CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

Most real estate investors finish tax season, take a breath, and immediately stop thinking about taxes for the next nine months.That is usually a mistake.Tom and I sat down with Aaron Zimmerman from Brick House CPAs to talk about what investors should be doing now to prepare for their 2026 tax returns. The big takeaway was simple: tax planning is not something you do in December. By then, some options are already gone.If you want to sav...

Real estate isn’t always spreadsheets, clean comps, and smooth closings. Sometimes it’s buying land for $800 because you just need to own “something.” Sometimes it’s driving to another state because you didn’t think about the time zone change and the recorder’s office closes in one minute. Sometimes it’s paying $30,000 for a boiler… to heat one unit… for one non-paying tenant...

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...

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...