Member Spotlight: Alex Wolking

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Our members are some of the most talented and hard-working real estate professionals in the business. After completing extensive training at our live or online trainings, Institute members are uniquely equipped with the skills and knowledge necessary to support affluent clients’ real estate needs.

To demonstrate just how exceptional our members are, we are introducing our “Member Spotlight” series. In this inaugural Member Spotlight, we talked to Institute member and recent Certified Luxury Home Market Specialist™ (CLHMS) Million Dollar Guild designee, Alex Wolking.

Alex has made a name for himself in both the Quad Cities area and Chicago. Starting at the age of twelve working for his father, he fell in love with the business and never looked back. In 2016, Alex moved to Chicago to sell real estate and quickly ranked within the top 200 agents in the city. Alex’s finesse, creative energy, and vast market knowledge have earned him numerous accolades such as “Rookie of the Year” for his previous REALTOR® association, HGTV’s Doory Award for 2013 “Best DIY Dream Home,” and countless others.  

Continue reading to get the full Q&A with Alex.

How did you get into the real estate business?

I had an interesting way into the business. I’m a second generation real estate agent. I started working for my dad when I was 12. I was fascinated by the business. Whatever it was, I just always wanted to be around my dad and what he was doing. I would go to open houses on my bike. I just loved the market and loved watching how it changed. I loved watching people succeed, and the role my dad played in helping clients achieve their goals.

I was licensed when I was 19 years old. About a year later, after going out on my own, I was doing research online one night. I wanted to learn how to break into the high-end real estate market and came across this organization called the Institute for Luxury Home Marketing. There was a training in Barrington, Illinois in two weeks, and I immediately signed up. At that point, I was a broke college student—I had nothing. I borrowed the money from my mom to take to the class and I drove to Barrington. I learned from Laurie Moore-Moore and took copious notes throughout the course. I loved what I learned and the tools, resources they provided to their members.

I left the class full of energy. My career changed. I doubled my business the next year and tripled it the year after that. I started getting listings that were the “challenging” listings. People would call saying, “we’ve had our house on the market for two years, and we hear you’re the guy to sell it. Can you help us?” And I sold it almost every time.

What are some of the challenges you face as a young real estate professional?

People often made the comment, “You’re too young.” What I realized was that they saw a young face, but they didn’t realize that I’d grown up working with my dad for seven years before that. I had to tell my story in a compelling way. I had a video made about me, what I do, what interests me about the business, and why people should list with me. The video has made a huge difference in telling my story. People don’t care about what you know until they know how much you care.

Having a niche also helped. When I sold in the Quad Cities, I focused primarily on historical homes. It was the ongoing joke in that market that, “if it is over 100 years old and over 4,000 square feet, chances are Alex Wolking either listed it, sold it or showed it five times.” When I came to Chicago, no one knew who I was. However, I was able to say, “here are properties I’ve sold in the past that had been a challenge for previous agents.” Being able to market that experience has been extremely helpful. Results tell a story all their own!

What’s your favorite thing about selling high-end real estate?

When I get the call, “We have a unique house and it is going to be a challenge, are you interested?” The answer is usually yes! Growing up in the theatre, you’re taught to “just go with it.” Selling a unique house is about finding the story and setting it free. I help people find their castle big or small, I sell them all. I love getting a weird property and creating a story around it.

How do you keep up with current and former clients?

One of the tools I will live and die by are the Institute’s reports and market stats. I send those to my clients and they find that valuable. Those tools position you as the market expert. You can drive a Mercedes and wear a nice blue suit, but if you don’t know your market, no one’s going to work with you. I found that that’s my strong suit: I’m authentic, genuinely care, and I thoroughly enjoy what I do. Being a nerd has served my clients well!

In your experience, what is the difference between working in the upper-tier real estate market compared to the more traditional market?

You have to demonstrate value and show you know the market exceptionally well. These are sophisticated clients and often know the “relevant properties” better than most agents because they oftentimes personally know the sellers of those homes. You have to articulate the value of each property, and explain market conditions. Your marketing plan has to be on point. My philosophy in everything I’ve done is make it so the client doesn’t have to think. Thinking two steps ahead of them every single step of the process and taking care of issues before they arise is what creates clients for life.

Can you describe a particularly difficult listing and how you approached it?

I recently had a unique listing on 32 acres. It was listed at $1.2 Million. It was a tough property because not many people in the area could afford that price, nor were there any comps to go off of. We did a drone video to show the acreage. I knew the eventual buyer was likely a local business owner, so I looked for people who owned more than 25 acres, and/or were members of the Chamber of Commerce, and sent them brochures. That was a trick that I learned from the Institute – how to connect the dots and “sacrifice” parts of the market to find the right buyers. This buyer came along with their agent and said, ”Oh yeah, we got that postcard from you in the mail with the ATV parked outside.” We finally closed on it six weeks ago. It sold for $993K. It was the highest recorded sales price ever in that county.

What advice do you have for people wanting to break into the high-end real estate market?

The best pieces of advice I ever got was so simple: go make friends. That’s all networking is—making friends. Find something you’re passionate about and follow that path to where high-net-worth people are. For example, I love old houses. I found a historical preservation non-profit, Landmarks Illinois. They have an organization called the Louis Sullivan Society which is their group of top donors. Once a year I plan walking tours of historic homes for sale in certain historic districts throughout the city, exclusively for that group. It’s an amazing networking opportunity. It’s not a hard sell, but more of a way to connect and say, “oh, by the way, I also happen to sell real estate.” They appreciate that I’m not trying to hard sell them. I’ve made some great friends. I am also an arts and theatre nerd, so I recently got involved with Young Professionals Networks through Chicago Symphony Orchestra, Lyric Opera, and other theatre companies. I go to their young professional’s events, attend fundraisers with their high-end donors, etc. It puts me in those circles without spending a fortune on country club memberships. It’s something I’m passionate about, and I get to meet people interested in the same things. Real estate is supposed to be fun. Work that’s fun gets done!

How has the Institute for Luxury Home Marketing influenced your career?

The Institute gave me a skillset and really helped hone my abilities and talent in a way that is fun and meaningful. I use everything I learned from the Institute every single day. I have my course manual from seven years ago, and I still refer back to it.

Learn more about Alex at



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