Straight Up Chicago Investor

Latest Episodes:

Episode 402: Looking At Chicago Investing Differently with Jason Wagner Sep 25, 2025

Show notes

Jason shares why he chose to invest in Chicago's northwest side and how he's achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset's ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors!

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

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

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Guest: Jason Wagner, Greystone Realty

Link: SUCI Ep 224 - Jason Wagner

Link: Real Life Investing with Jason & Rachel Wagner (Podcast)

Link: Wagner Report

Link: The 5 Types of Wealth (Book Recommendation)

Link: SUCI Ep 244 - Ryan Bakke

Guest Questions

02:36 Housing Provider Tip - Ensure utilities are put back in your name in between tenant turnovers!

04:52 Intro to our guest, Jason Wagner!

10:53 Emerging neighborhoods and creative strategies for cash flow!

28:42 Ins and outs of assumable loans.

36:06 Insights on VA loan assumptions.

38:03 The background on Greystone Realty.

42:56 Housing market takeaways from the Wagner Report!

45:58 Opportunities in Arlington Heights.

50:26 Best of advice for aspiring real estate investors.

52:42 What is your competitive advantage?

53:07 One piece of advice for new investors.

53:20 What do you do for fun?

54:28 Good book, podcast, or self development activity that you would recommend?

56:19 Local Network Recommendation?

57:11 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 401: Interest Rates Are Coming Down According to Chris Puleo Sep 23, 2025

Show notes

Chris Puleo lays out tangible reasons why he feels interest rates will be coming down in the upcoming future.

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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

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Guest: Chris Puleo of Puleo Group

Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo

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Production House: Flint Stone Media

Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio Sep 18, 2025

Show notes

Kevin Rocio, founder of ROC Advisory Group, is an award winning commercial real estate broker, mentor, and investor.

Kevin shares how he built a business and sphere of influence in the mortgage lending industry. He discusses his start in commercial real estate and gets granular on various valuation metrics. Kevin talks about the rapid growth of his business during and after the pandemic. He closes with explaining the importance of building a great reputation to set yourself up for success in this relationship-based business!

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

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Guest: Kevin Rocio, ROC Advisory Group

Link: Kevin Rocio's Instagram

Link: Crain's Chicago Business

Link: SUCI Ep 296 - Moses Hall

Link: Mike Levin (Network Referral)

Guest Questions

04:09 Housing Provider Tip - Let insurance representatives know about property improvements to reduce your premium!

05:50 Intro to our guest, Kevin Rocio!

14:45 Transitioning out of mortgage lending after 17 years.

20:46 Starting in real estate brokerage in 2009.

33:16 Utilizing GRM for valuations.

34:51 Kevin's business through and post COVID.

48:31 How to find a mentor!

52:32 Importance of marketing and building a reputation.

55:05 What is your competitive advantage?

55:32 One piece of advice for new investors.

56:08 What do you do for fun?

56:50 Good book, podcast, or self development activity that you would recommend?

58:18 Local Network Recommendation?

59:09 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White Sep 11, 2025

Show notes

Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI!

Micah starts by explaining the ins and outs of his first couple house hacks in Logan Square and North Lawndale. He provides great pointers on proper due diligence to mitigate risk on an investment. Micah shares a hilarious DIY story; moral of the story, hire a professional! He closes with valuable insights on structuring partnerships and building a track record to attract investors!

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

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Guest: Micah White, Brick by Brick Blueprint

Link: Real Estate with Micah

Link: Micah's Instagram

Link: A Long Way Gone (Book Recommendation)

Link: Shoe Dog (Book Recommendation)

Link: Block Club Chicago

Guest Questions

02:22 Housing Provider Tip - Remove window AC units to improve heat efficiency this winter!

03:45 Intro to our guest, Micah White!

14:31 Micah's start in REI!

22:12 Due diligence on your first deal.

26:58 Bumping rents and stabilizing a building.

31:28 The DIY wax ring story!

37:27 Micah's North Lawndale deal.

44:38 Structuring partnerships with investors.

53:20 Reputation building to attract investors.

57:22 What is your competitive advantage?

58:01 One piece of advice for new investors.

58:35 What do you do for fun?

59:45 Good book, podcast, or self development activity that you would recommend?

61:56 Local Network Recommendation?

62:17 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca Sep 04, 2025

Show notes

Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly real estate agent! Paul jumps right into the nitty gritty of his first couple house hack deals! He gives tips on getting off the ground as a new real estate agent and the 101 on Chicago non-conforming units. Paul shares how he handled various troublesome tenants and provides his take on emerging neighborhoods where he's investing! Throughout the episode, Paul demonstrates how focus and taking action have been keys to his investing success!

