Straight Up Chicago Investor

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**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.

Latest Episodes:

Episode 204: Public Relations 101 - What to Say if a Reporter Contacts You Regarding Your Building Mar 14, 2023

Show notes

An incident happened at my building and now a reporter has reached out. How should I respond?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Myk Snider of Sphere Public Relations

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Production House: Flint Stone Media

Episode 203: From An Immigrant with $100 To His Name, To a Successful Investor With a 30-Unit Portfolio Across Chicago with Catalin Maticiuc Mar 09, 2023

Show notes

Catalin Maticiuc of Compass joins us to share a wonderful immigrant success story involving house hacks on the North Side and BRRRRs on the South Side of Chicago!

Catalin talks about him immigrating to the United States and getting started in real estate! He speaks about the sleepless nights he had on his first house hack in Humboldt Park involving a FHA 203k loan to renovate that property. He goes on to talk about investing in Hegewisch, the adjacent neighborhoods, and why that model has worked for him. Catalin closes with motivating words on his goals and provides advice that investors of all experience levels will find useful!

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: Catalin Maticiuc, Compass

Link: SUCI Ep 53 - CHA Roundtable

Link: BRRRR Book by David Greene

Link: Brandon Moulton (Renovo Financial)

Link: Catalin's Instagram

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Guest Questions

04:19 Housing Provider Tip: Be mindful that source of income has been added to the Fair

03:18 Housing Provider Tip: Be aware of tax filing requirements set by lenders!

05:01 Intro to our guest, Catalin Maticiuc!

06:56 Catalin talks about his start in real estate!

17:25 What did Catalin do after his first house hack in Humboldt Park?

22:04 How did Catalin start investing in Hegewisch?

33:30 How has Catalin been able to scale?

41:37 What are Catalin's next goals?

45:34 What is Catalin's competitive advantage?

46:44 One piece of advice for new investors.

47:33 What do you do for fun?

48:08 Good book, podcast, or self development activity that you would recommend?

49:14 Local Network Recommendation?

49:45 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 202: Challenging Househacks with Sewer Lines, Evictions, and Gangs…Oh My! with Ben Sussman Mar 02, 2023

Show notes

Interested in learning how our guest has acquired 12 doors before age 30?! Although it may sound glamorous, Ben Sussman gives us a raw breakdown of the mistakes he's made and how he's rebounded strongly to continue growing his real estate portfolio!

Ben talks about his start in real estate and explains why he was attracted to the Belmont Cragin and Back of the Yards neighborhoods. He shares a horror story involving a broken sewer line in his first property along with lessons learned. Ben then turns up the horror level notch by discussing his second project where he inherited a gang-member tenant who threatened him with physical violence multiple times! He breaks down how he resolved the situation and how despite all the obstacles, those positives have far outweighed the negatives!

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: Ben Sussman, Exit Realty

Link: The Almanack (Book Recommendation)

Link: Retire Early with Real Estate Investing (Book Recommendation)

Link: Alan Sussman (Insurance Agent Facebook)

Link: Alan Sussman

Link: Ben's Instagram

Ben's email: bsussman123@gmail.com

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Guest Questions

04:19 Housing Provider Tip: Be mindful that source of income has been added to the Fair Housing Protected Classes and cannot be discriminated against!

07:50 Intro to our guest, Ben Sussman!

09:23 How did Ben get started in real estate?

13:28 Ben talks about the neighborhoods he started investing in and his first acquisition!

22:52 Lessons learned on Ben's first property!

25:12 Why did Ben go from Belmont Cragin to the Back of the Yards neighborhood for this second project?

33:18 Did Ben account for the added risk when acquiring his second property in a lower-class neighborhood?

38:05 How did Ben get out of the situation with his hostile, gang-member tenant?

42:39 Ben summarizes the lessons learned on this second property!

58:16 What is Ben's competitive advantage?

59:07 One piece of advice for new investors.

59:49 What do you do for fun?

61:15 Good book, podcast, or self-development activity that you would recommend?

62:07 Local Network Recommendation?

