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...
Author
Straight Up Chicago Investor
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Podcast website
Latest episode
Jul 9, 2026
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Episodes
Episode 168: Breaking Down Bridgeport Block by Block with Ada Li 22.09.2022 49:34
Ada Li is a Chicago-based Developer with over 20 years of experience. Ada shares her experience with her family's construction business, which includes dealing with Chicago Inspectors, zoning changes, and other lessons learned over the years. Ada dives deep into Bridgeport by sharing insight on the different pockets of the neighborhood, how values vary across those areas, and her long-term outlook...
Episode 167: When Should I Lock My Interest Rate, and What Are The Different Rate Lock Options? 20.09.2022 11:48
When should I lock in my mortgage rate in a volatile market, and what is a float-down option? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella, Prime Lending | SUCI Episode 67 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 166: BiggerPockets J Scott Breaks Down the Economy, Our Debt Crisis, and the Real Estate Market Cycle 15.09.2022 57:32
Entrepreneur, investor, and best-selling author J Scott of BiggerPockets and Bar Down Investments joins SUCI and drops tremendous wisdom! J shares the mindset and adaptability required to become a successful real estate investor. He draws on his past experience to break down the economic climate by speaking to various topics including inflation, stagflation, the debt crisis, consumer behavior, and...
Episode 165: From Chicago Househacker, to Out of State Investor, to Leaving Her W2 Job with Kory Dieter 08.09.2022 49:40
Kory Dieter is a Chicago-based is a house hacker and professional out of state investor with a portfolio mix that includes SFRs and small multi-families across 5 markets. In today's episode Kory shares with us how she started her real estate journey with a house hack in Andersonville to how she was able to leave behind her W2 job. Along the way she's dabbled in a variety of investing strategies, i...
Episode 164: Replacement Cost vs Actual Cash Value 06.09.2022 9:33
What is the difference between actual cash value and replacement cost? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann, State Farm Insurance ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 163: From Listing Agent to Acquiring and Managing Hundreds of Units on Chicago's Northside with John McGeown 01.09.2022 45:12
Are you looking to learn about acquiring and managing multifamily properties in Chicago's Northside? If so, you'll get great value out of this show! John starts by talking about his military background and how that has served him in his real estate career. He provides details on managing his first large scale, multifamily property and how that success propelled his growth. John gets granular on re...
Episode 162: Property Management in Chicago's Southside with Tim Harstead 25.08.2022 46:29
Looking for insight on the nuances of acquiring and managing properties on the south side of Chicago? If so, this episode is for you! Tim starts by talking about his start in real estate and how he identified a need for quality property management on the south side. He provides insight on tenant screening, underwriting expenses, and subsidized housing for the C/D class assets he operates. Tim gets...
Episode 161: How financing for Chicago Non Conforming units just got easier. 23.08.2022 11:10
What are the recent changes within Freddie Mac that now allows for financing the rehab of an ADU project? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Link: https://perryfarella.com/blog/ ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 160: Comparing Chicago To Several Midwest Markets with Brian Kochendorfer 18.08.2022 50:37
Brian Kochendorfer returns to the show after 2 years! This time around Brian provides an objective analysis on how his investment properties in Indiana and Ohio compared to his Chicago portfolio. Brian kicks things off by sharing his investment parameters and how he ended up pursuing opportunities in Ohio and Indiana in addition to Chicago. He dives deep into the nuances of acquiring, repositioni...
Episode 159: From Successful BRRRR to Major Project Hurdles in Chicago's Western Suburbs with Zach Gring 11.08.2022 46:29
From successful BRRRR to a delayed, over-budget project, Zach Gring shares lessons learned from his investing journey! Zack starts by explaining how he established an asset class to focus on and the reasons for his criteria. He talks through a successful BRRRR project in Batavia and speaks to managing the rehab of a tenant-occupied property. He also shares some lessons learned from his delayed pro...
Episode 157: Investing in Chicago Midterm Rentals with Rishi Bajaj 04.08.2022 58:11
After staying in an Airbnb while on vacation, Rishi Bajaj realized how we can leverage this strategy and used midterm rentals to multiply his rental income! Rishi shares how he got the idea to venture out into the niche space of midterm rentals. He talks about furnishing, costs, and additional considerations when comparing midterm rentals to traditional long-term rentals. He dives into why he sees...
Episode 156: A Decade of Grinding and Succeeding on Chicago's Northside with Joe Smazal 28.07.2022 48:58
It first took Joe Smazal of Interra Realty six years to sell $100M of multifamily real estate. Six months into 2022, Joe has already sold $100M of assets THIS YEAR ALONE! Joe explains how he left his stable day job to become a Chicago commercial broker, and the growing pains and hustle required to get started. He then speaks to the importance of developing relationships for increased deal flow an...
Episode 155: Straight Up Tues Tip 33 26.07.2022 13:43
What are some of the useful technologies/apps that can help you scale your REI business? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bolanle Ogunmakin, Quality Builders Link: Episode 76: Big Business Processes Make a Powerful Small Business with Jonathan Klemm ----------------- Production House: Flint Stone Media Copyright of...
