There are a few things no one tells you about being a founder. How to be confident as a female founder and entrepreneur is one of those things. The confidence gap is a very real issue, where male founders often come off much more sure of themselves to investors than women tend to, Harvard Business Review notes.

“I used to think that you had to be this superwoman in a suit slaying dragons all day long to feel confident,” CeCe Olisa, founder and curator of Curvy Girls Guide and cofounder of theCURVYcon, tells Worth. “Confidence is possible for everyone. It might take some people longer to find, but it’s there.”


Worth talked to Olisa about her founder journey, her latest project and what it takes to develop confidence as a founder and entrepreneur.

Q: What inspired you to start theCURVYcon?

A: In 2008, I started a fashion blog about my life as a curvy girl in New York City. I used my blog as a space to explore style, wellness and body positivity. My tagline for my blog was, “Don’t wait on your weight to live the life you want.” That was the first mantra I’d ever put in my journal. Thousands of women formed a community around my blog and I began to find ways to use my creativity to serve the 67 percent of American women who wear a size 14+. Shopping as a curvy woman can be challenging. With theCURVYcon, I wanted to create a place where plus size fashion could be celebrated on the runway right alongside New York Fashion Week. Each year during our panels, inspiring women like Venus Williams, Lizzo, Jameela Jamil and Chrissy Metz would come to speak from the heart about inclusivity, self love and body positivity. Women who felt invisible began to feel seen and heard. We’re currently on hiatus due to COVID-19, but I’m very proud of that business.

What did you do prior to theCURVYcon? 

I supported myself with my fashion blog and a 9-5 corporate job. As my fashion blog became more successful, it became overwhelming to juggle my creative passion and my corporate life. I can remember in 2015, I had a photoshoot scheduled during my lunch break. I was rushing to get there so I could get back to the office…I took a spill and I sprained my ankle! It was awful. I resigned from my corporate job very soon after that.


You’re releasing your 2021 confidence roadmap in March. What led you to create that?

Yes! I’ve created a journaling method to help women discover their creative identity and build the confidence they need to go after the life that they want. My confidence roadmap is based on a workshop I teach called “Journaling with Janet (Ms. Jackson if you’re nasty).” Last year led me to really evaluate the life I want for myself. A big part of that is spending less time on social media and more time serving my community of women in impactful ways. I’m finding that private workshops are a great way for me to stay in touch with women around the world on a more personal level. And I love it.

What is the biggest thing people, specifically women, misunderstand about confidence, do you think?

Growing up, my parents really cultivated creativity in me. As I got older, I let my creativity get away from me. Finding my creativity again through journaling and my morning routine has been incredible for me. I used to think that you had to be this superwoman in a suit slaying dragons all day long to feel confident. Confidence is possible for everyone. It might take some people longer to find, but it’s there. Having the confidence to play creatively without judging myself has really inspired my confidence balloon to soar. I like helping women find that within themselves.

What does it take to develop confidence as a founder and entrepreneur?

Oh gosh, it’s painful sometimes. I’m starting a new company this year. I am now a founder, which requires a different level of attention. I’m up to the task. But emotionally, it’s tough. As a cofounder, I always had someone to bounce ideas off of, someone to share the hard times. I realized recently that my journal has become that safe space for me to be vulnerable as a leader. In my journal I can be scared, unsure, frustrated and it’s OK. Journaling as part of my morning routine has been really helpful.

What all does it take to be a founder, in your experience?

The short answer? Community, creativity and confidence. But cultivating those three things is a process that happens over time. I’m blessed to have a community of very special women around me. I am terribly shy about my founder identity. I’m much more comfortable being seen as a creative. But I do have an entrepreneurial side to me as well. So, a lot of my confidence challenges are around my business identity. On the other hand, many of my students come to me saying they feel they aren’t creative. That’s simply not true. Everybody has creativity inside them! I don’t mean everybody can pick up a mic and become Janet Jackson. I mean your creativity is your passion. Your confidence helps you give that passion to the world. They work together to inform all your decisions, especially as a founder.

How do you embrace personal growth as a founder?

Prayer, therapy, a small circle of mentors and my journal.

How can founders and entrepreneurs develop confidence in themselves personally, in their business(es), in their finances and in their ability to be a leader?

Confidence is a process. It grows as you grow, as your passions grow. I like to use journaling to bring it out of myself. I journal three pages a day, every single day.

Lastly, how can founders go about building a business that has purpose built into its mission?

First, you have to find your purpose. Name it. Write about it. Figure out how it makes you feel. And then embrace it as a guiding light towards your North Star.