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 are the steps and my responsibilities as an investor to get from attorney review to the closing table? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chance Badertscher of Lavelle Law ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Inves…
 
Roman Viere manages and operates over 900 apartment units, and the majority of these units are in Austin. Austin is geographically Chicago’s largest neighborhood and offers everything from a 9-hole golf course to struggling store fronts. It takes a hands-on approach to analyze, screen and operate in a neighborhood like Austin, and Roman provides ta…
 
Like many real estate professionals, Jonathan Klemm transitioned from a W-2; what is remarkable about him is his background working with Walsh Construction, which is one of Chicago’s largest construction and contraction companies. Jonathan has taken everything he learned about managing large scale projects and applied it to smaller, investor focuse…
 
What are proactive steps to ensure I'm ready to pull the trigger when the right property presents itself? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Rosario Terracciano of Clickinvest ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Invest…
 
With the Lake, a world-class University, and a plethora of transportation, Evanston is an extremely attractive and diverse marketplace for many investors. Jaimie Steinher of Essex Realty exclusively covers Evanston, and provides on the ground insights to help you navigate the different pockets of the city. Jamie lays out cap rates, average rents, a…
 
For many Chicagoans, the porch has been the focal point of countless memorable times. Since Covid, the importance of “outdoor spaces” in real estate has re-emerged as a priority for plenty of homebuyers, too. But how many investors know how to evaluate the build quality of a property with a porch? And what’s the process like when wanting to add a b…
 
What are some common mistakes I can look to avoid when calculating my after repair value and proposed rents? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Warren of SecondCity ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 202…
 
We all know about the numerous laws either being proposed or already enacted affecting housing providers and investors. Groups like the Illinois Realtors Association, the NBOA, the CAR and others are working everyday to keep laws fair and protect people. Our guest today, Gideon Blustein, is the director of member outreach for the Illinois REALTORS …
 
Ryan Smith is not an optimist, but a realist. With a stark numbers-based opinion, Ryan provides his thoughts on Chicago’s housing market, the strength and the validity of the recent appreciation, and how long it may take to get through upcoming foreclosure inventory. We’ve had Ryan on here before (Episode 28), but last time it was too good of a con…
 
Lee Kiser is the co-founder of Kiser Group, a member of the Forbes Real Estate Council, and a wealth of knowledge in the Chicago market (and a local musician!). In today’s episode, Lee provides his thoughts on how today’s hot market differs from 2005, how institutional and private money has altered apartment investing in Chicago, and what neighborh…
 
Possibly the biggest consideration when taking on a rehab project is how to finance the deal. We’ve all considered hard money, FHA has their 203K loan program, and we’ve probably seen a late night commercial or two. Perry Farella of Prime Lending talks us through a loan program which is a cross between a conventional loan and hard money, something …
 
Besides rate and term, what other items I should ask about when talking to different lenders? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman of Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.…
 
One of the most important team members that real estate investors rely on is their attorney. Not all closings are created equal and Gina Diaz explains some of the closing nuances both through the eyes of an attorney and as an investor. Gina provides great insights into how to successfully close on a short sale, what to be aware of in a double close…
 
With nearly 30 years of experience as a broker, Frank Montro, the King of Chicagoland, shares his reflections on how the industry has changed from the early ‘80s to today. While touching on strategies his team uses to generate business, and cementing what it takes to succeed, Frank gives a compelling presentation that is certain to teach you someth…
 
Be honest with yourself...how many excuses do you tell yourself? Farrah Ali was a single mom in debt, working full time, but did not let that deter her from financial freedom. Listen to her incredible story and how it has impacted all areas of her life. She details even more of this in her book, “Diaries of A Female Real Estate Investor.” If you li…
 
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…
 
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