Straight Up Chicago Investor

Straight Up Chicago Investor
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Mar 27, 2025 • 44min

Episode 363: 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.
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Mar 20, 2025 • 44min

Episode 362: 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.
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Mar 18, 2025 • 15min

Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance

What actionable steps do I need to take for the Northwest Side Preservation Ordinance? ============= 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: Brie Schmidt, Second City Real Estate Link: Northwest Side Preservation Ordinance Link: The Current State Of Chicago's Northside Real Estate Market With Managing Broker Brie Schmidt Link: Episode 327: Logan & Humboldt Property Owners' Rights Taken By The New NW Preservation Ordinance with Luke Blahnik ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
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Mar 13, 2025 • 46min

Episode 360: Don't Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney

David Lanciotti and Del Denney of The Land Trust Company explain why all real estate investors should understand and consider utilizing Land Trusts! David and Del jump right in by explaining the basics and complexities associated with land trusts. They dive into the challenges that may arise when transferring properties into land trusts. The duo provides real life examples of how a land trust can help protect housing providers from lawsuits and help maintain privacy. This show is loaded with valuable tips on asset protection and privacy to help you bulletproof your 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 Guest: David Lanciotti and Del Denney, The Land Trust Company Link: High Performance Playbook (Del's Book!) Link: Deep Work (Book Recommendation) Link: Bunkhouse Logic (Book Recommendation) Guest Questions 01:51 Housing Provider Tip - Vet tenant's income before agreeing to a payment plan. 05:31 Intro to our guests, Del and David! 07:30 The Ins and Outs of Land Trusts. 16:41 The downsides of a Land Trust. 22:03 Deep Dive on Trusts and Probate! 29:55 When does it not make sense to set up a Trust? 33:38 The process and costs for setting up a trust. 38:55 What is your competitive advantage? 39:27 One piece of advice for new investors. 39:55 What do you do for fun? 40:30 Good book, podcast, or self development activity that you would recommend? 42:33 Local Network Recommendation? 43:01 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.
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Mar 6, 2025 • 1h 1min

Episode 359: 2025 Cook County Evictions with Tom Raleigh

Tom Raleigh, Founding Attorney of Halsted Law Group, returns after being on Episode 40 to talk evictions! Tom jumps right in by breaking down the eviction process and the timelines in 2025. He gives great tips on getting ahead of the process and emphasizes the importance of staying on top of tenants and not waiting too long to file the eviction case. Tom hits us with rapid fire eviction stats including neighborhoods and even streets where his office has had the most eviction filings. He closes with top insights on complying with Fair Housing and tenant screening to avoid eviction court altogether! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= 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: Tom Raleigh, Halsted Law Group Link: Tom Raleigh's LinkedIn Link: Meditations (Book Recommendation) Link: Shawn Ryan Show (Podcast Recommendation) Guest Questions 02:27 Housing Provider Tip - Dial in your tenant screening process to prevent issues! 04:17 Intro to our guest, Tom Raleigh! 5:01 The Eviction Process in 2025. 12:48 How can landlords get ahead in the eviction process? 21:56 Rapid fire stats on Tom's eviction filings! 30:40 Housing Section of the CARES Act. 39.28 10 Day Notice for Cause. 47:36 Tips for Landlords to avoid Fair Housing violations. 55:41 What is your competitive advantage? 56:15 One piece of advice for new investors. 56:32 What do you do for fun? 56:58 Good book, podcast, or self development activity that you would recommend? 57:38 Local Network Recommendation? 58:38 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.
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Mar 4, 2025 • 12min

Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio

What can I do to maximize my tax returns? ============= 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: Michael Procaccio, Pro Financial Services Group Inc. Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
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Feb 27, 2025 • 1h 24min

Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network

Tom and Mark interview some of Chicago's Real Estate Heavy Hitters during Kiser Group's 20 Year Anniversary Celebration! Conversations range from condo deconversions, the attorney review side of a commercial deal, and the origins and evolution of Kiser Group. This show is full of wisdom from Kiser Group's top brokers and business partners so prepare to learn from some of the best folks in the industry! 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: Lee Kiser and Guests, Kiser Group Link: SUCI Ep 239 - Reducing Assessed Value with Fritz Kaegi and Stacie Young Guest Questions 02:57 Housing Provider Tip - People like doing business with people that they like so treat people well! 04:48 Jake Parker's insights on condo deconversions and more! 10:09 Andy Friedman reflecting on 7 years at Kiser Group! 19:15 Scott Weinstein: Advice from a Commercial Real Estate Attorney. 26:04 Corey Oliver on acquiring and stabilizing multifamily buildings. 37:03 Top tier commercial lending tips with Matt Bower! 44:48 Dominating in Chicago's Southside with Aaron Sklar! 57:02 CIC's latest loan options with Stacie Young! 62:20 Kiser Group's Origins with Estella and Lee Kiser! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
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Feb 20, 2025 • 1h 11min

Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro

Frank Montro, the King of Chicagoland, returns to share how he and his real estate team have remained top producers during recent years of high interest rates and prices. Frank explains how he coaches buyers to understand monthly payments as opposed to being scared off by rates and pricing. He discusses the keys to getting off the ground as a new broker and/or investor including tips on networking and cold calling. Frank gives brutally honest advice on the work ethic required to succeed and warns "order-taking" agents of the challenges they will face in this market. In this show, Frank empowers you to "put your nose to the grindstone" to stay ahead of your competition! 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: Frank Montro, Frank Montro Homes Link: SUCI Ep 64 - Frank Montro Link: Exactly What To Say (Book Recommendation) Link: Martin Lorenzen (Lender Referral) Guest Questions 02:45 Housing Provider Tip - Notify your insurance broker of slip and fall incidents to ensure you're covered! 04:49 Intro to our guest, Frank Montro! 17:24 Surviving as a new broker in today's market. 23:54 Keys to lead generation and deal flow! 40:16 Committing to real estate while having work-life balance. 64:36 What is your competitive advantage? 64:55 One piece of advice for new investors. 65:24 What do you do for fun? 66:08 Good book, podcast, or self development activity that you would recommend? 66:42 Local Network Recommendation? 67:20 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.
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Feb 18, 2025 • 18min

Episode 355: How To Optimize Tax Deductions as a Househacker

What Can I Write Off as a Chicago Househacker? ============= 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: Michael Procaccio, Pro Financial Services Group Inc. Link: Build Your Team | Straight Up Chicago Investor Podcast ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
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Feb 13, 2025 • 1h 14min

Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon

Jake Fugman and Mike Scanlon of The Axon Group return to discuss Chicago's REI market performance, predictions, and exciting developments! Jake and Mike kick things off by assessing their 2024 predictions regarding mortgage rates, appreciation, and cap rates! They then break down the impacts of the Northwest Side Housing Preservation on landlords in the area and provide noteworthy predictions for 2025. These predictions include what the new presidential administration will mean for the downtown market, househacker purchasing power with 5% down, the 1901 project, the path of progress, and much more! 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: Jake Fugman & Mike Scanlon, The Axon Group Link: The Axon Group Instagram Link: SUCI Ep 268 - 2024 Predictions with Jake and Mike Link: SUCI Ep 327 - Luke Blahnik on NW Preservation Ordinance Link: REI Diamonds Podcast Link: ADPI Podcast Link: Kevin Kaspers (Lender Referral) Link: Cost Seg Kev Guest Questions 02:25 Housing Provider Tip - Consult with your attorney and insurance agent on handling slip and fall incidents. 03:17 Intro to our guests, Jake Fugman and Mike Scanlon! 7:59 House Hackers unlocking huge leveraged returns with 5% down! 16:13 What did cap rates do in 2024? 20:22 Prediction 1: The return of 100% bonus depreciation. 24:37 Impacts of the Northwest Side Housing Preservation Ordinance. 38:00 Will downtown Chicago make a comeback? 49:24 Investing in 2-4 unit new construction buildings. 54:37 The 1901 Project! 63:04 What is your competitive advantage? 65:33 One piece of advice for new investors. 67:28 What do you do for fun? 68:25 Good book, podcast, or self development activity that you would recommend? 70:26 Local Network Recommendation? 71:17 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.

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