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Straight Up Chicago Investor

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Chicago real estate, straight from the field.

The gist

Straight Up Chicago Investor covers the ground-level details of buying, managing, financing, and improving property around Chicago. Tom and Mark mix shop talk, guest stories, and quick owner tips with a direct, informal rhythm.

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About Straight Up Chicago Investor

Straight Up Chicago Investor is a Chicago real estate investing show with a strong practical bias. It is less concerned with abstract market chatter than with the details that can make or break a property decision. A 2-4 unit appraisal becomes a conversation about one-mile comp radius, school districts, transit access, and how different six blocks can feel in the same city. A tax strategy episode turns into a reminder that scale often comes from setting aggressive goals and solving the next constraint. The show moves fast. Tom and Mark bring a casual, sometimes teasing rhythm, then shift into practical questions for investors, builders, property managers, and other dealmakers. Recurring tips cover the everyday parts of ownership, including water heaters, Chicago hard water, cold weather, condo leak risk, and proactive replacement decisions. Bigger episodes stretch into adaptive reuse, ground-up development, and the discipline of making hundreds or thousands of micro decisions on a project. Financing gets the same concrete treatment. Assumable FHA and VA loans, seller financing, master lease agreements, and construction loan positioning are discussed through use cases instead of slogans. The local frame matters. Cook County eviction process issues, Chicago building efficiency, neighborhood knowledge, and industry networking all show up as practical realities. The conversations also return to mindset, but usually in service of action: asking questions, finding the right team, listening better, and moving before every answer is known. Guests such as Ryan Bakke, Adam Friedberg, Michael Scanlon, Josh Bandoch, Joe Konopacki, Fernando Angelucci, and Zeke McDonald-Lewis bring different angles on investing and ownership. The show can be blunt, but its purpose is useful clarity. It is best for listeners who want to hear how people in Chicago real estate talk when they are working through the real constraints of deals, buildings, tenants, capital, and operations.

Made for: For Chicago-area real estate investors, housing providers, property managers, and buyers who want practical deal and operations context. It also fits investors outside Chicago who want concrete examples from a dense, neighborhood-sensitive market.

What sets it apart: The show pairs local Chicago specificity with detailed practical talk, from appraisals and assumable loans to boilers, insulation, and eviction process concerns. Its loose host banter keeps the pace human without sanding down the technical detail.

In their own words

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.

Chicago neighborhood investing2-4 unit appraisalsproperty management tipstax strategy and ROIadaptive reuse and developmentassumable FHA and VA loansenergy efficiency in buildingsself-storage deal structures

