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...
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Straight Up Chicago Investor
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Podcast website
Latest episode
Jul 9, 2026
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Episodes
Episode 193: The 2023 Guide to The Chicago Eviction Process with Jessica Ryan 19.01.2023 1:05:08
Jessica Ryan, Head of KSN's Landlord/Tenant Department, joins us to educate Chicago Landlords on the eviction process and best practices! Jessica begins by explaining the first step in the process; properly serving a 5-day notice. She talks about utilizing process servers for notices and summarizes the filing fees associated with an eviction. Jessica then gives a detailed breakdown of the phases o...
Episode 192: Scaling Up In Albany Park, Lincoln Square, and Ravenswood with Nick Yassan 12.01.2023 52:21
Nick Yassan, President of Rany Management, grew up in a family of real estate investors and has been instrumental to growing his company's real estate portfolio! Nick begins by explaining how he was involved in real estate from an early age and the competitive advantage that it has given him. He shares what the 2008 housing crash was like and how that impacted his real estate investing. Nick jumps...
Episode 191: Understanding Your Insurance Premium and Potential Money Saving Credits 10.01.2023 14:50
What goes into an insurance premium and what are some items investors should look out for? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Josh Steigelmann , State Farm Insurance Link: Investor Stories Featuring Sean Morrisey ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2023.
Episode 190: Everything Chicago Investors Need to Know About Logan Square with Luke Blahnik 05.01.2023 58:04
Real Estate Broker, Developer, and Entrepreneur Luke Blahnik joins us to discuss his neighborhood of expertise: Logan Square! Luke knows the neighborhood block by block and outlines some of the premier streets that feature phenomenal housing stock on oversized lots. Luke elaborates on the different pockets of the neighborhood including the higher priced areas around the Boulevards and other more a...
Episode 189: How To Underwrite Chicago Multifamily Buildings with Essex Director Rick Ofman 29.12.2022 58:50
Rick Ofman has over six years of experience in commercial real estate and is a Director at Essex Realty Group. Rick kicks things off by defining underwriting and associated terminology. He provides a thorough breakdown of income, expenses, and necessary assumptions. Rick shares insight on forecasting variables such as rehab costs, rent increases, and tax increases to name a few. He explains some v...
Episode 188: Forewarn - A Powerful Tool to Validate Personal Information and Criminal History (and it's free for most Chicago agents!) 27.12.2022 13:14
What is Forewarn? How does it benefit agents and housing providers and how can I utilize the tool? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Megyn Christensen, Forewarn ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 187: Department of Housing Commissioner Marisa Novara; Moving Chicago Forward 22.12.2022 1:03:34
Marisa Novara was appointed as Commissioner of the Department of Housing (DOH) in 2019 and has since led the creation of policies to promote equitably distributed affordable housing across the City. Commissioner Novara starts by explaining the purpose of the DOH. She dives deep on a fascinating study on segregation across the City that her team conducted. She speaks to the results of the segregati...
Episode 186: CEO Scott Trench Pulls Back The Curtain at BiggerPockets 15.12.2022 1:09:15
At the age of 32 years old, Scott Trench has already become CEO of BiggerPockets, and his contributions have helped countless investors build wealth. Scott discusses meeting Josh Dorkin and the early start-up days at BiggerPockets (BP). He speaks to BP's rapid growth, challenges along the way, and of course, BP's loyal customer base. Scott fills us in on BP's current vision and some potential upco...
Episode 185: What Chicago Investors Need to Know About the Updated FHA Limits 13.12.2022 12:14
What are the new FHA limits and what do investors need to know when exploring these FHA options? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Chris Puleo, Puleo Group Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo ----------------- Production House: Flint Stone Media Copyright of S...
Episode 184: Overseeing $8 Billion in Real Estate Transactions with Chicago Local Collete English Dixon 08.12.2022 56:09
Collete English Dixon has overseen over $8 Billion in real estate transactions and joins us to discuss how the industry has changed. Collete explains how large real estate transactions are different today compared to 25 years ago and discusses the impact that large institutional investors have had on the market. She breaks down the difference between large scale deals and smaller transactions. Col...
Episode 183: Forty-Six Years of Chicago Real Estate Knowledge with Pioneer Vince DePaul 01.12.2022 54:36
Vince begins by talking about his previous career as a rockstar manager (Styx)! He shares stories about Roseland and Humboldt Park in the 60s and 70s. Vince transitions into his journey as both a real estate broker and investor. He dives deep into the pros/cons of getting a broker's license as an investor and the requirements to get licensed. Throughout the episode, Vince speaks to the power of re...
Episode 182: How to Vet Contractors For Your Chicago Rehab 29.11.2022 15:29
What are the steps I should take to vet my Chicago contractors? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Bolanle Ogunmakin, Quality Builders Link: Straight Up Chicago Investor Episode 76 ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 181: Million Dollar Batavia 5-Flat From Networking to Closing (POV) 24.11.2022 1:00:43
Return guests Bibek Das, Eric Workman, and Matt LaCosse join us to discuss a 5-unit deal with a lot of hair on it! Matt (buyer on this deal) starts by talking about how our very own Mark Ainley (buyer's agent) brought this 5-unit property in Batavia to his attention. Eric (the lender on this deal) dives into the lending aspect of this deal and the group discusses the offer formulation and negotiat...
