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Interviews With Entrepreneurs In Eyecare

Interviews with Entrepreneurs in Eyecare

As I consider what fosters and what inhibits my professional growth, one thing that consistently provides value is learning from others. Entrepreneurs learn by doing, and their experiences are unique and invaluable. As someone who values both learning and sharing, I decided to see what professional expertise I might gather to share with the awe-inspiring OWA Connects readers.

These hand-selected entrepreneurs, from a variety of backgrounds, are trailblazers who inspire success by provoking thought and growth. They are respected leaders and mentors, many without knowing so, and they have all graciously shared their knowledge. 

Meet The Contributors

*Please note the links in each person’s description

Founder and Senior Consultant, Spexy “Spexy is the industry leader in optometric training. We equip every position in your office with the tools necessary to produce practice growth and happy patients.“

Founder and Designer, Eye Power “We want to empower kids with vision problems, their parents and Doctors. I am a graphic designer and mom of 4 'eye' kids.”

Co-Founder, Marketing 4ECPs; Speaker, Best-Selling Author, The Digital Sales Rep “The Digital Sales Rep is a practical step by step guide to prospecting and closing sales online. If you are in outside sales, inside sales, or managing a team of salespeople, you want to read this book.”

Founder, Eyeporters “Our passion lies in creating, developing and seeing the fruits of our labor in finished eyewear collections.”

CEO & Founder, ESSIRI Labs, Creator, Eyes Are The Story “We are creating a self-care ecosystem that fuses safe beauty, hormonal health, eye nutrition, ocular hygiene and digital eye awareness — all told through the prism of your ÈYES.”

Gai Gherardi

Co-Founder and Co-Designer, l.a.Eyeworks “We design eyewear to celebrate the diversity of faces and the uniqueness of individuals. The glasses we make are sparks of our imagination. You complete these thoughts and bring the dreams of l.a.Eyeworks into being.”

Founder, OD Perspectives “She is a globally recognized speaker, with a passion for helping optometrists with operations, optical success, contact lens sales and practice management.”

Carrie Wilson, MBA, ABOM, NCLEM, CPHQ

Owner, Optigal Consulting “With a clear mission of helping and inspiring others, I am a proud supporter and developer of the optical industry.  My unique approach of empowerment and simplicity, combined with exceptional guidance and contagious enthusiasm, makes me the perfect choice for helping you reach your full potential.”



How Did You Decide When It Was Actually Time To Take The Plunge And Start Your Own Business?

Kayla Ashlee: When the requests for the trainings I had were becoming so frequent, I knew I had to create another modality for opicals to be able to access my training modules. An online learning library was the solution, and once I realized it was an option, it lit a creative fire in me and it consumed every thought I had when I was awake and in my dreams. I had to take the plunge.

Jessica Butler: We got the idea to start Eye Power after my son was born with a congenital cataract. We saw a need in our online community. Parents wanted their kids to be excited to wear an eye patch. Kids needed to feel special in their glasses. That is when our classic “My glasses give me superpowers” shirt was born. I have a degree in graphic design so I started using my skills to design shirts and it all grew from there. My husband and family were so supportive and I’m so grateful for that. 

Eileen Estrada: It was something I knew I would eventually undertake but it was easy maintaining an employee position. I was challenged by a department restructuring when my child was 2 weeks, it motivated me to focus on building my own business.

What Qualities Are Needed To Be A Successful Entrepreneur? 

Eileen Estrada: Industry knowledge is key, established relationships is equally important. Lastly, I would attribute a successful venture with strategic partnerships and an eagerness to never be complacent with the last sale.

Dr. Jennifer Stewart: Grit, determination, curiosity and a never-ending feel of “what if?”  I also feel that my brain never stops thinking, working, plotting and planning about what my next idea is and how to put it into action.  I never think “can I?; instead I think “how can I make this happen?” and “who can help me?” 

Carrie Wilson: Organization, determination and follow through. All of which I can admit I sometimes struggle with but they are imperative if you want to succeed. Luck, knowledge and talent are much smaller factors in success. 

What Is One Piece Of Advice You Would Give To Someone Who Was Considering Running Their Own Business?  

Jessica Butler: Pick something you love. You will be spending a lot of time, sweat and tears starting your business and you need to love it. 

Eileen Estrada: If you are a sole owner, you should have an experienced sales person or at least one strong established customer relationship. If you know you will need a partner, I recommend having the opposite of your skill sets.  

Amy Gallant Sullivan: Believe in yourself and focus on your mission. Creating, building, launching, maintaining, and growing your business is NOT easy. There will always be a lot of curveballs, detours, doubters, cloudy days, and questions. No matter what, never lose sight of your goal, and do whatever it takes to make it happen. Don’t stop believing.


How Did You Build Your Team? 

Trudi Charest: Like all businesses, staffing can be a challenge. Finding good staff is an art.  As we grew we were able to hire a dedicated Human Resources Manager who has truly taken our recruitment efforts to the modern age. Not only have we built an amazing culture that keeps amazing talent with us, it helps us attract great talent. We started to really share our culture on our social channels and now we find talent is coming to us. Take this tip to your organization and start posting all the fun stuff you do with your teams and the perks and benefits you provide. On top of that we do a lot of internal personal growth training and we post every job opening internally as well as externally. We want to give our employees the chance to progress and move around in our company. Look for what people are good and love to do then help them do that.

Gai Gherardi: We have been fortunate to have worked with an astonishing mix of talented personalities over the years, many of whom have been with us for one, two, or even three decades. We have often hired outside the optical industry because we love the dynamism of people who are engaged with the arts, pop culture, fashion, music, and hospitality. 

What Is Your Favorite Thing About Your Company’s Culture?

Trudi Charest: I have to admit my company’s amazing culture is a lot due to my business partners’ business acumen.  He is very intune to people’s needs and motivations.  Not only do we spend a great deal on internal training and programs to encourage personal growth, we also survey our employees regularly to gauge their satisfaction and hear feedback.  Then we act on it.  

Gai Gherardi: We never take ourselves too seriously.

What’s Your Best Advice On Knowing When To Scale Your Business, And How Much? 

Gai Gherardi: I’m probably not the right person to answer this question as Barbara and our business partner Margo Willits and I have often acted on intuition more than calculation. It’s not easy to “trust your gut instincts” but we are big believers in making space for that kind of deep internal listening.

Dr. Jennifer Stewart: Be honest and know what you can (and should!) take on.  Just because someone else is doing something, doesn’t mean it is the right path for you.  Be authentic, purposeful and define what brings you joy (first)- and then go from there. 

How Do You Narrow Down Ideas To What Will Become The Next Offering Of Your Business? 

Kayla Ashlee: Give the people what they want! We always rely on user feedback and polls. It’s the best way to do business. We recently just sent out our largest poll to our user base for the upcoming summer 2023 releases. There are 6 new courses and mini courses we are launching and we let our users vote on which would be released first. It was confirmation of a great lineup when all the courses got significant votes and were all rather neck-and-neck. 

Jessica Butler: My most favorite part of my business is creating and designing new items. We have had both really great products and others that have flopped but I think the best thing for me is to keep a sketchbook close. Write out ideas and try new things. Listen to your customers and followers on social media and ask them what they want. Interests and needs change so go with the flow and have fun with it.

Carrie Wilson: What does the market need most, what is my turn around time to get it, and what is my return on my investment in time and money.


What Have You Seen That Clinicians Need The Most Help With? 

