Real Estate Chicago Style Podcast

Leon Walker, Founder & CEO of DL3 Realty, joins host Joe Smazal to break down 25 years of development work on Chicago's South Side — and the framework behind it.

Leon went from a junior partnership at LaSalle Partners/JLL, with a Singapore assignment on the table, to coming home after his father's death to build in the neighborhoods he grew up in. Since then DL3 has created 3,000+ jobs with another 10,000 in the pipeline, delivered the first new family housing Englewood, Woodlawn, and South Shore had seen in 40-50 years, and brought back national retail, banking, and primary care to communities that had gone decades without.

We get into his venture development model and the five factors every deal has to clear: historically successful location, nearby anchor institution investment, readily available land or buildings, early green shoots, and deliberate local leadership. Plus why "cost per unit" is the wrong way to judge affordable housing, how housing functions as an economic development platform, and why a weekly in-person team meeting still beats anything on a screen.

Chapters
00:00 Intro & rapid fire
02:00 Integrity, creativity, professionalism
04:39 AI tools vs. the weekly deal task force
10:25 Growing up on 71st & Stony Island
15:44 Leaving corporate to start DL3
20:03 The first deal: 21% prime and a national bank in Roseland
25:00 Being a Black-owned firm in a 2% industry
26:30 What DL3 actually stands for
28:17 Balancing profit and impact
32:26 The five factors of venture development
38:26 The Thrive brand: Woodlawn, Englewood, South Shore
47:42 The cost-per-unit critique, answered

Part 2 coming soon.

Mike Barrett co-founded Barrett Homes with his brother John in 2005 - right into the teeth of the downturn.

Twenty years later they've delivered 40+ single family homes and 115+ multifamily homes worth over $200 million across Chicago's North Side.

We recorded inside their Armitage & Sedgwick building, a former CVS Mike turned into six oversized condos that sold from $2.2M on.

Mike walks through how the off-market deal came together, why a 72-foot lot with only six units was the right call, and the proprietary sound mitigation system they built after lightweight concrete kept failing on footfall noise.

Also covered:

Why buyers research a toaster longer than their home, and how Barrett built a brand around fixing that.

The entitlement grind: a year of rezoning, community meetings, and one project cut 40% from the original unit count.

Why brokers bring them off-market land, and what "easy to work with" is actually worth.

Their Smith Park deal, found by driving past a closing auto parts store. TOD ordinance changes, the case for upzoning every Dash 2 to Dash 3, and what Western Ave's buildout proved.

Design calls that aged well (clay kitchens, warm neutrals) and one that didn't (soapstone — don't).

Why they've never left Chicago.

Hosted by Joe Smazal, multifamily broker at Antero Realty and owner-operator at Smaz Apartments.

Joe Smazal sits down with Kenny and Michael Motew of MO2 Properties — two brothers who've quietly built one of Chicago's most active middle-market multifamily operations to ~850 units across ~80 buildings, while staying relentlessly hands-on.

They get into how the business has evolved from six-flat walk-up rehabs into ground-up new construction and adaptive reuse (office-to-resi, a church conversion, a West Loop deal), why ground-up surprised them by being easier, and the 691 new-construction project that took 5+ years and four parcels to assemble.

The conversation covers their decision to double down on Chicago when others fled post-COVID, the realities of raising deal-by-deal investor money versus a fund, a down-zoning fight on Logan Boulevard and how they resolved it by actually sitting down with the city, and why communication is their #1 retention tool.

They share hard numbers on the current market (67% retention, 5%+ on renewals, 8% on new leases), why Logan Square is outperforming, and candid advice for young investors trying to buy their first building today — plus a reminder that AI has its place, but they still go through every single lease renewal by hand.

Finally we preview one of their latest buildings in the heart of West Town!

Joe Smazal sits down with Barry Misner (CEO, Misner Group) and Larry Goldwasser (Executive VP, CBRE) inside a brand-new industrial building in Chicago's Union Stockyards — the geographic center of the city and one of the most constrained, high-barrier industrial submarkets in the country.

Barry leads a third-generation, 81-year-old development firm with over 750 projects and $3B+ in completed work. Larry has 25+ years and 650+ transactions specializing in industrial land and redevelopment across Chicago, Western Cook, O'Hare, and Northwest Indiana.

Together they break down why modern infill industrial is so hard to deliver — and why only a handful of developers in the city can actually pull it off.

In this episode:

Why the Union Stockyards is an A+ industrial submarket and how it's transforming

What separates a modern industrial building from the 1970s stock most tenants are stuck in (clear height, column spacing, truck courts, power, sprinkler systems)

Land scarcity, environmental cleanup, soil conditions, and the new Chicago air quality ordinance

Why industrial rents in Chicago are up 175% over the last decade

Build-to-suit vs speculative development, and why 58% of new construction is now

BTS Northwest Indiana maturing as an industrial market — and the $27B data center investment in Hobart and New Carlisle

The real story behind NIMBYism against industrial and data centers

Why Chicago's economic diversity keeps the industrial market steadier than markets like Houston

Up-and-coming Chicago real estate talent worth watching

A great listen for developers, brokers, investors, and anyone trying to understand how the buildings that supply the city actually get built. Real Estate Chicago Style is hosted by Joe Smazal, multifamily broker and owner-operator on Chicago's north side.

#ChicagoRealEstate #IndustrialRealEstate #CRE #Stockyards #ChicagoDevelopment

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.