Straight Up Chicago Investor

Straight Up Chicago Investor
  • 5.0 (298)
  • Investing
  • Updated Weekly

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.

  1. 4d ago

    Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months

    SUCI Co-Host Mark Ainley gives a presentation on his deals over the last 30 months at the WSBOA meetup!  Mark shares details on various deals including flips, BRRRRs, and even short-term rentals. He  explains how he sourced, financed, and stabilized these deals. He discusses biggest wins and top lessons learned. Mark closes the presentation with the biggest REI takeaways and a Q&A session that you won't want to miss! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Mark Ainley, GC Realty & Development Link: Mark's Instagram Link: WSBOA Meetup Guest Questions:  06:07 Housing Provider Tip - Understand root causes of water intrusion to efficiently solve issues. 08:11 Mark's first acquisition with Lantz! 16:18 Lessons learned on Mark's Hoffman Estates deal. 19:57 Home run BRRRR deal in Schaumburg! 27:56 Mark's syndication deal. 30:36 A quick flip in Downers Grove and FHA househack in Jefferson Park! 36:14 Flip deal in Hanover Park. 37:28 Rough deal in Elgin! 41:18 Mark's recent deal in Rolling Meadows. 42:37 Locking up a Downers Grove Ranch property. 44:38 Experimenting with a Short-Term Rental project! 47:13 Mark's key takeaways! 52:08 Q&A. 59:37 Chicago fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months

  2. 6d ago

    How the Government Can Stop Your Insurance Claim with Josh Steigelmann

    Can the government stop my insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    How the Government Can Stop Your Insurance Claim with Josh Steigelmann

  3. Jul 16

    Pat Hynes Is Bringing Transparency to the Cook County Assessor's Office

    Newly elected Cook County Assessor Pat Hynes joins us to share his plan for bringing fair, accurate, and predictable property assessments! Pat starts by discussing the flaws in the current property assessment system and his plan to improve and simplify the system! He shares an emotive story on why he decided to take on the county assessor role. Pat gets granular on common mistakes made on tax appeals and the methodology behind accurate valuations. He closes with insights on the Chicago Bears Stadium site selection and an extremely bullish outlook on Chicago! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Pat Hynes, Cook County Link: Pay Hynes - Lyons Township Page Link: The Devil in the White City (Book Recommendation) Guest Questions:  02:07 Housing Provider Tip - Review property characteristics on tax assessor's website to catch inaccurate info! 02:56 Intro to our guest, Pat Hynes! 11:06 Bringing transparency to property taxation. 17:02 An idealized property valuation approach. 21:47 Pat's motivation to take on the Cook County Assessor role. 27:08 Common mistakes made on property tax appeals. 29:19 The process for valuing condominium buildings. 30:40 Simplifying the appeal process! 39:04 Property tax incentives for providing affordable housing. 43:48 Pat's criteria for a successful term as Cook County Assessor! 45:15 Tax implications for the Chicago Bears Stadium site selection! 50:06 Data Center Taxation. 51:49 What is your competitive advantage? 52:04 One piece of advice for new investors. 52:32 What do you do for fun? 53:09 Good book, podcast, or self development activity that you would recommend?  53:26 Local Network Recommendation?  54:34 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Pat Hynes Is Bringing Transparency to the Cook County Assessor's Office

  4. Jul 9

    Ownership Fraud in West Town: Tom Shallcross and the $1.6 Million Fight to Unwind

    SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down a fraud story on a West Town property that he purchased! Tom dives deep into a recent purchase in West Town that involved ownership fraud when transferring title. He explains how the fraud was detected and how he navigated the process to reach a resolution. Throughout this show, Tom emphasizes the importance of being due diligence and having adequate insurance and documentation in place to protect yourself as best as possible! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Tom Shallcross, Co-host of Straight Up Chicago Investor Link: SUCI Ep 420 - Tom Shallcross Guest Questions:  01:38 Housing Provider Tip - Ensure drains are clear of debris or blockage to prevent issues during heavy rainfalls! 02:33 Intro to our guest, Tom Shallcross! 03:25 Intro to Tom's Fraud Property Story! 29:18 The process of clearing up title issues. 42:20 The stress associated with a fraud deal. 47:21 Managing partnerships when issues arise. 48:53 Chicago Fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Ownership Fraud in West Town: Tom Shallcross and the $1.6 Million Fight to Unwind

