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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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
