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Artwork for Straight Up Chicago Investor

Straight Up Chicago Investor

Straight Up Chicago Investor
Real Estate Investing
Chicago Real Estate
Chicago
Real Estate Investment
Property Management
Real Estate
Chicago Real Estate Market
House Hacking
Affordable Housing
Networking
Interest Rates
Illinois
NBOA
Cost Segregation
Operating Agreement
Investment Strategies
Insurance Claims
Wholesaling
Rental Market
Real Estate Investment Strategies

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

PublishesTwice weeklyEpisodes459Founded6 years ago
Number of ListenersCategories
InvestingCareersBusiness

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Artwork for Straight Up Chicago Investor

Latest Episodes

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

YouTube

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

YouTube

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

YouTube

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Igor Kajpust
Real estate investor; founder of Evolved Property Group
Evolved Property Group
Episode: Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust
Aaron Zimmerman
Tax expert guest, discussing tax changes for real estate investors
Brick House CPAs
Episode: Episode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure
Alderman Bennett Lawson
Alderman of the 44th Ward in Chicago, instrumental in ADU ordinance and ward development
City of Chicago, 44th Ward
Episode: Episode 450: Alderman Bennett Lawson & The 44th Ward
Michael Scanlon
Friend of the pod, investor and Axon Group leader
Axon Group
Episode: Episode 449: Zero to Thirty Units Creatively with Mike Scanlon
Chance The Lawyer (Chance Badertscher)
Attorney, real estate finance and contracts expert
Chance The Lawyer
Episode: Episode 448: Understanding the CAR 8.0 Real Estate Contract with Chance Badertscher
Dan Nelson
Investor, broker, entrepreneur
Dan Loves Houses (investor/broker)
Episode: Episode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Brendan McElhaney
Wholesaler and real estate investor, Cash for Chicago Homes
Cash for Chicago Homes
Episode: Episode 446: Brendan McElhaney's Journey To Wholesaling Deal Flow
Ryan Bakke
Owner of Tax Strategy 365
Tax Strategy 365
Episode: Episode 444: Leveraging Tax Strategy to Boost ROI with Ryan Bakke
Adam Friedberg
Developer at Mavrek Development
Mavrek Development
Episode: Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg

Hosts

Tom Schellcross
Host with substantial involvement in the Chicago real estate scene.
Mark Ainley
Co-host focused on data-driven real estate investing and market insights.

Reviews

5.0 out of 5 stars from 426 ratings
  • Investing in Chicago? Must listen

    Mark has so much information and experience in the Chicago market. This show is a must-follow!

    Apple Podcasts
    5
    stacey ss
    United States2 months ago
  • #1 Podcast about Chicago Real Estate

    Best podcast about insights on the Chicagoland real estate market and amazing hosts!

    Apple Podcasts
    5
    Hogggjbegf
    United States2 months ago
  • Great podcast

    Also full of good insights!

    Apple Podcasts
    5
    Butta s
    United States3 months ago
  • Great resource for anyone trying to actually understand the city, not just the headlines

    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

    Apple Podcasts
    5
    Shizer Soze
    United States4 months ago
  • Very Helpful

    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!

    Apple Podcasts
    5
    KingArthurThe3rd
    United States6 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Listeners praise the in-depth Chicago-specific knowledge and actionable tips.
Local focus and practical, boots-on-the-ground insights are consistent strengths.
Guests are insightful and the hosts are responsive, adding real value for real estate professionals.

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Talking Points

Recent interactions between the hosts and their guests.

Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust
Q: How many deals have you done?
The guest replied that he was close to 500 deals.
Episode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Q: What is your approach to building a team with investors in mind?
Seek people who want to learn, are genuinely curious, and are willing to work hard; provide value beyond the closing, act as a resource, and build a scalable, referral-driven business model.
Episode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Q: How do you set expectations for out-of-state investors considering Chicago?
Understand their goals beyond year-one cash flow, explain the long-term appreciation potential, and tailor buy-box strategies around submarkets with strong fundamentals and growth trajectories.
Episode 447: Dan Nelson Chicago Investment Minded Power Broker & Investor
Q: What advice would you tell someone that has yet to buy their first property here in Chicago?
Start with practical tools like rentalcalculator.com to analyze deals, keep the process simple, and focus on buying a property while letting tenants pay the way; the emphasis is on action over overreliance on information.
Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg
Q: What major challenges did you face with COVID, and how did you respond to protect value for investors?
COVID required us to pivot architectural plans to include more outdoor space and reconsider unit sizes. We communicated transparently with investors about the changes, showing that the plan could be updated at no extra cost. Our ability to adapt and maintain open dialogue with lenders and investors was crucial to preserving value during a highly uncertain period.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Straight Up Chicago Investor

What is Straight Up Chicago Investor about and what kind of topics does it cover?

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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Which podcasts are similar to Straight Up Chicago Investor?

These podcasts share a similar audience with Straight Up Chicago Investor:

1. Real Estate Chicago Style Podcast
2. BiggerPockets Real Estate Podcast
3. Lifetime Cash Flow Through Real Estate Investing
4. Real Estate Rookie
5. The Best Ever CRE Show

How many episodes of Straight Up Chicago Investor are there?

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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What guests have appeared on Straight Up Chicago Investor?

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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