show episodes
 
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 importa ...
 
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show series
 
What does Chicago look like from an economist’ perspective and why should investors care? Today, Dr. Joseph Pagliari explains some of his economic thesis related to Illinois’ long term fiscal issues that are top of mind for so many investors. He provides options Illinois might have to address these issues, but are they specific to only Chicago or a…
 
What are some common mistakes that cause investors to overpay for an investment property? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano | ClickInvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.…
 
The word "taxes" inspires fear from all types of investors, but especially in Chicago. From income tax, to property tax, we’re paying a lot. Depreciation is one of Real Estate’s greatest benefits, and there is a way to maximize that benefit immediately. Cost Seg Kev is here today to explain what cost segregation is and how it can be used to offset …
 
One of the most important allies to an investor is the broker they work with. Gloria Weikert runs the X-Plus team and has a specialty in helping clients buy investment properties. In today’s episode, Gloria gives some insight on what it takes to win deals in a competitive market that go past just offering more money; breakdowns of different neighbo…
 
Chicago is known for complex and restrictive landlord and tenant policies, but there are dozens of people fighting for change and protection. Kris Anderson of the Chicago Association of Realtors is one of those people on the front lines. Not everyone knows the role of CAR, so Kris explains what they do and his role in the machine as well as other g…
 
Elgin has a long history of being one of the most significant cities located just outside of Chicago. Spanning two counties and one of the largest populations in Illinois, it offers a wide variety of housing options and investment strategies. Broker and investor, Mike Zwemke, takes us through his experiences of getting started and scaling in the ar…
 
Lumi Ispas has been a determined and successful investor, broker, and coach in Chicago for two decades. She’s lost it all and gained it all back. In today’s episode she shares her journey of emigrating from communist Romania to truly experiencing the American Dream through real estate. She addresses several hot topic items including early mistakes,…
 
Many fear what they don’t understand. That’s exactly why we put together this round table discussion with two other great CHA section 8 property managers. Listen in as we address the entire workflow from screening the applicants, to the move in, and everything that happens in between. Section 8 can be a great investment strategy, but it’s imperativ…
 
It’s March and taxes are top of mind! However, by only reactively focusing on taxes during this one part of the year, you are potentially leaving money on the table. Aaron Zimmerman, a Chicago investor and CPA, provides great insights into how to best work with a CPA, the importance of maintaining good records, overlooked deductions, and proactive …
 
Would you trade salary for knowledge? John Westbrook spent time straight out of college working for one of Chicago’s largest property managers to build-up his foundational knowledge of the industry. John has since transformed this knowledge into a substantial portfolio of multifamily buildings on the Northside. John explains how he plans for the lo…
 
For our 50th episode we thought we’d give everyone a special treat... Andrew Holmes is one of the most well-known names in Chicago Real Estate Investing. Andrew explains his incredible journey, from his early days as a hustling agent, to how he structured his first few investment deals. Andrew dives into specifics on how he finds deals, what attrib…
 
For the past 15+ years, Rosario Terracciano has been cutting his teeth with a lot of hard learned lessons. In today’s episode, he shares some early mistakes he made about buying, working with contractors, estimating ARVs and leasing. He shares how he weathered the sub-prime crisis and emerged stronger - co-founding Clickinvest and ultimately repres…
 
For everyone working a W2 job, our guest today, David Shifrin, is a great example of how to incorporate real estate into your long-term plan without having to give up your current career. David Shifrin wanted a way to marry his professional career as a plastic surgeon to his interests in becoming a real estate investor. This path led him to Motor R…
 
The term “1031 Exchange” is ubiquitous, but do you really know what it is or how to even engage in one? Lauren Speidel of Exeter1031 is a subject matter expert and breaks it down for you today. She’ll explain the different parties involved, what the criteria are and what you need to know before having the necessary conversations. Our hosts, Tom and…
 
Chicagoland is an enormous market with a ton of sub markets. Anthony Citriglia of Essex Realty’s submarket covers many of the near north and near northwest suburbs and he breaks down exactly what those markets are like; how they differ from Chicago; and how they differ from each other. Following the post-war boom, cheaper access to cars, and the de…
 
For over 35 years, Jack Crane has been providing expertise on financing the acquisition and rehabilitation of commercial real estate. The majority of those years have been spent as Sr. VP of lending at CIC where he is responsible for carrying out the mission to be a leading force in both neighborhood revitalization and affordable housing. From lend…
 
How many ways are there to finance buying a property? Way more than I’m aware of which is why our guest Chris Puleo is here. With his robust 20+ year career, Chris has seen it all and explains a plethora of different popular products. With so much interest in househacking, of course we talk about the FHA product and calculating the self sufficiency…
 
