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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 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)

    Episode 458: Zillow vs Compass And The State of the Chicago Market (Renovo Live Event)
    Jun 11 2026
    Tom and Mark interview some of Chicago's Brightest Real Estate Stars during a Renovo Networking Event featuring an interview of Thad Wong! Discussions range from areas investors are targeting in Chicago, breaking down the MRED and Zillow lawsuits, and lessons learned on luxury developments and operating apartment buildings. This show is full of wisdom from some of the best minds in Chicago Real Estate so have your notepad ready! 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: Some of Chicago's Brightest Real Estate Stars during a Renovo Networking Event--including an interview with Thad Wong Link: Thad Wong Link: SUCI Ep 381 - Kevin Werner Link: SUCI Ep 255 - Eric Workman Link: SUCI Ep 368 - Joe Smazal and Ann Keilly Link: SUCI Ep 326 - RJ de Leon Link: Flora Blahnik Team Guest Questions: 03:17 Investing in Elgin with Mark Fostrom. 09:12 Renovo's formula to success with Kevin Werner! 17:18 Daniel Rosen discusses the evolution of Renovo. 26:23 Scaling a podcast and multi-family with Joe Smazal. 40:03 State of RE Brokerage with Luke Blahnik and Anthony Flora. 49:40 Luxury developments with RJ de Leon. 58:26 Renovation market in NW Indiana with Daniela Rodriguez. 66:22 Workman Lending Team's outlook on Chicago and business growth! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
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    1 hr and 20 mins
  • Episode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns

    Episode 457: Proactive Tax Planning Advice to Save on your 2026 Tax Returns
    Jun 9 2026

    What steps should I take to best prepare for my 2026 tax returns?

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

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Aaron Zimmerman, Brick House CPAs

    Link: SUCI Episode 52

    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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    13 mins
  • 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
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