Real Estate Chicago Style Podcast

Joe Smazal

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

  1. Nate Ernst on Adaptive Reuse & Why Chicago's Downtown is Just Getting Started

    10/20/2025

    Nate Ernst on Adaptive Reuse & Why Chicago's Downtown is Just Getting Started

    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.

    1h 11m
  2. Regina Stilp on Chicago Development, Mag Mile Revival & $4.9B in Projects

    10/06/2025

    Regina Stilp on Chicago Development, Mag Mile Revival & $4.9B in Projects

    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: 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.

    1h 4m
  3. Chicago's Affordable Housing Needs An Overhaul - Guest: Collette English-Dixon

    09/21/2025

    Chicago's Affordable Housing Needs An Overhaul - Guest: Collette English-Dixon

    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.

    1h 1m
  4. Building A $300M Portfolio | The good neighbor unpacks his 25-year experience investing, having fun, & giving back - Ron Abrams

    08/19/2025

    Building A $300M Portfolio | The good neighbor unpacks his 25-year experience investing, having fun, & giving back - Ron Abrams

    Join host Joe Smazal for an entertaining and insightful conversation with Ron Abrams, owner of Silver Property Group and one of Chicago's most successful multifamily investors. With over 25 years in real estate and 30+ years as an attorney, Ron has built an impressive portfolio of 1,500+ units across 120+ buildings throughout Chicago's north and northwest sides. 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.

    1h 12m

Ratings & Reviews

5
out of 5
17 Ratings

About

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

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