Straight Up Chicago Investor

Straight Up Chicago Investor
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Nov 27, 2025 • 59min

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

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.
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Nov 20, 2025 • 43min

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

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.
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Nov 18, 2025 • 16min

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

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.
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Nov 13, 2025 • 1h 14min

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

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.
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Nov 6, 2025 • 60min

Episode 411: Shawn Good Creates Opportunity with Off Market Deals

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.
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Nov 4, 2025 • 19min

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

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.
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Oct 30, 2025 • 48min

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

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.
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Oct 23, 2025 • 1h 5min

Episode 408: Chicago Suburb Land Development with Jim Paul

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.
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Oct 21, 2025 • 20min

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

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.
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Oct 16, 2025 • 1h 3min

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

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.

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