CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

For our milestone 400th episode, we sat down with a Chicago heavy-hitter whose career spans lending, development, and commercial brokerage. Kevin Rocio doesn’t do small talk — he does numbers, systems, and results. From building union-focused mortgage programs in the ’90s to exiting lending before the 2008 crash, to training brokers on how to properly price two- to four-flats with GRM (not cap rate), Kevin lays out a b...

There’s no shortage of real estate hustle stories in Chicago, but few are as practical — and repeatable — as what Micah White is doing. He didn’t start with millions, institutional investors, or shiny new construction. He started like most Chicago landlords: with an old three-flat, below-market rents, and an inspection report thicker than a phone book.Through transparent conversations with residents, calculated ...

House hacking continues to be one of the most powerful ways for Chicago investors to build wealth and more importantly jump start their investment journey. Few strategies combine affordability, leverage, and cash flow potential like living in one unit while renting out the others. Paul De Luca, broker with the Axon Group, has personally house-hacked four different properties across Berwyn, Belmont Cragin, and Portage Park — and h...

Most landlords only think about insurance on renewal day—until a pipe bursts, a kitchen burns, or hail rips through a roof. That’s when the sequence of your next few moves can save you thousands or make a mess of your premiums and insurability.In this Straight Up Chicago Investor Tuesday Tip, State Farm agent Josh Steigelmann joins Tom and Mark to break down the claim decision tree, what to do before ...

There’s a lot of noise out there about how hard it is to find self storage deals, but Fernando Angelucci has been quietly proving otherwise. In just four years, he scaled from $50M to $230M in assets under management, grew to 54 facilities across 24 states, and brought in 900+ investors. In this episode of the Straight Up Chicago Investor Podcast, Fernando breaks down how he sources mom-and-pop self-storage deals, uses creative fi...

Scaling a property management business in Chicago isn’t just about buying more units, it’s about mastering communication, understanding tenant behavior, and balancing investor expectations. Few know this better than Max Motew, Director of Leasing at Motew Properties, a family-owned firm managing nearly 1,000 units across Chicago’s North Side.From navigating landmark rehabs and property taxes to setting renewal strategi...

Gut rehabs get all the glory, but they come with hidden surprises, endless delays, and major stress. What if we told you that new construction—yes, from the ground up—is often simpler, more scalable, and more profitable?This week’s Tuesday Tip flips the narrative. Architect and developer Prashanth Mahakali returns to share why new construction projects are the overlooked path to success for Chicago investors. Whether y...

Scaling in real estate is one of the most exciting milestones in an investor’s journey. Maybe you’ve bought a couple of smaller properties, proven you can operate them, and now you’re ready to partner with someone else to go after bigger opportunities. It sounds simple—pool money, buy bigger buildings, split profits—but without the right legal structure, things can unravel quickly.I’ve seen partnershi...

There’s a lot of talk about how veterans can transition into civilian life and build financial freedom, but few people are actually putting the pieces together like DuBois Toy. A Chicago native, Air Force veteran, cybersecurity pro, and real estate investor, DuBois combines military discipline with tech automation to create scalable systems for property investing. From AI-powered tenant screening to maximizing VA loan benefits an...

When you’re investing in Chicago real estate, whether you’re flipping bungalows in Ravenswood Manor or holding onto a multi-unit in Portage Park, you’re always looking for ways to reduce your tax burden and free up cash for your next deal. One of the most overlooked tools for doing that is cost segregation. In this episode of the Straight Up Chicago Investor Podcast, “Cost Seg Kev” (Kevin Cawley) breaks do...