Real Estate Chicago Style Podcast

Joe Smazal
  • 5.0 (19)
  • Investing

Host Joe Smazal interviews the most prominent real estate developers and players in the ever-changing Chicago Real Estate Cityscape.

  1. Sep 18

    The "Five T's" of Development & Why Timing Beats Location | Leon Walker D3 Realty PT2

    Part 2 of Joe Smazal's conversation with Leon Walker, Founder & CEO of DL3 Realty, goes deal by deal. When Target closed both of its South Side stores, the city refused to let it sell to the usual disposition list. One alderman knew somebody. That call became the Blue Cross Blue Shield center in Morgan Park, 500 jobs, ribbon cut in masks six feet apart, and then the Discover (now Capital One) center that doubled it to 1,000. Leon explains the design trick he borrowed from a failed senior housing deal to make a dark big box work as office space, and why "venture tenants" are the ones willing to see it before it exists. We also get into why the hardest part of building a grocery store is building a grocery store - vertical integration, long-term supply contracts, Chicago's produce terminal advantage, and what it actually took to walk Jewel executives through Woodlawn in person. Plus the 25-acre West Pullman industrial assembly on the former Plano Manufacturing site, and two downtown projects: ACODA at Pritzker Park and the 135 S. LaSalle conversion of the Field Building, on the ground where the first skyscraper stood. Leon closes with the Five T's he gives emerging talent: talent, timing, team, treasure, and truth. And why the last one is the only thing that carries you through a deal that might not work. Chapters 00:00 Revitalization vs. gentrification 01:59 Pre-COVID, the "retail apocalypse," and reading durable trends 04:35 Target leaves the South Side, and the city blocks the sale 07:40 Solving the dark big box: courtyards and light wells 11:30 Discover doubles the model to 1,000 jobs 12:20 Why nobody built a grocery store for 50 years 16:38 Selling Jewel on Woodlawn in person 18:41 Whole Foods, Englewood Square, and the 10 tenants that followed 19:53 West Pullman: 25 acres and 400,000 sq ft of industrial 24:30 Downtown, ACODA and 135 S. LaSalle 28:04 What makes an office-to-residential conversion actually work 33:02 The Five T's 38:48 Why he loves Chicago 42:48 Getting the city back over 3 million

    The "Five T's" of Development & Why Timing Beats Location | Leon Walker D3 Realty PT2

  2. Sep 18

    From Neighborhood Impact to Downtown Transformation | Leon Walker from DL3 Realty

    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.

    From Neighborhood Impact to Downtown Transformation | Leon Walker from DL3 Realty

  3. Jul 27

    Building $200M Worth of Luxury Chicago Homes - Barrett Homes

    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.

    Building $200M Worth of Luxury Chicago Homes - Barrett Homes

  4. Jun 24

    From $500 Receivership to 850 Units: How the Motew Brothers Built MO2 Properties

    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!

    From $500 Receivership to 850 Units: How the Motew Brothers Built MO2 Properties

  5. May 16

    Chicago's Stockyards Revival - The New Generation of Warehouses From a 4 Generation Business

    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

    Chicago's Stockyards Revival - The New Generation of Warehouses From a 4 Generation Business

  6. Apr 16

    From Chicago Board of Trade to The Salt Shed. Meet Chicago's Most Creative Developers: R2

    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

    From Chicago Board of Trade to The Salt Shed. Meet Chicago's Most Creative Developers: R2

  7. Mar 17

    How One Guy Bought a Chicago Skyscraper for $7.5M (And What Happens Next)

    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

    How One Guy Bought a Chicago Skyscraper for $7.5M (And What Happens Next)

  8. Feb 23

    Chicago's Real Estate Secrets: Why Investors Are Coming Back (2026 Market Forecast) EUBA

    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).

    Chicago's Real Estate Secrets: Why Investors Are Coming Back (2026 Market Forecast) EUBA
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Ratings & Reviews

5
out of 5
19 Ratings

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Host Joe Smazal interviews the most prominent real estate developers and players in the ever-changing Chicago Real Estate Cityscape.

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