Straight Up Chicago Investor

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 are the issues more widespread? Listen in today to...

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 your tax liability. If you're not trying to save h...

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 neighborhoods; tenant and rental profiles in varying neig...

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 groups and associations who are allies. Some hot bu...

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 area; his strategy and why he's interested in HOAs....

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, key focus areas and how to analyze an area. She a...

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 imperative you understand how it works...ESPECIALLY in a ci...

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 measures to maximize your net worth.   Aaron also...

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 long-term with his rehabs, appreciates previously gu...

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 attributes he looks for in an investment property, how h...

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 representing banks and buyers in more than $300 million...

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 Row and an acquisition of a historic Chicago build...

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 Mark, have great FAQs for Lauren and she delves i...

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 development of several Metra lines, the 50s-80s were...

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 lending during tough times, to helping analyze risk,...

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 tests. Not to mention some of the things investor...

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 the same page as your partner and so on. Since that...

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 tenant issues. Bob also discusses the new ADU ordinan...

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 episodes, including some of their favorite episodes...

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 landlord process and protocol and learn about a ne...

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. Sean also provides his thoughts on the imminent...

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, their commitment to neighborhoods, CCLB's unique a...

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 the RTLO, and the unintended consequences from prev...