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Straight Up Chicago Investor

Straight Up Chicago Investor

By: Straight Up Chicago Investor
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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.Copyright of Straight Up Chicago Investor 2021. Career Success Economics Personal Finance
Episodes
  • Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati

    Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
    Mar 19 2026

    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!

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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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    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.
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    1 hr
  • Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm

    Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
    Mar 17 2026

    What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan?

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    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.
    Show more Show less
    19 mins
  • Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik

    Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik
    Mar 12 2026
    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.
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    54 mins
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