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Straight Up Chicago Investor

Straight Up Chicago Investor

By: Straight Up Chicago Investor
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About this listen

 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.Copyright of Straight Up Chicago Investor 2021. Career Success Economics Personal Finance
Episodes
  • Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs

    Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
    Jan 29 2026

    Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions.

    Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Markets Tax Credits. Throughout the show, Darryl demonstrates his deep knowledge in Tax Credits and conveys how it can be a super powerful tool for investors who know how to leverage it!

    If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content!

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    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

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    Guest: Darryl Jacobs, Ginsberg Jacobs

    Link: Sonny Ginsberg (Network Referral)

    Link: SUCI Ep 26 - Neal Bawa

    Guest Questions:

    01:49 Housing Provider Tip - Ensure proper transfer of utilities when purchasing a property to avoid outages!

    04:09 Intro to our guest, Darryl Jacobs!

    13:26 Understanding Opportunity Zones.

    25:04 Opportunity Zones 1.0 vs 2.0!

    32:14 New Markets Tax Credits.

    54:48 Other tax credit resources for investors.

    59:55 What is your competitive advantage?

    62:48 One piece of advice for new investors.

    64:11 What do you do for fun?

    64:37 Good book, podcast, or self development activity that you would recommend?

    65:33 Local Network Recommendation?

    66:02 How can the listeners learn more about you and provide value to you?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.
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    1 hr and 9 mins
  • Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley

    Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley
    Jan 27 2026

    What are recent legal updates to the 2026 lease and new squatter laws?

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Mark Ainley, Straight Up Chicago Investor Podcast and GC Realty & Development LLC

    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

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.
    Show More Show Less
    14 mins
  • Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon

    Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
    Jan 22 2026
    Jake Fugman and Mike Scanlon of The Axon Group return to forecast Chicago's Real Estate Market in 2026! Jake and Mike kick things off by reflecting on their 2025 predictions including office space leasing trends, downtown sales stats, and impacts of the Northwest Side Preservation Ordinance. The duo then make their 2026 predictions with topics ranging from ADU Zone expansion to creative mortgage solutions to help with affordability. Jake and Mike close out with an outlook on interest rates and the future of real estate based on recent brand mergers! 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: Jake Fugman & Mike Scanlon, The Axon Group Link: The Axon Group Instagram Link: SUCI Ep 354 - 2025 Predictions with Jake and Mike Link: SUCI Ep 398 - Paul de Luca Link: With Roam Website Link: The Almanack of Naval Ravikant (Book Recommendation) Guest Questions: 01:13 Housing Provider Tip - Don't get stuck in analysis paralysis and take action in 2026! 02:46 Intro to our guests, Jake Fugman and Mike Scanlon! 04:10 Reflecting on 2025 bonus depreciation predictions. 07:51 Office vacancy trends in 2025. 11:43 Impacts of the Northwest Side Preservation Ordinance. 19:53 Chicago Loop and downtown sales stats! 24:20 Real estate predictions in 2026! 33:48 Expansion of the Chicago ADU Zones. 42:12 Where are mortgage rates going? 50:16 Real estate brand consolidations. 61:40 What is your competitive advantage? 63:45 One piece of advice for new investors. 65:32 What do you do for fun? 66:01 Good book, podcast, or self development activity that you would recommend? 67:33 Local Network Recommendation? 69:42 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.
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    1 hr and 14 mins
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