We recently connected with Colton Benford and have shared our conversation below.

Alright, Colton thanks for taking the time to share your stories and insights with us today. Let’s start with a story that highlights an important way in which your brand diverges from the industry standard.

What sets Tailgate Group apart is how personal and hands-on we are. We’re not a big corporate operation—we’re a small business built on real relationships. I started Tailgate Group back in 2011 when I was a student at Ole Miss, and more than ten years later, I’m still the one behind the scenes making sure things go right—whether we’re in Oxford, Athens, Columbia, or somewhere in between.

We keep it simple and tight-knit. Our local crews have been with us for years, and we treat every client like a buddy, not just another job. A lot of people are surprised when they realize they’re texting with the owner—but that’s the kind of service we believe in. You’re dealing with someone who really cares.

We hear it all the time from fans: they love the gameday atmosphere, the little details, and the convenience and ease of it all. That’s what makes Tailgate Group more than just tents and TVs—it’s the difference between an owner-operator-run business verses one controlled by private equity.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve always loved college football. Growing up in the South, Saturdays were everything—from SEC rivalries to backyard cookouts with neighbors. I was the kid dragging out TVs, tables, and coolers before I even knew what “tailgating” was. I just wanted to recreate the energy I saw on campus and bring people together. The only difference back then was my dad was the one cleaning it all up after I went to bed.

That love for game day, mixed with a tendency to hustle, is what eventually became Tailgate Group. I’ve always looked for ways to make things happen—mowing lawns in high school, renting out houses in my college town before Airbnb was a thing, setting up tailgates for family friends. I didn’t have a five-year business plan or anything—I was just a college kid having fun and making good money while doing it.

I launched Tailgate Group in 2011 as a junior at Ole Miss. It started with just one setup in Oxford, but it didn’t take long to realize there was a real demand for high-quality, turnkey gameday experiences. Since then, we’ve grown from one state to six, expanded across the Southeast, and scaled the business more than 30% annually in the last five years.

Tailgate Group is an event services company with a niche in the college & professional sports hospitality arena stretching across the southeast. We set up client tailgates at their preferred location, allowing guests to enjoy a full day of game day festivities without the hassle. From setup to breakdown, every detail is handled start to finish. We’re here to take the stress out of game day, so clients can kick back, enjoy the moment, and make the most of their game day experience.

Have any books or other resources had a big impact on you?

The book Blue Ocean Strategy by W. Chan Kim and Renée Mauborgne has definitely shaped how I think about business. It talks about how instead of trying to outdo your competition in a highly competitive market, you should look for untapped markets where there is little to no competition and capitalize —or even create your own market entirely. Basically, find a niche. The authors describe this as the difference between “red oceans” full of bloody competition and shrinking profits, and “blue oceans” full of new opportunity and growth potential.

That way of thinking has played a big role in how we’ve made decisions. The Grove at Ole Miss is a highly competitive market where margins and profit are lower, this led us to shift our focus to other universities where there’s more opportunity and less competition—and it’s been much more profitable.

We also carved out a niche within the niche by designing custom tailgate trailers, including a remodeled Airstream with a bar and 3 TVs. They’ve been really popular, and we’re planning on adding more to the fleet this year.

What else should we know about how you took your side hustle and scaled it up into what it is today?

Yes. Tailgate Group started as a side hustle, and now it’s my full-time focus. It is a seasonal business—we primarily operate and execute bookings 3 months of the year, that is only a quarter of the year we are doing the work. So, for a while, it made sense to try to do something else the rest of the year. From around 2013 to 2018, I was bouncing between Tailgate Group and selling real estate. It wasn’t until 2019 that I really thought, “Okay, this could be my full-time thing,” especially if we started adding more events outside of football season.

Then Covid hit, and everything slowed down. But by 2023, it was clear—I needed to put 100% of my time into this. It was my most profitable work, and trying to split time with something else just didn’t make sense anymore. I read something in Ninja Selling that stuck with me: the more focused your energy is on one thing, the more it grows—a return on focus. For a while, I split my time between Tailgate Group and real estate sales, and things moved slowly. When I shifted to spending over 80% of my time on Tailgate Group, momentum picked up fast. Now that I’m all in, the business has taken off. The book says 100% focus brings unlimited potential—and I’ve seen that play out.

Since going all-in on Tailgate Group, we’ve expanded our territories, grown sales by 30% year over year, increased bookings, and doubled our team. We also launched a sister company—a mobile bar built out of a refurbished Airstream. In the fall, it serves as a tailgate trailer, and the rest of the year it shows up at weddings, private events, and festivals. At the end of the day, it’s always been about staying creative and turning side hustles into something bigger.

Contact Info:

• Website: https://TailgateGroup.com
• Instagram: https://www.instagram.com/tailgategroup/
• Facebook: https://www.facebook.com/tailgategroup

Image Credits

I own the images.