Straight Up Chicago Investor
BookmarkStraight Up Chicago Investor
Straight Up Chicago Investor is a business podcast hosted by Straight Up Chicago Investor. It has 446 episodes, with the latest published April 2026.
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 and not worked in Chicago, you are in the right place.
business ·en ·446 episodes
Episode 444: Leveraging Tax Strategy to Boost ROI with Ryan Bakke
Episode 443: Adaptive Reuse & Ground Up Development with Adam Friedberg
Episode 442: How To Identify and Execute on Assumable Loans with Michael Scanlon
Episode 441: Chicago's Josh Bandoch Using Neuroscience to Win Negotiations
Episode 440: Cracking Cash Flow on Chicago's West Side with Jay Patel and Tedi Nati
Episode 439: The Ins-And-Outs of 203k and Homestyle Renovation Loans with Jonathan Klemm
Episode 438: Legalizing Apartments & the New ADU Playbook for Chicago Investors with Samuel Pavlovcik
Episode 437: Energy Efficiency in Chicago Real Estate with Joe Konopacki
Episode 436: Important Elections for Every Chicago Investors & the NBOA PAC Fundraiser with Rahm Emanuel
Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas
Episode 434: Interesting Lease Renewal Statistics and Strategies with Mark Ainley
Episode 433: Chicago Building Code Violations with Zack Limbaugh
Episode 432: Strategic Chicago House Hacking with Zach Posey
Episode 431: What You Need To Know About Real Estate Professional Status with Mike Procaccio
Episode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer
Episode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
Episode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley
Episode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
Episode 426: Reshaping Suburban Woodstock with Jessica Erickson
Episode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options
Episode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith
Episode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm
Episode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market
Episode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1
Episode 420: The Chicago Permitting Process with Tom Shallcross
Episode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley
Episode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords
Episode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal
Episode 416: Mark Ainley Explains Three Red Flags When Screening Tenants
Episode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats
Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows
Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev
Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
Episode 411: Shawn Good Creates Opportunity with Off Market Deals
Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross
Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman
Episode 408: Chicago Suburb Land Development with Jim Paul
Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago
Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa
Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo
Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski
Episode 402: Looking At Chicago Investing Differently with Jason Wagner
Episode 401: Interest Rates Are Coming Down According to Chris Puleo
Episode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio
Episode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White
Episode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca
Episode 397: When Should You File an Insurance Claim and What Are the "Do's" and "Don'ts" When Filing an Insurance Claim on Your Property?
Episode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
Episode 395: Chicago Property Management and Leasing Best Practices with Max Motew
Loading reviews...
Loading similar podcasts...