CHICAGO'S #1 REAL ESTATE INVESTING PODCAST

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...

Not sure if your rent is right? 👉 Get a free analysisNavigating a major insurance claim after a disaster can be one of the most stressful situations a housing provider will ever face. Whether it’s a fire, flood, or even a small leak gone wrong, the gap between what you’re entitled to and what you actually receive can be staggering. On this episode of the Straight Up Chicago Investor Podcast, Mitch Schoeneman of Schoeneman...

Why Every Chicago Housing Provider Should Be at the 2025 NBOA Summer SoiréeSome events are fun. Some are powerful. Some move the needle for your business. The NBOA Summer Soirée? It’s all of that and more!In this Tuesday Tip episode, we’re joined by Mike Glasser, President of the Neighborhood Building Owners Alliance (NBOA), and Real Estate Nate, board member and local investor. Together, they break down why th...

In this episode of the Straight Up Chicago Investor Podcast, we get into how Sebastian scaled from Cutco sales to Airbnb arbitrage to property ownership. You’ll hear the no-BS version of what it takes to convince landlords, navigate Chicago's short-term rental laws, and balance profitability with hospitality. It’s a must-listen for any property manager or landlord curious about what’s really possible with short-ter...

There’s a lot of noise out there about what it takes to become a real estate investor. People talk big—“I’m going to own a hundred doors,” “I’m going to be financially free in two years,”—and then get stuck before they even make that first move. This episode is for those who are stuck, stalling, or simply need to see that it’s possible.Because Alex Diaz? He’s doing the da...

Let me just say this up front—if you're one of those investors thinking you need a hundred units and a fancy syndication to "make it," you’re missing the point. And in this episode, Katie and Rob Hayes make that crystal clear. They’ve built a portfolio that works for their lifestyle—not the other way around—and they’ve done it by staying local, staying focused, and staying in control. N...

A demand letter or legal notice from an attorney might be the first sign of legal trouble, or it could be just a bluff designed to scare you into overreacting. In this episode, attorney Bibek Das joins Mark Ainley and Tom Shallcross to demystify what a demand letter really is, what landlords should (and shouldn’t) do when receiving one, and why staying calm is your most powerful first move. If you own rental property in Chicago or...