Episodios

  • Episode 396: House Hacking Your Way to Lasting Wealth with Paul de Luca
    Sep 4 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

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    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

    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    53 m
  • 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?
    Sep 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

    =============

    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

    Guest: Josh Steigelmann, State Farm Insurance

    Link: Investor Stories Featuring Sean Morrissey

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    21 m
  • Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
    Aug 28 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

    =============

    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

    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    1 h y 9 m
  • Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew
    Aug 21 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

    =============

    Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago’s north side!

    Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He talks about the importance of knowing your market to accurately project rents and pro-formas. Max gets granular on leasing including tips for screening out fraudulent applicants and best marketing practices. Throughout the episode, Max emphasizes the importance of having great relationships with tenants and being an expert in your geographical area of focus as keys 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

    Guests: Max Motew, Mo2 Properties

    Link: Max's LinkedIn

    Link: SUCI Ep 372 - Kevin Schnell

    Link: Neighborhood Building Owner's Alliance - Chicago

    Guest Questions

    02:05 Housing Provider Tip - Take action and jump into real estate!

    03:23 Intro to our guest, Max Motew!

    07:10 Considerations on landmarked buildings.

    14:04 Making deals “pencil” in today’s market.

    23:36 Projecting rents and pro-formas!

    32:55 Optimizing lease renewals.

    43:15 Common leasing mistakes to avoid!

    50:08 Screening best practices.

    55:57 Up and coming Chicago neighborhoods!

    61:18 What is your competitive advantage?

    62:25 One piece of advice for new investors.

    62:48 What do you do for fun?

    63:30 Good book, podcast, or self development activity that you would recommend?

    64:09 Local Network Recommendation?

    64:37 How can the listeners learn more about you and provide value to you?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    1 h y 7 m
  • Episode 394: The Legal Nuances of Different Real Estate Partnership Structures
    Aug 19 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

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    What do investors need to consider from a legal perspective when setting up new partnerships?

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Bibek Das, Das Law

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    13 m
  • Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy
    Aug 14 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 ============= DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits! DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He breaks down the rent-by-the-room strategy as a tool to maximize ROI. DuBois dives deep on VA loans, tax exemptions, and various other powerful real estate tools available to veterans! From leveraging AI for deal searching to veteran resources, this show is full of invaluable insights that you won’t want to miss! 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 Guests: DuBois Toy, Trading Technologies Link: DuBois' Facebook Link: Cook County Veterans with Disabilities Exemption Link: Cook County Returning Veterans Exemption Link: Andrew Dorazio's Veterans Real Estate Meetup Link: Academy of Ideas (YouTube Channel) Link: Meditations (Book Recommendation) Guest Questions 02:17 Housing Provider Tip - Understand rental license and inspection requirements in the suburbs! 04:00 Intro to our guest, DuBois Toy! 08:31 The future of tech in real estate! 15:49 DuBois’ background and start in real estate. 24:27 House hacking and dealing with an eviction in Oak Park! 29:27 Leveraging rent by the room strategy. 35:58 Educating veterans on VA loan benefits! 41:26 Revealing DuBois’ growth strategy! 49:09 DuBois’ bullish outlook on Chicago! 54:23 What is your competitive advantage? 55:03 One piece of advice for new investors. 55:41 What do you do for fun? 56:14 Good book, podcast, or self development activity that you would recommend? 57:20 Local Network Recommendation? 58:38 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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    1 h y 1 m
  • Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars
    Aug 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

    =============

    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

    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    51 m
  • Episode 391: Do You Have a Business Continuation Plan?
    Aug 5 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

    =============

    Josh Steigelmann explains the importance of a business continuation plan and provides step-by-step guidance on how investors can set-up a business continuation plan

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Josh Steigelmann, State Farm Insurance

    Link: Straight Up Chicago Investor Investor Stories Featuring Sean Morrissey

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.

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    9 m