Podcast

By Mark Ainley

Episode 59: Chicago’s Very Own Cost Segregation Expert - Kevin Cawley

The word taxes inspires fear from all types of investors, but especially in Chicago. From income tax, to property tax, we’re paying a lot. Depreciation is one of Real Estate’s greatest benefits, and there is a way to maximize that benefit immediately. Cost Seg Kev is ...

By Mark Ainley

Episode 58: Multi Family Investing in Chicago’s Northwest Side with Gloria Weikert

One of the most important allies to an investor is the broker they work with. Gloria Weikert runs the X-Plus team and has a specialty in helping clients buy investment properties. In today’s episode, Gloria gives some insight on what it takes to win deals in a competitive m...

By Mark Ainley

Episode 57 (Tuesday Tip 1) - Eric Workman

How Are Investment Deals Structured?

By Mark Ainley

Episode 56: Fighting for Good Chicago Housing Policy with Kris Anderson

Chicago is known for complex and restrictive landlord and tenant policies, but there are dozens of people fighting for change and protection. Kris Anderson of the Chicago Association of Realtors is one of those people on the front lines. Not everyone knows the role of CAR, so Kri...

By Mark Ainley

Episode 55: Understanding The Diverse Opportunities and Multiple Pockets of Elgin

Elgin has a long history of being one of the most significant cities located just outside of Chicago. Spanning two counties and one of the largest populations in Illinois, it offers a wide variety of housing options and investment strategies. Broker and investor, Mike Zwemke, tak...

By Mark Ainley

Episode 54: Traveling West of the West Loop, and Other Areas of Chicago that Top Producing Agent Lum...

Lumi Ispas has been a determined and successful investor, broker, and coach in Chicago for two decades. She’s lost it all and gained it all back. In today’s episode she shares her journey of emigrating from communist Romania to truly experiencing the American Dream th...

By Mark Ainley

Episode 53: CHA Section 8 Roundtable - Part 1

Many fear what they don’t understand. That’s exactly why we put together this round table discussion with two other great CHA section 8 property managers. Listen in as we address the entire workflow from screening the applicants, to the move in, and everything that ha...

By Mark Ainley

Episode 52: Saving Thousands of Dollars With the Appropriate Tax Strategy and Deductions

It’s March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the i...

By Mark Ainley

Episode 51: Becoming "Brick Rich" on the Northside; Owning 74 Doors by Age 29

Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago’s largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of m...

By Mark Ainley

Episode 50: Building a Chicago Empire with Andrew Holmes

For our 50th episode we thought we’d give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few inve...