Lia Winograd, Pepper: Designing a Perfect Fit

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This blog post was written by Ellie Gershenwald (Steinhardt '22) based on an interview with September 2022 Founder of the Month Lia Winograd (Stern '19), Co-Founder and Co-CEO of Pepper

Pepper is a body positive e-commerce company that makes better fitting bras for small-chested women.

Growing up in Colombia, Lia Winograd was exposed to entrepreneurship from an early age. Her grandfather, an immigrant from Poland, had dropped out of high school and worked his way up to owning a button factory to support his family. His story and determination inspired her to take risks and start her own company. 

Lia attended Tufts University where she pursued a degree in Economics and International Relations. After graduating in 2012, she was offered a job at McKinsey & Company as a consultant, but decided to take a 6 month gap to join a startup accelerator in Brazil where she learned about different startup models and worked on building a startup in the legal space. Following the program, she joined the McKinsey team in Colombia and worked there for a few years before moving to New York. In New York, Lia worked at Conversocial, a tech startup, where she ended up meeting her Pepper co-founder, Jaclyn Fu. 

Lia and Jaclyn both struggled to find bras that fit properly and comfortably. Knowing that there was an unrepresented category of women who are not the central piece in the design process, they decided to take matters into their own hands. The co-founders launched Pepper as a Kickstarter campaign in April 2017 with their classic “All You” bra, which was created specifically for women with small chests. In under 2 weeks they had overwhelming support, reaching over 950 backers and more than quadrupling their initial $10,000 fundraising target. Seeing this success, Lia applied to MBA programs to access more resources that would allow her to accelerate the company and she was accepted into the full-time program at NYU Stern

Lia immediately focused her NYU journey on opportunities that were relevant to growing Pepper. Lia took advantage of the NYU Entrepreneurial Institute’s resources as a participant in the Startup Sprint, a two-week customer discovery and mentorship intensive, and as an attendee at countless networking events and workshops. As Pepper has continued to grow, her most valuable takeaway has been the importance of staying in touch with customers to help shape the future strategy of the company. During the Sprint, she was able to meet Nobu Nakaguchi (Tisch ‘10), Co-Founder of Zola, and hear his advice that one of the most important goals as a founder is to make yourself invisible. This resonated with her because founders are typically involved in every decision, but being able to step away is key because it means you are making the right hiring decisions. She participated in the Stern Venture Fellows program through the NYU Stern Berkley Center for Entrepreneurship where she was able to expand her network of founders and investors. In 2018, Pepper raised a pre-seed round with participation by the NYU Innovation Venture Fund

Since graduating from NYU, Lia has been named to Forbes’ 30 Under 30 list for Retail & Commerce and Inc.’s Female Founders 100 list. This recognition along with her numerous programs and experiences have provided access to valuable connections through networking. 

Looking back, Lia reminisced about her most rewarding moment along her journey as a founder: building Pepper’s supply chain in Colombia. It had always been a very special mission for her to give back to the community where she grew up, so visiting the factory there a few months ago for the first time since before Covid was incredibly impactful. She noted how exciting it was to see how much the operation had grown and to learn that Pepper has generated over 200 jobs in Colombia.  

Lia remains committed to providing perfect solutions for women with smaller chests. With the goal of owning the closet for every woman in the target size range, she looks forward to tapping into other categories in the future. 

When asked what advice she has to share with aspiring founders, Lia recommended starting small and testing demand as much as possible using creative avenues that do not require a lot of funding and emphasized the importance of allowing startups to grow first without growing the team.