From College Dropout to Running Polo, Nike, Weight Watchers, and HSN | Mindy Grossman

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:

• X: https://x.com/mindygrossman

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

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

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