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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.

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
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Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords

12/11/2025
Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation! Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don'ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and shares horror stories caused by those mistakes! He closes best practices to handle squatters and an outlook on potential changes to the eviction process. 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Zeke McDonald-Lewis, Erwin Law Link: Zeke's LinkedIn Link: SUCI Ep 330 - James Erwin Link: Red Rising (Book Recommendation) Guest Questions: 03:50 Housing Provider Tip - Plan tenant payment plans to clear balances quickly! 05:51 Intro to our guest, Zeke McDonald-Lewis! 12:25 First step in dealing with a non-paying tenant. 19:54 Next steps after serving a 5-day notice. 34:18 Timelines for the eviction process. 38:36 Top eviction mistakes. 44:43 Eviction horror stories! 47:25 Dealing with squatters. 51:01 Zeke's outlook on the eviction process! 55:02 What is your competitive advantage? 55:54 One piece of advice for new investors. 56:31 What do you do for fun? 56:59 Good book, podcast, or self development activity that you would recommend? 57:15 Local Network Recommendation? 58:00 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:00:40

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Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal

12/4/2025
Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings! Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares details on his first 2-unit building in Logan Square and dives deep into top "gotchas" when purchasing 2-4 unit buildings. He closes with a bullish outlook on Chicago particularly the areas surrounding the United Center! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Niko Apostal, Niko Collaborative - Essex 312 Link: The ONE Thing Podcast Link: The Power of Full Engagement (Book Recommendation) Link: SUCI Ep 112 - Chicago Cityscape Guest Questions: 01:58 Housing Provider Tip - Be sure to appeal property taxes particularly with upcoming reassessments! 03:36 Intro to our guest, Niko Apostal! 08:41 Weathering the storm of the real estate crash! 20:53 Lessons learned and tips for starting a real estate brokerage. 30:25 Investing in a 2-unit in Logan Square. 42:00 Essex 312 vs Essex Realty Group. 48:50 Gotchas when buying a 2-4 unit building! 52:10 Neighborhoods that Niko is bullish on! 60:20 5 Year Outlook on Chicago. 62:24 What is your competitive advantage? 63:11 One piece of advice for new investors. 63:27 What do you do for fun? 63:39 Good book, podcast, or self development activity that you would recommend? 64:04 Local Network Recommendation? 64:57 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:07:08

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Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants

12/2/2025
How do I protect myself against potential tenant screening scams? ============= Connect 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 give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Link: Forewarn.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:12:02

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Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats

11/27/2025
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 this episode, Lawrence emphasizes the importance of deeply understanding your market and getting in the game to achieve success! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Lawrence Dunning, Fulton Grace Realty Link: SUCI Ep 118 - Lawrence Dunning Link: Enter The Lionheart (Lawrence's Podcast) Link: The One Thing (Book Recommendation) Link: Vevor Adjustable Handrails Guest Questions: 03:01 Housing Provider Tip - Leverage adjustable handrails for an affordable solution to meet compliance requirements! 04:58 Intro to our guest, Lawrence Dunning! 12:27 Lawrence's business and areas of focus! 16:40 Real estate agent's value to developers. 26:33 Setting the top comparables in a neighborhood. 35:02 Lawrence's top emerging neighborhoods! 45:46 Outlook on Chicago's south side. 52:01 What is your competitive advantage? 53:00 One piece of advice for new investors. 53:47 What do you do for fun? 54:54 Good book, podcast, or self development activity that you would recommend? 56:43 Local Network Recommendation? 57:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:59:11

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Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows

11/20/2025
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 through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Mark Ainley of GC Realty & Development Link: Mark's Instagram Link: The Science of Scaling (Book Recommendation) Link: It's How We Play The Game (Book Recommendation) Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements! 04:55 Intro to our guest, Mark Ainley! 05:48 The history of village requirements for rentals. 09:17 Considerations when investing in Schaumburg. 17:27 Insights on permits and associated fees. 21:38 Navigating point of sale inspections in different villages. 31:46 What to know about tax transfer stamps! 35:56 Overview on rental licenses, village inspections, STR licenses, and more! 39:51 Book recommendations from Mark! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:42:41

