1995 and move towards licensing 

(31:50) The current state of G-III

(32:52) How Morris fought nepotism working at his father’s company

(34:17) Acquisitions that grew G-III

(38:18) An explanation of how licensing works at G-III

(40:18) The pitfalls of direct to consumer businesses 

(42:26) Morris’s thoughts on licensing vs. owning brands

(43:24) Morris’s partnership with Carl Banks 

(46:30) Morris’s family life and what it’s like working with his son

(50:53) Why G-III is not a great fit for most emerging brands

(52:50) What made Morris finally feel like he’d made it

(54:29) What chutzpah means to Morris

(54:55) Morris’s philosophy on giving back and why he built a Jewish cemetery in Poland

(59:18) Why Jews have made so many contributions to business, science, and academia 

—

Where to find Morris Goldfarb:

Website: https://ir.giii.com/management/morris-goldfarb

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

When you think about a "convenience store manager," you probably don't imagine a future billionaire. But that's exactly the path Ron Shaich took from humble beginners selling Tollhouse cookies to a $7.5 billion restaurant empire. In this episode of Big Shot, Harley Finkelstein and David Segal welcome Shaich, the founder of Panera Bread, who shares his incredible journey from a nonprofit convenience store to his pivotal decision to create Panera Bread. Ron is a master at finding the trends others can't see before becoming popular.  He shares the challenges and successes that defined his path, highlighting the power of adaptability and innovation. And breaks down the difference between risk-taking and risk-avoidance, and how leaning into one over the other can lead to incredible success.

The episode is filled with incredible takeaways, including:

—

In This Episode We Cover: 

(02:35) Ron’s early years growing up in New Jersey in a family of left-wing political activists

(07:50) Ron’s gap year working for a congressman 

(09:45) How a false accusation of shoplifting prompted Ron to open a convenience store

(14:50) How Ron fell in love with business and his time at Harvard Business School

(19:28) The rewards of entrepreneurship 

(20:40) What business has in common with politics

(23:22) How Ron made money selling flea collars in college 

(26:00) Why Ron got his inheritance early

(27:35) Ron’s work in DC as President of Targeting Systems

(29:08) How Ron opened The Cookie Jar in Boston

(31:43) Ron’s partnership with Au Bon Pain’s founder, Louis Kane

(39:44) Ron and Louis’s exceptional friendship and partnership

(42:25) The importance of empathy and the insights that it brought Ron

(48:35) How Ron created a brand new category, bakery cafe

(51:50) How Ron felt right before Au Bon Pain’s IPO

(53:00) The downsides of going public

(54:50) Ron’s means, ends, and by-products framework

(57:20) What Ron learned from watching his parents face death

(1:00:13) How Ron organized his life 

(1:03:35) Ron’s purchase of the St. Louis Bread Company 

(1:07:28) How Ron’s trend studying led him to fast casual dining

(1:13:52) The transformation of St. Louis Bread into Panera 

(1:15:33) Why Ron decided to sell Au Bon Pain to focus on Panera

(1:20:25) The rapid growth stage of Panera 

(1:22:51) Ron’s philanthropy with No Labels and Panera Cares 

(1:25:14) The painful journey of transforming Panera 

(1:32:09) Thoughts on success, chutzpah, and the Jewish entrepreneurial spirit

(1:34:28) Why entrepreneurs are risk avoiders 

(1:35:34) Why Ron sees building organizations as a way to impact the world positively

(1:37:44) Ron’s investment company, Act 3, and the problem with short-termism 

—

Where to find Ron Shaich:

Website: ⁠https://www.ronshaich.com/⁠

LinkedIn: https://www.linkedin.com/in/ronshaich/

X: https://x.com/shaich

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

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 sit down with Wall Street titan Leon Cooperman. The son of working-class Polish immigrants and a first-generation college graduate, Leon founded Omega Advisors after a successful 25-year career at Goldman Sachs, where he rose to become Chairman and CEO of Goldman Sachs Asset Management.

Despite being one of the richest men on the planet, Leon lives modestly, even still changing his own lightbulbs.

In this fascinating conversation, he shares insights on achieving success in business, marriage, and family, along with his philosophy on giving back, inspired by the belief that "a man's net worth is measured not by what he earns but by what he gives away." Leon even gets political and shares his thoughts on former President Trump. We can’t wait for you to listen.

