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Straight Up Chicago Investor

Business & Economics Podcasts

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.

Location:

United States

Description:

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.

Language:

English


Episodes
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Episode 434: Interesting Lease Renewal Statistics and Strategies with Mark Ainley

2/24/2026
What are the common mistakes made when handling lease renewals? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty 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.

Duration:00:13:51

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Episode 433: Chicago Building Code Violations with Zack Limbaugh

2/19/2026
Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Throughout the show, Zack provides insights on handling various code violation scenarios to give you an edge against the competition! 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: Zack Limbaugh, The Limbaugh Law Firm Link: Zack's LinkedIn Link: SUCI Ep 333 - Zack Limbaugh Link: SUCI Ep 79 - Gary Davidson Link: Essentialism (Book Recommendation) Guest Questions: 02:35 Housing Provider Tip - Understand the true costs of not allowing pets in your rentals! 04:44 Intro to our guest, Zach Limbaugh! 10:23 Buying a property with code violations. 16:48 Lending considerations for violations exist. 23:52 Protecting yourself against fines for code violations! 31:03 Ensuring violations are found during due diligence. 43:15 Common violation tickets to watch out for! 50:35 Crazy code violation stories! 51:17 What is your competitive advantage? 51:32 One piece of advice for new investors. 51:39 What do you do for fun? 51:51 Good book, podcast, or self development activity that you would recommend? 52:03 Local Network Recommendation? 52:18 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Duration:00:54:34

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Episode 432: Strategic Chicago House Hacking with Zach Posey

2/12/2026
Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required! 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: Zach Posey, Chicago Multifamily Club Link: Chicago Multifamily Club Meetup Link: Wisdom Takes Work (Book Recommendation) Link: SUCI Ep 52 - Aaron Zimmerman Link: SUCI Ep 326 - RJ de Leon Guest Questions: 01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals! 03:57 Intro to our guest, Zach Posey! 07:38 Starting off with a 4-unit house hack. 17:25 Acquiring a second house hack in Roscoe Village. 26:28 Property Management tips for house hackers! 28:44 Leveraging assumable loans to make the numbers pencil. 34:41 The value of networking events. 37:40 Zach's REI goals and outlook on Chicago! 42:42 What is your competitive advantage? 43:13 One piece of advice for new investors. 43:35 What do you do for fun? 43:50 Good book, podcast, or self development activity that you would recommend? 44:40 Local Network Recommendation? 45:39 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.

Duration:00:49:44

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Episode 431: What You Need To Know About Real Estate Professional Status with Mike Procaccio

2/10/2026
What is real estate professional status and why is it important for investors? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Michael Procaccio, Pro Financial Services Group Inc 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.

Duration:00:17:32

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Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer

2/5/2026
Reed Meyer, founder and managing broker at Lease312, shares top tier leasing advice and how connecting with mentors has propelled his real estate journey's growth at such a young age! Reed starts off by detailing the process of acquiring his first property; a 3-unit house hack in Logan Square. He talks about purchasing an industrial warehouse and flipping it for double the price in just 45 days! Reed shares golden insights on apartment listing marketing, leasing, and tenant expectations in prime North Side neighborhoods. To conclude, Reed gives a 5 year outlook on his business goals and Chicago's residential rental market! 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: Reed Meyer, Lease312 Link: Reed's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: SUCI Ep 259 - Sal Becovic Link: SUCI Ep 22 - Matt Fritzshall Link: SUCI Ep 51 - John Westbrook Link: Gabe Horstick (Network Referral) Link: Zeckendorf Autobiography Guest Questions: 01:56 Housing Provider Tip - Get great pictures, get floor plans, and be responsive to optimize leasing of apartments! 03:15 Intro to our guest, Reed Meyer! 06:45 Reed's first house hack. 11:37 The nuances of industrial property investing. 16:40 Reed's transition from corporate to real estate full time! 22:12 Top leasing mistakes by landlords. 29:15 Jumping into a 5-unit house hack! 34:00 Tenant expectations in Lakeview. 40:50 Outlook on the Chicago leasing market and rent growth! 42:52 Reed's 5 year business outlook. 45:43 What is your competitive advantage? 45:53 One piece of advice for new investors. 46:10 What do you do for fun? 46:54 Good book, podcast, or self development activity that you would recommend? 47:26 Local Network Recommendation? 48:08 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.

Duration:00:50:31

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

1/29/2026
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! ============= 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.

Duration:01:08:47

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

1/27/2026
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.

