Shows / 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…
Episodes
Straight Up Chicago InvestorEpisode 430: From Flipping Neighborhood Warehouses to Multifamily Rentals: Rapid REI Growth with Reed Meyer
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…
Straight Up Chicago InvestorEpisode 429: Opportunity Zones & Tax Credits For Chicago Investors with Darryl Jacobs
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…
Straight Up Chicago InvestorEpisode 428: Updates To The 2026 Lease and Other Recent Legal Changes With Mark Ainley
What are recent legal updates to the 2026 lease and new squatter laws? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark…
Straight Up Chicago InvestorEpisode 427: 2026 Chicago Real Estate Forecast: Trends, Risks, and Opportunities with Jake Fugman and Mike Scanlon
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…
Straight Up Chicago InvestorEpisode 426: Reshaping Suburban Woodstock with Jessica Erickson
Jessica Erickson, Director of Economic Development for the City of Woodstock, joins us to discuss development news and opportunities in Woodstock, IL! Jessica…
Straight Up Chicago InvestorEpisode 425: Benjamin Stef - Unlock Equity in Your Investment Property with Little Known HELOC Options
Do you need a HELOC on your investment property? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Benjamin Stef, NEXA Mortgage…
Straight Up Chicago InvestorEpisode 424: Chicago Foreclosure Market with Top REO Agent Ryan Smith
Ryan Smith, top producing agent specializing in REO properties, returns to provide an update on the state of the Chicagoland foreclosure market heading into…
Straight Up Chicago InvestorEpisode 423: Fire, Squatters, and Drugs! When Your $100k Chicago Investment Goes To Zero with Jonathan Klemm
Jonathan Klemm of Quality Builders returns to discuss refinements in his General Contracting business and investment strategy since his last appearance!…
Straight Up Chicago InvestorEpisode 422: Mark Ainley Shares Why He's Excited for Chicago's 2026 Market
Is now a good time for me to purchase in Chicago? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley, Straight Up…
Straight Up Chicago InvestorEpisode 421: Alec Greenberg Scales to Chicago Multifamily from Day 1
Alec Greenberg is the Principal of Base 3 Development and has vast experience developing and stabilizing multifamily assets! Alec explains how he transitioned…
Straight Up Chicago InvestorEpisode 420: The Chicago Permitting Process with Tom Shallcross
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…
Straight Up Chicago InvestorEpisode 419: What You Need to Know to Determine Section 8 Rental Amounts With Mark Ainley
How do I navigate the rent determination process for Section 8 applicants in Chicagoland? ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 418: Zeke McDonald-Lewis Reviews Cook County Eviction Process for Chicago Landlords
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…
Straight Up Chicago InvestorEpisode 417: 4 Chicago Companies, 800 Doors, & 20 Years! Here's What Actually Worked with Niko Apostal
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…
Straight Up Chicago InvestorEpisode 416: Mark Ainley Explains Three Red Flags When Screening Tenants
How do I protect myself against potential tenant screening scams? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Guest: Mark Ainley…
Straight Up Chicago InvestorEpisode 415: Lawrence Dunning Breaks Down Chicago Neighborhoods and New Construction 3 Flats
Lawrence starts by explaining how he found his business niche and lessons learned from working with successful developers. He gets granular on his geographical…
Straight Up Chicago InvestorEpisode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows
SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs! Mark jumps right in by…
Straight Up Chicago InvestorEpisode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev
When do I have to have my cost segregation done to ensure it is good for my 2025 taxes? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com…
Straight Up Chicago InvestorEpisode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio…
Straight Up Chicago InvestorEpisode 411: Shawn Good Creates Opportunity with Off Market Deals
Shawn Good is a seasoned attorney and real estate investor with vast experience acquiring and stabilizing off-market real estate. Shawn kicks things off by…
Straight Up Chicago InvestorEpisode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross
What the different ways I can adjust my offer to make it more attractive? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the…
Straight Up Chicago InvestorEpisode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman
Eli Goodman of Illinois Real Estate Buyers gives the complete playbook on dealing directly with sellers to acquire off-market deals! Eli starts with explaining…
Straight Up Chicago InvestorEpisode 408: Chicago Suburb Land Development with Jim Paul
Jim Paul, Director of the ALPS Group, has over 2 decades of experience in land development and receivership. Jim jumps right in by discussing an early 21-acre…
Straight Up Chicago InvestorEpisode 407: How to Take Advantage of the Different Zoning Labels in Chicago
What are the differences between R2, R3, R4, and R5 zoning? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show…
Straight Up Chicago InvestorEpisode 406: How to Quit Your W2 After 1 House Hack with Moises Correa
Moises Correa, Principal of Proximo Equity Group, leads a team that specializes in value-add multifamily real estate across the Midwest. Moises provides the…
Straight Up Chicago InvestorEpisode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal
Joe Smazal, Senior Managing Partner of Interra Realty, has over a decade of experience selling mid-market apartment buildings and recently surpassed $1 Billion…
Straight Up Chicago InvestorEpisode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo
What are my lending options for a non-owner occupied investor? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show…
Straight Up Chicago InvestorEpisode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski
Lantz Kurzawinski, Marketing Specialist for the Straight Up Chicago Investor Podcast, tells his story of grinding to succeed in real estate at an early age…
Straight Up Chicago InvestorEpisode 402: Looking At Chicago Investing Differently with Jason Wagner
Jason shares why he chose to invest in Chicago's northwest side and how he's achieved success in that area. He breaks down assumable loans and 2-1 buydowns…
Straight Up Chicago InvestorEpisode 401: Interest Rates Are Coming Down According to Chris Puleo
Chris Puleo lays out tangible reasons why he feels interest rates will be coming down in the upcoming future. ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 400: The Proven Way To Break Down Chicago Real Estate Investing with Kevin Rocio
Kevin Rocio, founder of ROC Advisory Group, is an award winning commercial real estate broker, mentor, and investor. Kevin shares how he built a business and…
Straight Up Chicago InvestorEpisode 399: Finding Properties Today: The Guide to Cash Flowing Deals with Micah White
Micah White is a real estate coach with a proven track record of finding cash flowing real estate with great ROI! Micah starts by explaining the ins and outs…
Straight Up Chicago InvestorEpisode 398: House Hacking Your Way to Lasting Wealth with Paul de Luca
Paul de Luca of The Axon Group joins us to provide great insights on leveraging house hacking to grow a portfolio and how to succeed as an investor-friendly…
Straight Up Chicago InvestorEpisode 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?
