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
 
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 a…
 
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 Chi…
 
World Relief Organization (WRO) Chicagoland is a humanitarian organization whose focus is to aid refugees and immigrant families in finding housing and rebuilding their lives in Chicago. As a Chicagoland housing provider, there is not only good that you can do by partnering with WRO, but you can also benefit from a stream of applicants with specifi…
 
So what happened in the Chicago real estate market in 2021 and where are we headed in 2022? Our guests today, Casey Smagala and Steven Vance both of Chicago Cityscape, are here to share data you won’t want to miss. Casey and Steven explain how their data aggregation software allows them to efficiently analyze neighborhoods and identify paths of pro…
 
What is a wholesaler and as an investor why should I care? 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 2021.…
 
Regardless of which real estate assets you fancy, you are about to experience massive disruption in the upcoming years. That’s according to the mad scientist of multifamily and returning guest Neal Bawa (previously on episode 26). Neal drops a fascinating outlook on the retail sector, particularly shopping malls and their post-COVID recovery. He al…
 
You know how you see larger developments on major intersections and wonder “who’s doing that?” Well the answer is people like today’s guest Matt Katsaros. Matt started his real estate career as a top-performing commercial broker at Kise before transitioning to a director of acquisitions at Pangea. Those extraordinary experiences primed him for inve…
 
What closing costs and credits can I expect on my HUD statement? 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 2021.…
 
You may have already listened to our househacking from hell episode (Episode 89). Today, we don't have tenants stealing cars or anyone overdosing, but we do have typical obstacles faced with a first-time househack; all compounded with the fact that this project included a gut rehab. Our guest today, Alex Martinez, dove in head first, encountered nu…
 
From toilets falling through ceilings, to gentrification, Gordy Payne has seen it all as a hands-on owner in Pilsen. Gordy took a chance on Pilsen due to its proximity to downtown and made a name for himself for his ability to restore beautiful vintage buildings. He fully committed to the community, and for this, the community has treated him well.…
 
What are tactical steps to follow when sending, responding, and tracking mailers? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Sharad Mehta of REsimpli ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2021.…
 
Today, Tom and Mark have an excellent conversation with Judy Frydland, who served as the commissioner of buildings for the City of Chicago from 2015-2020. A lot happened under her leadership including the streamlining of the permit process to make it simpler and more efficient than ever to get work done. Listen in on her story for some excellent ad…
 
MOLD! It’s the scary four-letter word that investors never want to hear and it does not belong in a healthy property. However, a basic understanding of mold and its misconceptions in the marketplace will make you a better investor. After having a bad experience with a mold company, investor Greg Bukowsi saw a need in the market and made it his miss…
 
Will County is one of the fastest growing counties in Illinois, and when compared to Cook County, it offers a faster growth rate and a lot more room for development and expansion. As a second generation property manager and investor, Jason Marcodes from Landmark Property Manager, not only grew up in Will County, but grew up in the business. Today h…
 
In our first live recording, we celebrate 100 episodes by asking questions to the audience (see how many answers you know) and also answering multiple questions from attendees. We discuss our favorite parts of the podcast, lessons learned from interviewing multiple Chicago rockstars, whom we still want to interview, and the future of the Straight U…
 
As this episode airs, several of the Chicago townships have already been reassessed, leaving many owners with an unpleasant increase in property taxes. Returning guest Tim Jacobs of KSN Law (appeal.tax), joins us to discuss what he’s seen in the Chicago townships that have been reassessed, and what he feels will happen in several townships about to…
 
Samuel Pavlovcik is a distinguished self-certified architect who specializes in working with investors in Chicago and the surrounding villages and suburbs. Today Samuel walks us through the different permits in Chicago, the nuances of Chicago’s permitting process, and also what to expect when applying for a zoning variance. Samuel presents a candid…
 
After being routinely recognized as a successful multifamily broker, Kyle Shoemaker set out to create a rare brokerage that focuses solely on affordable housing. Kyle is a true expert and walks us through the nuances of affordable housing and unique challenges and opportunities presented in this space. Affordable housing can be complicated, which i…
 
The Community Investment Corp, or the CIC, has been a stalwart in Chicago since the 1970s and has reinvented the way owners can create affordable housing units for their communities. Stacie Young was just recently appointed the new President and CEO and she has lots of plans in the works. Today she comes to us to discuss the various ways investors …
 
What’s your unit goal? Is it 20...maybe 50? Well today’s guest explains how his company amassed 1200 units solely in Hyde Park, (not including their north side portfolio). Nick Hollenkamp drops street-level advice on the different corridors of Hyde Park along with his ten year forecast for the neighborhood. Nick provides great soundbits on why you …
 
You cannot grow without adequate funding. When it comes to private funds, there are so many questions asked as a new investor. Brian Lignelli takes the time today to talk about how his company, Continuum Capital Funding can put it’s partners in a position to scale and grow as well as how to prepare to work with them. He also hits on some of the var…
 
In episode 85, David Geen said househacking is the Stephen Curry cheat code of real estate. Many folks agree and have leveraged this strategy to kick off successful REI careers. However, there are real risks that arise the moment you become a housing provider. Today’s guest, Joey Poshinskas, is an extremely resilient househacker who persevered thro…
 
Like many families in Chicago, Sal’s family came from the old world and settled in a turbulent part of the city at a turbulent time. As he’s now standing on the shoulders of what his parents initially organized, he’s building it farther than ever expected. Sal’s story is amazing, his advice is timely, and his passion is contagious. Listen to today’…
 
What steps can I take to maximize my appraisal? 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.By Mark Ainley and Tom Shallcross
 
Fernando Angelucci has spent the last decade becoming one of the largest wholesalers in the Chicagoland area. Fernando successfully scaled his wholesaling business to a goliath and used the same skill sets and systems to establish and grow his self storage portfolio. In today’s episode, Fernando breaks down why he prefers self storage over multifam…
 
Nationally-recognized real estate rockstar David Greene of Bigger Pockets and Keller Williams holds nothing back! David provides his thoughts on the BRRRR strategy and dissuades the myths around equity as a cushion. David also covers the buyer/investor relationship, houssehacking as a cheat code, and why you need to start pushing over dominos to bu…
 
How can I put my best foot forward when making offers and how can I show experienced agents that I am serious? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: John Warren of Second City Real Estate ----------------- Production House: Flint Stone Media Copyright of Straight Up Chica…
 
Malcolm Gladwell popularized the idea that it takes 10,000 hours to master something. Well, if that’s the case, Mike Olszewski has likely mastered his craft several times over. To date, he has sold over 17,500 REO properties, developed properties and has even begun his own private lending business. Today, you get to learn the process of acquiring, …
 
Knowing a couple neighborhoods intimately is better than a hundred superficially. That’s exactly what the Property People did in Chicago’s northwest neighborhood. It’s how they know how deep they can dig a basement out and how much value they’ll add. What certain features are expected and what can they pass on? Greg and Jenny are a rockstar duo tha…
 
From the downtown riverwalk, to larger lots and Suburban living, Naperville is a diverse market drenched with opportunity. Today’s guest, Josh Mitchell, has carved out his niche as the go to guy in the area, acting as both an investor and a broker for Re/Max in Naperville. In this episode, Josh answers some FAQs for people thinking about going down…
 
All the nuggets you’ve learned from previous episodes won’t add up to squat if you do not have the appropriate team in place. So how do you build that successful team? Today’s guest, Gary Davidson, is not only a rock star attorney, but he is the definition of a go-giver. In today’s episode you will learn how asking the question “how can I add value…
 
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.…
 
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