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Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev

11/18/2025
When do I have to have my cost segregation done to ensure it is good for my 2025 taxes? ============= Connect 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 give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Link: Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:15:46

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Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons

11/13/2025
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 top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to success! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Luke Helliker Link: Luke Helliker - DocuSign | LinkedIn Link: EUBA Link: SUCI Ep 345 - Joey Turano Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon Link: SUCI Ep 389 - Sebastian Mysliwiec Link: Rich Dad Poor Dad (Book Recommendation) Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 05:03 Intro to our guest, Luke Helliker! 13:19 Luke's first deal: a 2-unit house hack! 20:18 How to leverage the ADU process. 27:20 Funding an ADU project. 41:09 Navigating investing with your significant other. 43:15 Acquiring a 4-unit building in a competitive market! 58:47 Lessons learned on the 4-unit acquisition. 65:30 Luke's next investment targets. 66:19 What is your competitive advantage? 67:15 One piece of advice for new investors. 67:59 What do you do for fun? 69:19 Good book, podcast, or self development activity that you would recommend? 70:01 Local Network Recommendation? 70:30 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:13:42

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Episode 411: Shawn Good Creates Opportunity with Off Market Deals

11/6/2025
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 Collective Genius helped him take his law practice and direct to seller marketing to the next level. He closes with his 5-year plan and hilarious real estate horror stories! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Shawn Good, Good Law Group Link: SUCI Ep 292 - Dorian Bezanis Link: The Collective Genius Podcast Link: The Charisma Myth (Book Recommendation) Guest Questions: 02:06 Housing Provider Tip - Ensure to have a lease on a departing residence when required for another loan! 04:03 Intro to our guest, Shawn Good! 08:25 Transitioning to an 8-unit building after a condo purchase. 13:38 House hacking and starting a law practice! 21:23 Simple partnership structures. 26:28 Generating off-market deal flow! 36:36 Shawn's 5 year plan. 46:44 Horror stories! 51:37 What is your competitive advantage? 52:18 One piece of advice for new investors. 53:27 What do you do for fun? 53:50 Good book, podcast, or self development activity that you would recommend? 55:00 Local Network Recommendation? 56:54 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:59:41

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Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross

11/4/2025
What the different ways I can adjust my offer to make it more attractive? ============= Connect 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Link: SUCI - Resources ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:18:35

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Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman

10/30/2025
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 seller marketing and how he's achieved success. He closes things to keep in mind when practicing wholesaling in Illinois to mitigate your risk! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Eli Goodman, Illinois Real Estate Buyers Link: Eli's Instagram Link: Eli's Meet Up Link: Never Split the Difference (Book Recommendation) Link: Dan Clarton (Title Services Referral) Guest Questions: 01:42 Housing Provider Tip - Leverage a HELOC on your primary residence for emergencies and to continue scaling! 03:37 Intro to our guest, Eli Goodman! 07:00 Getting a wholesaling business off the ground. 11:42 How to communicate directly with sellers! 17:18 Tactical tips on direct to seller marketing. 25:08 Building a list of cash buyers. 34:33 Outlook on Eli's wholesaling business. 37:07 Challenges of wholesaling in Illinois. 44:19 What is your competitive advantage? 44:45 One piece of advice for new investors. 45:00 What do you do for fun? 45:12 Good book, podcast, or self development activity that you would recommend? 45:29 Local Network Recommendation? 46:05 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:48:27

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Episode 408: Chicago Suburb Land Development with Jim Paul