What are the "do's" and "don'ts" when filing an insurance claim? ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show…
Straight Up Chicago InvestorEpisode 396: Buying, Building, and Adding Value in Self Storage with Fernando Angelucci
Fernando Angelucci returns to the podcast to explain how he has rapidly grown his self storage business and the drivers behind increasing self storage demand!…
Straight Up Chicago InvestorEpisode 395: Chicago Property Management and Leasing Best Practices with Max Motew
Max Motew, Director of Leasing at Mo2 Properties, joins us to share great insights on acquiring, renovating, and stabilizing small multifamily properties in…
Straight Up Chicago InvestorEpisode 394: The Legal Nuances of Different Real Estate Partnership Structures
What do investors need to consider from a legal perspective when setting up new partnerships? ============= Connect with Mark and Tom…
Straight Up Chicago InvestorEpisode 393: Chicago Veterans' Guide to Real Estate Success with DuBois Toy
DuBois Toy is a seasoned real estate investor, veteran, and cybersecurity analyst who has a passion for helping veterans maximize their real estate benefits!…
Straight Up Chicago InvestorEpisode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars
Kevin Cawley, aka Cost Seg Kev, is a Senior Account Executive at CSSI Services - a firm with over 55,000 cost segregation studies completed since 2003. Cost…
Straight Up Chicago InvestorEpisode 391: Do You Have a Business Continuation Plan?
Josh Steigelmann explains the importance of a business continuation plan and provides step-by-step guidance on how investors can set-up a business continuation…
Straight Up Chicago InvestorEpisode 390: What Not To Do When Disaster Strikes: Mitch Schoeneman on Insurance Claims
Mitch Schoeneman is a Managing Partner at A. Schoeneman & Co. - a top rated Chicago public insurance adjusting firm that has been serving customers for over 55…
Straight Up Chicago InvestorEpisode 389: Different Approach To Short Term Investing In Chicago With Sebastian Mysliwiec
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…
Straight Up Chicago InvestorEpisode 388: NBOA 2025 Summer Soiree Update
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…
Straight Up Chicago InvestorEpisode 387: This Is How You Make Money In Chicago In Your Early 20s with Alex Diaz
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…
Straight Up Chicago InvestorEpisode 386: How to Invest in DuPage County with Katie and Rob Hayes
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…
Straight Up Chicago InvestorEpisode 385: What is a Demand Letter and How to Handle Receipt of a Demand Letter
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…
Straight Up Chicago InvestorEpisode 384: From Cold Calling to Billions of Dollars in Loans Originated with Jake Clopton
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…
Straight Up Chicago InvestorEpisode 383: From Chemist to Chicago's "Bow Tie" Attorney w/Mahmoud Faisal Elkhatib
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…
Straight Up Chicago InvestorEpisode 382: What Investors Need to Know About Built to Rent Opportunities in Chicago
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…
Straight Up Chicago InvestorEpisode 381: How Chicago's Powerhouse Lender Renovo Financial Was Built with Kevin Werner
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…
Straight Up Chicago InvestorEpisode 380: Innovation in Modular Housing With Rory Rubin
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…
Straight Up Chicago InvestorEpisode 379: Preparing Your Property To Add an ADU
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…
Straight Up Chicago InvestorEpisode 378: How Wonderful Togbey Built a 20-Unit Portfolio Against the Odds
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…
Straight Up Chicago InvestorEpisode 377: This is How Grit Can Take You Further in Chicago Real Estate with Daniel Baker
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…
Straight Up Chicago InvestorEpisode 376: Buy Before You Sell; How To Write Offers Non-Contingent on The Sale of Your Existing Property
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…
Straight Up Chicago InvestorEpisode 375: Learn How To Build A Chicago Portfolio Without Quitting the W2 with Nate Fernandez
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…
Straight Up Chicago InvestorEpisode 374: Taking On Opportunity In Chicago's Toughest Neighborhoods with Corey Oliver
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…
Straight Up Chicago InvestorEpisode 373: A New Option to Fund Renovations For Chicago 2-4 Properties
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…
Straight Up Chicago InvestorEpisode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell
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…
Straight Up Chicago InvestorEpisode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan
Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age! Michael starts by explaining how he realized…