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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