Today we’d like to introduce you to Kiswana Charmaine.
Kiswana, we appreciate you taking the time to share your story with us today. Where does your story begin?
I was born and raised in San Diego, California. I grew up in a neighborhood that was 15 minutes from the border called Chula Vista. My dad was in the Navy, so structure was just part of life—early mornings, strong handshakes, and “yes ma’am” before I even knew what coffee was. I was an all-star athlete in high school running the hurdles in track & field and playing on the Varsity team, constantly pushing myself to be better, faster, stronger. But beyond the games and medals, I was just a girl trying to figure out where I belonged. I grew up in a family of four. My parents who were high school sweethearts and my little sister. I was involved in yearbook and choir and enjoyed it when I was young.
I started college at San Diego State University, trying to find myself again. After college, I went on to assist in managing a pool hall while teaching pre-kindergarten and junior kindergarten between San Diego. I loved working with kids because of their honesty and their wild, unfiltered outlook on life. They’ll tell you your breath stinks, your shoes don’t match, and that they love you—all in one sentence. And somehow, it always felt like truth. My mom was also a teacher and it was her passion to be there for all the kids she taught, I Teaching gave me patience, purpose, and perspective. They taught me how to be present, and I gave them room to be their full little selves. I taught because I wanted to be like my mom, but I soon realized I wasn’t her.
Eventually, I made the decision to step away from the classroom. It was a hard choice, but I knew it was time to rediscover parts of myself that had been put on hold. I began modeling in runway and for conventions. Then took my aspirations to print. I also hosted with Vice Media interviewing music artists in Memphis, TN. A few years later, I started teaching kids modeling and acting as a part-time passion. Watching them light up with confidence, helping them break out of their shells—it brought me joy in a way I hadn’t felt in a long time. It wasn’t just about posing or stage presence—it was about showing them they had a voice, a light, and a place in the world.
But before all that, I gained experience in the restaurant industry when I got my first job at Red Lobster a little after I turned 18. From there, I worked at resorts, country clubs, speakeasies, and more. I learned customer service, the value of hard work, and how to juggle multiple roles—all while staying calm under pressure. In Houston I bounced around from places like Monarch Bar, Belle Station, and Big Tyme Billiards before coming to realize being a bartender and server in the industry wasn’t for me any longer. Those years built the foundation for my later career moves, teaching me how to navigate high-energy environments and develop the kind of connections that last.
In 2018, I gave birth to my daughter, and in her, I found my reset and my daily reminder that I could do hard things. My daughter became my why, the driving force behind my decision to make a change. Even with family around, something in me still felt unsettled. I wasn’t growing. I wasn’t dreaming out loud anymore. And that’s when I knew it was time for change.
Outside of work, I’ve developed a love for cooking, eating clean and going to the gym. It’s become a grounding practice for me, a way to maintain balance amidst the craziness of life and keep myself energized for the next challenge. Another passion of mine is attending art shows, music events, and networking events around Houston. The city is full of life, culture, and connection, and I love immersing myself in all the creativity and energy it offers.
My favorite saying is, “There is no fear in love,” a Bible verse that has kept me grounded through it all. Every day, I remind myself that when I lead with love, there’s no room for fear. Fear doesn’t have power when I choose to embrace what’s meant for me.
Now, it’s 2025, and I’m more proud of myself than I’ve ever been. I’m not just surviving; I’m living—loudly, boldly, and with purpose. I’m raising my daughter to see that starting over doesn’t mean starting from scratch—it means starting from strength.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
The road here was anything but smooth. There were setbacks, silent battles, and moments I wanted to give up–but chose to grow through it, not just go through it. If it were easy, everyone would do it. truth is, I wouldn’t be who I am without the bumps. Kind of like driving through Houston—some roads are so rough, you have no choice but to ease over them like a speed bump. That’s how I learned to handle the hard times: One steady push at a time, knowing the smoother pavement was up ahead.
My mother passed away from breast cancer when I was 16. That moment split my world in two. It shook everything I knew and left me carrying more fear than most people could see. Fear of loss. Fear of failure. Fear of not being enough. I kept going—school, sports, smiles—but deep down, I was surviving, not living.
I made the bold decision to move to Houston to build a better life. At first, I left my daughter behind with family to create a foundation for us, with the goal of eventually bringing her to join me. With the help of my family, new friends I made in Houston, and coworkers who embraced me, I began to shape the life I always wanted. I didn’t have connections, savings, or a clear path—but I had vision, grit, and people who supported me every step of the way. During this time, I was homeless for months, staying in my car or hotels. It humbled me. It gave me a new perspective on people. It taught me discipline. It became a learning experience that showed me the importance of resilience and pushing through even when life feels uncertain.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Now, I’m working as a Solutions Specialist at Shift4 and I decided to go back to school so I’m currently earning my B.S. in Marketing. I love helping restaurants and bars with their payment systems and technology. Technology gave me a new lane to grow, connect, and dream bigger, Its not just the tools and systems, it’s the opportunity in motion. The same way technology has helped me and my family grow, I whole heartily believe it can help my clients grow also. If I were to go back and tell 16 year old me what I do for a living, I think she’d think I was out of my mind. Every part of what I do daily fulfils my spirit Shift4 saw the entrepreneur in me and recognized the potential I had to grow. The bond I’ve built with my merchants and the people I meet in the service industry feels like family, and I cherish how I’m able to bond over our shared love for food, the highs and lows of the service industry, and a mutual appreciation for music or cocktails. It’s incredible to be in a space where I’m thriving—doing work that excites me and knowing that I’m making an impact in the restaurant industry. With SkyTab, our POS system, we’re a solution that helps business owners take control, stay organized, and serve their customers better. I’m able to show people how technology like this can make their lives easier. That’s the magic in what I do. I get to support the same kind of people I once worked alongside in the industry.
Alright, so to wrap up, is there anything else you’d like to share with us?
I’m in the works of starting a networking group that builds bonds between mothers and daughters. I know what it’s like to be a mom chasing purpose while raising a daughter to believe in herself. I wanted to create a space where both can thrive together. The group is about building confidence, connection, and community–because when moms and daughters grow side by side, it changes everything
Contact Info:
- Website: skytab.v5.platform.sportsdigita.com
- Instagram: https://www.instagram.com/kiswana.charmaine?igsh=MWFkMDVwYjBseDltNw%3D%3D&utm_source=qr
- Facebook: https://www.facebook.com/KiswanaW/
- LinkedIn: https://www.linkedin.com/in/kiswanacharmaine?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app
Image Credits
Gregory Lopez
