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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The Straight Up Chicago Investor podcast is an invaluable resource for newbie investors in the Chicago area. The hosts, Mark and Tom, along with their guests, bring a wealth of knowledge, experience, and tips to each episode. The podcast is highly informative, covering a wide range of topics related to real estate investing in Chicago and the surrounding areas. Mark and Tom are not only smart and knowledgeable but also have a great sense of humor that keeps listeners engaged. Each episode provides something new to learn and offers actionable insights for investors. I would highly recommend this podcast to anyone interested in real estate investing in Chicago.
One of the best aspects of The Straight Up Chicago Investor podcast is the high caliber of guests that are featured on the show. These guests provide valuable insights into the local real estate market and share their experiences, making it easier for listeners to navigate the unique challenges in the Chicago area. Additionally, the hosts' interviewing skills are top-notch, allowing them to extract key information from their guests and delve into important topics.
Another great aspect of this podcast is the hosts' accessibility and willingness to answer questions from listeners. They actively engage with their audience, providing additional support and advice beyond what is covered in each episode.
As for drawbacks, there are very few negative aspects to this podcast. Occasionally, there may be episodes that are more relevant to specific areas or niches within real estate investing that may not apply to all listeners. However, even these episodes still offer valuable insights and information that can be applied more broadly.
In conclusion, The Straight Up Chicago Investor podcast is an essential resource for anyone interested in real estate investing in the Chicago area. With knowledgeable hosts, informative guests, and actionable insights provided in each episode, this podcast offers a wealth of information that can help both beginners and experienced investors succeed in their ventures. Whether you are looking for advice on specific neighborhoods or want general guidance on real estate investing strategies, this podcast has it all. Don't miss out on this valuable resource if you are interested in Chicago real estate investing.
SUCI Co-Host Mark Ainley gives a presentation on his deals over the last 30 months at the WSBOA meetup! Mark shares details on various deals including flips, BRRRRs, and even short-term rentals. He explains how he sourced, financed, and stabilized these deals. He discusses biggest wins and top lessons learned. Mark closes the presentation with the biggest REI takeaways and a Q&A session 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: Mark Ainley, GC Realty & Development Link: Mark's Instagram Link: WSBOA Meetup Guest Questions: 06:07 Housing Provider Tip - Understand root causes of water intrusion to efficiently solve issues. 08:11 Mark's first acquisition with Lantz! 16:18 Lessons learned on Mark's Hoffman Estates deal. 19:57 Home run BRRRR deal in Schaumburg! 27:56 Mark's syndication deal. 30:36 A quick flip in Downers Grove and FHA househack in Jefferson Park! 36:14 Flip deal in Hanover Park. 37:28 Rough deal in Elgin! 41:18 Mark's recent deal in Rolling Meadows. 42:37 Locking up a Downers Grove Ranch property. 44:38 Experimenting with a Short-Term Rental project! 47:13 Mark's key takeaways! 52:08 Q&A. 59:37 Chicago fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
Can the government stop my insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance 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.
Newly elected Cook County Assessor Pat Hynes joins us to share his plan for bringing fair, accurate, and predictable property assessments! Pat starts by discussing the flaws in the current property assessment system and his plan to improve and simplify the system! He shares an emotive story on why he decided to take on the county assessor role. Pat gets granular on common mistakes made on tax appeals and the methodology behind accurate valuations. He closes with insights on the Chicago Bears Stadium site selection and an extremely 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! ============= 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: Pat Hynes, Cook County Link: Pay Hynes - Lyons Township Page Link: The Devil in the White City (Book Recommendation) Guest Questions: 02:07 Housing Provider Tip - Review property characteristics on tax assessor's website to catch inaccurate info! 02:56 Intro to our guest, Pat Hynes! 11:06 Bringing transparency to property taxation. 17:02 An idealized property valuation approach. 21:47 Pat's motivation to take on the Cook County Assessor role. 27:08 Common mistakes made on property tax appeals. 29:19 The process for valuing condominium buildings. 30:40 Simplifying the appeal process! 39:04 Property tax incentives for providing affordable housing. 43:48 Pat's criteria for a successful term as Cook County Assessor! 45:15 Tax implications for the Chicago Bears Stadium site selection! 50:06 Data Center Taxation. 51:49 What is your competitive advantage? 52:04 One piece of advice for new investors. 52:32 What do you do for fun? 53:09 Good book, podcast, or self development activity that you would recommend? 53:26 Local Network Recommendation? 54:34 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.
SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down a fraud story on a West Town property that he purchased! Tom dives deep into a recent purchase in West Town that involved ownership fraud when transferring title. He explains how the fraud was detected and how he navigated the process to reach a resolution. Throughout this show, Tom emphasizes the importance of being due diligence and having adequate insurance and documentation in place to protect yourself as best as possible! 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: Tom Shallcross, Co-host of Straight Up Chicago Investor Link: SUCI Ep 420 - Tom Shallcross Guest Questions: 01:38 Housing Provider Tip - Ensure drains are clear of debris or blockage to prevent issues during heavy rainfalls! 02:33 Intro to our guest, Tom Shallcross! 03:25 Intro to Tom's Fraud Property Story! 29:18 The process of clearing up title issues. 42:20 The stress associated with a fraud deal. 47:21 Managing partnerships when issues arise. 48:53 Chicago Fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
More Tenant Protections... Less Housing? Breaking Down Chicago's New RLTO ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser, NBOA Link: Amendment of Municipal Code Chapter 5-12 regarding Residential Landlord and Tenant Ordinance Link: Oppose Mayor Johnson's Proposed Ordinance 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.
Ignacio Gonzalez returns to discuss his Back of the Yards Coffee Shop development and his campaign for Chicago School Board! Ignacio jumps right in by sharing rent growth and property appreciation trends in the Back of the Yards neighborhood. He explains the struggles and lessons learned in completing the development of Dream Catcher Cafe. Ignacio talks about the impact of ICE raids in the neighborhood and the importance of contributing to community development and unity. He closes by explaining his motivation behind running for the Chicago Board of Education and shares how he would continue to positively impact the community if elected! 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: Ignacio Gonzalez of Chicago Board of Education Link: Dream Catcher Cafe Link: Beyond Legacy Homes Link: The Confessions of St. Augustine (Book Recommendation) Link: NAHREP Website Guest Questions: 01:34 Housing Provider Tip - Regularly check in with tenants to build rapport and promote communication. 02:32 Intro to our guest, Ignacio Gonzalez! 06:00 Rent growth and appreciation in Back of the Yards. 11:18 Navigating city inspections on a coffee shop development. 18:11 Lessons learned from Ignacio's coffee shop build out. 21:26 The impact of ICE raids in Back of the Yards. 24:36 Ignacio's campaign for the Chicago School Board. 40:51 What is your competitive advantage? 41:27 One piece of advice for new investors. 41:50 What do you do for fun? 42:35 Good book, podcast, or self development activity that you would recommend? 43:07 Local Network Recommendation? 44:14 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.
Matt Katsaros of Wildwood Investments returns to break down ground-up development projects that he's taking down in Chicago! Matt jumps right in by explaining how his experience in commercial real estate brokerage and acquisitions led him to starting and scaling his development business. He dives deep into a Lincoln Park development deal and shares insights on raising capital, finding deals, and construction to successfully complete a development deal! Matt dives into the nuances of adaptive reuse projects and the process of securing tax increment financing (TIF) funds. Matt closes with tremendous tips on apartment layouts and characteristics that help maximize rents! 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: Matt Katsaros of Wildwood Investments Link: Matt's LinkedIn Link: SUCI Ep 109 (Matt's First Appearance on SUCI) Link: Real Estate For Breakfast Podcast Link: Spittin Chiclets Podcast Guest Questions: 02:00 Housing Provider Tip - Document apartment conditions prior to tenant move-ins. 04:25 Intro to our guest, Matt Katsaros! 10:37 Dissecting Matt's Lincoln Park development deal! 18:32 Tips for raising capital. 28:28 Breaking down an office-to-residential adaptive reuse deal. 37:58 The process to secure TIF funds. 44:18 Earning steady income between the disposition of developments. 46:13 Matt's outlook on his business and on Chicago. 50:27 Apartment characteristics that maximize rents! 62:33 What is your competitive advantage? 62:47 One piece of advice for new investors. 63:05 What do you do for fun? 63:35 Good book, podcast, or self development activity that you would recommend? 64:03 Local Network Recommendation? 64:26 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.
Mark and Tom discuss the current fundamentals of the Chicago market with statistics provided by Jason Wagner. ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Tom & Mark, Straight Up Chicago Investor Podcast Link: Jason Wagner's Market Reports 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.
John Preston of Horvath & Tremblay joins us to discuss opportunities in multifamily and mixed-use assets on Chicago's North Side! John begins by discussing what it takes to build a successful brokerage business including early struggles before hitting his stride! He breaks down his process for reaching out to and converting seller leads and also explains the work brokers do that leads to a successful transaction. In typical SUCI fashion, John gets hyper-specific on neighborhoods that have seen great rent growth and areas where he sees investors putting their money! He closes with a bullish outlook on Chicago and emphasizes the importance of building market knowledge and networking to be successful in the game! 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: John Preston, Horvath & Tremblay | Email John: jpreston@hgapartments.com | Connect with John on LinkedIn Link: NBOA Chicago Guest Questions: 02:45 Housing Provider Tip - Understand catch basins and have a maintenance plan. 04:35 Intro to our guest, John Preston! 06:47 Getting off the ground as a real estate broker focusing on multi-family assets. 16:17 Troubling deals early on in John's career. 22:18 The work behind a successful listing. 29:30 Effectively following up with and converting leads! 31:27 How buyers can find opportunities in today's market. 34:57 John breaks down north side neighborhoods! 45:00 John's pick for a neighborhood with major upside! 50:17 John's bullish outlook on Chicago. 51:15 What is your competitive advantage? 52:15 One piece of advice for new investors. 53:04 What do you do for fun? 53:34 Good book, podcast, or self development activity that you would recommend? 54:23 Local Network Recommendation? 55:11 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.