Kayla Ashlee: Resources. I have seen the greatest opticians work themselves to the bone and burn out because of a lack of resources to build a great team to support the optical. When an optical is in need of a new team member, the greatest opticians begin doing the work of many. Then, when a new hire is added, the leaders are then expected to do the work of many while also training the new hire. This push and pull of keeping the focus on the flow of the optical versus giving the new hire the focused training they deserve is a losing battle. Either the existing team gets burned out because of being overworked or the new hire is pushed off the “training boat” to learn-as-you-go which turns out to be a sink or swim scenario. If they swim they are functioning in their role without the foundational knowledge necessary to be confident. If they sink and fail, it leaves the existing team short handed once again. However, offering resources to provide foundational knowledge in a learning library frees the great opticians of the monotonous parts of the training and allows for the team to all have one foundation to build upon. Furthermore, having a resource for management to have access to the learning portal for leadership training, and tips and tricks that have proven successful in managing other offices, is an invaluable resource. 

Trudi Charest: I have been in eyecare for over 30 years and in many roles where I have been helping practices with their day to day operations and growth so I see it all.  The one thing that never seems to change is the need for assistance in finding great staff.  Staffing is hard.  Finding staff, training staff, motivating and keeping staff all rate the top of any eye care business challenges.  The other is time.  Practice owners wear 20 hats, optometrist, manager, HR, accountant, bookkeeper, marketer, maintenance, payroll and on and on.  They run out of time to spend planning and growing the business.  This is where having a business partner or a great office manager can truly assist in dividing up all the responsibilities leaving time to work on the business instead of in the business.

Carrie Wilson: Learning how to apply knowledge. I have found that many know what they need to, but they don’t realize it, or they don’t know how to get it from their head to a plan they can execute. 

How Has The OWA Helped Your Business?   

Kayla Ashlee: The connections that I have made within the OWA have been nothing short of beautiful. The women I have met have ranged from reps, to CEOs, to inventive entrepreneurs and women who have become pillars of this industry. The mix is fascinating, and I love being able to share our struggles with each other and learn that these women are facing similar challenges. This has an amazing human element that has allowed for connections to happen that I never would have pursued. This often leads to conversations about my business and has made countless touchpoints to expand our reach.

Eileen Estrada: We have been getting lots of exposure in the trade while making connections with other women in the optical industry that have started interesting conversations.

Dr. Jennifer Stewart: Joining the OWA is one of the best things I have done in my career.  The women I have met continue to inspire and encourage me, and the connections and relationships I have made have been instrumental in my success.  I love serving on committees with women from all different companies and roles and learning about what they do – this helps me bring a better message to the optometrists and staff that I present to.  Knowing who you do business with, what their values and goals are and the people behind the company is so important.  The friendships I have made have also been incredible.  I love hopping on a Zoom call to talk “all things optical” with new friends, seeing my connections supporting me in virtual and in person presentations and being able to share the amazing businesses and work these friends do.  I am such a believer in connection- my favorite thing to do is to connect people who I think can work together, and watch them both succeed. 

How Has Having A Woman Owned Business Set You Apart From Those Who Aren’t?

Eileen Estrada: Women are inherently multi-thinkers, our ability to enterprise in various ways helps to our success.

Amy Gallant Sullivan:  Tell me one thing that men cannot live without, daily. How do you explain to male investors or male doctors that most women cannot ‘live’ without eye makeup? At least 60% of women in the United States use mascara daily, and millions of those women suffer from their eye beauty choices. Millions more women have dry eye than men, about two times more women than men. Millions more women have extra-sensitive eyes and their quality of life can be compromised because of this, from their career, to family life, to socializing, and even their self confidence. Being a woman-owned business makes all the difference for this startup because I can relate to what women with sensitive eyes need, from self confidence to beauty. Every day I strive to develop cosmetics for people with extra-sensitive eyes because I understand how debilitating sensitive eyes can be, and also how empowering a non-irritating tube of mascara can make you feel! Men have sensitive eyes too, but, their self confidence and careers aren’t typically impacted in the same way by a tube of mascara. This company concept began with a tube of mascara, and this company could not have been created by a man, as their comprehension of the mission is-just-different. Male eye doctors might understand that some of their female patients cannot use cosmetics but they might not realize how much they suffer with/without. Male investors do not necessarily understand how eye-safe-cosmetics should become an integral part of eyecare protocols and promoted in the general market as not-just-a-beauty-brand. Eyes Are The Story is more than beauty, it is eye wellness. Until “The Story” is known by millions, this book is better written by a woman, even just for empathy alone, as a woman will suffer to be beautiful, inside and out.  


