
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 Wi... more
| Publishes | Twice weekly | Episodes | 459 | Founded | 6 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | InvestingCareersBusiness | |||

Jason Wagner, Managing Broker of Greystone Realty, returns to discuss the state of the Chicago Real Estate market and the power of buy and hold investments.
Jason starts by discussing buyer expectations and demand in today's market. He dives into t... more
What do I need to be aware of when assigning a contract?
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Connect with Mark and Tom: StraightUpChicagoInvestor.com
Guest: Chance Badertscher, Chance The Lawyer
Email the Show: StraightUpChicagoInvestor@gmail.com
Link: Build Yo... more
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 re... more
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 sin... more
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Mark has so much information and experience in the Chicago market. This show is a must-follow!
Best podcast about insights on the Chicagoland real estate market and amazing hosts!
Also full of good insights!
Been listening while getting smarter in Chicago neighborhoods and investment dynamics. Really appreciate the practical, on-the-ground perspective you guys bring to each episode.
(cue Da Rude - Sandstorm)
STRAIGHT. UP. CHICAGO.
THIS IS HOW YOU WIN
I met Mark not too long ago and the man is full of understanding and wisdom in the industry. This podcast really gives us even more understanding and I am grateful for the value Mark and Tom provide. Thank you!
Key themes from listener reviews, highlighting what works and what could be improved about the show.










Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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A focused, ground-level look at Chicago real estate investing, property management, and local policy. Episodes consistently center on neighborhood dynamics, local market conditions, financing tools, and regulatory changes that shape buying, leasing, and development in the Chicago area. Guests range from seasoned investors and brokers to developers and city officials, offering practical tactics, data-driven insights, and behind-the-scenes perspectives on navigating zoning, permits, and incentives. A standout trait is the emphasis on local dynamics and actionable takeaways over generic market commentary, making it especially valuable for investors and operators active in Chicagoland.
Noteworthy is the recurring focus on city-specific policy,... more
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These podcasts share a similar audience with Straight Up Chicago Investor:
1. Real Estate Chicago Style Podcast
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3. Lifetime Cash Flow Through Real Estate Investing
4. Real Estate Rookie
5. The Best Ever CRE Show
Straight Up Chicago Investor launched 6 years ago and published 459 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Straight Up Chicago Investor include:
1. Igor Kajpust
2. Aaron Zimmerman
3. Alderman Bennett Lawson
4. Michael Scanlon
5. Chance The Lawyer (Chance Badertscher)
6. Dan Nelson
7. Brendan McElhaney
8. Ryan Bakke
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