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Straight Up Chicago Investor

Straight Up Chicago Investor

By: Straight Up Chicago Investor
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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 456: Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan

    Episode 456: Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan
    Jun 4 2026
    Asher Motew and Quinn Keenan of Essex Capital Markets break down keys to their early career success in the Chicago Commercial Lending Market! Asher and Keenan start by explaining their background coming from real estate families and how they've been able to pave their own path in commercial lending. They share their service offerings including creative solutions they bring that traditional lenders may not have. The duo talks about some successful deals and how those were put together while also explaining why their partnership has worked so well. They get tactical on underwriting expenses and NOI on deals to achieve desired lending outcomes. Through the show, Asher and Quinn showcase that being hungry and grinding has been the key to tremendous growth early on in their careers. 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: Asher Motew and Quinn Keenan, Essex Capital Markets Link: Essex Capital Market's Instagram (@EssexCapitalMarkets) Link: Matt Feo (Essex Realty Group) Link: Asher Motew's Instagram (@AMo2.Cre) Link: Asher Motew's LinkedIn Link: Quinn Keenan's LinkedIn Guest Questions: 02:59 Housing Provider Tip - Understand and leverage cost segregation studies. 04:44 Intro to our guests, Asher Motew and Quinn Keenan! 13:20 Jumping into commercial mortgage brokerage. 21:20 The value offered by commercial debt brokers. 31:04 Breaking down a successful deal! 39:56 Asher and Quinn's complimentary partnership! 46:09 Biggest financing hurdles on deals! 50:54 Essex Capital Markets' role in the lending process. 61:10 Tactical tips on underwriting expenses and income. 66:36 What's next for Asher and Quinn. 69:18 What is your competitive advantage? 69:35 One piece of advice for new investors. 69:43 What do you do for fun? 69:52 Good book, podcast, or self development activity that you would recommend? 70:04 Local Network Recommendation? 71:27 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
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    1 hr and 14 mins
  • Episode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner

    Episode 455: The Facts Behind The Red Hot Chicago Market with Jason Wagner
    May 28 2026

    Jason Wagner, Managing Broker of Greystone Realty, returns to discuss the state of the Chicago Real Estate market and the power of buy and hold investments.

    Jason starts by discussing buyer expectations and demand in today's market. He dives into the data behind Chicago property value appreciation and rent growth across different neighborhoods! Jason shares client success stories involving house hacks, using leverage responsibly, and adding value to create meaningful equity gains. He closes with top advice for new investors and an extremely bullish outlook on select neighborhoods and Chicago as a whole!

    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

    =============

    Guest: Jason Wagner, Greystone Realty

    Link: Jason's Instagram

    Link: SUCI Ep 402 - Jason Wagner

    Link: Wagner Report

    Link: Wonderful Togbey (Network Referral)

    Link: The 10X Rule (Book Recommendation)

    Guest Questions:

    01:07 Housing Provider Tip - Understand and adhere to flood disclosure requirements on leases.

    03:03 Intro to our guest, Jason Wagner!

    09:31 Buyer demand in today's market.

    15:28 Property appreciation and lack of inventory.

    22:10 Chicago neighborhoods that Jason is bullish on!

    33:42 The power of rent growth and appreciation.

    36:43 The latest on the Wagner Report.

    47:26 Top lessons learned as a young investor!

    50:35 Top Chicagoland neighborhoods and areas with upside!

    53:42 Jason's bullish outlook on Chicago real estate.

    55:09 What is your competitive advantage?

    55:34 One piece of advice for new investors.

    56:05 What do you do for fun?

    58:38 Good book, podcast, or self development activity that you would recommend?

    59:00 Local Network Recommendation?

    60:38 How can the listeners learn more about you and provide value to you?

    -----------------

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.
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    1 hr and 4 mins
  • Episode 454: How To Assign Contracts Like a Pro with Chance Badertscher

    Episode 454: How To Assign Contracts Like a Pro with Chance Badertscher
    May 26 2026

    What do I need to be aware of when assigning a contract?

    =============

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Chance Badertscher, Chance The Lawyer

    Email the Show: StraightUpChicagoInvestor@gmail.com

    Link: Build Your Team | Straight Up Chicago Investor Podcast

    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

    -----------------

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2026.
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    12 mins
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