This as-told-to essay is based on a conversation with Tiffany Haynes, host of the Between Builds podcast and Substack. It has been edited for length and clarity.
I was entirely on my own when I was 19. While I was enrolled in college, I worked full-time at night in the call center of a fintech company, Jack Henry & Associates. It was a gritty, hands-on role, but an exciting time to be with the company, which was growing quickly.
I didn’t have a typical college experience. I worked a lot so I could pay for my car and home. At work, I put my hand up any chance I could. I was never the smartest person, but I worked really hard and was always willing to figure out problems. Even if I’d never done something, I would figure it out. I couldn’t afford to fail, personally or professionally.
That served me well. I gained a reputation as someone who could execute tasks with a high degree of excellence, while also operating with empathy. By the time I left Jack Henry in 2022, after 20 years, I had become a vice president.
My husband handled childcare while I worked in NYC
At that point, I was a wife, mom of five, and had been a foster mother to seven children. I live in Missouri, but my reputation was so strong that the team at Fingercheck, a New York-based HR platform, approached me about scaling the company with a goal of acquisition.
I started traveling a lot, and spending two weeks in Brooklyn at a time, with a week at home in between. My husband handled childcare, loading up the kids and bringing them to the school that they attended, where he was the superintendent.
Over three years, I helped scale Fingercheck. In October 2024, it was acquired for $150 million.
After the acquisition, my husband and I founded a school
I stayed at Fingercheck until this July to help with the transition. After that, the plan was to take time to reorient myself and rest.
Yet, life had other plans. The school my husband led was affiliated with a local church. It grew so much that the church could no longer handle it, and this summer, we had a choice to make: let 100 kids find a new school community, or open our own.
It was a whirlwind four months, but we did it. I call myself the quiet cofounder of the school, and I’m not involved in day-to-day operations. Now, I’m doing some advising work and have a podcast called Between Builds. I’m also taking some time for myself to be whole, rather than hurried.
We connect almost daily over coffee
My husband doesn’t take a salary — his work is our way of giving back. When he left his paying job 13 years ago to enter education, I became the breadwinner. We’ve had a lot of practice respecting one another’s domains.
The work I did with Fingercheck in New York was very fast-paced, urban, and growth-focused. The work he does here in Missouri is rural, quiet, and focused on community. It’s two different ends of the spectrum.
We appreciate each other’s different skill sets. I support the school, because he loves the school and I love him. He handled the family when I needed to travel for work, even if he didn’t fully understand the fintech world. We connect almost every morning over coffee, before the kids are up, and talk about how we can support each other. We aimed to do that even when I was working full-time, but it’s easier in the months since I left Fingercheck.
I want my kids to understand the joy that comes from hard work
I grew up poor, and I understand how privileged my family is today. We have more than enough, so we aim to give not only money but time. I try to be the advocate I never had growing up, both to my own kids and the children we foster. I’ve done a lot of work to process my own trauma from a difficult childhood, and I want my children to have a foundation of emotional intelligence and health.
I also want them to understand that it takes a lot of hard work and consistency to be excellent. They see YouTube influencers talking about making millions, and I worry that creates a short-sighted view of worth ethic and personal meaning.
I hope my kids understand the joy you get from doing hard things. I want a space where they can sit with frustrations and build resilience; I know that will serve them well in life.
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