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Working multiple jobs is a reality for many Clevelanders. Some turn that grind into pursuing a dream or simply finding community. Our Side Hustle multimedia series aims to capture their hustling spirit. Watch the video or read the transcript of my interview with Charron Leeper below.

Hi, my name is Charron Leeper. I’m the CEO and founder of Perfect Pineapple. Perfect Pineapple is a head wrap and hair accessory brand that I started here in Cleveland, Ohio around 2017.

Why did you start Perfect Pineapple?

I started just because I wanted to learn how to preserve my curls at night and I took a scarf that my grandmother gave me and learned how to wrap it several different ways. And that’s when the light bulb went off: How many people don’t know how to wrap their hair at night? And so I created a prototype. I started wearing them to work. And lo and behold, Perfect Pineapple was born — a small head wrap that you can wrap five or more different ways. I consider it my side hustle right now, because it’s really something that I’m building into a business.

I started it in my grandmother’s basement. I just wanted to continue the business on in her name, because when she passed away, she did have me make her a promise that I would start a family business. And so it didn’t have to be this business. Because she was able to be with me during that process. I feel like it’s only right to kind of dedicate this business to her.

What’s the process for making a head wrap?

The process is just kind of measuring out the fabric. I had to find like the right dimensions that made it small enough to travel with but also versatile enough that, if you wanted to do a forehead wrap, you would still get that crown and glory kind of look with this wrap. And that they also stay intact after multiple washes. So it’s a really simple design that has a lot of versatility.

How do you feel being an entrepreneur?

A lot of times we go through impostor syndrome, but I think what brings me back to life is when somebody’s like, ‘Oh, hey!’ when they see me that I have my Perfect Pineapple. I wear it every day.

That’s crazy to me. It makes me feel like I built a community in a short amount of time. And I think it’s just a testament of endurance and just never giving up.

What’s your vision for Perfect Pineapple?

I want to be the Kleenex of head wraps. I want you to think about Perfect Pineapple wraps when you think about anything related to tying your hair. I think you’re born as an entrepreneur. I think when you’re really entrepreneurial it’s just in you. You just want to create, you want to reinvent, you want to do new things, you want to break barriers. That’s been me since I was a child. My first hustle was these like Kente cloth bows and I was selling them for $1 and my mom like helped me package them up. So I mean, I’ve always just thought that way. And I think you don’t realize it until you look back and see it’s just who you are. You know so here we are. Here we are.

I am Charron Leeper. And Perfect Pineapple is my side hustle.

Learn more about Charron Leeper’s Perfect Pineapple story from Economics Reporter Olivera Perkins:

Jeff produced multimedia content for Signal Cleveland through December, 2024. He focused on producing work that is approachable, entertaining and creative.