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 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White 09/11/2025

Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White 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: ============= Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI! Micah starts by explaining the ins and outs of his first couple house hacks in Logan Square and North Lawndale. He provides great pointers on proper due diligence to mitigate risk on an investment. Micah shares a hilarious DIY story; moral of the story, hire a professional! He closes with valuable insights on structuring partnerships and building a track record to attract 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: Guest: , Brick by Brick Blueprint Link: Link: Link: Link: Link: Guest Questions 02:22 Housing Provider Tip - Remove window AC units to improve heat efficiency this winter! 03:45 Intro to our guest, Micah White! 14:31 Micah’s start in REI! 22:12 Due diligence on your first deal. 26:58 Bumping rents and stabilizing a building. 31:28 The DIY wax ring story! 37:27 Micah’s North Lawndale deal. 44:38 Structuring partnerships with investors. 53:20 Reputation building to attract investors. 57:22 What is your competitive advantage? 58:01 One piece of advice for new investors. 58:35 What do you do for fun? 59:45 Good book, podcast, or self development activity that you would recommend? 61:56 Local Network Recommendation? 62:17 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/38169735

Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca 09/04/2025

Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca 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: ============= Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly real estate agent! Paul jumps right into the nitty gritty of his first couple house hack deals! He gives tips on getting off the ground as a new real estate agent and the 101 on Chicago non-conforming units. Paul shares how he handled various troublesome tenants and provides his take on emerging neighborhoods where he’s investing! Throughout the episode, Paul demonstrates how focus and taking action have been keys to his investing 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: Paul de Luca, Link: Link: Link: Link: Link: Link: Guest Questions 03:25 Housing Provider Tip - Consider the ROI on central HVAC! 05:08 Intro to our guest, Paul de Luca! 10:52 Reflecting on Paul’s first house hack. 13:45 Getting into house hack #2! 21:20 Getting started as a new real estate agent. 25:32 Valuing non-conforming units. 31:33 Handling problem tenants. 36:18 Neighborhood guide for investors! 42:35 Paul’s 5 year outlook! 48:48 What is your competitive advantage? 49:23 One piece of advice for new investors. 49:50 What do you do for fun? 50:00 Good book, podcast, or self development activity that you would recommend? 50:31 Local Network Recommendation? 50:55 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/38081735

Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property? 09/02/2025

Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci 08/28/2025

Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci 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: ============= Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand! Fernando explains his marketing strategy to optimize deal flow despite the low inventory environment. He delves deep into the underwriting and feasibility studies performed on self storage investments to maximize returns. Fernando provides the 101 on various financing options and repositioning strategies for self storage investments. He closes with a motivating 5-year outlook including a detailed plan to reach financial independence! 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: Fernando Angelucci, Link: Link: Link: Link: Guest Questions 01:49 Housing Provider Tip - Be sure to perform maintenance on AC units after a long summer! 03:25 Intro to our guest, Fernando Angelucci! 06:41 Growing a portfolio in a low inventory market! 12:10 Feasibility studies on self storage projects. 16:44 Building a self storage investment team! 21:56 Financing self storage deals. 37:33 Repositioning a self storage investment. 47:57 Obtaining special use permits. 52:01 Ideal self storage projects! 55:23 Fernando’s 5-year outlook. 60:26 What is your competitive advantage? 62:55 One piece of advice for new investors. 63:32 What do you do for fun? 64:14 Good book, podcast, or self development activity that you would recommend? 64:48 Local Network Recommendation? 65:53 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/37979885

Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew 08/21/2025

Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew 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: ============= Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago’s north side! Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He talks about the importance of knowing your market to accurately project rents and pro-formas. Max gets granular on leasing including tips for screening out fraudulent applicants and best marketing practices. Throughout the episode, Max emphasizes the importance of having great relationships with tenants and being an expert in your geographical area of focus as keys 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: Guests: Max Motew, Link: Link: Link: Guest Questions 02:05 Housing Provider Tip - Take action and jump into real estate! 03:23 Intro to our guest, Max Motew! 07:10 Considerations on landmarked buildings. 14:04 Making deals “pencil” in today’s market. 23:36 Projecting rents and pro-formas! 32:55 Optimizing lease renewals. 43:15 Common leasing mistakes to avoid! 50:08 Screening best practices. 55:57 Up and coming Chicago neighborhoods! 61:18 What is your competitive advantage? 62:25 One piece of advice for new investors. 62:48 What do you do for fun? 63:30 Good book, podcast, or self development activity that you would recommend? 64:09 Local Network Recommendation? 64:37 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/37881090

Episode 394: The Legal Nuances of Different Real Estate Partnership Structures 08/19/2025

Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy 08/14/2025

Episode 393: Chicago Veterans’ Guide to Real Estate Success with DuBois Toy 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: ============= DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits! DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He breaks down the rent-by-the-room strategy as a tool to maximize ROI. DuBois dives deep on VA loans, tax exemptions, and various other powerful real estate tools available to veterans! From leveraging AI for deal searching to veteran resources, this show is full of invaluable insights 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: Email the Show: Guests: DuBois Toy, Link: Link: Link: Link: Link: Link: Guest Questions 02:17 Housing Provider Tip - Understand rental license and inspection requirements in the suburbs! 04:00 Intro to our guest, DuBois Toy! 08:31 The future of tech in real estate! 15:49 DuBois’ background and start in real estate. 24:27 House hacking and dealing with an eviction in Oak Park! 29:27 Leveraging rent by the room strategy. 35:58 Educating veterans on VA loan benefits! 41:26 Revealing DuBois’ growth strategy! 49:09 DuBois’ bullish outlook on Chicago! 54:23 What is your competitive advantage? 55:03 One piece of advice for new investors. 55:41 What do you do for fun? 56:14 Good book, podcast, or self development activity that you would recommend? 57:20 Local Network Recommendation? 58:38 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/37803205

Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars 08/07/2025

Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars 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 Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003. Cost Seg Kev starts by reviewing the 101 on cost segregation and how it can be used to offset your tax liability. He dives into the benefits of real estate professional status and recent tax code changes by the presidential administration. He also touches on frequently asked questions on cost segregation studies and closes with how he built his business and reputation! 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: Guests: Kevin Cawley, Link: Link: Link: Link: Guest Questions 02:46 Housing Provider Tip - Go above and beyond to acknowledge tenants after management mistakes. 05:00 Intro to our guest, Cost Seg Kev! 05:43 The 101 on Cost Segregation. 11:37 The benefits of real estate professional status! 25:42 Recent changes to depreciation rules. 32:15 Technical side of cost segregation! 34:23 Cost Seg on smaller properties. 43:43 What is your competitive advantage? 44:42 One piece of advice for new investors. 46:00 What do you do for fun? 46:37 Good book, podcast, or self development activity that you would recommend? 47:52 Local Network Recommendation? 48:55 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/37705895

Episode 391: Do You Have a Business Continuation Plan? 08/05/2025

Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims 07/31/2025

Episode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims 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: ============= Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55 years! Mitch starts by explaining the services rendered by insurance adjusters. He breaks down how investors can set themselves up for success with insurance claims and provides tactical steps for handling disastrous situations at properties. Mitch dives deep on insurance coverages, how investors can best protect themselves, and shares some wild insurance stories! This show is full of valuable insurance insights that you will want to put into practice! 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: Guests: Mitch Schoeneman, | Link: Guest Questions 03:14 Housing Provider Tip - Home insurance considerations to improve coverage and pricing! 04:56 Intro to our guest, Mitch Schoeonemen! 08:33 The value of insurance adjusters. 15:57 How investors can prepare for successful insurance claims. 21:17 Properly handling emergency situations at properties! 37:15 General timelines for insurance payouts. 45:00 Wild insurance stories! 53:39 What is your competitive advantage? 54:01 One piece of advice for new investors. 54:08 What do you do for fun? 54:59 Good book, podcast, or self development activity that you would recommend? 55:32 Local Network Recommendation? 55:53 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/37611270

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec 07/24/2025

Episode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec 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: ============= Sebastian Mysliwiec, founder of The Dream Rentals, explains how he’s built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits! Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team’s growth strategy. 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: Guests: Sebastian Mysliwiec, Link: Link: Link: Guest Questions 01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence! 04:25 Intro to our guest, Sebastian Mysliwiec! 08:31 Defining AirBnB arbitrage. 13:28 Underwriting basics of short-term rentals (STRs)! 20:10 Listing platforms for STRs. 26:09 Managing STR seasonality in Chicago to optimize profit. 35:36 STR Marketing Tips! 45:45 AirBnB Horror Story! 47:46 Top STR amenities. 49:23 Mid-Term Rental analysis and expanding to other markets! 55:13 Refinancing STR properties. 56:47 What is your competitive advantage? 57:15 One piece of advice for new investors. 57:42 What do you do for fun? 58:25. Good book, podcast, or self development activity that you would recommend? 58:54 Local Network Recommendation? 59:29 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/37534680

Episode 388: NBOA 2025 Summer Soiree Update 07/22/2025

Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz 07/17/2025

Episode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz 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: ============= Alex Diaz explains how he left his day job as a barber to successfully flip and wholesale real estate for a living at 24 years of age! Alex starts by sharing how he made the jump from being a barber to wholesaling real estate. He explains how he acquired his first property; a househack sourced off-market! Alex provides tactical advice on marketing directly to sellers to create deal flow. He talks about lessons learned from flipping and gets granular on the real estate market in Aurora and the surrounding suburbs. This is another motivating show with an investor thriving at a young age! 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: Alex Diaz, Link: Link: Link: Guest Questions 03:16 Housing Provider Tip - Maintain and understand misusage of water hose spigots! 05:09 Intro to our guest, Alex Diaz! 10:38 Alex’s first house hack sourced off-market! 14:24 Jumping into wholesaling and direct-to-seller marketing. 26:20 Marketing strategy and the 101 on Montgomery, IL. 29:11 Benefits of being around like-minded investors. 35:10 Lessons learned from flipping! 39:24 Alex’s geographic areas of focus. 44:06 What is your competitive advantage? 44:31 One piece of advice for new investors. 45:14 What do you do for fun? 45:31 Good book, podcast, or self development activity that you would recommend? 46:04 Local Network Recommendation? 46:23 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/37436610

