Straight Up Chicago Investor

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.

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.

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!

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.

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 ============= Sebastian Mysliwiec, founder of The Dream Rentals, explains how he's built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits! Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team's growth strategy. 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: Sebastian Mysliwiec, The Dream Rentals Link: The Dream Rentals Instagram Link: Skyscraper Tom's Instagram Link: The 12 Week Year (Book Recommendation) Guest Questions 01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence! 04:25 Intro to our guest, Sebastian Mysliwiec! 08:31 Defining AirBnB arbitrage. 13:28 Underwriting basics of short-term rentals (STRs)! 20:10 Listing platforms for STRs. 26:09 Managing STR seasonality in Chicago to optimize profit. 35:36 STR Marketing Tips! 45:45 AirBnB Horror Story! 47:46 Top STR amenities. 49:23 Mid-Term Rental analysis and expanding to other markets! 55:13 Refinancing STR properties. 56:47 What is your competitive advantage? 57:15 One piece of advice for new investors. 57:42 What do you do for fun? 58:25. Good book, podcast, or self development activity that you would recommend? 58:54 Local Network Recommendation? 59:29 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.

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 is the NBOA Summer Soiree and how can investors benefit from this event? 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: Mike Glasser & Real Estate Nate, NBOA Link: Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 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 ============= Alex Diaz explains how he left his day job as a barber to successfully flip and wholesale real estate for a living at 24 years of age! Alex starts by sharing how he made the jump from being a barber to wholesaling real estate. He explains how he acquired his first property; a househack sourced off-market! Alex provides tactical advice on marketing directly to sellers to create deal flow. He talks about lessons learned from flipping and gets granular on the real estate market in Aurora and the surrounding suburbs. This is another motivating show with an investor thriving at a young age! 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: Alex Diaz, Bluestone Property Solutions Link: Alex Diaz's Instagram Link: SUCI Ep 335 - Aram Ghazaryan Link: The Art of the Deal (Book Recommendation) Guest Questions 03:16 Housing Provider Tip - Maintain and understand misusage of water hose spigots! 05:09 Intro to our guest, Alex Diaz! 10:38 Alex's first house hack sourced off-market! 14:24 Jumping into wholesaling and direct-to-seller marketing. 26:20 Marketing strategy and the 101 on Montgomery, IL. 29:11 Benefits of being around like-minded investors. 35:10 Lessons learned from flipping! 39:24 Alex's geographic areas of focus. 44:06 What is your competitive advantage? 44:31 One piece of advice for new investors. 45:14 What do you do for fun? 45:31 Good book, podcast, or self development activity that you would recommend? 46:04 Local Network Recommendation? 46:23 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.

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 ============= Katie and Rob Hayes are investors and realtors with nearly 2 decades of experience acquiring and managing investment properties! The duo starts by sharing their background including investing in Florida before transitioning to the Chicago Western Suburbs. They share lessons learned from investing in lower cost areas and why they pivoted to higher class assets. Rob and Katie share golden nuggets on marketing to owners for deal flow and on operating short-term rentals. They close out with a positive outlet on Downer's Grove and why investors should be considering it! 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: Katie and Rob Hayes, Platinum Partners Realtors Link: Team Hayes Realtors Facebook Link: Rob's LinkedIn Link: CAREIA Investor's Group Guest Questions 03:03 Housing Provider Tip - Utilize Starbucks gift cards to easily express gratitude towards tenants and vendors! 04:33 Intro to our guests, Katie and Rob Hayes! 09:54 Jumping from Florida to local investments! 14:30 Considerations when investing in lower price point areas. 17:45 Investments leading up to the housing crash. 23:47 Getting a real estate license during the housing crash. 29:05 Creating deal flow in a low inventory market. 34:40 Representing and adding value to buyers in this market. 39:17 Dialing back acquisitions and strategizing for retirement! 44:35 Short-term rentals in Chicago suburbs. 54:40 Advice for couples who invest together! 57:15 What is your competitive advantage? 58:31 One piece of advice for new investors. 59:45 What do you do for fun? 60:34 Good book, podcast, or self development activity that you would recommend? 61:42 Local Network Recommendation? 63:05 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.

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 ============= As an investor, how do I handle receipt of a demand letter? 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: Bibek Das, Das Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 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 ============= Jake Clopton, President of Clopton Capital, has successfully been running his commercial lending business for over 17 years. Jake shares how he grinded early in his career to get off the ground, and emphasizes the value of cold calling. He explains the different types of interest rates and provides the current state of rates. Jake speaks about macro-level economics including the stagflationary environment in today's market. In typical SUCI fashion, he closes out with a bullish outlook on Chicago! 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: Jake Clopton, Clopton Capital Link: Jake Clopton's LinkedIn Link: Jake Clopton's Instagram Link: Never Split the Difference (Book Recommendation) Link: Elevate Energy (Network Referral) Guest Questions 02:07 Housing Provider Tip - Understand how to prioritize emergency work orders. 04:10 Intro to our guest, Jake Clopton! 12:20 Surviving as a lender during the real estate crash. 19:20 Jake's "tipping point" deal! 20:21 The state of interest rates. 28:56 Rates on residential real estate. 34:04 Jake's predictions on rates and the RE market! 41:53 The 101 on Stagflation. 43:50 Jake's bullish remarks on Chicago! 48:05 What is your competitive advantage? 48:32 One piece of advice for new investors. 49:06 What do you do for fun? 49:17 Good book, podcast, or self development activity that you would recommend? 50:06 Local Network Recommendation? 51:40 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.