Matt Garrison and Zach Cupkovic, co-founders of R2 Companies, sit down with host Joe Smazal for a rare and wide-ranging conversation about how they built one of Chicago's most iconic real estate portfolios: from student housing at Purdue during the financial crisis to the Salt Shed, the Chicago Board of Trade, and a growing loft office empire acquired at reset basis while everyone else was running.

They break down their two core strategies - Chicago Loft and Urban Flex - and explain why 30% vacancy is actually a lagging indicator, how they leased 850,000 square feet of office in 2025, and why owning buildings within three miles of your office beats the Wall Street institutional playbook every time.

This episode covers: Matt's origin story: from Coldwell Banker desk-hopper to #1 Coldwell Banker agent worldwide in 2006 How buying distressed student housing in 2008 set the template for everything that followed

The TILC meat grinder problem in office - and how R2 is engineering around it

The West Loop portfolio: losing a deal, buying back the note for $18.5M, and why 50%+ of original investors came back in

The full Salt Shed origin story - bats, flashlights, and a German private equity company that loved their brand

Why Urban Flex is the asset class nobody has named yet

What Ralph Lauren taught Matt about real estate

If you're in Chicago real estate - or just want to understand how the best operators actually think - this one's worth your full attention.

Subscribe for more conversations with Chicago's most influential voices in real estate, development, and investment.

Real Estate Chicago Style with Joe Smazal

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

The 2026 Edgewater Uptown Builders Association (EUBA) annual forecast brought together four Chicago real estate insiders spanning across development, property management, leasing, and sales, for a candid conversation about where the market is headed — and why Chicago might finally be having its moment.

Key takeaways:

No supply = rent growth. Downtown delivered just 145 units in 2025. Class A rents are up ~9% YoY, Class B up 7.5%.

The neighborhood market is following suit.

The ripple effect is real. Renters priced out of the West Loop are moving to Old Town, then Lincoln Park, then Edgewater/Uptown — creating demand across the board.

Chicago vs. the Sunbelt. Markets like Nashville and Austin are seeing rent declines while Chicago rents climb.

Investors who fled are coming back. Affordability isn't as bad as the headlines suggest. At Chicago's minimum wage, a two-income household can find a 2BR for ~$2,000/month in viable neighborhoods.

Biggest risks ahead: Rising expenses squeezing NOI, potential rent control legislation in Springfield, and a wave of adaptive reuse supply possibly hitting in 2027–2028.

Featuring Ron Devries (Integra Realty Resources), Joe Root (East Superior Real Estate Partners), Tyson Schutz (Apartment Source), and Joe Smazal (Interra Realty). Hosted by Ron Abrams (Silver Property Group).

In this episode of Real Estate Chicago Style, host Joe Smazal sits down with two powerhouses: Adam Friedberg, CEO of Mavrek, and Matt Wilke, Managing Partner of LG Group.

Together, these two firms represent over $3.5 billion in real estate value and thousands of residential units.

Instead of the "old guard" secrets and cut-throat competition, Adam and Matt discuss a new era of transparency and collaboration.

They reveal exactly what is in their pipelines—from office-to-residential conversions on Wacker Drive to massive 700+ unit projects in Phoenix—and why diversification is the only way to survive a shifting market.

What You’ll Learn in This Episode:

Market Predictions: Why "Build-to-Rent" (BTR) is the hottest asset class and the risks involved with 30-year exits.

The Chicago Advantage: Why Chicago’s concrete trades and union labor are significantly faster than those in Nashville or Columbus.

Affordability vs. Luxury: A candid look at why "luxury" housing is the only way to drive down overall rents in the city.

Diversification Strategy: How to balance high-rise development with boutique neighborhood projects and construction services.

Career Advice: Why "picking up the phone" is still the #1 competitive advantage for young professionals today.

In this episode of Real Estate Chicago Style, host Joe Smazal sits down with Chicago residential heavyweight Jeff Lowe of the Lowe Group at Compass, on location in a 3,000 sq ft authentic loft conversion in the West Loop. With nearly $5 billion in career sales volume, Jeff breaks down how he built one of the most productive residential practices in the city, why he still genuinely enjoys the grind, and what it really takes to stay at the top of the game for two decades.

Join host Joe Smazal for an insider's look at Chicago's high-end retail real estate with Elan Rasansky, partner at Canvas Real Estate. Discover how a boutique brokerage competes with national giants like CBRE and JLL while representing the world's top luxury brands and restaurant groups.

In this episode, Elan reveals:

Elan also shares his favorite pizza spots (Pizza Michi, Vito Nick's, Zarella), why Chicago beats New York for food, and the importance of dropping your ego in deal-making.

Recent recognition: Crain's Chicago Business 40 Under 40

Perfect for real estate professionals, entrepreneurs, and anyone passionate about Chicago's neighborhoods and dining scene.

