Straight Up Chicago Investor

Straight Up Chicago Investor
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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.

  1. This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson

    4D AGO

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Erik Swanson, Fernweh Property Group Link: Erik Swanson's LinkedIn Link: Eric Workman (Network Referral) 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    55 min
  2. Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)

    APR 17

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360 Link: Joe Smazal's LinkedIn Link: Ann Reilly's LinkedIn Link: SUCI Ep 156 - Joe Smazal Link: Northwest Side Building Coalition (NSBC) Website 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    41 min
  3. How to Get Out In Front of Renewals With Jeff Weinberg

    APR 15

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jeff Weinberg, Drexel Properties Link: Jeff Weinberg Shares Property Management Expertise on the Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    7 min
  4. From Creative Financing to Six-Figure Commission Checks with Jeffrey Ma

    APR 10

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Jeffrey Ma, Keller Williams Preferred Realty Link: Jeffrey's Instagram Link: Chicago Real Estate Investors Meetup Link: Eli Goodman's LinkedIn Link: SUCI Ep 326 - RJ de Leon (Network Referral) Link: Mind Management, Not Time Management (Book Recommendation) 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    55 min
  5. Building a $20 Million Portfolio Using BRRRR with Wyatt Simon

    APR 3

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Wyatt Simon, Full Circle Real Estate Link: Wyatt's Instagram Link: Wyatt's 7 Figure Mastermind Link: Your First 100 Units (Wyatt's Book) Link: 7 Habits of Highly Effective People (Book Recommendation) Link: Jake and Geno (Network Referral) 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    47 min
  6. Small Credit Items That Lead to Large Financial Impacts with Eric Workman

    APR 1

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    14 min
  7. 168 Western Suburb units In Less Than 10 Years with John Warren

    MAR 27

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Warren, Forte Properties Link: Forte Properties (@fortepropertieschicago) • Instagram photos and videos Link: Extreme Ownership (Book Recommendation) Link: Luke Erlandson (Agency Lender Referral) 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    44 min
  8. Free Money to Develop Affordable Housing? Learn How with Scott Henry

    MAR 20

    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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Scott Henry, Celadon Partners Link: Scott's LinkedIn Link: Banana Ball (Book Recommendation) Link: Landmarks Illinois (Network Referral) Link: SUCI Ep 351 - Richard Koenig 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: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.

    44 min
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About

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.

Information

  • Creator
    Straight Up Chicago Investor
  • Years Active
    2020 - 2025
  • Episodes
    371
  • Rating
    Clean
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

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