Today we’d like to introduce you to Matthew Bennett
Hi Matthew, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
Growing up in Waxhaw/Monroe, North Carolina, my life revolved around football. For years, I worked tirelessly to get recruited by a Division I program, but the opportunity didn’t come until my senior year. Eventually, I received offers from universities, including the University of Louisville and several North Carolina schools. I chose Louisville, believing it was the culmination of my efforts and dreams, and I wanted to get as far away from my hometown bubble as possible. However, once I experienced the inner workings of college football—the politics, the mental and physical pressures, the injuries—I quickly realized it wasn’t the path I wanted to pursue. With a heavy heart, I returned to the Charlotte area.
Back home, I took on various jobs, from valet parking to working at a golf course, all while continuing my education (though I rarely attended virtual classes). Even then, I knew the skills I had couldn’t be taught in a classroom. My real education came from observing my father during our four-hour drives to Atlanta for football training. Listening to him handle business calls taught me how to communicate effectively and navigate different environments. Moving to three different high schools, each with vastly different demographics, also gave me an adaptability that shaped who I am today.
After some time in Charlotte, I grew restless. I knew I was capable of more, so I started reaching out to people on Instagram, sending messages daily until I finally got a response. With my family’s unwavering support—though they thought I was a bit crazy—I packed my life into six boxes and moved to California. I thought I was going out there for a job, but when I arrived, I learned it was actually an unpaid internship at an elite athletic training facility in Orange County. Reality hit hard, and I had to make a choice: stay or go back home.
I chose to stay and bet on myself. I promised myself that in two weeks, I would prove my worth and turn that internship into a full-time position—and that’s exactly what I did. Within two weeks, I was hired, and I quickly advanced by leveraging my athletic background and the energy that comes with being young and hungry. At just 18, turning 19, I had dropped out of college and fully committed to this new chapter.
That facility became more than just a workplace. We expanded to open a boutique management company specializing in professional athletes, particularly football, and became part of the early wave of NIL deals. By the time I was 20, I was managing NFL and collegiate clients, leading programs, handling operations, and crafting brand strategies. It was a whirlwind of opportunity, and I thought I was on a clear path to success—until everything changed overnight. Both companies were dissolved due to unexpected circumstances, and in the span of 24 hours, everything I had built seemed to disappear.
In the aftermath, I felt lost. I started freelancing for agencies and helping my old clients while interviewing with some of the largest companies in the country. But every door remained closed, primarily because of my age and lack of a formal degree. It was frustrating, to say the least.
Feeling drained, I decided to step back and accepted a job at a luxury gym. It gave me the space to breathe, refocus, and reassess. I thrived in a sales role, introducing new partnership strategies to the gym and, for the first time in a while, feeling a sense of normalcy. During this time, I met two of my closest friends and future business partners—Ricky Chavez and Drew Lazo. They reignited my drive and gave me the courage to dive back into the entertainment space, but this time with a fresh perspective.
One Thursday night at Barney’s Beanery, Ricky and I decided to start something of our own. That’s how Outlaw Media Group was born. Within a month, we had 25 talents on our roster and our first activations at Stagecoach and Coachella. From the outset, it was clear this was no small venture. I left my gym job and fully committed to Outlaw. My mission was clear: to give back to the athletes and influencers who had sacrificed so much to achieve their success. Whether influencers or athletes, I wanted to ensure their hard work was honored.
I initially planned to move away from working with athletes, but I was quickly pulled back in. Today, I have the privilege of collaborating not only with professional athletes I grew up with in North Carolina but also with superstar athletes across various sports. I originally focused on football, but Drew Lazo’s influence and character shifted my perspective, leading me into the golf space. This shift has opened doors to work with professional golfers, golf-focused content creators, and an exciting new YouTube channel, *Married to the Game*, hosted by Sedona Hopley and co-hosted by Drew Lazo. At Outlaw, we’re passionate about modernizing golf by bringing fresh talent and innovative brands into the sport. Our mission is to bridge the gap between golf’s traditional audience and a broader, untapped viewership.
In just six months, Outlaw Media Group evolved into The Outlaw Group, a multifaceted company with divisions in talent management (Outlaw Media Group), hospitality (Outlaw Hospitality), and YouTube production (Outlaw Studios). I’m honored to have my close friends, Nate Stoner and Riley Stoner, carry forward the Outlaw name in Nashville, TN, through the Outlaw Sport and Social Club. Their leadership ensures that the Outlaw spirit thrives in exciting new ways. Outlaw has grown rapidly, working with some of the biggest names in entertainment, from celebrities and athletes to content creators.
Our success is a testament to the incredible team I have around me: Ricky Chavez, Olivia Sloan, Mairely Estevez, and Drew Lazo. Together, we’re building something meaningful and authentic. Outlaw isn’t just a company; it’s a reflection of the hard work, dedication, and passion each of us brings to the table. We’re just getting started, and we’re committed to staying true to who we are as we continue to grow. The future is bright, and I’m incredibly grateful for the journey that has brought me here.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
It definitely hasn’t been a smooth road. It’s been full of challenges and moments of doubt. I’ve always had almost delusional confidence in myself, pushing forward no matter the circumstances, but when you’re constantly surrounded by people telling you that you’re too young, that you need a college degree, or that you lack the right credentials, it wears on you. Even when your own inner circle questions your decisions, it’s hard not to question yourself.
One of the hardest moments was watching everything I’d built in California over two years disappear in less than 24 hours. Seeing something you poured your soul into crumble overnight can feel like a personal failure, and it took a lot to pull myself back up after that.
What made it even harder was the loneliness. Entering the professional world at such a young age, you’re surrounded by people who don’t take you seriously until you achieve something big enough to make them notice. It’s isolating. There were countless times I felt like no one truly understood what I was doing or why, but I kept pushing. It’s through those moments of loneliness and doubt that I learned the importance of trusting myself, even when the world around me wasn’t ready to.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
At The Outlaw Group (TOG), we’ve established ourselves as a dynamic force in entertainment and influencer marketing. In just six months, we’ve expanded from Outlaw Media Group into The Outlaw Group, with divisions in talent management for content creators, athletes, celebrities, and actors (Outlaw Media Group), hospitality and events (Outlaw Hospitality), and YouTube/special project production (Outlaw Studios).
TOG specializes in managing entertainment figures and brands, creating authentic connections that drive lasting value. We focus on innovative partnerships and strategic consulting, transforming the influencer marketing landscape. By analyzing trends and market dynamics, we help our talent navigate their growth journeys as a cohesive team. We also focus on creating immersive experiences that go beyond standard promotions. Whether through interactive events, captivating content, or strategic collaborations, we aim to forge authentic connections between brands and their audiences. By integrating storytelling with innovative marketing tactics, we help brands stand out and foster loyalty among consumers. Ultimately, our goal is to drive brand awareness and engagement, transforming viewers into dedicated advocates. With our expertise in influencer marketing and event production, we’re committed to unlocking new pathways for brands to reach and captivate their target audiences.
At The Outlaw Group, we’re committed to building something meaningful and authentic, driven by the dedication and passion of our incredible team.
Can you share something surprising about yourself?
One surprising thing people might not know about me is my obsession with 2000s pop music. Artists like Justin Bieber, Rihanna, Akon, and Jason Derulo hold a special place in my heart. Their music keeps my energy high and adds a fun, lighthearted element to my day, reminding me not to take life too seriously. Whether I’m working on a project or just unwinding, playing that music helps me stay motivated and enjoy the journey
Contact Info:
- Website: https://www.instagram.com/theoutlawgroup.co/
- Instagram: https://www.instagram.com/_matthewbennett__/
