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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 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn
    May 21 2026

    Duke Dennis and Bryan Sonn of GC Realty & Development join us to explain the ins and outs of Chicagoland Industrial Investments!

    Duke and Bryan explain how they got their start in industrial real estate. They dive deep on the differences between residential and industrial property investing. They discuss how they went from a property manager to an owner operator and share ways to add value to industrial properties. Duke and Bryan get granular on a deal in Mundelein including details on the capital raising, acquisition, stabilization, and hurdles that come up during the process. Through the show, Duke and Bryan provide insights to industrial property investing and convey the major ROI opportunities in this often overlooked asset class!

    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: Duke Dennis & Bryan Sonn, GC Realty & Development

    Link: Email Bryan: Bryan@GCrealty.inc | Bryan's LinkedIn

    Link: Email Duke: Duke.Dennis@GCrealty.inc | Duke's LoopNet Page

    Guest Questions:

    00:52 Housing Provider Tip - Understand best tenant applications in a competitive market!

    02:33 Intro to our guests, Bryan Sonn and Duke Dennis!

    06:48 Managing industrial properties compared to residential.

    10:38 From property manager to owner operator.

    20:03 Value-add components on industrial properties.

    30:50 Breaking down a Mundelein industrial deal.

    37:46 Dealing with and overcoming unexpected challenges.

    41:28 Avoiding liquidity issues on large scale projects.

    53:07 Benefits of being a passive investor in a reputable syndication fund.

    55:53 Opportunities in smaller scale industrial deals.

    63:36 5 Year Outlook on Chicagoland Industrial Property Market!

    67:40 What is your competitive advantage?

    68:50 One piece of advice for new investors.

    71:10 What do you do for fun?

    71:36 Good book, podcast, or self development activity that you would recommend?

    72:07 Local Network Recommendation?

    72:17 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 and 15 mins
  • Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust
    May 14 2026

    Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states!

    Igor breaks down his first few deals which includes an $800 land deal in Colorado and a distressed single family home in Indiana! He shares countless stories on auction properties, cold calling, and learning the process of wholesaling to create deal flow. Igor explains mistakes made on buying deals with quit claim deeds and due diligence. He gets granular on how he gained lead generation momentum through PPC, SEO, and various other real estate marketing strategies which propelled his business. Through the show, Igor shares entertaining stories that exemplify how taking massive action is the key to success in REI!

    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: Igor Mike Kajpust, Evolved Property Group

    Link: Igor's Instagram

    Link: SUCI Ep 166 - J Scott

    Link: ilFLS Website

    Guest Questions:

    01:35 Housing Provider Tip - Account for expenses related to lead plumbing lines when purchasing older buildings.

    02:57 Intro to our guest, Igor Mike Kajpust!

    04:52 Getting scrappy to find the first few deals.

    19:00 Learning the process of wholesaling.

    26:48 Transitioning to flipping properties.

    35:01 Improving business processes and efficiency.

    37:03 Building a rental portfolio in Chicago.

    40:21 Distressed property horror stories!

    47:45 Jumping into private lending in Chicago.

    51:37 How to navigate the auction process.

    57:57 What is your competitive advantage?

    58:25 One piece of advice for new investors.

    59:24 What do you do for fun?

    59:57 Good book, podcast, or self development activity that you would recommend?

    60:35 Local Network Recommendation?

    61:00 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.

    Show More Show Less
    1 hr and 4 mins
  • Episode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure
    May 12 2026

    What do real estate investors need to know about the Big Beautiful Bill?

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Aaron Zimmerman, Brick House CPAs

    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

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.

    Show More Show Less
    16 mins
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