Jaclyn Pascocello of HEYWEAR on Hospitality Foundations, Financial Missteps, and Redefining Optical Accessibility

As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Jaclyn Pascocello, CEO of HEYWEAR.

Jaclyn Pascocello is the CEO at HEYWEAR, a walk-in optical studio where you can get an exam and prescription eyewear in minutes without an appointment or vision insurance. Jaclyn has spent her career in hospitality, leading the development of operational strategy across industries from large scale restaurants to experiential retail. Prior to HEYWEAR, she was a founding member and COO of Spacious where she was integral to the launch of a network of drop-in workspaces that utilized otherwise wasted real estate in urban cities like New York and San Francisco.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

My path was not necessarily linear and was marked by a lot of quick decision making, mistakes and listening to my gut. I grew up in the hospitality industry and learned all of what I believe about service by working in restaurants. It was there that I began to learn how to read people, understand human behavior, wear multiple hats at the same time, create memorable experiences and think on my feet. That period of my life was invaluable and created a foundation of skills that translated really well into building businesses, probably because of the similarities in the everyday having a lot of unknowns. Working in early-stage companies with moving goals can be incredibly challenging and require a lot of strategic decision making just like managing a busy Saturday night rush.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

HEYWEAR is changing the way that people get prescription glasses in a way that has never been done before in the United States. We’ve created an all-in-one product and service that removes the high cost and complicated process of purchasing prescription eyewear and instead makes eye health and eyewear more accessible. HEYWEAR Studio is our first walk-in optical studio where you can get a new Rx and prescription eyewear in 30 minutes. Our goal is to make HEYWEAR a brand and organization really focused on taking all the mystery and intimidation out of caring for your eyes before there is any sign of a problem. The cost of vision insurance and traditional eye exams (not to mention frames) has made eye care and eyewear a luxury and we want to change that. For less than $200 you can get multiple pairs of eyewear (sun or clear!) and a comprehensive screening in one visit.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I had spent my teenage years working in restaurants which always made me feel happy and at home. When I was just out of school, I had gotten it in my head that working in finance would mean I had “grown up.” That said, I got my first job on Wall Street and realized very quickly that it did not fuel my passion or purpose, which was to create experiences that make people happy. I laugh now when I think back to my younger self thinking that I had it all figured out or that being “grown up” was a destination that I would magically find. I realize now that the most grown-up decision I would come to make was taking big risks and following my passion. While it was the first of many missteps, I am grateful for that time as it really made me see what I was meant to do with my life.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

I am lucky to be surrounded by so many amazing women in my life. When I think of my mentors, I do think of those I look up to but also the women who raised me and those who have worked beside me in some capacity and have taught me more than I think they ever realized. I am grateful for the people in my life who believe in me and lift me up when I need it most.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I would say that disruption can sometimes be used as a buzzword and slapped on shiny new things that operate differently than we have seen before but might not actually change the status quo. That doesn’t do justice for all the amazing products and services that have been created out of a desire to disrupt something, particularly in a way that makes them available to larger populations whether it’s because of cost, location, technology, or reach. That’s the kind of disruption I get excited about — the type that truly impacts accessibility.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

Don’t waste time focusing on what other people think of you.

Be the best version of you, not somebody else.

Be grateful for a mundane day.

We are sure you aren’t done. How are you going to shake things up next?

We are in the early stages of growing HEYWEAR and are excited about how we will expand and continue to evolve as an organization. They say when you are building a business you are never done, and I truly believe that. Right now, my main focus is expanding HEYWEAR to reach as many people as possible to really make an impact on the accessibility of approachable eyecare and eyewear. We believe that vision is a human right, and we want to ensure that we play a big part in making that a reality.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

It is hard to answer this question because it is basically everything! Women have always been faced with incredible challenges. Whether it is the narrative of not being able to “do it all,” pay inequality or the pressures of living in a male-dominated society, women are faced with a constant uphill battle. While this is challenging, it is a true testament to the strength of women, whether in everyday life or in creating new paths to lift themselves and others up around them.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

I read the Alchemist for the first time when I was young and during a formative time in my life. I always revisit it when I feel lost or at a crossroads. The main lessons are that we should always follow our own path, listen to our hearts, be grateful for each day and realize the learnings in failure. This has always had a significant impact on my thinking in life.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Just start somewhere and start small! You never realize the impact of acts of kindness in everyday life. Be a good one and pass it on.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Mine is simple and it stems from something my mom used to say to me when I was little and admittedly still says to me to this day, specifically before big life moments: ‘Be the best Jaclyn.’ Or in other words, be the very best version of yourself, not a copy of somebody else. We all have our strengths and opportunities, and it is important to know what you love doing and what you bring to the table and be the very best version of that person.

How can our readers follow you online?

I spend the majority of my time when I am away from the office either on a Peloton or cooking with my family — things that help me rejuvenate from a demanding work schedule. I really prefer connecting directly with people and am always excited to hop on a zoom, join a book club, ride together (JaclynNY), or just exchange emails. LinkedIn works well for connecting online!