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: 

(05:34) Leon’s background growing up in the Bronx

(07:36) Why Leon quit dental school and switched to economics

(09:28) How Leon got 16 job offers after graduating and why he went with Goldman Sachs

(11:00) Why Goldman Sachs was so successful 

(12:35) How Leon’s father reacted to him dropping out of dental school

(13:25) Leon’s promotion to partner at Goldman Sachs

(15:30) Why Lee says he never learned how to live rich 

(17:58) Leon’s philanthropy and why it’s so important to him

(19:51) Leon’s thoughts on protestors at Columbia 

(25:58) Why there are many significant contributions to humanity made by the Jewish people

(29:30) Why Leon left Goldman Sachs and founded Omega

(33:10) The rogue employee that caused Leon to be accused of insider trading

(36:20) Why Leon considers Henry Singleton brilliant

(42:52) What Leon loves to do 

(43:57) Leon’s hands-on approach to philanthropy 

(46:17) Why Leon went to Xerox out of college(and why he left to go back to school) 

(50:15) Leon’s successful marriage and his big takeaway

(51:45) Why Leon stuck it out with Goldman Sachs for so long

(53:25) Lessons from William Hurt and Teddy Roosevelt

(54:40) Why Leon changes his own lightbulbs in spite of his arthritis

(55:37) How Leon raised his kids to be self-starters 

(57:00) David Rubenstein’s recent purchase of the Orioles

(57:57) Leon’s 40 businesses 

(59:25) What chutzpah means to Leon and the importance of respect

(1:00:15) Leon’s thoughts on capitalism as an equalizer 

(1:04:41) Leon’s political views 

(1:06:02) Why Leon would never vote for Trump

(1:07:01) Leon’s father and the impact he had on him

(1:09:10) How Leon chooses institutions to donate to

(1:10:45) How Leon handles setbacks

(1:12:35) Why Leon thinks the country isn’t at its best 

(1:13:40) Leon’s thoughts on AI

(1:14:22) Leon’s mother and her impact on him

(1:15:36) Why it’s common for Jewish people to have a fallback plan

(1:17:35) Advice on investing 

(1:21:05) How Leon evaluates companies

—

Where to find Leon Cooperman:

LinkedIn: https://www.linkedin.com/in/leon-cooperman-8ab35024/

Book: From The Bronx To Wall Street: My Fifty Years in Finance and Philanthropy: https://www.amazon.com/Bronx-Wall-Street-Finance-Philanthropy/dp/1642256226

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 sit down with another legendary real estate developer, Larry Silverstein. Best known for the 99-year lease he signed for the World Trade Center, just six weeks before 9/11, Larry’s story is one of persistence and strategic partnerships—and a whole lot of chutzpah. He shares with us today how he leveraged partnerships, refurbished properties on a shoestring budget and built a business that today is valued at over $10 billion. As with many successful Jewish entrepreneurs, family is at the center of it all, and Larry speaks with extreme gratitude about his children and wife Klara. You won’t want to miss hearing about how Larry very narrowly missed being at ground zero during 9/11, and how his wife supported his efforts in rebuilding the World Trade Center. 

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: 

(03:19) How Larry got established in real estate with no money

(09:59) Why Larry turned down a 100k profit on his first contract 

(12:51) How Larry leveraged investors to land million-dollar properties

(14:22) The low-budget, resourceful way Larry’s team refurbished buildings

(16:31) How Larry collaborated with competitors in purchasing 711 Fifth Avenue

(24:42) Coca-Cola’s purchase of 711 Fifth Avenue

(26:43) Why Larry worked with partners

(27:33) The beginning of Larry’s journey toward buying the World Trade Center

(35:22) How Silverstein Properties built their own electric plant 

(45:28) The drama of signing Salomon Brothers 

(52:44) Larry’s accident and acquiring the World Trade Center

(58:45) Why Larry was absent from the building on 9/11 

(1:00:20) How Larry decided to rebuild the World Trade Center

(1:04:21) When Larry knew he made it

(1:06:28) Larry’s philanthropic efforts paying the tuition of medical school students

—

Referenced: 

Harry Helmsley: https://en.wikipedia.org/wiki/Harry_Helmsley

711 Fifth Avenue Purchased from Columbia Pictures: https://www.nytimes.com/1978/04/23/archives/realty-news-fifth-avenue-third-avenue-executives-named.html

George Kaufman’s obituary: https://www.nytimes.com/2018/02/26/obituaries/george-s-kaufman-who-revived-astoria-studios-dies-at-89.html

Peter Feinberg obituary: https://www.nytimes.com/1990/03/15/obituaries/peter-i-feinberg-79-real-estate-developer.html

Port Authority to lease World Trade Center to Silverstein Properties: https://www.panynj.gov/port-authority/en/press-room/press-release-archives/2001_press_releases/port_authority_toleaseworldtradecentertosilversteinpropertiesinc.html

World Trade Center history: https://www.911memorial.org/learn/resources/digital-exhibitions/world-trade-center-history