What Was A Challenge You Faced When You First Started Your Business, That You Didn’t Expect?  

Kayla Ashlee: The irony is that in 2019 we had created an online learning resource for opticals. So one would think that we would be perfectly positioned for the dreaded shutdowns and zoom focused, online learning that would take over our society. Well, we were perfectly positioned, but all of the big money in the industry started offering mass amounts of “free” content and webinars. We had a large portion of our starting user base leave to go get “free” learning. Let’s just say I cried a lot, and I’m not a crier. But we kept on creating and sticking to the plan.As it turns out, the saying holds true; ya get what ya pay for. The free content was not nearly up to the standard that our learning library is, and every one of the users came back. No more tears.

Jessica Butler: I think our first biggest challenge was not being prepared for quick growth. We had growing pains for sure. We were featured on the Today Show and many other news outlets. I was not prepared. We sold out quickly and it was a learning experience for sure. That’s not something you can really prepare for or know is coming, but I’m grateful for the experience.

Trudi Charest: It costs a lot of money to run a business.  We worked long hours, did the work of 5 employees until we could afford them and took no pay for the first six months of our operations.  It was tough!  But so worth it.  Everything they say about starting a business is true.  It’s a grind the first few years not knowing if you were going to make payroll every month and pay all your bills but we always made it work.  The biggest challenge was of course was in 2020 when the pandemic hit and we took a huge hit to our cash flow but we came out swinging, got creative and not only made our money back but opened new doors and saw tremendous growth.

Dr. Jennifer Stewart: How quickly a speaking/writing/consulting career would take off!  I have been an industry speaker for the past 10 years, but during COVID I really had the opportunity to increase this with virtual presentations.  In June 2022, I decided to sell my private practice and focus on growing the industry side of my career (and spend more time with my family!) and it has taken off like a rocket!  I have realized I have to carefully consider each opportunity and decide if it supports my vision.  To paraphrase the amazing Bart Foster, from his book “Business Outside”, “if it’s not a heck yes, it’s a no.”  Realizing I can’t be everywhere all the time and participate in everything was tough (I love all challenges!), but it has given me the time and space to focus on what I’m most passionate about.  Although- if it involves a trip to Disney World, I’m likely going to say yes!

How Is Your Business Different Now Than From When You First Began?

Jessica Butler: Eye power has changed a lot in our 10 years. We started with only kids clothing, later adding lots of fun optometry and glasses themed adult shirts, dresses and Christmas ornaments. But 2020 changed everything for our small business. Lots of production problems along with people only spending money on essentials almost killed our little business. It was hard but we learned to adapt. At the end of 2020 we decided to get back into producing products ourselves in our home office. We created a new line of optometry themed ornaments and that winter we grew a lot. Every year since we have grown and now have a line of over 200 eye themed products including jewelry, ornaments and our most popular pen holders. Everything handmade in our small shop in Oregon. 

Amy Gallant Sullivan: Considering that we launched Eyes Are The Story in the United States in 2020 in the middle of a global pandemic, everything is different! Otherwise, during the last 2 years, we have expanded distribution and are now also selling Eyes Are The Story via eyecare specialists in Canada, the United Kingdom, Australia, New Zealand, and France. We have authorization to sell our products in more than 30 countries and have received distribution requests in more than 50 countries!

Carrie Wilson: When I first started, it was a part-time hobby I did just to help other opticians. Now it’s a full-time job that has expanded to fill my days and time. I’m working constantly on something. 

What Is Your Most Memorable Experience Since Starting Your Business?

Trudi Charest: There are so many firsts when you start a business.  Your first client, first employee, first partnership, and the first time you can afford to pay yourself a paycheque!  Those are all memorable but I think the one that sticks out to me the most is when one of our first clients told us that the marketing we were doing for them literally attributed to 30% of their practice growth that year.  There is nothing better to hear than a truly satisfied client.