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.
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.
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.
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.
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.
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 ============= Guest: 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.
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.
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.
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.
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.
What are the main differences in the 8.0 CAR contract vs the previous 7.0? ============= 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.
Dan Nelson is a real estate agent and investor with over 2 decades of experience flipping properties and buying rentals! Dan jumps right in by explaining his start in real estate and how success in poker helped fund his real estate business! He breaks down his first few flip projects including lessons learned and great tips on vetting contractors. Dan talks through the challenges of getting off the ground as a new real estate agent and provides advice for rookie agents. He gets granular on investment performance expectations across various Chicago neighborhoods including areas he is extra bullish on. Throughout the episode, Dan hammers home the importance of taking a 10,000-foot view letting time be your biggest asset when it comes to succeeding in real estate investing! 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: Dan Nelson, Dan Loves Houses Link: Dan's Instagram Link: Dan's Compass Page Link: The War of Art (Book Recommendation) Guest Questions: 02:03 Housing Provider Tip - Protect yourself against rental listing scams. 04:20 Intro to our guest, Dan Nelson! 13:02 How to find and vet contractors. 14:24 Dan's geographic area of focus! 18:01 Getting off the ground as a new real estate agent. 20:23 Chicago neighborhood expectations for investors! 30:25 Providing value as a real estate agent. 34:25 Common mistakes investors make when analyzing buildings. 41:33 Dan's outlook on Chicago! 44:23 What is your competitive advantage? 45:33 One piece of advice for new investors. 46:14 What do you do for fun? 46:25 Good book, podcast, or self development activity that you would recommend? 46:50 Local Network Recommendation? 47:14 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.
Brendan McElhaney, founder of Cash for Chicago Houses, is a real estate wholesaler and investor who specializes in sourcing off-market deals through direct-to-seller marketing! Brendan explains how he started in real estate with a house hack and how that helped him leave his corporate job to pursue real estate full time! He talks about renovation mistakes and leasing insights that he learned on his first few deals. Brendan dives deep on getting a wholesaling business off the ground, establishing a team, and lessons learned from wholesales gone wrong. He shares how he is leveraging social media to provide value to others and grow his business and also provides an outlook on Chicago. Throughout the show, Brendan demonstrates that hard work and grit have been the keys to his success! 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: Brendan McElhaney, Cash for Chicago Houses Link: Brendan's Instagram Link: Nick Jakubco (Attorney Referral) Link: SUCI Build Your Team Guest Questions: 03:19 Housing Provider Tip - Understand the limits on collectible security deposits. 05:09 Intro to our guest, Brendan McElhaney! 10:37 Leasing mistakes and lessons learned. 16:58 Getting a wholesaling business off the ground! 25:11 Wholesale deals gone wrong. 32:14 Building a reputation as a new wholesaler! 40:59 Establishing a wholesaling team and process. 43:34 Leveraging social media. 48:00 Brendan's outlook on his business and Chicago! 51:05 What is your competitive advantage? 52:24 One piece of advice for new investors. 53:08 What do you do for fun? 54:08 Good book, podcast, or self development activity that you would recommend? 54:42 Local Network Recommendation? 54:56 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.
How do I best prepare for an upcoming appraisal? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Tom & Mark, Straight Up Chicago Investor 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.
Ryan Bakke turns to discuss the power of smart business acquisitions and tax strategy to skyrocket returns and keep more money in your pocket! Ryan starts by reminding us the tax benefits of short-term rentals and real estate professional status. He explains the process of buying businesses including defining a buy box, identifying opportunities, and improving operations upon acquisition. He dives deep on lessons learned from operating businesses and tips on how to improve efficiencies through off-shore staffing. The show closes with great insights on assessing return on equity and investment to ensure your capital is working as hard as possible. 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: Ryan Bakke, Tax Strategy 365 Link: SUCI Ep 244 - Ryan Bakke Link: Ryan's Instagram Link: Influence (Book Recommendation) Link: SUCI Investor Meetups Page Guest Questions: 01:24 Housing Provider Tip - Understand the maintenance and life span of hot water heaters. 03:34 Intro to our guest, Ryan Bakke! 06:42 Leveraging short-term rentals for tax benefits. 11:26 Efficiently delegating to grow your business. 22:37 How to hire off-shore employees. 28:32 The process of buying a business. 32:03 Defining a "buy box" for a business. 39:07 Lessons learned from buying businesses. 46:08 Ryan's take on ROI and Chicago's future! 53:28 What is your competitive advantage? 53:37 One piece of advice for new investors. 53:46 What do you do for fun? 53:59 Good book, podcast, or self development activity that you would recommend? 54:17 Local Network Recommendation? 54:35 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.