Talks about

Business & FinanceReal EstateReal Estate Investing

Podcasts like Straight Up Chicago Investor

Episodes

  1. 1

    Chicago Suburb Land Development with Jim Paul

    ·1h 5m
  2. 2

    Chicago Veterans' Guide to Real Estate Success with DuBois Toy

    ·1h 1m
  3. 3

    Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars

    ·51m
  4. 4

    Leveraging Tax Strategy to Boost ROI with Ryan Bakke

    ·58m
  5. 5

    Adaptive Reuse & Ground Up Development with Adam Friedberg

    ·1h 3m
  6. 6

    How To Identify and Execute on Assumable Loans with Michael Scanlon

    ·14m
  7. 7

    Chicago's Josh Bandoch Using Neuroscience to Win Negotiations

    ·44m
  8. 8

    Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati

    ·1h
  9. 9

    The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm

    ·19m
  10. 10

    Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik

    ·54m
  11. 11

    Energy Efficiency in Chicago Real Estate with Joe Konopacki

    ·1h 18m
  12. 12

    Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel

    ·11m
  13. 13

    36th Ward: Future of Chicago with Alderman Gil Villegas

    ·1h
  14. 14

    Interesting Lease Renewal Statistics and Strategies with Mark Ainley

    ·14m
  15. 15

    Strategic Chicago House Hacking with Zach Posey

    ·50m
  16. 16

    What You Need To Know About Real Estate Professional Status with Mike Procaccio

    ·18m
  17. 17

    From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer

    ·51m
  18. 18

    Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs

    ·1h 9m
  19. 19

    Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley

    ·14m
  20. 20

    2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon

    ·1h 14m
  21. 21

    Reshaping Suburban Woodstock with Jessica Erickson

    ·49m
  22. 22

    Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options

    ·17m
  23. 23

    Chicago Foreclosure Market with Top REO Agent Ryan Smith

    ·55m
  24. 24

    Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm

    ·59m
  25. 25

    Mark Ainley Shares Why He's Excited for Chicago's 2026 Market

    ·9m
  26. 26

    Alec Greenberg Scales to Chicago Multifamily from Day 1

    ·58m
  27. 27

    The Chicago Permitting Process with Tom Shallcross

    ·46m
  28. 28

    What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley

    ·13m
  29. 29

    Mark Ainley Explains Three Red Flags When Screening Tenants

    ·12m
  30. 30

    Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats

    ·59m
  31. 31

    Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows

    ·43m
  32. 32

    Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev

    ·16m
  33. 33

    Luke Helliker Leverages the ADU Process & Learns Many Lessons

    ·1h 14m
  34. 34

    Shawn Good Creates Opportunity with Off Market Deals

    ·1h
  35. 35

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

    ·19m
  36. 36

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

    ·48m
  37. 37

    The Legal Nuances of Different Real Estate Partnership Structures

    ·13m
  38. 38

    How to Take Advantage of the Different Zoning Labels in Chicago

    ·20m
  39. 39

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

    ·1h 3m
  40. 40

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

    ·1h 6m
  41. 41

    Lending Options For Non-Owner Occupied Investors With Chris Puleo

    ·12m
  42. 42

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

    ·50m
  43. 43

    Looking At Chicago Investing Differently with Jason Wagner

    ·1h 1m
  44. 44

    Interest Rates Are Coming Down According to Chris Puleo

    ·13m
  45. 45

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

    ·1h 1m
  46. 46

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

    ·1h 5m
  47. 47

    House Hacking Your Way to Lasting Wealth with Paul de Luca

    ·53m
  48. 48

    When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property?

    ·21m
  49. 49

    Chicago Property Management and Leasing Best Practices with Max Motew

    ·1h 7m
  50. 50

    Do You Have a Business Continuation Plan?

    ·9m
  51. 51

    What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims

    ·59m
  52. 52

    Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec

    ·1h 2m
  53. 53

    NBOA 2025 Summer Soiree Update

    ·15m
  54. 54

    What is a Demand Letter and How to Handle Receipt of a Demand Letter

    ·16m
  55. 55

    From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton

    ·54m
  56. 56

    From Chemist to Chicago's "Bow Tie" Attorney w/Mahmoud Faisal Elkhatib

    ·1h 2m
  57. 57

    Preparing Your Property To Add an ADU

    ·17m
  58. 58

    How Chicago's Powerhouse Lender Renovo Financial Was Built with Kevin Werner

    ·1h 11m
  59. 59

    Innovation in Modular Housing With Rory Rubin

    ·33m
  60. 60

    Preparing Your Property To Add an ADU

    ·12m
  61. 61

    How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds

    ·57m
  62. 62

    This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker

    ·55m
  63. 63

    Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property

    ·10m
  64. 64

    Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez

    ·52m
  65. 65

    Taking On Opportunity In Chicago's Toughest Neighborhoods with Corey Oliver

    ·1h 7m
  66. 66

    A New Option to Fund Renovations For Chicago 2-4 Properties

    ·10m
  67. 67

    Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell

    ·54m
  68. 68

    How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan

    ·54m
  69. 69

    How The Current 2025 Lending Market Differs From Previous Year

    ·12m
  70. 70

    This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson

    ·55m
  71. 71

    Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)

