Straight Up Chicago Investor

Straight Up Chicago Investor
  • 5.0 (291)
  • INVESTING
  • UPDATED WEEKLY

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.

  1. Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik

    2D AGO

    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.

    54 min
  2. Energy Efficiency in Chicago Real Estate with Joe Konopacki

    MAR 5

    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.

    1h 18m
  3. Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel

    MAR 3

    Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel

    What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser & Aron Borstein, NBOA PAC | An Evening with Rahm Emanuel ⭐⭐Get your tickets today!⭐⭐ 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.

    11 min
  4. 36th Ward: Future of Chicago with Alderman Gil Villegas

    FEB 26

    36th Ward: Future of Chicago with Alderman Gil Villegas

    Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward! Alderman Villegas starts by discussing how zoning changes can be utilized to create win-win situations for investors and members of a community or ward! He talks about how he and his fellow members of City Counsel were able to influence the city's approved budget with the needs of their constituents at the forefront. Alderman Villegas breaks down why he chose to withdraw his Ward from the Northwest Housing Ordinance. He closes with an extremely bullish outlook on Chicago leaving us motivated to continue doubling down on our great city! 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: Alderman Gil Villegas, City of Chicago's 36th Ward Link: Alderman Villegas' Facebook Link: Alderman Villegas' Instagram Link: The 48 Laws of Power (Book Recommendation) Link: NBOA Chicago (Network Recommendation) Guest Questions:  03:31 Housing Provider Tip - Understand lease renewal notices to remain compliant! 05:28 Intro to our guest, Alderman Villegas! 07:19 Zoning changes to create affordable housing. 18:48 City council's involvement with the city's approved budget. 25:45 How Aldermen work together to make positive impacts! 35:05 Drawbacks of the Northwest Housing Ordinance. 43:34 How Aldermen utilize facts and community input to make decisions. 45:39 Exciting developments in the 36th ward! 48:28 Alderman Villegas' outlook on Chicago. 51:41 What is your competitive advantage? 52:11 One piece of advice for new investors. 54:26 What do you do for fun? 55:46 Good book, podcast, or self development activity that you would recommend?  56:08 Local Network Recommendation?  56:31 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.

    1 hr
  5. Interesting Lease Renewal Statistics and Strategies with Mark Ainley

    FEB 24

    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.

    14 min
  6. Chicago Building Code Violations with Zack Limbaugh

    FEB 19

    Chicago Building Code Violations with Zack Limbaugh

    Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Throughout the show, Zack provides insights on handling various code violation scenarios to give you an edge against the competition! 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: Zack Limbaugh, The Limbaugh Law Firm Link: Zack's LinkedIn Link: SUCI Ep 333 - Zack Limbaugh Link: SUCI Ep 79 - Gary Davidson Link: Essentialism (Book Recommendation) Guest Questions:  02:35 Housing Provider Tip - Understand the true costs of not allowing pets in your rentals! 04:44 Intro to our guest, Zach Limbaugh! 10:23 Buying a property with code violations. 16:48 Lending considerations for violations exist. 23:52 Protecting yourself against fines for code violations! 31:03 Ensuring violations are found during due diligence. 43:15 Common violation tickets to watch out for! 50:35 Crazy code violation stories! 51:17 What is your competitive advantage? 51:32 One piece of advice for new investors. 51:39 What do you do for fun? 51:51 Good book, podcast, or self development activity that you would recommend?  52:03 Local Network Recommendation?  52:18 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.

    55 min
  7. Strategic Chicago House Hacking with Zach Posey

    FEB 12

    Strategic Chicago House Hacking with Zach Posey

    Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required! 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: Zach Posey, Chicago Multifamily Club Link: Chicago Multifamily Club Meetup Link: Wisdom Takes Work (Book Recommendation) Link: SUCI Ep 52 - Aaron Zimmerman Link: SUCI Ep 326 - RJ de Leon Guest Questions:  01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals! 03:57 Intro to our guest, Zach Posey! 07:38 Starting off with a 4-unit house hack. 17:25 Acquiring a second house hack in Roscoe Village. 26:28 Property Management tips for house hackers! 28:44 Leveraging assumable loans to make the numbers pencil. 34:41 The value of networking events. 37:40 Zach's REI goals and outlook on Chicago! 42:42 What is your competitive advantage? 43:13 One piece of advice for new investors. 43:35 What do you do for fun? 43:50 Good book, podcast, or self development activity that you would recommend?  44:40 Local Network Recommendation?  45:39 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.

    50 min
  8. What You Need To Know About Real Estate Professional Status with Mike Procaccio

    FEB 10

    What You Need To Know About Real Estate Professional Status with Mike Procaccio

    What is real estate professional status and why is it important for investors? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Michael Procaccio, Pro Financial Services Group Inc 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.

    18 min
See All (440)

Trailer

5
out of 5
291 Ratings

About

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.

Information

  • Creator
    Straight Up Chicago Investor
  • Years Active
    2020 - 2026
  • Episodes
    440
  • Rating
    Clean
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

You Might Also Like