“'Go make friends’ was the best advice I've ever been given,” says Alex Wolking, REALTOR® at Keller Williams ONEChicago.

Back when he was nineteen, Alex was about to call it quits as a REALTOR®, but top agent Deb Haussmann intervened. “She told me not to give up, that I’d be great,” recalls Alex. “She said, ‘Forget “networking.” Go make friends.’ One year to the day, I won the Quad City Area REALTOR® Association’s Rookie of the Year award.” 

“Always say yes to an invitation with new people. Go to the fundraiser or committee meeting when you don't feel like it. Get involved with your community,” he advises. “There are so many interesting people out there waiting to meet you, and you will love getting to know them.”

Using that mindset as a north star, Alex has built a successful real estate business with a powerful niche that’s rooted in community and authenticity. Raised in the Quad Cities, Alex was drawn to real estate early. He was just twelve years old when he began working for his REALTOR® father. While other kids were riding their bikes to the park, Alex was pedaling to open houses.
 

“I begged my mom to take me to my first open house but she wouldn't, so I just went by myself on my bike,” he shares. “From that day on, I couldn’t get enough. I had lots of questions.”

That insatiable curiosity propelled him forward. Alex earned his bachelor’s degree in business and real estate from DePaul University. The coursework—steeped in law, finance, and commercial development—gave him a broad foundation and ability to understand the industry from every angle. Though his education wasn’t sales-focused, it equipped him with the strategic thinking that would define his approach to real estate. 

“It was excellent training in understanding the industry from another perspective,” Alex says.

After college, he took a leap of faith and moved back to Chicago without knowing a single soul. The comfort of his small, tight-knit hometown and thriving business, was gone. What remained was a vision and the drive to build something meaningful. 

“I had to leave the comfort zone of my hometown to start all over again in a city where I knew no one,” Alex says. “I hustled for years.”

Instead of buying leads, Alex built relationships by following his “go meet friends” mantra and created his own version of a small town in a big city. He became a fixture in his Uptown neighborhood, volunteering and serving on the boards of local organizations including the Uptown Chamber of Commerce, Buena Park Neighbors, Friends of Brennemann (which supports Brennemann Elementary School), and the Uptown Chicago Commission. He now also sits on the board of Landmarks Illinois, a statewide historic preservation group.

“My business was built through philanthropy, hyperlocal neighborhood involvement, and marketing,” he says. “I have never bought a single lead. I built my business the old-fashioned way.”

Alex also leaned on the skills he learned from growing up in the theatre—his father performed regularly in local productions—particularly storytelling and creative problem-solving. Alex credits his time working onstage, backstage, and front of house (customer service) with shaping his leadership and communication style. 

“Growing up in theatre taught me how to think on my feet; how to be empathetic, how and when to take the lead and when to follow, and do both collaboratively, always prioritizing the best interests of the show and audience,” he says. “But most importantly, how the energy backstage [e.g., at the office] translates to what happens onstage [e.g., with clients].”

Today, that mindset extends to his director of operations, Kevin Brannon. Alex says they operate with the efficiency of a four-person team, despite it being just the two of them.

“If I’m the surgeon, he’s the nurse,” Wolking says. “We finish each other’s sentences. Kevin is so much more than ‘just an assistant.’ I see him as a partner in my business.” 

Their partnership has powered their strongest year yet, along with their highest average sale price to date. 

So what continues to drive Alex now? The challenge of new opportunities.

Alex has become known for tackling listings others find tough, like homes with unusual architecture, historical properties, or homes that have been sitting without offers. “That’s where my theatre training plays out really well,” he notes. “I know how to look at every angle, think outside the box, and find a new way to tell the home’s story to elicit genuine feelings of connection—that’s when the offers come in.” Alex’s approach is also practical, methodical, and deep. 

“We prep our listings for the market like it’s the Olympics,” he says. “We know everything about that property, down to the last time the furnace filter was changed.”

When he's not working, Alex immerses himself in Chicago’s vibrant culture—walking the lakefront, catching Broadway shows, checking out local architecture, and even offering free summer sidewalk tours of Uptown’s mansion districts. 

Looking forward, Wolking’s goals are as grounded as they are ambitious. He plans to grow his team to four people, with a vision of hitting $100 million in annual sales. But he never wants to get away from the tight-knit, people-focused, humble culture he’s built.

“Getting to do what I want, when I want to, is ultimate freedom,” he says. “We don't gloat about our accomplishments. We just get the job done.”