

Straight Up Chicago Investor
Straight Up Chicago Investor
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.
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.
Episodes
Mentioned books

Nov 1, 2022 • 18min
Episode 176: How A Group of Relatively Unknown Investors Took Down a 64-Unit Building Without Being the Highest Offer
A real live example of how beginning investors can separate themselves against known buyers without overpaying. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Derek Kaptanoglu, Essex ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 27, 2022 • 56min
Episode 175: SHOW ME THE INVESTMENTS!!! C&D Class Investing in Chicago's South and West Side Neighborhoods with Corey Oliver
Corey Oliver has over 20 years of experience acquiring and repositioning multifamily buildings in Chicago's South and West Side areas. Corey talks about his start in real estate and how he acquired his first buy and hold buildings in North Lawndale. He speaks to the struggles of investing in C/D class areas including dealing with squatters, non-paying tenants, and gang activity. Corey dives deep on specific pockets including K-Town in North Lawndale, Englewood, and Woodlawn to name a few! He emphasizes the importance of doing your due diligence including thoroughly vetting property managers when investing in these areas. Corey closes with his take on how the city can solve the affordable housing crisis and encourages all of us to be quality housing providers! 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: Corey Oliver, Strength in Management Link: Corey's Instagram Link: Rich Dad Poor Dad (Book Recommendation) Sponsors: Essex Realty Group and State Farm ----------------- Guest Questions 03:47 Housing Provider Tip: Consider raising rents instead of not renewing leases with your tenants! 05:55 Intro to our guest, Corey Oliver! 06:45 Corey talks about his career as a professional sports agent! 10:20 How and where did Corey start investing in real estate? 13:09 Corey explains how properties can fall into disrepair in the areas he invests in. 15:10 Corey talks about K-Town and North Lawndale in general! 18:06 How is Corey taking advantage of city incentives offered in these South and Westside neighborhoods? 21:50 What is Corey's perspective and outlook on Englewood? 25:10 What are the main differences between Chicago's Southside compared to the Westside? 28:26 How will the Obama library impact the Southside? 32:55 Corey talks about Streetwise! 34:07 How can investors prepare to operate properties in C/D class areas? 36:07 How do you deal with and manage gang activity within your properties? 40:00 How did COVID impact Corey's tenants? 44:40 How can we solve Chicago's affordable housing problem? Wrap Up Questions 48:26 What is Corey's competitive advantage? 49:04 One piece of advice for new investors. 50:20 What do you do for fun? 50:53 Good book, podcast, or self development activity that you would recommend? 51:07 Local Network Recommendation? 51:45 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 20, 2022 • 47min
Episode 174: What Every Real Estate Investor Needs to Know About Appliances with Local Chicago Vendor Kevin Krasney
Kevin Krasney is the third-generation owner of Cole's Appliances, which is still situated on the same Lincoln Ave corner in North Center. Kevin talks about his family-owned and operated business and how Cole's provides tremendous value to investors. He walks through the appliance ordering and installation process and how the recent supply chain issues played into this process. Kevin gets granular on different manufacturers and the quality of their products. Throughout the episode, Kevin shares insight on things investors should keep in mind when purchasing appliances to ensure they're delivered/installed on schedule, and to ensure investors are buying the best product for their need! 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: Kevin Krasney, Cole's Appliance and Furniture Co Link: All In Podcast Link: Broken Record Podcast Link: Matt Kustusch (Network Recommendation) Link: Chop Shop Sponsors: Essex Realty Group and State Farm ----------------- Guest Questions 02:11 Housing Provider Tip: Celebrate the wins and enjoy the journey of building your real estate portfolio! 04:48 Intro to our guest, Kevin Krasney! 06:26 Kevin talks about the mindset of keeping the family appliance business small rather than opening more stores! 07:30 How has the supply chain changed over the last couple years? 13:00 Kevin discusses the workflow from appliance ordering to installation! 17:12 Who are the major manufacturers and how does their quality compare to each other? 18:32 What are some things investors can do to minimize appliance repairs? 22:48 Kevin gives a checklist for things required to install a kitchen appliance package. 25:44 How do you determine whether to repair or replace an appliance? 30:06 What are Kevin's thoughts on coin-operated vs electronic payment laundry machines? 33:32 What is Kevin's outlook on the appliance industry? 36:34 How can one determine the fuel source on an appliance? Wrap Up Questions 41:10 What is Kevin's competitive advantage? 41:50 One piece of advice for new investors. 43:11 What do you do for fun? 44:00 Good book, podcast, or self-development activity that you would recommend? 44:20 Local Network Recommendation? 45:03 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 18, 2022 • 13min
