Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate 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: [email protected]

Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360

Link: Joe Smazal's LinkedIn

Link: Ann Reilly's LinkedIn

Link: SUCI Ep 156 - Joe Smazal

Link: Northwest Side Building Coalition (NSBC) Website

Guest Questions

00:30 The State of Chicago’s NW Side Commercial Real Estate.

04:33 Leasing trends and strategies!

10:18 Dealing with evictions in today’s market.

17:17 Who is transacting in multifamily real estate in Chicago?

20:58 The evolution of the tenant pool and the market in Chicago.

24:53 Rapid fire Chicago real estate questions!

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

How do I incentivize and optimize renewals?

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

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: [email protected]

Guest: Jeff Weinberg, Drexel Properties

Link: Jeff Weinberg Shares Property Management Expertise on the Straight Up Chicago Investor Podcast

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals!

Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creative” deals including one deal where he was able to close on a property minutes before it would have been foreclosed on. Jeffrey explains how he’s gotten into bigger deals including a multifamily syndication and brokering a warehouse space that resulted in a six-figure commission! Throughout the show, Jeffrey is able to eloquently convey his approach to real estate and life which revolves around enjoying the process and being grateful for the present moment!

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: [email protected]

Guest: Jeffrey Ma, Keller Williams Preferred Realty

Link: Jeffrey's Instagram

Link: Chicago Real Estate Investors Meetup

Link: Eli Goodman's LinkedIn

Link: SUCI Ep 326 - RJ de Leon (Network Referral)

Link: Mind Management, Not Time Management (Book Recommendation)

Guest Questions

02:53 Housing Provider Tip - Keep a bag of ice melt at your properties in the event of unforeseen slippery conditions!

04:27 Intro to our guest, Jeffrey Ma!

12:10 Gaining momentum in real estate and getting into wholesaling!

19:11 Jeffrey’s journey to creative deals.

25:18 Case studies of “cool” deals!

29:44 Jeffrey’s most “unconventional” deal to date.

36:46 Getting into bigger deals including a 6-figure commission!

40:06 The Origin Story of Jeffrey’s and his partner Eli’s meetup.

43:02 What’s next for Jeffrey?!

48:35 What is your competitive advantage?

49:00 One piece of advice for new investors.

49:23 What do you do for fun?

49:58 Good book, podcast, or self development activity that you would recommend? 

51:21 Local Network Recommendation? 

51:42 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio!

Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that involved getting caught doing construction without a permit and going significantly over budget! Wyatt explains the issues that arise from lack of liquidity even for high networth individuals. Throughout the episode, Wyatt drops powerful insights on mentorship, staying disciplined, and starting with the end in mind!

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: [email protected]

Guest: Wyatt Simon, Full Circle Real Estate

Link: Wyatt's Instagram

Link: Wyatt's 7 Figure Mastermind

Link: Your First 100 Units (Wyatt's Book)

Link: 7 Habits of Highly Effective People (Book Recommendation)

Link: Jake and Geno (Network Referral)

Guest Questions

03:30 Housing Provider Tip - Understand appliance warranties and reconsider extending warranties!

05:09 Intro to our guest, Wyatt Simon!

11:16 Wyatt’s first BRRRR deal.

14:50 A third deal, gone bad!

19:47 How to start direct-to-seller marketing.

28:02 Ins and outs of “subject to” financing deals.

34:07 Navigating liquidity concerns.

37:56 Wyatt’s 5-year outlook!

41:12 What is your competitive advantage?

41:37 One piece of advice for new investors.

42:53 What do you do for fun?

43:10 Good book, podcast, or self development activity that you would recommend? 

44:16 Local Network Recommendation? 

44:52 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

How does credit effect DSCR loans?

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

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: [email protected]

Guest: Eric Workman, Renovo Financial

Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans

Link: Build Your Team | Straight Up Chicago Investor Podcast

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John dives into starting a property management company along with building and remaining loyal to a team to support his portfolio. Mr. Warren closes with motivating words on entrepreneurship and why you should take the leap of faith!

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: [email protected]

Guest: John Warren, Forte Properties

Link: Forte Properties (@fortepropertieschicago) • Instagram photos and videos

Link: Extreme Ownership (Book Recommendation)

Link: Luke Erlandson (Agency Lender Referral)

Guest Questions

02:53 Intro to our guest, John Warren!

03:18 Lessons learned from growing a 168-unit portfolio!

06:50 How to simply structure a partnership?

