If you haven’t heard of Taylor’s Tacos yet, you’re missing out on more than just the incredible food. Nestled on Taylor street on the Near West Side, the three-part business is more than a taco shop — it’s a movement. With a catering company, an event space (Taylored), and a nonprofit (Tacos Create Community, NFP), Taylor’s Tacos is built on flavor, culture and connection. 

Last week, the Sky sat down with founder and CEO Taylor Mason to reflect on her journey — from athlete to entrepreneur — and her recent win at the Beyond Basketball pitch competition. Her story is one of evolution: the growth of a person, a business and a community.

From Basketball to Tacos: An Unexpected Path

Taylor didn’t set out to be in the food industry, it found her. As the go-to cook for Pepperdine University’s women’s basketball team, she saw firsthand how food could bring people together. But at the time, it was not her career plan. 

Post-grad offered options of playing ball in Spain or sports marketing in Los Angeles, but instead she returned home to help care for her mother. During this time, she also helped out with the family business, teaching the fundamentals of basketball. By the time she decided it was time to venture out on her own, she had helped the business reach over $900,000 in sales. 

Building a Safe Space, One Taco at a Time

Returning to Chicago brought a mix of emotions and realizations for Taylor, specifically the lack of safe spaces for queer Black women. 22 years old at the time, she organized creative events, brought the tacos and eventually noticed how people kept coming back for them. Her tacos evolved to reflect a fusion of Chicago style and traditional Mexican street taco culture: simple, flavorful and designed to be eaten on the go. The goal? Provide enough to fuel people through their day without slowing them down.

While Taylor and tacos found their way to each other, it wasn’t a fluke. The product we see today is a result of years of research, feeling and flow. Still, they do the work every day to get better and improve. And in her words, “they may not be your uncle’s tacos, but they’re memorable and certainly delicious.” 

Growing a Business, Finding Balance

Since that time, her relationship to her business changed drastically. When you start a business, it becomes your baby — you pour everything you have into it, hoping it manifests into something sustainable. Taylor shared how this can blur the lines between the personal and professional. Her wife, Maya, has been a grounding force, reminding her that the work will still be there tomorrow. The email can wait. The client experience matters, but so does taking care of yourself. Now, after a decade of hustle, Taylor’s Tacos is growing up and Taylor is finding time to return to her hobbies — including DJing.

Beyond Basketball and Beyond Business as Usual

Last year, Taylor’s Journey brought her to Beyond Basketball, a pitch competition and business accelerator that supports women- and BIPOC-owned businesses. Over four weeks, participants take courses, workshop ideas and refine their strategies before competing for funding. The top three winners receive capital ranging from $10,000 to $30,000 — funding that can completely change a business’s trajectory. 

For Taylor, being part of a program that can award game-changing capital is what puts Beyond Basketball above the rest. In a post-COVID business world, the ability to change a business’s trajectory is huge. Programs like Beyond Basketball are more than a one-time check. They’re about continued support, amplification, resources and manifestation to keep businesses thriving. 

Before the competition, working with the Chicago Sky was on Taylor’s vision board. Now, that dream is a reality. Next on her list? Collaborations with Brandy, All-Star Weekend and continuing to uplift the people around her. Because for Taylor, business isn’t a competition — everyone can eat and win.

A Business That Gives Back

The belief in community is what makes Taylor’s Tacos special. It’s not just a place to grab a meal — it’s a space for people to connect, put their phones down and be present. For them, the work doesn’t stop when the food is served. They’re building something people can count on, a business rooted in culture, connection and giving back.

The Chicago Sky are proud to support Taylor, Maya and the Taylor’s Tacos team. We can’t wait to see where the future takes them.

Ways to Support Taylor’s Tacos:

Visit them on Taco Tuesday

Book Catering 

Attend an Event

Spread the Word

Participate in Tacos and Goals – Set a goal, find an accountability partner, achieve it, earn a free taco.