

Straight Up Chicago Investor
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.
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.
Episodes
Mentioned books

Mar 31, 2026 • 14min
Episode 442: How To Identify and Execute on Assumable Loans with Michael Scanlon
What is the process for assuming a VA or FHA loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Scanlon, The Axon Group (EXP Realty) 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.

Mar 26, 2026 • 44min
Episode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations
Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want! Josh jumps right in by explaining the concept of his book and the neuroscience of persuasion! He shares insights on how the brain works as it relates to persuasion and gives tactical negotiation tips. Josh describes the process of writing his book and the impact that artificial intelligence and technology are having on communication. This show is full of golden nuggets to leverage on your next real estate negotiation and to help create more win-win situations in business! 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: Josh Bandoch, Illinois Policy Institute Link: How To Get What You Want (Josh's New Book) Link: Josh's LinkedIn Link: SUCI Ep 347 - Josh Bandoch Link: GC Realty Maintenance Blog Link: Mike Glasser - NBOA Link: How to Stop Worry and Start Living (Book Recommendation) Link: Thinking, Fast and Slow (Book Recommendation) Guest Questions: 02:37 Housing Provider Tip - Have contacts to efficiently solve all maintenance requests! 04:37 Intro to our guest, Josh Bandoch! 06:48 The neuroscience of persuasion. 11:52 Understanding persuasion to get deals done! 16:27 Tactical negotiation tips. 24:10 The process of publishing a book. 36:20 The impact of AI on communication. 38:45 What is your competitive advantage? 39:04 One piece of advice for new investors. 39:34 What do you do for fun? 39:41 Good book, podcast, or self development activity that you would recommend? 41:14 Local Network Recommendation? 41:28 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Mar 19, 2026 • 60min
Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
Jay Patel and Tedi Nati of JP Acquisitions join us to explain how they've leveraged mentors and discipline to build a sizable multifamily portfolio on Chicago's West Side! Jay and Tedi explain how they networked and built their team to set themselves up for success when starting in real estate! They break down raising money and setting up a syndication to acquire their first multifamily building in Austin. The duo discuss their next 16-unit building acquisition and lessons learned on that deal. Jay and Tedi close by sharing their motivative business plan hammering home their go-getter attitude which has led to their great 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 ============= Guests: Jay Patel & Tedi Nati, JP Acquisitions Link: Jay's LinkedIn Link: Tedi's LinkedIn Link: Frank Jaffe (Attorney Referral) Link: Eric Kogan (Network Referral) Guest Questions: 01:08 Intro to our guests, Jay and Tedi! 09:20 Learning how to execute a real estate deal! 16:34 Jay and Tedi''s first syndication deal. 22:45 Software and tools for asset management. 27:07 Mistakes on an 8-unit acquisition. 33:38 The importance of an experienced team. 38:04 Acquiring a 16-unit building in Austin. 44:35 How to make money when starting a syndication? 49:58 2-Year outlook for Jay and Tedi! 56:10 What is your competitive advantage? 56:30 One piece of advice for new investors. 56:40 What do you do for fun? 56:55 Good book, podcast, or self development activity that you would recommend? 57:32 Local Network Recommendation? 58:20 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Mar 17, 2026 • 19min
Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jonathan Klemm, Quality Builders 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.