12:00 John’s geographical focus and plans for growth.

21:01 Resetting expectations on real estate investment returns!

23:45 Setting up a property management office.

26:27 Property management software and leveraging virtual assistants.

31:48 John’s recent horror story!

33:53 What would John do differently in his journey?

34:47 Growing a family while pursuing entrepreneurship.

36:50 What is your competitive advantage?

37:18 One piece of advice for new investors.

37:43 What do you do for fun?

38:26 Good book, podcast, or self development activity that you would recommend? 

39:00 Local Network Recommendation? 

40:15 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations.

Scott starts by sharing his experience working at JPMorgan’s Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a case study of an adaptive reuse project and gets granular on how the acquisition opportunity was presented, how the capital was raised, and construction considerations. Scott shares notable due diligence stories and talks about what to look for in buildings when considering adaptive reuse redevelopment. This is a great show that sheds light on the opportunities and incentives available for affordable housing developers! 

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: [email protected]

Guest: Scott Henry, Celadon Partners

Link: Scott's LinkedIn

Link: Banana Ball (Book Recommendation)

Link: Landmarks Illinois (Network Referral)

Link: SUCI Ep 351 - Richard Koenig Guest Questions

02:47 Housing Provider Tip - Dial in your tenant screening process to prevent issues!

04:22 Intro to our guest, Scott Henry!

08:50 The Low Income Housing Tax Credit.

13:25 Case Study - Adaptive Reuse Project!

20:45 Covenants for Tax Credits and Grants.

28:54 Construction Considerations on Adaptive Reuse Projects.

34:03 Shocking stories during due diligence.

37:40 What is your competitive advantage?

38:14 One piece of advice for new investors.

38:34 What do you do for fun?

39:05 Good book, podcast, or self development activity that you would recommend? 

40:39 Local Network Recommendation? 

41:46 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

What actionable steps do I need to take for the Northwest Side Preservation Ordinance?

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

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: [email protected]

Guest: Brie Schmidt, Second City Real Estate 

Link: Northwest Side Preservation Ordinance Link: The Current State Of Chicago’s Northside Real Estate Market With Managing Broker Brie Schmidt Link: Episode 327: Logan & Humboldt Property Owners’ Rights Taken By The New NW Preservation Ordinance with Luke Blahnik

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo provides real life examples of how a land trust can help protect housing providers from lawsuits and help maintain privacy. This show is loaded with valuable tips on asset protection and privacy to help you bulletproof your portfolio! 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: [email protected]

Guest: David Lanciotti and Del Denney, The Land Trust Company

Link: High Performance Playbook (Del's Book!)

Link: Deep Work (Book Recommendation)

Link: Bunkhouse Logic (Book Recommendation) Guest Questions

01:51 Housing Provider Tip - Vet tenant’s income before agreeing to a payment plan. 05:31 Intro to our guests, Del and David! 07:30 The Ins and Outs of Land Trusts. 16:41 The downsides of a Land Trust. 22:03 Deep Dive on Trusts and Probate! 29:55 When does it not make sense to set up a Trust? 33:38 The process and costs for setting up a trust. 38:55 What is your competitive advantage? 39:27 One piece of advice for new investors. 39:55 What do you do for fun? 40:30 Good book, podcast, or self development activity that you would recommend?  42:33 Local Network Recommendation?  43:01 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions!

Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction case. Tom hits us with rapid fire eviction stats including neighborhoods and even streets where his office has had the most eviction filings. He closes with top insights on complying with Fair Housing and tenant screening to avoid eviction court altogether!

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

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

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: [email protected]

Guest: Tom Raleigh, Halsted Law Group

Link: Tom Raleigh's LinkedIn

Link: Meditations (Book Recommendation)

Link: Shawn Ryan Show (Podcast Recommendation) Guest Questions

02:27 Housing Provider Tip - Dial in your tenant screening process to prevent issues!

04:17 Intro to our guest, Tom Raleigh!

5:01 The Eviction Process in 2025.

12:48 How can landlords get ahead in the eviction process?

21:56 Rapid fire stats on Tom’s eviction filings!

30:40 Housing Section of the CARES Act.

39.28 10 Day Notice for Cause.

47:36 Tips for Landlords to avoid Fair Housing violations.

55:41 What is your competitive advantage?

56:15 One piece of advice for new investors.

56:32 What do you do for fun?

56:58 Good book, podcast, or self development activity that you would recommend? 

57:38 Local Network Recommendation? 

58:38 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.