Episode 386: How to Invest in DuPage County with Katie and Rob Hayes 07/10/2025

Episode 386: How to Invest in DuPage County with Katie and Rob Hayes 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: ============= Katie and Rob Hayes are investors and realtors with nearly 2 decades of experience acquiring and managing investment properties! The duo starts by sharing their background including investing in Florida before transitioning to the Chicago Western Suburbs. They share lessons learned from investing in lower cost areas and why they pivoted to higher class assets. Rob and Katie share golden nuggets on marketing to owners for deal flow and on operating short-term rentals. They close out with a positive outlet on Downer’s Grove and why investors should be considering 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: Guests: Katie and Rob Hayes, Link: Link: Link: Guest Questions 03:03 Housing Provider Tip - Utilize Starbucks gift cards to easily express gratitude towards tenants and vendors! 04:33 Intro to our guests, Katie and Rob Hayes! 09:54 Jumping from Florida to local investments! 14:30 Considerations when investing in lower price point areas. 17:45 Investments leading up to the housing crash. 23:47 Getting a real estate license during the housing crash. 29:05 Creating deal flow in a low inventory market. 34:40 Representing and adding value to buyers in this market. 39:17 Dialing back acquisitions and strategizing for retirement! 44:35 Short-term rentals in Chicago suburbs. 54:40 Advice for couples who invest together! 57:15 What is your competitive advantage? 58:31 One piece of advice for new investors. 59:45 What do you do for fun? 60:34 Good book, podcast, or self development activity that you would recommend? 61:42 Local Network Recommendation? 63:05 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/37356015

Episode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter 07/08/2025

Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton 07/03/2025

Episode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton 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: ============= Jake Clopton, President of Clopton Capital, has successfully been running his commercial lending business for over 17 years. Jake shares how he grinded early in his career to get off the ground, and emphasizes the value of cold calling. He explains the different types of interest rates and provides the current state of rates. Jake speaks about macro-level economics including the stagflationary environment in today’s market. In typical SUCI fashion, he closes out with 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: Guest: Jake Clopton, Link: Link: Link: Link: Guest Questions 02:07 Housing Provider Tip - Understand how to prioritize emergency work orders. 04:10 Intro to our guest, Jake Clopton! 12:20 Surviving as a lender during the real estate crash. 19:20 Jake’s “tipping point” deal! 20:21 The state of interest rates. 28:56 Rates on residential real estate. 34:04 Jake’s predictions on rates and the RE market! 41:53 The 101 on Stagflation. 43:50 Jake’s bullish remarks on Chicago! 48:05 What is your competitive advantage? 48:32 One piece of advice for new investors. 49:06 What do you do for fun? 49:17 Good book, podcast, or self development activity that you would recommend? 50:06 Local Network Recommendation? 51:40 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/37267980

Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib 06/26/2025

Episode 383: From Chemist to Chicago’s “Bow Tie” Attorney w/Mahmoud Faisal Elkhatib 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: ============= Mahmoud Faisal Elkhatib is an attorney with vast experience in real estate transactions, development, and litigation allowing him to bring huge value to his clients. Mahmoud gives his back story including time in the laboratory as a chemist and starting various businesses prior to landing into his current career as an attorney! He breaks down foreclosure defense and how he is going to bat for his clients. Mahmoud explains the roles of attorneys and Title Company personnel in a real estate transaction and how his unique fee structure allows his clients to save on fees. Throughout the show, Mahmoud conveys the importance of having a knowledgeable attorney in your corner in any real estate transaction! 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: Mahmoud Faisal Elkhatib, Link: Link: Link: Link: Guest Questions 01:54 Housing Provider Tip - Understand new rules around HVAC to strategically maintain and repair systems! 03:18 Intro to our guest, Mahmoud Faisal Elkhatib! 06:40 How do foreclosure defense firms work? 10:33 Jumping to a new career despite being established in another career! 24:00 Breaking down the roles of Attorneys and Title Companies. 32:27 Mahmoud’s unique attorney fee structure. 38:58 Wild attorney stories! 49:05 Mahmoud’s next 5 years! 56:05 What is your competitive advantage? 56:23 One piece of advice for new investors. 57:00 What do you do for fun? 57:32 Good book, podcast, or self development activity that you would recommend? 58:17 Local Network Recommendation? 58:58 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/37154315

Episode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago 06/24/2025

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

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