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.

Straight Up Chicago Investor is a business podcast hosted by Unknown Host, with 475 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Straight Up Chicago Investor, a business show with 475 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #472

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

  Aug 18, 202615 min

  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.

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  Episode #471

  Episode 471: Progression Of Wholesaling to Investor with Mark Skowron

  Aug 13, 202659 min

  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.

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  Episode #470

  Episode 470: 0-9 Unit Portfolio in Under Two Years with Hart Turner

  Aug 6, 20261h 26m

  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.

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  Episode #469

  Episode 469: Different Scenarios That Require Builder's Risk Insurance With Josh Steigelmann

  Aug 4, 202614 min

  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.

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  Episode #468

  Episode 468: Scaling a Wholesale Business Quickly with Eric Field

  Jul 30, 20261 hour

  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.

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