Straight Up Chicago Investor

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479

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Sep 2026

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About the show

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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September 3, 2026Episode 4761 hr 0 min

Episode 476: 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! ============= C onnect 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.

September 1, 2026Episode 47511 min

Episode 475: Leveraging 311 and Scattered Public Data Sources For Chicago Buildings with Jim McMahon

How can Property Sentinel help me as a Chicago building owner? ============= C onnect 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.

August 27, 2026Episode 4741 hr 4 min

Episode 474: 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! ============= C onnect 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.

August 20, 2026Episode 4731 hr 8 min

Episode 473: 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! ============= C onnect 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.

August 18, 2026Episode 47214 min

Episode 472: The 101 on Porch Issues and Repairs with Mr. Porch Frank Knight

How do I evaluate and fix a Chicago porch? ============= C onnect 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.

August 13, 2026Episode 47159 min

Episode 471: 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! ============= C onnect 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.

August 6, 2026Episode 4701 hr 26 min

Episode 470: 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! ============= C onnect 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.

August 4, 2026Episode 46913 min

Episode 469: 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? ============= C onnect 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.

July 30, 2026Episode 46859 min

Episode 468: 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! ============= C onnect 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.

July 23, 2026Episode 4671 hr 2 min

Episode 467: 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! ============= C onnect 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.