  5. Jul 7

    Inside Chicago's Proposed Rental Overhaul

    More Tenant Protections... Less Housing? Breaking Down Chicago's New RLTO ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser, NBOA Link: Amendment of Municipal Code Chapter 5-12 regarding Residential Landlord and Tenant Ordinance Link: Oppose Mayor Johnson's Proposed Ordinance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Inside Chicago's Proposed Rental Overhaul

  6. Jul 2

    Back Of The Yards Community with Ignacio Gonzalez

    Ignacio Gonzalez returns to discuss his Back of the Yards Coffee Shop development and his campaign for Chicago School Board! Ignacio jumps right in by sharing rent growth and property appreciation trends in the Back of the Yards neighborhood. He explains the struggles and lessons learned in completing the development of Dream Catcher Cafe. Ignacio talks about the impact of ICE raids in the neighborhood and the importance of contributing to community development and unity. He closes by explaining his motivation behind running for the Chicago Board of Education and shares how he would continue to positively impact the community if elected! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Ignacio Gonzalez of Chicago Board of Education Link: Dream Catcher Cafe Link: Beyond Legacy Homes Link: The Confessions of St. Augustine (Book Recommendation) Link: NAHREP Website Guest Questions:  01:34 Housing Provider Tip - Regularly check in with tenants to build rapport and promote communication. 02:32 Intro to our guest, Ignacio Gonzalez! 06:00 Rent growth and appreciation in Back of the Yards. 11:18 Navigating city inspections on a coffee shop development. 18:11 Lessons learned from Ignacio's coffee shop build out. 21:26 The impact of ICE raids in Back of the Yards. 24:36 Ignacio's campaign for the Chicago School Board. 40:51 What is your competitive advantage? 41:27 One piece of advice for new investors. 41:50 What do you do for fun? 42:35 Good book, podcast, or self development activity that you would recommend?  43:07 Local Network Recommendation?  44:14 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Back Of The Yards Community with Ignacio Gonzalez

  7. Jun 25

    Chicago Ground-Up Developments with Matt Katsaros

    Matt Katsaros of Wildwood Investments returns to break down ground-up development projects that he's taking down in Chicago! Matt jumps right in by explaining how his experience in commercial real estate brokerage and acquisitions led him to starting and scaling his development business. He dives deep into a Lincoln Park development deal and shares insights on raising capital, finding deals, and construction to successfully complete a development deal! Matt dives into the nuances of adaptive reuse projects and the process of securing tax increment financing (TIF) funds. Matt closes with tremendous tips on apartment layouts and characteristics that help maximize rents! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Matt Katsaros of Wildwood Investments Link: Matt's LinkedIn Link: SUCI Ep 109 (Matt's First Appearance on SUCI) Link: Real Estate For Breakfast Podcast Link: Spittin Chiclets Podcast Guest Questions:  02:00 Housing Provider Tip - Document apartment conditions prior to tenant move-ins. 04:25 Intro to our guest, Matt Katsaros! 10:37 Dissecting Matt's Lincoln Park development deal! 18:32 Tips for raising capital. 28:28 Breaking down an office-to-residential adaptive reuse deal.  37:58 The process to secure TIF funds. 44:18 Earning steady income between the disposition of developments. 46:13 Matt's outlook on his business and on Chicago. 50:27 Apartment characteristics that maximize rents! 62:33 What is your competitive advantage? 62:47 One piece of advice for new investors. 63:05 What do you do for fun? 63:35 Good book, podcast, or self development activity that you would recommend?  64:03 Local Network Recommendation?  64:26 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Chicago Ground-Up Developments with Matt Katsaros

  8. Jun 23

    "Who Should (and Shouldn't) Buy in Chicago Right Now?"

    Mark and Tom discuss the current fundamentals of the Chicago market with statistics provided by Jason Wagner. ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Tom & Mark, Straight Up Chicago Investor Podcast Link: Jason Wagner's Market Reports Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    "Who Should (and Shouldn't) Buy in Chicago Right Now?"
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About

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.

Information

  • Creator
    Straight Up Chicago Investor
  • Years Active
    2020 - 2026
  • Episodes
    469
  • Rating
    Explicit
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

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