Straight Up Chicago Investor

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**Straight Up Chicago Investor**

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.

Latest Episodes:

Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market Dec 30, 2025

Show notes

Is now a good time for me to purchase in Chicago?

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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

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Production House: Flint Stone Media

Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1 Dec 25, 2025

Show notes

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!

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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: 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?

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Production House: Flint Stone Media

Episode 420: The Chicago Permitting Process with Tom Shallcross Dec 18, 2025

Show notes

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!

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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

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

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?

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Production House: Flint Stone Media

Episode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley Dec 16, 2025

Show notes

How do I navigate the rent determination process for Section 8 applicants in Chicagoland?

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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

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Production House: Flint Stone Media

Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords Dec 11, 2025

Show notes

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?

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Production House: Flint Stone Media

Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal Dec 04, 2025

Show notes

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?

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Production House: Flint Stone Media

Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants Dec 02, 2025

Show notes

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

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Production House: Flint Stone Media

Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats Nov 27, 2025

Show notes

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?

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Production House: Flint Stone Media

Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows Nov 20, 2025

Show notes

SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs!

Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs!

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: Mark Ainley of GC Realty & Development

Link: Mark's Instagram

Link: The Science of Scaling (Book Recommendation)

Link: It's How We Play The Game (Book Recommendation)

Guest Questions:

03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up!

03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements!

04:55 Intro to our guest, Mark Ainley!

05:48 The history of village requirements for rentals.

09:17 Considerations when investing in Schaumburg.

17:27 Insights on permits and associated fees.

21:38 Navigating point of sale inspections in different villages.

31:46 What to know about tax transfer stamps!

35:56 Overview on rental licenses, village inspections, STR licenses, and more!

39:51 Book recommendations from Mark!

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Production House: Flint Stone Media

Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev Nov 18, 2025

Show notes

When do I have to have my cost segregation done to ensure it is good for my 2025 taxes?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Cost Seg Kev from CSSI

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: Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars

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Production House: Flint Stone Media

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