

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

Feb 22, 2022 • 12min
Episode 123: Straight Up Tuesday Tip 23 - Rosario Terracciano Answers "What should buyers expect in 2022?"
What should buyers expect in 2022? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano from Clickinvest Link: AttomData.com ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Feb 17, 2022 • 52min
Episode 122: A Case Study on Three Chicagoland Deals in a Low-Inventory Environment with John Warren
Can't find a deal in this Chicago Real Estate Market? You are not alone! John Warren of Presto Properties joins us to discuss how he acquired his 3 most recent properties. John discusses properties he purchased in Bellwood, Albany Park, and Cicero. He shares how he acquired each deal, the strategy implemented, the nuances, and lessons learned. While breaking down the deals, John elaborates on partnerships, stabilized vs. value-add properties, and how he is growing his team to continue to scale efficiently. Lots of golden nuggets in this episode from one of Chicagoland's finest! 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 from Presto Properties Link: Get Rich Education Podcast Link: Yan Pesotskiy LinkedIn (Local Network Recommendation) Sponsors: GC Reality and Kiser Group ----------------- Guest Questions 03:18 House Provider Tip: Use the time-stamp camera app! 04:50 Intro to our guest, John Warren! 07:30 Deal #1 - How did John find his Bellwood deal? 09:29 Why did John sell his previous building and use a 1031 exchange to buy the Bellwood building? 11:40 How did John get familiar with Bellwood and what went into the due diligence process? 13:03 What's the permitting process like in Bellwood? 14:35 What were the lessons learned on the Bellwood property? 15:55 Deal #2 - How did John find his Albany Park deal? 17:25 What are the main differences between buying stabilized properties compared to value-add properties? 18:43 What are some things to consider when determining whether or not to enter into a partnership?. 20:50 How is John structuring his partnerships? 21:39 What was John's outlook when recently making the decision to buy a stabilized multi-family compared to value-add? 24:40 Is John outsourcing management or keeping it in-house? 27:17 What were the lessons learned on the Albany Park property? 28:57 Deal #3 - How did John find his Cicero deal? 30:42 What was the background on the deal? 31:48 How did John assess the risk of buying the building sight unseen? 33:00 What are the numbers on this deal? 35:42 How has John handled tenants when coordinating the heavy rehab of the building? 37:00 How to get existing tenants to relocate when they are currently paying substantially below market rent? 39:45 What were the lessons learned on the Cicero property? 41:25 What are John's plans for his local meetup in 2022? Wrap Up Questions 43:00 What is John's competitive advantage? 46:33 One piece of advice for new investors. 47:04 What do you do for fun? 47:28 Good book, podcast, or self development activity that you would recommend? 48:00 Local Network Recommendation? 48:42 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Feb 10, 2022 • 52min
Episode 121: Breaking Down Why Chicago Public Housing Failed with Professor Brad Hunt
Dr. Brad Hunt of Loyola University's Department of History joins the show to educate us on the complicated history of Chicago's Public Housing developments and why real estate investors should care. Brad is the author of Blueprint for Disaster, in which he traces Chicago's Public Housing history and transformation under various government administrations. Leveraging this knowledge of poorly operated public housing in Chicago, Brad is able to share what he would do differently and how investors can use this knowledge to be better housing providers. 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: Brad Hunt, Loyola University Chicago Department of History Link: Blueprint for Disaster: The Unraveling of Chicago Public Housing Link: Loyola University Chicago's Department of History Sponsors: Pentwater Cabinetry and Kiser Group ----------------- Guest Questions 02:25 House Provider Tip: Thoroughly screen tenants and ask for additional documentation (tenant will always provide info that makes them look good)! 05:30 Intro to our guest, Brad Hunt! 06:38 How did Brad select his career path? 08:38 What is the high-level overview of Brad's book, Blueprint for Disaster, and why did he write it? 13:00 What are some examples of "cost-cutting" used in Chicago Public Housing that had significantly negative impacts? 16:10 How did Public Housing begin to get a negative stigma? 20:54 How did screen changes impact the feel of Public Housing? 22:50 What tenant mix would be ideal to optimize how Public Housing runs? 26:20 How did Chicago Public Housing maintenance costs compare to other cities? 34:13 What was going on in Public House leading up to the crack cocaine epidemic in the 1990s? 40:50 Why are certain Public Housing developments being preserved while others have been torn down? 42:52 What would Brad change about the way Public Housing is run today? Wrap Up Questions 45:44 What is Brad's competitive advantage? 46:04 What is the one piece of advice for new investors looking to buy their first property in Chicago? 46:31 What do you do for fun? 47:12 Good book, podcast, or self development activity that you would recommend? 48:34 Local Network Recommendation? 49:42 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Feb 8, 2022 • 11min
Episode 120: Straight Up Tuesday Tip 22 - Perry Farella Answers "What are the new 2022 conventional and FHA loan limits?"
