Straight Up Chicago Investor

Latest Episodes:

Episode 432: Strategic Chicago House Hacking with Zach Posey Feb 12, 2026

Show notes

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!

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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: 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?

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Production House: Flint Stone Media

Episode 431: What You Need To Know About Real Estate Professional Status with Mike Procaccio Feb 10, 2026

Show notes

What is real estate professional status and why is it important for investors?

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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

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Production House: Flint Stone Media

Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer Feb 05, 2026

Show notes

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

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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?

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Production House: Flint Stone Media

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

Show notes

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

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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

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

Show notes

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

Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon Jan 22, 2026

Show notes

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

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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?

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Production House: Flint Stone Media

Episode 426: Reshaping Suburban Woodstock with Jessica Erickson Jan 15, 2026

Show notes

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

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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?

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Production House: Flint Stone Media

Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options Jan 13, 2026

Show notes

Do you need a HELOC on your investment property?

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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

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Production House: Flint Stone Media

Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith Jan 08, 2026

Show notes

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

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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?

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Production House: Flint Stone Media

Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm Jan 01, 2026

Show notes

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

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Guest: Jonathan Klemm of Quality Builders

Link: Founders (Podcast Recommendation)

Link: SUCI Ep 250 - Jonathan Klemm

Link: SUCI Ep 206 - Prashanth Mahakali