Episode 173: What Investors Need to Know to Obtain Commercial Financing in the Upcoming 6-12 Months
What are lenders taking a harder look at in this market? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 13, 2022 • 51min
Episode 172: The Ins & Outs of Chicago's North Lawndale Neighborhood with Robert Waz
Robert Waz of Exterplexy Real Estate & Management joins us to discuss the ins and outs of investing in the North Lawndale neighborhood. Robert kicks things off by explaining why he started investing in North Lawndale. He dives into unforeseen challenges and underwriting considerations to ensure investors accurately account for all expenses and. Robert goes deep into the neighborhood, including its boundaries, different pockets, the building stock, and planned developments in North Lawndale. Throughout the episode, Robert emphasizes the importance of being hands on with property management as a key to success in this neighborhood! 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: Robert Waz, Exterplexy Real Estate & Management Link: The City Podcast (North Lawndale Episodes) Link: Basic Economics (Book Recommendation) Link: SUCI Ep 45 - Jack Crane with CIC ----------------- Guest Questions 02:30 Housing Provider Tip: Be sure that your property's exterior is sealed to prevent animals from getting in! 04:22 Intro to our guest, Robert Waz! 05:26 Why did Robert choose to start investing in North Lawndale? 06:31 Robert talks about his first property in North Lawndale! 08:20 What were some unforeseen challenges of investing in North Lawndale? 12:57 What was the timeframe of Robert's first renovation project? 16:04 Robert talks about underestimating expenses in C/D class neighborhoods! 20:19 Robert talks about North Lawndale's boundaries, building stock, and more neighborhood characteristics! 27:19 What are some ballpark numbers for rental properties in this area? 29:33 Robert discusses CHA vs Market rate tenants. 33:37 What are some developments going on in North Lawndale? 38:49 What do the next 2-3 years look like for Robert and his team? Wrap Up Questions 43:22 What is Robert's competitive advantage? 43:51 One piece of advice for new investors. 44:35 What do you do for fun? 45:52 Good book, podcast, or self development activity that you would recommend? 46:49 Local Network Recommendation? 48:10 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 6, 2022 • 49min
Episode 171: From the East Side to the West Side, Sonia Del Real Explains the Genesis of the Latino Real Estate Investors' Council
Sonia Del Real of Third City Consulting and LREIC join us to discuss her involvement with Chicago Housing Provider Advocacy groups and how investors from all ethnicities can benefit from this group. Sonia shares her background as a second-generation immigrant and a Chicago native along with her investing journey prior to the housing crash. She speaks to her transition into education and advocacy for Latino Housing Providers. Sonia provides information regarding LREIC (Latino Real Estate Investors Council), their mission statement, and the benefits of being a member. She closes with strong words on the importance of getting involved with advocacy groups and being around like-minded, experienced individuals that can propel you and your portfolio to the next level! 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: Sonia Del Real, Third City Consulting and Latino Real Estate Investors Council Link: LREIC Website Link: SUCI Ep 37 - Mike Glasser Link: Cashflow Quadrant (Book Recommendation) ----------------- Guest Questions 02:52 Housing Provider Tip: Make sure you clean your gutters this fall season! 04:44 Intro to our guest, Sonia Del Rey! 05:47 Sonia talks about growing up in Chicago as a second-generation immigrant. 10:46 What is CAPS? 13:37 Sonia talks about her investing journey prior to the housing crash! 18:05 What was Sonia's main motivation for getting into education? 25:23 What is LREIC (Latino Real Estate Investors Council)? 27:47 What are the benefits of being a member of LREIC? 31:46 Sonia provides advice for anyone trying to start an advocacy group! Wrap Up Questions 40:54 What is Sonia's competitive advantage? 42:11 One piece of advice for new investors. 42:50 What do you do for fun? 43:26 Good book, podcast, or self-development activity that you would recommend? 44:04 Local Network Recommendation? 45:46 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Oct 4, 2022 • 11min
Episode 170: What Does Commercial Lending Look Like in the Foreseeable Future?
How does the recent rate hikes affect investors' ability to borrow moving forward? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Sep 29, 2022 • 57min
Episode 169: 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 ----------------- 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! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Sep 22, 2022 • 50min
Episode 168: 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 ----------------- 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! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Sep 20, 2022 • 12min
Episode 167: 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.


