Straight Up Chicago Investor

Straight Up Chicago Investor
  • 5.0 (300)
  • Investing
  • Updated Weekly

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. 4d ago

    Progression Of Wholesaling to Investor with Mark Skowron

    Mark Skowron of Festival Properties joins us to share top insights from his real estate journey which began back in 2010! Mark explains how he got started in real estate and pitfalls to avoid when building a wholesaling business! He shares how he got scrappy to find deals and eventually vetted and leveraged virtual assistants to scale. Mark dives into out of state investing including buying businesses in remote markets. He closes with lessons learned on out of state investing and some crazy wholesaling stories! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Mark Skowron, Festival Properties Link: Mark's LinkedIn Link: The Untethered Soul (Book Recommendation) Link: Investor Fuse Guest Questions:  02:18 Housing Provider Tip - Understand when it's actually necessary to refinish hardwood floors! 03:38 Intro to our guest, Mark Skowron! 18:27 Vetting and leveraging VAs! 23:05 Scaling a wholesaling business. 31:23 Wild wholesaling stories! 38:33 How to scale virtually in a remote market. 43:55 Mistakes made on deals in other markets. 54:51 What is your competitive advantage? 54:59 One piece of advice for new investors. 55:08 What do you do for fun? 55:22 Good book, podcast, or self development activity that you would recommend?  55:58 Local Network Recommendation?  56:44 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Progression Of Wholesaling to Investor with Mark Skowron

  2. Aug 6

    0-9 Unit Portfolio in Under Two Years with Hart Turner

    Hart Turner joins us to share how he went from a career in Los Angeles to building a Chicago multifamily portfolio through house hacking and partnerships! Hart dives into how he got started investing and how house hacking allowed him to get in the game! He shares real numbers behind his deals, discusses navigating financing challenges, and reflects on costly mistakes that shaped his investing approach. Hart dives deep into his most recent acquisition in Humboldt Park and shares lessons learned on inspection issues, negotiation, and leveraging seller credits. He closes by sharing his outlook on continuing to grow a sustainable Chicago real estate portfolio while avoiding the pitfalls many new investors face! 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 Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Hart Turner, Hotspot Rentals Link: Hart's TikTok Link: Hart's Instagram Link: Real Life Investing Podcast Link: Chicago Multifamily Club Meetup Link: I Will Teach You To Be Rich (Book Recommendation) Link: BPCON 2026 Guest Questions:  02:43 Housing Provider Tip - Avoid fraudulent  tenants by leveraging screen tools! 04:48 Intro to our guest, Hart Turner! 10:16 Jumping into leasing and investing. 22:10 Screening properties as a new investor! 28:44 Overcoming hurdles on a first house hack. 38:33 Partnering on a DSCR loan to acquire a second building! 49:54 4-Unit house hack with 5% down! 70:36 Hart's strategy to continue scaling. 80:06 What is your competitive advantage? 80:37 One piece of advice for new investors. 81:03 What do you do for fun? 81:15 Good book, podcast, or self development activity that you would recommend?  82:14 Local Network Recommendation?  83:23 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    0-9 Unit Portfolio in Under Two Years with Hart Turner

  3. Aug 4

    Different Scenarios That Require Builder's Risk Insurance With Josh Steigelmann

    What is Builders risk insurance and as an investor when do I need this policy? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Different Scenarios That Require Builder's Risk Insurance With Josh Steigelmann

  4. Jul 30

    Scaling a Wholesale Business Quickly with Eric Field

    Eric Field of Big Door Home Buyers joins us to share how he has successfully built his real estate wholesaling business! Eric jumps right in by explaining how he got into wholesaling and how he scaled his business! He provides tactical advice on marketing, wholesaling overhead expenses, and estimating rehab costs. Eric shares wholesaling horror stories and his biggest lessons learned from underwriting mistakes. He closes with an outlook on fine tuning his business to further propel 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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Eric Field, Big Door Home Buyers Link: SUCI Ep 356 - Frank Montro Link: SUCI Ep 253 - Jeff Nydegger (Kendall Partners) Link: Never Split the Difference (Book Recommendation) Guest Questions:  02:05 Housing Provider Tip - Do not skip final walkthroughs and do them on closing day! 03:37 Intro to our guest, Eric Field! 12:33 Starting a wholesaling business. 22:03 Effective marketing strategies. 30:45 Overhead expenses for wholesaling. 34:13 Crazy wholesaling stories! 41:39 Eric's biggest underwriting mistakes. 51:26 Tips for estimating construction costs. 54:16 Business outlook for Big Door Home Buyers. 55:28 What is your competitive advantage? 55:45 One piece of advice for new investors. 56:10 What do you do for fun? 56:24 Good book, podcast, or self development activity that you would recommend?  56:50 Local Network Recommendation?  56:26 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Scaling a Wholesale Business Quickly with Eric Field

