

Straight Up Chicago Investor
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.
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.
Episodes
Mentioned books

Mar 23, 2023 • 1h 2min
Episode 206: Finding a Niche in Chicago New Construction Developments with Prashanth Mahakali and Fernando Lopez
Prashanth Mahakali returns to the SUCI Podcast (Episode 21) with his business partner Fernando Lopez to discuss all things related to New Construction Builds. Prashanth and Fernando discuss the formation of their partnership and their complementary skill sets. They explain how they've made the new construction design and development business model profitable. They dive deep on the level of customization they offer and share challenges they've faced when dealing with buyers. The duo tells us what areas and neighborhoods they are bullish on and planning new developments in! 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: Prashanth Mahakali and Fernando Lopez, Real View Design & Development Link: SUCI Ep 21 (Prashanth's Last Episode) Link: Alex Hormozi AI Video Link: Indistractable (Book Recommendation) Link: Darpet (Doors and Trim Vendor) Link: Hillside Lumber (Lumber Vendor) ----------------- Guest Questions 02:12 Housing Provider Tip: Change door locks between turnovers! 05:25 Intro to our guests, Prashanth Mahakali and Fernando Lopez! 07:36 Prashanth and Fernando discuss the formation of their partnership and their first deal together! 19:38 How to be profitable building new construction homes. 27:44 How custom are these new construction homes? 33:53 Prashanth and Fernando share challenges they've faced! 43:24 Software and/or Practices for tracking buyer customization. 44:55 What neighborhoods are Prashanth and Fernando focusing on? 51:38 The impact of interest rates on new construction home pricing. 53:03 What is Prashanth's and Fernando's competitive advantage? 54:07 One piece of advice for new investors. 55:19 What do you do for fun? 56:57 Good book, podcast, or self development activity that you would recommend? 57:41 Local Network Recommendation? 58:33 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Mar 16, 2023 • 52min
Episode 205: Be Your Own Bank And Grow your Investment Portfolio with Nick Chaplain
Nick Chaplain joins us to explain how real estate investors can leverage life insurance policies to "Be Your Own Bank". He jumps right into leveraging policies and building cash value as collateral for other investment opportunities. Nick explains how the wealthy take advantage of these strategies and their significant tax benefits. Mark also chimes in on how he has utilized this to help pay for his children's college! Tune in if you're interested in learning more about nuanced strategies to grow your net worth! 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: Nick Chaplain, Boston Cash Flow Financial Link: The Power of Zero (Book Recommendation) Link: Confessions of a CPA (Book Recommendation) Link: The Snowball (Book Recommendation) Link: Ash Wasilidas (Network Referral) ----------------- Guest Questions 04:00 Housing Provider Tip: Listen to the first 50 SUCI episodes! 05:30 Intro to our guest, Nick Chaplain! 08:06 The "Be Your Own Bank" Strategy! 09:27 Nick explains "compounding money"! 21:55 Different Types of Life Insurance Policies. 28:00 Mark shares his scenario of leveraging his Life Insurance Policy! 39:05 Strategies to Pay for the Annual Premium! 43:57 What is Nick's competitive advantage? 45:40 One piece of advice for new investors. 46:30 What do you do for fun? 46:55 Good book, podcast, or self development activity that you would recommend? 47:54 Local Network Recommendation? 48:08 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Mar 14, 2023 • 14min
Episode 204: Public Relations 101 - What to Say if a Reporter Contacts You Regarding Your Building
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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Mar 9, 2023 • 52min
Episode 203: From An Immigrant with $100 To His Name, To a Successful Investor With a 30-Unit Portfolio Across Chicago with Catalin Maticiuc
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 ----------------- 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Mar 2, 2023 • 1h 8min
Episode 202: Challenging Househacks with Sewer Lines, Evictions, and Gangs…Oh My! with Ben Sussman
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 ----------------- 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Feb 28, 2023 • 20min
Episode 201: Owning Property in Your Personal Name or LLC
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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Feb 23, 2023 • 55min
Episode 200: Which Chicago Neighborhoods are Hot and Which are Not?
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 ----------------- 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! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Feb 16, 2023 • 55min
Episode 199: Lincoln Yards: A Sterling Bay Project Transforming Chicago
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 ----------------- 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Feb 9, 2023 • 52min
Episode 198: 2023 Tax Strategies for Chicagoland Real Estate Investors with Michael Procaccio
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) ----------------- 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.

Feb 7, 2023 • 18min
Episode 197: Four Mistakes To Avoid When Underwriting Multifamily Properties
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 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.


