We interview Tom Liravongsa, aka “The Skyscraper Guy,” for an exclusive behind-the-scenes conversation inside the iconic Pittsfield Building — one of Chicago’s most storied and historically troubled skyscrapers.

In this episode, Tom breaks down how he acquired a 40-story, nearly 500,000 sq ft Chicago landmark for just $7.5 million — and why no one else had the vision (or nerve) to do it.

He walks us through the full playbook: adaptive reuse strategy, the capital stack, historic tax credits, zoning approvals, and how a massive social media following became his most powerful fundraising tool.

What you’ll learn: Why COVID created a once-in-a-generation window for skyscraper investing

How office-to-residential conversion actually works — and which buildings qualify Why pre-1935 buildings are uniquely suited for adaptive reuse

How 500K+ Instagram followers and hundreds of millions of views changed the financing game

The public space vision that banks said couldn’t be financed — until the waitlist proved otherwise What’s coming next: a K-12 school, urban farming, and a full city block project

Timestamps: 00:00 – Introduction & Pittsfield Building tour

01:30 – How the Skyscraper Guy was born out of COVID

03:45 – Buying a 500K sq ft skyscraper for $7.5M

06:20 – The capital stack & zoning approval journey

08:00 – Social media as a development strategy

14:00 – 228 existing apartments + 100 new luxury units

17:00 – Public observation deck & the banker problem

20:00 – Construction timeline & 2027-28 completion target

25:00 – Building a REIT from social media inbound investors

28:30 – What’s next: city blocks, schools, and urban farming

31:00 – From chicken farm to shaping Chicago’s skyline

Joe Smazal is a Commercial Real Estate Broker & Partner at Interra Realty.

Connect with the Skyscraper Guy: @SkyscraperGuy on Instagram & TikTok Subscribe to Real Estate Chicago Style for conversations with the investors, developers, and operators reshaping Chicago real estate. #ChicagoRealEstate #SkyscraperGuy #PittsfieldBuilding #AdaptiveReuse #RealEstateInvesting #ChicagoDevelopment #OfficeToResidential #RealEstatePodcast #HistoricPreservation #ChicagoLoop