CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Today we’re joined by Nate Fernandez, also known as "Real Estate Nate"—a full-time W2 employee, father of three, CRM consultant, and Chicago landlord with over 20 units. If you think you’re too busy to build a real estate portfolio in Chicago, this episode will absolutely change your mindset.From balancing family life to building systems that scale, Nate walks us through how he created a cash-flowing Chicago ...

Today, we’re bringing back Mike Procaccio for his third appearance on the show. Mike’s our trusted accountant and one of the most valued members on our Build Your Team page. If you’re a Chicago landlord or house hacker—especially one managing your own multi-unit—you’ll want to take notes on this episode.We dig into one of the most overlooked areas of owning a multi-unit property: how house hacking aff...

Michael Kaplan joins us to share his inspiring journey from a young broker struggling to make ends meet to scaling his real estate business and building a rental portfolio in the Chicago area. His story reflects grit, persistence, and strategic decision-making that any aspiring investor or broker can learn from.Michael opens up about his decision to leave college during the pandemic and dive into real estate full-time. He breaks down th...

What does it really mean to build a lifestyle around real estate investing in Chicago? In this episode of the Straight Up Chicago Investor Podcast, Erik Swanson walks us through his unique journey from audio engineer, touring with world-famous bands like Aerosmith and Green Day, to full-time real estate investor and bar owner. If you’ve ever asked, "Can I escape my 9-to-5 and live life on my terms through real estate?" t...

This episode was different!  In this live recording from the NSBC (Northwest Side Building Coalition) event, real estate powerhouses Joe Smazal and Ann Reilly join the Straight Up Chicago Investor Podcast to break down the latest leasing and sales trends in Chicago's apartment market. Whether you're a landlord, investor, broker, or property manager, this candid conversation sheds light on how properties are trading, what re...

Jeffrey Ma may have started out in his family’s restaurant business, but his mindset, discipline, and grit have transformed him into a rising force in Chicago real estate. In this episode, Jeffrey shares how the lessons learned in his family’s restaurant helped shape his real estate investing career, from building systems and automating processes to managing guilt, culture, and family obligations along the way.This one&rsquo...

When you hear the words “$20 million portfolio,” most people imagine someone in the game for decades. But for Wyatt Simon, that success came in just a few years—through grit, strategy, and a lot of BRRRR deals. In this episode, Wyatt joins us to talk about how he used the BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) to scale a massive portfolio in a short period, and the systems he created to make it sustainable...

Eric Workman, one of the most frequent guests on the Straight Up Chicago Investor Podcast, returns to break down something that’s often overlooked—but absolutely vital—in the real estate game: your credit score. This episode dives deep into the small credit missteps that can create large financial consequences for Chicago property managers, investors, and anyone looking to scale in real estate.From missed $30 payments ...

Sabrina Wottreng Shares How To Leverage Public Relations To Grow Your Real Estate BusinessIn the latest episode of the Straight Up Chicago Investor Podcast, Sabrina Wottreng, a seasoned Chicago-based publicist and "Friend of the Pod," shares her insights on how public relations (PR) can supercharge a real estate business. Sabrina’s company specializes in the real estate sector, assisting Chicago-area real estate teams in...

Debt Service Coverage Ratio (DSCR) loans are a type of commercial loan product that evaluates a property's cash flow to determine its ability to cover its debt obligations. Eric Workman breaks down the fundamentals of DSCR loans, explaining how they have evolved from a simple qualification point to a robust tool for real estate financing.Key Components of DSCR Loans:Calculation of DSCR: The DSCR is calculated by dividing the propert...