Amy Gallant Sullivan: We were supposed to launch at Vision Expo East, March 2020. That launch weekend, the Javits Center was turned into a Covid hospital. Needless to say our launch was postponed. Not only did we completely reswizzle our launch and business model to adapt to the global pandemic, but we creatively navigated the news-waves with “The Story”. It was absolutely amazing how ECPs around the world volunteered to help share (and sell) “The Story”. My network of eye doctors and patients eagerly helped me get-the-word-out. Our launch video received almost 1 million views! Eyes Are The Story did not have a store or clinic shelf to sit on, an event, nor party to share samples, but the products popped up in ZOOM calls, FaceBook broadcasts, LinkedIn testimonials, Insta, Twitter… all over social media. My global village of eye docs activated and helped me launch. And, the best part, for the first four months, I was working from the sofa in my parents’ loft in Boston, as I could not fly home due to travel restrictions! My parents were incredible, helping me navigate the pandemic uncertainty, but also supporting me with food and lots of coffee during my 18+ hour workdays. 

Gai Gherardi: I’m lucky in that there have been quite a few “most memorable” experiences over the past 43 years, but I was thinking recently about the time Barbara McReynolds and I were asked to make 3-D glasses for a multimedia production of Philip Glass’ opera “Monsters of Grace” in 1998. The experience of looking from the front of the house to see everyone in the audience of 1,800 people wearing our design was truly extraordinary. 


How Do You Try To Remain Unique In The Space Of Your Competitors?  

Amy Gallant Sullivan: Eyes Are The Story is the World’s first optocosmetics and skincare brand specifically created and clinically-proven safe for sensitive eyes and skin, dry eyes, and contact lens wearers. There is a lot of noise on the market for products that are purportedly Eye-Safe, but, are not. As we are blurring the lines between Pharma and Beauty, and it is imperative for the Eyes Are The Story brand to set the marketing and education straight with correct science-based evidence and verified Eye-Safe products. Leveraging knowledge from some of the world’s leading ocular surface disease specialists and collaborating with state-of-the-art laboratories in the United States, Canada, and Italy, we are innovating new formulations that no other brand has ever envisioned nor produced.

Gai Gherardi: We don’t think of that much. We have known all along that being true to ourselves and our interests, and keeping our lights turned up bright in a spirit of sharing was going to be our path to full freedom of expression.

How Do You Stay Motivated? 

Dr. Jennifer Stewart: Coffee!   I am super routine and goal focused, and always have been.  I start my day (every day!) with a workout, and then look to my to-do list.  I have short and long term goals, and am always working towards these (and adding new!)  I also listen to my mind and body- if I have a day where I’m just not feeling it, I take the cue to do a lower impact workout (yoga or a long walk) and maybe switch gears to a project that isn’t as intense.   

Carrie Wilson: I’m usually internally motivated but when my motivation meter drops the people I work with really help — Scott Balestreri, Bradie Husser, Alex Peng, the leaders of Laibach & York are phenomenal at supporting me in everything I do.


First Job: 

Kayla Ashlee: Nanny.

Jessica Butler: Target.

Trudi Charest: Receptionist in an optical store.

Eileen Estrada: Retail sales at 13, but I started my career at Popular Club Plan as a Merchandise Coordinator in shoes.

Amy Gallant Sullivan: When I was still in high school, my first paycheck actually came from translation work I did for my father, Dr. David A. Sullivan, and his laboratory at Schepens Eye Research Institute/Harvard Medical School. I translated 100-year-old research from French to English. It was definitely an eye-opening experience!

Gai Gherardi: Selling tickets at a folk music nightclub called the Golden Bear that opened with the controversial comedian Lenny Bruce. We were closed down for “obscenity” every night by the police. I always consider Lenny Bruce my college education. 

Dr. Jennifer Stewart: Wrangler at a riding stable.

Carrie Wilson: I worked in our family bait shop making lures, digging up earthworms, catching minnows and working the register. I was 6 years old. 

