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

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

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).

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.

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:

• How Canvas built relationships with brands like Sweet Green, Louis Vuitton, and top restaurant groups
• The 11-year journey to bring Toca Madera to Chicago's Fulton Market
• Inside details on the massive $7 billion United Center development project (1901 Project)
• Why location isn't everything—it's service, service, service
• The art of curating neighborhoods and why the right tenant matters more than the highest rent
• How Fulton Market still has major growth ahead with 10,000+ residential units planned
• Career advice: "If you don't love it, get out now"

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.

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.

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:

• Bronzeville Lakefront - The 48-acre mixed-use redevelopment of the former Michael Reese Hospital site, navigating three mayoral administrations and community engagement
• Sola Michigan City - A 252-key Renaissance Hotel with 188 condos/townhomes bringing new life to the Indiana lakefront
• 1308 North Elston - Farpoint's new office in a converted light factory with unobstructed city views
• Southeast Expansion - Building industrial projects along the I-85 corridor, including a facility that brought 150 jobs to rural Alabama
• Working with communities and navigating public-private partnerships
• The current state of Chicago development and capital markets
• Why the "Chicago is dangerous" narrative frustrates her
• Advice for young professionals entering real estate

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.

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.

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.

What You'll Learn:

• How Ron transitioned from practicing law to building a 1500 unit real estate empire
• Why he shifted from value-add renovations to acquiring larger, stabilized properties
• The secrets behind his successful equity raises with Chicago investors ($22M and $45M deals)
• His contrarian take on Chicago property taxes and why he thinks we've been "under-taxed"
• How vertical integration (brokerage, leasing, property management, construction) gives his team a competitive edge
• Why he believes Chicago neighborhoods are poised for an "explosion"

Episode Highlights:

• Ron's creative LLC naming strategies (including the legendary "Jackass" partnership)
• His 9-to-5 work culture philosophy and focus on work-life balance
• Mentorship advice: "Go for it" - why low barriers to entry make real estate accessible
• The importance of replacement cost analysis in today's market
• Behind-the-scenes look at running 2,000+ units with a tight-knit team

About Ron Abrams:

Ron Abrams is the founder of Silver Property Group, a vertically integrated real estate company specializing in Chicago multifamily properties. Known for his straightforward approach, Ron has built lasting relationships with tenants, investors, and industry professionals while maintaining a reputation for transparency and fairness. When he's not yelling across the office to his team (in the most endearing way), you might find him coaching basketball or attempting Pilates.

Interested in Chicago multifamily investment opportunities? Connect with Joe Smazal for expert brokerage services on the north side.

Since founding Blueprint in 2013, Ben has driven the company's rapid growth and innovative approach, leveraging deep market expertise and analytics to lead over 800 transactions valued at more than $15 billion.

With nearly two decades in the seniors housing and care industry, Ben shares his vision for healthcare real estate, leadership philosophy, and how Blueprint is elevating the market through collaboration and data.

Based in Chicago, Blueprint is recognized as the #1 most active real estate advisor in seniors housing and care over the past decade.

In this episode, Jonathan shares:

The inspiration behind launching The Neighborhood Hotel in 2020.

How he merges historic architecture with contemporary design across Chicago neighborhoods—Lincoln Park, Little Italy, and soon West Loop—and in Michigan.

His philosophy of “lasting luxury”: thoughtful amenities, local partnerships, and a home-away-from-home vibe Stories behind the design choices—from heirlooms turned art to custom blankets and curated coffee experiences.

The brand’s commitment to community giving and its mission to elevate every stay.

His mission? Offer “lasting luxury”—quality craftsmanship, suite kitchens, premium linens, curated bath products, and coffee makers—all layered with local flair.

Each property preserves historic elements (like the former Italian‑American Sports Hall of Fame in Little Italy) and partners with local artisans—from The Heirloomist and The Weaving Mill—to infuse spaces with personality and neighborhood identity.

Beyond hospitality, Jonathan fosters community well-being.

In 2022, The Neighborhood Hotel pledged 5% of profits to Chicago charities like the 100 Club of Illinois, supporting first responders and families

Subscribe for more: entrepreneurship, hospitality design, and insider stories. #JonathanGordon #NeighborhoodHotel #BoutiqueHotel #Chicago #Entrepreneurship

A third-generation realtor and lifelong Chicagoan, Matt has built a reputation for his deep knowledge of the city’s neighborhoods, relentless work ethic, and commitment to professionalism.

In this episode, we dive into the lost art of professionalism and determination, exploring how Matt’s journey from starting with zero clients to becoming Chicago’s #1 top-producing agent was fueled by grit, discipline, and a passion for his craft.

Matt shares candid insights on what it takes to stand out in today’s competitive landscape, the habits that drive his success, and why professionalism still matters more than ever.

Whether you’re in real estate or any field, this episode is packed with lessons on perseverance and the value of doing things the right way.

Don’t miss this masterclass in determination from one of the hardest-working men in Chicago real estate.

Kevin, recently named CEO of the Year by the National Private Lenders Association, shares insights on how Renovo has expanded from a Chicago-based startup founded in 2011 to a national powerhouse with local lenders in over 15 markets across the country and over $10B earned.

Renovo's motto is "We lend where we live" and they process hundreds of loans weekly in the areas they serve.

Discover how Madison Rose has breathed new life into commercial properties, earning accolades like the 2018 NAIOP Chicago Award for Excellence for a landmark Walgreens lease at the Old Post Office.

Matt shares insights on navigating the evolving office market, his passion for philanthropy through the Madison Rose Foundation, and innovative strategies that have raised over $490,000 for Casting for Recovery.

Becovic is a family-owned real estate firm with deep roots in Chicago's North Side. Since taking the helm in 2003, Sal has expanded the company's portfolio from 400 to over 2,000 units, emphasizing community investment and sustainable growth .

In this episode, Sal shares:

The importance of doing as much yourself you possibly can and immersing yourself in the real estate, living among residents, etc.

The importance of building solid fundamentals and surrounding oneself with great people.

The importance of incentives for landlords to deliver quality to their residents.

Whether you're a seasoned investor or new to the real estate scene, Sal's experiences and strategies offer valuable lessons on navigating the Chicago market.

Connect with Sal Becovic: Website: becovic.com

Joe Smazal: jsmazal@interrarealty.com

Steven Caban: steven@fullbarsmedia.com

Don't forget to like, comment, and subscribe for more episodes featuring industry leaders and innovators!

Cross-streets goal is to add value at every step of the multi-family process, from design and branding, to leasing with a high-level of service.

His old school approach is more person-to-person rather than relying on automation.

In this episode we talk about new apartment and amenity trends and the finer points of leading a large leasing team.

Joe Smazal - Interra Realty jsmazal@interrarealty.com

Produced by Steven Caban - Full Bars Media steven@fullbarsmedia.com

Joe Smazal - INTERRA REALTY

jsmazal@interrarealty.com

Produced by Full Bars Media

steven@fullbarsmedia.com

But he slowly came to the realization that by starting his own property management company (an unpopular decision) and combining his ability to develop investor relationships, he was able to scale his business to managing over 10,000 units. 

Now Peak manages some of Chicago's largest residential buildings, and has scaled to over 200 employees.

In this episode we dive into his humble beginnings and what he looks for in a building as an investment. 

Over the years he has grown the team and earned numerous accolades on INC and Chicago Crain's Fast 50, among others.

Tooday we talk about his journey from litigation attorney to finding his true passion in creating relationships with investors, developing new talent, and developing software tools that provide formative investing education.