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.
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Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan
05/01/2025
Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan
Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit property in McHenry. Michael gets granular on how providing top tier service in leasing allowed him to get referral business which led to the creation of his team, the REKAP Group. Throughout the show, Micheal emphasizes the importance of a strong work ethic and transparency to gain the trust of potential clients and propel your business’ growth. 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: Michael Kaplan, Link: Link: Guest Questions 03:31 Housing Provider Tip - Keep space heaters handy to be prepared for No Heat situations in winter! 05:00 Intro to our guest, Michael Kaplan! 12:13 Grinding as a newly licensed broker. 25:05 The mindset to start investing in real estate! 31:37 Micheal’s first investment in McHenry. 37:47 Starting the REKAP Group! 42:53 What would Michael change in his RE journey so far? 46:14 What is your competitive advantage? 47:12 One piece of advice for new investors. 48:17 What do you do for fun? 49:24 Good book, podcast, or self development activity that you would recommend? 50:26 Local Network Recommendation? 50:43 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 370: How The Current 2025 Lending Market Differs From Previous Year
04/29/2025
Episode 370: How The Current 2025 Lending Market Differs From Previous Year
What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= 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: Eric Workman of Link: Link: B ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson
04/24/2025
Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson
Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple real estate deals including a FHA 203k loan and an intense story about a drive-by shooting at one of his properties! Erik discusses how he raised money to start an innovative, self-pour Tap Room business and emphasizes the importance of building a track record to raise money. He shares keys to growth in real estate and explains how he runs his businesses all while traveling across the world on a regular basis! 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: Erik Swanson, Link: Link: Guest Questions 04:24 Intro to our guest, Erik Swanson! 09:58 Transitioning from the music industry to real estate! 15:28 Drive-by shooting at Erik’s 5-unit building. 18:16 Lessons learned from rehab projects. 20:35 Starting a self pour tap room during COVID! 30:11 Erik’s keys to explosive growth in real estate. 37:36 Reputation building to raise money. 41:57 What’s next for Erik?! 49:12 What is your competitive advantage? 49:50 One piece of advice for new investors. 50:36 What do you do for fun? 50:50 Good book, podcast, or self development activity that you would recommend? 51:33 Local Network Recommendation? 52:23 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)
04/17/2025
Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)
Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily 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: Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360 Link: Link: Link: Link: Guest Questions 00:30 The State of Chicago’s NW Side Commercial Real Estate. 04:33 Leasing trends and strategies! 10:18 Dealing with evictions in today’s market. 17:17 Who is transacting in multifamily real estate in Chicago? 20:58 The evolution of the tenant pool and the market in Chicago. 24:53 Rapid fire Chicago real estate questions! ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg
04/15/2025
Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg
How do I incentivize and optimize renewals? ============= 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: Jeff Weinberg, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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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.
