Allison Cousins wasn’t too familiar with St. Louis when she moved here in 2015. While she had driven through St. Louis during college, she said her first impression of the region was “through Google Maps and scouting around different parks” as she prepared to move here.
Originally from Alabama, Cousins has ingrained herself into the St. Louis region since relocating here. Today, she’s the founder of both a technology startup and schools-focused nonprofit. She is co-founder and CEO of Approach Dating, which has developed a dating app designed to lessen the digital requirements of online dating, seeking to enable quicker in-person meetups for those who connect through the app. That includes developing a “live” version that would allow users of the app to meet up at events like sports games and concerts.
Cousins is also founder and commissioner of City League, a nonprofit she formed to offer youth sports programs for St. Louis charter schools. She incubated City League while a teacher at charter school Lafayette Preparatory Academy. Cousins has high ambitions for the nonprofit, hoping one day it develops its own multi-sports complex.
What made you want to begin your career in teaching? From a very young age, I always wanted to be a coach and a teacher because I had transformational relationships with people in my life that became mentors and I wanted to be that for other kids in my shoes. My formal education is in education, secondary specifically. I got my masters shortly after my undergrad in management and information technology because I knew that education was going to shift to become so much more technologically centered. Formally my background is in education, but I've always had that entrepreneurial mindset. I had a lemonade stand when I was a kid, and my mom gave us startup funding and then she was like 'OK, now you have to pay for product.' That taught us a little bit about business through those things as a young kid. I feel like I've always seen that in myself. Even when I wasn't working, I was organizing community events and doing things that now I see being reflected in my work.
You mentioned your interest growing up in entrepreneurship. What made you want to do it full time? I think my divorce had a large impact on my personal transformation and realizing who I am and who I want to become and what career path I want to pursue. For a period of time there, I was a stay-at-home mom for four years. I put my career on pause and then as I went through the divorce, shortly after that, I was like "what's next for me and what kind of life do I wanna build for myself and for my kids, and who do I want my kids to see me as?" Through that, I was continuing teaching and Approach and City League both really started around 2020. Honestly, the pandemic created space for me to pursue figuring out what that looks like. And then not only that, I just had a lot of support from both the startup ecosystem and then also from the school that I was working in.
How did City League get started? The education landscape in St. Louis is really unique because almost 50% of kids in St. Louis are now attending charter schools. That largely started because St. Louis Public Schools lost accreditation — it is now accredited — 10 years ago and started this movement. All charter schools are still publicly funded, but they operate independently. There's no district level decisions being made. It’s all kind of in-house. The main con of that is a lot of the resources and funding is going towards overhead operations, whereas on a district level, that's kind of all distributed under an umbrella. Charter schools nationally, only 19% have opportunities for students to participate in school sports, which is just kind of atrocious. When I started at this one particular school, there were no sports, no extracurricular programs. They have a partnership with a program called Beyond School, but that was the only option of any kind of after school extracurricular. A lot of kids who are really athletic and really into sports had no formal training. So I just said "this is something that our school needs' and sports was something that was transformative in my life and I know the framework to build it, so I'll just do that. Then I realized that it was not just our school and looked bigger into the city. There’s now 17 charter middle schools in St. Louis, and a large portion of them were also in the same kind of phase of growth in terms of the school, but without any programs or options in terms of sustainable and structured programming. So I just said I'll coordinate a little league and see what happens. That was really how it started.
How are things going with Approach Dating? Things are going well. We are in an exciting time. We just raised a real small round of funding to extend our runway and continue our development. We are in early conversations with our new development firm to look at what building out this live feature would look like, which is the feature that we have identified as our true differentiator. We are also scaling into Kansas City in July. We're launching our singles events at our partner businesses in Kansas City and right now we have three partners there. They all host monthly singles events targeted at different age groups and interests.
What do you like to do in your free time? I'm an athlete myself, so I play in a recreational sand volleyball league and ride bikes. I have a dog, so I'll go up to Bar K. I have kids, so I spend a lot of time driving them to and from their activities, sports games, watching them and cheering them on. Family and friends — those are my priorities.
What’s it like being a founder and having one foot in the for-profit world and the other in a nonprofit? I think about that a lot. There's so much that overlaps and there's a lot that's different as well. Being in both sectors, I've learned so much from the other and I’ve been able to apply it, whether it be relationship-based, whether it be the power of storytelling, whether it be raising funding. There’s so many things that are slightly different but apply in the same ways or variables. There is so much parallel, but ultimately a lot of things transcend just in their own little niche.
More about Allison Cousins
Title: Co-founder and CEO, Approach Dating; Commissioner and founder of City League
Age: 34
Family: Boyfriend; and two children
Education: Cousins has a bachelor’s degree in English and secondary education from the University of Alabama in Huntsville and a master’s of science and education, with an emphasis on management and information technology, from Western Oregon University.
