Straight Up Chicago Investor

Straight Up Chicago Investor
  • 5.0 (297)
  • 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. Inside Chicago's Proposed Rental Overhaul

    7h ago

    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.

    16 min
  2. Back Of The Yards Community with Ignacio Gonzalez

    5d ago

    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.

    48 min
  3. Chicago Ground-Up Developments with Matt Katsaros

    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.

    1h 6m
  4. "Who Should (and Shouldn't) Buy in Chicago Right Now?"

    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.

    14 min
  5. North Side Neighborhoods and Market Opportunities with John Preston

    Jun 18

    North Side Neighborhoods and Market Opportunities with John Preston

    John Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago's North Side! John begins by discussing what it takes to build a successful brokerage business including early struggles before hitting his stride! He breaks down his process for reaching out to and converting seller leads and also explains the work brokers do that leads to a successful transaction. In typical SUCI fashion, John gets hyper-specific on neighborhoods that have seen great rent growth and areas where he sees investors putting their money! He closes with a bullish outlook on Chicago and emphasizes the importance of building market knowledge and networking to be successful in the game! 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: John Preston, Horvath & Tremblay | Email John: jpreston@hgapartments.com | Connect with John on LinkedIn Link: NBOA Chicago Guest Questions:  02:45 Housing Provider Tip - Understand catch basins and have a maintenance plan. 04:35 Intro to our guest, John Preston! 06:47 Getting off the ground as a real estate broker focusing on multi-family assets. 16:17 Troubling deals early on in John's career. 22:18 The work behind a successful listing. 29:30 Effectively following up with and converting leads! 31:27 How buyers can find opportunities in today's market. 34:57 John breaks down north side neighborhoods! 45:00 John's pick for a neighborhood with major upside! 50:17 John's bullish outlook on Chicago. 51:15 What is your competitive advantage? 52:15 One piece of advice for new investors. 53:04 What do you do for fun? 53:34 Good book, podcast, or self development activity that you would recommend?  54:23 Local Network Recommendation?  55:11 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.

    58 min
  6. Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)

    Jun 11

    Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)

    Tom and Mark interview some of Chicago's Brightest Real Estate Stars during a Renovo Networking Event featuring an interview of Thad Wong! Discussions range from areas investors are targeting in Chicago, breaking down the MRED and Zillow lawsuits, and lessons learned on luxury developments and operating apartment buildings. This show is full of wisdom from some of the best minds in Chicago Real Estate so have your notepad ready!  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 ============= Guests: Some of Chicago's Brightest Real Estate Stars during a Renovo Networking Event--including an interview with Thad Wong Link: Thad Wong Link: SUCI Ep 381 - Kevin Werner Link: SUCI Ep 255 - Eric Workman Link: SUCI Ep 368 - Joe Smazal and Ann Keilly Link: SUCI Ep 326 - RJ de Leon Link: Flora Blahnik Team Guest Questions:  03:17 Investing in Elgin with Mark Fostrom. 09:12 Renovo's formula to success with Kevin Werner! 17:18 Daniel Rosen discusses the evolution of Renovo. 26:23 Scaling a podcast and multi-family with Joe Smazal. 40:03 State of RE Brokerage with Luke Blahnik and Anthony Flora. 49:40 Luxury developments with RJ de Leon. 58:26 Renovation market in NW Indiana with Daniela Rodriguez. 66:22 Workman Lending Team's outlook on Chicago and business growth! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    1h 20m
  7. Proactive Tax Planning Advice to Save on your 2026 Tax Returns

    Jun 9

    Proactive Tax Planning Advice to Save on your 2026 Tax Returns

    What steps should I take to best prepare for my 2026 tax returns? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Aaron Zimmerman, Brick House CPAs Link: SUCI Episode 52 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.

    13 min
  8. Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan

    Jun 4

    Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan

    Asher Motew and Quinn Keenan of Essex Capital Markets break down keys to their early career success in the Chicago Commercial Lending Market! Asher and Keenan start by explaining their background coming from real estate families and how they've been able to pave their own path in commercial lending. They share their service offerings including creative solutions they bring that traditional lenders may not have. The duo talks about some successful deals and how those were put together while also explaining why their partnership has worked so well. They get tactical on underwriting expenses and NOI on deals to achieve desired lending outcomes. Through the show, Asher and Quinn showcase that being hungry and grinding has been the key to tremendous growth early on in their careers. 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 ============= Guests: Asher Motew and Quinn Keenan, Essex Capital Markets Link: Essex Capital Market's Instagram (@EssexCapitalMarkets) Link: Matt Feo (Essex Realty Group) Link: Asher Motew's Instagram (@AMo2.Cre) Link: Asher Motew's LinkedIn Link: Quinn Keenan's LinkedIn Guest Questions:  02:59 Housing Provider Tip - Understand and leverage cost segregation studies.  04:44 Intro to our guests, Asher Motew and Quinn Keenan! 13:20 Jumping into commercial mortgage brokerage. 21:20 The value offered by commercial debt brokers. 31:04 Breaking down a successful deal! 39:56 Asher and Quinn's complimentary partnership! 46:09 Biggest financing hurdles on deals! 50:54 Essex Capital Markets' role in the lending process. 61:10 Tactical tips on underwriting expenses and income. 66:36 What's next for Asher and Quinn. 69:18 What is your competitive advantage? 69:35 One piece of advice for new investors. 69:43 What do you do for fun? 69:52 Good book, podcast, or self development activity that you would recommend?  70:04 Local Network Recommendation?  71:27 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.

    1h 14m
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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
    465
  • Rating
    Explicit
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

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