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Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon
04/03/2025
Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon
Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio! Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that involved getting caught doing construction without a permit and going significantly over budget! Wyatt explains the issues that arise from lack of liquidity even for high networth individuals. Throughout the episode, Wyatt drops powerful insights on mentorship, staying disciplined, and starting with the end in mind! 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: Link: Link: Guest Questions 03:30 Housing Provider Tip - Understand appliance warranties and reconsider extending warranties! 05:09 Intro to our guest, Wyatt Simon! 11:16 Wyatt’s first BRRRR deal. 14:50 A third deal, gone bad! 19:47 How to start direct-to-seller marketing. 28:02 Ins and outs of “subject to” financing deals. 34:07 Navigating liquidity concerns. 37:56 Wyatt’s 5-year outlook! 41:12 What is your competitive advantage? 41:37 One piece of advice for new investors. 42:53 What do you do for fun? 43:10 Good book, podcast, or self development activity that you would recommend? 44:16 Local Network Recommendation? 44:52 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman
04/01/2025
Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman
How does credit effect DSCR loans? ============= 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: Eric Workman, Link: Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren
03/27/2025
Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren
John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John dives into starting a property management company along with building and remaining loyal to a team to support his portfolio. Mr. Warren closes with motivating words on entrepreneurship and why you should take the leap of faith! 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: John Warren, Link: Link: Link: Guest Questions 02:53 Intro to our guest, John Warren! 03:18 Lessons learned from growing a 168-unit portfolio! 06:50 How to simply structure a partnership? 12:00 John’s geographical focus and plans for growth. 21:01 Resetting expectations on real estate investment returns! 23:45 Setting up a property management office. 26:27 Property management software and leveraging virtual assistants. 31:48 John’s recent horror story! 33:53 What would John do differently in his journey? 34:47 Growing a family while pursuing entrepreneurship. 36:50 What is your competitive advantage? 37:18 One piece of advice for new investors. 37:43 What do you do for fun? 38:26 Good book, podcast, or self development activity that you would recommend? 39:00 Local Network Recommendation? 40:15 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry
03/20/2025
Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry
Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations. Scott starts by sharing his experience working at JPMorgan’s Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a case study of an adaptive reuse project and gets granular on how the acquisition opportunity was presented, how the capital was raised, and construction considerations. Scott shares notable due diligence stories and talks about what to look for in buildings when considering adaptive reuse redevelopment. This is a great show that sheds light on the opportunities and incentives available for affordable housing developers! 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: Scott Henry, Link: Link: Link: Link: Guest Questions 02:47 Housing Provider Tip - Dial in your tenant screening process to prevent issues! 04:22 Intro to our guest, Scott Henry! 08:50 The Low Income Housing Tax Credit. 13:25 Case Study - Adaptive Reuse Project! 20:45 Covenants for Tax Credits and Grants. 28:54 Construction Considerations on Adaptive Reuse Projects. 34:03 Shocking stories during due diligence. 37:40 What is your competitive advantage? 38:14 One piece of advice for new investors. 38:34 What do you do for fun? 39:05 Good book, podcast, or self development activity that you would recommend? 40:39 Local Network Recommendation? 41:46 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance
03/18/2025
Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance
What actionable steps do I need to take for the Northwest Side Preservation Ordinance? ============= 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: Brie Schmidt, Link: Link: Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 360: Don’t Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney
03/13/2025
Episode 360: Don’t Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney
David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo provides real life examples of how a land trust can help protect housing providers from lawsuits and help maintain privacy. This show is loaded with valuable tips on asset protection and privacy to help you bulletproof your portfolio! 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: David Lanciotti and Del Denney, Link: Link: Link: Guest Questions 01:51 Housing Provider Tip - Vet tenant’s income before agreeing to a payment plan. 05:31 Intro to our guests, Del and David! 07:30 The Ins and Outs of Land Trusts. 16:41 The downsides of a Land Trust. 22:03 Deep Dive on Trusts and Probate! 29:55 When does it not make sense to set up a Trust? 33:38 The process and costs for setting up a trust. 38:55 What is your competitive advantage? 39:27 One piece of advice for new investors. 39:55 What do you do for fun? 40:30 Good book, podcast, or self development activity that you would recommend? 42:33 Local Network Recommendation? 43:01 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 359: 2025 Cook County Evictions with Tom Raleigh
03/06/2025
Episode 359: 2025 Cook County Evictions with Tom Raleigh
Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions! Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction case. Tom hits us with rapid fire eviction stats including neighborhoods and even streets where his office has had the most eviction filings. He closes with top insights on complying with Fair Housing and tenant screening to avoid eviction court altogether! If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! ============= 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: Tom Raleigh, Link: Link: Link: Guest Questions 02:27 Housing Provider Tip - Dial in your tenant screening process to prevent issues! 04:17 Intro to our guest, Tom Raleigh! 5:01 The Eviction Process in 2025. 12:48 How can landlords get ahead in the eviction process? 21:56 Rapid fire stats on Tom’s eviction filings! 30:40 Housing Section of the CARES Act. 39.28 10 Day Notice for Cause. 47:36 Tips for Landlords to avoid Fair Housing violations. 55:41 What is your competitive advantage? 56:15 One piece of advice for new investors. 56:32 What do you do for fun? 56:58 Good book, podcast, or self development activity that you would recommend? 57:38 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.
