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“Absolutely Nothing That Someone Could Have Told Me Before Would Have Prepared Me For This” with Orit Hashay

I had the pleasure to interview Orit Hashay the CEO + Founder, of Orit is a serial entrepreneur with over 15 years of experience in software and business development. Prior to starting Brayola she was an investment manager at Carmel Ventures and founded Israel’s most successful wedding platform,, which she coded herself.

Yitzi: Thank you so much for doing this with us! What is your “backstory”? (If you share an inspirational or aspirational backstory, we will be able to publish this interview in Thrive Global as well)

As the CEO of Brayola, I have dedicated myself to solving real problems facing women today and simplifying the process of finding the perfect bra through crowdsourced algorithms and a data system.

I founded Brayola when I was pregnant, my body was changing, and bra shopping was the last thing I wanted to do. With my background in software development, I knew I could make bra shopping easier for myself and for women like me. That’s what inspired me to start Brayola — I wanted to make bra shopping a more enjoyable experience for all women.

Brayola became the first online lingerie shop to match women with bras based on their personal sizes, tastes and styles. To date, our algorithm has analyzed more than 50 million data points shared by women!

Yitzi: Can you share the funniest or most interesting story that happened to you since you began leading your company?

The most interesting thing that has happened to me during my time at Brayola was actually the process of raising funding while trying I was pregnant with my son. As a woman pitching to (mostly male) VCs about the woes of bra shopping, you need to have both guts and patience. Men don’t necessarily know the frustrations that bra shopping can bring, so being persistent and unafraid of shocking the audience helped me get through the initial hesitation that came with pitching a technology targeted specifically to women.

Yitzi: So how exactly does your company help people?

Brayola takes the pain out of bra shopping for millions of women by using advanced algorithms that match women with the perfect bra in every size and brand. On, shoppers can shop the largest inventory of bras and intimates in the world — both luxury and commercial brands — from cup size A to N with prices ranging from $10 to $1,000 dollars.

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

First and foremost our goal with Brayola was to provide women with bras that fit them, regardless of shape or size. It can be difficult for a woman to shop for bras, heading in and out of stores trying on different styles and fits, with the same results, a bad fit and in turn, low body confidence. Brayola helps you feel beautiful no matter what by using algorithms and data from other women to ensure you find a fit that makes you feel great.

Additionally, at least once a month I try to be present at different conferences and speaking opportunities, because I believe it is important to inspire other women to start their own companies, become founders, and to fear nothing.

Yitzi: What are your “5 Things I Wish Someone Told Me Before I Became CEO” and why. (Please share a story or example for each.)

  1. I would like to say number one is that absolutely nothing that someone could have told me before would have prepared me for this.
  2. There is never enough time in the day, and you could always use more sleep, but it’s all worth it in the end.
  3. No matter how many skills you have, or how many new skills you learn each month, you’ll always need to learn something new in order to run a different aspect of your business.
  4. You need to wear every set of pants, and not be afraid to get your hands dirty.
  5. Being a CEO is a beautiful thing, it’s a learning process that never ends.

Yitzi: I have been blessed with the opportunity to interview and be in touch with some of the biggest names in Business, VC funding, Sports, and Entertainment. 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, or I might be able to introduce you.

I know we can only say one…but I’m going for two! I would love sit down with Albert Einstein and Mahatma Gandhi. This quote always stays with me “First they ignore you, then they laugh at you, then they fight you, then you win.” This is an amazing ethos to remember when building a company, and it has proved to be very true for me now that I am running Brayola.

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