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Straight Up Chicago Investor

Business & Economics Podcasts

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.

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.

Location:

United States

Description:

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.

Language:

English


Episodes

Episode 169: How To Leverage Chicago’s Transit-Oriented Development Incentives with Chicago Cityscape

9/29/2022
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...

Duration:00:57:09

Episode 168: Breaking Down Bridgeport Block by Block with Ada Li

9/22/2022
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...

Duration:00:49:32

Episode 167: When Should I Lock My Interest Rate, and What Are The Different Rate Lock Options?

9/20/2022
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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:11:47

Episode 166: BiggerPockets J Scott Breaks Down the Economy, Our Debt Crisis, and the Real Estate Market Cycle

9/15/2022
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...

Duration:00:57:31

Episode 165: From Chicago Househacker, to Out of State Investor, to Leaving Her W2 Job with Kory Dieter

9/8/2022
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...

Duration:00:49:38

Episode 164: Replacement Cost vs Actual Cash Value

9/6/2022
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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:09:31

Episode 163: From Listing Agent to Acquiring and Managing Hundreds of Units on Chicago’s Northside with John McGeown

9/1/2022
Are you looking to learn about acquiring and managing multifamily properties in Chicago’s Northside? If so, you’ll get great value out of this show! John starts by talking about his military background and how that has served him in his real estate career. He provides details on managing his first large scale, multifamily property and how that success propelled his growth. John gets granular on rehabbing occupied buildings, the emergence of some northside neighborhoods, and managing...

Duration:00:45:11

Episode 162: Property Management in Chicago’s Southside with Tim Harstead

8/25/2022
Looking for insight on the nuances of acquiring and managing properties on the south side of Chicago? If so, this episode is for you! Tim starts by talking about his start in real estate and how he identified a need for quality property management on the south side. He provides insight on tenant screening, underwriting expenses, and subsidized housing for the C/D class assets he operates. Tim gets granular on the housing stock, values, and neighborhood borders in the Chicago Lawn, West...

Duration:00:46:28

Episode 161: How financing for Chicago Non Conforming units just got easier.

8/23/2022
What are the recent changes within Freddie Mac that now allows for financing the rehab of an ADU project? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Link: https://perryfarella.com/blog/ ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:11:09

Episode 160: Comparing Chicago To Several Midwest Markets with Brian Kochendorfer

8/18/2022
Brian Kochendorfer returns to the show after 2 years! This time around Brian provides an objective analysis on how his investment properties in Indiana and Ohio compared to his Chicago portfolio. Brian kicks things off by sharing his investment parameters and how he ended up pursuing opportunities in Ohio and Indiana in addition to Chicago. He dives deep into the nuances of acquiring, repositioning, and managing assets in those other markets. Brian speaks to differences in tenant...

Duration:00:50:35

Episode 159: From Successful BRRRR to Major Project Hurdles in Chicago’s Western Suburbs with Zach Gring

8/11/2022
From successful BRRRR to a delayed, over-budget project, Zach Gring shares lessons learned from his investing journey! Zack starts by explaining how he established an asset class to focus on and the reasons for his criteria. He talks through a successful BRRRR project in Batavia and speaks to managing the rehab of a tenant-occupied property. He also shares some lessons learned from his delayed project in Glen Ellyn. Throughout this episode, Zach shares the importance of establishing a...

Duration:00:46:27

Episode 158: Straight Up Tues Tip 34

8/9/2022
What is builder's risk insurance and as an investor why do I need to be aware of builder's risk insurance? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:07:52

Episode 157: Investing in Chicago Midterm Rentals with Rishi Bajaj

8/4/2022
After staying in an Airbnb while on vacation, Rishi Bajaj realized how we can leverage this strategy and used midterm rentals to multiply his rental income! Rishi shares how he got the idea to venture out into the niche space of midterm rentals. He talks about furnishing, costs, and additional considerations when comparing midterm rentals to traditional long-term rentals. He dives into why he sees value and has been investing in some south side neighborhoods and also shares the...

Duration:00:58:09

Episode 156: A Decade of Grinding and Succeeding on Chicago’s Northside with Joe Smazal

7/28/2022
It first took Joe Smazal of Interra Realty six years to sell $100M of multifamily real estate. Six months into 2022, Joe has already sold $100M of assets THIS YEAR ALONE! Joe explains how he left his stable day job to become a Chicago commercial broker, and the growing pains and hustle required to get started. He then speaks to the importance of developing relationships for increased deal flow and identifying areas of focus to become a trusted expert in your market. In classic SUCI fashion,...

Duration:00:48:57

Episode 155: Straight Up Tues Tip 33

7/26/2022
What are some of the useful technologies/apps that can help you scale your REI business? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bolanle Ogunmakin, Quality Builders Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:13:41

Episode 154: Scaling From a Duplex to a $100 Million Portfolio in Chicago’s North and Northwest Side with Jeff Weinberg

7/21/2022
Jeff Weinberg of Drexel Properties joins us to discuss the importance of systems and relationships when scaling a large Chicago Real Estate portfolio. Jeff kicks things off by talking about his start in real estate and leaving his W2 job to pursue his passion full time. He jumps into the mindset and strategies that will help in scaling a portfolio. Jeff drops street level knowledge on the North and Northwest side and explains why he is bullish on Chicago. Throughout the show, Jeff...

Duration:00:55:12

Episode 153: Building Wealth via Long-Term Real Estate Investments in Chicago with Bill Himmelstein

7/14/2022
Bill Himmelstein of Tenant Advisory Group drops in to share great insight on long-term investing and reminds us that real estate is not a “get rich quick” but rather a “get wealthy slowly” investment. Bill starts by talking about his start in real estate and his experience with multi-family investing. He gets granular by speaking to the effect of rising interest rates on the market and also explains investing with partners. Bill emphasizes the importance of living below your means and...

Duration:00:54:23

Episode 152: Straight Up Tues Tip 32

7/12/2022
What is the NBOA Summer Soiree and how can investors benefit from this event? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Mike Glasser of NBOA Link: https://www.straightupchicagoinvestor.com/podcast/episode-37-the-nboa---your-ally-and-voice-as-a-chicagoland-housing-provider ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:11:44

Episode 151: Dissecting Property Taxes on your Chicagoland Properties with Cook County Assessor Fritz Kaegi

7/7/2022
Ever wonder how your Cook County properties are assessed and how taxes are calculated? Cook County Assessor Fritz Kaegi presents valuable info on property taxes and the overall mission of his office! Fritz starts by sharing his background and how it allowed him to seamlessly step in and improve processes as the Assessor. He talks about his office’s responsibilities and some of the common misconceptions the public may have. Fritz elaborates on the massive amount of data involved with...

Duration:00:52:46

Episode 150: Mastering Multi-Family to Propel Your Chicagoland Investments with Rod Khlief

6/30/2022
As many may already know, Rod Khleif is a multifamily real estate investor, business consultant, and high-performance coach. In today’s show, Rod focuses heavily on being prepared to take action as opportunities arise during a changing market like the one we are in today! Rod starts off by speaking about the huge loss he experienced during the last housing crash and how he was able to bounce back stronger. He elaborates on the anticipated recession and on what investors should be doing to...

Duration:00:39:21