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Straight Up Chicago Investor

Straight Up Chicago Investor

By: Straight Up Chicago Investor
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About this listen

 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 and not worked in Chicago, you are in the right place.Copyright of Straight Up Chicago Investor 2021. Career Success Economics Personal Finance
Episodes
  • Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton

    Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton
    Jul 3 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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    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!

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    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?

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
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    54 mins
  • Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib

    Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib
    Jun 26 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 ============= Mahmoud Faisal Elkhatib is an attorney with vast experience in real estate transactions, development, and litigation allowing him to bring huge value to his clients. Mahmoud gives his back story including time in the laboratory as a chemist and starting various businesses prior to landing into his current career as an attorney! He breaks down foreclosure defense and how he is going to bat for his clients. Mahmoud explains the roles of attorneys and Title Company personnel in a real estate transaction and how his unique fee structure allows his clients to save on fees. Throughout the show, Mahmoud conveys the importance of having a knowledgeable attorney in your corner in any real estate transaction! 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: Mahmoud Faisal Elkhatib, EV Has Link: Mahmoud's Instagram Link: No More Mr. Nice Guy (Book Recommendation) Link: The Subtle Art of Not Giving a F*ck (Book Recommendation) Link: Tammie Lester (Loan Officer Referral) Guest Questions 01:54 Housing Provider Tip - Understand new rules around HVAC to strategically maintain and repair systems! 03:18 Intro to our guest, Mahmoud Faisal Elkhatib! 06:40 How do foreclosure defense firms work? 10:33 Jumping to a new career despite being established in another career! 24:00 Breaking down the roles of Attorneys and Title Companies. 32:27 Mahmoud’s unique attorney fee structure. 38:58 Wild attorney stories! 49:05 Mahmoud’s next 5 years! 56:05 What is your competitive advantage? 56:23 One piece of advice for new investors. 57:00 What do you do for fun? 57:32 Good book, podcast, or self development activity that you would recommend? 58:17 Local Network Recommendation? 58:58 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 hr and 2 mins
  • Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago

    Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago
    Jun 24 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 I need to know to pursue built-to-rent opportunities in Chicago?

    If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

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    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Guest: Prashanth Mahakali, PMPC

    Link: Episode 21: Leveraging an Architect for Chicago Permits, Building Violations, & Nonconforming and Illegal Units, with Prashanth Mahakali

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    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
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    17 mins
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