Straight Up Chicago Investor

Mark (Straight Up Chicago Investor), Tom (Straight Up Chicago Investor)
mark@gcrealtyinc.com (+1 verified host & producer email)

Booking Overview

A Chicago-focused real estate investing and property management show that brings on local experts to share practical strategies, deal sourcing, and regulatory/zoning considerations. It’s a strong platform for guests who can teach “ground level” lessons from building, funding, acquiring, or developing in the Chicagoland market.

Metrics

Episodes: 457

Frequency: Irregular

Rating: 5.0/5.0

Estimated listeners: 1k-10k

Gender skew: Male

Location: USA

YouTube: 2.7k subscribers

Instagram: 1.6k followers

30s Ad: 172 - 208, 60s Ad: 202 - 238

Contact Form

Contact form available - Official Form

Host

Mark (Straight Up Chicago Investor) - Co-host of Straight Up Chicago Investor, focused on sharing actionable, local insights for Chicago real estate investors and property managers, including strategies, obstacles, success stories, and...

Tom (Straight Up Chicago Investor) - Co-host of Straight Up Chicago Investor, partnering with Mark to highlight practical, investor-grade knowledge about acquiring, improving, and operating real estate in Chicagoland—often leveraging ...

Booking Intelligence

Booking Requirements

medium
Typical Credentials:  
Chicago/Chicagoland operators and practitioners: active real estate investors, property managers, and local deal leaders; plus adjacent professionals such as CPAs and zoning/development stakeholders who can translate policy/finance into actionable guidance for investors.
Required Achievements:  
Demonstrated track record of Chicago-area acquisitions or portfolio growth, Hands-on experience with deal sourcing (including off-market/auctions) and operations (property management and/or tenant placement), Professional expertise serving investors (e.g., CPA/tax planning) with real-world applicability, Involvement in local development initiatives or public-policy programs (e.g., aldermanic role tied to housing supply efforts)

Recent Guest Discussions

Igor Mike Kajpust - Off-market Deal Sourcing; Wholesaling; Flipping; Lead Generation (ppc/seo); Due Diligence Mistakes; Auction Properties; Private Lending; Chicago Rental Portfolio Growth

Aaron Zimmerman - Tax Minimization Considerations For Real Estate Investors Related To The “big Beautiful Bill”

Bennett Lawson - Local Development History; Leveraging Aldermanic Support; Chicago ADU Program; Zoning/development Insights To Increase Housing Supply

Recent Topics

Real Estate, Investing, Property Management, Chicago, Tax, Zoning, Personal Development, Private Lending, Lead Generation

Episodes

Here's the recent few episodes on
Straight Up Chicago Investor
:

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 ca...

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 gr...

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? ============= 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...

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