120 episodes

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 Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.

Straight Up Chicago Investor Straight Up Chicago Investor

    • Business
    • 5.0 • 208 Ratings

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 Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.

    How To Leverage Chicago’s Transit-Oriented Development Incentives with Chicago Cityscape

    How To Leverage Chicago’s Transit-Oriented Development Incentives with Chicago Cityscape

    Return guests Casey Smagala and Steven Vance of Chicago Cityscape join us to discuss the revised Transit-Oriented Development (TOD) ordinance and other development trends in Chicago!
    Casey and Steven start off by explaining the TOD ordinance and the changes resulting from the recent revision. They dive deep on the impacted neighborhoods, zoning districts, and provisions of the ordinance. Casey and Steven showcase their urban planning backgrounds by weighing in on the impact of current city policies and how they would improve those policies. Lastly, they share why Cityscape is such a powerful data-aggregation software and how it can give Chicago Investors a tremendous competitive advantage!
    If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Casey Smagala and Steven Vance, Chicago Cityscape
    Link: SUCI Ep 97 - Samuel Pavlovcik
    Link: SUCI 112 - Cityscape (1st Episode)
    Link: SUCI Ep 59 - Cost-Seg Kev
    Link: The New Localism (Book Recommendation)
    Link: UCLA Housing Voices Podcast
    Sponsors: Essex Realty Group and Appeal.tax
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    Guest Questions
    03:18 Housing Provider Tip: Use online services by Utility providers to expedite requests!
    06:14 Intro to our guests, Steven Vance and Casey from Chicago Cityscape!
    07:00 What is the TOD ordinance?
    10:26 Who can benefit from the revised TOD ordinance?
    13:22 Steven and Vance talk about accessible dwelling units!
    16:34 Are there de-conversation limitations within the revised TOD ordinance? 
    18:52 Steven and Vance talk about neighborhoods most impacted by the ordinance!
    26:31 How does the ordinance affect parking requirements?
    31:53 How do City policies attempt to control density?
    38:00 What policy changes can investors expect in the near future?
    39:50 How does the City measure the success of their new policies?
    Wrap Up Questions
    43:12 What is Casey’s and Steven’s competitive advantage? 
    43:58 One piece of advice for new investors.
    48:22 What do you do for fun?
    49:18 Good book, podcast, or self development activity that you would recommend? 
    51:24 Local Network Recommendation?
    54:21 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 57 min
    Breaking Down Bridgeport Block by Block with Ada Li

    Breaking Down Bridgeport Block by Block with Ada Li

    Ada Li is a Chicago-based Developer with over 20 years of experience. Ada shares her experience with her family’s construction business, which includes dealing with Chicago Inspectors, zoning changes, and other lessons learned over the years. Ada dives deep into Bridgeport by sharing insight on the different pockets of the neighborhood, how values vary across those areas, and her long-term outlook of the neighborhood. Ada closes this knowledge packed show by providing her take on McKinley Park and Brighton Park!
    If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Ada Li, Winner Construction and Hardscrabble Investments
    Link: Who Not How (Book Recommendation)
    Link: SUCI Ep 43 - RJ and Nicky (Network Recommendation)
    Link: InvestHER Meetup
    Sponsors: GC Reality and Appeal.tax
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    Guest Questions
    02:22 House Provider Tip: Be aware of the new Illinois law requiring 10-year smoke detectors!
    04:16 Intro to our guest, Ada Li!
    08:10 Ada talks about working in the family construction business and the dynamics associated with that.
    10:10 How did the business scale?
    13:48 How can an investor back into a purchase price?
    17:09 Ada shares some lessons learned over the years in construction!
    25:48 Why did Ada and her family decide to invest in Bridgeport?
    28:33 Ada talks about meeting Aldermen when needing Zoning changes!
    30:38 What are Ada’s favorite pockets of Bridgeport?
    33:02 Ada talks about pricing differences within the different pockets of Bridgeport!
    36:35 What is Ada’s outlook on Bridgeport?
    37:58 What does Ada think about McKinley Park and Brighton Park?
    40:03 Ada talks about land value in Bridgeport.
    Wrap Up Questions
    41:23 What is Ada’s competitive advantage? 
    41:58 One piece of advice for new investors.
    42:27 What do you do for fun?
    43:08 Good book, podcast, or self development activity that you would recommend? 
    44:11 Local Network Recommendation?
    44:50 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 49 min
    When Should I Lock My Interest Rate, and What Are The Different Rate Lock Options?

    When Should I Lock My Interest Rate, and What Are The Different Rate Lock Options?

