Podcast

By Mark Ainley

Episode 107: Lessons From a 300k Rehab on My Near West Side Househack with Alex Martinez

You may have already listened to our househacking from hell episode (Episode 89). Today, we don't have tenants stealing cars or anyone overdosing, but we do have typical obstacles faced with a first-time househack; all compounded with the fact that this project included...

By Mark Ainley

Episode 106: Restoring Pilsen’s Old World Architecture Since 1998 with Gordy Payne

From toilets falling through ceilings, to gentrification, Gordy Payne has seen it all as a hands-on owner in Pilsen. Gordy took a chance on Pilsen due to its proximity to downtown and made a name for himself for his ability to restore beautiful vintage buildings. He fully committ...

By Mark Ainley

Episode 105: Straight Up Tues Tip 17 - Sharad Mehta

What are tactical steps to follow when sending, responding, and tracking mailers?

By Mark Ainley

Episode 104: From Unpaid Intern to Running the City of Chicago’s Building Department

Today, Tom and Mark have an excellent conversation with Judy Frydland, who served as the commissioner of buildings for the City of Chicago from 2015-2020. A lot happened under her leadership including the streamlining of the permit process to make it simpler and more efficient th...

By Mark Ainley

Episode 103: How to Handle Mold in Chicago with Greg Bukowski and Devin Renberg

MOLD! It’s the scary four-letter word that investors never want to hear and it does not belong in a healthy property. However, a basic understanding of mold and its misconceptions in the marketplace will make you a better investor. After having a bad experience with a ...

By Mark Ainley

Episode 102: Straight Up Tues Tip 16 - Sharad Mehta

How do I pull information and begin a direct mailing campaign?

By Mark Ainley

Episode 101: Investing in Will County: Mokena, Frankfort, and New Lenox with Jason Marcordes

Will County is one of the fastest growing counties in Illinois, and when compared to Cook County, it offers a faster growth rate and a lot more room for development and expansion.As a second generation property manager and investor, Jason Marcordes from Landmark Property Manager,...

By Mark Ainley

Episode 100: A Group of Straight Up Chicago Investors Celebrate The Live Recording of Episode 100

In our first live recording, we celebrate 100 episodes by asking questions to the audience (see how many answers you know) and also answering multiple questions from attendees. We discuss our favorite parts of the podcast, lessons learned from interviewing multiple Chicago r...

By Mark Ainley

Episode 99: Straight Up Tues Tip 15 - Jared Kott

What are some tips on how to best screen workforce housing tenants?

By Mark Ainley

Episode 98: What is Happening to Chicago Property Taxes?

As this episode airs, several of the Chicago townships have already been reassessed, leaving many owners with an unpleasant increase in property taxes. Returning guest Tim Jacobs of KSN Law (appeal.tax), joins us to discuss what he’s seen in the Chicago townships that have ...