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 ...

Welcome to another Straight Up Chicago Investor Podcast! In this episode, we bring back Corey Oliver, founder of Strength in Management, to dive deep into the current challenges and evolving opportunities of investing and operating in Chicago’s most underserved neighborhoods. Managing nearly 700 units on the South and West sides of Chicago, Corey offers a candid, boots-on-the-ground perspective on how to build resilient rental po...

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...

Kevin Schnell shares his journey from grinding it out as a young broker to becoming a partner at Concord Capital, transacting over 1,500 units and owning hundreds of apartments throughout Chicago. From humble beginnings knocking on industrial doors to building a powerful network and launching his own real estate venture, Kevin’s story highlights grit, resourcefulness, and smart investment strategy.This episode is packed with pract...

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...

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...

In a compelling episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross welcome back Jared Kott, a seasoned real estate investor, to reflect on his transformative 10-year journey from corporate America to full-time real estate. Jared shares invaluable insights, hard-earned lessons, and some thrilling adventures, making this episode a must-listen for anyone involved in or considering a career in real est...

In the latest episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross dive into the innovative world of container homes with special guest Rory Rubin, the founder of S.I. Container Builds. As housing affordability continues to be a pressing issue, Rory sheds light on how her company is providing a high-quality, cost-effective solution by repurposing shipping containers into livable homes.A Unique Backgr...

The final walkthrough is a vital step in any real estate transaction, serving as the buyer's last chance to inspect the property before closing. As emphasized by Chance Badertscher, this walkthrough is not just a formality; it’s an essential safeguard for buyers to confirm that the property is in the condition agreed upon in the contract. It's also an opportunity to ensure that all repairs negotiated during the attorney re...