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Straight Up Chicago Investor

Straight Up Chicago Investor
Real Estate Investment
Chicago Real Estate
Real Estate Investing
Rehab Draw Process
Construction Loans
Operating Agreement
Chicago Real Estate Market
Chicago
Property Management
Appraisal Process
Multifamily Investments
Renovo Financial
Rental Market
Housing Provider Tips
Investment Strategies
Insurance Claims
Cash Flow
Social Media In Real Estate
Decluttering
Real Estate

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 weeklyEpisodes440Founded6 years ago
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InvestingBusinessCareers

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Artwork for Straight Up Chicago Investor

Latest Episodes

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 Chang... more

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Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and Efficiency!

Joe starts with a story on acquiring a mixed-use building to establish his bu... more

YouTube

What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Mike Glasser & Aron Borstein, NBOA PAC... more

Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward!

Alderman Villegas starts by discussing how zoning changes can be ut... more

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Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Rahm Emanuel
Former mayor of Chicago; ambassador and potential presidential candidate
Former Mayor of Chicago
Episode: Episode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
Gil Villegas
Alderman, 36th Ward
City of Chicago
Episode: Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Reed Meyer
Owner of Lease312, experienced in real estate investment and leasing in Chicago
Lease312
Episode: Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer
Darryl Jacobs
Expert in tax credit finance and partner at Ginsberg Jacobs
Ginsberg Jacobs
Episode: Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
Mike Scanlon
Real estate investor and broker focused on Chicago properties
The Axon Group
Episode: Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
Jessica Erickson
Economic development expert with experience in urban planning and community development
Episode: Episode 426: Reshaping Suburban Woodstock with Jessica Erickson
Ryan Smith
Top REO agent and guest
Smith REO Group
Episode: Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith
Jonathan Klemm
Investor and owner of Quality Builders
Quality Builders
Episode: Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm
Alec Greenberg
Co-owner of Base 3 and Staffolio, investor and property manager in the Chicagoland area.
Episode: Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1

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 418 ratings
  • Great podcast

    Also full of good insights!

    Apple Podcasts
    5
    Butta s
    United States18 days 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 States2 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 States3 months ago
  • Such a good find

    Such a good show! Tip after tip and so much knowledge. I even reached out to Mark and he responded on his personal cell and was super helpful with a management question I had.

    The stories of the guests are so enlightening and makes you feel like your struggles with RE are not so uncommon!

    Apple Podcasts
    5
    Eva the Chicago investor
    United States4 months ago
  • A great show for learning about Real Estate

    A great show for learning about Real Estate; while it focuses on the Chicago market, many principles of real estate apply to any market.

    Apple Podcasts
    5
    Lawrence Dunning
    United States4 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 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
Q: Which candidates has the PAC endorsed for the March elections, and what does that signify?
The PAC endorsed Cook County Assessor Patrick Hines and Cook County Board President Brendan Riley, signaling a push for new leadership and policy direction in key offices.
Episode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
Q: What is the March 11th event about and who is the featured speaker?
It's an evening with Rahm Emanuel, former mayor, as the featured speaker; the event is part of ongoing efforts to engage the real estate community with policymakers.
Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Q: How do you handle community input when a project is proposed?
He prioritizes inclusive community meetings, presents clear options (e.g., different unit counts), and talks through tax revenue implications to help residents understand the trade-offs and benefits.
Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Q: What piece of advice would you give someone buying their first property?
Dedicate significant time, understand that real estate is not a nine-to-five job, and be prepared for ongoing management and problem-solving, with a focus on long-term equity rather than immediate cash flow.
Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Q: What is your competitive advantage as an alderman?
Villegas notes his pragmatic, data-driven approach, negotiation skills, and hands-on leadership—combining development experience with an ability to build coalitions and move projects forward while engaging communities.

Audience Metrics

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

Listeners per Episode
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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. BiggerPockets Real Estate Podcast
2. Real Estate Rookie
3. BiggerPockets Money Podcast
4. Afford Anything
5. All the Hacks: Money, Points & Life

How many episodes of Straight Up Chicago Investor are there?

Straight Up Chicago Investor launched 6 years ago and published 440 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. Rahm Emanuel
2. Gil Villegas
3. Reed Meyer
4. Darryl Jacobs
5. Mike Scanlon
6. Jessica Erickson
7. Ryan Smith
8. Jonathan Klemm

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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