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! — 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

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If the walls of Kosher delis could speak, they would (schm)ooze invaluable wisdom and endless laughs. Harley Finkelstein (Shopify) and David Segal (DAVIDsTEA) are Jewish entrepreneurs influenced by the greats who came before them. But, they realized no one was archiving the best behind-the-scenes stories ever told. Before time was up, they set out on a passion project to preserve the memories, mishaps, and wins of the people who have seen it all. Big Shot tells the stories of the people that shaped an entire generation.