    ·41m
  72. 72

    How to Get Out In Front of Renewals With Jeff Weinberg

    ·7m
  73. 73

    From Creative Financing to Six-Figure Commission Checks with Jeffrey Ma

    ·55m
  74. 74

    Building a $20 Million Portfolio Using BRRRR with Wyatt Simon

    ·47m
  75. 75

    Small Credit Items That Lead to Large Financial Impacts with Eric Workman

    ·14m
  76. 76

    168 Western Suburb units In Less Than 10 Years with John Warren

    ·44m
  77. 77

    Free Money to Develop Affordable Housing? Learn How with Scott Henry

    ·44m
  78. 78

    What To Do Regarding the Northwest Side Preservation Ordinance

    ·15m
  79. 79

    2025 Cook County Evictions with Tom Raleigh

    ·1h 1m
  80. 80

    Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio

    ·12m
  81. 81

    Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network

    ·1h 24m
  82. 82

    The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro

    ·1h 11m
  83. 83

    How To Optimize Tax Deductions as a Househacker

    ·18m
  84. 84

    2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon

    ·1h 14m
  85. 85

    From Near Death Experience, to Disciplined Financial Freedom with Mike Bednarz

    ·52m
  86. 86

    Current Issues The NBOA is Fighting with Mike Glasser

    ·12m
  87. 87

    Obstacles Affordable Housing Developers Face in Illinois with Richard Koenig

    ·56m
  88. 88

    Reality TV to Realty… Everything Chicago Investor Mike Tenerelli Has Accomplished

    ·47m
  89. 89

    Do I Need To Give My Tenant a 30 Day Notice?

    ·8m
  90. 90

    Sam Patterson Is All In On This Western Suburb W/Property Taxes Going Down

    ·1h 5m
  91. 91

    Solving Housing Affordability With Josh Bandoch

    ·54m
  92. 92

    Three New Laws Illinois Investors Need to be Aware of in 2025

    ·13m
  93. 93

    Multiple Logan Square 3-Flats With Less Than $10k Down…Hear How with Joey Turano

    ·53m
  94. 94

    Buying, Building, and Adding Value in Self Storage with Fernando Angelucci

    Fernando Angelucci, head of SSSE, returns to discuss his self-storage investing journey, growing from $50M to $230M under management across 54 facilities in 24 states.

    ·1h 9m·5 clips
  95. 95

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

    Zeke McDonald-Lewis reviews the Cook County eviction process for Chicago landlords, discussing how eviction records may not follow tenants to future rentals.

    ·1h 1m
  96. 96

    Chicago Building Code Violations with Zack Limbaugh

    Real estate investors discuss the opportunities and strategies for dealing with Chicago building code violations, emphasizing the importance of having the right expert to negotiate solutions.

    ·55m
  97. 97

    How to Invest in DuPage County with Katie and Rob Hayes

    Katie and Rob Hayes discuss traditional real estate investing in DuPage County, emphasizing simplicity and letting time work its magic.

    ·1h 7m
  98. 98

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

    Niko Apostal shares lessons from 20 years and 800 doors of multifamily real estate investing in Chicago.

    ·1h 7m
  99. 99

    This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz

    Hosts Tom and Mark discuss the importance of volume and surrounding yourself with successful people in real estate investing, using a young investor's story as inspiration.

    ·49m
  100. 100

    Don't Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney

    Chicago Title LandTrust experts David Lanciotti and Del Denney explain how land trusts provide privacy, asset protection, and estate planning benefits for real estate investors.

    ·46m·4 clips
  101. 101

    Understanding 2-4 Unit Appraisals

    Tom Shellcross and Mark Ainley discuss what appraisers look for when valuing 2-4 unit properties, including location factors like school districts and public transportation within a one-mile radius.

    Apr 14, 2026·20m
  102. 102

    Leveraging Tax Strategy to Boost ROI with Ryan Bakke

    Real estate investors discuss scaling strategies and a practical tip on hot water heater replacement in Chicago.

    Apr 9, 2026·58m
  103. 103

    Adaptive Reuse & Ground Up Development with Adam Friedberg

    Adam Friedberg discusses transitioning from general contractor to developer, emphasizing asking questions, making micro decisions, and building the right team.

    Apr 2, 2026·1h 3m
  104. 104

    How To Identify and Execute on Assumable Loans with Michael Scanlon

    Michael Scanlon explains which loan products are assumable, focusing on FHA and VA loans, and how investors can assume low-interest mortgages.

    Mar 31, 2026·14m
  105. 105

    Chicago's Josh Bandoch Using Neuroscience to Win Negotiations

    Josh Bandoch discusses using neuroscience to win negotiations, emphasizing persuasion over being right.

    Mar 26, 2026·44m·2 clips
  106. 106

    Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati

    Mar 19, 2026·1h
  107. 107

    The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm

    Jonathan Clem says renovation-loan budgets are hypotheses, while contingencies usually cover only 10% to 20%.