Biggest Role Model: 

Kayla Ashlee: Cinderella. I identify with her struggles and perseverance because of certain aspects of my childhood. She taught me that gentle love and genuine kindness display unusual strength that makes all the difference in society.

Jessica Butler: My parents who both own their own businesses.

Trudi Charest: My dad. He was an Optician who owned his own optical store so I literally grew up in the business. He was one of the hardest working people I have ever known and the nicest. He was always about helping other people be successful.

Eileen Estrada: My first optical mentor Joyce Pokoy Kurtulus, one of the best product design and innovators in the industry. She has been instrumental in my growth and continues to be an inspirational force in my career.

Amy Gallant Sullivan: My parents. 

Gai Gherardi: Curiosity!

Dr. Jennifer Stewart: I have a small group of OD’s in private practice that I text with every day (even weekends!)  They continue to motivate and inspire me with the practices they have created.  They are also an amazing sounding board for my many many industry ideas and give great feedback! 

Carrie Wilson: My mom. She is the strongest woman I know. 

Recommended Book: 

Kayla Ashlee: The Gifts of Imperfection by Brene Brown.

Trudi Charest: The Digital Sales Rep  (duh…of course I am going to recommend my best selling book).

Eileen Estrada: The Alchemist by Paulo Coelho.

Amy Gallant Sullivan: The one I’m going to write. 🤓 Or … the Fannie Farmer Cookbook. I cook to destress!

Gai Gherardi: The Creative Act: A Way of Being by Rick Rubin.

Dr. Jennifer Stewart: I’m a speed reader so I tend to read 2-3 books a week.  Connect with me on Goodreads!  I love reading anything thriller/mystery, personal growth/development and business! 

Carrie Wilson: Professionally, mine of course! But my personal interests are probably boring for most since they tend to lean toward history and psychology. I’m currently reading a local history book. 

One Thing That Makes You Smile:  

Kayla Ashlee: Many things make me smile. That’s just me. But the thing that makes me laugh hysterically is videos when men get scared and let out the most high pitch scream! OMG it’s the funniest!

Jessica Butler: My kids.

Trudi Charest: Funny cat videos.

Eileen Estrada: Inspiration, finding a nugget that makes my mind swirl with ideas and concepts.

Amy Gallant Sullivan: Waking up every day.

Gai Gherardi: Kindness.

Dr. Jennifer Stewart: My family!  My husband and two sons (10 and 7) bring me so much joy.  Also, living by the beach is magical.

Carrie Wilson: Hearing my kids laugh.

Most Productive Time Of Day:

Kayla Ashlee: Weekday mornings after I have had a kick-butt early morning workout.

Jessica Butler: Evenings after 7pm. I’m a night owl. 

Trudi Charest: 5am  (I am an early bird.  I get up, get my coffee, read all the industry news and feel ready for the day)

Eileen Estrada: Mornings!

Amy Gallant Sullivan: Sunrise.

Gai Gherardi: Mornings in summer; nights in winter. 

Dr. Jennifer Stewart: 8-11am.  I tend to block this time off and don’t schedule meetings unless I absolutely need to.  This is my best time for writing, thinking, working and planning.

Carrie Wilson: Late at night. 

Favorite Glasses-Wearing Celebrity:  

Kayla Ashlee: Robert Downey Jr.

Trudi Charest: Elton John.

Amy Gallant Sullivan: Amal Clooney.

Gai Gherardi: I adore the character Little Enid from Daniel Clowe’s cult classic graphic novel “Ghost World”.

Dr. Jennifer Stewart: Kayla Ashlee of Spexy 🙂

Carrie Wilson: I honestly don’t pay much attention to celebrities but my favorite glass wearing character is Penelope Garcia on Criminal Minds. Her wardrobe stylist is excellent.  


I would like to thank each interviewee for taking the time to share their experiences. Links to each person’s LinkedIn and/or business website can be found in the summary at the beginning of this article.  

What was your favorite take-away from this article? Let us know in the comments below!

Interviews performed and written by: Carissa Dunphy

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