What are the new 2022 conventional and FHA loan limits? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Feb 3, 2022 • 38min
Episode 119: How Blockchain is Impacting Chicago Real Estate with Simon Enwia
Thinking about buying Real Estate or a Yacht in the Metaverse? Want to learn more about the Metaverse, Blockchain, and other innovations that will impact your real estate strategy? This episode will scratch that itch! Simon Enwia of Flawless Homes shares mind-blowing insight on developing technologies in real estate! Before jumping in, Simon lays out his background as a Chicago investor and breaks down the nuances and hidden-value in mixed-use buildings. He then transitions into the concept of Tokenization and how this will affect the general public. Simon closes out by explaining Real Estate in the Metaverse and what we can expect to see in the future! 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: Simon Enwia, from Flawless Homes | LinkedIn Sponsors: Kiser Group and ClickInvest ----------------- Guest Questions 02:45 House Provider Tip: Stop using mailboxes with keys if possible! 04:20 Intro to our guest, Simon Enwia! 05:10 How did Simon start investing in Chicago? 06:19 What was the first big "scary" project that Simon worked on? 08:06 What are the nuances of mixed-use buildings? 10:45 How did Simon get into mixed-use buildings? 12:00 What is the history of Flawless Homes? 12:57 Why should investors care about Blockchain and does it impact real estate? 16:13 How will Blockchain impact real estate agents and brokerages? 19:00 What is the potential of Blockchain in the real estate market? 20:34 What is the definition of Blockchain? 22:34 What is Tokenization? 24:41 How will Tokenization help the general public and their ability to get involved in real estate? 25:46 How are "Tokens" different from shares or stocks? 26:55 What are some real estate inefficiencies that will get eliminated because of Blockchain and other technologies? 28:35 What other technological advances should investors be mindful of? 29:50 What is the Metaverse in real estate? 31:41 Simon's final thoughts and tips on real estate in the current market and moving forward. Wrap Up Questions 32:58 What is your competitive advantage? 33:17 What is the one piece of advice for new investors looking to buy their first property in Chicago? 33:27 What do you do for fun? 34:07 Good book, podcast, or self development activity that you would recommend? 34:29 Local Network Recommendation? 34:58 How can the listeners learn more about you and provide value to you? Thanks for tuning in! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 27, 2022 • 59min
Episode 118: From Derivatives Trading to Chicago Real Estate Investing and Brokering with Lawrence Dunning
New development strategies, hot Chicago areas, derivative financing trading, long-term holds, and an Englishman! This episode is packed with nuggets across the board. With a background in finance and derivatives trading, Lawrence Dunning has shifted his analytical skills to real estate and is making a name for himself by linking developers to long-term investors before inventory hits the market. Lawrence explains how the pandemic has affected the economy and real estate in Chicago. We had him drop street-level knowledge on areas that he's bullish on and directing his buyers towards. He also talks about the value of new construction buildings and how they compare to rehabbed buildings. He closes out the episode with how to project taxes on new construction and some pretty amazing stories on his background! 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: Lawrence Dunning, Main Street Real Estate Group Link: Lawrence Dunning LinkedIn Link: Enter the Lionheart Podcast Sponsors: Kiser Group and ClickInvest ----------------- Guest Questions 03:37 House Provider Tip: Be sure to check up on properties during these frigid cold days/weeks of the year! 05:47 House Provider Tip: Intro to our guest, Lawrence Dunning! 06:58 How has the pandemic impacted our economy and the asset classes? 08:41 Why did Lawrence choose to dive into real estate out of all the asset classes? 13:54 In retrospect, what areas of the city and what types of real estate had noticeable changes as a result of the pandemic? 15:50 What is Lawrence's business model and what areas is he focusing on? 19:08 How is Lawrence finding inventory for his clients in hot areas like Pilsen? 22:58 Where would Lawrence take a new investor who can't buy a new construction, but is looking for a solid but attainable investment? 25:15 Who is buying new construction buildings and how does new construction compare to rehabbed buildings? 28:50 What other areas is Lawrence seeing with good investment opportunities? 33:50 What are some signs or things to look for in an area that is or will be experiencing development? 38:54 What is the approximate cost per square foot of new construction? 41:18 How to estimate taxes on new construction? Wrap Up Questions 47:21 What is Lawrence's competitive advantage? 48:32 What is the one piece of advice for new investors looking to buy their first property in Chicago? 49:57 What do you do for fun? 52:10 Good book, podcast, or self development activity that you would recommend? 54:18 Local Network Recommendation? 55:45 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 25, 2022 • 13min
Episode 117: Straight Up Tuesday Tip 21 - Blake McCreight Answers "As a buyer, how can I find wholesalers, get them to work with me, and what should I expect throughout the process?"