Mar 12, 2026 • 54min
Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik
Samuel Pavlovcik of the Pavlovcik Architecture returns to explain opportunities brought by the expanded city-wide Additional Dwelling Unit (ADU) Ordinance! Samuel jumps right in by explaining the process and expectations on obtaining a Zoning Change without leveraging the ADU ordinance! He dives deep on various Zoning and Building Code requirements when looking to build and/or legalize a basement ADU. Samuel breaks down various requirements on coach house ADUs and ground-level commercial ADU conversions. He closes with tips for successful ADU projects and shares top pitfalls to avoid when leveraging the program! 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: Samuel Pavlovcik, Pavlovcik Architecture Link: Pavlovcik Architecture's Instagram Link: SUCI Ep 97 - Samuel Pavlovcik Link: SUCI Ep 264 - Samuel Pavlovcik Link: Chicago Zoning Map Link: Tom Moore (Zoning Attorney Referral) Link: The Toyota Way (Book Recommendation) Guest Questions: 03:08 Housing Provider Tip - Optimize your rental listings to attract tenants and avoid vacancy! 05:35 Intro to our guest, Samuel Pavlovcik! 06:10 The 101 on Chicago Zoning changes. 13:34 Building Department considerations for legalizing an ADU. 23:03 Easiest ways to improve building efficiency. 23:25 City wide expansion of Chicago's ADU Ordinance. 32:42 Nuances on coach house ADUs. 38:55 Ground-level Commercial vs Basement ADUs! 44:37 Top mistakes when leveraging the ADU program. 46:31 What is your competitive advantage? 49:16 One piece of advice for new investors. 49:28 What do you do for fun? 49:48 Good book, podcast, or self development activity that you would recommend? 50:00 Local Network Recommendation? 50:57 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Mar 5, 2026 • 1h 18min
Episode 437: Energy Efficiency in Chicago Real Estate with Joe Konopacki
Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and Efficiency! Joe starts with a story on acquiring a mixed-use building to establish his business and invest simultaneously! He breaks down his background of growing up in a real estate family and transitioning into the business. Joe gets granular on causes for building inefficiencies and means for improving building performance. He explains top considerations for heating system options and closes out with some wild inspection stories! 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: Joe Konopacki, Insight Property Services Link: Joe's LinkedIn Link: Modern Wisdom (Podcast Recommendation) Link: The E-Myth Revisited (Book Recommendation) Guest Questions: 02:24 Housing Provider Tip - Understand the benefits of lease agreements over month-to-month agreements! 04:15 Intro to our guest, Joe Konopacki! 10:16 Advantages of mixed-use buildings. 12:02 Growing up in a real estate family and transitioning into the business. 23:03 Easiest ways to improve building efficiency. 31:12 Understanding the efficiency of boilers! 43:05 Considerations for electric heating systems. 52:03 Cost analysis of switching from boilers to central HVAC! 60:27 Incentive opportunities for solar energy systems. 67:13 Wild inspection stories! 71:37 What is your competitive advantage? 73:27 One piece of advice for new investors. 73:38 What do you do for fun? 73:54 Good book, podcast, or self development activity that you would recommend? 74:40 Local Network Recommendation? 75:12 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

Mar 3, 2026 • 11min
Episode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
A rundown of upcoming March, November, and February elections that shape property policy and taxes. A look at which offices matter most to investors, from assessor to mayoral and state races. Discussion of school board influence on property taxes and recent PAC endorsements. Details about a March 11 fundraiser featuring Rahm Emanuel and why investor involvement and fundraising matter.

Feb 26, 2026 • 60min
Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Gil Villegas, alderman of Chicago's 36th Ward and chair of the city's Economic Capital and Technology Committee, talks zoning and affordable housing policy. He discusses using zoning changes to create community wins, cutting red tape with tech and RFIs, organizing council action on the budget, and why he withdrew from the Northwest Housing Ordinance. He ends with a bullish vision for Chicago's future.

Feb 24, 2026 • 14min
Episode 434: Interesting Lease Renewal Statistics and Strategies with Mark Ainley
What are the common mistakes made when handling lease renewals? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty 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.

Feb 19, 2026 • 55min
Episode 433: Chicago Building Code Violations with Zack Limbaugh
Zack Limbaugh, an attorney who handles Chicago building code and municipal enforcement, returns with practical intel. He covers buying properties with violations, lender challenges, due diligence tactics like maps and FOIA, common tickets to watch for, demo court risks, and how to manage fines and compliance timelines.


