Olivia & The Cutest Sleep Accessories – 41 Winks


Olivia is the lady behind the cutest sleep accessories out there – 41 Winks. She told us about how she led her company to find the perfect product in a saturated market, and how to keep your confidence while being surrounded by other entrepreneurs in a big city. When we met, she was wearing comfortable millennial pink sneakers and an adorable embroidered dress that she has worn since high school. She made sure to bring some samples and disco balls, which are part of 41 Winks original branding.

Growing up in Texas, Olivia went to California to attend the University of Southern California. She studied Spanish and International Relations. After college, she worked at a security risk analysis firm with a plan to go to South America for work, but quickly moved to Brooklyn, New York, to run her aunt’s company 41 Winks.

Why did you decide to work for your aunt’s company?

While still in college, I came to New York to intern for my aunt who had just launched 41 Winks, originally founded as a dorm room bedding company. When I graduated from USC the company had been on pause, but my aunt gave me an interesting proposition: ““You always wanted to live in New York City, why don’t you move here, let’s get 41 Winks back off the ground, and see where we can take it?” A pretty easy sell, so naturally I said yes. I was kind of expecting it to be temporary, but of course it ended up becoming my baby. I took over the business and have since transitioned us into the sleep accessories brand we are today, focusing on eye masks and decorative pillows. I found that rather than reaching the college dorm bedding market, it was actually young professionals coming to us more for giftable, unique accessories.

What process did you go through to make that product shift?

“It was a lot of research into what people were coming to us for, what was selling, and what we were excited to sell. Our customers weren’t coming to 41 Winks to remake their bedroom; they were looking for a special or novelty product that a small business can provide. The idea to create eye masks came from a brainstorming session with my team – an intern pitched the concept one day, and before we knew it we had a sassy product designed, tested and selling. Although we’ve since updated the design, our BLOCK OUT THE HATERS in Bailey Cotton Sateen was the first ever!

After receiving feedback, hosting focus groups and hearing about what the avid eye mask wearer is looking for, we redesigned and perfected the product to be more comfortable and really block out the light – cheeky, fun and functional. We are excited to say our first full collection launched officially a year ago this month! With these products, we entered into the wholesale market for the first time and are now working on exciting partnerships to really leverage the unique capabilities our eye masks have to offer.

What was the original goal for 41 Winks?

“Although our product focus has shifted, sleep, the importance of sleep, and making sleep fun has been the goal since the beginning. My aunt worked with a designer to create our Bailey fabric. It was once used for duvet covers, shams and a bed skirt. It is now used for our best-selling eye mask. It’s so fun to see this constant thread through our evolution.


What was the biggest challenge you faced running 41 Winks?

“Probably overcoming my own self-doubt, oddly enough in the form of ego, fear of failure, and insecurities all in one. Being in New York City, there are so many incredible businesses that are starting up every week, if not daily. It can be very distracting and disheartening to look at other successes and compare it to my own. But there are also so many beautiful connections I’ve made while living here. It doesn’t have to be a competition but rather a collaboration. Being comfortable in my path and not comparing is difficult. So I celebrate the small wins and have become very proud of what we’ve accomplished in last four years, especially this past year. We truly wouldn’t be where we are today without everything we did before.”

What was the biggest learning experience?

I have found that movement is key. Continuing to move forward and take that first step is the only way to bring something to life. And once the process starts rolling, the ideas that are meant to stick basically start to create themselves. I really think there is value in not giving up – keep going and keep trying. Nike knew what they were doing with their “Just Do It” motto.

What does it mean to you to be powerful and confident?

It’s easy to equate power to force and authority, but to me, it’s much more powerful to equate power to kindness, creativity and self-expression. We should get more used to that kind of power. When I’m focusing on those three goals, plus getting a great night’s sleep and spending a few hours a week of dancing, I find I am most confident. Although confidence is such a personal feeling, it directly affects those around me. I want to feel confident in who I am so that I can interact with others coming from a kind, creative place.



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