

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

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.

Sep 15, 2022 • 58min
Episode 166: 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 ----------------- 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! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Sep 8, 2022 • 50min
Episode 165: 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 ----------------- 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! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Sep 6, 2022 • 10min
Episode 164: 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.


