Straight Up Chicago Investor

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! ============= 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: 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

What are recent legal updates to the 2026 lease and new squatter laws? ============= 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 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.

Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock's downtown redevelopment plan and also speaks to city corridors with development opportunities. Jessica explains "infill" sites, metrics for successful developments, and strategic planning of developments to allow for future adaptive reuse. Throughout the show, Jessica demonstrates a passion for sustainable developments that enhance the quality of life for the residents of Woodstock! 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: Jessica Erickson, City of Woodstock Link: Jessica's LinkedIn Link: Woodstock Comprehensive Plan Link: The Prof G Pod (Podcast Recommendation) Link: Heartland Realtor Organization (Network Referral) Guest Questions: 02:13 Housing Provider Tip - Utilize water shut off valves at vacant properties to prevent issues! 03:52 Intro to our guest, Jessica Erickson! 09:14 Jumping into Economic Development in Woodstock, IL. 16:50 Woodstock's downtown redevelopment plan. 23:44 Breaking down "infill" sites. 25:54 Measuring successful developments. 29:28 Redevelopment opportunities in Woodstock. 31:27 Future-proofing development sites. 38:41 Closing remarks on the upside of Woodstock! 43:12 Woodstock's competitive advantage? 43:39 One piece of advice for new investors. 44:33 What do you do for fun? 44:55 Good book, podcast, or self development activity that you would recommend? 45:48 Local Network Recommendation? 46:16 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.

Do you need a HELOC on your investment property? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Benjamin Stef, NEXA Mortgage 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026! Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ryan gets granular on latest foreclosure statistics and provides his outlook on the REO market heading into 2026. He closes with his take on Chicago's crime problem and the neighborhoods that he is bullish on! 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: Ryan Smith, RE/MAX Properties Link: Ryan's Instagram Link: SUCI Ep 70 - Ryan Smith Link: SUCI Ep 28 - Ryan Smith Link: The Chicago Way (Podcast) Link: DAWGS Vacant Property Security Guest Questions: 02:05 Housing Provider Tip - Understand manufacturer warranties on appliances and reconsider extended warranties! 04:15 Intro to our guest, Ryan Smith! 10:47 Risks associated with buying properties at the auction. 13:12 Understanding properties in receivership. 15:55 Expectations on REO transactions! 25:15 Key Foreclosure Statistics! 35:54 Ryan's outlook on the foreclosure market. 42:55 Promising south and west side neighborhoods. 46:19 Solving Chicago's largest issues. 47:20 What is your competitive advantage? 48:12 One piece of advice for new investors. 49:20 What do you do for fun? 49:50 Good book, podcast, or self development activity that you would recommend? 50:45 Local Network Recommendation? 51:51 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.

Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance! Jonathan starts by explaining partnership pitfalls to avoid based on recent changes within his business. He gets vulnerable by discussing a multifamily investment on Chicago's southside that involved various evictions and a $400,000 fire caused by a problem tenant! Jonathan shares tips on the mindset required to weather business storms and turns to more positive news by discussing some large renovation projects that his company is working on. He closes with how he has leveraged networking to skyrocket his business and shares his plans for continued growth going into the new year! 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: Jonathan Klemm of Quality Builders Link: Founders (Podcast Recommendation) Link: SUCI Ep 250 - Jonathan Klemm Link: SUCI Ep 206 - Prashanth Mahakali Guest Questions: 02:07 Housing Provider Tip - Perform adequate due diligence specifically as snowy conditions are present! 03:44 Intro to our guest, Jonathan Klemm! 06:50 Partnership pitfalls to watch out for. 15:10 Jonathan's scary "fire" deal! 29:41 Mindset for getting through a difficult deal. 42:41 Large renovation projects by Quality Builders. 48:26 Leveraging BiggerPockets to grow a business. 50:36 Jonathan's 5 Year Outlook! 53:20 What is your competitive advantage? 54:00 One piece of advice for new investors. 54:31 What do you do for fun? 54:38 Good book, podcast, or self development activity that you would recommend? 55:32 Local Network Recommendation? 56:51 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.

Is now a good time for me to purchase in Chicago? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets! Alec explains how he transitioned from the corporate real estate world to a more entrepreneurial position at Base 3 Development. He describes how he "stretched" out of his comfort zone by jumping into a 6-unit gut rehab project off the bat and shares lessons learned! Alec shares insights on large residential development projects including zoning, underwriting, and leasing considerations. He closes with tips on leveraging VAs and off-shore staffing solutions for optimal property management while also providing a 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: Alec Greenberg, Base 3 Development Link: Staffolio Website Link: Chicago Cityscape Website Link: EUBA - NBOA Chicago Link: SUCI Ep 412 - Luke Helliker Link: On The Road (Book Recommendation) Guest Questions: 02:13 Housing Provider Tip - Understand lease changes coming in 2026! 03:13 Intro to our guest, Alec Greenberg! 08:32 Lessons learned from Alec's first gut rehab project. 13:54 Jumping into a 48-unit development. 22:25 Tips for leasing in the off-season. 25:26 Underwriting rules of thumb on large developments. 35:43 Leveraging VAs and other tools for property management. 49:16 Alec's outlook on Chicago! 51:57 What is your competitive advantage? 52:23 One piece of advice for new investors. 52:39 What do you do for fun? 53:02 Good book, podcast, or self development activity that you would recommend? 53:43 Local Network Recommendation? 55:18 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down everything you need to know about architectural plans and permits in Chicago! Tom discusses when you need plans and permits for a project and when it's appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons learned on design and functionality particularly on luxury redevelopments! He closes with insights on dormer additions and considerations for ADUs and historic district remodels that will add to your permit approval timeline! 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, Straight Up Chicago Investor Link: SUCI Ep 235 - Tom Shallcross Guest Questions: 02:32 Housing Provider Tip - Understand 2026 leasing law changes regarding minors on leases! 04:33 Intro to our guest, Tom Shallcross! 05:35 The process of developing plans and permitting. 14:11 Top design and functionality mistakes! 16:16 Must-have amenities in luxury remodels. 20:40 Timeline for creation of architectural drawings. 27:23 The role of expeditors. 35:29 Design considerations for dormer additions. 41:40 What do you do for fun? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.