

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 and not worked in Chicago, you are in the right place.
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.
Episodes
Mentioned books

Sep 11, 2025 • 1h 5min
Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White
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 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: 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.

Sep 4, 2025 • 53min
Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca
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 troublesome tenants and provides his take on emerging neighborhoods where he's investing! Throughout the episode, Paul demonstrates how focus and taking action have been keys to his investing 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: Paul de Luca, eXp Realty - The Axon Group Link: Paul's Instagram Link: Paul's BiggerPockets Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon Link: 5 Types of Wealth (Book Recommendation) Link: On The Market (Podcast Recommendation) Link: Adam Gurney (Attorney Referral) Guest Questions 03:25 Housing Provider Tip - Consider the ROI on central HVAC! 05:08 Intro to our guest, Paul de Luca! 10:52 Reflecting on Paul's first house hack. 13:45 Getting into house hack #2! 21:20 Getting started as a new real estate agent. 25:32 Valuing non-conforming units. 31:33 Handling problem tenants. 36:18 Neighborhood guide for investors! 42:35 Paul's 5 year outlook! 48:48 What is your competitive advantage? 49:23 One piece of advice for new investors. 49:50 What do you do for fun? 50:00 Good book, podcast, or self development activity that you would recommend? 50:31 Local Network Recommendation? 50:55 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.

Sep 2, 2025 • 21min
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?
What are the "do's" and "don'ts" when filing an insurance claim? ============= 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: Josh Steigelmann, State Farm Insurance Link: Investor Stories Featuring Sean Morrissey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

Aug 28, 2025 • 1h 9min
Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
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 the 101 on various financing options and repositioning strategies for self storage investments. He closes with a motivating 5-year outlook including a detailed plan to reach financial independence! 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: Fernando Angelucci, Self Storage Syndicated Equities Link: Fernando's Instagram Link: SUCI Ep 86 - Fernando Angelucci Link: Vagabonding (Book Recommendation) Link: SUCI Ep 392 - Cost Seg Kev Guest Questions 01:49 Housing Provider Tip - Be sure to perform maintenance on AC units after a long summer! 03:25 Intro to our guest, Fernando Angelucci! 06:41 Growing a portfolio in a low inventory market! 12:10 Feasibility studies on self storage projects. 16:44 Building a self storage investment team! 21:56 Financing self storage deals. 37:33 Repositioning a self storage investment. 47:57 Obtaining special use permits. 52:01 Ideal self storage projects! 55:23 Fernando's 5-year outlook. 60:26 What is your competitive advantage? 62:55 One piece of advice for new investors. 63:32 What do you do for fun? 64:14 Good book, podcast, or self development activity that you would recommend? 64:48 Local Network Recommendation? 65:53 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.

Aug 21, 2025 • 1h 7min
Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew
Max Motew, Director of Leasing at Mo2 Properties, shares his expertise on acquiring and renovating small multifamily properties in Chicago. He dives into essential considerations for renovating landmarked properties and the need for market knowledge to project rents accurately. Tips on screening tenants reveal strategies to combat fraud, while effective marketing practices enhance leasing success. Max emphasizes the value of strong tenant relationships and geographic expertise, highlighting these as key ingredients for thriving in the competitive Chicago property market.

Aug 19, 2025 • 13min
Episode 394: The Legal Nuances of Different Real Estate Partnership Structures
In this discussion, Bibek Das, an Attorney at Das Law who specializes in real estate law, shares invaluable insights on the legal intricacies of real estate partnerships. He discusses the critical differences between partnership agreements and LLCs, emphasizing the need for clear operating agreements to mitigate risks. Common pitfalls in partnerships, such as vague roles and the importance of transparent decision-making, are also covered. Bibek further highlights the necessity of regularly updating legal documents to stay compliant and protect investments.

Aug 14, 2025 • 1h 1min
Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy
DuBois Toy, a real estate investor and veteran, shares his journey from house hacking to mastering rental strategies. He emphasizes the benefits of VA loans and tax exemptions available for veterans, making real estate investment more accessible. DuBois also discusses leveraging AI to streamline property searches and tenant screening processes. His insights into maximize cash flow through room rentals and the importance of community networking provide valuable tools for anyone looking to navigate the Chicago real estate scene.

Aug 7, 2025 • 51min
Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars
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 touches on frequently asked questions on cost segregation studies and closes with how he built his business and reputation! 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 ============= Guests: Kevin Cawley, CSSI Services Link: CSSI Cost Segregation Calculator Link: SUCI Ep 59 - Cost Seg Kev Link: James Mahon (CPA Referral) Link: At Your Command (Book Recommendation) Guest Questions 02:46 Housing Provider Tip - Go above and beyond to acknowledge tenants after management mistakes. 05:00 Intro to our guest, Cost Seg Kev! 05:43 The 101 on Cost Segregation. 11:37 The benefits of real estate professional status! 25:42 Recent changes to depreciation rules. 32:15 Technical side of cost segregation! 34:23 Cost Seg on smaller properties. 43:43 What is your competitive advantage? 44:42 One piece of advice for new investors. 46:00 What do you do for fun? 46:37 Good book, podcast, or self development activity that you would recommend? 47:52 Local Network Recommendation? 48:55 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.

Aug 5, 2025 • 9min
Episode 391: Do You Have a Business Continuation Plan?
Discover the critical need for a business continuation plan tailored for real estate investors. Learn practical steps to protect assets and prepare for unexpected events, ensuring a smooth transition for beneficiaries. The discussion also highlights the surprising gap in personal life insurance coverage and its significance for future financial stability. Plus, enjoy some fun trivia about Chicago's vibrant summer festivals, blending education with entertainment!

Jul 31, 2025 • 59min
Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims
Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55 years! Mitch starts by explaining the services rendered by insurance adjusters. He breaks down how investors can set themselves up for success with insurance claims and provides tactical steps for handling disastrous situations at properties. Mitch dives deep on insurance coverages, how investors can best protect themselves, and shares some wild insurance stories! This show is full of valuable insurance insights that you will want to put into practice! 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 ============= Guests: Mitch Schoeneman, A. Schoeneman & Co | Email Mitch Link: Jimmy Sarnoff (Tax Appeal Attorney Referral) Guest Questions 03:14 Housing Provider Tip - Home insurance considerations to improve coverage and pricing! 04:56 Intro to our guest, Mitch Schoeonemen! 08:33 The value of insurance adjusters. 15:57 How investors can prepare for successful insurance claims. 21:17 Properly handling emergency situations at properties! 37:15 General timelines for insurance payouts. 45:00 Wild insurance stories! 53:39 What is your competitive advantage? 54:01 One piece of advice for new investors. 54:08 What do you do for fun? 54:59 Good book, podcast, or self development activity that you would recommend? 55:32 Local Network Recommendation? 55:53 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.