In this episode of Real Estate Chicago Style, host Joe Smazal sits down with Nate Ernst, founder and principal of Envoi Partners, to discuss his journey from acquiring distressed properties in the wake of the Great Financial Crisis to developing over 520 residential units in Chicago's Loop.

Nate shares the story behind founding Ernst Development Company post-2008, where he acquired and repositioned over 40 properties before partnering with attorney and capital markets expert Corey Faulkner to form Envoy Partners.

The conversation dives deep into their philosophy of adaptive reuse—taking underutilized assets and transforming them into spaces that communities love.

Key Topics Discussed: The meaning behind "Envoy Partners" and their focus on being the "finishing touch" in neighborhoods

Why North Damon and Milwaukee intersection embodies what Chicago is all about

The massive opportunity in Chicago's Loop, with 2,000+ apartments planned and retail following rooftops

How Envoy approaches user experience as the core of their development strategy

The importance of hiring team members with "clear minds and full hearts" like James Armour Real estate as the ultimate entrepreneurial experience—starting from $350K or even working in buildings to learn operations

Why "you can't change the wind, but you can change the direction of your sails" The power of seeing projects clearly without letting fear or self-doubt take over

Swimming in Lake Michigan as a reset and the incredible energy of Chicago's bridges over the river

About Nate Ernst:

Nate is driven to restore and build apartments and retail that set the bar for user experience.

His career has been defined by tackling projects not suited for every investor.

At Envoi Partners, he's responsible for all aspects of the development process and asset management, including their flagship 200,000 square foot project at 19 South LaSalle.

About Real Estate Chicago Style:

Join host Joe Smazal as he interviews Chicago's top real estate investors, developers, and operators.

Joe is an investment sales broker at Interra Realty and owner-operator of small apartments on the north side.

Each episode explores what makes Chicago one of the best cities to live, invest, and build.

Subscribe for weekly conversations with the people shaping Chicago's real estate landscape.

Join us for an insightful conversation with Regina Stilp, founding principal of Farpoint Development, one of Chicago's most innovative real estate development firms. Since co-founding Farpoint in 2016, Regina has spearheaded development projects totaling $4.9 billion across the Midwest and Southeast, including transformative Chicago landmarks.

In This Episode:

Regina shares her journey from traveling the world (Japan, London, adventure tours across America) to becoming a key player in Chicago real estate. Starting at Sterling Bay in 1996 when it was just four people, she helped grow the company through landmark projects including Google's first Midwest headquarters at 1000 West Fulton and McDonald's global headquarters at 400 South Jefferson.

Key Topics Discussed:

Regina's philosophy centers on community engagement, creating economic impact, and maintaining an abundance mindset in a competitive industry. Her projects span from high-profile urban developments to industrial facilities creating meaningful employment in rural communities.

Connect with Farpoint Development to learn more about their portfolio of transformative projects across Chicago and the Southeast.

Join host Joe Smazal for an in-depth conversation with Collette English Dixon, Executive Director of the Marshall Bennett Institute of Real Estate at Roosevelt University and the first African American woman to lead a higher education real estate program in the US.

In this episode, Colette shares her remarkable journey from accidentally stumbling into real estate at a college job fair to becoming a leader with 30+ years of investment management experience at PGIM Real Estate (Prudential Financial). She discusses:

️ How Chicago compares to other major markets - "all the things New York has without the hassle"

️ The critical difference between "Affordable Housing" and "affordable housing" and why semantics matter

Why LIHTC projects costing $750K+ per unit are unsustainable and need systemic reform

The importance of industry organizations like CREW Network for career development Diversity, equity and inclusion in real estate - beyond just "checking boxes"

Building your personal brand and relationship network in the industry

Colette also previews her upcoming podcast "Brick, Grass and Steel" focusing on how the built environment impacts communities, and shares why she believes Chicago is one of the world's most dynamic cities.

Whether you're starting your real estate career, working in affordable housing, or interested in Chicago's development landscape, this conversation offers valuable insights from a true industry pioneer.

In this episode, we sit down with Tom Sitz and Cody Huntertmark from Cushman & Wakefield, one of the world's largest commercial real estate services firms, to dive deep into their professional journeys and get an insider's look at high-stakes commercial real estate.

What We Cover:

How Tom and Cody built their careers and landed at a top-tier commercial real estate firm.

The unique challenges and opportunities in commercial real estate Behind-the-scenes insights into major deal-making processes

The career defining Google building deal in Chicago

What it takes to succeed in commercial real estate at the highest levels Industry trends and what's shaping the future of commercial property

Whether you're interested in commercial real estate, considering a career in the industry, or just love hearing about major business deals, this conversation offers valuable insights from professionals working at the pinnacle of their field.