314 Episodes

  1. Episode 162: Property Management in Chicago’s Southside with Tim Harstead

    Published: 8/25/2022

  2. Episode 161: How financing for Chicago Non Conforming units just got easier.

    Published: 8/23/2022

  3. Episode 160: Comparing Chicago To Several Midwest Markets with Brian Kochendorfer

    Published: 8/18/2022

  4. Episode 159: From Successful BRRRR to Major Project Hurdles in Chicago’s Western Suburbs with Zach Gring

    Published: 8/11/2022

  5. Episode 158: Straight Up Tues Tip 34

    Published: 8/9/2022

  6. Episode 157: Investing in Chicago Midterm Rentals with Rishi Bajaj

    Published: 8/4/2022

  7. Episode 156: A Decade of Grinding and Succeeding on Chicago’s Northside with Joe Smazal

    Published: 7/28/2022

  8. Episode 155: Straight Up Tues Tip 33

    Published: 7/26/2022

  9. Episode 154: Scaling From a Duplex to a $100 Million Portfolio in Chicago’s North and Northwest Side with Jeff Weinberg

    Published: 7/21/2022

  10. Episode 153: Building Wealth via Long-Term Real Estate Investments in Chicago with Bill Himmelstein

    Published: 7/14/2022

  11. Episode 152: Straight Up Tues Tip 32

    Published: 7/12/2022

  12. Episode 151: Dissecting Property Taxes on your Chicagoland Properties with Cook County Assessor Fritz Kaegi

    Published: 7/7/2022

  13. Episode 150: Mastering Multi-Family to Propel Your Chicagoland Investments with Rod Khlief

    Published: 6/30/2022

  14. Episode 149: Revitalizing the “Land of Lincoln” with Aurora Mayor (and potential IL Governor) Richard Irvin

    Published: 6/23/2022

  15. Episode 148: Acquiring Distressed Real Estate by “Beating the Streets” in Chicago with Joe Sevcik

    Published: 6/16/2022

  16. Episode 147: Straight Up Tues Tip 31 - Perry Farella Breaks Down HUD 203k Loan Options

    Published: 6/14/2022

  17. Episode 146: How To Manage Your Rehabs and What to Look For In a Chicagoland General Contractor with RJ DeLeon

    Published: 6/9/2022

  18. Episode 145: NFL Tight End Turned Chicago Real Estate Investor with Matt LaCosse

    Published: 6/2/2022

  19. Episode 144: Straight Up Tues Tip 30 - Perry Farella Provides Numbers on a Recent Purchase and Rehab Projects He Financed

    Published: 5/31/2022

  20. Episode 143: Ins and Outs to Navigating Chicago Short-Term Rentals with Jessica Ryan

    Published: 5/26/2022

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Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.