Straight Up Chicago Investor

Straight Up Chicago Investor
  • 5.0 (301)
  • 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. 1d ago

    The Proposed Move Act: Where Owners Can Transfer Their Existing Mortgage

    What do investors need to know regarding the proposed legislation for both the Road To Housing and Move Act? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo 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.

    The Proposed Move Act: Where Owners Can Transfer Their Existing Mortgage

  2. 6d ago

    Building an 80-Unit Portfolio in 2 Years with Arthur Barkan

    Arthur Barkan of Barkan Realty joins us to share how he rapidly scaled his multifamily portfolio to 80 units! Arthur breaks down the ins and outs of investing in North Chicago, current market deal flow, and evaluating troubling tenants and potential evictions! He also shares strategies for scaling faster, tools to improve property management operations, and lessons learned from working with villages in the northern suburbs. Arthur gets granular on financing properties, capital recycling through refinances, and evaluating cash flow vs long-term net worth. He closes with his five-year vision to continue rapidly scaling his 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: 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: Arthur Barkan, Barkan Realty | Call Arthur: 224-433-4553 Link: Arthur's Instagram Link: Real Life Investing Podcast with Arthur Barkan Guest Questions:  02:43 Housing Provider Tip - Understand cost segregation implications if planning to sell a property in the near term. 03:28 Intro to our guest, Arthur Barkan! 08:40 The ins and outs of North Chicago. 17:26 Assessing a potential eviction scenario. 26:17 Deal flow in today's market. 33:12 Strategies to scale faster! 36:53 Tools to streamline property management. 44:40 Dealing with the Village of North Chicago. 51:39 5 Year Outlook on Arthur's business! 57:37 What's your competitive advantage? 57:53 One piece of advice for new investors. 58:01 What do you do for fun? 58:22 Good book, podcast, or self development activity that you would recommend?  59:15 Local Network Recommendation?  59:23 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.

    Building an 80-Unit Portfolio in 2 Years with Arthur Barkan

  3. Sep 3

    Jake Rome on Leverage, Underwriting, and the Future of Real Estate Financing: How Backflip Is Revolutionizing Fix & Flip Lending

    Jake Rome, co-founder of Backflip, joins us to share the wild journey from institutional real estate private equity to building a vertically integrated lending platform for fix-and-flip investors! Jake breaks down the return-on-equity math that makes single-family flips so powerful, then digs into the leverage and risk decisions that separate successful investors from those who blow up their portfolios. He explains why Backflip decided to service and securitize its own loans, what red flags show up in underwriting (wholesaler markups, seller concessions), and how Chicago's Cook County foreclosure timeline uniquely impacts local lending. Jake also shares his outlook on where the fix-and-flip capital markets are headed, plus how he's using AI to run his own real estate 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: 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: Jake Rome, Backflip Connect with Backflip: LinkedIn | Instagram | Careers Link: Ready to fund your next deal? Apply with Backflip here. Guest Questions:  02:07 – Housing Provider Tip: What to do when a tenant stops paying rent 04:04 – Intro to our guest, Jake Rome of Backflip! 06:07 – From institutional real estate private equity to startups 13:44 – How the idea for Backflip was born 19:25 – Breaking down return on equity on a fix and flip 23:27 – Understanding leverage, risk, and how much is too much 28:09 – Building Backflip: raising capital and servicing their own loans 34:13 – Underwriting red flags: wholesaler markups & seller concessions 39:17 – Where Backflip lends, and the Cook County foreclosure timeline 44:36 – Red flags for first-time construction loan borrowers 46:39 – What lenders actually look for: credit score, experience, liquidity 51:10 – Building community: closing dinners and "Burgers and Flips" 53:19 – The future of fix-and-flip lending and securitization 56:08 – Competitive advantage & advice for new investors 57:53 – How listeners can learn more about Jake and Backflip ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Jake Rome on Leverage, Underwriting, and the Future of Real Estate Financing: How Backflip Is Revolutionizing Fix & Flip Lending

  4. Sep 1

    Leveraging 311 and Scattered Public Data Sources For Chicago Buildings with Jim McMahon

    How can Property Sentinel help me as a Chicago building owner? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jim McMahon, Property Sentinel 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.

