Big Shot

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: 

• Why Mindy dropped out of college and the value of risk-taking 

• Mindy’s impact on Nike as the most senior woman executive

• The importance of rooting out toxic employees in your organization

• How Mindy revived the culture and inspired employees at HSN

• Taking Home Shopping Network public 

• Meeting Oprah, their arena tour, and keeping Weight Watchers alive during the pandemic

• Mindy’s sales philosophy, move to private equity, thoughts on family and the Jewish success story, and much more!

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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 

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Where To Find Mindy Grossman:

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: 

• Mickey’s humble beginnings in a one-bedroom apartment in The Bronx
• Mickey’s heuristic for hiring and what draws him to people
• Mickey’s friendship with Steve Jobs and what it was like serving on each other’s boards
• The importance of urgency and why a bad decision is better than indecision
• How Mickey does market research, and his process behind both The Gap and Old Navy
• Mickey’s thoughts on entrepreneurship, his family, and much more!

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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

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: 

• Heather’s childhood and how her working mother influenced her
• The importance of curiosity and how this value has served Heather in entrepreneurship
• Heather’s first startup, Paradigm
• Heather’s work at Cott and how she broke out of a mental funk after leaving
• Raising $25 million and founding Indigo
• Founding Kobo eReaders and selling to Rakuten for $315 million
• Heather’s life beyond work and plans for increasing Canada’s literacy

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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:

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: 

• How chutzpah and optimism landed Bobbi her first Vogue cover

• How Bobbi developed her first lipstick and the original ten that became the brand’s foundation.

• How organic networking was a big part of Bobbi’s success

• The Estée Lauder acquisition of Bobbi Brown Cosmetics and Bobbi’s friendship with Leonard Lauder

• How Bobbi prioritized motherhood over work

• Life after the non-compete: Her new partnerships and Jones Road

• And so much more

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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

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Where to find Bobbi Brown:

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:

• The emotional impact of being the son of a Holocaust survivor

• Morris’s strategies for growing the family business and taking it public

• The setbacks G-III faced in 1995 and how Morris was able to successfully pivot the business

• Brand acquisitions and licensing that became the bread and butter of G-III

• Morris’s life outside work, including family and philanthropic accomplishments

• And much more!

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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 

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Where to find Morris Goldfarb: