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“Helping Marginalized Women Feel Comfortable In Their Own Skin Literally And Figuratively” With Lia Winograd

“Our brand mission of inclusivity goes beyond making better-fitting garments for our underserved audience: we also want to broaden…


“Our brand mission of inclusivity goes beyond making better-fitting garments for our underserved audience: we also want to broaden opportunities for the women making them. One of my primary goals in entrepreneurship is to expand the possibilities available to emerging Hispanic business leaders in both the US and Latin America. Pepper could not have made it this far without the relationship I built with a female-owned, sustainable manufacturing firm in Medellin, where I’m originally from.”


I had the pleasure of interviewing Lia Winograd, the co-founder of Pepper, the first body positive bra company for women with small chests. Pepper raised over $90K in revenue from a Kickstarter campaign and website pre-orders in 2017. Previously, Lia worked as a consultant at McKinsey all over Latin America and later helped to scale a B2B technology startup in NYC. On top of building Pepper, she is pursuing her MBA at NYU Stern School of Business.

Thank you so much for doing this with us! What is your “backstory”?

My grandfather, a Polish Jew, fled Europe as a child before the Holocaust. He didn’t speak a word of Spanish when he stepped off the boat in Colombia, but got by on the generosity of Jews who had migrated ahead of him. After dropping out of high school to support his younger brother, he spent decades working his way to the top of a button factory and — later, as its owner — transformed it into a successful business that provided for my family and generations to Come. My grandfather’s story inspired me to become an entrepreneur someday. I always knew I would be a business owner, but never thought it would be a bra company!

The idea of Pepper came together about a year ago when my coworker and I were talking about how badly our bras fit. Bra prototypes, we found out, are typically manufactured using a mold that’s based off of a woman with an “average” bust (36C), and then those designs are shrunk down to smaller sizes. However, since the initial designs are made with a different shape of breasts in mind, it creates numerous fit issues for women with less breast tissue, including falling straps, digging underwires, and, most significantly, a bra gap. So her and I began working after hours and weekends (we both had a full-time job) to create Pepper, not just to meet the needs of an underserved, $4B U.S. market, but to help marginalized women feel confident in their own skin. We’re on a mission to “close the gap” for small-chested women, both literally and figuratively.


Can you share the funniest or most interesting story that happened to you since you started your company

We wanted to follow a very lean methodology when we launched Pepper, so we created our MVP (minimum viable product), which in retail means a sample. We partnered with a Colombian factory and developed our initial prototypes out of a drawing that we drafted (no designers were involved at this stage). The sample that the factory sent to us was about 70% of the way there, but we figured we’d pause, launch the Kickstarter campaign, and assess whether there was enough traction before going down a rabbit hole of investing thousands of dollars into a product that no one wants. Our campaign ended up being a total success! Almost immediately after, we sprinted to USPS to send the bra samples back to Colombia so our manufacturer could continue working on them.

Five days passed… then ten… then fifteen… and there was no word from the shipment. It ended up being that the bra samples (the ONLY ones we possesed) got stuck in Colombian customs and had somehow disappeared. My co-founder and I freaked out for a total of two minutes. We had just launched this successful campaign and we no longer had a product; we had to start from SCRATCH all over again. But we took this as an opportunity: we re-assessed EVERYTHING, from the manufacturing partner we were working with, to the smallest details on the bra. It was a blessing in disguise because we made a much better product because of this.

What do you think makes your company stand out? Can you share a story?

Last November, we were selected to interview at Y Combinator. Jaclyn and I packed our bags and booked a next-day flight to San Francisco. After five hours of flight time, a 45 minute taxi to Mountain View, and close to three hours of wait time for Michael Seible to call us in, we interviewed for a total of TEN minutes. After that was over, we headed back to San Francisco, where one of our Kickstarter backers picked us up in her car and took us to a coffee shop. She had contacted us after backing our campaign and wanted to eagerly share her story growing up small-chested. She explained the ridiculous pressures she grew up with to look “curvier”, because in today’s society, having more curves somehow conveys your sexuality as a woman. Jaclyn and I listened and took notes. What makes Pepper stand out is our commitment to build a community of women to change the status quo, and turn these customer insights into must-have products. We have an exciting opportunity to help this underserved market in the bra industry. As more companies start to expand into plus sizes, we’re going towards the opposite end of the size spectrum at an affordable price.


None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I’ve been incredibly lucky to receive so much help and mentorship from other founders in New York, networks from previous jobs, and MBA professors, alumni and fellow students. The latest example of generosity I experienced was from a team of two women who recently founded a branding agency called Zoe Pepper. Micki and Cynthia both have vast experience in advertising with major retailers like Nike, and in our meeting we quickly came to the conclusion that Pepper was still too small to partner with them. Instead of moving on and calling it a day, they decided to go above and beyond to help us anyway, at no cost. They hired PhD’s to conduct a market sizing analysis and set up a pro-bono, one-hour long strategy session to help us get started. If there’s one thing I know for sure it’s that I will be working with them in the future once Pepper makes it big.

Are you working on any exciting projects now?

We’re currently developing a new, wire-free bra style. While our customers love the benefits of the All-You bra — in particular that they can fill its cups — through extensive customer discovery interviews we learned that women need a variety of styles to serve different functions. Wire-free bras offer greater comfort, and, if they are made to fit correctly, can create seamless support and shape. Why is making this important? From a survey we conducted with 841 customers who identified as small-chested, we learned that 69% don’t want push-up bras and would prefer to look natural and 85% can’t fill the cups of their bras and get a gap. With products that finally fit, we hope to redefine body standards.

How have you used your success to bring goodness to the world?

Our brand mission of inclusivity goes beyond making better-fitting garments for our underserved audience: we also want to broaden opportunities for the women making them. One of my primary goals in entrepreneurship is to expand the possibilities available to emerging Hispanic business leaders in both the US and Latin America. Pepper could not have made it this far without the relationship I built with a female-owned, sustainable manufacturing firm in Medellin, where I’m originally from.

We chose our manufacturer because of their commitment to social responsibility. We are proud to share that our manufacturing partner:

● Generates employment opportunities on the “oriente antioqueño” rural areas, where single mothers or “head of household” have preference during the selection process.

● Offers an Employee Fund Program to provide credits and savings benefits to their employees

● Is gold certified from WRAP, the world’s largest independent certification program focused on the apparel, footwear, and sewn products sectors. WRAP has a zero tolerance policy on child labor, forced labor, and inhumane treatment.

● Recycles more than 76% of fabric residue

It’s important to us as a business that we’re partnering with socially and environmentally responsible manufacturers. It’s good for small boobs, and it’s good for the planet.


Do you have a favorite book that made a deep impact on your life? Can you share a story?

Lean Startup. While it sounds basic, it has really changed the way we operate and think about growth. Founder’s Dilemma helped me as I was navigating those tough conversations with my co-founder about our vision, equity split, and long-term goals.

What are your “5 things I wish someone told me before I started my company” and why. Please share a story or example for each.

Don’t start solo. It’s tempting to want to keep 100% of a company and have full control over strategic decisions. But finding a co-founder is your first proof point that your idea is powerful enough to bring someone onboard.

Throw perfection out the window. Pepper launched on Kickstarter with a sample that wasn’t even 100% ready. Be scrappy and lean. You don’t want to waste years working on something only to realize no one wants it.

Network that network: When you’re creating something new, there is not one single person that’s going to have all of the answers for you. But the more people you talk to, the more information you start collecting and you start fitting all the puzzle pieces yourself. Don’t shy away from reaching out to people and putting your idea out there.

You haven’t really made it until you make it. Get ready to spend the next five to ten years building out a company. It doesn’t happen overnight. Just because we were successful at launching a Kickstarter campaign, it doesn’t mean we’ve “made it”. There are so many endless challenges ahead.

Have fun! Starting a business can be stressful, but there’s no downside to learning how to build something out from scratch!


Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

Hayley Barna! She is able to incorporate her past entrepreneurial experience from Birchbox, good and bad, into her outlook on investing. She’s genuinely interested in helping founders.

This was very inspiring. Thank you so much for joining us!

If you would like to see the entire “5 Things I Wish Someone Told Me” Series In Huffpost, Authority Magazine, ThriveGlobal, and Buzzfeed, click HERE.

Originally published at medium.com

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