  5. Jul 23

    Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months

    SUCI Co-Host Mark Ainley gives a presentation on his deals over the last 30 months at the WSBOA meetup!  Mark shares details on various deals including flips, BRRRRs, and even short-term rentals. He  explains how he sourced, financed, and stabilized these deals. He discusses biggest wins and top lessons learned. Mark closes the presentation with the biggest REI takeaways and a Q&A session 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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Mark Ainley, GC Realty & Development Link: Mark's Instagram Link: WSBOA Meetup Guest Questions:  06:07 Housing Provider Tip - Understand root causes of water intrusion to efficiently solve issues. 08:11 Mark's first acquisition with Lantz! 16:18 Lessons learned on Mark's Hoffman Estates deal. 19:57 Home run BRRRR deal in Schaumburg! 27:56 Mark's syndication deal. 30:36 A quick flip in Downers Grove and FHA househack in Jefferson Park! 36:14 Flip deal in Hanover Park. 37:28 Rough deal in Elgin! 41:18 Mark's recent deal in Rolling Meadows. 42:37 Locking up a Downers Grove Ranch property. 44:38 Experimenting with a Short-Term Rental project! 47:13 Mark's key takeaways! 52:08 Q&A. 59:37 Chicago fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Lessons from Mark Ainley's Real Estate Deals Over the Last 30 Months

  6. Jul 21

    How the Government Can Stop Your Insurance Claim with Josh Steigelmann

    Can the government stop my insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Josh Steigelmann, State Farm Insurance Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    How the Government Can Stop Your Insurance Claim with Josh Steigelmann

  7. Jul 16

    Pat Hynes Is Bringing Transparency to the Cook County Assessor's Office

    Newly elected Cook County Assessor Pat Hynes joins us to share his plan for bringing fair, accurate, and predictable property assessments! Pat starts by discussing the flaws in the current property assessment system and his plan to improve and simplify the system! He shares an emotive story on why he decided to take on the county assessor role. Pat gets granular on common mistakes made on tax appeals and the methodology behind accurate valuations. He closes with insights on the Chicago Bears Stadium site selection and an extremely 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: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Pat Hynes, Cook County Link: Pay Hynes - Lyons Township Page Link: The Devil in the White City (Book Recommendation) Guest Questions:  02:07 Housing Provider Tip - Review property characteristics on tax assessor's website to catch inaccurate info! 02:56 Intro to our guest, Pat Hynes! 11:06 Bringing transparency to property taxation. 17:02 An idealized property valuation approach. 21:47 Pat's motivation to take on the Cook County Assessor role. 27:08 Common mistakes made on property tax appeals. 29:19 The process for valuing condominium buildings. 30:40 Simplifying the appeal process! 39:04 Property tax incentives for providing affordable housing. 43:48 Pat's criteria for a successful term as Cook County Assessor! 45:15 Tax implications for the Chicago Bears Stadium site selection! 50:06 Data Center Taxation. 51:49 What is your competitive advantage? 52:04 One piece of advice for new investors. 52:32 What do you do for fun? 53:09 Good book, podcast, or self development activity that you would recommend?  53:26 Local Network Recommendation?  54:34 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Pat Hynes Is Bringing Transparency to the Cook County Assessor's Office

  8. Jul 9

    Ownership Fraud in West Town: Tom Shallcross and the $1.6 Million Fight to Unwind

    SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down a fraud story on a West Town property that he purchased! Tom dives deep into a recent purchase in West Town that involved ownership fraud when transferring title. He explains how the fraud was detected and how he navigated the process to reach a resolution. Throughout this show, Tom emphasizes the importance of being due diligence and having adequate insurance and documentation in place to protect yourself as best as possible! 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 Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Guest: Tom Shallcross, Co-host of Straight Up Chicago Investor Link: SUCI Ep 420 - Tom Shallcross Guest Questions:  01:38 Housing Provider Tip - Ensure drains are clear of debris or blockage to prevent issues during heavy rainfalls! 02:33 Intro to our guest, Tom Shallcross! 03:25 Intro to Tom's Fraud Property Story! 29:18 The process of clearing up title issues. 42:20 The stress associated with a fraud deal. 47:21 Managing partnerships when issues arise. 48:53 Chicago Fact! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Ownership Fraud in West Town: Tom Shallcross and the $1.6 Million Fight to Unwind
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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 - 2026
  • Episodes
    473
  • Rating
    Explicit
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

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