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...
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Straight Up Chicago Investor
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Latest episode
Jul 9, 2026
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Episodes
Episode 391: Do You Have a Business Continuation Plan? 05.08.2025 9:08
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 ============= C onnect 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...
Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims 31.07.2025 58:58
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 propertie...
Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec 24.07.2025 1:02:15
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 ============= Sebas...
Episode 388: NBOA 2025 Summer Soiree Update 22.07.2025 14:38
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...
Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz 17.07.2025 48:43
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...
Episode 386: How to Invest in DuPage County with Katie and Rob Hayes 10.07.2025 1:06:44
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...
Episode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter 08.07.2025 16:24
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...
Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton 03.07.2025 54:10
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...
Episode 383: From Chemist to Chicago's "Bow Tie" Attorney w/Mahmoud Faisal Elkhatib 26.06.2025 1:01:32
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 ============= Mahmo...
Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago 24.06.2025 16:47
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...
Episode 381: How Chicago's Powerhouse Lender Renovo Financial Was Built with Kevin Werner 19.06.2025 1:11:05
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...
Episode 380: Innovation in Modular Housing With Rory Rubin 12.06.2025 33:25
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 ============= Rory...
Episode 379: Preparing Your Property To Add an ADU 10.06.2025 12:25
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 ============= How c...
Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds 05.06.2025 56:57
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 ============= Wonde...
Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker 29.05.2025 55:27
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 ============= Danie...
Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property 27.05.2025 10:20
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 ============= How C...
Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez 22.05.2025 52:05
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 ============= Real...
Episode 374: Taking On Opportunity In Chicago's Toughest Neighborhoods with Corey Oliver 15.05.2025 1:06:33
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 ============= Corey...
Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties 13.05.2025 10:09
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 ============= How c...
Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell 08.05.2025 54:20
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...
Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan 01.05.2025 54:20
Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit property in McHenry. Michael gets granular on how provi...
Episode 370: How The Current 2025 Lending Market Differs From Previous Year 29.04.2025 12:00
What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial Link: Workman Lending Team...
Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson 24.04.2025 54:49
Erik Swanson, owner of Fernweh Property Group, explains how he's developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple real estate deals including a FHA 203k loan and an...
Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event) 17.04.2025 40:42
Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC's Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate market! If you enjoy today's episode, please leave us a review and share with s...
Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg 15.04.2025 6:41
How do I incentivize and optimize renewals? ============= If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! C onnect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jeff Weinberg, Drexel Properties Link: Jeff Weinberg Shares Property Management Expertise on the Straight...
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