Have you ever looked at your significant other and wanted to build an empire with them? That’s exactly what Nicky and RJ De Leon have been doing since the early days of their relationship. Today, they tell their story from start to current day, diving into how they had all those hard conversations about deciding on the first location, getting on th…
 
In today’s episode, attorney Bob Floss dives further into the current RLTO ordinances and how the proposed ordinance affects investors, landlords, and tenants alike. With so much changing day to day, it can be challenging to keep track of best practice. This is why it’s necessary to have solid legal representation on your team when dealing with ten…
 
As we wrap up 2020, a huge thank you to all our listeners and active participants that have helped transform this podcast from a simple idea of sharing localized knowledge into its current state (which we view as a success). In this episode, Mark and Tom give a quick state of the union of the podcast and also dive into what they learned over 40 epi…
 
Tom Raleigh, of Halsted Law Group, breaks down the current environment for landlords as it relates to the eviction process. COVID has shaken things up, and understanding what you can and can’t do is more confusing than ever, so having an ally who understands the rules and will fight for you is paramount. Listen to our hosts ask Tom some FAQs about …
 
In today’s episode, Sean Connolly talks about his not so usual journey of scaling to a multi- million dollar portfolio and the lessons and tools he’s acquired over the past 8 years. Sean provides his advice on investing in certain southside markets as a new investor and if you’re not doing volume, why it’s so important to control your material cost…
 
Are you looking for distressed deals? The Cook County Land Bank (CCLB) has plenty and they go right under most investor’s noses! In today’s episode, Rob Rose provides an overview of the CCLB, a socially responsible wholesaler working with investors to turn dilapidated properties into newly remodeled homes. Rob describes CCLB’s acquisition process, …
 
In today’s episode, our guest Mike Glasser, President of the Neighborhood Builders Owner Alliance, explains how neighborhood housing provider advocacy groups are fighting for fair and lawful protection for investors in and around Chicago. Mike lays out the current advocacy campaign against the proposed CRTLO, the differences between the CRLTO and t…
 
First and foremost, a huge thank you to all our listeners! Please continue to be active members of our community and help spread the good word! This Thanksgiving, we want to take a quick moment to reflect on all the great things and opportunities we have in this great city of Chicago. A rich history, epic sports franchises, an extensive park networ…
 
Jon Womack of Third City Properties has been investing in the Chicago market for four years focusing on the northwest neighborhoods of Belmont Cragin and North Austin. Jon dives into what the investment landscape looks like in these areas, including tenant expectations of finishes and his general investment strategies. One of the key differentiator…
 
With the right mindset, anything can be achieved. Shantanu Kamra is living proof, having moved to the US 8 years ago and Chicagoland just about 2 years ago, he’s been able to scale his portfolio in the western suburbs to over 40 units. In today’s episode he talks about househacking, BRRRR strategy execution, and scaling into larger buildings. He al…
 
Are you interested in multifamily buildings in the southside of Chicago? Are you looking to know the ins and outs of Bronzeville along with some of its adjacent neighborhoods? Ted Stratman is one of the leading brokers in Chicago and in this episode he lays out invaluable block by block knowledge - including what rents have done over the last twelv…
 
Luke Blahnik of Flor Blahnik, is a true real estate entrepreneur (and owner of Avondale Bowl!). In this episode, Luke provides block by block insights investors need to know to successfully invest in Logan Square. He explains what attracted him to the area as well as the future prospects for growth despite the massive run up over the past 10 years.…
 
“You have to watch out for your property taxes,” has been said in numerous episodes. On today’s episode we bring a tax appeal expert to explain how to proactively protect your investment against increasing property taxes. Tim Jacobs of KSN Law dives deep into the complex world of Illinois property taxes and about the multiple ways you can appeal pr…
 
In this week’s episode, Sean Morrissey of Chicago Realty Group LLC breaks down investing in and around Aurora, focusing on the downtown redevelopment taking place to bring the old riverboat city back into the spotlight. Aurora is full of diverse opportunities, including tax credits, and unique zoning discrepancies that allow the clever investor the…
 
Ciere Boatright is the VP of Real Estate and Inclusion at CNI and has managed the planning and development of over $350 Million in new investment in southside neighborhoods. Today, Ciere walks us through several of those projects, with a focus on CNI’s successful revitalization of Pullman. Ciere explains CNI’s approach towards creating jobs and aff…
 
There are over 125,000 RE/MAX agents in the US, and in 2019 not one of them sold more properties than REO expert Ryan Smith. That’s right, our guest is #1 out of 125,000. In this episode, Ryan Smith and his partner Mike Harvey discuss REO properties, how to work with REO agents, and the difference between foreclosure and pre-foreclosure. Ryan and M…
 