10/23/2025
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 finance these projects. Throughout the episode, Jim repeats the importance of due diligence to mitigate risks and protect yourself and your investors! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Jim Paul, ALPS Group | Call Jim: (815) 469-3800 | Email Jim: jmp@TheALPSGroup.com Link: Lee Iacocca Autobiography Link: Building Industry Association Chicago Guest Questions: 02:21 Housing Provider Tip - Considering replacing older appliances instead of spending on repairs! 03:25 Intro to our guest, Jim Paul! 05:40 Developing a 21-acre property with limited experience! 14:28 How to source land deals. 24:27 Getting creative with land development! 29:02 Financing land development. 34:03 Lessons learned from 20 years of experience. 35:45 The ins and outs of receivership. 52:22 Jim’s plan for the next 5 years! 55:31 What is your competitive advantage? 57:25 One piece of advice for new investors. 58:41 What do you do for fun? 59:00 Good book, podcast, or self development activity that you would recommend? 60:50 Local Network Recommendation? 62:07 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:04:48

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Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago

10/21/2025
What are the differences between R2, R3, R4, and R5 zoning? ============= Connect 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Link: SUCI - Resources ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:20:07

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Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa

10/16/2025
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 on the due diligence process. Moises shares great insights on capital raising and structuring partnerships to be able to take down these large acquisitions. He breaks down how he leveraged a broker relationship to acquire a deal in Fort Wayne, IN well below market value. This episode showcases how building a team and fostering relationships can truly pay dividends in REI! 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 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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Moises Correa, Principal of Proximo Equity Group Link: SUCI Ep 369 - Erik Swanson Link: What It Takes (Book Recommendation) Guest Questions: 02:50 Housing Provider Tip - Understand your leases entirely to avoid legal issues. 04:44 Intro to our guest, Moises Correa! 09:05 Early lessons learned in REI! 14:43 Moises’ second acquisition. 22:03 Jumping into a larger deal in Louisville! 34:02 Capital raising and structuring partnerships! 45:45 Horror stories from Louisville deals. 49:46 Investing in Fort Wayne, IN! 57:48 What is your competitive advantage? 58:18 One piece of advice for new investors. 59:21 What do you do for fun? 59:54 Good book, podcast, or self development activity that you would recommend? 60:09 Local Network Recommendation? 60:28 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:03:08

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Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal

10/9/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= 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 transaction volume. Joe dives deep on the market trends for Chicago’s North Side including prime neighborhoods like Lincoln Park and Lakeview. Joe closes with takeaways from some recent personal transactions and provides an optimistic outlook on the Chicago Real Estate 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: Joe Smazal, Interra Realty Link: Joe Smazal - Interra Realty LLC | LinkedIn Link: Real Estate Chicago Style Podcast Link: SUCI Ep 156 - Joe Smazal Link: SUCI Ep 368 - Joe Smazal (NSBC Live Event) Link: Mark Wilczak (Inspector Referral) Link: Scott Weinstein (Field and Goldberg) Guest Questions 02:38 Housing Provider Tip - Understand rules and regulations around security deposits! 05:00 Intro to our guest, Joe Smazal! 07:10 Joe’s Real Estate Chicago Style Podcast! 15:25 Joe’s path to $1 Billion of Commercial RE sales. 23:11 Chicago market trends in 2025. 31:27 Navigating the Predominance of the Block (606) Ordinance. 49:50 Joe’s 5-year plan. 54:57 The outlook on Chicago! 58:29 What is your competitive advantage? 58:53 One piece of advice for new investors. 59:19 What do you do for fun? 59:51 Good book, podcast, or self development activity that you would recommend? 60:55 Local Network Recommendation? 62:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:05:37

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Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo

10/7/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= What are my lending options for a non-owner occupied investor? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo of Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:11:32

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Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski

10/2/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= 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 gets granular on partnering on a few BRRRR deals and the value he brought to the partnership despite not having much liquidity! He shares insights on closing a house hack deal with a hilarious story about living in a “work in progress” basement apartment! Lantz demonstrates how hard work and bringing value to others is very much the key to succeeding in REI like other areas of life! 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: Lantz Kurzawinksi, GC Realty & Development Link: SUCI Ep 253 - Jeff Nydegger Link: The Obstacle Is the Way (Book Recommendation) Link: Meditations (Book Recommendation) Link: Michael Procaccio (Network Referral) Guest Questions 02:49 Housing Provider Tip - Consider giving renters storage unit options to maximize your units’ appeal. 04:39 Intro to our guest, Lantz Kurzawinski! 12:56 Starting off as a leasing agent. 18:38 Lantz’s first deal! 23:06 Cranking through another BRRRR project and structuring partnerships. 28:00 House hacking in Jefferson Park! 40:30 Taking down deals in Itasca and Downers Grove. 46:51 What is your competitive advantage? 47:20 One piece of advice for new investors. 48:22 What do you do for fun? 48:28 Good book, podcast, or self development activity that you would recommend? 49:10 Local Network Recommendation? 49:41 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:50:22

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Episode 402: Looking At Chicago Investing Differently with Jason Wagner

9/25/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= 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 Heights and powerful advice for new, aspiring investors! 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: Jason Wagner, Greystone Realty Link: SUCI Ep 224 - Jason Wagner Link: Real Life Investing with Jason & Rachel Wagner (Podcast) Link: Wagner Report Link: The 5 Types of Wealth (Book Recommendation) Link: SUCI Ep 244 - Ryan Bakke Guest Questions 02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers! 04:52 Intro to our guest, Jason Wagner! 10:53 Emerging neighborhoods and creative strategies for cash flow! 28:42 Ins and outs of assumable loans. 36:06 Insights on VA loan assumptions. 38:03 The background on Greystone Realty. 42:56 Housing market takeaways from the Wagner Report! 45:58 Opportunities in Arlington Heights. 50:26 Best of advice for aspiring real estate investors. 52:42 What is your competitive advantage? 53:07 One piece of advice for new investors. 53:20 What do you do for fun? 54:28 Good book, podcast, or self development activity that you would recommend? 56:19 Local Network Recommendation? 57:11 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:01:02

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Episode 401: Interest Rates Are Coming Down According to Chris Puelo

9/23/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Chris Puleo lays out tangible reasons why he feels interest rates will be coming down in the upcoming future. ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo of Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:00:13:21

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Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio

9/18/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= 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 with explaining the importance of building a great reputation to set yourself up for success in this relationship-based business! 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 Rocio, ROC Advisory Group Link: Kevin Rocio's Instagram Link: Crain's Chicago Business Link: SUCI Ep 296 - Moses Hall Link: Mike Levin (Network Referral) Guest Questions 04:09 Housing Provider Tip - Let insurance representatives know about property improvements to reduce your premium! 05:50 Intro to our guest, Kevin Rocio! 14:45 Transitioning out of mortgage lending after 17 years. 20:46 Starting in real estate brokerage in 2009. 33:16 Utilizing GRM for valuations. 34:51 Kevin’s business through and post COVID. 48:31 How to find a mentor! 52:32 Importance of marketing and building a reputation. 55:05 What is your competitive advantage? 55:32 One piece of advice for new investors. 56:08 What do you do for fun? 56:50 Good book, podcast, or self development activity that you would recommend? 58:18 Local Network Recommendation? 59:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:01:24

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Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White

9/11/2025
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: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= 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 with valuable insights on structuring partnerships and building a track record to attract investors! 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: Micah White, Brick by Brick Blueprint Link: Real Estate with Micah Link: Micah's Instagram Link: A Long Way Gone (Book Recommendation) Link: Shoe Dog (Book Recommendation) Link: Block Club Chicago Guest Questions 02:22 Housing Provider Tip - Remove window AC units to improve heat efficiency this winter! 03:45 Intro to our guest, Micah White! 14:31 Micah’s start in REI! 22:12 Due diligence on your first deal. 26:58 Bumping rents and stabilizing a building. 31:28 The DIY wax ring story! 37:27 Micah’s North Lawndale deal. 44:38 Structuring partnerships with investors. 53:20 Reputation building to attract investors. 57:22 What is your competitive advantage? 58:01 One piece of advice for new investors. 58:35 What do you do for fun? 59:45 Good book, podcast, or self development activity that you would recommend? 61:56 Local Network Recommendation? 62:17 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Duration:01:05:07