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Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio
03/04/2025
Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio
What can I do to maximize my tax returns? ============= 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: Michael Procaccio, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network
02/27/2025
Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network
Tom and Mark interview some of Chicago’s Real Estate Heavy Hitters during Kiser Group’s 20 Year Anniversary Celebration! Conversations range from condo deconversions, the attorney review side of a commercial deal, and the origins and evolution of Kiser Group. This show is full of wisdom from Kiser Group’s top brokers and business partners so prepare to learn from some of the best folks in the industry! 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: Lee Kiser and Guests, Link: Guest Questions 02:57 Housing Provider Tip - People like doing business with people that they like so treat people well! 04:48 Jake Parker’s insights on condo deconversions and more! 10:09 Andy Friedman reflecting on 7 years at Kiser Group! 19:15 Scott Weinstein: Advice from a Commercial Real Estate Attorney. 26:04 Corey Oliver on acquiring and stabilizing multifamily buildings. 37:03 Top tier commercial lending tips with Matt Bower! 44:48 Dominating in Chicago’s Southside with Aaron Sklar! 57:02 CIC’s latest loan options with Stacie Young! 62:20 Kiser Group’s Origins with Estella and Lee Kiser! ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro
02/20/2025
Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro
Frank Montro, the King of Chicagoland, returns to share how he and his real estate team have remained top producers during recent years of high interest rates and prices. Frank explains how he coaches buyers to understand monthly payments as opposed to being scared off by rates and pricing. He discusses the keys to getting off the ground as a new broker and/or investor including tips on networking and cold calling. Frank gives brutally honest advice on the work ethic required to succeed and warns “order-taking” agents of the challenges they will face in this market. In this show, Frank empowers you to “put your nose to the grindstone” to stay ahead of your competition! If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: Email the Show: Guest: Frank Montro, Link: Link: Link: Guest Questions 02:45 Housing Provider Tip - Notify your insurance broker of slip and fall incidents to ensure you’re covered! 04:49 Intro to our guest, Frank Montro! 17:24 Surviving as a new broker in today’s market. 23:54 Keys to lead generation and deal flow! 40:16 Committing to real estate while having work-life balance. 64:36 What is your competitive advantage? 64:55 One piece of advice for new investors. 65:24 What do you do for fun? 66:08 Good book, podcast, or self development activity that you would recommend? 66:42 Local Network Recommendation? 67:20 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 355: How To Optimize Tax Deductions as a Househacker
02/18/2025
Episode 355: How To Optimize Tax Deductions as a Househacker
What Can I Write Off as a Chicago Househacker? ============= 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: Michael Procaccio, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon
02/13/2025
Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon
Jake Fugman and Mike Scanlon of The Axon Group return to discuss Chicago’s REI market performance, predictions, and exciting developments! Jake and Mike kick things off by assessing their 2024 predictions regarding mortgage rates, appreciation, and cap rates! They then break down the impacts of the Northwest Side Housing Preservation on landlords in the area and provide noteworthy predictions for 2025. These predictions include what the new presidential administration will mean for the downtown market, househacker purchasing power with 5% down, the 1901 project, the path of progress, and much more! 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 Fugman & Mike Scanlon, Link: Link: Link: Link: Link: Link: Link: Guest Questions 02:25 Housing Provider Tip - Consult with your attorney and insurance agent on handling slip and fall incidents. 03:17 Intro to our guests, Jake Fugman and Mike Scanlon! 7:59 House Hackers unlocking huge leveraged returns with 5% down! 16:13 What did cap rates do in 2024? 20:22 Prediction 1: The return of 100% bonus depreciation. 24:37 Impacts of the Northwest Side Housing Preservation Ordinance. 38:00 Will downtown Chicago make a comeback? 49:24 Investing in 2-4 unit new construction buildings. 54:37 The 1901 Project! 63:04 What is your competitive advantage? 65:33 One piece of advice for new investors. 67:28 What do you do for fun? 68:25 Good book, podcast, or self development activity that you would recommend? 70:26 Local Network Recommendation? 71:17 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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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.
