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!

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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: 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.

Duke Dennis and Bryan Sonn of GC Realty & Development join us to explain the ins and outs of Chicagoland Industrial Investments!

Duke and Bryan explain how they got their start in industrial real estate. They dive deep on the differences between residential and industrial property investing. They discuss how they went from a property manager to an owner operator and share ways to add value to industrial properties. Duke and Bryan get granular on a deal in Mundelein including details on the capital raising, acquisition, stabilization, and hurdles that come up during the process. Through the show, Duke and Bryan provide insights to industrial property investing and convey the major ROI opportunities in this often overlooked asset class!

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

=============

Guests: Duke Dennis & Bryan Sonn, GC Realty & Development

Link: Email Bryan: Bryan@GCrealty.inc | Bryan's LinkedIn

Link: Email Duke: Duke.Dennis@GCrealty.inc | Duke's LoopNet Page

Guest Questions:

00:52 Housing Provider Tip - Understand best tenant applications in a competitive market!

02:33 Intro to our guests, Bryan Sonn and Duke Dennis!

06:48 Managing industrial properties compared to residential.

10:38 From property manager to owner operator.

20:03 Value-add components on industrial properties.

30:50 Breaking down a Mundelein industrial deal.

37:46 Dealing with and overcoming unexpected challenges.

41:28 Avoiding liquidity issues on large scale projects.

53:07 Benefits of being a passive investor in a reputable syndication fund.

55:53 Opportunities in smaller scale industrial deals.

63:36 5 Year Outlook on Chicagoland Industrial Property Market!

67:40 What is your competitive advantage?

68:50 One piece of advice for new investors.

71:10 What do you do for fun?

71:36 Good book, podcast, or self development activity that you would recommend?

72:07 Local Network Recommendation?

72:17 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.

Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states!

Igor breaks down his first few deals which includes an $800 land deal in Colorado and a distressed single family home in Indiana! He shares countless stories on auction properties, cold calling, and learning the process of wholesaling to create deal flow. Igor explains mistakes made on buying deals with quit claim deeds and due diligence. He gets granular on how he gained lead generation momentum through PPC, SEO, and various other real estate marketing strategies which propelled his business. Through the show, Igor shares entertaining stories that exemplify how taking massive action is the key to success in REI!

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: Igor Mike Kajpust, Evolved Property Group

Link: Igor's Instagram

Link: SUCI Ep 166 - J Scott

Link: ilFLS Website

Guest Questions:

01:35 Housing Provider Tip - Account for expenses related to lead plumbing lines when purchasing older buildings.

02:57 Intro to our guest, Igor Mike Kajpust!

04:52 Getting scrappy to find the first few deals.

19:00 Learning the process of wholesaling.

26:48 Transitioning to flipping properties.

35:01 Improving business processes and efficiency.

37:03 Building a rental portfolio in Chicago.

40:21 Distressed property horror stories!

47:45 Jumping into private lending in Chicago.

51:37 How to navigate the auction process.

57:57 What is your competitive advantage?

58:25 One piece of advice for new investors.

59:24 What do you do for fun?

59:57 Good book, podcast, or self development activity that you would recommend?

60:35 Local Network Recommendation?

61:00 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 real estate investors need to know about the Big Beautiful Bill?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Aaron Zimmerman, Brick House CPAs

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.

Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago!

Alderman Lawson jumps right in by explaining the successful development in Wrigleyville including partnering with the Ricketts family! He breaks down successful developments including Advocate Masonic Hospital in Lakeview and across the 44th Ward. Alderman Lawson gives practical advice for developers to help increase the chance of having aldermanic support on potential projects! He dives deep on the ADU Pilot Program, its city wide expansion, and how it can best be leveraged to bring much needed housing supply to the city. This show is full of golden insights on Zoning and Development that you won't want to miss!

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: Alderman Bennett Lawson, City of Chicago 44th Ward

Link: Alderman Lawson's Instagram

Link: Chicago ADU Program

Link: Chicago's Great Fire (Book Recommendation)

Link: Tom Moore (Zoning Attorney)

Guest Questions:

01:55 Housing Provider Tip - Leverage rent payment services to allow tenants to build their credit history!

03:38 Intro to our guest, Alderman Lawson!

10:55 The development history of Wrigleyville!

18:20 Previous developments in the 44th Ward.

23:30 Advice for developers seeking support from aldermen.

27:18 The background of the Chicago ADU Program!

31:41 Lessons learned from the ADU Pilot Program.

44:08 Potential solutions for the housing supply issue.

48:50 What is your competitive advantage?

49:11 One piece of advice for new investors.

49:35 What do you do for fun?

49:48 Good book, podcast, or self development activity that you would recommend?

50:48 Local Network Recommendation?

51:15 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.

Mike Scanlon of the Axon Group returns to share his personal real estate journey with several insights on how he has reached his success!

Mike starts by discussing his background prior to real estate and then jumps into his first property acquisition which was a rent-by-the-room condo house hack! He shares how he got gritty and creative to finance and acquire a pair of distressed properties in University Park. Mike breaks down how he identified value and got a down payment to purchase a prime 3-unit house hack in Lakeview! He explains how he grinded to build his real estate brokerage business and used commissions to fund his portfolio. Mike closes the show with how his investment strategy has shifted and with Chicago neighborhoods that he's extra 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: Mike Scanlon, The Axon Group

Link: Mike's Instagram

Link: The Axon Group Instagram

Link: SUCI Ep 427 - 2026 Predictions with the Axon Group

Link: SUCI Ep 398 - Paul de Luca

Link: Never Split the Difference (Book Recommendation)

Guest Questions:

01:50 Housing Provider Tip - Consider offering tenants a valuable unit improvement when enforcing large rent increases.

03:23 Intro to our guest, Mike Scanlon!

10:17 Mike's start in real estate.

17:25 How Mike acquired his second deal.

23:45 Buying a prime 3-unit in Lakeview!

32:49 Building a pipeline of leads as a real estate broker.

37:16 A creative 8-unit deal in Melrose Park!

43:27 Mike's shift in investment strategy.

49:01 Up and coming Chicago neighborhoods!

50:25 What is your competitive advantage?

52:15 One piece of advice for new investors.

54:01 What do you do for fun?

55:23 Good book, podcast, or self development activity that you would recommend?

56:38 Local Network Recommendation?

57:33 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.