Adam Friedberg, CEO of Mavrek Development, joins us to discuss the ins and outs of large-scale developments in Chicago. Adam starts by explaining how he started in real estate and hustled early on to learn development and value-add construction. He breaks down pitching development deals to investors and various methods for raising money. Adam talks about projects during COVID and how his team pivoted given the unforeseen circumstances. He gets granular on how to most efficiently cut construction costs without negatively impacting the quality of the final product. In typical SUCI fashion, Adam explains why he is doubling down on Chicago investments and why you should too! 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: Adam Friedberg, Mavrek Development Link: Adam's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: Abundance (Book Recommendation) Link: Crain's Chicago Guest Questions: 01:50 Housing Provider Tip - Simplify property management by setting expectations! 03:16 Intro to our guest, Adam Friedberg! 06:41 How to learn value-add construction in real estate. 10:35 Taking down commercial projects in Oak Park. 23:18 Pitching large development deals to investors! 27:10 Lessons learned from developments in 2020. 30:53 Acquiring The Saint Grand development. 37:20 Getting lean on construction costs. 44:14 Upcoming Mavrek developments! 55:31 Adam's bullish outlook on Chicago! 57:53 What is your competitive advantage? 58:00 One piece of advice for new investors. 58:15 What do you do for fun? 58:53 Good book, podcast, or self development activity that you would recommend? 59:34 Local Network Recommendation? 60:33 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.
Adam Friedberg, CEO of Mavrek Development, joins us to discuss the ins and outs of large-scale developments in Chicago. Adam starts by explaining how he started in real estate and hustled early on to learn development and value-add construction. He breaks down pitching development deals to investors and various methods for raising money. Adam talks about projects during COVID and how his team pivoted given the unforeseen circumstances. He gets granular on how to most efficiently cut construction costs without negatively impacting the quality of the final product. In typical SUCI fashion, Adam explains why he is doubling down on Chicago investments and why you should too! 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: Adam Friedberg, Mavrek Development Link: Adam's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: Abundance (Book Recommendation) Link: Crain's Chicago Guest Questions: 01:50 Housing Provider Tip - Simplify property management by setting expectations! 03:16 Intro to our guest, Adam Friedberg! 06:41 How to learn value-add construction in real estate. 10:35 Taking down commercial projects in Oak Park. 23:18 Pitching large development deals to investors! 27:10 Lessons learned from developments in 2020. 30:53 Acquiring The Saint Grand development. 37:20 Getting lean on construction costs. 44:14 Upcoming Mavrek developments! 55:31 Adam's bullish outlook on Chicago! 57:53 What is your competitive advantage? 58:00 One piece of advice for new investors. 58:15 What do you do for fun? 58:53 Good book, podcast, or self development activity that you would recommend? 59:34 Local Network Recommendation? 60:33 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.
What is the process for assuming a VA or FHA loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Scanlon, The Axon Group (EXP Realty) 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.
Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want! Josh jumps right in by explaining the concept of his book and the neuroscience of persuasion! He shares insights on how the brain works as it relates to persuasion and gives tactical negotiation tips. Josh describes the process of writing his book and the impact that artificial intelligence and technology are having on communication. This show is full of golden nuggets to leverage on your next real estate negotiation and to help create more win-win situations in business! 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: Josh Bandoch, Illinois Policy Institute Link: How To Get What You Want (Josh's New Book) Link: Josh's LinkedIn Link: SUCI Ep 347 - Josh Bandoch Link: GC Realty Maintenance Blog Link: Mike Glasser - NBOA Link: How to Stop Worry and Start Living (Book Recommendation) Link: Thinking, Fast and Slow (Book Recommendation) Guest Questions: 02:37 Housing Provider Tip - Have contacts to efficiently solve all maintenance requests! 04:37 Intro to our guest, Josh Bandoch! 06:48 The neuroscience of persuasion. 11:52 Understanding persuasion to get deals done! 16:27 Tactical negotiation tips. 24:10 The process of publishing a book. 36:20 The impact of AI on communication. 38:45 What is your competitive advantage? 39:04 One piece of advice for new investors. 39:34 What do you do for fun? 39:41 Good book, podcast, or self development activity that you would recommend? 41:14 Local Network Recommendation? 41:28 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.
Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want! Josh jumps right in by explaining the concept of his book and the neuroscience of persuasion! He shares insights on how the brain works as it relates to persuasion and gives tactical negotiation tips. Josh describes the process of writing his book and the impact that artificial intelligence and technology are having on communication. This show is full of golden nuggets to leverage on your next real estate negotiation and to help create more win-win situations in business! 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: Josh Bandoch, Illinois Policy Institute Link: How To Get What You Want (Josh's New Book) Link: Josh's LinkedIn Link: SUCI Ep 347 - Josh Bandoch Link: GC Realty Maintenance Blog Link: Mike Glasser - NBOA Link: How to Stop Worry and Start Living (Book Recommendation) Link: Thinking, Fast and Slow (Book Recommendation) Guest Questions: 02:37 Housing Provider Tip - Have contacts to efficiently solve all maintenance requests! 04:37 Intro to our guest, Josh Bandoch! 06:48 The neuroscience of persuasion. 11:52 Understanding persuasion to get deals done! 16:27 Tactical negotiation tips. 24:10 The process of publishing a book. 36:20 The impact of AI on communication. 38:45 What is your competitive advantage? 39:04 One piece of advice for new investors. 39:34 What do you do for fun? 39:41 Good book, podcast, or self development activity that you would recommend? 41:14 Local Network Recommendation? 41:28 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.
Jay Patel and Tedi Nati of JP Acquisitions join us to explain how they've leveraged mentors and discipline to build a sizable multifamily portfolio on Chicago's West Side! Jay and Tedi explain how they networked and built their team to set themselves up for success when starting in real estate! They break down raising money and setting up a syndication to acquire their first multifamily building in Austin. The duo discuss their next 16-unit building acquisition and lessons learned on that deal. Jay and Tedi close by sharing their motivative business plan hammering home their go-getter attitude which has led to their great success! 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: Jay Patel & Tedi Nati, JP Acquisitions Link: Jay's LinkedIn Link: Tedi's LinkedIn Link: Frank Jaffe (Attorney Referral) Link: Eric Kogan (Network Referral) Guest Questions: 01:08 Intro to our guests, Jay and Tedi! 09:20 Learning how to execute a real estate deal! 16:34 Jay and Tedi''s first syndication deal. 22:45 Software and tools for asset management. 27:07 Mistakes on an 8-unit acquisition. 33:38 The importance of an experienced team. 38:04 Acquiring a 16-unit building in Austin. 44:35 How to make money when starting a syndication? 49:58 2-Year outlook for Jay and Tedi! 56:10 What is your competitive advantage? 56:30 One piece of advice for new investors. 56:40 What do you do for fun? 56:55 Good book, podcast, or self development activity that you would recommend? 57:32 Local Network Recommendation? 58:20 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.
What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jonathan Klemm, Quality Builders 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.
Samuel Pavlovcik of the Pavlovcik Architecture returns to explain opportunities brought by the expanded city-wide Additional Dwelling Unit (ADU) Ordinance! Samuel jumps right in by explaining the process and expectations on obtaining a Zoning Change without leveraging the ADU ordinance! He dives deep on various Zoning and Building Code requirements when looking to build and/or legalize a basement ADU. Samuel breaks down various requirements on coach house ADUs and ground-level commercial ADU conversions. He closes with tips for successful ADU projects and shares top pitfalls to avoid when leveraging the program! 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: Samuel Pavlovcik, Pavlovcik Architecture Link: Pavlovcik Architecture's Instagram Link: SUCI Ep 97 - Samuel Pavlovcik Link: SUCI Ep 264 - Samuel Pavlovcik Link: Chicago Zoning Map Link: Tom Moore (Zoning Attorney Referral) Link: The Toyota Way (Book Recommendation) Guest Questions: 03:08 Housing Provider Tip - Optimize your rental listings to attract tenants and avoid vacancy! 05:35 Intro to our guest, Samuel Pavlovcik! 06:10 The 101 on Chicago Zoning changes. 13:34 Building Department considerations for legalizing an ADU. 23:03 Easiest ways to improve building efficiency. 23:25 City wide expansion of Chicago's ADU Ordinance. 32:42 Nuances on coach house ADUs. 38:55 Ground-level Commercial vs Basement ADUs! 44:37 Top mistakes when leveraging the ADU program. 46:31 What is your competitive advantage? 49:16 One piece of advice for new investors. 49:28 What do you do for fun? 49:48 Good book, podcast, or self development activity that you would recommend? 50:00 Local Network Recommendation? 50:57 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.
Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and Efficiency! Joe starts with a story on acquiring a mixed-use building to establish his business and invest simultaneously! He breaks down his background of growing up in a real estate family and transitioning into the business. Joe gets granular on causes for building inefficiencies and means for improving building performance. He explains top considerations for heating system options and closes out with some wild inspection stories! 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: Joe Konopacki, Insight Property Services Link: Joe's LinkedIn Link: Modern Wisdom (Podcast Recommendation) Link: The E-Myth Revisited (Book Recommendation) Guest Questions: 02:24 Housing Provider Tip - Understand the benefits of lease agreements over month-to-month agreements! 04:15 Intro to our guest, Joe Konopacki! 10:16 Advantages of mixed-use buildings. 12:02 Growing up in a real estate family and transitioning into the business. 23:03 Easiest ways to improve building efficiency. 31:12 Understanding the efficiency of boilers! 43:05 Considerations for electric heating systems. 52:03 Cost analysis of switching from boilers to central HVAC! 60:27 Incentive opportunities for solar energy systems. 67:13 Wild inspection stories! 71:37 What is your competitive advantage? 73:27 One piece of advice for new investors. 73:38 What do you do for fun? 73:54 Good book, podcast, or self development activity that you would recommend? 74:40 Local Network Recommendation? 75:12 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.