As a buyer, how can I find wholesalers, get them to work with me, and what should I expect throughout the process? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Blake McCreight of Express Property Solutions ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 20, 2022 • 38min
Episode 116: CAA's Advocacy and Education for Chicagoland Housing Providers with Tom Benedetto
On today's episode, our guest Tom Benedetto explains how the Chicagoland Apartment Association (CAA) is a strong voice in the fight for fair and lawful protection of Housing Providers across Chicagoland. Tom shares CAA's mission statement, the issues they are currently tackling, and the biggest challenges in the push for advocacy. Lastly, Tom closes with the goals that CAA has for the near future and how investors can get involved to support the fight. Listen in and if you find value in today's episode, please leave us a 5-star review and recommend us to a friend! Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Tom Benedetto, Chicagoland Apartment Association Link: Freakonomics Podcast - Why Rent Control Doesn't Work Link: Shape Illinois - Supporting Housing Affordability, Progress, and Equality Link: The On-The-Way Delivery Platform | Roadie, A UPS Company Sponsors: Kiser Group and ClickInvest ----------------- Guest Questions 03:16 House Provider Tip: Setup keys or electronic access for maintenance purposes to avoid unnecessary trips to your property. 06:30 What is the CAA? 08:04 What does CAA do for investors? 09:43 At which point does it make sense for an investor to become a member of CAA? 10:44 What makes you passionate about this work? 12:39 What issues does CAA advocate for and take a lead on? 14:06 How does CAA work alongside other real estate advocacy organizations? 18:39 How do the recently passed Rent Control Referendums in the Twin Cities impact CAA's work? 19:49 What is Rent Control and what are the real reasons investors are against it? 21:38 What are the main topics/issues that CAA is currently focusing on? 23:15 How is CAA effectively communicating with busy legislators to ensure they are being heard? 24:51 What are the biggest challenges that CAA faces during their daily work? 26:40 What other resources does CAA have that investors could use for education? 28:40 What would Tom like to see CAA accomplish 5 years from now? Wrap Up Questions 31:04 What has been your competitive advantage? 31:50 One piece of advice for new investors. 32:29 What do you do for fun? 33:30 Good book, podcast, or self development activity that you would recommend? 34:37 Local Network Recommendation? 35:25 How can the listeners learn more about you and provide value to you? That's our show! Thanks for tuning in! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 13, 2022 • 56min
Episode 115: The Current State of Chicago's Northside Real Estate Market with Managing Broker Brie Schmidt
Wondering if it's time to jump into the Chicago Real Estate Market? Brie Schmidt provides a recap of the 2021 market and dives into the current trends and expectations for 2022. Brie explains how low inventory has impacted the market and how buyers have had to readjust their expectations. She also discusses lending challenges on properties in her area of expertise, Chicago's North Side. Brie drops street-level knowledge on neighborhoods and how buyers in different life stages are choosing where to invest. 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 of Second City Real Estate Link: Getting Things Done (Book Recommendation) Sponsors: Kiser Group and Pentwater Cabinetry. ----------------- Guest Questions 00:58 Negotiation tips to facilitate your transactions. 04:17 House Provider Tip: Choose a discreet location for your lockboxes to avoid break-ins! 06:50 What was the most surprising part of 2021? 09:30 How have buyers been reacting to the lack of inventory and how is inventory today? 12:20 How is Brie handling buyers and helping them purchase investment properties during a hot seller's market? 18:28 What is the common dilemma buyers wrestle with in this seller's market and what's an alternative perspective they can take? 21:00 How is the conversation on a purchase different when comparing house hackers to straight up investors? 23:10 How have lending and rates changed during this hot market and the pandemic? What have been some of the challenges? 27:17 What neighborhoods saw the largest growth in 2021? 30:30 How have some fringe neighborhoods changed over recent years? How do buyers reset their tenant expectations in these areas? 34:38 Considerations investors should have when analyzing buildings with deferred CapEx and maintenance. 36:26 What are Brie's thoughts on the City's issues with taxes, pensions, and crime? 43:42 Other perspective changes buyers can/should make in today's market? 46:51 What neighborhoods are over-inflated? Wrap Up Questions 48:57 What is Brie's competitive advantage? 49:34 One piece of advice for new investors. 50:27 What do you do for fun? 51:58 Good book, podcast, or self development activity that you would recommend? 52:20 Local Network Recommendation? 53:48 How can the listeners learn more about you and provide value to you? That's our show! Thanks for listening! ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.

Jan 11, 2022 • 12min
Episode 114: Straight Up Tuesday Tip 20 - Perry Farella Answers "How are lenders handling ADU requests from investors looking to add a legal unit to an existing property?"
How are lenders handling ADU requests from investors looking to add a legal unit to an existing property? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending | Perry's Blog ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.