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Episode 352: Current Issues The NBOA is Fighting with Mike Glasser
02/04/2025
Episode 352: Current Issues The NBOA is Fighting with Mike Glasser
What are the current political issues Chicago investors need to be aware of and how can the NBOA help? ============= 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: Mike Glasser, ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 351: Obstacles Affordable Housing Developers Face in Illinois with Richard Koenig
01/30/2025
Episode 351: Obstacles Affordable Housing Developers Face in Illinois with Richard Koenig
Richard Koenig is HODC’s Executive Director and has led the development of over 600 units of affordable housing! Richard starts with how he found his “Why” and discovering that he wanted to dedicate his career to helping solve the lack of affordable housing. He gets granular on the financing and approval process on these types of developments. Richard compares market rate housing to affordable housing including cost to build and tenant screening. He shares advice on how smaller investors can help contribute to the affordable housing issue and make a positive impact in their community! 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: Richard Koenig, Link: Link: Guest Questions 01:48 Housing Provider Tip - The legal way around HOA rules about lease terms! 03:47 Intro to our guest, Richard Koenig! 08:15 Financing and tax credits for affordable housing development. 14:32 Guidelines for affordable housing designation. 19:08 Dealing with affordable housing critics. 25:31 The economics of building affordable housing. 31:05 Tenant screening process! 38:53 Contributing to affordable housing as a smaller investor. 44:58 Top challenges for developers. 48:27 Opportunities for improvements to bring more development. 51:39 What is your competitive advantage? 51:55 One piece of advice for new investors. 52:18 What do you do for fun? 52:40 Good book, podcast, or self development activity that you would recommend? 53:09 Local Network Recommendation? 54:07 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 350: Reality TV to Realty… Everything Chicago Investor Mike Tenerelli Has Accomplished
01/23/2025
Episode 350: Reality TV to Realty… Everything Chicago Investor Mike Tenerelli Has Accomplished
Mike Tenerelli not only has a background in Reality TV, but also in construction, management, and sales which have propelled his explosive growth in real estate! Mike discusses his journey from flipping homes to helping others find the right property. He breaks down analyzing remote markets to find lucrative deals, growing a brokerage business, and adapting to the new NAR rules around buyer’s broker compensation. Mike shares tremendous insights on investment opportunities in prime western burbs and lessons learned from flipping gone wrong! 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: Mike Tenerelli, Link: Link: Link: Guest Questions 02:27 Housing Provider Tip - Plan accordingly when giving Section 8 tenants notice to vacate! 04:24 Intro to our guest, Mike Tenerelli! 09:18 Becoming a full time investor after 2 flips! 11:42 Learning the Milwaukee market. 20:54 Growing a brokerage business. 24:38 Dealing with new NAR compensation rules. 33:10 The 101 on the Western Burbs! 38:01 Consequences of Flipping Gone Wrong! 42:02 What is your competitive advantage? 42:40 One piece of advice for new investors. 43:28 What do you do for fun? 43:46 Good book, podcast, or self development activity that you would recommend? 44:07 Local Network Recommendation? 44:46 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 349: Do I Need To Give My Tenant a 30 Day Notice?
01/21/2025
Episode 349: Do I Need To Give My Tenant a 30 Day Notice?
