5 MINUTE READ -- Meet Tom Liravongsa, better known as The Skyscraper Guy, and discover how he's helping restore Chicago's iconic Pittsfield Building while sharing the stories that keep the city's architectural history alive.
From Medical Offices to Modern Living
The Pittsfield Building, one of Chicago's most iconic skyscrapers, is entering a new and exciting chapter. That's right! Tom Liravongsa, better known as the "Skyscraper Guy" on social media, is the Managing Partner of the Landmark Collection. Tom and his team are helping write the next chapter of the historic Pittsfield Building. Built in 1927 in just 11 months, the Pittsfield Building formerly housed the most dentists' and doctors' offices in one central location in the world. Now? Tom and his team are bringing this 100-year-old, 38-story icon back to life as new residential apartments.

We had the chance to interview Tom to learn more about his journey and the process of restoring the Pittsfield. Read the full interview below.
Q&A with the Skyscraper Guy
Q: Please introduce yourself and what you do.
A: My name is Tom Liravongsa, better known as the @Skyscraperguy on social media, and I’m a real estate investor and preservationist.
Q: What made you want to buy the Pittsfield Building and take on the project of restoring it?
A: Opportunity and timing. This building has probably seen 30 or more buyers in the past 15 years, and no one made a move. Then COVID happened, and prices adjusted, allowing my investors and me to enter Chicago at the right prices and give the Pittsfield the attention it deserves, hence the preservationist aspect.
Q: What is something people wouldn’t know about the Pittsfield building?
A: It was built in 11 months!
Q: What made you want to document your journey on social media?
A: Timing. There was no “Skyscraperguy” anywhere else in the world and I saw it as an opportunity to claim the name and allow me to showcase this beautiful building and the architecture in Chicago.
Q: As a Loop building owner, why is the Loop worth investing in, and how do you see the Loop evolving over the next five years?
A: It’s important for people to remember this isn’t rural farmland America, meaning sometimes you buy a house or land out in the middle of nowhere, and in 10 years, it’s still worth pretty much the same price. The Loop was a bustling area with an incredible number of people and businesses. This is an opportunity to restructure the city and bring those people back, double what it was before. And that’s often done through housing. So, looking out over the next five years you’ll see that we aren’t the only ones doing this; others are seeing the vision and also participating. We may be doing the most regarding housing, but there are so many supporters wanting to bring the Loop back to life because density can only increase, which means: more people, more things to do, and more places to go.
Q: Do you have any other projects you are working on?
A: Yes. A majority of which are in Chicago, specifically in the Loop, because when you buy a skyscraper, you don’t necessarily look at that one skyscraper and say, "That’s it. I’m done; That’s all I need". You have to consider the thousands of people you’re asking to live in your building, and now you have to provide them with things to do. So, the best way to give them things to do is to invest in more than just one skyscraper; you must invest in retail, restaurants, and entertainment. That's why we’ve acquired many different properties here in the Loop for that purpose. These concepts are being built out, and we want it to be a surprise.
Q: Where can people find you on social media?
A: Your classic socials are the best places. Instagram has my largest following, but you can also find me on TikTok, Facebook, etc. There’s also a YouTube channel where we are making longer-form videos. All under "Skyscraperguy".
We want to thank Tom, aka @Skyscraperguy, for being this month's "People of the Loop" profile! To watch the video version of this segment, click here. Follow the Skyscraperguy on social channels here.
