Episode 10
Let’s Taco ‘Bout It: The Taylor Tacos Story with Taylor and Maya Mason, Part II
Listen to Part Two here.
About the Episode
In this second of a two-part episode of The Big Dig Chicago, we sit down with Taylor and Maya Mason, the entrepreneurial duo behind Taylor’s Tacos Chicago, to explore how a bold idea turned into one of Chicago’s taco brands.
Their story begins with curiosity, travel, and a willingness to try something unexpected. After discovering the vibrant street-taco culture while attending college in California, Taylor Mason returned to Chicago inspired to recreate that experience in her hometown. What began as an idea soon grew into a thriving business built on flavor, community, and persistence.
For some, the concept raised eyebrows. Two African American women building a taco business? Why tacos?
In Part Two of our conversation with Taylor and Maya Mason of Taylor’s Tacos Chicago, we move beyond the origin story and into the beautiful, messy, and ambitious work of building a business.
Starting a business is one thing. Sustaining it, scaling it, and growing it into something larger than yourself is another.
Taylor and Maya pull back the curtain on the realities of entrepreneurship: navigating Chicago’s competitive food landscape, building a recognizable brand, learning through setbacks, and discovering what it means to grow while remaining grounded in the values that made people connect with them in the first place.
We explore the evolution of Taylor’s Tacos from a promising idea to an expanding culinary enterprise—one that now includes catering. Along the way, they reflect on what it means to build as partners: balancing roles, supporting one another, and learning how to sustain both business and relationship while under the pressures that come with entrepreneurship.
This episode also digs into a larger question: what does community really mean when you're building a brand?
For Taylor and Maya, the answer lives in a philosophy they call CommuniTAY: a belief that food can do more than feed people. It can create belonging. It can connect neighborhoods. It can make strangers feel familiar.
At its core, this conversation is about growth not simply in business, but in vision.
Because success isn't just about serving more tacos.
About the Guests
Taylor and Maya Mason are the founders of Taylor’s Tacos Chicago, a Black- and LGBTQ-owned culinary business known for its vibrant street-style tacos and community-centered approach to food.
Founded in 2018, Taylor’s Tacos began as a small catering venture and quickly grew into a sought-after presence across Chicago’s event and food scene. The business now operates out of The Hatchery Chicago, a nonprofit food and beverage incubator designed to support emerging culinary entrepreneurs.
Taylor, a West Side Chicago native, first fell in love with street tacos while attending Pepperdine University in California. Inspired by the flavor, accessibility, and communal spirit of taco culture, she returned home determined to introduce that experience to Chicago audiences.
Maya Mason brings creative culinary vision and artistic perspective to the business. A graduate of the Chicago Academy for the Arts and Columbia College Chicago, Maya grew up in a family where cooking and gathering around food were central to community and celebration.
Together, the pair have built Taylor’s Tacos into a brand defined by bold flavor, entrepreneurial grit, and a philosophy they call CommuniTAY. It is the idea that food can bring people together across neighborhoods, cultures, and experiences.
