Straight Up Chicago Investor

Latest Episodes:

Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry Mar 20, 2025

Show notes

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?

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Production House: Flint Stone Media

Episode 361: What To Do Regarding the Northwest Side Preservation Ordinance Mar 18, 2025

Show notes

What actionable steps do I need to take for the Northwest Side Preservation Ordinance?

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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

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Production House: Flint Stone Media

Episode 360: Don't Be Foolish, Protect Your Assets and This Is How with David Lanciotti and Del Denney Mar 13, 2025

Show notes

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?

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Production House: Flint Stone Media

Episode 359: 2025 Cook County Evictions with Tom Raleigh Mar 06, 2025

Show notes

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!

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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?

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Production House: Flint Stone Media

Episode 358: Prepping for Tax Season and Commonly Missed Deductions with Mike Procaccio Mar 04, 2025

Show notes

What can I do to maximize my tax returns?

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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

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Production House: Flint Stone Media

Episode 357: Celebrating 20 Years of Kiser Group: Great Chicago insights From Their Network Feb 27, 2025

Show notes

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!

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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!

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Production House: Flint Stone Media

Episode 356: The No BS Guide to Thriving in Chicago Real Estate, Even in Tough Markets… with Frank Montro Feb 20, 2025

Show notes

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!

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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?

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Production House: Flint Stone Media

Episode 355: How To Optimize Tax Deductions as a Househacker Feb 18, 2025

Show notes

What Can I Write Off as a Chicago Househacker?

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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

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Production House: Flint Stone Media

Episode 354: 2025 Chicago Market Predictions with Jake Fugman and Mike Scanlon Feb 13, 2025

Show notes

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!

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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?

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Production House: Flint Stone Media

Episode 353: From Near Death Experience, to Disciplined Financial Freedom with Mike Bednarz Feb 06, 2025

Show notes

Mike Bednarz, an accomplished real estate investor and HVAC business owner, joins us to share his inspiring trajectory of growing a real estate portfolio and overcoming a scary accident!

Mike explains how he lived frugally to save a down payment and buy his first multifamily investment property in Edison Park. He discusses the discipline he used to acquire his second property and how he found a niche in mixed-use properties with leasing up local retail spaces. Mike shares a life changing incident where he fell off a ladder while working for his HVAC company that resulted in life threatening injuries. He breaks down his recovery despite doctors doubting that it was possible and bouncing back stronger than ever. This is the definition of an inspirational conversation around discipline and grit that you will not 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!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Mike Bednarz, Housing Opportunity Development Corporation (HODC)

Link: Eat That Frog (Book Recommendation)

Link: How Not To Die

Guest Questions

05:09 Housing Provider Tip - Understand the Illinois Landlord Retaliation Act!

06:51 Intro to our guest, Mike Bednarz!

15:40 Jumping into a 6-unit after a house hack!

21:32 Finding a niche in mixed-use buildings.