64:08 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 201: Owning Property in Your Personal Name or LLC Feb 28, 2023

Show notes

What are the advantages and disadvantages of owning a property in your personal name or in an LLC?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Bibek Das of Das Law

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Production House: Flint Stone Media

Episode 200: Which Chicago Neighborhoods are Hot and Which are Not? Feb 23, 2023

Show notes

WE'VE REACHED 200 EPISODES!!! Matt Feo, Jake Fugman, and Blake McCreight celebrate with us through an amazing panel discussion on all things Chicago Real Estate!

Are you curious on which areas of Chicago are next to double in value? Our panel provides their opinion. Local real estate trends is another topic discussed including golden tips on desirable property characteristics that will maximize your profits! To keep things balanced and realistic, overvalued neighborhoods and Chicago's biggest challenges are also addressed on this show. The crew closes with powerful words on why Chicago will continue to grow and attract investment - in short, we are a central hub and world class city that isn't going anywhere!

Listeners, thank you all for your continued support which has allowed us to reach this milestone!!!

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: Matt Feo, Blake McCreight, and Jake Fugman

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Guest Questions

03:26 Housing Provider Tip: Start a podcast and create a following!

04:22 Intro to our guests: Matt Feo, Blake McCreight, and Jake Fugman!

05:46 In what Chicago neighborhood would our experts invest $3 million?

09:32 Which Chicago neighborhood has the best chance for values to double in the near future?

18:44 Our panel discusses the most overrated Chicago neighborhoods!

27:53 What are some local Chicago real estate trends?

35:13 What are the biggest concerns for Chicago over the next 5 years?

41:37 What's the first step for new investors looking to get started?

47:41 Our panelists give suggestions to improve the SUCI podcast!

51:18 Chicago Fact time!

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Production House: Flint Stone Media

Episode 199: Lincoln Yards: A Sterling Bay Project Transforming Chicago Feb 16, 2023

Show notes

Matt Menna, Managing Principal of Sterling Bay, joins us to discuss Lincoln Yards; a 53-acre mixed-use community development along the North Branch of the Chicago River!

Matt kicks things off by talking about the history of the Lincoln Yards site and the process of acquiring that industrial land. He explains how Sterling Bay has been able to get input from all stakeholders on such a large scale development. Matt tells us how the 606 Trail will be positively impacted by this development and highlights the tremendous benefits that Lincoln Yards will bring to Chicago. He closes with powerful words on why Sterling Bay is bullish on Chicago and will continue development in our great city!

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: Matt Menna, Sterling Bay

Link: Devotion (Book Recommendation)

Link: Lincoln Yards Info

Link: Midwest RE Networking Summit

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Guest Questions

02:55 Housing Provider Tip: Have multiple exit strategies to mitigate risk on your next investment!

04:48 Intro to our guest, Matt Menna!

05:46 Matt gives the history of the Lincoln Yards location!

07:31 Matt explains the process of acquiring and aggregating the parcels!

10:15 How to get all stakeholders on the same page when planning a large scale development?

17:57 How has the community reacted to the planned Lincoln Yards development?

21:12 What is the 606 Trail and why is it relevant to Lincoln Yards?

27:15 Matt explains how it's been working with the City of Chicago!

32:06 How does the Fulton Market development relate to Lincoln Yards?

35:02 Did the pandemic cause any adjustments to be made during the planning of Lincoln Yards?

39:03 What benefits will Lincoln Yards bring to Chicago?

43:05 Why is Matt bullish on Chicago?

48:02 What is Matt's competitive advantage?

48:48 One piece of advice for new investors.

49:50 What do you do for fun?

50:15 Good book, podcast, or self development activity that you would recommend?

50:48 Local Network Recommendation?

51:52 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 198: 2023 Tax Strategies for Chicagoland Real Estate Investors with Michael Procaccio Feb 09, 2023

Show notes

It's that time of the year again - tax season is upon us! Michael Procaccio, a tax advisor and Chicagoland investor, joins us to provide insight on optimal tax planning to increase your bottom line!

Michael starts by explaining how he got into investing in franchises and kicked off his accounting career! He talks about the latest updates to the tax code and how investors can take advantage. Michael dives deep into the frequently missed deductions and mistakes that investors make. He breaks down the different tax statuses that can be held and addresses rapid fire tax questions from Tom and Mark!

