“My path could definitely be defined as ‘the road less traveled,’ i.e., hard work, sweat, and grind,” says Aaron Gaines, REALTORⓇ with Keller Williams Preferred Realty. “I have not always been the most talented in the room, but I know I am one of the hardest-working.”

Born and raised in Chicago, Aaron was surrounded by hard-working influencers in his family from a young age. His mother, who was originally from Arkansas and one of eight children, raised Aaron and his sister as a single parent and sole breadwinner. Of all the motivational and entrepreneurial role models in his life, Aaron’s mom was the biggest.

“She was a force, going out and making income anytime we were lacking,” says Aaron. “She was a hustler, too, and no stranger to direct sales. She worked for companies like Mary Kay, Tupperware, and Avon. I saw the power of sales right in my very home.”

In addition, Aaron’s uncle and cousin were the owners and operators of many of their own businesses—everything from a carwash and a car dealership to commercial real estate, restaurants, and agriculture. Being around that many business-savvy people gave Aaron the vision to make his own way, knowing that anything is possible through individual time and effort. 

With a natural aptitude for music, young Aaron decided to place his focus there. He studied piano at Roosevelt University, instrumental performance at Columbia College Chicago, and graduated from Chicago State University with a bachelor of arts in music education. While in college, Aaron decided to purchase a home for his mom, sister, and himself. It was during this process that his interest in real estate began.

“During that purchase [process] I was determined to learn real estate from the inside out, but only as an investor. I really had no desire to sell real estate,” shares Aaron. “But I also had a good buddy and long-time friend who had been selling and investing in our college years, and he was always telling me all the phenomenal things real estate was doing for him. It was his years of poking and prodding that made me finally decide to give it a try, and it was the best decision I ever made.”

In 2017, Aaron earned his real estate license and started as a REALTORⓇ. Not long after, his first significant challenges arose in both his personal and professional lives. Though he was going through a difficult divorce at the time, Aaron decided to switch brokerages. Both of these transitions were formative, and the difficult circumstances stretched him and showed him that his capabilities were beyond what he believed before.

“In the midst of those situations, I fought through limiting beliefs, self-doubt, fear, anxiety, depression, and victim syndrome so I could become who I was always meant to be,” says Aaron. “The leadership in our office and my mentors and team leaders helped me move from crawling to walking again.”

Aaron credits Frank Montro and Reginald Rawden for helping him regain his confidence in trusting in his ability to connect with people, lead others through challenges, and recall his business know-how. Even though it was tough, Aaron eventually was able to move from the fear of failure to embracing the challenges of the everyday and the rewards that come with doing so.

“The most rewarding part of my business has been to move from the fear of making it in real estate—a 100 percent commission-based career—to helping hundreds of people buy and sell real estate, all while becoming totally independent and taking care of a big family,” says Aaron. “I honestly didn't even think it was possible to do three deals a month when I started. I couldn't see myself not having to do music full-time with real estate only being able to be a side hustle for the rest of my life.”

Now in his seventh year as a full-time agent, Aaron is thriving. He’s now able to enjoy the daily grind while also prioritizing time with his three children—Nyeela (16), Aaron, Jr. (10), and Tyler (8)—as well as with his fiancée, Chelisa, a mother of four. “We are the modern-day Brady Bunch, or, as I like to call us, the Black Bunch,” says Aaron. His large family keeps him busy, but not too busy to still play music. Aaron’s faith has been another key source of strength throughout his life, so he has always made time to serve his church through his musical talents. 

Looking forward, Aaron hopes to continue growing his business while expanding his investment portfolio. As a next step, he also plans to produce more content about his journey so others might be encouraged to follow their own path down “the road less traveled.”

“In sharing my story, I hope that someone may see themselves and have renewed hope and drive for their real estate journey,” says Aaron. “Not only in seeing what I've accomplished, but in also seeing what it took for me to get here.”

“My advice is always to focus on the day and focus on the moment, not the struggle,” adds Aaron. “It is the small steps over time that lead to greatness.”