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

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Guest: Paul de Luca, eXp Realty - The Axon Group

Link: Paul's Instagram

Link: Paul's BiggerPockets

Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon

Link: 5 Types of Wealth (Book Recommendation)

Link: On The Market (Podcast Recommendation)

Link: Adam Gurney (Attorney Referral)

Guest Questions

03:25 Housing Provider Tip - Consider the ROI on central HVAC!

05:08 Intro to our guest, Paul de Luca!

10:52 Reflecting on Paul's first house hack.

13:45 Getting into house hack #2!

21:20 Getting started as a new real estate agent.

25:32 Valuing non-conforming units.

31:33 Handling problem tenants.

36:18 Neighborhood guide for investors!

42:35 Paul's 5 year outlook!

48:48 What is your competitive advantage?

49:23 One piece of advice for new investors.

49:50 What do you do for fun?

50:00 Good book, podcast, or self development activity that you would recommend?

50:31 Local Network Recommendation?

50:55 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property? Sep 02, 2025

Show notes

What are the "do's" and "don'ts" when filing an insurance claim?

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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

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Guest: Josh Steigelmann, State Farm Insurance

Link: Investor Stories Featuring Sean Morrissey

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Production House: Flint Stone Media

Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci Aug 28, 2025

Show notes

Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand!

Fernando explains his marketing strategy to optimize deal flow despite the low inventory environment. He delves deep into the underwriting and feasibility studies performed on self storage investments to maximize returns. Fernando provides the 101 on various financing options and repositioning strategies for self storage investments. He closes with a motivating 5-year outlook including a detailed plan to reach financial independence!

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

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Guest: Fernando Angelucci, Self Storage Syndicated Equities

Link: Fernando's Instagram

Link: SUCI Ep 86 - Fernando Angelucci

Link: Vagabonding (Book Recommendation)

Link: SUCI Ep 392 - Cost Seg Kev

Guest Questions

01:49 Housing Provider Tip - Be sure to perform maintenance on AC units after a long summer!

03:25 Intro to our guest, Fernando Angelucci!

06:41 Growing a portfolio in a low inventory market!

12:10 Feasibility studies on self storage projects.

16:44 Building a self storage investment team!

21:56 Financing self storage deals.

37:33 Repositioning a self storage investment.

47:57 Obtaining special use permits.

52:01 Ideal self storage projects!

55:23 Fernando's 5-year outlook.

60:26 What is your competitive advantage?

62:55 One piece of advice for new investors.

63:32 What do you do for fun?

64:14 Good book, podcast, or self development activity that you would recommend?

64:48 Local Network Recommendation?

65:53 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew Aug 21, 2025

Show notes

Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in Chicago's north side!

Max jumps right in by sharing top considerations when renovating Chicago landmarked properties! He talks about the importance of knowing your market to accurately project rents and pro-formas. Max gets granular on leasing including tips for screening out fraudulent applicants and best marketing practices. Throughout the episode, Max emphasizes the importance of having great relationships with tenants and being an expert in your geographical area of focus as keys to success!

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

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Guests: Max Motew, Mo2 Properties

Link: Max's LinkedIn

Link: SUCI Ep 372 - Kevin Schnell

Link: Neighborhood Building Owner's Alliance - Chicago

Guest Questions

02:05 Housing Provider Tip - Take action and jump into real estate!

03:23 Intro to our guest, Max Motew!

07:10 Considerations on landmarked buildings.

14:04 Making deals "pencil" in today's market.

23:36 Projecting rents and pro-formas!

32:55 Optimizing lease renewals.

43:15 Common leasing mistakes to avoid!

50:08 Screening best practices.

55:57 Up and coming Chicago neighborhoods!

61:18 What is your competitive advantage?

62:25 One piece of advice for new investors.

62:48 What do you do for fun?

63:30 Good book, podcast, or self development activity that you would recommend?

64:09 Local Network Recommendation?

64:37 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 394: The Legal Nuances of Different Real Estate Partnership Structures Aug 19, 2025

Show notes

What do investors need to consider from a legal perspective when setting up new partnerships?

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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

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Guest: Bibek Das, Das Law

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Production House: Flint Stone Media

Episode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy Aug 14, 2025

Show notes

DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits!

DuBois kicks things off by discussing his start in real estate which involved a house hack and dealing with an eviction! He breaks down the rent-by-the-room strategy as a tool to maximize ROI. DuBois dives deep on VA loans, tax exemptions, and various other powerful real estate tools available to veterans! From leveraging AI for deal searching to veteran resources, this show is full of invaluable insights 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!

=============

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

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Guests: DuBois Toy, Trading Technologies

Link: DuBois' Facebook

Link: Cook County Veterans with Disabilities Exemption

Link: Cook County Returning Veterans Exemption