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 381: How Chicago’s Powerhouse Lender Renovo Financial Was Built with Kevin Werner 06/19/2025

Episode 381: How Chicago’s Powerhouse Lender Renovo Financial Was Built with Kevin Werner 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: ============= Kevin Werner, CEO of Renovo Financial, has over 20 years of experience building and scaling successful lending companies! Kevin discusses his start in the lending business including his first company that did not survive the Great Financial Crisis. He shares lessons learned from lending through the Housing Crash and how those insights coupled with great relationships lead to the inception of Renovo Financial. Kevin gives the philosophy that has led to Renovo’s explosive growth the last decade including thriving through the uncertainty of COVID. Throughout the show, Kevin drops powerful outlooks on business, customer service, and relationships that you’ll want to remember and implement! 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: Guest: Kevin Werner, Link: Link: Link: Guest Questions 01:51 Housing Provider Tip - Understand the power of being decisive and taking action! 03:18 Intro to our guest, Kevin Werner! 10:44 Getting a loan business off the ground in the 90s. 15:28 Lending through the Housing Crash! 34:21 The business model of lending business. 45:27 Renovo’s explosive growth through COVID into 2025! 60:18 Kevin’s parenting philosophy and outlook on Chicago! 63:24 What is your competitive advantage? 64:20 One piece of advice for new investors. 64:53 What do you do for fun? 66:04 Good book, podcast, or self development activity that you would recommend? 66:53 Local Network Recommendation? 68:38 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/37063895

Episode 380: Innovation in Modular Housing With Rory Rubin 06/12/2025

Episode 380: Innovation in Modular Housing With Rory Rubin 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: ============= Rory Rubin shows us first hand how S.I. Container Builds is bringing high quality, low maintenance steel dwellings to help solve the housing supply shortage! Rory jumps right with a recap of modular housing and the advantages it brings over traditional brick and wood housing structures. She shares lessons learned after 7 successful years of leading S.I. Container Builds. Our video viewers get to see an awesome container building constructed for Navy Pier and Rory breaks down some complex projects. This episode showcases the innovation within modular housing and Rory makes it clear that container builds are quality housing stock that everyone should strongly consider! 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: Guest: Rory Rubin, Link: Link: Link: Guest Questions 03:11 Housing Provider Tip - Communicate your move-out procedure and expectations to your tenants! 04:41 Intro to our guest, Rory Rubin from SI Container Builds! 06:46 Recapping the 101 on container builds! 09:45 Advantages of container builds. 17:30 Lessons learned from 7 years of modular building! 21:30 Complex container builds! 25:25 Navy Pier Container and Affordable Housing! 28:09 What is your competitive advantage? 28:33 One piece of advice for new investors. 29:21 What do you do for fun? 29:33 Good book, podcast, or self development activity that you would recommend? 29:55 Local Network Recommendation? 30:21 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/36962625

Episode 379: Preparing Your Property To Add an ADU 06/10/2025

Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds 06/05/2025

Episode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds 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: ============= Wonderful Togbey joins us to explain how he’s grinded to build a rental portfolio of 20 doors and is actively scaling! Wonderful shares his start in REI back in Omaha, Nebraska. He breaks down a deal in Bronzeville that closed right at the onset of COVID that came equipped with non-paying tenants! Wonderful reflects on lessons learned from gut renovations including considerations on layouts to maximize rents. He has multiple examples of pivoting while under, and even getting a second job to get deals done. This episode is a motivating one with countless stories showcasing perseverance and grit. 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: Guest: Link: Link: Link: Guest Questions 02:17 Housing Provider Tip - Leverage Google Earth and other tools for measurements and floor plans! 03:55 Intro to our guest, Wonderful Togbey! 09:21 Starting real estate investing in Omaha, NE. 13:40 Challenging Bronzeville Deal with COVID looming! 19:51 The power of long term investing and dealing with non-paying tenants. 30:16 Wonderful’s first gut rehab project and buying another property simultaneously! 36:38 Cultivating perseverance in real estate. 41:56 Lessons learned from redeveloping a building. 47:41 Wonderful’s long term investing goals. 50:36 Management systems for small investors. 52:14 What is your competitive advantage? 52:50 One piece of advice for new investors. 53:34 What do you do for fun? 53:45 Good book, podcast, or self development activity that you would recommend? 54:23 Local Network Recommendation? 54:52 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/36855900

Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker 05/29/2025

Episode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker 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: ============= Daniel Baker, owner of Teton Properties, explains how he’s built a portfolio with strategic house hacks and value-add renovations. Daniel discusses his move from Memphis to Chicago to get started in real estate. He shares some hilarious stories on househack value-add projects and getting extremely gritty to get projects to the finish line. He then breaks down a deal that closed right at the onset of COVID in 2020. Throughout this episode, Daniel gives numerous examples of how getting scrappy and persevering can be a competitive advantage that pays huge dividends. 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: Guest: , Teton Properties Link: Link: Link: Link: Guest Questions 02:08 Housing Provider Tip - Consider making professional carpet cleaning a move-out requirement for tenants! 04:23 Intro to our guest, Daniel Baker! 07:35 Getting started in real estate with Marcus & Millichap. 18:46 Purchasing a Lincoln Square 4-Flat after a few house hacks! 26:48 Daniel’s top lessons learned after his first few projects! 29:41 Jumping into a deal with COVID looming. 39:33 Closing a deal while getting laid off! 44:40 What’s next for Daniel? 47:48 Daniel’s outlook on Chicago! 50:43 What is your competitive advantage? 51:11 One piece of advice for new investors. 51:30 What do you do for fun? 51:51 Good book, podcast, or self development activity that you would recommend? 52:22 Local Network Recommendation? 49:10 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/36758150

Episode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property 05/27/2025

Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez 05/22/2025

Episode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez 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: ============= Real Estate Nate shares how he has accumulated 26-units with healthy cash flow all while having a demanding W2 job! Nate shares lessons learned from his first few deals and compares small vs large multifamily buildings. He explains how he and his wife leverage their high-income W2 jobs to propel their real estate investments and hedge associated risks. Nate dives into his consulting business involving CRM system implementation. Nate closes with tips on financing 5+ unit buildings and emphasizes the importance of building a great team to set yourself up for REI 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: Guest: Nate Fernandez, Link: Link: Link: Link: Link: Link: Guest Questions 02:51 Housing Provider Tip - Power through difficult deals and keep the end goal in mind! 04:48 Intro to our guest, Nate Fernandez! 09:06 Lessons learned from Nate’s first deal! 16:17 Comparing 2-4 unit vs 5+ unit buildings. 20:16 Hedging risk with proper planning. 23:33 Setting up a property management system. 27:02 Nate’s system implementation consulting business and areas of focus. 30:43 Navigating pre-sale inspections. 35:57 Nate’s goals by 40! 38:05 Leveraging a W2 job to propel real estate investments! 40:55 How to finance 5+ unit buildings. 45:11 What is your competitive advantage? 45:53 One piece of advice for new investors. 46:19 What do you do for fun? 46:57 Good book, podcast, or self development activity that you would recommend? 47:50 Local Network Recommendation? 49:10 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/36662975

Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver 05/15/2025

Episode 374: Taking On Opportunity In Chicago’s Toughest Neighborhoods with Corey Oliver 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: ============= Corey Oliver, CEO of Strength in Management, is back three years later to share additional insights on managing in C/D neighborhoods. Corey starts by discussing recent compression of cap rates and investment financials in Chicago C/D class neighborhoods. He gets granular on the process for placing and managing CHA tenants. Corey breaks down how he sets investment return expectations for out of state investors looking to invest in lower income neighborhoods. Corey closes with exciting news about his upcoming development project which includes city grants and tax credits! 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: Guest: , Link: Link: Guest Questions 02:38 Housing Provider Tip - Understand the risks of hydro-jetting old sewer lines! 04:07 Intro to our guest, Corey Oliver! 09:49 Cap rates and expense ratios in challenging neighborhoods! 15:16 Rent increase on subsidized housing tenants. 17:55 Managing CHA tenants. 32:00 Setting expectations on C/D class investments! 42:18 Corey’s upcoming development project! 61:21 What is your competitive advantage? 61:37 One piece of advice for new investors. 62:02 What do you do for fun? 62:43 Good book, podcast, or self development activity that you would recommend? 63:48 Local Network Recommendation? 64:08 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/36573035

Episode 373: A New Option to Fund Renovations For Chicago 2-4 Properties 05/13/2025

Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell 05/08/2025

Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell 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: ============= Kevin Schnell of Concord Capital has amassed a portfolio of over 400 rental units and has vast experience repositioning multi-family and mixed-use real estate investments! Kevin hits the ground running with how he grinded early in his real estate career to learn his markets and efficiently prospect to generate deal flow. He discussed the valuable knowledge he gained while working with MO2 Properties, a Chicago-based rental property owner and operator. Kevin describes the journey of leaving MO2 Properties to start his own investment company. He closes the show with advice on adaptive reuse projects and motivating words on why Chicago is the place to be for 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: Guest: Kevin Schnell, Link: Link: Link: Guest Questions 03:05 Housing Provider Tip - Understand tenant chargebacks to protect yourself from tenant damages! 04:39 Intro to our guest, Kevin Schnell! 07:14 How to learn a market and prospecting. 15:57 Kevin’s transition to MO2 Properties! 23:18 Strategies for cold calling sellers. 32:47 Leaving MO2 to start an investment business! 36:42 Kevin’s current focus. 41:44 Considerations on adaptive reuse projects! 44:35 Why Kevin is doubling down on Chicago! 48:55 What is your competitive advantage? 49:18 One piece of advice for new investors. 50:12 What do you do for fun? 50:50 Good book, podcast, or self development activity that you would recommend? 51:43 Local Network Recommendation? 52:05 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/36480535

Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan 05/01/2025

Episode 370: How The Current 2025 Lending Market Differs From Previous Year 04/29/2025

Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson 04/24/2025

Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event) 04/17/2025

Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg 04/15/2025

Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma 04/10/2025

Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals! Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creative” deals including one deal where he was able to close on a property minutes before it would have been foreclosed on. Jeffrey explains how he’s gotten into bigger deals including a multifamily syndication and brokering a warehouse space that resulted in a six-figure commission! Throughout the show, Jeffrey is able to eloquently convey his approach to real estate and life which revolves around enjoying the process and being grateful for the present moment! 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: Guest: , Keller Williams Preferred Realty Link: Link: Link: Link: Link: Guest Questions 02:53 Housing Provider Tip - Keep a bag of ice melt at your properties in the event of unforeseen slippery conditions! 04:27 Intro to our guest, Jeffrey Ma! 12:10 Gaining momentum in real estate and getting into wholesaling! 19:11 Jeffrey’s journey to creative deals. 25:18 Case studies of “cool” deals! 29:44 Jeffrey’s most “unconventional” deal to date. 36:46 Getting into bigger deals including a 6-figure commission! 40:06 The Origin Story of Jeffrey’s and his partner Eli’s meetup. 43:02 What’s next for Jeffrey?! 48:35 What is your competitive advantage? 49:00 One piece of advice for new investors. 49:23 What do you do for fun? 49:58 Good book, podcast, or self development activity that you would recommend? 51:21 Local Network Recommendation? 51:42 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/36070065

Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon 04/03/2025

Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman 04/01/2025

Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren 03/27/2025

Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry 03/20/2025

Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance 03/18/2025

Episode 360: Don’t Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney 03/13/2025

Episode 359: 2025 Cook County Evictions with Tom Raleigh 03/06/2025

Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio 03/04/2025

Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network 02/27/2025

Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro 02/20/2025

Episode 355: How To Optimize Tax Deductions as a Househacker 02/18/2025

Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon 02/13/2025

Episode 353: From Near Death Experience, to Disciplined Financial Freedom with Mike Bednarz 02/06/2025

Episode 353: From Near Death Experience, to Disciplined Financial Freedom with Mike Bednarz Mike Bednarz, an accomplished real estate investor and HVAC business owner, joins us to share his inspiring trajectory of growing a real estate portfolio and overcoming a scary accident! Mike explains how he lived frugally to save a down payment and buy his first multifamily investment property in Edison Park. He discusses the discipline he used to acquire his second property and how he found a niche in mixed-use properties with leasing up local retail spaces. Mike shares a life changing incident where he fell off a ladder while working for his HVAC company that resulted in life threatening injuries. He breaks down his recovery despite doctors doubting that it was possible and bouncing back stronger than ever. This is the definition of an inspirational conversation around discipline and grit that you will not 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: Email the Show: Guest: , Housing Opportunity Development Corporation (HODC) Link: Link: Guest Questions 05:09 Housing Provider Tip - Understand the Illinois Landlord Retaliation Act! 06:51 Intro to our guest, Mike Bednarz! 15:40 Jumping into a 6-unit after a house hack! 21:32 Finding a niche in mixed-use buildings. 23:36 Mike’s scary accident. 31:58 Mike’s history of discipline. 35:47 What’s next for Mike and the meaning of purpose! 43:35 What is your competitive advantage? 44:57 One piece of advice for new investors. 45:37 What do you do for fun? 46:20 Good book, podcast, or self development activity that you would recommend? 47:42 Local Network Recommendation? 48:46 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/35170320

Episode 352: Current Issues The NBOA is Fighting with Mike Glasser 02/04/2025

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