Straight Up Chicago Investor

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462

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Jun 2026

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About the show

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.

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June 11, 2026Episode 4581 hr 20 min

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

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.

June 9, 2026Episode 45712 min

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

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.

June 4, 2026Episode 4561 hr 13 min

Episode 456: Inside Chicago's Commercial Lending Landscape w/ Asher Motew and Quinn Keenan

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.

May 28, 2026Episode 4551 hr 4 min

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

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.

May 26, 2026Episode 45411 min

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

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.

May 21, 2026Episode 4531 hr 15 min

Episode 453: Breaking Down Chicagoland Syndications w/Duke Dennis & Bryan Sonn

Duke Dennis and Bryan Sonn of GC Realty & Development join us to explain the ins and outs of Chicagoland Industrial Investments! Duke and Bryan explain how they got their start in industrial real estate. They dive deep on the differences between residential and industrial property investing. They discuss how they went from a property manager to an owner operator and share ways to add value to industrial properties. Duke and Bryan get granular on a deal in Mundelein including details on the capital raising, acquisition, stabilization, and hurdles that come up during the process. Through the show, Duke and Bryan provide insights to industrial property investing and convey the major ROI opportunities in this often overlooked asset class! 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: Duke Dennis & Bryan Sonn, GC Realty & Development Link: Email Bryan: Bryan@GCrealty.inc | Bryan's LinkedIn Link: Email Duke: Duke.Dennis@GCrealty.inc | Duke's LoopNet Page Guest Questions: 00:52 Housing Provider Tip - Understand best tenant applications in a competitive market! 02:33 Intro to our guests, Bryan Sonn and Duke Dennis! 06:48 Managing industrial properties compared to residential. 10:38 From property manager to owner operator. 20:03 Value-add components on industrial properties. 30:50 Breaking down a Mundelein industrial deal. 37:46 Dealing with and overcoming unexpected challenges. 41:28 Avoiding liquidity issues on large scale projects. 53:07 Benefits of being a passive investor in a reputable syndication fund. 55:53 Opportunities in smaller scale industrial deals. 63:36 5 Year Outlook on Chicagoland Industrial Property Market! 67:40 What is your competitive advantage? 68:50 One piece of advice for new investors. 71:10 What do you do for fun? 71:36 Good book, podcast, or self development activity that you would recommend? 72:07 Local Network Recommendation? 72:17 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.

May 14, 2026Episode 4521 hr 3 min

Episode 452: Crazy Stories of Off-Market Real Estate Deals with Igor Mike Kajpust

Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states! Igor breaks down his first few deals which includes an $800 land deal in Colorado and a distressed single family home in Indiana! He shares countless stories on auction properties, cold calling, and learning the process of wholesaling to create deal flow. Igor explains mistakes made on buying deals with quit claim deeds and due diligence. He gets granular on how he gained lead generation momentum through PPC, SEO, and various other real estate marketing strategies which propelled his business. Through the show, Igor shares entertaining stories that exemplify how taking massive action is the key to success in REI! 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: Igor Mike Kajpust, Evolved Property Group Link: Igor's Instagram Link: SUCI Ep 166 - J Scott Link: ilFLS Website Guest Questions: 01:35 Housing Provider Tip - Account for expenses related to lead plumbing lines when purchasing older buildings. 02:57 Intro to our guest, Igor Mike Kajpust! 04:52 Getting scrappy to find the first few deals. 19:00 Learning the process of wholesaling. 26:48 Transitioning to flipping properties. 35:01 Improving business processes and efficiency. 37:03 Building a rental portfolio in Chicago. 40:21 Distressed property horror stories! 47:45 Jumping into private lending in Chicago. 51:37 How to navigate the auction process. 57:57 What is your competitive advantage? 58:25 One piece of advice for new investors. 59:24 What do you do for fun? 59:57 Good book, podcast, or self development activity that you would recommend? 60:35 Local Network Recommendation? 61:00 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.

May 12, 2026Episode 45116 min

Episode 451: Leveraging the Big Beautiful Bill to Minimize Tax Exposure

What do real estate investors need to know about the Big Beautiful Bill? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Aaron Zimmerman, Brick House CPAs 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.

May 7, 2026Episode 45054 min

Episode 450: Alderman Bennett Lawson & The 44th Ward

Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago! Alderman Lawson jumps right in by explaining the successful development in Wrigleyville including partnering with the Ricketts family! He breaks down successful developments including Advocate Masonic Hospital in Lakeview and across the 44th Ward. Alderman Lawson gives practical advice for developers to help increase the chance of having aldermanic support on potential projects! He dives deep on the ADU Pilot Program, its city wide expansion, and how it can best be leveraged to bring much needed housing supply to the city. This show is full of golden insights on Zoning and Development that you won't want to miss! 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: Alderman Bennett Lawson, City of Chicago 44th Ward Link: Alderman Lawson's Instagram Link: Chicago ADU Program Link: Chicago's Great Fire (Book Recommendation) Link: Tom Moore (Zoning Attorney) Guest Questions: 01:55 Housing Provider Tip - Leverage rent payment services to allow tenants to build their credit history! 03:38 Intro to our guest, Alderman Lawson! 10:55 The development history of Wrigleyville! 18:20 Previous developments in the 44th Ward. 23:30 Advice for developers seeking support from aldermen. 27:18 The background of the Chicago ADU Program! 31:41 Lessons learned from the ADU Pilot Program. 44:08 Potential solutions for the housing supply issue. 48:50 What is your competitive advantage? 49:11 One piece of advice for new investors. 49:35 What do you do for fun? 49:48 Good book, podcast, or self development activity that you would recommend? 50:48 Local Network Recommendation? 51:15 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.

April 30, 2026Episode 44959 min

Episode 449: Zero to Thirty Units Creatively with Mike Scanlon

Mike Scanlon of the Axon Group returns to share his personal real estate journey with several insights on how he has reached his success! Mike starts by discussing his background prior to real estate and then jumps into his first property acquisition which was a rent-by-the-room condo house hack! He shares how he got gritty and creative to finance and acquire a pair of distressed properties in University Park. Mike breaks down how he identified value and got a down payment to purchase a prime 3-unit house hack in Lakeview! He explains how he grinded to build his real estate brokerage business and used commissions to fund his portfolio. Mike closes the show with how his investment strategy has shifted and with Chicago neighborhoods that he's extra bullish on! 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: Mike Scanlon, The Axon Group Link: Mike's Instagram Link: The Axon Group Instagram Link: SUCI Ep 427 - 2026 Predictions with the Axon Group Link: SUCI Ep 398 - Paul de Luca Link: Never Split the Difference (Book Recommendation) Guest Questions: 01:50 Housing Provider Tip - Consider offering tenants a valuable unit improvement when enforcing large rent increases. 03:23 Intro to our guest, Mike Scanlon! 10:17 Mike's start in real estate. 17:25 How Mike acquired his second deal. 23:45 Buying a prime 3-unit in Lakeview! 32:49 Building a pipeline of leads as a real estate broker. 37:16 A creative 8-unit deal in Melrose Park! 43:27 Mike's shift in investment strategy. 49:01 Up and coming Chicago neighborhoods! 50:25 What is your competitive advantage? 52:15 One piece of advice for new investors. 54:01 What do you do for fun? 55:23 Good book, podcast, or self development activity that you would recommend? 56:38 Local Network Recommendation? 57:33 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.