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...
Author
Straight Up Chicago Investor
Category
Podcast website
Latest episode
Jul 9, 2026
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Episodes
Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants 02.12.2025 12:02
How do I protect myself against potential tenant screening scams? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and...
Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats 27.11.2025 59:11
Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical areas of focus and on understanding risks when developing product that will set the top comparable in a neighborhood. Lawrence provides a great take on his top Chicago neighborhoods for upside and reasoning for why he is bullish. Throughout...
Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows 20.11.2025 42:41
SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs! Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump t...
Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev 18.11.2025 15:46
When do I have to have my cost segregation done to ensure it is good for my 2025 taxes? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Cost Seg Kev from CSSI Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and gi...
Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons 13.11.2025 1:13:42
Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio. Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the...
Episode 411: Shawn Good Creates Opportunity with Off Market Deals 06.11.2025 59:41
Shawn Good is a seasoned attorney and real estate investor with vast experience acquiring and stabilizing off-market real estate. Shawn kicks things off by discussing his first few deals which included a condo and an 8-unit building. He shares some funny stories on unfair partnerships he's been a part of and important points on due diligence when acquiring a property. Shawn explains how joining C...
Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross 04.11.2025 18:35
What the different ways I can adjust my offer to make it more attractive? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn mo...
Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman 30.10.2025 48:27
Eli Goodman of Illinois Real Estate Buyers gives the complete playbook on dealing directly with sellers to acquire off-market deals! Eli starts with explaining the grind it took to get his wholesaling off the ground! He discusses the right way to communicate with distressed sellers to create win-win scenarios and also throws in a few horror stories. Eli shares the various processes for direct to s...
Episode 408: Chicago Suburb Land Development with Jim Paul 23.10.2025 1:04:48
Jim Paul, Director of the ALPS Group, has over 2 decades of experience in land development and receivership. Jim jumps right in by discussing an early 21-acre land development deal and the hurdles he dealt with there! He breaks down his Tuscan Hills and Canterbury Lakes projects - residential developments in Will County, IL. Jim explains how to get creative with land development design and how to...
Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago 21.10.2025 20:07
What are the differences between R2, R3, R4, and R5 zoning? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyIn...
Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa 16.10.2025 1:03:08
Moises Correa, Principal of Proximo Equity Group, leads a team that specializes in value-add multifamily real estate across the Midwest. Moises provides the ins and outs of his first couple house hacks in Avondale and how he burned the boats and left his W2 job after the first one! He explains how he formed partnerships to purchase a large multifamily building in Louisville, KY and gets granular o...
Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal 09.10.2025 1:05:37
Joe Smazal, Senior Managing Partner of Interra Realty, has over a decade of experience selling mid-market apartment buildings and recently surpassed $1 Billion in transaction volume! Joe kicks things off by sharing the genesis and overview of his "Real Estate Chicago Style Podcast"! He reflects on his career's progression and highlights that have led him to crossing the $1 billion mark in total tr...
Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo 07.10.2025 11:32
What are my lending options for a non-owner occupied investor? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCReal...
Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski 02.10.2025 50:22
Lantz Kurzawinski, Marketing Specialist for the Straight Up Chicago Investor Podcast, tells his story of grinding to succeed in real estate at an early age. Lantz explains how he recognized his entrepreneurial spirit at an early age and decided to dive into real estate. He shares his experience as a leasing agent and how that led him to discover his enjoyment for getting his hands dirty. Lantz get...
Episode 402: Looking At Chicago Investing Differently with Jason Wagner 25.09.2025 1:01:02
Jason shares why he chose to invest in Chicago's northwest side and how he's achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset's ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington He...
Episode 401: Interest Rates Are Coming Down According to Chris Puleo 23.09.2025 13:21
Chris Puleo lays out tangible reasons why he feels interest rates will be coming down in the upcoming future. ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you bac...
Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio 18.09.2025 1:01:24
Kevin Rocio, founder of ROC Advisory Group, is an award winning commercial real estate broker, mentor, and investor. Kevin shares how he built a business and sphere of influence in the mortgage lending industry. He discusses his start in commercial real estate and gets granular on various valuation metrics. Kevin talks about the rapid growth of his business during and after the pandemic. He closes...
Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White 11.09.2025 1:05:07
Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI! Micah starts by explaining the ins and outs of his first couple house hacks in Logan Square and North Lawndale. He provides great pointers on proper due diligence to mitigate risk on an investment. Micah shares a hilarious DIY story; moral of the story, hire a professional! He closes w...
Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca 04.09.2025 53:20
Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly real estate agent! Paul jumps right into the nitty gritty of his first couple house hack deals! He gives tips on getting off the ground as a new real estate agent and the 101 on Chicago non-conforming units. Paul shares how he handled various...
Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property? 02.09.2025 21:14
What are the "do's" and "don'ts" when filing an insurance claim? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRea...
Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci 28.08.2025 1:08:56
Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand! Fernando explains his marketing strategy to optimize deal flow despite the low inventory environment. He delves deep into the underwriting and feasibility studies performed on self storage investments to maximize returns. Fernando provides t...
Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew 21.08.2025 1:07:14
Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago's north side! Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He talks about the importance of knowing your market to accurately project rents and pro-formas. Max gets granular on leasing...
Episode 394: The Legal Nuances of Different Real Estate Partnership Structures 19.08.2025 13:19
What do investors need to consider from a legal perspective when setting up new partnerships? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours o...
Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy 14.08.2025 1:01:28
DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits! DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He breaks down the rent-by-the-room strategy as a tool to maximize ROI. DuBois dives deep on VA loans, tax exemptions, an...
Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars 07.08.2025 51:16
Kevin Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003. Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into the benefits of real estate professional status and recent tax code changes by the presidential administration. He also...
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