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...
Be sure to visit the podcast's website and support the creator: www.straightupchicagoinvestor.com
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Straight Up Chicago Investor
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Podcast website
Latest episode
Oct 1, 2026
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Episodes
Episode 211: Peeling Back The Onion on Student Housing In Chicago 13.04.2023 54:57
Interested in investing near a Chicagoland University to provide student housing?! Harrison Cohen joins us to share how he's built his portfolio using this model! Harrison explains why he decided to focus on student housing and the nuances of student housing near different universities, including University of Chicago, UIC, DePaul, and Loyola. Harrison dives deep on the leasing process and how it...
Episode 210: What Investors Can Expect From Signed Contract to Finished Rehab 11.04.2023 11:07
What should I expect when I hire a contractor for my first remodel? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Matthew Nosal, NEGC Remodeling ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.
Episode 209: Building a Portfolio with New Construction Rentals, STRs, and MTRs with Chicago REIA's Andrew Holmes 06.04.2023 57:05
Do short term, mid term, and new construction rentals interest you?! Andrew Holmes provides great insight on how he's been utilizing all of these investment vehicles to grow his portfolio! Andrew kicks things off by discussing the differences between today's real estate market and the 2012 market when he got started in real estate. He transitions into the new construction development that he and h...
Episode 208: Going Deep in Bucktown and Wicker Park with Jason Stratton 30.03.2023 48:52
Interested in investing in Chicago's Bucktown neighborhood, but wondering if you're too late to the party?! Jason Stratton joins us to provide his perspective as a seasoned realtor, investor, and resident of the neighborhood. Jason starts by sharing what attracted him to Bucktown and his first deal. He defines the street borders of Bucktown, the amazing attributes of the neighborhood, and shares h...
Episode 207: The Steps to Estimating and Strategizing a Light Rehab or Turnover 28.03.2023 13:04
What must an investor consider when planning to work with a contractor? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Matthew Nosal, NEGC Remodeling ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.
Episode 206: Finding a Niche in Chicago New Construction Developments with Prashanth Mahakali and Fernando Lopez 23.03.2023 1:01:40
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 customi...
Episode 205: Be Your Own Bank And Grow your Investment Portfolio with Nick Chaplain 16.03.2023 52:25
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 h...
Episode 204: Public Relations 101 - What to Say if a Reporter Contacts You Regarding Your Building 14.03.2023 14:09
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.
Episode 203: From An Immigrant with $100 To His Name, To a Successful Investor With a 30-Unit Portfolio Across Chicago with Catalin Maticiuc 09.03.2023 52:19
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 goe...
Episode 202: Challenging Househacks with Sewer Lines, Evictions, and Gangs…Oh My! with Ben Sussman 02.03.2023 1:07:47
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 horr...
Episode 201: Owning Property in Your Personal Name or LLC 28.02.2023 19:44
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.
Episode 200: Which Chicago Neighborhoods are Hot and Which are Not? 23.02.2023 54:34
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 yo...
Episode 199: Lincoln Yards: A Sterling Bay Project Transforming Chicago 16.02.2023 55:07
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 de...
Episode 198: 2023 Tax Strategies for Chicagoland Real Estate Investors with Michael Procaccio 09.02.2023 52:25
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. Michae...
Episode 197: Four Mistakes To Avoid When Underwriting Multifamily Properties 07.02.2023 18:17
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.
Episode 196: Going A-to-Z on a Sight Unseen Purchase and Gut Renovation in Cicero with John Warren 02.02.2023 1:01:53
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 discussi...
Episode 195: Building $300k in Networth through House Hacking (And Listening To The Straight Up Chicago Investor Podcast 😁) with Victoria Barkate 26.01.2023 46:25
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...
Episode 194: Understanding Chicago Garages with Vince Sliwa 24.01.2023 14:15
What do I need to know when fixing or building a garage in Chicago? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Vince Sliwa, A-Windy City Garage Corporation ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.
Episode 193: The 2023 Guide to The Chicago Eviction Process with Jessica Ryan 19.01.2023 1:05:08
Jessica Ryan, Head of KSN's Landlord/Tenant Department, joins us to educate Chicago Landlords on the eviction process and best practices! Jessica begins by explaining the first step in the process; properly serving a 5-day notice. She talks about utilizing process servers for notices and summarizes the filing fees associated with an eviction. Jessica then gives a detailed breakdown of the phases o...
Episode 192: Scaling Up In Albany Park, Lincoln Square, and Ravenswood with Nick Yassan 12.01.2023 52:21
Nick Yassan, President of Rany Management, grew up in a family of real estate investors and has been instrumental to growing his company's real estate portfolio! Nick begins by explaining how he was involved in real estate from an early age and the competitive advantage that it has given him. He shares what the 2008 housing crash was like and how that impacted his real estate investing. Nick jumps...
Episode 191: Understanding Your Insurance Premium and Potential Money Saving Credits 10.01.2023 14:50
What goes into an insurance premium and what are some items investors should look out for? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann , State Farm Insurance Link: Investor Stories Featuring Sean Morrisey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.
Episode 190: Everything Chicago Investors Need to Know About Logan Square with Luke Blahnik 05.01.2023 58:04
Real Estate Broker, Developer, and Entrepreneur Luke Blahnik joins us to discuss his neighborhood of expertise: Logan Square! Luke knows the neighborhood block by block and outlines some of the premier streets that feature phenomenal housing stock on oversized lots. Luke elaborates on the different pockets of the neighborhood including the higher priced areas around the Boulevards and other more a...
Episode 189: How To Underwrite Chicago Multifamily Buildings with Essex Director Rick Ofman 29.12.2022 58:50
Rick Ofman has over six years of experience in commercial real estate and is a Director at Essex Realty Group. Rick kicks things off by defining underwriting and associated terminology. He provides a thorough breakdown of income, expenses, and necessary assumptions. Rick shares insight on forecasting variables such as rehab costs, rent increases, and tax increases to name a few. He explains some v...
Episode 188: Forewarn - A Powerful Tool to Validate Personal Information and Criminal History (and it's free for most Chicago agents!) 27.12.2022 13:14
What is Forewarn? How does it benefit agents and housing providers and how can I utilize the tool? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Megyn Christensen, Forewarn ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 187: Department of Housing Commissioner Marisa Novara; Moving Chicago Forward 22.12.2022 1:03:34
Marisa Novara was appointed as Commissioner of the Department of Housing (DOH) in 2019 and has since led the creation of policies to promote equitably distributed affordable housing across the City. Commissioner Novara starts by explaining the purpose of the DOH. She dives deep on a fascinating study on segregation across the City that her team conducted. She speaks to the results of the segregati...
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