When Does a 5 Day Notice Become a 30 Day Notice? ============= 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: Mark Ainley, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 348: Sam Patterson Is All In On This Western Suburb W/Property Taxes Going Down
01/16/2025
Episode 348: Sam Patterson Is All In On This Western Suburb W/Property Taxes Going Down
Sam Patterson is a successful Commercial Real Estate Broker, Investor, and Restaurant Owner with vast experience in renovation and property management! Sam opens with his experience in commercial real estate receiverships and his start in investing! He touches on structuring and leveraging partnerships to scale a real estate portfolio. Sam discusses ins and outs of DeKalb including the housing stock and the investment opportunities. In sharing his project experiences, Sam speaks to seller financing, TIF funds, and various other concepts to add to your real estate toolbox! 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: Sam Patterson, | Link: Link: Guest Questions 03:39 Housing Provider Tip - Take precautionary measures to deal with Chicago’s frigid temperatures! 05:40 Intro to our guest, Sam Patterson! 08:41 Crazy receivership stories and becoming an investor! 19:48 Why invest in West Chicago? 23:01 Structuring a partnership. 29:57 DeKalb’s housing stock and investment expectations. 38:38 How TIF funds work! 41:13 Surprises on a large commercial property renovation! 44:16 An overview of Sycamore. 50:24 Refinance terms on a commercial loan. 53:17 What’s next in Sam’s investment journey? 58:24 What is your competitive advantage? 59:19 One piece of advice for new investors. 60:11 What do you do for fun? 60:49 Good book, podcast, or self development activity that you would recommend? 61:32 Local Network Recommendation? 62:11 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 347: Solving Housing Affordability With Josh Bandoch
01/09/2025
Episode 347: Solving Housing Affordability With Josh Bandoch
Josh Bandoch is the Head of Policy at the Illinois Policy Institute where he works to spread awareness on improving housing policies to promote affordability and social mobility. Josh starts by describing how he got into housing policy and the mission of the Illinois Policy Institute. He explains some of the prohibitive policies in Illinois that restrict development and the increase of housing supply. Josh discusses the power of ADUs to bring affordable housing supply and how other cities with less restrictions have successfully developed ADUs. He closes by explaining how Illinois can and should look at the policies in other states that have helped solve affordable housing and state debt issues. This is a great show to understand macro-level issues we deal with here in Illinois and how we can make our voice heard to help reach solutions! 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: Josh Bandoch, Link: Link: Guest Questions 01:35 Housing Provider Tip - Keep heat on in vacant units to prevent pipe bursts and other issues during winter! 03:36 Intro to our guest, Josh Bandoch! 06:42 The Illinois Policy Institute and its mission! 13:21 Policies negatively impacting housing affordability. 24:23 Benefits of ADUs and restrictions in Illinois. 34:14 Places with the least amount of housing regulation. 38:05 Dissecting Illinois Property Taxes! 44:54 Looking outside of Chicago to solve Chicago’s problems! 47:47 What is your competitive advantage? 48:46 One piece of advice for new investors. 49:12 What do you do for fun? 49:47 Good book, podcast, or self development activity that you would recommend? 50:34 Local Network Recommendation? 51:00 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 346: Three New Laws Illinois Investors Need to be Aware of in 2025
01/07/2025
Episode 346: Three New Laws Illinois Investors Need to be Aware of in 2025
What IL rules changes do investors need to be aware of in 2025? ============= 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: Mark Ainley, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 345: Multiple Logan Square 3-Flats With Less Than $10k Down…Hear How with Joey Turano
01/02/2025
Episode 345: Multiple Logan Square 3-Flats With Less Than $10k Down…Hear How with Joey Turano
Joey Turano is real estate broker and investor who has leveraged partnerships and low down payment loans to quickly build his multifamily buildings portfolio! Joey starts by describing his “soul searching” journey in Europe and realizing that real estate would be his career path in life! He explains how he got scrapy to bring value to a Top Producing Real Estate agent and eventually joined the team to learn the ropes of real estate brokerage. Joey describes how he quickly purchased two househacks by leveraging low down payment loans and partnerships. He drops some hilarious horror stories on tenants and DIY projects and also reflects on his investment strategy and how it will be refined moving forward! This is another great show that demonstrates how taking action sooner than later is a 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: Guest: Joey Turano, Link: Link: Link: Link: Guest Questions 03:31 Housing Provider Tip - Keep space heaters handy to be prepared for No Heat situations in winter! 06:16 Intro to our guest, Joey Turano! 10:33 Getting into real estate and choosing a team. 15:52 Working Zillow leads and getting into investing. 18:26 Strategies to get into REI! 21:36 Joey’s first deal. 26:51 Quickly buying deal #2. 30:20 Lessons from DIY projects and partnering with family. 35:09 Funny, horror stories! 38:20 Refining an investment strategy. 47:04 What is your competitive advantage? 47:45 One piece of advice for new investors. 48:32 What do you do for fun? 49:00 Good book, podcast, or self development activity that you would recommend? 49:32 Local Network Recommendation? 50:21 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024.
