She has been referred to as the "woman who dresses America," and for 26 years, Jenna Lyons did just that as she worked her way up the ranks at J.Crew—and we gladly followed every stylish move. In fact, we’d go as far as to say that her rule-breaking style single-handedly changed the landscape of fashion and design forever.
But now she’s stepping into a new role—and a new industry—as a beauty entrepreneur. As the co-founder of LoveSeen, a new direct-to-consumer line of faux lashes designed for everyday wear, the fashion icon is bringing her penchant for thoughtful design and talent for making trends accessible to the $532-billion beauty industry.
Below, Lyons tells Create & Cultivate all about her new venture and impressive career, including how she coped with the uncertainty after ending her 27-year tenure at J. Crew, what she thinks it really takes to be successful in any industry, and why she believes you should always hire people who are smarter than you.
How did you make your first dollar and what did that job teach you that still applies today?
I made my first dollar babysitting. I think even at the age of 15, I cared about leaving the kitchen clean, tidying up the living room, and being on time. I remember distinctly when I turned 16, I got a car, and with my newfound sense of freedom, I went out on a Friday and lost track of time. I completely missed my babysitting gig, and they never hired me again. I quickly learned the consequences of not showing up and the value of other people's time, not just my own.
Leaving a job is always scary and the higher up you are, the harder the fall. So, how did you move past that fear of not knowing what’s next after J.Crew and not having the answers?
I don’t think I did. I was scared, worried, and unsure. I did not move past the fear, I had to sit with it. It was a hard first year. It was like leaving a family, and a sense of security that I had known for more than two decades. I knew I would work again somehow, but not knowing was in some ways a welcome change, having been at the same company for such a long time.
Take us back to the beginning—what was the lightbulb moment for your new business, LoveSeen, and what inspired you to pursue this path?
In my last couple of years at J.Crew, I noticed many of the women were coming into the office wearing eyelash extensions. And not just because they were getting married or going to an event, but because it was a Tuesday. Separately, I was consumed by YouTube videos of women doing incredible makeup tutorials with seven layers of contour, three different highlighters, and the final touch was always an eyelash. I found it incredibly interesting that the two different ends of the spectrum in terms of beauty desires were focused on the same thing. I thought there had to be something in between. Having no eyelashes myself, I'm super aware of how transformative they can be. I became obsessed and met some partners who put a business plan together, and here we are.
Entrepreneurship is all about taking calculated risks. What’s the most pivotal risk you’ve taken, and how did it change your path?
Mostly, this idea that all of this would work at all. Having an idea is just that; an idea. Until you've put it out there in the world you really don’t know whether or not it’s going to work.
What career mistake has given you the biggest lesson?
Careful what you wish for. There was a time in my career when I wanted to be more senior and have more control over the business, and then it happened. While I don’t regret the process, I didn't realize how hard it would be. How many mistakes I would make, and how many late nights would ensue. There’s no rush, and I’m happy to take things slower now.
2020 presented everybody around the globe with new, unprecedented challenges. How did you #FindNewRoads + switch gears towards your new version of success?
I am so deeply fortunate that I had three deeply large scale projects that were already in the works. One being LoveSeen, another being the TV show, and the other being the hotel project that allowed me to continue on as all could be done remotely. I don’t know what I would’ve done without the LoveSeen team in particular. The opportunity to learn how to work remotely with half new team members I've never worked with and half I have known from my previous life, was a blessing. It gave us the chance to get to know each other slowly with no pressure as we hadn’t yet launched.
How are you making a difference and pushing your industry forward?
We’re trying to share a product with people who may not have thought it was for them or that they could play. We want everyone to feel welcome, no matter their age, ethnicity, gender, and hopefully feel seen.
When you separate yourself from your job title and the bells and whistles of your business or career, who are you and what do you like to do? How have you remained true and authentic to who you are?
I am deeply into sleeping. Like, super into naps. I like to watch puppies. I love meeting new people, finding new things. Does this sound like a personal ad?
For those who haven’t started a business (or are about to) what advice do you have?
Do your research, hire people who are smarter than you are, fill in your blind spots, and don’t be too shy to say you don’t know something.
What is your best piece of financial advice for any new entrepreneur and why?
It all counts. Do you remember when you were young and you would go to your bank checking account after you paid for your cable, phone, and electrical bill and seemed like you didn’t have any more money left? It happens quickly. Pay attention and watch the small stuff. That’s what can get you.
What is the #1 podcast you always recommend and why?
I really love “Startup” by Alex Blumberg and Lisa Chow that one of my business partners, Jeff, sent to me. I love hearing about how other people started their business and the straightforward questions they have. I love hearing people talk about their business with such candor and vulnerability.
Fill in the blanks:
To be successful, you need to be…
A touch crazy, tenacious, and open-minded.
I turn bad days around by…
Eating Ashley’s pudding, a hug from Beckett, any five seconds with Kyle and Sarah, and, if all else fails, ice cream.
Three qualities that got me to where I am today are…
Fear of failure, curiosity, and a general obsession with pretty things.
The change I’d like to see in my industry is…
I was at a doctor's appointment recently at a doctor I had never been to before. He asked me what I did, and I said I used to work in fashion. He asked me where, and I said J.Crew. His assumption was that I worked in a store, and when he found out I had been the president and executive creative director, his response was, “Oh wow, good for you.” It felt demeaning. If I was a man, his assumption would have been that I was an executive, and if I was a man, he never would have said “good for you.” Sadly, most industries still underestimate and pass over women in positions of leadership. I feel grateful for all of the success I've been afforded and would love to see more women be recognized.
The craziest thing I’ve done for work is…
I worked 24 hours straight and slept underneath my desk. This was back in the early days.