Episode 180: From Prison to Real Estate Profits; A Transformational Chicago Journey Against All Odds with Mike Baker 17.11.2022 44:17
From a rough upbringing to a successful REI career in Chicago, Mike Baker joins us to discuss his journey and his vast knowledge on wholesaling, flipping, and consulting. Mike begins by outlining his troubled past involving drugs, gangs, and prison. He shares some of the lessons learned in prison and the mindset shift required to get started and to succeed in real estate. Mike, Mark, and Tom shar...
Episode 179: How to Reduce the Cost of your Chicago Lawn 15.11.2022 12:07
What are my options to remove maintenance costs on smaller pieces of lawns? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: James Galvin, Chicago Lawn To Garden ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 178: Rising Rates, 2/1 Buydowns, and The Foreseeable Future of Investing and Lending with Rock Star Lender (and Drummer!) Sam Sharp 10.11.2022 1:04:15
Sam Sharp has over 20 years experience in the Mortgage Industry and joins us to discuss rising interest rates. Sam begins by talking about his vast experience in the mortgage industry and the lending environment during the last housing crash. He shares tips that have helped him be a top-producing loan originator and provides advice for professionals trying to build their brand. Sam gives his take...
Episode 177: How to Analyze and Buy Mixed-Use, Retail, and other Commercial Real Estate Assets in Chicago with Danny Spitz 03.11.2022 56:54
Danny Spitz of Greenstone Partners joins us to discuss the ins and outs of investing in commercial real estate. Danny kicks things off by sharing his start in real estate with a 3-flat in Bridgeport. He explains the differences between residential and commercial properties including insight on taxes and financing those assets. Danny speaks to the types of tenants and leases on mixed-use, retail, a...
Episode 176: How A Group of Relatively Unknown Investors Took Down a 64-Unit Building Without Being the Highest Offer 01.11.2022 17:39
A real live example of how beginning investors can separate themselves against known buyers without overpaying. Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Derek Kaptanoglu, Essex ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 175: SHOW ME THE INVESTMENTS!!! C&D Class Investing in Chicago's South and West Side Neighborhoods with Corey Oliver 27.10.2022 55:30
Corey Oliver has over 20 years of experience acquiring and repositioning multifamily buildings in Chicago's South and West Side areas. Corey talks about his start in real estate and how he acquired his first buy and hold buildings in North Lawndale. He speaks to the struggles of investing in C/D class areas including dealing with squatters, non-paying tenants, and gang activity. Corey dives deep o...
Episode 174: What Every Real Estate Investor Needs to Know About Appliances with Local Chicago Vendor Kevin Krasney 20.10.2022 47:25
Kevin Krasney is the third-generation owner of Cole's Appliances, which is still situated on the same Lincoln Ave corner in North Center. Kevin talks about his family-owned and operated business and how Cole's provides tremendous value to investors. He walks through the appliance ordering and installation process and how the recent supply chain issues played into this process. Kevin gets granular...
Episode 173: What Investors Need to Know to Obtain Commercial Financing in the Upcoming 6-12 Months 18.10.2022 13:04
What are lenders taking a harder look at in this market? Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guest: Eric Workman, Renovo Financial ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2022.
Episode 172: The Ins & Outs of Chicago's North Lawndale Neighborhood with Robert Waz 13.10.2022 51:06
Robert Waz of Exterplexy Real Estate & Management joins us to discuss the ins and outs of investing in the North Lawndale neighborhood. Robert kicks things off by explaining why he started investing in North Lawndale. He dives into unforeseen challenges and underwriting considerations to ensure investors accurately account for all expenses and. Robert goes deep into the neighborhood, including its...
Episode 171: From the East Side to the West Side, Sonia Del Real Explains the Genesis of the Latino Real Estate Investors' Council 06.10.2022 49:26
Sonia Del Real of Third City Consulting and LREIC join us to discuss her involvement with Chicago Housing Provider Advocacy groups and how investors from all ethnicities can benefit from this group. Sonia shares her background as a second-generation immigrant and a Chicago native along with her investing journey prior to the housing crash. She speaks to her transition into education and advocacy...
Episode 169: How To Leverage Chicago's Transit-Oriented Development Incentives with Chicago Cityscape 29.09.2022 57:11
Return guests Casey Smagala and Steven Vance of Chicago Cityscape join us to discuss the revised Transit-Oriented Development (TOD) ordinance and other development trends in Chicago! Casey and Steven start off by explaining the TOD ordinance and the changes resulting from the recent revision. They dive deep on the impacted neighborhoods, zoning districts, and provisions of the ordinance. Casey and...
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