CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

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...

In the latest episode of the Straight Up Chicago Investor Podcast, hosts Mark Ainley and Tom Shallcross dive into the world of house hacking with guest Brendon Heneks of Team Facchini at Fairway Mortgage. Alongside his agent Sarita Scherpereel, Brendon shares his journey of purchasing his first multi-family property and offers invaluable insights for both new and seasoned investors.Jumping on the Right OpportunityBrendon begins by discu...