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: Chicago's Prohibited Buildings List

Link: Susan Camiliere (Real Estate Agent Recommendation)

Link: Dave Schlueter (Attorney Recommendation)

Link: Rick Tayfel (Lender Recommendation)

Link: The Wealthy Gardner (Book Recommendation)

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Guest Questions

02:43 Housing Provider Tip: Utilize Chicago's Prohibited Buildings List for due diligence on short term rentals!

04:32 Intro to our guest, Michael Procaccio!

06:22 What attracted Michael to investing in franchises?

08:37 What advice would Michael give to someone new to franchise investing?

10:17 Why did Michael get into accounting?

12:12 What is new this year from an income tax perspective?

13:56 Michael explains tax changes relating to third payment softwares!

16:53 What are some commonly forgotten deductions by smaller scale landlords?

19:12 Michael explains the different types of tax statuses!

32:14 Tom asks Mike a series of tax related questions!

37:29 What are some other frequently missed tax items?

42:23 Are there new tax incentives for 2023?

45:27 What is Michael's competitive advantage?

46:03 One piece of advice for new investors.

47:04 What do you do for fun?

48:10 Good book, podcast, or self development activity that you would recommend?

49:05 Local Network Recommendation?

49:42 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 197: Four Mistakes To Avoid When Underwriting Multifamily Properties Feb 07, 2023

Show notes

What are the four main mistakes investors make when underwriting multifamily deals?

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Mike Morawski, My Core Intentions

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Production House: Flint Stone Media

Episode 196: Going A-to-Z on a Sight Unseen Purchase and Gut Renovation in Cicero with John Warren Feb 02, 2023

Show notes

John kicks things off by talking about underwriting, estimating rehab costs, and formulating the offer to purchase a multifamily building sight unseen. He explains Cicero point of sale inspection and the negotiation process. John then talks about the initial management and dealing with tenants involved in drugs and other criminal activity. Managing a blown rehab budget is another topic of discussion and John tells us how he handled it. This show is full of lessons learned on a heavy rehab of a tenant occupied building - take notes so you don't make the same mistakes!

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 of Forte Properties

Link: The Four Hour Workweek (Book Recommendation)

Link: Tools of Titans (Book Recommendation)

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Guest Questions

03:03 Housing Provider Tip: Be proactive about preventing frozen pipes during frigid Chicago Winters!

06:21 Intro to our guest, John Warren!

07:45 John introduces the deal that will be discussed on this show!

13:20 John talks about Cicero's point of sale inspection!

14:07 How do you calculate the rehab on a sight-unseen project?

26:29 What were the next steps after receiving the inspection report and closing on the property?

33:31 John talks about the initial management after closing on the property!

42:10 Why does Cicero outsource certain inspections?

43:24 Where did the additional rehab funds come from and what was the project's planned time frame?

51:11 Any lessons learned from the leasing process?

52:50 John talks about resolving the pest control issues.

58:42 Good book that you would recommend?

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Production House: Flint Stone Media

Episode 195: Building $300k in Networth through House Hacking (And Listening To The Straight Up Chicago Investor Podcast 😁) with Victoria Barkate Jan 26, 2023

Show notes

Victoria Barkate joins us to discuss how she has quickly scaled her rental property portfolio as a W2 employee!

Victoria starts by explaining her decision to move to Chicago specifically to invest in real estate. She talks about how she decided which neighborhoods to invest in and how she has utilized partnerships to scale. She dives into the ins-and-outs of her first couple house hacks including things that went well and challenges she faced. Victoria shares how she has learned to find off-market properties and how investors can take the low-inventory issue into their own hands. Throughout the show, Victoria emphasizes the importance of partnerships and building your network and demonstrates that putting in the work to learn investing can really pay off quickly!

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: Victoria Barkate, Accenture

Link: Mark's BP Blog on Tenant Scammers

Link: SUCI Ep 51 - John Westbrook

Link: SUCI Ep 138 - Mike Scanlon

Link: Managing by the Numbers (Book Recommendation)

Link: SUCI House Hacking Calculator

Brandon Smrz (Plumber Referral): 630-290-9238

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Guest Questions