Straight Up Chicago Investor

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.

Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs 01/29/2026

Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Darryl Jacobs, Link: Link: 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: Copyright of Straight Up Chicago Investor 2026. /episode/index/show/straightupchicagoinvestor/id/39913625

Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley 01/27/2026

Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon 01/22/2026

Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Jake Fugman & Mike Scanlon, Link: Link: Link: Link: Link: 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: Copyright of Straight Up Chicago Investor 2026. /episode/index/show/straightupchicagoinvestor/id/39814560

Episode 426: Reshaping Suburban Woodstock with Jessica Erickson 01/15/2026

Episode 426: Reshaping Suburban Woodstock with Jessica Erickson 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Jessica Erickson, Link: Link: Link: Link: 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: Copyright of Straight Up Chicago Investor 2026. /episode/index/show/straightupchicagoinvestor/id/39730725

Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options 01/13/2026

Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith 01/08/2026

Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Ryan Smith, Link: Link: Link: Link: Link: 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: Copyright of Straight Up Chicago Investor 2026. /episode/index/show/straightupchicagoinvestor/id/39649165

Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm 01/01/2026

Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Jonathan Klemm of Link: Link: Link: 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: Copyright of Straight Up Chicago Investor 2026. /episode/index/show/straightupchicagoinvestor/id/39558860

Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market 12/30/2025

Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1 12/25/2025

Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Alec Greenberg, Link: Link: Link: Link: Link: 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: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39519410

Episode 420: The Chicago Permitting Process with Tom Shallcross 12/18/2025

Episode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley 12/16/2025

Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords 12/11/2025

Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation! Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don’ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and shares horror stories caused by those mistakes! He closes best practices to handle squatters and an outlook on potential changes to the eviction process. 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Zeke McDonald-Lewis, Link: Link: Link: Guest Questions: 03:50 Housing Provider Tip - Plan tenant payment plans to clear balances quickly! 05:51 Intro to our guest, Zeke McDonald-Lewis! 12:25 First step in dealing with a non-paying tenant. 19:54 Next steps after serving a 5-day notice. 34:18 Timelines for the eviction process. 38:36 Top eviction mistakes. 44:43 Eviction horror stories! 47:25 Dealing with squatters. 51:01 Zeke’s outlook on the eviction process! 55:02 What is your competitive advantage? 55:54 One piece of advice for new investors. 56:31 What do you do for fun? 56:59 Good book, podcast, or self development activity that you would recommend? 57:15 Local Network Recommendation? 58:00 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39345050

Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal 12/04/2025

Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings! Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares details on his first 2-unit building in Logan Square and dives deep into top “gotchas” when purchasing 2-4 unit buildings. He closes with a bullish outlook on Chicago particularly the areas surrounding the United Center! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Niko Apostal, Link: Link: Link: Guest Questions: 01:58 Housing Provider Tip - Be sure to appeal property taxes particularly with upcoming reassessments! 03:36 Intro to our guest, Niko Apostal! 08:41 Weathering the storm of the real estate crash! 20:53 Lessons learned and tips for starting a real estate brokerage. 30:25 Investing in a 2-unit in Logan Square. 42:00 Essex 312 vs Essex Realty Group. 48:50 Gotchas when buying a 2-4 unit building! 52:10 Neighborhoods that Niko is bullish on! 60:20 5 Year Outlook on Chicago. 62:24 What is your competitive advantage? 63:11 One piece of advice for new investors. 63:27 What do you do for fun? 63:39 Good book, podcast, or self development activity that you would recommend? 64:04 Local Network Recommendation? 64:57 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39245720

Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants 12/02/2025

Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats 11/27/2025

Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical areas of focus and on understanding risks when developing product that will set the top comparable in a neighborhood. Lawrence provides a great take on his top Chicago neighborhoods for upside and reasoning for why he is bullish. Throughout this episode, Lawrence emphasizes the importance of deeply understanding your market and getting in the game to achieve 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Lawrence Dunning, Link: Link: Link: Link: Guest Questions: 03:01 Housing Provider Tip - Leverage adjustable handrails for an affordable solution to meet compliance requirements! 04:58 Intro to our guest, Lawrence Dunning! 12:27 Lawrence’s business and areas of focus! 16:40 Real estate agent’s value to developers. 26:33 Setting the top comparables in a neighborhood. 35:02 Lawrence’s top emerging neighborhoods! 45:46 Outlook on Chicago’s south side. 52:01 What is your competitive advantage? 53:00 One piece of advice for new investors. 53:47 What do you do for fun? 54:54 Good book, podcast, or self development activity that you would recommend? 56:43 Local Network Recommendation? 57:02 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39166930

Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows 11/20/2025

Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs! Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Mark Ainley of Link: Link: Link: Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements! 04:55 Intro to our guest, Mark Ainley! 05:48 The history of village requirements for rentals. 09:17 Considerations when investing in Schaumburg. 17:27 Insights on permits and associated fees. 21:38 Navigating point of sale inspections in different villages. 31:46 What to know about tax transfer stamps! 35:56 Overview on rental licenses, village inspections, STR licenses, and more! 39:51 Book recommendations from Mark! ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39094090

Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev 11/18/2025

Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons 11/13/2025

Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio. Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Link: Link: Link: Link: Link: Link: Guest Questions: 03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up! 05:03 Intro to our guest, Luke Helliker! 13:19 Luke’s first deal: a 2-unit house hack! 20:18 How to leverage the ADU process. 27:20 Funding an ADU project. 41:09 Navigating investing with your significant other. 43:15 Acquiring a 4-unit building in a competitive market! 58:47 Lessons learned on the 4-unit acquisition. 65:30 Luke’s next investment targets. 66:19 What is your competitive advantage? 67:15 One piece of advice for new investors. 67:59 What do you do for fun? 69:19 Good book, podcast, or self development activity that you would recommend? 70:01 Local Network Recommendation? 70:30 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/39001145

Episode 411: Shawn Good Creates Opportunity with Off Market Deals 11/06/2025

Episode 411: Shawn Good Creates Opportunity with Off Market Deals Shawn Good is a seasoned attorney and real estate investor with vast experience acquiring and stabilizing off-market real estate. Shawn kicks things off by discussing his first few deals which included a condo and an 8-unit building. He shares some funny stories on unfair partnerships he’s been a part of and important points on due diligence when acquiring a property. Shawn explains how joining Collective Genius helped him take his law practice and direct to seller marketing to the next level. He closes with his 5-year plan and hilarious real estate horror 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Shawn Good, Link: Link: Link: Guest Questions: 02:06 Housing Provider Tip - Ensure to have a lease on a departing residence when required for another loan! 04:03 Intro to our guest, Shawn Good! 08:25 Transitioning to an 8-unit building after a condo purchase. 13:38 House hacking and starting a law practice! 21:23 Simple partnership structures. 26:28 Generating off-market deal flow! 36:36 Shawn’s 5 year plan. 46:44 Horror stories! 51:37 What is your competitive advantage? 52:18 One piece of advice for new investors. 53:27 What do you do for fun? 53:50 Good book, podcast, or self development activity that you would recommend? 55:00 Local Network Recommendation? 56:54 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38926205

Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross 11/04/2025

Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman 10/30/2025

Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman Eli Goodman of Illinois Real Estate Buyers gives the complete playbook on dealing directly with sellers to acquire off-market deals! Eli starts with explaining the grind it took to get his wholesaling off the ground! He discusses the right way to communicate with distressed sellers to create win-win scenarios and also throws in a few horror stories. Eli shares the various processes for direct to seller marketing and how he’s achieved success. He closes things to keep in mind when practicing wholesaling in Illinois to mitigate your risk! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Eli Goodman, Link: Link: Link: Link: Guest Questions: 01:42 Housing Provider Tip - Leverage a HELOC on your primary residence for emergencies and to continue scaling! 03:37 Intro to our guest, Eli Goodman! 07:00 Getting a wholesaling business off the ground. 11:42 How to communicate directly with sellers! 17:18 Tactical tips on direct to seller marketing. 25:08 Building a list of cash buyers. 34:33 Outlook on Eli’s wholesaling business. 37:07 Challenges of wholesaling in Illinois. 44:19 What is your competitive advantage? 44:45 One piece of advice for new investors. 45:00 What do you do for fun? 45:12 Good book, podcast, or self development activity that you would recommend? 45:29 Local Network Recommendation? 46:05 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38833665

