Interview: Twenty Seven


Welcome back to shop spotlights! It's time to get back into a regular cadence of sharing killer women-owned shops, and I can't think of a better one to start with than Twenty Seven.


Like most brands these days, I first came across Twenty Seven on Instagram and was drawn to the colorful designs and motivational sayings. However, it didn't take long to realize that there was more behind it than cute greeting cards (although they have those too!). Jenna O'Brien, the creator and artist behind the brand, started it while coming to terms with her mental health, and her personal journey plays a part in all that she does. Positive messages come through in all of her work, and it's easy to see why someone struggling may look through the selection at Twenty Seven and feel a little less alone. Much of the mental health space used to be very deep and serious, but Twenty Seven is cheerful, bright, and full of color dots, fruit prints, pop culture, and more. The space Jenna has created in such a short time is an inspiring one, and I can't wait for you to get to know her.


Q: Let’s start from the beginning. Can you tell me a little bit about the process of starting your business? What made you want to do this and how did you turn your idea into a reality?

A: Twenty Seven started in my college dorm room. I had been diagnosed with Pre Menstrual Dysphoric Disorder (PMDD) and had struggled terribly with depression & anxiety as a freshman in college. I kind of took up random craft projects to distract my mind and found a love for making with my hands - and eventually began to play around with illustrating. After lots of counseling and finally getting correct medication, my mind started dreaming about the future again. And I really wanted to make a blog that talked honestly about mental health, so I carved out a little space on the internet named “Twenty Seven.” I had found that most hopeful resources about mental illness were not really realistic - and most realistic resources were not very hopeful. I wanted to start my own space for honesty AND hope. So I started writing, had friends write too, and then started drawing images to go with the posts. Soon that turned into me offering prints of illustrations and combining the crafty projects I was already making into a little marketplace.


I live in a really cool small-business loving city so there were lots of opportunities to jump into local markets, and I quickly found myself selling at markets all over Florida every weekend. It’s been organic, and honestly mind-blowing growth since then! I worked very hard to create a brand and make a product line, and then launched a Kickstarter to open up a brick & mortar location in Lakeland’s historic downtown. We opened in August and soon after had a little crazy viral phase on Instagram with my enneagram color dot series - and since our following grew so quick, our online store has too! So now we are about 50/50 in sales - brick and mortar and online! It’s a wonderfully fun madhouse haha!


Q: What was your first product to take off or find enough success that you were encouraged to do more?

A: At my first market, I had painted wood chips and turned them into magnets. I sold a whole bunch. I had $80 at the end of the night and that was literally all it took to get me hooked on creative business!


Q: What were your friends and family’s reactions to you starting a business? Were you nervous to share it?

A: I think most people thought it was a good side gig in college for me, a creative outlet, if you will. It was a lot more scary to tell everyone that I wanted to raise thousands of dollars to open a store about 2 months after my wedding! Ha! But my family, friends, and especially my husband have been so essential and helpful to making so many dreams happen. I am so thankful for their support.



Q: How long did it take you to transition into a full-time job?

A: It was a side gig for about three years while I was in school, then I went full time!


Q: I love that so much of your business’ focus is on mental health. Can you tell me a little bit about sharing your personal experience and how it is connecting with others who relate?

A: I think the crazy thing about Twenty Seven is that it is SO personal. Not only am I putting all my own artwork out into the world, it’s all coming from my own journey with mental illness. It’s terrifying every day! But I know it’s exactly what I was made to do.


I have Pre Menstrual Dysphoric Disorder, which is a cyclical mood disorder that causes some extreme anxiety and depression in tune to my menstrual cycle. I’ve never tried to hide the fact that making my business was part of my mental health journey, and the more I open up about it - the more people relate. It’s a wild reality. Occasionally in our small town, my husband and I will get stopped by a stranger in the grocery store who recognizes me and tells us they started g