Episode 402: Looking At Chicago Investing Differently with Jason Wagner
Release Date: 09/25/2025
Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer
Straight Up Chicago Investor
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...
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Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
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...
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Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley
Straight Up Chicago Investor
What are recent legal updates to the 2026 lease and new squatter laws? ============= Connect with Mark and Tom: Guest: Mark Ainley, and Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2026.
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Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
Straight Up Chicago Investor
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...
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Episode 426: Reshaping Suburban Woodstock with Jessica Erickson
Straight Up Chicago Investor
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...
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Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options
Straight Up Chicago Investor
Do you need a HELOC on your investment property? ============= Connect with Mark and Tom: Guest: Benjamin Stef, Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2026.
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Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith
Straight Up Chicago Investor
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...
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Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm
Straight Up Chicago Investor
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...
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Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market
Straight Up Chicago Investor
Is now a good time for me to purchase in Chicago? ============= Connect with Mark and Tom: Guest: Mark Ainley, Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1
Straight Up Chicago Investor
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...
info_outlineJason shares why he chose to invest in Chicago’s northwest side and how he’s achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset’s ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors!
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: Jason Wagner, Greystone Realty
Link: SUCI Ep 224 - Jason Wagner
Link: Real Life Investing with Jason & Rachel Wagner (Podcast)
Link: Wagner Report
Link: The 5 Types of Wealth (Book Recommendation)
Link: SUCI Ep 244 - Ryan Bakke
Guest Questions
02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers!
04:52 Intro to our guest, Jason Wagner!
10:53 Emerging neighborhoods and creative strategies for cash flow!
28:42 Ins and outs of assumable loans.
36:06 Insights on VA loan assumptions.
38:03 The background on Greystone Realty.
42:56 Housing market takeaways from the Wagner Report!
45:58 Opportunities in Arlington Heights.
50:26 Best of advice for aspiring real estate investors.
52:42 What is your competitive advantage?
53:07 One piece of advice for new investors.
53:20 What do you do for fun?
54:28 Good book, podcast, or self development activity that you would recommend?
56:19 Local Network Recommendation?
57:11 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 2025.