    Mar 17, 2026·19m·1 clip
  108. 108

    Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik

    Mar 12, 2026·54m
  109. 109

    Energy Efficiency in Chicago Real Estate with Joe Konopacki

    Hidden gem

    Joe Konopacki of Insight Property Services explains how air leakage, insulation, moisture, and heating systems interact in Chicago-area multifamily buildings.

    Mar 5, 2026·1h 18m·5 clips
  110. 110

    Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel

    Mar 3, 2026·11m
  111. 111

    36th Ward: Future of Chicago with Alderman Gil Villegas

    Gil Villegas compares Chicago's permit process with tracking a cheeseburger through DoorDash.

    Feb 26, 2026·1h·2 clips
  112. 112

    Interesting Lease Renewal Statistics and Strategies with Mark Ainley

    Hidden gem
    Feb 24, 2026·14m
  113. 113

    Chicago Building Code Violations with Zack Limbaugh

    Hidden gem

    Zach Limbaugh joins Tom and Mark on Straight Up Chicago Investor to explain how Chicago investors should investigate building-code violations before buying.

    Feb 19, 2026·55m·3 clips
  114. 114

    Strategic Chicago House Hacking with Zach Posey

    Feb 12, 2026·50m
  115. 115

    What You Need To Know About Real Estate Professional Status with Mike Procaccio

    Feb 10, 2026·18m
  116. 116

    From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer

    Feb 5, 2026·51m
  117. 117

    Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs

    Jan 29, 2026·1h 9m
  118. 118

    Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley

    Jan 27, 2026·14m
  119. 119

    2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon

    Jan 22, 2026·1h 14m
  120. 120

    Reshaping Suburban Woodstock with Jessica Erickson

    Jan 15, 2026·49m
  121. 121

    Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options

    Jan 13, 2026·17m
  122. 122

    Chicago Foreclosure Market with Top REO Agent Ryan Smith

    Jan 8, 2026·55m
  123. 123

    Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm

    Jan 1, 2026·59m
  124. 124

    Mark Ainley Shares Why He's Excited for Chicago's 2026 Market

    Dec 30, 2025·9m
  125. 125

    Alec Greenberg Scales to Chicago Multifamily from Day 1

    Dec 25, 2025·58m
  126. 126

    The Chicago Permitting Process with Tom Shallcross

    Dec 18, 2025·46m
  127. 127

    What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley

    Dec 16, 2025·13m
  128. 128

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

    Dec 11, 2025·1h 1m
  129. 129

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

    Dec 4, 2025·1h 7m
  130. 130

    Mark Ainley Explains Three Red Flags When Screening Tenants

    Dec 2, 2025·12m
  131. 131

    Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats

    Nov 27, 2025·59m
  132. 132

    Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows

    Nov 20, 2025·43m
  133. 133

    Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev

    Nov 18, 2025·16m
  134. 134

    Luke Helliker Leverages the ADU Process & Learns Many Lessons

    Nov 13, 2025·1h 14m
  135. 135

    Shawn Good Creates Opportunity with Off Market Deals

    Nov 6, 2025·1h
  136. 136

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

    Nov 4, 2025·19m
  137. 137

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

    Oct 30, 2025·48m
  138. 138

    Chicago Suburb Land Development with Jim Paul

    Oct 23, 2025·1h 5m
  139. 139

    How to Take Advantage of the Different Zoning Labels in Chicago

    Oct 21, 2025·20m
  140. 140

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

    Oct 16, 2025·1h 3m
  141. 141

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

    Oct 9, 2025·1h 6m
  142. 142

    Lending Options For Non-Owner Occupied Investors With Chris Puleo

    Oct 7, 2025·12m
  143. 143

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

    Oct 2, 2025·50m
  144. 144

    Looking At Chicago Investing Differently with Jason Wagner

    Sep 25, 2025·1h 1m
  145. 145

    Interest Rates Are Coming Down According to Chris Puleo

    Sep 23, 2025·13m
  146. 146

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

    Sep 18, 2025·1h 1m
  147. 147

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

    Sep 11, 2025·1h 5m
  148. 148

    House Hacking Your Way to Lasting Wealth with Paul de Luca

    Sep 4, 2025·53m
  149. 149

    When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property?

    Sep 2, 2025·21m
  150. 150

    Buying, Building, and Adding Value in Self Storage with Fernando Angelucci

    Aug 28, 2025·1h 9m