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Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy

EPISODE · Aug 14, 2025 · 1H 1M

Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy

from Straight Up Chicago Investor · host Mark Ainley and Tom Shallcross

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: [email protected] Properties for Sale on the North Side?  We want to buy them. Email: [email protected] 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: 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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Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy

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