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MPWEntrepreneurs

‘We talk ourselves out of it’: Entrepreneur Emma Grede never second-guesses herself

Sasha Rogelberg
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Sasha Rogelberg
Sasha Rogelberg
Reporter
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Sasha Rogelberg
By
Sasha Rogelberg
Sasha Rogelberg
Reporter
Down Arrow Button Icon
October 13, 2026, 5:19 PM ET
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Emma Grede said she was able to develop her keen sense of cultural relevance by not second-guessing herself.Rebecca Greenfield—Fortune
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Entrepreneur Emma Grede attributed her ability to keep brands relevant to her complete assuredness in her intuition, which was honed in the expanses of her triumphs—and failures.

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“I don’t second-guess myself,” she said at the Fortune Most Powerful Women Summit in Santa Barbara on Tuesday. “I think a lot of us have that skill, but we talk ourselves out of it, and we second-guess ourselves a lot. One of the most expensive habits that we have as women is waiting until we’re ready.”

Grede told Most Powerful Women editorial director Ellie Austin that she has fine-tuned the ability to try something out and has failed so many times that “it stopped mattering” and doesn’t hold her back. The 44-year-old entrepreneur, who was raised by a single mother in East London and never went to college, is the cofounder and chief product officer of $5 billion shapewear company Skims, as well as an investor and fashion designer, most recently founding Off Season, a luxury sports-fashion brand, alongside designer Kristin Juszczyk.

Grede’s intuition is what led Skims to release a series of unexpected products, including a push-up bra with a raised nipple detail. Initially seen as provocative, the bra actually serves the purpose of affirming women who have gotten breast reconstruction surgery after a mastectomy, Grede said. While some products like black thongs are meant to meet a demand for the many women who don’t possess one, others, like a face sculpt wrap, are meant to create, occupy, and own a new market.

“One of my special sauces is to go in and say, ‘Well, how do you take a problem that exists within this and make it make sense for a new generation of customers?’” Grede said.

“So much of what I do is not brain surgery,” she added. “It’s about making things 1% better. It’s about taking existing markets, but really paying attention and really being focused on the excellence of products.”

Grede has worked to share her insights with other women, including in her book Start With Yourself: A New Vision for Work & Life, warning that too much advice to other women is feel-good, rather than practical and effective.

“What I’m not doing is trying to make people feel comfortable,” she said. “I’m talking about the reality of what I do, and so I actually think that so much of what’s out there, specifically in women’s media, is to make women feel better. 

“And I’m interested in that because I’m a results-oriented person. I’m an operator, and so I talk about the truth and the quality it is to operate in my life. I’ve never been shy about saying this is what I had to do. These are the sacrifices that I had to make. These are the tradeoffs in my life. These are the things that I don’t do.” 

Fortune Daily breaks the traditional barrier between audience and newsroom. The show transforms Fortune’s trusted reporting into actionable, conversational, and entertaining insights for an emerging class of business leaders. Watch here.
About the Author
Sasha Rogelberg
By Sasha RogelbergReporter
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Sasha Rogelberg is a reporter and former editorial fellow on the news desk at Fortune, covering retail and the intersection of business and popular culture.

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