    When should I lock in my mortgage rate in a volatile market, and what is a float-down option?
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Perry Farella, Prime Lending | SUCI Episode 67

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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 11 min
    BiggerPockets J Scott Breaks Down the Economy, Our Debt Crisis, and the Real Estate Market Cycle

    BiggerPockets J Scott Breaks Down the Economy, Our Debt Crisis, and the Real Estate Market Cycle

    Entrepreneur, investor, and best-selling author J Scott of BiggerPockets and Bar Down Investments joins SUCI and drops tremendous wisdom! J shares the mindset and adaptability required to become a successful real estate investor. He draws on his past experience to break down the economic climate by speaking to various topics including inflation, stagflation, the debt crisis, consumer behavior, and the job market. J closes with insight on properly underwriting deals and emphasizes the power of buy-and-hold rental properties as a wealth building tool!
    If you enjoy today’s episode and like what you hear, please leave us a review and share us with a friend!
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: J Scott from BiggerPockets and Bar Down Investments
    Link: The Goal (Book Recommendation)
    Link: Ashley Wilson (Network Recommendation)
    Link: Real Estate by the Numbers (Pre-Order J Scott's New Book)
    Link: Connect with J Scott
    Sponsors: Essex Realty Group and Appeal.tax
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    Guest Questions
    03:21 House Provider Tip: Understand that bull markets may cover up mistakes that wouldn’t be covered in bear markets!
    04:39 Intro to our guest, J Scott!
    05:31 J talks about the mindset required to be successful in real estate!
    12:41 J defines stagflation and talks about its relation to the debt crisis?
    21:02 How does J predict lending will change in the near future?
    27:19 Does J think that the expected recession can be a self-fulfilling prophecy as consumers get fearful and change their behavior? 
    30:52 What is J’s outlook on the job market?
    36:32 Is J still looking for real estate deals and how has his underwriting changed?
    40:41 How can passive investors effectively vet an operator?
    44:50 J shares mistakes he’s made in his investing career!
    49:01 J talks about accounting for expense increases when underwriting deals
    Wrap Up Questions
    50:33 What is J’s competitive advantage? 
    50:59 One piece of advice for new investors.
    51:51 What do you do for fun?
    52:33 Good book, podcast, or self development activity that you would recommend? 
    53:34 Local Network Recommendation?
    54:29 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 57 min
    From Chicago Househacker, to Out of State Investor, to Leaving Her W2 Job with Kory Dieter

    From Chicago Househacker, to Out of State Investor, to Leaving Her W2 Job with Kory Dieter

    Kory Dieter is a Chicago-based is a house hacker and professional out of state investor with a portfolio mix that includes SFRs and small multi-families across 5 markets. In today’s episode Kory shares with us how she started her real estate journey with a house hack in Andersonville to how she was able to leave behind her W2 job. Along the way she’s dabbled in a variety of investing strategies, including house hacking, medium term rentals, BRRRR, and 1031 exchanges, with no signs of stopping now!
    This episode is full of nuggets on deal acquisition and things to keep in mind when looking for your next investment, whether it’s in Chicago or a different market!
    If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Kory Dieter

    Link: http://www.naiopchicago.org/
    Link: https://www.gcrealtyinc.com/brrrr-investment-strategy-must-knows
    Link: https://www.gcrealtyinc.com/blog/house-hacking-101-in-chicago
    Link: https://www.straightupchicagoinvestor.com/house-hacking-calculator
    Link: https://www.straightupchicagoinvestor.com/podcast/episode-43-househacking-scaling-and-large-multifamily-deals-with-one-of-chicagos-best-power-couples
    Sponsors: State Farm and Appeal.tax
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    Guest Questions
    03:30 House Provider Tip: Be Ready To Address Issues When Tenants First Move In
    05:40 Intro to our guest, Kory Dieter!
    06:45 Starting with a househack in Andersonville
    12:15 The importance of knowing the neighborhood

    21:15 Out of State Real Estate Investors Must Have Mindset
    25:50 Pro Forma Vs Actual Is Usually Different in Real Estate Investing
    27:57 Scaling As A House Hacker
    30:58 How To Prepare Your Portfolio For the Future
    34:01 Challenges Faced Transitioning From a W2 To Self Employed Real Estate Investor
    Wrap Up Questions
    42:39 What is Kory’s competitive advantage? 
    43:15 One piece of advice for new investors.
    53:25 What do you do for fun?
    43:42 Good book, podcast, or self development activity that you would recommend? 
    45:02 Local Network Recommendation?
    45:53 How can the listeners learn more about you and provide value to you?
    That’s our show! Thanks for listening!
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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 49 min
    Replacement Cost vs Actual Cash Value

    Replacement Cost vs Actual Cash Value

    What is the difference between actual cash value and replacement cost?
    Connect with Mark and Tom: StraightUpChicagoInvestor.com
    Email the Show: StraightUpChicagoInvestor@gmail.com
    Guest: Josh Steigelmann, State Farm Insurance

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    Production House: Flint Stone Media
    Copyright of Straight Up Chicago Investor 2022.

    • 9 min

Customer Reviews

5.0 out of 5
208 Ratings

208 Ratings

Christi Avelar ,

Amazing!

Love the show! I am a Realtor, property manager and investor, and I find value in every single episode. I look forward to listening to you guys and your guests weekly! Keep up the amazing work!

househackerrr ,

Excellent listen

Learned so much from this show!

Ramirezrm7 ,

Tons of FREE KNOWLEDGE!!!

This is the best Chicago REI podcast! So much information that’s ranges from starter to expert!

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