More than a decade ago, San Antonio food entrepreneur Daryl Smith took a college business project and transformed it into a powerhouse local wing chain.
Smith and business partner Bernardo Baxter opened the original WingIt location in the early 2010s, which remains home base for the brand. Since then, they have opened another location in the Alamodome and purchased a WingIt food truck.
The duo eventually expanded with a sister drink company, SipIt, which features a wide assortment of alcoholic and nonalcoholic beverages that customers can purchase to-go. That project proved so popular, it’s grown to 16 locations.
We caught up with Smith to talk about his success and building a brand from the ground up.
WingIt and SipIt didn’t start as massive brands but as a single food truck. Take me back to the very beginning.
It really came full circle for me. I’ve been in the game about 14 years now. WingIt started as a class project when I was studying business marketing at Texas Southern University. I created a food truck concept for my entrepreneurship class, and after I graduated, I decided to actually bring it to life.
I found an old taco truck on Craigslist and started selling wings around my college campus in Houston. I’m originally from San Antonio — I went to Judson High School and graduated from Wagner — but at the time, Houston made sense. Eventually, though, business got hard. I had met my wife in college, but I didn’t have family there, and I realized I needed discipline and structure.
That’s when I joined the Air Force Reserve, which brought me to Lackland. My plan was simple: save money, reinvest in my truck, and scale. I wanted 10 trucks — that was the dream.
And that’s what ultimately brought you back home?
Yes. During basic training, something clicked. I kept seeing food trucks on base and thought, Why didn’t I think about this sooner? I realized there was opportunity everywhere.
When I came back to San Antonio, I started setting up in Converse and Kirby. I got my first contract at Fort Sam Houston, and that exposure really helped. Around that same time, my best friend introduced me to my now-business partner, Bernardo Baxter. He had his own food truck, Count Down Wings, and a following from his days promoting parties at UTSA.
When I saw the lines at his truck, I realized, OK, there’s money in San Antonio.
WingIt officially became a brick-and-mortar in 2014. What did those early days look like?
Very scrappy. We found a small spot in Kirby — $700 a month in rent — and made it work however we could. We couldn’t afford a kitchen, so all the food was cooked out of my food truck parked behind the building.
My mom worked the front counter. My cousin was cooking. We were on walkie-talkies calling out orders — “Drop a 20-piece.” It looked like a restaurant, but behind the scenes, it was pure hustle.
That same year, my wife and I got married, and we held our wedding reception inside WingIt because we couldn’t afford a venue. My mom decorated the whole place. That restaurant is truly part of our family story.
When did you realize the concept could scale?
Within three years, we had two locations. The second came almost by chance — my wife spotted a “For Lease” sign at an old barbecue spot. The bones were already there, and because we had experience, the landlord took a chance on us. We were young — 22 and 24 — but hungry.
The real turning point was when we added margaritas and daiquiris to WingIt. Once we introduced alcohol, everything changed.
And that eventually led to SipIt?
Exactly. We came up with SipIt in 2019 as a spinoff concept. My partner handles the financial side — I’m more of the marketing mind — and the numbers made sense. We opened in January 2020.
Then COVID hit in March, and it honestly changed our lives. SipIt became our best return on investment since we started. People wanted convenient drinks they could take home.
During the pandemic, we noticed moms leaving the line to go to Sonic or Bahama Buck’s for their kids, so we added mocktails and non-alcoholic drinks. SipIt became a one-stop shop.
Our mindset was: How do we become the Starbucks or Smoothie King of this market?
You expanded quickly with SipIt — more than a dozen locations. What’s been your “secret sauce”?
Franchising. Once we saw the success, we reinvested and started franchising. Today, we have six corporate locations and more than 11 franchise locations between WingIt and SipIt.
For us, it’s really about focusing on what we know, and then scaling it the right way.
If you could go back and do anything differently, what would it be?
I would have put better systems in place earlier to help us scale faster. But early on, you don’t know what you don’t know. You’re just trying to survive and make it work.
You also talked about giving back. Why does that matter to you now?
Lately, I’ve been going back to my alma mater and speaking to students. I want young people — especially those who look like me — to see what’s possible. I started with a class project and an old food truck.
If I can do it, they can too.
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