Ed Koch: https://en.wikipedia.org/wiki/Ed_Koch

Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers

Mortimer Zuckerman: https://en.wikipedia.org/wiki/Mortimer_Zuckerman

Salomon Will Move to the World Trade Center: https://www.nytimes.com/1988/11/29/nyregion/salomon-will-move-to-trade-center.html

The Collapse of Drexel Burnham Lambert: https://www.nytimes.com/1990/02/14/business/the-collapse-of-drexel-burnham-lambert-key-events-for-drexel-burnham-lambert.html

NYU School of Medicine Offers Full-Tuition Scholarships to All New & Current Medical Students: https://nyulangone.org/news/nyu-school-medicine-offers-full-tuition-scholarships-all-new-current-medical-students

—

Where to find Larry Silverstein: 

Silverstein Properties: https://www.silversteinproperties.com/

The Rising: The Twenty-Year Battle to Rebuild the World Trade Center: https://www.amazon.com/Rising-Twenty-Year-Battle-Rebuild-Center/dp/0525658963

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 honored to host business mogul Peter May. But his path to managing more than $7 billion is not what you might expect. What started as a career as an accountant at the prestigious KPMG quickly became something much different once Peter crossed paths with Nelson Peltz, igniting a dynamic partnership that spanned decades. Together, they founded Triarc Companies and pioneered innovative funding strategies, revitalizing numerous struggling businesses. They eventually sold the company and founded Trian Partners, a multi-billion dollar investment firm. Peter's commitment to philanthropy extends beyond financial contributions, as he invests his time and expertise. Notably, his impactful work with Mount Sinai Health Systems and Operation Exodus showcases his dedication to making a difference. Join us as Peter generously imparts invaluable insights and practical wisdom applicable to all aspects of life.

In This Episode We Cover:

(07:28) What it was like growing up during the Cold War in Long Island

(12:12) How his father was a great role model

(14:33) Peter’s time at The University of Chicago

(16:25) How Peter was inspired by his father’s saying, “Do more than what’s expected of you”

(22:24) The Jewish value of education

(24:53) How Peter was able to avoid being drafted to Vietnam

(30:59) Getting started as an accountant at KPMG

(32:40) How Peter met Nelson Peltz

(34:24) The importance of adding value

(36:11) The origins of Home Depot

(38:16) How Peter and Nelson Peltz went into business together

(41:00) When Peter and Nelson took their company public

(44:25) What happened after Peter and Nelson sold Flagstaff foods

(49:20) Peter and Nelson’s funding strategy emerges

(50:42) How MPM group consulting got its start

(51:57) What constructive capitalism is

(54:10) How Peter and Nelson bought Triangle Industries

(1:00:29) How Peter and Nelson transformed Triangle and made it profitable

(1:03:18) The purchase of America Can and National Can

(1:17:03) The meaning of Nelson’s phrase “I’d rather be rich than right”

(1:18:53) Why Peter doesn’t look back much

(1:20:14) Why chutzpah is so quintessential to the Jewish entrepreneurial experience

(1:22:23) Why Peter doesn’t feel like he’s made it still

(1:23:30) About “engaged philanthropy” and how Peter helped turn around Mount Sinai Health

(1:30:15) Peter’s advice to the next generation

(1:33:26) About Operation Exodus

(1:36:33) Peter’s legacy—

Referenced:

Green tea benefits: https://www.firebellytea.com/blogs/all/green-tea-benefits

Firebelly Tea: https://www.firebellytea.com/

The University of Chicago: https://www.uchicago.edu/en

Pogroms: https://encyclopedia.ushmm.org/content/en/article/pogroms

Nelson Peltz: https://www.forbes.com/profile/nelson-peltz/

Arthur Anderson: https://en.wikipedia.org/wiki/Arthur_Andersen

KPMG: https://kpmg.com/

Emerson Radio: https://www.emersonradio.com/

Bernard Marcus: https://en.wikipedia.org/wiki/Bernard_Marcus

Mike Milken: https://en.wikipedia.org/wiki/Michael_Milken

Saul Steinberg: https://en.wikipedia.org/wiki/Saul_Steinberg

Victor Posner: https://en.wikipedia.org/wiki/Victor_Posner

Alcoa: https://www.alcoa.com/global/en/home/

Mount Sinai Health System: https://www.mountsinai.org/

Engaged philanthropy: https://engagedgiving.org/philosophy

Operation Exodus: https://operationexodususa.org/

—

Where to find Peter May:

Mount Sinai Health: https://www.mountsinai.org/about/board-leadership/peter-may

Wendy’s: https://www.wendys.com/who-we-are/board-directors/peter-may

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