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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Strona podcastu
Ostatni odcinek
1 paź 2026
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Odcinki
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...
Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma 10.04.2025 54:43
Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals! Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into "creative" deals including one deal where he was able to close on a property minutes before it would have been foreclosed on. Jeffrey...
Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon 03.04.2025 47:24
Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio! Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that involved getting caught doing construction without a pe...
Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman 01.04.2025 13:34
How does credit effect DSCR loans? ============= 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, Renovo Financial Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans Link: B...
Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren 27.03.2025 43:44
John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties' plan for growth in the western suburbs. John dives into starting a property management company along with building and remaining loyal to a team to support his portfolio....
Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry 20.03.2025 44:18
Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations. Scott starts by sharing his experience working at JPMorgan's Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a case study of an adaptive reuse project and gets gr...
Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance 18.03.2025 14:32
What actionable steps do I need to take for the Northwest Side Preservation Ordinance? ============= 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: Brie Schmidt, Second City Real Estate Link: Northwest Side P...
Episode 360: Don't Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney 13.03.2025 45:57
David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo provides real life examples of how a land trust can...
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