Matt Katsaros of Wildwood Investments returns to break down ground-up development projects that he's taking down in Chicago!

Matt jumps right in by explaining how his experience in commercial real estate brokerage and acquisitions led him to starting and scaling his development business. He dives deep into a Lincoln Park development deal and shares insights on raising capital, finding deals, and construction to successfully complete a development deal! Matt dives into the nuances of adaptive reuse projects and the process of securing tax increment financing (TIF) funds. Matt closes with tremendous tips on apartment layouts and characteristics that help maximize rents!

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: Matt Katsaros of Wildwood Investments

Link: Matt's LinkedIn

Link: SUCI Ep 109 (Matt's First Appearance on SUCI)

Link: Real Estate For Breakfast Podcast

Link: Spittin Chiclets Podcast

Guest Questions:

02:00 Housing Provider Tip - Document apartment conditions prior to tenant move-ins.

04:25 Intro to our guest, Matt Katsaros!

10:37 Dissecting Matt's Lincoln Park development deal!

18:32 Tips for raising capital.

28:28 Breaking down an office-to-residential adaptive reuse deal.

37:58 The process to secure TIF funds.

44:18 Earning steady income between the disposition of developments.

46:13 Matt's outlook on his business and on Chicago.

50:27 Apartment characteristics that maximize rents!

62:33 What is your competitive advantage?

62:47 One piece of advice for new investors.

63:05 What do you do for fun?

63:35 Good book, podcast, or self development activity that you would recommend?

64:03 Local Network Recommendation?

64:26 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.

Mark and Tom discuss the current fundamentals of the Chicago market with statistics provided by Jason Wagner.

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Tom & Mark, Straight Up Chicago Investor Podcast

Link: Jason Wagner's Market Reports

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

Copyright of Straight Up Chicago Investor 2026.

John Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago's North Side!

John begins by discussing what it takes to build a successful brokerage business including early struggles before hitting his stride! He breaks down his process for reaching out to and converting seller leads and also explains the work brokers do that leads to a successful transaction. In typical SUCI fashion, John gets hyper-specific on neighborhoods that have seen great rent growth and areas where he sees investors putting their money! He closes with a bullish outlook on Chicago and emphasizes the importance of building market knowledge and networking to be successful in the game!

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: John Preston, Horvath & Tremblay | Email John: jpreston@hgapartments.com | Connect with John on LinkedIn

Link: NBOA Chicago

Guest Questions:

02:45 Housing Provider Tip - Understand catch basins and have a maintenance plan.

04:35 Intro to our guest, John Preston!

06:47 Getting off the ground as a real estate broker focusing on multi-family assets.

16:17 Troubling deals early on in John's career.

22:18 The work behind a successful listing.

29:30 Effectively following up with and converting leads!

31:27 How buyers can find opportunities in today's market.

34:57 John breaks down north side neighborhoods!

45:00 John's pick for a neighborhood with major upside!

50:17 John's bullish outlook on Chicago.

51:15 What is your competitive advantage?

52:15 One piece of advice for new investors.

53:04 What do you do for fun?

53:34 Good book, podcast, or self development activity that you would recommend?

54:23 Local Network Recommendation?

55:11 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 2026.

What steps should I take to best prepare for my 2026 tax returns?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Aaron Zimmerman, Brick House CPAs

Link: SUCI Episode 52

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

Copyright of Straight Up Chicago Investor 2026.

Jason Wagner, Managing Broker of Greystone Realty, returns to discuss the state of the Chicago Real Estate market and the power of buy and hold investments.

Jason starts by discussing buyer expectations and demand in today's market. He dives into the data behind Chicago property value appreciation and rent growth across different neighborhoods! Jason shares client success stories involving house hacks, using leverage responsibly, and adding value to create meaningful equity gains. He closes with top advice for new investors and an extremely bullish outlook on select neighborhoods and Chicago as a whole!

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: Jason Wagner, Greystone Realty

Link: Jason's Instagram

Link: SUCI Ep 402 - Jason Wagner

Link: Wagner Report

Link: Wonderful Togbey (Network Referral)

Link: The 10X Rule (Book Recommendation)

Guest Questions:

01:07 Housing Provider Tip - Understand and adhere to flood disclosure requirements on leases.

03:03 Intro to our guest, Jason Wagner!

09:31 Buyer demand in today's market.

15:28 Property appreciation and lack of inventory.

22:10 Chicago neighborhoods that Jason is bullish on!

33:42 The power of rent growth and appreciation.

36:43 The latest on the Wagner Report.

47:26 Top lessons learned as a young investor!

50:35 Top Chicagoland neighborhoods and areas with upside!

53:42 Jason's bullish outlook on Chicago real estate.

55:09 What is your competitive advantage?

55:34 One piece of advice for new investors.

56:05 What do you do for fun?

58:38 Good book, podcast, or self development activity that you would recommend?

59:00 Local Network Recommendation?

60:38 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.

What do I need to be aware of when assigning a contract?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Chance Badertscher, Chance The Lawyer

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

Copyright of Straight Up Chicago Investor 2026.