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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 183: Forty-Six Years of Chicago Real Estate Knowledge with Pioneer Vince DePaul

12/1/2022
Vince begins by talking about his previous career as a rockstar manager (Styx)! He shares stories about Roseland and Humboldt Park in the 60s and 70s. Vince transitions into his journey as both a real estate broker and investor. He dives deep into the pros/cons of getting a broker’s license as an investor and the requirements to get licensed. Throughout the episode, Vince speaks to the power of real estate as a wealth generator and the importance of education! If you enjoy today’s episode,...

Duration:00:54:34

Episode 182: How to Vet Contractors For Your Chicago Rehab

11/29/2022
What are the steps I should take to vet my Chicago contractors? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bolanle Ogunmakin, Quality Builders Link: Straight Up Chicago Investor Episode 76 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:15:28

Episode 181: Million Dollar Batavia 5-Flat From Networking to Closing (POV)

11/24/2022
Return guests Bibek Das, Eric Workman, and Matt LaCosse join us to discuss a 5-unit deal with a lot of hair on it! Matt (buyer on this deal) starts by talking about how our very own Mark Ainley (buyer’s agent) brought this 5-unit property in Batavia to his attention. Eric (the lender on this deal) dives into the lending aspect of this deal and the group discusses the offer formulation and negotiation process. Bibek (the buyer’s attorney) explains the meaning of appraisal waivers and “AS-IS”...

Duration:01:00:41

Episode 180: From Prison to Real Estate Profits; A Transformational Chicago Journey Against All Odds with Mike Baker

11/17/2022
From a rough upbringing to a successful REI career in Chicago, Mike Baker joins us to discuss his journey and his vast knowledge on wholesaling, flipping, and consulting. Mike begins by outlining his troubled past involving drugs, gangs, and prison. He shares some of the lessons learned in prison and the mindset shift required to get started and to succeed in real estate. Mike, Mark, and Tom share shocking stories about rehabbing in distressed neighborhoods. Mike closes by explaining how...

Duration:00:44:15

Episode 179: How to Reduce the Cost of your Chicago Lawn

11/15/2022
What are my options to remove maintenance costs on smaller pieces of lawns? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: James Galvin, Chicago Lawn To Garden ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Duration:00:12:06

Episode 178: Rising Rates, 2/1 Buydowns, and The Foreseeable Future of Investing and Lending with Rock Star Lender (and Drummer!) Sam Sharp

11/10/2022
Sam Sharp has over 20 years experience in the Mortgage Industry and joins us to discuss rising interest rates. Sam begins by talking about his vast experience in the mortgage industry and the lending environment during the last housing crash. He shares tips that have helped him be a top-producing loan originator and provides advice for professionals trying to build their brand. Sam gives his take on the million-dollar question: WHERE ARE RATES GOING AND IS NOW A GOOD TIME TO BUY?! He...

Duration:01:04:14

Episode 177: How to Analyze and Buy Mixed-Use, Retail, and other Commercial Real Estate Assets in Chicago with Danny Spitz

11/3/2022
Danny Spitz of Greenstone Partners joins us to discuss the ins and outs of investing in commercial real estate. Danny kicks things off by sharing his start in real estate with a 3-flat in Bridgeport. He explains the differences between residential and commercial properties including insight on taxes and financing those assets. Danny speaks to the types of tenants and leases on mixed-use, retail, and office spaces. Throughout the episode, Danny emphasizes the importance of building...

Duration:00:56:54

Episode 176: How A Group of Relatively Unknown Investors Took Down a 64-Unit Building Without Being the Highest Offer

11/1/2022
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.

Duration:00:17:39

Episode 175: SHOW ME THE INVESTMENTS!!! C&D Class Investing in Chicago’s South and West Side Neighborhoods with Corey Oliver

10/27/2022
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!...

Duration:00:55:30

Episode 174: What Every Real Estate Investor Needs to Know About Appliances with Local Chicago Vendor Kevin Krasney

10/20/2022
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...

Duration:00:47:25

Episode 173: What Investors Need to Know to Obtain Commercial Financing in the Upcoming 6-12 Months

10/18/2022
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.

Duration:00:13:04

Episode 172: The Ins & Outs of Chicago’s North Lawndale Neighborhood with Robert Waz

10/13/2022
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....

Duration:00:51:06

Episode 171: From the East Side to the West Side, Sonia Del Real Explains the Genesis of the Latino Real Estate Investors’ Council

10/6/2022
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...

Episode 170: What Does Commercial Lending Look Like in the Foreseeable Future?

10/4/2022
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.

Duration:00:11:09

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