What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser & Aron Borstein, NBOA PAC | An Evening with Rahm Emanuel ⭐⭐Get your tickets today!⭐⭐ 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.
Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward! Alderman Villegas starts by discussing how zoning changes can be utilized to create win-win situations for investors and members of a community or ward! He talks about how he and his fellow members of City Counsel were able to influence the city's approved budget with the needs of their constituents at the forefront. Alderman Villegas breaks down why he chose to withdraw his Ward from the Northwest Housing Ordinance. He closes with an extremely bullish outlook on Chicago leaving us motivated to continue doubling down on our great city! 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 Gil Villegas, City of Chicago's 36th Ward Link: Alderman Villegas' Facebook Link: Alderman Villegas' Instagram Link: The 48 Laws of Power (Book Recommendation) Link: NBOA Chicago (Network Recommendation) Guest Questions: 03:31 Housing Provider Tip - Understand lease renewal notices to remain compliant! 05:28 Intro to our guest, Alderman Villegas! 07:19 Zoning changes to create affordable housing. 18:48 City council's involvement with the city's approved budget. 25:45 How Aldermen work together to make positive impacts! 35:05 Drawbacks of the Northwest Housing Ordinance. 43:34 How Aldermen utilize facts and community input to make decisions. 45:39 Exciting developments in the 36th ward! 48:28 Alderman Villegas' outlook on Chicago. 51:41 What is your competitive advantage? 52:11 One piece of advice for new investors. 54:26 What do you do for fun? 55:46 Good book, podcast, or self development activity that you would recommend? 56:08 Local Network Recommendation? 56:31 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.
What are the common mistakes made when handling lease renewals? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty 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.
Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Throughout the show, Zack provides insights on handling various code violation scenarios to give you an edge against the competition! 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: Zack Limbaugh, The Limbaugh Law Firm Link: Zack's LinkedIn Link: SUCI Ep 333 - Zack Limbaugh Link: SUCI Ep 79 - Gary Davidson Link: Essentialism (Book Recommendation) Guest Questions: 02:35 Housing Provider Tip - Understand the true costs of not allowing pets in your rentals! 04:44 Intro to our guest, Zach Limbaugh! 10:23 Buying a property with code violations. 16:48 Lending considerations for violations exist. 23:52 Protecting yourself against fines for code violations! 31:03 Ensuring violations are found during due diligence. 43:15 Common violation tickets to watch out for! 50:35 Crazy code violation stories! 51:17 What is your competitive advantage? 51:32 One piece of advice for new investors. 51:39 What do you do for fun? 51:51 Good book, podcast, or self development activity that you would recommend? 52:03 Local Network Recommendation? 52:18 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.
Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to create equity! Zach gives property management insights for house hackers which are centered around doing right by tenants and people in general. He explains the ins and outs of acquiring a property by assuming a VA loan. Throughout the episode, Zach demonstrates that growing a portfolio as a busy professional is doable and that the financial reward far outweighs the work that is required! 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: Zach Posey, Chicago Multifamily Club Link: Chicago Multifamily Club Meetup Link: Wisdom Takes Work (Book Recommendation) Link: SUCI Ep 52 - Aaron Zimmerman Link: SUCI Ep 326 - RJ de Leon Guest Questions: 01:58 Housing Provider Tip - Understand easy fixes for malfunctioning garbage disposals! 03:57 Intro to our guest, Zach Posey! 07:38 Starting off with a 4-unit house hack. 17:25 Acquiring a second house hack in Roscoe Village. 26:28 Property Management tips for house hackers! 28:44 Leveraging assumable loans to make the numbers pencil. 34:41 The value of networking events. 37:40 Zach's REI goals and outlook on Chicago! 42:42 What is your competitive advantage? 43:13 One piece of advice for new investors. 43:35 What do you do for fun? 43:50 Good book, podcast, or self development activity that you would recommend? 44:40 Local Network Recommendation? 45:39 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.
What is real estate professional status and why is it important for investors? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Michael Procaccio, Pro Financial Services Group Inc 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.
