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Artwork for Straight Up Chicago Investor

Straight Up Chicago Investor

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

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 weeklyEpisodes417Founded6 years ago
Number of ListenersCategories
InvestingCareersBusiness

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Artwork for Straight Up Chicago Investor

Latest Episodes

Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical areas of focus and on understanding risks when developing product that will set the top co... more

SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs!

Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granula... more

When do I have to have my cost segregation done to ensure it is good for my 2025 taxes?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Cost Seg Kev from CSSI

Email the Show: StraightUpChicagoInvestor@gmail.com more

Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio.

Luke kicks things off by sharing how he acquired his first house hack and provides insights... more

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Recent Guests

Kostet Kev
Expert in cost segregation and returns to discuss related tax strategies.
CSSI
Episode: Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev
Eli Goodman
Founder and owner of Illinois Real Estate Buyers
Illinois Real Estate Buyers
Episode: Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman
Moises Correa
Owner of Proximo Equity Group and real estate investor
Proximo Equity Group
Episode: Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa
Joe Smazal
Real estate broker with a focus on multifamily properties in Chicago
Smazal Apartments
Episode: Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Lantz Kurzawinski
A young real estate investor who acquired four properties before turning 21
Episode: Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski
Jason Wagner
Real estate agent and investor, owner of Greystone Realty
Greystone Realty
Episode: Episode 402: Looking At Chicago Investing Differently with Jason Wagner
Chris Puleo
Experienced mortgage professional and investor
Puleo Group, Neighborhood Loans
Episode: Episode 401: Interest Rates Are Coming Down According to Chris Puleo
Kevin Rocio
Real estate investor, broker and former lender
Episode: Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio
Paul de Luca
A house hacker who has house hacked four separate times and has extensive knowledge to share with listeners.
The Axon Group
Episode: Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca

Hosts

Tom Schalkross
Co-host of the show with significant experience in Chicago real estate investing and property management, bringing valuable insights to discussions.
Mark Ainley
Co-host known for expertise in the Chicago real estate scene, facilitating discussions on effective investment strategies and local market dynamics.

Reviews

5.0 out of 5 stars from 408 ratings
  • Laugh and Learn

    Informative and relatable podcast. This is how you win!

    Apple Podcasts
    5
    Luke He’ll
    United Statesa month ago
  • President

    Great time and informative show

    Apple Podcasts
    5
    Jim Paul1
    United States2 months ago
  • Awesome

    Great hosts and awesome insights into all things Chicago RE!

    Apple Podcasts
    5
    rishi917rishi
    United States3 months ago
  • Best Chicago RE Podcast There Is

    10/10 must listen

    Apple Podcasts
    5
    TRRRRUTH
    United States4 months ago
  • Great show, great people

    This is an amazing podcast that dives into the ins and outs of owning, managing, leasing, and everything real estate. It was a pleasure to be featured on the show and look forward to following the guys and how they serve this great industry.

    Apple Podcasts
    5
    spirtually messed up
    United States4 months ago

Listeners Say

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

Listeners find the content to be extremely informative and engaging, often highlighting the depth of knowledge shared by the hosts and guests.
Many appreciate the combination of personal experiences and professional advice, affirming the practical nature of the topics discussed.
Feedback indicates that the podcast serves as a crucial resource for understanding the Chicago real estate landscape, particularly for new investors.

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Talking Points

Recent interactions between the hosts and their guests.

Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
Q: What is the one piece of advice you would tell someone that is yet to buy their first property here in Chicago?
Do your due diligence and then go for it without talking to too many people.
Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman
Q: What advice would you give someone starting in real estate?
Get your ducks lined up in a row and do as much due diligence as you can up front.
Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman
Q: How did you start in real estate?
Eli Goodman shares that he initially got into real estate through a friend who wanted to be a real estate agent and, after some failed ventures, decided to partner with him.
Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Q: What advice do you have for new investors?
Buy a property that they would be happy to own for a long time, ensuring they have a solid investment regardless of market fluctuations.
Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Q: What struggles are you seeing in getting deals across the finish line?
The buyer and seller psychology is quite fragile now, making it easy for deals to fall apart due to concerns about market conditions.

Audience Metrics

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

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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?

Focused on real estate investment within Chicago and its surrounding areas, this show features detailed discussions that aim to provide valuable insights for both new and seasoned investors. Topics range from property management and leasing strategies to the nuances of house hacking, cost segregation, and the legal aspects of real estate partnerships. Guests typically include successful investors, property managers, and industry experts who share their personal experiences, challenges, and effective strategies. Notably, the approach combines practical advice with community-based insights, creating a resource aimed at empowering listeners to navigate the Chicago real estate market effectively.

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How many listeners does Straight Up Chicago Investor get?

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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 Chicago Style Podcast
3. On The Market
4. The Real Estate Guys Radio Show - Real Estate Investing Education for Effective Action
5. Real Estate Rookie

How many episodes of Straight Up Chicago Investor are there?

Straight Up Chicago Investor launched 6 years ago and published 417 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Straight Up Chicago Investor?

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What guests have appeared on Straight Up Chicago Investor?

Recent guests on Straight Up Chicago Investor include:

1. Kostet Kev
2. Eli Goodman
3. Moises Correa
4. Joe Smazal
5. Lantz Kurzawinski
6. Jason Wagner
7. Chris Puleo
8. Kevin Rocio

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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