    Leveraging 311 and Scattered Public Data Sources For Chicago Buildings with Jim McMahon

  5. Aug 27

    Inside the NBOA Summer Soiree: Chicago Real Estate Advocacy, Networking, and Investor Lessons

    We're taking Straight Up Chicago Investor on the road for a special live episode from the NBOA Summer Soiree! We catch up with some of Chicago's most active real estate professionals to get their takes on what's happening across the market right now. Jeff Weinberg breaks down a 65-unit 1031 deal, Nate Fernandez shares his latest western suburban acquisition, and Mike Glasser and Brie Schmidt discuss the future of NBOA and how housing providers can make their voices heard. We also talk South Side building operations with Corey Oliver, property management efficiencies with CIC's Erica Myles, small multifamily investing with Noah Birk, rehabs and development with Gabe Horstick, and today's lending environment with Eric Workman. Tune in for a fast-paced episode packed with boots-on-the-ground insights from investors and housing professionals across Chicagoland! 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: NBOA Summer Soiree by NBOA Chicago Guest Questions:  04:02 Jeff Weinberg breaks down a 65-Unit 1031 deal! 14:26 Nate Fernandez discusses his latest portfolio acquisition in the western suburbs. 18:15 The outlook of the NBOA with Mike Glassner! 22:47 How to make your voice heard as a housing provider with Brie Schmidt. 29:16 Keys to successful building operations on the south side with Corey Oliver. 35:13 Improving property management efficiencies with CIC's Erica Miles. 40:14 Small multifamily investing with Noah Birk! 46:55 The 101 of rehabs and development with Gabe Horstick. 54:58 Eric Workman shares where and how deals are getting funded. ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

    Inside the NBOA Summer Soiree: Chicago Real Estate Advocacy, Networking, and Investor Lessons

  6. Aug 20

    How AI is Changing Property Management with Pablo Gonzalez

    Pablo Gonzalez of Vendoroo joins us to discuss how AI is changing the way real estate investors and property managers operate and scale their businesses! Pablor shares insights on raising capital and building communities before diving into how AI can be implemented in real estate operations. He breaks down how Vendoroo uses AI to coordinate maintenance, understand tenant sentiment, and help property managers operate more efficiently. Pablo also discusses when it makes sense for landlords to implement these tools and shares his outlook on the future of property management as AI continues to evolve! 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: Pablo Gonzalez, Vendoroo Link: Pablo's LinkedIn Link: Vendoroo Property Maintenance Call Test Link: Play Bigger (Book Recommendation) Link: JWB Real Estate Capital Guest Questions:  02:22 Housing Provider Tip - Leverage AI and other tools to improve maintenance requests response time! 03:24 Intro to our guest, Pablo Gonzalez! 14:54 Strategies to raise capital. 26:45 How to build and leverage a community to grow your business. 36:20 Implementing AI to scale a business. 41:22 The value of Vendoroo!                                                45:40 Understanding tenant and client sentiment. 49:25 At what unit count does it make sense to implement Vendoroo? 53:32 The future of the property management industry. 60:40 What is your competitive advantage? 61:17 One piece of advice for new investors. 62:47 What do you do for fun? 63:20 Good book, podcast, or self development activity that you would recommend?  63:44 Local Network Recommendation?  65:25 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.

    How AI is Changing Property Management with Pablo Gonzalez

  7. Aug 18

    The 101 on Porch Issues and Repairs with Mr. Porch Frank Knight

    How do I evaluate and fix a Chicago porch? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Frank Knight, Mr. Porch Link: Understanding the Cost and Maintenance of Chicago Porches with Mr. Porch 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.

    The 101 on Porch Issues and Repairs with Mr. Porch Frank Knight

  8. Aug 13

    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
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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
    480
  • Rating
    Explicit
  • Copyright
    © Copyright of Straight Up Chicago Investor 2021.
  • Show Website
    Straight Up Chicago Investor

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