Boss FilesMar 19, 2020

Take a Seat With Janessa Leone

Written by All Sorts Of
Photographed by Aaron Feaver

Janessa Leone is the queen of her craft. Not only does she design the most stunning hats, but she does so with grace, humility, and drive. She’s built her business from the ground up, brick by brick, to the place that it is today, and we couldn’t be any more inspired by her. Especially in times like this, we want to do everything we can to support our friends with small businesses, and Janessa is no exception. Today, she launches her brand new SS20 collection. It’s thoughtfully created for life’s simple moments, and that’s a motto we can use right now. Without further ado, take a Seat with Janessa Leone and shop her new collection below.

a conversation with Janessa… 

Tell us about your entrepreneurial journey. How did you build the Janessa Leone brand to what it is today?

I started this company by making a single decision to just begin. I had a lot of self doubt and excuses on reasons why I shouldn’t start my own thing. I received a card in the mail that read “Begin Anywhere” and that day I decided to just start and slowly make progress towards bigger goals. From that day on, I have dedicated myself to work every single day on growing this brand and slowly building a foundation to a healthy business. My motto is slowly, but surely. It’s hard to keep that perspective with all the VC money that gets pumped into consumer product businesses, but I have always been dedicated to focusing on building a healthy business from a strong foundation of values and hard work. As we grow, I am so lucky to have an incredible team of people that are helping me push the brand forward. No matter what growth we experience, I am still dedicated to make progress every day for our ever evolving goals. And while our foundation has been laid, we are still very much in construction phases building the framework for our future business.


What inspires your designs?

My degree is in English literature, and I love stories. I love exploring the different way people live and conduct their lives. I can be inspired by walking into a house and creating a story about who could live there and what their life looks like. I am very inspired by different environments. I am constantly observing how people dress, what kind of furniture are in stores or homes, the architecture of different cities, how different cultures relate to one another. I am notoriously a starer, but I’m so fascinated by people and objects and I am just absorbing it all at all times. A huge part of my process is to spend time in nature on hikes or at the beach; I need to find some quiet so all of the stimulus I am digesting all day can assimilate and can influence what I am to design.


What are some of the biggest challenges you face with owning a small biz and how do you overcome them?

Owning a small business is just one big challenge. It doesn’t end. I think what’s required to overcome the challenges is a shift of  perspective to one of acceptance that challenges are part of the gig; and with every challenge, there are several solutions. You have to make a decision, own it, and move onto the next without dwelling too long or get crushed by the pressure. I think you need to learn to let go of control, trust your team, and not expect to get every decision right.


What advice would you give to someone wanting to start their own professional journey?

Just start! Anything worth doing takes a lot of time and discipline and everyone has to start laying that foundation somewhere.


What’s the best advice you’ve ever received, either professionally or personally?

I don’t have a tidy quote, but I would say the advice that has served me best has come from my boyfriend. He’s been on this journey with me since day one, and he has helped keep this very rocky journey steady by encouraging and motivating me to just put one foot in front of the other every day and not get caught up with comparison or everything that has to happen. He pushes me to just stay present and focused on making small progress everyday, because one day we will wake up and have years of small victories that make a substantial and strong foundation that will pay back in dividends.


What keeps your hustle going every day? What motivates you?

I love creating beauty. I believe that every person is so unique and individual and we are the only person on the planet with our specific perspectives. Therefore we are the only ones to be able to create something from our unique visions. I am constantly inspired by that and feel motivated to take part in our culture and participate in the progressing creative outputs in this time and moment that I’m alive.


What are your thoughts on work-life balance? Do you think it’s attainable?

YES not only is it attainable, it’s necessary. I’m a HUGE believer that we should not live to work. I think our life and work should be viewed holistically as influencing the other. If you are burnt out and not enjoying your life, your work is undoubtedly going to suffer.  If you are healthy and fulfilled in your life, you will be able to show up to your work in a much more effective meaningful way. As a leader of my team, my highest priority is to make sure that people are first and foremost enjoying their life. I set very defined boundaries to make sure that people are taking time to unwind and not working outside the office. The level of energy required to grow a business at the rate that we are growing is full on. It’s paramount that that level of pressure doesn’t start to encroach on people’s lives. We work on efficiencies to get people in the office for the minimum amount of time while still maintaining a high level of work and put a huge focus on enjoying life.


Do you have a daily ritual you can’t live without?

I’m a recent adopter of gratitude journaling. I  wake up in the morning and before I do anything, I write 5 things I’m grateful for. And at night, the last thing I do before I go to sleep is recount 5 beautiful things that happened that day. By focusing on these things morning and night, my brain is literally being trained to look for the small beauty in life and nothing has been more powerful if a ritual – I’m not letting that one go anytime soon.


What are five things you can’t live without?

God, my partner Kevin, my dog Wallace, my friends, tequila.



What’s next for Janessa Leone?

I have big goals, I want to continue to grow and produce beautiful products (hopefully across several categories) while bringing beauty into the lives of the people who are making it all possible.

shop Janessa’s picks 






















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