“We were quite lucky kids because we were taught the value of a dollar early on,” remembers Tyler Dameron, REALTORⓇ with Keller Williams in Naperville. “My parents owned a couple of businesses when we were growing up. We spent time in the back of the store, doing our homework, getting into trouble. Both my parents have been fearless leaders and role models that I've looked up to all my life.”

Growing up in Winfield, IL with his fearless parents and brother, Tyler started playing baseball almost as soon as he could walk. He continued playing on travel teams and in high school, eventually earning a scholarship to play at St. Joseph's College in Indiana. Unfortunately, almost immediately into his freshman year, he suffered a debilitating injury and had to move back home to get surgery and rehab. After recovery, Tyler transferred to Northern Illinois University to study psychology.

“I had a dream of being a child psychologist,” says Tyler. “The brain has always fascinated me, and I wanted to make a career out of it.”

When Tyler, who was always a better athlete than a student, learned he would have to earn both a master’s and a doctoral degree to pursue this dream of child psychology, he decided to shift gears and find a career where he could still leverage his education and background, but get there a little quicker. Tyler bartended at a bowling alley while plotting his next steps. Eventually, he found a job at a global IT company. Starting as a help desk agent, Tyler worked his way up to become a leader in the organization, managing over sixty agents and almost a million clients worldwide. 

“It was an incredible journey of learning how businesses run, how to manage, and how to lead,” says Tyler.

After a decade in IT, however, the corporate grind began to wear on him. His kids were getting older, and he began to miss out on family time, especially the opportunity to coach their sports teams and cheer them on during games. The COVID-19 pandemic gave him the perfect chance to reflect on his present and future career path.

“My kids were growing and starting to get into sports and other clubs, and I just didn't have the time I wanted to spend with them,” says Tyler. “I'm a coach to the core, no matter what the subject is, and it pained me to not be able to coach my kids' teams. I was searching for something that would allow me more flexibility in my daily schedule while still bringing in money to support the family.”

In addition to owning and running his own businesses, Tyler’s dad had a real estate license, which led to Tyler attending open houses and newly built communities just for fun as he grew up. Similarly, Tyler’s wife, Ashlee, has always been interested in real estate, combing through listings as a hobby.

“My wife used to look at million-dollar properties and send me online links all the time,” says Tyler. “So when I sat down and thought about what I wanted to do next, real estate was the clear winner.”

At the advent of 2022, Tyler left his financially stable, but all-encompassing, full-time job in IT to launch his real estate career. He had no plan other than to sell houses and make sure he was supporting his family. Tyler doesn’t necessarily recommend others take this drastic leap of faith, but he knew it was what he had to do for his own well-being.

“I'm probably working more hours in real estate than I did in the corporate world, but I can design my own schedule around my family, which is what will always come first,” Tyler explains. “I'm so thankful for real estate because now I can support my family both financially and emotionally. I can coach my kids’ sports teams, we can go on vacations, and I can finally eat dinner with them at home.”

The freedom he’s found in real estate also allows Tyler to give back to his community in different ways. In partnership with his lender, he maintains a Creating Affordable Real Estate (CARE) program that offers closing credit assistance to active-duty military veterans, healthcare workers, teachers, and first responders. He has also sponsored events for Support Over Stigma, an organization supporting veterans and those in need. 

When he’s not coaching his kids’ teams—Amelia (10) loves softball, and Miles (8) plays baseball—you can find Tyler coaching his colleagues and new agents in real estate. And he sees himself doing both for a long time to come.

“I love to coach, and I can see myself getting more ingrained into that type of role down the road,” Tyler says. “Coaching, mentoring, and selling sounds like a pretty awesome life to me.”