Reed Meyer, founder and managing broker at Lease312, shares top tier leasing advice and how connecting with mentors has propelled his real estate journey's growth at such a young age! Reed starts off by detailing the process of acquiring his first property; a 3-unit house hack in Logan Square. He talks about purchasing an industrial warehouse and flipping it for double the price in just 45 days! Reed shares golden insights on apartment listing marketing, leasing, and tenant expectations in prime North Side neighborhoods. To conclude, Reed gives a 5 year outlook on his business goals and Chicago's residential rental market! 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: Reed Meyer, Lease312 Link: Reed's LinkedIn Link: SUCI Ep 421 - Alec Greenberg Link: SUCI Ep 259 - Sal Becovic Link: SUCI Ep 22 - Matt Fritzshall Link: SUCI Ep 51 - John Westbrook Link: Gabe Horstick (Network Referral) Link: Zeckendorf Autobiography Guest Questions: 01:56 Housing Provider Tip - Get great pictures, get floor plans, and be responsive to optimize leasing of apartments! 03:15 Intro to our guest, Reed Meyer! 06:45 Reed's first house hack. 11:37 The nuances of industrial property investing. 16:40 Reed's transition from corporate to real estate full time! 22:12 Top leasing mistakes by landlords. 29:15 Jumping into a 5-unit house hack! 34:00 Tenant expectations in Lakeview. 40:50 Outlook on the Chicago leasing market and rent growth! 42:52 Reed's 5 year business outlook. 45:43 What is your competitive advantage? 45:53 One piece of advice for new investors. 46:10 What do you do for fun? 46:54 Good book, podcast, or self development activity that you would recommend? 47:26 Local Network Recommendation? 48:08 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.
Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions. Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Markets Tax Credits. Throughout the show, Darryl demonstrates his deep knowledge in Tax Credits and conveys how it can be a super powerful tool for investors who know how to leverage it! 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: Darryl Jacobs, Ginsberg Jacobs Link: Sonny Ginsberg (Network Referral) Link: SUCI Ep 26 - Neal Bawa Guest Questions: 01:49 Housing Provider Tip - Ensure proper transfer of utilities when purchasing a property to avoid outages! 04:09 Intro to our guest, Darryl Jacobs! 13:26 Understanding Opportunity Zones. 25:04 Opportunity Zones 1.0 vs 2.0! 32:14 New Markets Tax Credits. 54:48 Other tax credit resources for investors. 59:55 What is your competitive advantage? 62:48 One piece of advice for new investors. 64:11 What do you do for fun? 64:37 Good book, podcast, or self development activity that you would recommend? 65:33 Local Network Recommendation? 66:02 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.
What are recent legal updates to the 2026 lease and new squatter laws? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast and GC Realty & Development LLC 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
Jake Fugman and Mike Scanlon of The Axon Group return to forecast Chicago's Real Estate Market in 2026! Jake and Mike kick things off by reflecting on their 2025 predictions including office space leasing trends, downtown sales stats, and impacts of the Northwest Side Preservation Ordinance. The duo then make their 2026 predictions with topics ranging from ADU Zone expansion to creative mortgage solutions to help with affordability. Jake and Mike close out with an outlook on interest rates and the future of real estate based on recent brand mergers! 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: Jake Fugman & Mike Scanlon, The Axon Group Link: The Axon Group Instagram Link: SUCI Ep 354 - 2025 Predictions with Jake and Mike Link: SUCI Ep 398 - Paul de Luca Link: With Roam Website Link: The Almanack of Naval Ravikant (Book Recommendation) Guest Questions: 01:13 Housing Provider Tip - Don't get stuck in analysis paralysis and take action in 2026! 02:46 Intro to our guests, Jake Fugman and Mike Scanlon! 04:10 Reflecting on 2025 bonus depreciation predictions. 07:51 Office vacancy trends in 2025. 11:43 Impacts of the Northwest Side Preservation Ordinance. 19:53 Chicago Loop and downtown sales stats! 24:20 Real estate predictions in 2026! 33:48 Expansion of the Chicago ADU Zones. 42:12 Where are mortgage rates going? 50:16 Real estate brand consolidations. 61:40 What is your competitive advantage? 63:45 One piece of advice for new investors. 65:32 What do you do for fun? 66:01 Good book, podcast, or self development activity that you would recommend? 67:33 Local Network Recommendation? 69:42 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.
Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock's downtown redevelopment plan and also speaks to city corridors with development opportunities. Jessica explains "infill" sites, metrics for successful developments, and strategic planning of developments to allow for future adaptive reuse. Throughout the show, Jessica demonstrates a passion for sustainable developments that enhance the quality of life for the residents of Woodstock! 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: Jessica Erickson, City of Woodstock Link: Jessica's LinkedIn Link: Woodstock Comprehensive Plan Link: The Prof G Pod (Podcast Recommendation) Link: Heartland Realtor Organization (Network Referral) Guest Questions: 02:13 Housing Provider Tip - Utilize water shut off valves at vacant properties to prevent issues! 03:52 Intro to our guest, Jessica Erickson! 09:14 Jumping into Economic Development in Woodstock, IL. 16:50 Woodstock's downtown redevelopment plan. 23:44 Breaking down "infill" sites. 25:54 Measuring successful developments. 29:28 Redevelopment opportunities in Woodstock. 31:27 Future-proofing development sites. 38:41 Closing remarks on the upside of Woodstock! 43:12 Woodstock's competitive advantage? 43:39 One piece of advice for new investors. 44:33 What do you do for fun? 44:55 Good book, podcast, or self development activity that you would recommend? 45:48 Local Network Recommendation? 46:16 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.