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Episode 344: Finding Success in Sourcing and Renovating Deals with Seasoned GC Boyan Salha
12/26/2024
Episode 344: Finding Success in Sourcing and Renovating Deals with Seasoned GC Boyan Salha
Boyan Salha is a seasoned General Contractor and the leader of his company Best Fit Homes. He joins us to share how he learned to source and renovate deals from working with a large investment group. Boyan starts by explaining the investing lessons learned by working with a large investment group alongside previous guest Kirby Atwell! He breaks down how he sources and finances distressed properties. He discusses his flipping experiences and how margins have changed over the years. Boyan talks about building relationships with subcontractors and the value that a quality General Contractor brings to their client. This show is full of golden nuggets from the perspective of an investor GC! 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: Boyan Salha, Link: Link: Link: Link: Guest Questions 02:44 Housing Provider Tip - Adjust terms so rentals being marketed in the winter end during the spring/summer rental season. 05:17 Intro to our guest, Boyan Salha. 12:21 Connecting with Kirby Atwell and getting into real estate. 23:51 Starting a General Contracting business! 28:18 Financing distressed properties. 30:42 Transitioning from flips to owning rentals. 39:43 Working as a General Contractor for third parties. 42:31 Growing a team of sub-contractors and the value of a good GC! 48:58 Boyan’s investing strategy in 2024 and outlook on Chicago. 52:58 What is your competitive advantage? 53:30 One piece of advice for new investors. 54:35 What do you do for fun? 55:30 Good book, podcast, or self development activity that you would recommend? 57:08 Local Network Recommendation? 58:36 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024.
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Episode 343: The IL 2025 Tenant Credit Report Law
12/24/2024
Episode 343: The IL 2025 Tenant Credit Report Law
What do investors need to know about the new tenant credit report law? ============= 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: Mark Ainley, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2024.
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Episode 342: Building and Selling a 7-Figure Property Management Company and Leveling Up with Virtual Assistants with Pete Neubig
12/19/2024
Episode 342: Building and Selling a 7-Figure Property Management Company and Leveling Up with Virtual Assistants with Pete Neubig
Pete Neubig joins us to discuss how he built and sold a 7-figure property management company and started VPM Solutions; a platform designed to help property management and real estate professionals with staffing to improve efficiencies and profits! Pete starts by explaining how he went from IT to building and selling a 7-figure property management company! He shares a brief horror story about getting sued for $1.5 million! He discusses how he started VPN Solutions on the “Who Not How” concept; Pete is leveraging remote staff to offload work to focus on higher-dollar activities. This show is packed with fantastic tips to help improve your business and grow your bottom line! 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: Pete Neubig, Link: Link: Link: Guest Questions 03:08 Housing Provider Tip - Consider outsourcing all or select aspects of property management! 05:10 Intro to our guest, Pete Neubig! 9:27 Getting sued for $1.5 million! 11:21 Making the jump to start a business. 17:40 Finding a mentor / coach and growing a business! 27:58 Outsourcing property management! 39:04 Processes for hiring management personnel. 48:33 What is your competitive advantage? 49:05 One piece of advice for new investors. 49:15 What do you do for fun? 50:00 Good book, podcast, or self development activity that you would recommend? 50:25 Local Network Recommendation? 50:42 How can the listeners learn more about you and provide value to you? ----------------- Production House: Copyright of Straight Up Chicago Investor 2024.
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