Straight Up Chicago Investor

Straight Up Chicago Investor

Business EN ↓ 468 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 importantly, lessons learned. If you are looking for ground level information and want to learn what has worked...

Author

Straight Up Chicago Investor

Category

Business

Latest episode

Jul 9, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

Episode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations 26.03.2026

Josh Bandoch is the Head of Policy at the Illinois Policy Institute, TED Talk Speaker, and Author who joins to discuss his new book, How to Get What You Want! Josh jumps right in by explaining the concept of his book and the neuroscience of persuasion! He shares insights on how the brain works as it relates to persuasion and gives tactical negotiation tips. Josh describes the process of writing hi...

Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati 19.03.2026

Jay Patel and Tedi Nati of JP Acquisitions join us to explain how they've leveraged mentors and discipline to build a sizable multifamily portfolio on Chicago's West Side!  Jay and Tedi explain how they networked and built their team to set themselves up for success when starting in real estate! They break down raising money and setting up a syndication to acquire their first multifamily building...

Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm 17.03.2026

What do investors need to be aware of when taking on a 203k or Homestyle Renovation loan? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Jonathan Klemm , Quality Builders Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicag...

Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik 12.03.2026

Samuel Pavlovcik of the Pavlovcik Architecture returns to explain opportunities brought by the expanded city-wide Additional Dwelling Unit (ADU) Ordinance! Samuel jumps right in by explaining the process and expectations on obtaining a Zoning Change without leveraging the ADU ordinance! He dives deep on various Zoning and Building Code requirements when looking to build and/or legalize a basement...

Episode 437: Energy Efficiency in Chicago Real Estate with Joe Konopacki 05.03.2026

Joe Konopacki, Founder and CEO of Insight Property Services, is a seasoned home inspector with various professional certifications on Building Performance and Efficiency! Joe starts with a story on acquiring a mixed-use building to establish his business and invest simultaneously! He breaks down his background of growing up in a real estate family and transitioning into the business. Joe gets gran...

Episode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel 03.03.2026

What are the upcoming elections that every investor should be aware of, and what's this dinner with Rahm Emanuel I heard about? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mike Glasser & Aron Borstein, NBOA PAC | An Evening with Rahm Emanuel ⭐⭐Get your tickets today!⭐⭐ Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chi...

Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas 26.02.2026

Gil Villegas is the alderperson of Chicago's 36th ward and has focused on generating opportunities for economic and business development to best serve the constituents of his ward! Alderman Villegas starts by discussing how zoning changes can be utilized to create win-win situations for investors and members of a community or ward! He talks about how he and his fellow members of City Counsel were...

Episode 434: Interesting Lease Renewal Statistics and Strategies with Mark Ainley 24.02.2026

What are the common mistakes made when handling lease renewals? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor and GC Realty Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInv...

Episode 433: Chicago Building Code Violations with Zack Limbaugh 19.02.2026

Zack Limbaugh of the Limbaugh Law Firm returns to dive deep on code violations including top pitfalls to avoid! Zack starts by explaining the 101 on buying properties with building code violations! He discusses top lending considerations when attempting to finance a property with violations. Zack dives deep on common code violations, how owners get notified, and how to mitigate your risk! Througho...

Episode 432: Strategic Chicago House Hacking with Zach Posey 12.02.2026

Zach Posey joins us to explain how he's acquired various house hacks and grown a significant net worth all while having a demanding W2 career! Zach starts off by detailing the acquisition of his first house hack and the hurdles that came almost immediately after closing. He talks about purchasing an oversized 4-unit building, seeing value-add potential, and executing a renovation strategy to creat...

Episode 431: What You Need To Know About Real Estate Professional Status with Mike Procaccio 10.02.2026

What is real estate professional status and why is it important for investors? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Michael Procaccio,  Pro Financial Services Group Inc Email the Show: StraightUpChicagoInvestor@gmail.com Link: Build Your Team | Straight Up Chicago Investor Podcast Properties for Sale on the North Side?  We want to buy them. Email: Straight...

Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer 05.02.2026

Reed Meyer, founder and managing broker at Lease312, shares top tier leasing advice and how connecting with mentors has propelled his real estate journey's growth at such a young age! Reed starts off by detailing the process of acquiring his first property; a 3-unit house hack in Logan Square. He talks about purchasing an industrial warehouse and flipping it for double the price in just 45 days! R...

Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs 29.01.2026

Darryl Jacobs, partner at Ginsberg Jacobs, has over 3 decades of experience in tax and corporate law with a focus on tax credit financing transactions. Darryl starts off with a high-level overview of the various tax credits available to investors. He dives deep on opportunity zones and how geographical areas get designated as opportunity zones. Darryl explains how investors can leverage New Market...

Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley 27.01.2026

What are recent legal updates to the 2026 lease and new squatter laws? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast and GC Realty & Development LLC Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacan...

Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon 22.01.2026

Jake Fugman and Mike Scanlon of The Axon Group return to forecast Chicago's Real Estate Market in 2026! Jake and Mike kick things off by reflecting on their 2025 predictions including office space leasing trends, downtown sales stats, and impacts of the Northwest Side Preservation Ordinance. The duo then make their 2026 predictions with topics ranging from ADU Zone expansion to creative mortgage s...

Episode 426: Reshaping Suburban Woodstock with Jessica Erickson 15.01.2026

Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica starts with her backstory on moving from Denver to Chicagoland and ultimately taking a role in Economic Development for the City of Woodstock. She breaks down Woodstock's downtown redevelopment plan and also speaks to city corridors with dev...

Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options 13.01.2026

Do you need a HELOC on your investment property? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Benjamin Stef, NEXA Mortgage Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your tim...

Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith 08.01.2026

Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into 2026! Ryan starts with an overview on the foreclosure process and expectations when getting into a foreclosure transaction as a buyer. He provides tips on positioning yourself as a legit, experienced buyer in the eyes of REO listing agents. Ry...

Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm 01.01.2026

Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance! Jonathan starts by explaining partnership pitfalls to avoid based on recent changes within his business. He gets vulnerable by discussing a multifamily investment on Chicago's southside that involved various evictions and a $400,000 fire caused by...

Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market 30.12.2025

Is now a good time for me to purchase in Chicago? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 3...

Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1 25.12.2025

Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets! Alec explains how he transitioned from the corporate real estate world to a more entrepreneurial position at Base 3 Development. He describes how he "stretched" out of his comfort zone by jumping into a 6-unit gut rehab project off the bat and shares lessons learned! Alec sh...

Episode 420: The Chicago Permitting Process with Tom Shallcross 18.12.2025

SUCI Podcast Co-Host Tom Shallcross is today's special guest and breaks down everything you need to know about architectural plans and permits in Chicago! Tom discusses when you need plans and permits for a project and when it's appropriate to engage an architect. He shares the best way to optimize timelines to ensure your plans and permits get approved as fast as possible. Tom discusses lessons l...

Episode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley 16.12.2025

How do I navigate the rent determination process for Section 8 applicants in Chicagoland? ============= C onnect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up Chicago Investor Podcast Email the Show: StraightUpChicagoInvestor@gmail.com Properties for Sale on the North Side?  We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can pl...

Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords 11.12.2025

Zeke McDonald-Lewis is an attorney at Erwin Law who specializes in real estate evictions and civil litigation! Zeke starts by breaking down the first steps in handling a non-paying tenant including the appropriate steps for delivering a 5-day notice. He gets granular on the eviction process timeline and dos/don'ts to avoid delaying the process. Zeke shares top mistakes made in eviction cases and s...

Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal 04.12.2025

Niko Apostal, founder of Niko Collaborative and managing broker at Essex 312, joins us to share his expertise in real estate brokerage with a focus on 2-4 unit buildings! Niko starts by explaining how he got his real estate business off the ground in the early 2000s and survived the real estate crash! He provides practical tips for anyone looking to start a real estate business. Niko shares detail...

Listen to the Straight Up Chicago Investor podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.