Do you need a HELOC on your investment property? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Benjamin Stef, NEXA Mortgage 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.
Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026! Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ryan gets granular on latest foreclosure statistics and provides his outlook on the REO market heading into 2026. He closes with his take on Chicago's crime problem and the neighborhoods that he is 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: Ryan Smith, RE/MAX Properties Link: Ryan's Instagram Link: SUCI Ep 70 - Ryan Smith Link: SUCI Ep 28 - Ryan Smith Link: The Chicago Way (Podcast) Link: DAWGS Vacant Property Security Guest Questions: 02:05 Housing Provider Tip - Understand manufacturer warranties on appliances and reconsider extended warranties! 04:15 Intro to our guest, Ryan Smith! 10:47 Risks associated with buying properties at the auction. 13:12 Understanding properties in receivership. 15:55 Expectations on REO transactions! 25:15 Key Foreclosure Statistics! 35:54 Ryan's outlook on the foreclosure market. 42:55 Promising south and west side neighborhoods. 46:19 Solving Chicago's largest issues. 47:20 What is your competitive advantage? 48:12 One piece of advice for new investors. 49:20 What do you do for fun? 49:50 Good book, podcast, or self development activity that you would recommend? 50:45 Local Network Recommendation? 51:51 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.
Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance! Jonathan starts by explaining partnership pitfalls to avoid based on recent changes within his business. He gets vulnerable by discussing a multifamily investment on Chicago's southside that involved various evictions and a $400,000 fire caused by a problem tenant! Jonathan shares tips on the mindset required to weather business storms and turns to more positive news by discussing some large renovation projects that his company is working on. He closes with how he has leveraged networking to skyrocket his business and shares his plans for continued growth going into the new year! 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: Jonathan Klemm of Quality Builders Link: Founders (Podcast Recommendation) Link: SUCI Ep 250 - Jonathan Klemm Link: SUCI Ep 206 - Prashanth Mahakali Guest Questions: 02:07 Housing Provider Tip - Perform adequate due diligence specifically as snowy conditions are present! 03:44 Intro to our guest, Jonathan Klemm! 06:50 Partnership pitfalls to watch out for. 15:10 Jonathan's scary "fire" deal! 29:41 Mindset for getting through a difficult deal. 42:41 Large renovation projects by Quality Builders. 48:26 Leveraging BiggerPockets to grow a business. 50:36 Jonathan's 5 Year Outlook! 53:20 What is your competitive advantage? 54:00 One piece of advice for new investors. 54:31 What do you do for fun? 54:38 Good book, podcast, or self development activity that you would recommend? 55:32 Local Network Recommendation? 56:51 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.
Is now a good time for me to purchase in Chicago? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets! Alec explains how he transitioned from the corporate real estate world to a more entrepreneurial position at Base 3 Development. He describes how he "stretched" out of his comfort zone by jumping into a 6-unit gut rehab project off the bat and shares lessons learned! Alec shares insights on large residential development projects including zoning, underwriting, and leasing considerations. He closes with tips on leveraging VAs and off-shore staffing solutions for optimal property management while also providing 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! ============= 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: Alec Greenberg, Base 3 Development Link: Staffolio Website Link: Chicago Cityscape Website Link: EUBA - NBOA Chicago Link: SUCI Ep 412 - Luke Helliker Link: On The Road (Book Recommendation) Guest Questions: 02:13 Housing Provider Tip - Understand lease changes coming in 2026! 03:13 Intro to our guest, Alec Greenberg! 08:32 Lessons learned from Alec's first gut rehab project. 13:54 Jumping into a 48-unit development. 22:25 Tips for leasing in the off-season. 25:26 Underwriting rules of thumb on large developments. 35:43 Leveraging VAs and other tools for property management. 49:16 Alec's outlook on Chicago! 51:57 What is your competitive advantage? 52:23 One piece of advice for new investors. 52:39 What do you do for fun? 53:02 Good book, podcast, or self development activity that you would recommend? 53:43 Local Network Recommendation? 55:18 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.
SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down everything you need to know about architectural plans and permits in Chicago! Tom discusses when you need plans and permits for a project and when it's appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons learned on design and functionality particularly on luxury redevelopments! He closes with insights on dormer additions and considerations for ADUs and historic district remodels that will add to your permit approval timeline! 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: Tom Shallcross, Straight Up Chicago Investor Link: SUCI Ep 235 - Tom Shallcross Guest Questions: 02:32 Housing Provider Tip - Understand 2026 leasing law changes regarding minors on leases! 04:33 Intro to our guest, Tom Shallcross! 05:35 The process of developing plans and permitting. 14:11 Top design and functionality mistakes! 16:16 Must-have amenities in luxury remodels. 20:40 Timeline for creation of architectural drawings. 27:23 The role of expeditors. 35:29 Design considerations for dormer additions. 41:40 What do you do for fun? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
How do I navigate the rent determination process for Section 8 applicants in Chicagoland? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast 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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
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