Jason Marcordes, owner of Landmark Property Management, provides insight into how Pilsen has evolved and why he thinks it still has a runway for growth. Jason dives into tenants expectations and several nuances that come with investing in one of the oldest neighborhoods in the city. Aside from Pilsen, we touch on surrounding neighborhoods such as L…
 
Neal Bawa, the founder of Grocapitus, has built an immense empire of 3,000 units with nearly 40,000 students studying his data driven approach. On today’s episode, Neal dives into the key advantages and disadvantages of investing in Chicago compared to other major metros. He also provides his thoughts on opportunity zones, including the major benef…
 
Today’s episode provides great insights for anyone investing in Chicago, specifically for those unfamiliar with the area. Author, coach, and entrepreneur Kathy Fettke has been featured on The Wall Street Journal, ABC, CNBC, NPR, MarketWatch, among other major media outlets. With over 50,000 members following her advice through her RealWealth Networ…
 
Chance Badertscher from Lavelle Law, specializes in Commercial and Residential real estate as well as business formation in and around Chicagoland. In this episode, Chance provides nuggets on how to properly interview a real estate attorney and how an attorney should quarterback your transaction. Chance also goes into the role the attorney plays in…
 
Our guest today, Noah Birk, is the highest producing multi-family broker in Chicago since 2014. In this episode, Noah provides great hyper-local insights on MFH investing in neighborhoods like South Shore, Auburn Gresham, Washington Park and Englewood. We discuss the impact that the Obama Center and Tiger Woods Golf Course play into the area’s appr…
 
Matt Fritzshall is the President and Founder of Triton Realty Group with over 200MM in transactions under his belt. Matt was highly successful during the Logan Square boom and in this episode, he'll discuss other Northside markets such as Hermosa and Belmont Gardens that have the potential to be the next Logan Square. Matt also weighs in on the age…
 
Prashanth Mahakali is the owner of PMPC Architecture firm here in Chicago and an active contributor to Bigger Pockets. He is also an investor and has built his firm under the notion of smoothly handling all headache permits for his clients. In today’s episode, Prashanth talks in depth on handling building violations, expediting permits, and navigat…
 
After selling a successful logistics company, and actively investing in real estate, Jake Fugman has carved a niche as a high-performing investor-friendly agent. In this episode, Jake provides a ton of market knowledge and deep insights into many desirable and upcoming Chicago neighborhoods, including Hermosa, Belmont Gardens, Portage Park, Marshal…
 
Last week we got into the top ten mistakes borrowers make with Renovo Financial. This week, Eric Workman continues counting down the top 10 with numbers 5 all the way down to #1. Eric has a long background in real estate with experience in construction, brokering deals, flipping houses, etc. When Brandon Moulton, our guest from the previous episode…
 
You've heard their name tossed around on earlier episodes, and now we have Renovo Financial here to address some of the biggest mistakes they see when dealing with Chicagoland investors. Brandon Moulton is the Senior VP of Lending at Renovo Financial and has been featured on Crain's Chicago People on the Move. Brandon takes on Part 1 of the top ten…
 
Local real estate and commercial litigator, Bibek Das, has spent the last 20+ years educating and protecting Chicagoland investors and landlords. In this episode, Bibek drops a ton of knowledge (and NUGGETS!) to ensure you are running your real estate business appropriately. This includes an overview of Chicago's Residential and Landlord Tenant Ord…
 
After a successful career in corporate finance, Eric took his skillset (which he originally honed at THE University of Illinois) and transitioned full-time into real estate. Eric is a co-founder of 33 Realty, a vertically integrated company that has the ability to takes its clients through the entire lifecycle of a real estate investment. In this e…
 
John Casmon is a successful Chicago househacker turned syndicator and the founder of Casmon Capital Group. In addition, John hosts the Target Market Insights Podcast, heads up the Chicago Multifamily Club Meetup, and is the co-creator of the Midwest RE Networking Summit (coming up on 7/25-7/26). In this episode, John provides a wealth of knowledge,…
 
One doesn't accomplish $600,000,000 in real estate transactions without thoroughly understanding the ins and outs of the business and which neighborhoods are primed for sound investments. Our guest today, Brian Kochendorfer, has a ton of nuggets to drop from his experience as a broker, passive investor, and managing member of Arc Equity Group, wher…
 
There's a reason Ben Walhood has already been a featured guest on numerous high-profile podcasts, including Bigger Pockets, The Best Ever Real Estate Podcast with Joe Fairless, Target Market Insights with John Casmon, and has been interviewed by CNBC and The Chicago Tribune. Over the last decade, Ben has consistently grown his portfolio in Dupage C…
 
With 20 years in the business, Joe Mueller got his start buying REO (bank owned) properties at auctions. From there, Joe networked extensively to develop a robust acquisitions strategy and eventually implement multiple streams of income. Most recently, Joe started a title company suited for investors who wanted to transact in off market property wi…
 
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