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Straight Up Chicago Investor

Straight Up Chicago Investor
Real Estate Investing
Chicago Real Estate
Real Estate Investment
Chicago
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
Rental Market
Real Estate Investment Strategies
Investment Properties

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 weeklyEpisodes450Founded6 years ago
Number of ListenersCategories
BusinessCareersInvesting

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Artwork for Straight Up Chicago Investor

Latest Episodes

What are the main differences in the 8.0 CAR contract vs the previous 7.0?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Chance Badertscher, Chance The Lawyer

Email the Show: StraightUpChicagoInvestor@gmail.com... more

Dan Nelson is a real estate agent and investor with over 2 decades of experience flipping properties and buying rentals!

Dan jumps right in by explaining his start in real estate and how success in poker helped fund his real estate business! He bre... more

YouTube

Brendan McElhaney, founder of Cash for Chicago Houses, is a real estate wholesaler and investor who specializes in sourcing off-market deals through direct-to-seller marketing!

Brendan explains how he started in real estate with a house hack and ho... more

YouTube

How do I best prepare for an upcoming appraisal?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Tom & Mark, Straight Up Chicago Investor

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Tea... more

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Recent Guests

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
Josh Bandoch
Author and Head of Policy at the Illinois Policy Institute; real estate investor-focused author
Illinois Policy Institute
Episode: Episode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations
Jay Patel
West Side Investors partner, real estate investor
West Side Investors
Episode: Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
Tedi Nati
Partner, real estate investor, builds financial and back-end systems
West Side Investors
Episode: Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
Samuel Pavlovcik
Architect, Pavlovcik Architecture
Pavlovcik Architecture
Episode: Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik
Joe Konopacki
Real estate investor and founder of Insight Property Services
Insight Property Services
Episode: Episode 437: Energy Efficiency in Chicago Real Estate with Joe Konopacki
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

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 421 ratings
  • #1 Podcast about Chicago Real Estate

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

    Apple Podcasts
    5
    Hogggjbegf
    United Statesa month ago
  • Great podcast

    Also full of good insights!

    Apple Podcasts
    5
    Butta s
    United States2 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 States3 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 States4 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 States5 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 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.
Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg
Q: How did you structure the first development deal and align incentives with investors?
We raised two million in equity, used a preferred return (10%), and charged acquisition and construction fees while acting as the GC. The IRR target was ambitious, and while we aimed for around 20%, we achieved about a 48 IRR by selling the asset in a year. The key was presenting a credible plan, leveraging an existing relationship with a lender, and keeping investors aligned with the project's risk and reward.
Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg
Q: What was the initial pivot that led you to move from GC work to developing in-house projects?
The realization came during an owner-architect-contractor meeting when I understood that the developers controlled the project by not only planning but also managing construction. Once I saw that control and certainty, I presented a case to my partners and we committed to taking on full development, including capital stack and construction management.
Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
Q: What happens if the project changes after the loan closes?
If changes occur, you typically need a change order and can be limited by the initial draw plan; large changes may require additional funding or renegotiation, underscoring the need for accurate up-front scope and contingency.
Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
Q: How do funds get released during renovation loans?
The funds can be released via servicing departments of lenders who maintain the loan, sometimes as direct ACH deposits or checks made out to both borrower and contractor, depending on the lender's servicing arrangement.

Audience Metrics

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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. Real Estate Chicago Style Podcast
2. The Best Ever CRE Show
3. BiggerPockets Real Estate Podcast
4. The David Greene Show
5. Real Estate Rookie

How many episodes of Straight Up Chicago Investor are there?

Straight Up Chicago Investor launched 6 years ago and published 450 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. Ryan Bakke
2. Adam Friedberg
3. Josh Bandoch
4. Jay Patel
5. Tedi Nati
6. Samuel Pavlovcik
7. Joe Konopacki
8. Rahm Emanuel

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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