Duration:00:14:07

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Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon

1/22/2026
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.

Duration:01:13:36

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Episode 426: Reshaping Suburban Woodstock with Jessica Erickson

1/15/2026
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.

Duration:00:49:14

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Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options

1/13/2026
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.

Duration:00:17:04

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Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith

1/8/2026
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.

Duration:00:55:00

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Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm

1/1/2026
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 2025.

Duration:00:59:10

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Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market

12/30/2025
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.

Duration:00:08:32

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Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1

12/25/2025
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.

Duration:00:58:12

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Episode 420: The Chicago Permitting Process with Tom Shallcross

12/18/2025
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.

Duration:00:45:48

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Episode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley

12/16/2025
How do I navigate the rent determination process for Section 8 applicants in Chicagoland? ============= 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.

Duration:00:12:50

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Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords

12/11/2025
Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation! Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don'ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and shares horror stories caused by those mistakes! He closes best practices to handle squatters and an outlook on potential changes to the eviction process. 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: Zeke McDonald-Lewis, Erwin Law Link: Zeke's LinkedIn Link: SUCI Ep 330 - James Erwin Link: Red Rising (Book Recommendation) Guest Questions: 03:50 Housing Provider Tip - Plan tenant payment plans to clear balances quickly! 05:51 Intro to our guest, Zeke McDonald-Lewis! 12:25 First step in dealing with a non-paying tenant. 19:54 Next steps after serving a 5-day notice. 34:18 Timelines for the eviction process. 38:36 Top eviction mistakes. 44:43 Eviction horror stories! 47:25 Dealing with squatters. 51:01 Zeke's outlook on the eviction process! 55:02 What is your competitive advantage? 55:54 One piece of advice for new investors. 56:31 What do you do for fun? 56:59 Good book, podcast, or self development activity that you would recommend? 57:15 Local Network Recommendation? 58:00 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.

Duration:01:00:40

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Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal

12/4/2025
Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings! Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares details on his first 2-unit building in Logan Square and dives deep into top "gotchas" when purchasing 2-4 unit buildings. He closes with a bullish outlook on Chicago particularly the areas surrounding the United Center! 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: Niko Apostal, Niko Collaborative - Essex 312 Link: The ONE Thing Podcast Link: The Power of Full Engagement (Book Recommendation) Link: SUCI Ep 112 - Chicago Cityscape Guest Questions: 01:58 Housing Provider Tip - Be sure to appeal property taxes particularly with upcoming reassessments! 03:36 Intro to our guest, Niko Apostal! 08:41 Weathering the storm of the real estate crash! 20:53 Lessons learned and tips for starting a real estate brokerage. 30:25 Investing in a 2-unit in Logan Square. 42:00 Essex 312 vs Essex Realty Group. 48:50 Gotchas when buying a 2-4 unit building! 52:10 Neighborhoods that Niko is bullish on! 60:20 5 Year Outlook on Chicago. 62:24 What is your competitive advantage? 63:11 One piece of advice for new investors. 63:27 What do you do for fun? 63:39 Good book, podcast, or self development activity that you would recommend? 64:04 Local Network Recommendation? 64:57 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.

Duration:01:07:08

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Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants

12/2/2025
How do I protect myself against potential tenant screening scams? ============= 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 ============= Link: Forewarn.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:12:02

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Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats

11/27/2025
Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical areas of focus and on understanding risks when developing product that will set the top comparable in a neighborhood. Lawrence provides a great take on his top Chicago neighborhoods for upside and reasoning for why he is bullish. Throughout this episode, Lawrence emphasizes the importance of deeply understanding your market and getting in the game to achieve success! 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: Lawrence Dunning, Fulton Grace Realty Link: SUCI Ep 118 - Lawrence Dunning Link: Enter The Lionheart (Lawrence's Podcast) Link: The One Thing (Book Recommendation) Link: Vevor Adjustable Handrails Guest Questions: 03:01 Housing Provider Tip - Leverage adjustable handrails for an affordable solution to meet compliance requirements! 04:58 Intro to our guest, Lawrence Dunning! 12:27 Lawrence's business and areas of focus! 16:40 Real estate agent's value to developers. 26:33 Setting the top comparables in a neighborhood. 35:02 Lawrence's top emerging neighborhoods! 45:46 Outlook on Chicago's south side. 52:01 What is your competitive advantage? 53:00 One piece of advice for new investors. 53:47 What do you do for fun? 54:54 Good book, podcast, or self development activity that you would recommend? 56:43 Local Network Recommendation? 57:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:59:11