Episode 154: Scaling From a Duplex to a $100 Million Portfolio in Chicago's North and Northwest Side with Jeff Weinberg 21.07.2022 55:14
Jeff Weinberg of Drexel Properties joins us to discuss the importance of systems and relationships when scaling a large Chicago Real Estate portfolio. Jeff kicks things off by talking about his start in real estate and leaving his W2 job to pursue his passion full time. He jumps into the mindset and strategies that will help in scaling a portfolio. Jeff drops street level knowledge on the North an...
Episode 153: Building Wealth via Long-Term Real Estate Investments in Chicago with Bill Himmelstein 14.07.2022 54:25
Bill Himmelstein of Tenant Advisory Group drops in to share great insight on long-term investing and reminds us that real estate is not a "get rich quick" but rather a "get wealthy slowly" investment. Bill starts by talking about his start in real estate and his experience with multi-family investing. He gets granular by speaking to the effect of rising interest rates on the market and also explai...
Episode 152: Straight Up Tues Tip 32 12.07.2022 11:45
What is the NBOA Summer Soiree and how can investors benefit from this event? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Mike Glasser of NBOA Link: https://www.straightupchicagoinvestor.com/podcast/episode-37-the-nboa---your-ally-and-voice-as-a-chicagoland-housing-provider ----------------- Production House: Flint Stone Media...
Episode 151: Dissecting Property Taxes on your Chicagoland Properties with Cook County Assessor Fritz Kaegi 07.07.2022 52:49
Ever wonder how your Cook County properties are assessed and how taxes are calculated? Cook County Assessor Fritz Kaegi presents valuable info on property taxes and the overall mission of his office! Fritz starts by sharing his background and how it allowed him to seamlessly step in and improve processes as the Assessor. He talks about his office's responsibilities and some of the common misc...
Episode 150: Mastering Multi-Family to Propel Your Chicagoland Investments with Rod Khlief 30.06.2022 39:23
As many may already know, Rod Khleif is a multifamily real estate investor, business consultant, and high-performance coach. In today's show, Rod focuses heavily on being prepared to take action as opportunities arise during a changing market like the one we are in today! Rod starts off by speaking about the huge loss he experienced during the last housing crash and how he was able to bounce back...
Episode 149: Revitalizing the "Land of Lincoln" with Aurora Mayor (and potential IL Governor) Richard Irvin 23.06.2022 30:32
Mayor of Aurora and gubernatorial candidate Richard Irvin discusses his plan to create jobs, lower crime, and attract businesses if he were to be elected Governor of Illinois. Richards speaks on hot-topic issues including affordable housing, taxes, and crime. He dives deep into his tenure as Mayor of Aurora and how he can translate Aurora's successful revitalization to the rest of the state as go...
Episode 148: Acquiring Distressed Real Estate by "Beating the Streets" in Chicago with Joe Sevcik 16.06.2022 43:03
Are you struggling with deal flow in this market? Joe Sevcik drops in to share how Networth Realty is acquiring distressed properties and wholesaling to add value to their investors. Joe covers how his company is grinding it out by hitting the streets to get in front of motivated sellers. He talks about the mindset required to succeed in this space where rejection is commonplace. Joe dives deep in...
Episode 147: Straight Up Tues Tip 31 - Perry Farella Breaks Down HUD 203k Loan Options 14.06.2022 14:26
What is a HUD 203k loan, when does it make sense for investors to leverage this loan, and where do 203k loans fall apart? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Link: ttps://perryfarella.com/blog/ ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor...
Episode 146: How To Manage Your Rehabs and What to Look For In a Chicagoland General Contractor with RJ DeLeon 09.06.2022 53:14
RJ Deleon is all things real estate, as he wears the hats of a contractor, investor, and mentor. In today's show we focus almost exclusively on RJ's experience as a GC and how investors can best partner with contractors. RJ covers some of the most frequently asked questions investors have for GCs and how he handles different requests from investors. He showcases how his personal investing experie...
Episode 145: NFL Tight End Turned Chicago Real Estate Investor with Matt LaCosse 02.06.2022 41:10
Ever wonder how professional athletes are investing to set themselves up for life after their sports career? NFL Tight End Matt LaCosse joins us to shine light on this exact journey. Matt starts off by talking about how the skills required to be a professional NFL player translate to real estate investing. He explains why he came back home to Chicago to start his investing career. Matt dives into...
Episode 144: Straight Up Tues Tip 30 - Perry Farella Provides Numbers on a Recent Purchase and Rehab Projects He Financed 31.05.2022 13:02
Perry Farella provides tangible numbers on a recent purchase and rehab project he financed. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Perry Farella of Prime Lending Link: ttps://perryfarella.com/blog/ Link: https://www.straightupchicagoinvestor.com/podcast/episode-67-chicagoland-rehab-financing-without-using-hard-money-or-20...
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