Episode 408: Chicago Suburb Land Development with Jim Paul 10/23/2025

Episode 408: Chicago Suburb Land Development with Jim Paul Jim Paul, Director of the ALPS Group, has over 2 decades of experience in land development and receivership. Jim jumps right in by discussing an early 21-acre land development deal and the hurdles he dealt with there! He breaks down his Tuscan Hills and Canterbury Lakes projects - residential developments in Will County, IL. Jim explains how to get creative with land development design and how to finance these projects. Throughout the episode, Jim repeats the importance of due diligence to mitigate risks and protect yourself and your investors! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: , ALPS Group | Call Jim: | Email Jim: Link: Link: Guest Questions: 02:21 Housing Provider Tip - Considering replacing older appliances instead of spending on repairs! 03:25 Intro to our guest, Jim Paul! 05:40 Developing a 21-acre property with limited experience! 14:28 How to source land deals. 24:27 Getting creative with land development! 29:02 Financing land development. 34:03 Lessons learned from 20 years of experience. 35:45 The ins and outs of receivership. 52:22 Jim’s plan for the next 5 years! 55:31 What is your competitive advantage? 57:25 One piece of advice for new investors. 58:41 What do you do for fun? 59:00 Good book, podcast, or self development activity that you would recommend? 60:50 Local Network Recommendation? 62:07 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38744125

Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago 10/21/2025

Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa 10/16/2025

Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa Moises Correa, Principal of Proximo Equity Group, leads a team that specializes in value-add multifamily real estate across the Midwest. Moises provides the ins and outs of his first couple house hacks in Avondale and how he burned the boats and left his W2 job after the first one! He explains how he formed partnerships to purchase a large multifamily building in Louisville, KY and gets granular on the due diligence process. Moises shares great insights on capital raising and structuring partnerships to be able to take down these large acquisitions. He breaks down how he leveraged a broker relationship to acquire a deal in Fort Wayne, IN well below market value. This episode showcases how building a team and fostering relationships can truly pay dividends 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Moises Correa, Link: Link: Guest Questions: 02:50 Housing Provider Tip - Understand your leases entirely to avoid legal issues. 04:44 Intro to our guest, Moises Correa! 09:05 Early lessons learned in REI! 14:43 Moises’ second acquisition. 22:03 Jumping into a larger deal in Louisville! 34:02 Capital raising and structuring partnerships! 45:45 Horror stories from Louisville deals. 49:46 Investing in Fort Wayne, IN! 57:48 What is your competitive advantage? 58:18 One piece of advice for new investors. 59:21 What do you do for fun? 59:54 Good book, podcast, or self development activity that you would recommend? 60:09 Local Network Recommendation? 60:28 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38596460

Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal 10/09/2025

Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal Joe Smazal, Senior Managing Partner of Interra Realty, has over a decade of experience selling mid-market apartment buildings and recently surpassed $1 Billion in transaction volume! Joe kicks things off by sharing the genesis and overview of his “Real Estate Chicago Style Podcast”! He reflects on his career’s progression and highlights that have led him to crossing the $1 billion mark in total transaction volume. Joe dives deep on the market trends for Chicago’s North Side including prime neighborhoods like Lincoln Park and Lakeview. Joe closes with takeaways from some recent personal transactions and provides an optimistic outlook on the Chicago Real Estate 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Joe Smazal, Link: Link: Link: Link: Link: Link: Guest Questions 02:38 Housing Provider Tip - Understand rules and regulations around security deposits! 05:00 Intro to our guest, Joe Smazal! 07:10 Joe’s Real Estate Chicago Style Podcast! 15:25 Joe’s path to $1 Billion of Commercial RE sales. 23:11 Chicago market trends in 2025. 31:27 Navigating the Predominance of the Block (606) Ordinance. 49:50 Joe’s 5-year plan. 54:57 The outlook on Chicago! 58:29 What is your competitive advantage? 58:53 One piece of advice for new investors. 59:19 What do you do for fun? 59:51 Good book, podcast, or self development activity that you would recommend? 60:55 Local Network Recommendation? 62:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38516560

Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo 10/07/2025

Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski 10/02/2025

Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski Lantz Kurzawinski, Marketing Specialist for the Straight Up Chicago Investor Podcast, tells his story of grinding to succeed in real estate at an early age. Lantz explains how he recognized his entrepreneurial spirit at an early age and decided to dive into real estate. He shares his experience as a leasing agent and how that led him to discover his enjoyment for getting his hands dirty. Lantz gets granular on partnering on a few BRRRR deals and the value he brought to the partnership despite not having much liquidity! He shares insights on closing a house hack deal with a hilarious story about living in a “work in progress” basement apartment! Lantz demonstrates how hard work and bringing value to others is very much the key to succeeding in REI like other areas of life! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Lantz Kurzawinksi, Link: Link: Link: Link: Guest Questions 02:49 Housing Provider Tip - Consider giving renters storage unit options to maximize your units’ appeal. 04:39 Intro to our guest, Lantz Kurzawinski! 12:56 Starting off as a leasing agent. 18:38 Lantz’s first deal! 23:06 Cranking through another BRRRR project and structuring partnerships. 28:00 House hacking in Jefferson Park! 40:30 Taking down deals in Itasca and Downers Grove. 46:51 What is your competitive advantage? 47:20 One piece of advice for new investors. 48:22 What do you do for fun? 48:28 Good book, podcast, or self development activity that you would recommend? 49:10 Local Network Recommendation? 49:41 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38411825

Episode 402: Looking At Chicago Investing Differently with Jason Wagner 09/25/2025

Episode 402: Looking At Chicago Investing Differently with Jason Wagner Jason shares why he chose to invest in Chicago’s northwest side and how he’s achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset’s ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors! 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Jason Wagner, Link: Link: Link: Link: Link: Guest Questions 02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers! 04:52 Intro to our guest, Jason Wagner! 10:53 Emerging neighborhoods and creative strategies for cash flow! 28:42 Ins and outs of assumable loans. 36:06 Insights on VA loan assumptions. 38:03 The background on Greystone Realty. 42:56 Housing market takeaways from the Wagner Report! 45:58 Opportunities in Arlington Heights. 50:26 Best of advice for aspiring real estate investors. 52:42 What is your competitive advantage? 53:07 One piece of advice for new investors. 53:20 What do you do for fun? 54:28 Good book, podcast, or self development activity that you would recommend? 56:19 Local Network Recommendation? 57:11 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38343230

Episode 401: Interest Rates Are Coming Down According to Chris Puleo 09/23/2025

Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio 09/18/2025

Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio Kevin Rocio, founder of ROC Advisory Group, is an award winning commercial real estate broker, mentor, and investor. Kevin shares how he built a business and sphere of influence in the mortgage lending industry. He discusses his start in commercial real estate and gets granular on various valuation metrics. Kevin talks about the rapid growth of his business during and after the pandemic. He closes with explaining the importance of building a great reputation to set yourself up for success in this relationship-based 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: Email the Show: Properties for Sale on the North Side? We want to buy them. Email: Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: ============= Guest: Kevin Rocio, Link: Link: Link: Link: Guest Questions 04:09 Housing Provider Tip - Let insurance representatives know about property improvements to reduce your premium! 05:50 Intro to our guest, Kevin Rocio! 14:45 Transitioning out of mortgage lending after 17 years. 20:46 Starting in real estate brokerage in 2009. 33:16 Utilizing GRM for valuations. 34:51 Kevin’s business through and post COVID. 48:31 How to find a mentor! 52:32 Importance of marketing and building a reputation. 55:05 What is your competitive advantage? 55:32 One piece of advice for new investors. 56:08 What do you do for fun? 56:50 Good book, podcast, or self development activity that you would recommend? 58:18 Local Network Recommendation? 59:09 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025. /episode/index/show/straightupchicagoinvestor/id/38244510

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